diff --git a/.ci/scripts/auditwheel_wrapper.py b/.ci/scripts/auditwheel_wrapper.py
index 9599b79e50..9832821221 100755
--- a/.ci/scripts/auditwheel_wrapper.py
+++ b/.ci/scripts/auditwheel_wrapper.py
@@ -25,7 +25,6 @@
 import argparse
 import os
 import subprocess
-from typing import Optional
 from zipfile import ZipFile
 
 from packaging.tags import Tag
@@ -80,7 +79,7 @@ def cpython(wheel_file: str, name: str, version: Version, tag: Tag) -> str:
     return new_wheel_file
 
 
-def main(wheel_file: str, dest_dir: str, archs: Optional[str]) -> None:
+def main(wheel_file: str, dest_dir: str, archs: str | None) -> None:
     """Entry point"""
 
     # Parse the wheel file name into its parts. Note that `parse_wheel_filename`
diff --git a/.ci/scripts/calculate_jobs.py b/.ci/scripts/calculate_jobs.py
index 5249acdc5d..87fbc7a266 100755
--- a/.ci/scripts/calculate_jobs.py
+++ b/.ci/scripts/calculate_jobs.py
@@ -36,11 +36,11 @@ IS_PR = os.environ["GITHUB_REF"].startswith("refs/pull/")
 # First calculate the various trial jobs.
 #
 # For PRs, we only run each type of test with the oldest Python version supported (which
-# is Python 3.9 right now)
+# is Python 3.10 right now)
 
 trial_sqlite_tests = [
     {
-        "python-version": "3.9",
+        "python-version": "3.10",
         "database": "sqlite",
         "extras": "all",
     }
@@ -53,12 +53,12 @@ if not IS_PR:
             "database": "sqlite",
             "extras": "all",
         }
-        for version in ("3.10", "3.11", "3.12", "3.13")
+        for version in ("3.11", "3.12", "3.13", "3.14")
     )
 
 trial_postgres_tests = [
     {
-        "python-version": "3.9",
+        "python-version": "3.10",
         "database": "postgres",
         "postgres-version": "13",
         "extras": "all",
@@ -68,7 +68,7 @@ trial_postgres_tests = [
 if not IS_PR:
     trial_postgres_tests.append(
         {
-            "python-version": "3.13",
+            "python-version": "3.14",
             "database": "postgres",
             "postgres-version": "17",
             "extras": "all",
@@ -77,7 +77,7 @@ if not IS_PR:
 
 trial_no_extra_tests = [
     {
-        "python-version": "3.9",
+        "python-version": "3.10",
         "database": "sqlite",
         "extras": "",
     }
@@ -99,24 +99,24 @@ set_output("trial_test_matrix", test_matrix)
 
 # First calculate the various sytest jobs.
 #
-# For each type of test we only run on bullseye on PRs
+# For each type of test we only run on bookworm on PRs
 
 
 sytest_tests = [
     {
-        "sytest-tag": "bullseye",
+        "sytest-tag": "bookworm",
     },
     {
-        "sytest-tag": "bullseye",
+        "sytest-tag": "bookworm",
         "postgres": "postgres",
     },
     {
-        "sytest-tag": "bullseye",
+        "sytest-tag": "bookworm",
         "postgres": "multi-postgres",
         "workers": "workers",
     },
     {
-        "sytest-tag": "bullseye",
+        "sytest-tag": "bookworm",
         "postgres": "multi-postgres",
         "workers": "workers",
         "reactor": "asyncio",
@@ -127,11 +127,11 @@ if not IS_PR:
     sytest_tests.extend(
         [
             {
-                "sytest-tag": "bullseye",
+                "sytest-tag": "bookworm",
                 "reactor": "asyncio",
             },
             {
-                "sytest-tag": "bullseye",
+                "sytest-tag": "bookworm",
                 "postgres": "postgres",
                 "reactor": "asyncio",
             },
diff --git a/.github/workflows/docker.yml b/.github/workflows/docker.yml
index c88312f050..8bc045dc64 100644
--- a/.github/workflows/docker.yml
+++ b/.github/workflows/docker.yml
@@ -75,7 +75,7 @@ jobs:
           touch "${{ runner.temp }}/digests/${digest#sha256:}"
 
       - name: Upload digest
-        uses: actions/upload-artifact@v4
+        uses: actions/upload-artifact@v5
         with:
           name: digests-${{ matrix.suffix }}
           path: ${{ runner.temp }}/digests/*
@@ -95,7 +95,7 @@ jobs:
       - build
     steps:
       - name: Download digests
-        uses: actions/download-artifact@634f93cb2916e3fdff6788551b99b062d0335ce0 # v5.0.0
+        uses: actions/download-artifact@018cc2cf5baa6db3ef3c5f8a56943fffe632ef53 # v6.0.0
         with:
           path: ${{ runner.temp }}/digests
           pattern: digests-*
@@ -120,7 +120,7 @@ jobs:
         uses: docker/setup-buildx-action@e468171a9de216ec08956ac3ada2f0791b6bd435 # v3.11.1
 
       - name: Install Cosign
-        uses: sigstore/cosign-installer@d7543c93d881b35a8faa02e8e3605f69b7a1ce62 # v3.10.0
+        uses: sigstore/cosign-installer@faadad0cce49287aee09b3a48701e75088a2c6ad # v4.0.0
 
       - name: Calculate docker image tag
         uses: docker/metadata-action@c1e51972afc2121e065aed6d45c65596fe445f3f # v5.8.0
diff --git a/.github/workflows/docs-pr.yaml b/.github/workflows/docs-pr.yaml
index a0af38a6c5..6a61dd5fb1 100644
--- a/.github/workflows/docs-pr.yaml
+++ b/.github/workflows/docs-pr.yaml
@@ -39,7 +39,7 @@ jobs:
           cp book/welcome_and_overview.html book/index.html
 
       - name: Upload Artifact
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
         with:
           name: book
           path: book
diff --git a/.github/workflows/fix_lint.yaml b/.github/workflows/fix_lint.yaml
index 87f46078be..c33481a51e 100644
--- a/.github/workflows/fix_lint.yaml
+++ b/.github/workflows/fix_lint.yaml
@@ -47,6 +47,6 @@ jobs:
       - run: cargo fmt
         continue-on-error: true
 
-      - uses: stefanzweifel/git-auto-commit-action@778341af668090896ca464160c2def5d1d1a3eb0 # v6.0.1
+      - uses: stefanzweifel/git-auto-commit-action@28e16e81777b558cc906c8750092100bbb34c5e3 # v7.0.0
         with:
           commit_message: "Attempt to fix linting"
diff --git a/.github/workflows/latest_deps.yml b/.github/workflows/latest_deps.yml
index a00c52fcb2..2076a1c1e1 100644
--- a/.github/workflows/latest_deps.yml
+++ b/.github/workflows/latest_deps.yml
@@ -139,9 +139,9 @@ jobs:
       fail-fast: false
       matrix:
         include:
-          - sytest-tag: bullseye
+          - sytest-tag: bookworm
 
-          - sytest-tag: bullseye
+          - sytest-tag: bookworm
             postgres: postgres
             workers: workers
             redis: redis
@@ -173,7 +173,7 @@ jobs:
         if: ${{ always() }}
         run: /sytest/scripts/tap_to_gha.pl /logs/results.tap
       - name: Upload SyTest logs
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
         if: ${{ always() }}
         with:
           name: Sytest Logs - ${{ job.status }} - (${{ join(matrix.*, ', ') }})
diff --git a/.github/workflows/release-artifacts.yml b/.github/workflows/release-artifacts.yml
index 4969ca6723..d346aeb597 100644
--- a/.github/workflows/release-artifacts.yml
+++ b/.github/workflows/release-artifacts.yml
@@ -101,7 +101,7 @@ jobs:
           echo "ARTIFACT_NAME=${DISTRO#*:}" >> "$GITHUB_OUTPUT"
 
       - name: Upload debs as artifacts
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
         with:
           name: debs-${{ steps.artifact-name.outputs.ARTIFACT_NAME }}
           path: debs/*
@@ -114,8 +114,8 @@ jobs:
         os:
           - ubuntu-24.04
           - ubuntu-24.04-arm
-          - macos-13 # This uses x86-64
           - macos-14 # This uses arm64
+          - macos-15-intel # This uses x86-64
         # is_pr is a flag used to exclude certain jobs from the matrix on PRs.
         # It is not read by the rest of the workflow.
         is_pr:
@@ -124,7 +124,7 @@ jobs:
         exclude:
           # Don't build macos wheels on PR CI.
           - is_pr: true
-            os: "macos-13"
+            os: "macos-15-intel"
           - is_pr: true
             os: "macos-14"
           # Don't build aarch64 wheels on PR CI.
@@ -141,20 +141,23 @@ jobs:
           python-version: "3.x"
 
       - name: Install cibuildwheel
-        run: python -m pip install cibuildwheel==3.0.0
+        run: python -m pip install cibuildwheel==3.2.1
 
       - name: Only build a single wheel on PR
         if: startsWith(github.ref, 'refs/pull/')
-        run: echo "CIBW_BUILD="cp39-manylinux_*"" >> $GITHUB_ENV
+        run: echo "CIBW_BUILD="cp310-manylinux_*"" >> $GITHUB_ENV
 
       - name: Build wheels
         run: python -m cibuildwheel --output-dir wheelhouse
         env:
           # Skip testing for platforms which various libraries don't have wheels
           # for, and so need extra build deps.
-          CIBW_TEST_SKIP: pp3*-* *i686* *musl*
+          #
+          # cp39-*: Python 3.9 is EOL.
+          # cp3??t-*: Free-threaded builds are not currently supported.
+          CIBW_TEST_SKIP: pp3*-* cp39-* cp3??t-* *i686* *musl*
 
-      - uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+      - uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
         with:
           name: Wheel-${{ matrix.os }}
           path: ./wheelhouse/*.whl
@@ -175,7 +178,7 @@ jobs:
       - name: Build sdist
         run: python -m build --sdist
 
-      - uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+      - uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
         with:
           name: Sdist
           path: dist/*.tar.gz
@@ -191,7 +194,7 @@ jobs:
     runs-on: ubuntu-latest
     steps:
       - name: Download all workflow run artifacts
-        uses: actions/download-artifact@634f93cb2916e3fdff6788551b99b062d0335ce0 # v5.0.0
+        uses: actions/download-artifact@018cc2cf5baa6db3ef3c5f8a56943fffe632ef53 # v6.0.0
       - name: Build a tarball for the debs
         # We need to merge all the debs uploads into one folder, then compress
         # that.
@@ -200,16 +203,11 @@ jobs:
           mv debs*/* debs/
           tar -cvJf debs.tar.xz debs
       - name: Attach to release
-        # Pinned to work around https://github.com/softprops/action-gh-release/issues/445
-        uses: softprops/action-gh-release@c95fe1489396fe8a9eb87c0abf8aa5b2ef267fda # v0.1.15
         env:
           GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
-        with:
-          files: |
-            Sdist/*
-            Wheel*/*
-            debs.tar.xz
-          # if it's not already published, keep the release as a draft.
-          draft: true
-          # mark it as a prerelease if the tag contains 'rc'.
-          prerelease: ${{ contains(github.ref, 'rc') }}
+        run: |
+          gh release upload "${{ github.ref_name }}" \
+            Sdist/* \
+            Wheel*/* \
+            debs.tar.xz \
+            --repo ${{ github.repository }}
diff --git a/.github/workflows/tests.yml b/.github/workflows/tests.yml
index 6b8cb3c585..4f38ab0690 100644
--- a/.github/workflows/tests.yml
+++ b/.github/workflows/tests.yml
@@ -207,26 +207,6 @@ jobs:
         env:
           PULL_REQUEST_NUMBER: ${{ github.event.number }}
 
-  lint-pydantic:
-    runs-on: ubuntu-latest
-    needs: changes
-    if: ${{ needs.changes.outputs.linting == 'true' }}
-
-    steps:
-      - uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
-        with:
-          ref: ${{ github.event.pull_request.head.sha }}
-      - name: Install Rust
-        uses: dtolnay/rust-toolchain@e97e2d8cc328f1b50210efc529dca0028893a2d9 # master
-        with:
-          toolchain: ${{ env.RUST_VERSION }}
-      - uses: Swatinem/rust-cache@f13886b937689c021905a6b90929199931d60db1 # v2.8.1
-      - uses: matrix-org/setup-python-poetry@5bbf6603c5c930615ec8a29f1b5d7d258d905aa4 # v2.0.0
-        with:
-          poetry-version: "2.1.1"
-          extras: "all"
-      - run: poetry run scripts-dev/check_pydantic_models.py
-
   lint-clippy:
     runs-on: ubuntu-latest
     needs: changes
@@ -341,7 +321,6 @@ jobs:
       - lint-mypy
       - lint-crlf
       - lint-newsfile
-      - lint-pydantic
       - check-sampleconfig
       - check-schema-delta
       - check-lockfile
@@ -363,7 +342,6 @@ jobs:
             lint
             lint-mypy
             lint-newsfile
-            lint-pydantic
             lint-clippy
             lint-clippy-nightly
             lint-rust
@@ -470,7 +448,7 @@ jobs:
 
       - uses: actions/setup-python@e797f83bcb11b83ae66e0230d6156d7c80228e7c # v6.0.0
         with:
-          python-version: '3.9'
+          python-version: '3.10'
 
       - name: Prepare old deps
         if: steps.cache-poetry-old-deps.outputs.cache-hit != 'true'
@@ -514,7 +492,7 @@ jobs:
     runs-on: ubuntu-latest
     strategy:
       matrix:
-        python-version: ["pypy-3.9"]
+        python-version: ["pypy-3.10"]
         extras: ["all"]
 
     steps:
@@ -585,7 +563,7 @@ jobs:
         if: ${{ always() }}
         run: /sytest/scripts/tap_to_gha.pl /logs/results.tap
       - name: Upload SyTest logs
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
         if: ${{ always() }}
         with:
           name: Sytest Logs - ${{ job.status }} - (${{ join(matrix.job.*, ', ') }})
@@ -638,10 +616,10 @@ jobs:
     strategy:
       matrix:
         include:
-          - python-version: "3.9"
+          - python-version: "3.10"
             postgres-version: "13"
 
-          - python-version: "3.13"
+          - python-version: "3.14"
             postgres-version: "17"
 
     services:
@@ -683,7 +661,7 @@ jobs:
           PGPASSWORD: postgres
           PGDATABASE: postgres
       - name: "Upload schema differences"
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
         if: ${{ failure() && !cancelled() && steps.run_tester_script.outcome == 'failure' }}
         with:
           name: Schema dumps
diff --git a/.github/workflows/twisted_trunk.yml b/.github/workflows/twisted_trunk.yml
index 04a8db2cc7..11b7bfe143 100644
--- a/.github/workflows/twisted_trunk.yml
+++ b/.github/workflows/twisted_trunk.yml
@@ -108,11 +108,11 @@ jobs:
     if: needs.check_repo.outputs.should_run_workflow == 'true'
     runs-on: ubuntu-latest
     container:
-      # We're using debian:bullseye because it uses Python 3.9 which is our minimum supported Python version.
+      # We're using bookworm because that's what Debian oldstable is at the time of writing.
       # This job is a canary to warn us about unreleased twisted changes that would cause problems for us if
       # they were to be released immediately. For simplicity's sake (and to save CI runners) we use the oldest
       # version, assuming that any incompatibilities on newer versions would also be present on the oldest.
-      image: matrixdotorg/sytest-synapse:bullseye
+      image: matrixdotorg/sytest-synapse:bookworm
       volumes:
         - ${{ github.workspace }}:/src
 
@@ -147,7 +147,7 @@ jobs:
         if: ${{ always() }}
         run: /sytest/scripts/tap_to_gha.pl /logs/results.tap
       - name: Upload SyTest logs
-        uses: actions/upload-artifact@ea165f8d65b6e75b540449e92b4886f43607fa02 # v4.6.2
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5.0.0
         if: ${{ always() }}
         with:
           name: Sytest Logs - ${{ job.status }} - (${{ join(matrix.*, ', ') }})
diff --git a/CHANGES.md b/CHANGES.md
index e1680d134a..8fbd50f20e 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -1,3 +1,347 @@
+# Synapse 1.142.0rc4 (2025-11-07)
+
+## Dropped support for Python 3.9
+
+This release drops support for Python 3.9, in line with our [dependency
+deprecation
+policy](https://element-hq.github.io/synapse/latest/deprecation_policy.html#platform-dependencies),
+as it is now [end of life](https://endoflife.date/python).
+
+## SQLite 3.40.0+ is now required
+
+The minimum supported SQLite version has been increased from 3.27.0 to 3.40.0.
+
+If you use current versions of the
+[matrixorg/synapse](setup/installation.html#docker-images-and-ansible-playbooks)
+Docker images, no action is required.
+
+
+## Deprecation of MacOS Python wheels
+
+The team has decided to deprecate and eventually stop publishing python wheels
+for MacOS. This is a burden on the team, and we're not aware of any parties
+that use them. Synapse docker images will continue to work on MacOS, as will
+building Synapse from source (though note this requires a Rust compiler).
+
+At present, publishing MacOS Python wheels will continue for the next release
+(1.143.0), but will not be available after that (1.144.0+). If you do make use
+of these wheels downstream, please reach out to us in
+[#synapse-dev:matrix.org](https://matrix.to/#/#synapse-dev:matrix.org). We'd
+love to hear from you!
+
+## Bugfixes
+
+- Fix a bug introduced in 1.142.0rc1 where any attempt to configure `matrix_authentication_service.secret_path` would prevent the homeserver from starting up. ([\#19144](https://github.com/element-hq/synapse/issues/19144))
+
+
+
+
+# Synapse 1.142.0rc3 (2025-11-04)
+
+## Internal Changes
+
+- Update release scripts to prevent building wheels for free-threaded Python, as Synapse does not currently support it. ([\#19140](https://github.com/element-hq/synapse/issues/19140))
+
+
+# Synapse 1.142.0rc2 (2025-11-04)
+
+
+## Internal Changes
+
+- Manually skip building Python 3.9 wheels, to prevent errors in the release workflow. ([\#19119](https://github.com/element-hq/synapse/issues/19119))
+
+
+
+
+# Synapse 1.142.0rc1 (2025-11-04)
+
+## Features
+
+- Add support for Python 3.14. ([\#19055](https://github.com/element-hq/synapse/issues/19055), [\#19134](https://github.com/element-hq/synapse/issues/19134))
+- Add an [Admin API](https://element-hq.github.io/synapse/latest/usage/administration/admin_api/index.html)
+  to allow an admin to fetch the space/room hierarchy for a given space. ([\#19021](https://github.com/element-hq/synapse/issues/19021))
+
+## Bugfixes
+
+- Fix a bug introduced in 1.111.0 where failed attempts to download authenticated remote media would not be handled correctly. ([\#19062](https://github.com/element-hq/synapse/issues/19062))
+- Update the `oidc_session_no_samesite` cookie to have the `Secure` attribute, so the only difference between it and the paired `oidc_session` cookie, is the configuration of the `SameSite` attribute as described in the comments / cookie names. Contributed by @kieranlane. ([\#19079](https://github.com/element-hq/synapse/issues/19079))
+- Fix a bug introduced in 1.140.0 where lost logcontext warnings would be emitted from timeouts in sync and requests made by Synapse itself. ([\#19090](https://github.com/element-hq/synapse/issues/19090))
+- Fix a bug introdued in 1.140.0 where lost logcontext warning were emitted when using `HomeServer.shutdown()`. ([\#19108](https://github.com/element-hq/synapse/issues/19108))
+
+## Improved Documentation
+
+- Update the link to the Debian oldstable package for SQLite. ([\#19047](https://github.com/element-hq/synapse/issues/19047))
+- Point out additional Redis configuration options available in the worker docs. Contributed by @servisbryce. ([\#19073](https://github.com/element-hq/synapse/issues/19073))
+- Update the list of Debian releases that the downstream Debian package is maintained for. ([\#19100](https://github.com/element-hq/synapse/issues/19100))
+- Add [a page](https://element-hq.github.io/synapse/latest/development/internal_documentation/release_notes_review_checklist.html) to the documentation describing the steps the Synapse team takes to review the release notes before publishing them. ([\#19109](https://github.com/element-hq/synapse/issues/19109))
+
+## Deprecations and Removals
+
+- Drop support for Python 3.9. ([\#19099](https://github.com/element-hq/synapse/issues/19099))
+- Remove support for SQLite < 3.37.2. ([\#19047](https://github.com/element-hq/synapse/issues/19047))
+
+## Internal Changes
+
+- Fix CI linter for schema delta files to correctly handle all types of `CREATE TABLE` syntax. ([\#19020](https://github.com/element-hq/synapse/issues/19020))
+- Use type hinting generics in standard collections, as per [PEP 585](https://peps.python.org/pep-0585/), added in Python 3.9. ([\#19046](https://github.com/element-hq/synapse/issues/19046))
+- Always treat `RETURNING` as supported by SQL engines, now that the minimum-supported versions of both SQLite and PostgreSQL support it. ([\#19047](https://github.com/element-hq/synapse/issues/19047))
+- Move `oidc.load_metadata()` startup into `_base.start()`. ([\#19056](https://github.com/element-hq/synapse/issues/19056))
+- Remove logcontext problems caused by awaiting raw `deferLater(...)`. ([\#19058](https://github.com/element-hq/synapse/issues/19058))
+- Prevent duplicate logging setup when running multiple Synapse instances. ([\#19067](https://github.com/element-hq/synapse/issues/19067))
+- Be mindful of other logging context filters in 3rd-party code and avoid overwriting log record fields unless we know the log record is relevant to Synapse. ([\#19068](https://github.com/element-hq/synapse/issues/19068))
+- Update pydantic to v2. ([\#19071](https://github.com/element-hq/synapse/issues/19071))
+- Update deprecated code in the release script to prevent a warning message from being printed. ([\#19080](https://github.com/element-hq/synapse/issues/19080))
+- Update the deprecated poetry development dependencies group name in `pyproject.toml`. ([\#19081](https://github.com/element-hq/synapse/issues/19081))
+- Remove `pp38*` skip selector from cibuildwheel to silence warning. ([\#19085](https://github.com/element-hq/synapse/issues/19085))
+- Don't immediately exit the release script if the checkout is dirty. Instead, allow the user to clear the dirty changes and retry. ([\#19088](https://github.com/element-hq/synapse/issues/19088))
+- Update the release script's generated announcement text to include a title and extra text for RC's. ([\#19089](https://github.com/element-hq/synapse/issues/19089))
+- Fix lints on main branch. ([\#19092](https://github.com/element-hq/synapse/issues/19092))
+- Use cheaper random string function in logcontext utilities. ([\#19094](https://github.com/element-hq/synapse/issues/19094))
+- Avoid clobbering other `SIGHUP` handlers in 3rd-party code. ([\#19095](https://github.com/element-hq/synapse/issues/19095))
+- Prevent duplicate GitHub draft releases being created during the Synapse release process. ([\#19096](https://github.com/element-hq/synapse/issues/19096))
+- Use Pillow's `Image.getexif` method instead of the experimental `Image._getexif`. ([\#19098](https://github.com/element-hq/synapse/issues/19098))
+- Prevent uv `/usr/local/.lock` file from appearing in built Synapse docker images. ([\#19107](https://github.com/element-hq/synapse/issues/19107))
+- Allow Synapse's runtime dependency checking code to take packaging markers (i.e. `python <= 3.14`) into account when checking dependencies. ([\#19110](https://github.com/element-hq/synapse/issues/19110))
+- Move exception handling up the stack (avoid `exit(1)` in our composable functions). ([\#19116](https://github.com/element-hq/synapse/issues/19116))
+- Fix a lint error related to lifetimes in Rust 1.90. ([\#19118](https://github.com/element-hq/synapse/issues/19118))
+- Refactor and align app entrypoints (avoid `exit(1)` in our composable functions). ([\#19121](https://github.com/element-hq/synapse/issues/19121), [\#19131](https://github.com/element-hq/synapse/issues/19131))
+- Speed up pruning of ratelimiters. ([\#19129](https://github.com/element-hq/synapse/issues/19129))
+
+
+
+### Updates to locked dependencies
+
+* Bump actions/download-artifact from 5.0.0 to 6.0.0. ([\#19102](https://github.com/element-hq/synapse/issues/19102))
+* Bump actions/upload-artifact from 4 to 5. ([\#19106](https://github.com/element-hq/synapse/issues/19106))
+* Bump hiredis from 3.2.1 to 3.3.0. ([\#19103](https://github.com/element-hq/synapse/issues/19103))
+* Bump icu_segmenter from 2.0.0 to 2.0.1. ([\#19126](https://github.com/element-hq/synapse/issues/19126))
+* Bump idna from 3.10 to 3.11. ([\#19053](https://github.com/element-hq/synapse/issues/19053))
+* Bump ijson from 3.4.0 to 3.4.0.post0. ([\#19051](https://github.com/element-hq/synapse/issues/19051))
+* Bump markdown-it-py from 3.0.0 to 4.0.0. ([\#19123](https://github.com/element-hq/synapse/issues/19123))
+* Bump msgpack from 1.1.1 to 1.1.2. ([\#19050](https://github.com/element-hq/synapse/issues/19050))
+* Bump psycopg2 from 2.9.10 to 2.9.11. ([\#19125](https://github.com/element-hq/synapse/issues/19125))
+* Bump pyyaml from 6.0.2 to 6.0.3. ([\#19105](https://github.com/element-hq/synapse/issues/19105))
+* Bump regex from 1.11.3 to 1.12.2. ([\#19074](https://github.com/element-hq/synapse/issues/19074))
+* Bump reqwest from 0.12.23 to 0.12.24. ([\#19077](https://github.com/element-hq/synapse/issues/19077))
+* Bump ruff from 0.12.10 to 0.14.3. ([\#19124](https://github.com/element-hq/synapse/issues/19124))
+* Bump sigstore/cosign-installer from 3.10.0 to 4.0.0. ([\#19075](https://github.com/element-hq/synapse/issues/19075))
+* Bump stefanzweifel/git-auto-commit-action from 6.0.1 to 7.0.0. ([\#19052](https://github.com/element-hq/synapse/issues/19052))
+* Bump tokio from 1.47.1 to 1.48.0. ([\#19076](https://github.com/element-hq/synapse/issues/19076))
+* Bump types-psycopg2 from 2.9.21.20250915 to 2.9.21.20251012. ([\#19054](https://github.com/element-hq/synapse/issues/19054))
+
+# Synapse 1.141.0 (2025-10-29)
+
+## Deprecation of MacOS Python wheels
+
+The team has decided to deprecate and eventually stop publishing python wheels
+for MacOS. This is a burden on the team, and we're not aware of any parties
+that use them. Synapse docker images will continue to work on MacOS, as will
+building Synapse from source (though note this requires a Rust compiler).
+
+Publishing MacOS Python wheels will continue for the next few releases. If you
+do make use of these wheels downstream, please reach out to us in
+[#synapse-dev:matrix.org](https://matrix.to/#/#synapse-dev:matrix.org). We'd
+love to hear from you!
+
+
+## Docker images now based on Debian `trixie` with Python 3.13
+
+The Docker images are now based on Debian `trixie` and use Python 3.13. If you
+are using the Docker images as a base image you may need to e.g. adjust the
+paths you mount any additional Python packages at.
+
+No significant changes since 1.141.0rc2.
+
+
+
+
+# Synapse 1.141.0rc2 (2025-10-28)
+
+## Bugfixes
+
+- Fix users being unable to log in if their password, or the server's configured pepper, was too long. ([\#19101](https://github.com/element-hq/synapse/issues/19101))
+
+
+
+
+# Synapse 1.141.0rc1 (2025-10-21)
+
+## Features
+
+- Allow using [MSC4190](https://github.com/matrix-org/matrix-spec-proposals/pull/4190) behavior without the opt-in registration flag. Contributed by @tulir @ Beeper. ([\#19031](https://github.com/element-hq/synapse/issues/19031))
+- Stabilized support for [MSC4326](https://github.com/matrix-org/matrix-spec-proposals/pull/4326): Device masquerading for appservices. Contributed by @tulir @ Beeper. ([\#19033](https://github.com/element-hq/synapse/issues/19033))
+
+## Bugfixes
+
+- Fix a bug introduced in 1.136.0 that would prevent Synapse from being able to be `reload`-ed more than once when running under systemd. ([\#19060](https://github.com/element-hq/synapse/issues/19060))
+- Fix a bug introduced in 1.140.0 where an internal server error could be raised when hashing user passwords that are too long. ([\#19078](https://github.com/element-hq/synapse/issues/19078))
+
+## Updates to the Docker image
+
+- Update docker image to use Debian trixie as the base and thus Python 3.13. ([\#19064](https://github.com/element-hq/synapse/issues/19064))
+
+## Internal Changes
+
+- Move unique snowflake homeserver background tasks to `start_background_tasks` (the standard pattern for this kind of thing). ([\#19037](https://github.com/element-hq/synapse/issues/19037))
+- Drop a deprecated field of the `PyGitHub` dependency in the release script and raise the dependency's minimum version to `1.59.0`. ([\#19039](https://github.com/element-hq/synapse/issues/19039))
+- Update TODO list of conflicting areas where we encounter metrics being clobbered (`ApplicationService`). ([\#19040](https://github.com/element-hq/synapse/issues/19040))
+
+
+
+
+# Synapse 1.140.0 (2025-10-14)
+
+## Compatibility notice for users of `synapse-s3-storage-provider`
+
+Deployments that make use of the
+[synapse-s3-storage-provider](https://github.com/matrix-org/synapse-s3-storage-provider)
+module must upgrade to
+[v1.6.0](https://github.com/matrix-org/synapse-s3-storage-provider/releases/tag/v1.6.0).
+Using older versions of the module with this release of Synapse will prevent
+users from being able to upload or download media.
+
+
+No significant changes since 1.140.0rc1.
+
+
+
+
+# Synapse 1.140.0rc1 (2025-10-10)
+
+## Features
+
+- Add [a new Media Query by ID Admin API](https://element-hq.github.io/synapse/v1.140/admin_api/media_admin_api.html#query-a-piece-of-media-by-id) that allows server admins to query and investigate the metadata of local or cached remote media via
+  the `origin/media_id` identifier found in a [Matrix Content URI](https://spec.matrix.org/v1.14/client-server-api/#matrix-content-mxc-uris). ([\#18911](https://github.com/element-hq/synapse/issues/18911))
+- Add [a new Fetch Event Admin API](https://element-hq.github.io/synapse/v1.140/admin_api/fetch_event.html) to fetch an event by ID. ([\#18963](https://github.com/element-hq/synapse/issues/18963))
+- Update [MSC4284: Policy Servers](https://github.com/matrix-org/matrix-spec-proposals/pull/4284) implementation to support signatures when available. ([\#18934](https://github.com/element-hq/synapse/issues/18934))
+- Add experimental implementation of the `GET /_matrix/client/v1/rtc/transports` endpoint for the latest draft of [MSC4143: MatrixRTC](https://github.com/matrix-org/matrix-spec-proposals/pull/4143). ([\#18967](https://github.com/element-hq/synapse/issues/18967))
+- Expose a `defer_to_threadpool` function in the Synapse Module API that allows modules to run a function on a separate thread in a custom threadpool. ([\#19032](https://github.com/element-hq/synapse/issues/19032))
+
+## Bugfixes
+
+- Fix room upgrade `room_config` argument and documentation for `user_may_create_room` spam-checker callback. ([\#18721](https://github.com/element-hq/synapse/issues/18721))
+- Compute a user's last seen timestamp from their devices' last seen timestamps instead of IPs, because the latter are automatically cleared according to `user_ips_max_age`. ([\#18948](https://github.com/element-hq/synapse/issues/18948))
+- Fix bug where ephemeral events were not filtered by room ID. Contributed by @frastefanini. ([\#19002](https://github.com/element-hq/synapse/issues/19002))
+- Update Synapse main process version string to include git info. ([\#19011](https://github.com/element-hq/synapse/issues/19011))
+
+## Improved Documentation
+
+- Explain how `Deferred` callbacks interact with logcontexts. ([\#18914](https://github.com/element-hq/synapse/issues/18914))
+- Fix documentation for `rc_room_creation` and `rc_reports` to clarify that a `per_user` rate limit is not supported. ([\#18998](https://github.com/element-hq/synapse/issues/18998))
+
+## Deprecations and Removals
+
+- Remove deprecated `LoggingContext.set_current_context`/`LoggingContext.current_context` methods which already have equivalent bare methods in `synapse.logging.context`. ([\#18989](https://github.com/element-hq/synapse/issues/18989))
+- Drop support for unstable field names from the long-accepted [MSC2732](https://github.com/matrix-org/matrix-spec-proposals/pull/2732) (Olm fallback keys) proposal. ([\#18996](https://github.com/element-hq/synapse/issues/18996))
+
+## Internal Changes
+
+- Cleanly shutdown `SynapseHomeServer` object, allowing artifacts of embedded small hosts to be properly garbage collected. ([\#18828](https://github.com/element-hq/synapse/issues/18828))
+- Update OEmbed providers to use 'X' instead of 'Twitter' in URL previews, following a rebrand. Contributed by @HammyHavoc. ([\#18767](https://github.com/element-hq/synapse/issues/18767))
+- Fix `server_name` in logging context for multiple Synapse instances in one process. ([\#18868](https://github.com/element-hq/synapse/issues/18868))
+- Wrap the Rust HTTP client with `make_deferred_yieldable` so it follows Synapse logcontext rules. ([\#18903](https://github.com/element-hq/synapse/issues/18903))
+- Fix the GitHub Actions workflow that moves issues labeled "X-Needs-Info" to the "Needs info" column on the team's internal triage board. ([\#18913](https://github.com/element-hq/synapse/issues/18913))
+- Disconnect background process work from request trace. ([\#18932](https://github.com/element-hq/synapse/issues/18932))
+- Reduce overall number of calls to `_get_e2e_cross_signing_signatures_for_devices` by increasing the batch size of devices the query is called with, reducing DB load. ([\#18939](https://github.com/element-hq/synapse/issues/18939))
+- Update error code used when an appservice tries to masquerade as an unknown device using [MSC4326](https://github.com/matrix-org/matrix-spec-proposals/pull/4326). Contributed by @tulir @ Beeper. ([\#18947](https://github.com/element-hq/synapse/issues/18947))
+- Fix `no active span when trying to log` tracing error on startup (when OpenTracing is enabled). ([\#18959](https://github.com/element-hq/synapse/issues/18959))
+- Fix `run_coroutine_in_background(...)` incorrectly handling logcontext. ([\#18964](https://github.com/element-hq/synapse/issues/18964))
+- Add debug logs wherever we change current logcontext. ([\#18966](https://github.com/element-hq/synapse/issues/18966))
+- Update dockerfile metadata to fix broken link; point to documentation website. ([\#18971](https://github.com/element-hq/synapse/issues/18971))
+- Note that the code is additionally licensed under the [Element Commercial license](https://github.com/element-hq/synapse/blob/develop/LICENSE-COMMERCIAL) in SPDX expression field configs. ([\#18973](https://github.com/element-hq/synapse/issues/18973))
+- Fix logcontext handling in `timeout_deferred` tests. ([\#18974](https://github.com/element-hq/synapse/issues/18974))
+- Remove internal `ReplicationUploadKeysForUserRestServlet` as a follow-up to the work in https://github.com/element-hq/synapse/pull/18581 that moved device changes off the main process. ([\#18988](https://github.com/element-hq/synapse/issues/18988))
+- Switch task scheduler from raw logcontext manipulation to using the dedicated logcontext utils. ([\#18990](https://github.com/element-hq/synapse/issues/18990))
+- Remove `MockClock()` in tests. ([\#18992](https://github.com/element-hq/synapse/issues/18992))
+- Switch back to our own custom `LogContextScopeManager` instead of OpenTracing's `ContextVarsScopeManager` which was causing problems when using the experimental `SYNAPSE_ASYNC_IO_REACTOR` option with tracing enabled. ([\#19007](https://github.com/element-hq/synapse/issues/19007))
+- Remove `version_string` argument from `HomeServer` since it's always the same. ([\#19012](https://github.com/element-hq/synapse/issues/19012))
+- Remove duplicate call to `hs.start_background_tasks()` introduced from a bad merge. ([\#19013](https://github.com/element-hq/synapse/issues/19013))
+- Split homeserver creation (`create_homeserver`) and setup (`setup`). ([\#19015](https://github.com/element-hq/synapse/issues/19015))
+- Swap near-end-of-life `macos-13` GitHub Actions runner for the `macos-15-intel` variant. ([\#19025](https://github.com/element-hq/synapse/issues/19025))
+- Introduce `RootConfig.validate_config()` which can be subclassed in `HomeServerConfig` to do cross-config class validation. ([\#19027](https://github.com/element-hq/synapse/issues/19027))
+- Allow any command of the `release.py` script to accept a `--gh-token` argument. ([\#19035](https://github.com/element-hq/synapse/issues/19035))
+
+
+
+### Updates to locked dependencies
+
+* Bump Swatinem/rust-cache from 2.8.0 to 2.8.1. ([\#18949](https://github.com/element-hq/synapse/issues/18949))
+* Bump actions/cache from 4.2.4 to 4.3.0. ([\#18983](https://github.com/element-hq/synapse/issues/18983))
+* Bump anyhow from 1.0.99 to 1.0.100. ([\#18950](https://github.com/element-hq/synapse/issues/18950))
+* Bump authlib from 1.6.3 to 1.6.4. ([\#18957](https://github.com/element-hq/synapse/issues/18957))
+* Bump authlib from 1.6.4 to 1.6.5. ([\#19019](https://github.com/element-hq/synapse/issues/19019))
+* Bump bcrypt from 4.3.0 to 5.0.0. ([\#18984](https://github.com/element-hq/synapse/issues/18984))
+* Bump docker/login-action from 3.5.0 to 3.6.0. ([\#18978](https://github.com/element-hq/synapse/issues/18978))
+* Bump lxml from 6.0.0 to 6.0.2. ([\#18979](https://github.com/element-hq/synapse/issues/18979))
+* Bump phonenumbers from 9.0.13 to 9.0.14. ([\#18954](https://github.com/element-hq/synapse/issues/18954))
+* Bump phonenumbers from 9.0.14 to 9.0.15. ([\#18991](https://github.com/element-hq/synapse/issues/18991))
+* Bump prometheus-client from 0.22.1 to 0.23.1. ([\#19016](https://github.com/element-hq/synapse/issues/19016))
+* Bump pydantic from 2.11.9 to 2.11.10. ([\#19017](https://github.com/element-hq/synapse/issues/19017))
+* Bump pygithub from 2.7.0 to 2.8.1. ([\#18952](https://github.com/element-hq/synapse/issues/18952))
+* Bump regex from 1.11.2 to 1.11.3. ([\#18981](https://github.com/element-hq/synapse/issues/18981))
+* Bump serde from 1.0.224 to 1.0.226. ([\#18953](https://github.com/element-hq/synapse/issues/18953))
+* Bump serde from 1.0.226 to 1.0.228. ([\#18982](https://github.com/element-hq/synapse/issues/18982))
+* Bump setuptools-rust from 1.11.1 to 1.12.0. ([\#18980](https://github.com/element-hq/synapse/issues/18980))
+* Bump twine from 6.1.0 to 6.2.0. ([\#18985](https://github.com/element-hq/synapse/issues/18985))
+* Bump types-pyyaml from 6.0.12.20250809 to 6.0.12.20250915. ([\#19018](https://github.com/element-hq/synapse/issues/19018))
+* Bump types-requests from 2.32.4.20250809 to 2.32.4.20250913. ([\#18951](https://github.com/element-hq/synapse/issues/18951))
+* Bump typing-extensions from 4.14.1 to 4.15.0. ([\#18956](https://github.com/element-hq/synapse/issues/18956))
+
+# Synapse 1.139.2 (2025-10-07)
+
+## Bugfixes
+
+- Fix a bug introduced in 1.139.1 where a client could receive an Internal Server Error if they set `device_keys: null` in the request to [`POST /_matrix/client/v3/keys/upload`](https://spec.matrix.org/v1.16/client-server-api/#post_matrixclientv3keysupload). ([\#19023](https://github.com/element-hq/synapse/issues/19023))
+
+
+
+
+# Synapse 1.139.1 (2025-10-07)
+
+## Security Fixes
+
+- Fix [CVE-2025-61672](https://www.cve.org/CVERecord?id=CVE-2025-61672) / [GHSA-fh66-fcv5-jjfr](https://github.com/element-hq/synapse/security/advisories/GHSA-fh66-fcv5-jjfr). Lack of validation for device keys in Synapse before 1.139.1 allows an attacker registered on the victim homeserver to degrade federation functionality, unpredictably breaking outbound federation to other homeservers. ([\#17097](https://github.com/element-hq/synapse/issues/17097))
+
+## Deprecations and Removals
+
+- Drop support for unstable field names from the long-accepted [MSC2732](https://github.com/matrix-org/matrix-spec-proposals/pull/2732) (Olm fallback keys) proposal. This change allows unit tests to pass following the security patch above. ([\#18996](https://github.com/element-hq/synapse/issues/18996))
+
+
+
+# Synapse 1.138.4 (2025-10-07)
+
+## Bugfixes
+
+- Fix a bug introduced in 1.138.3 where a client could receive an Internal Server Error if they set `device_keys: null` in the request to [`POST /_matrix/client/v3/keys/upload`](https://spec.matrix.org/v1.16/client-server-api/#post_matrixclientv3keysupload). ([\#19023](https://github.com/element-hq/synapse/issues/19023))
+
+
+
+
+# Synapse 1.138.3 (2025-10-07)
+
+## Security Fixes
+
+- Fix [CVE-2025-61672](https://www.cve.org/CVERecord?id=CVE-2025-61672) / [GHSA-fh66-fcv5-jjfr](https://github.com/element-hq/synapse/security/advisories/GHSA-fh66-fcv5-jjfr). Lack of validation for device keys in Synapse before 1.139.1 allows an attacker registered on the victim homeserver to degrade federation functionality, unpredictably breaking outbound federation to other homeservers. ([\#17097](https://github.com/element-hq/synapse/issues/17097))
+
+## Deprecations and Removals
+
+- Drop support for unstable field names from the long-accepted [MSC2732](https://github.com/matrix-org/matrix-spec-proposals/pull/2732) (Olm fallback keys) proposal. This change allows unit tests to pass following the security patch above. ([\#18996](https://github.com/element-hq/synapse/issues/18996))
+
+# Synapse 1.139.0 (2025-09-30)
+
+### `/register` requests from old application service implementations may break when using MAS
+
+If you are using Matrix Authentication Service (MAS), as of this release any
+Application Services that do not set `inhibit_login=true` when calling `POST
+/_matrix/client/v3/register` will receive the error
+`IO.ELEMENT.MSC4190.M_APPSERVICE_LOGIN_UNSUPPORTED` in response. Please see [the
+upgrade
+notes](https://element-hq.github.io/synapse/develop/upgrade.html#register-requests-from-old-application-service-implementations-may-break-when-using-mas)
+for more information.
+
+No significant changes since 1.139.0rc3.
+
+
 # Synapse 1.139.0rc3 (2025-09-25)
 
 ## Bugfixes
diff --git a/Cargo.lock b/Cargo.lock
index 321f1c7933..3ff8f2c477 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -2,21 +2,6 @@
 # It is not intended for manual editing.
 version = 3
 
-[[package]]
-name = "addr2line"
-version = "0.24.2"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "dfbe277e56a376000877090da837660b4427aad530e3028d44e0bffe4f89a1c1"
-dependencies = [
- "gimli",
-]
-
-[[package]]
-name = "adler2"
-version = "2.0.1"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "320119579fcad9c21884f5c4861d16174d0e06250625266f50fe6898340abefa"
-
 [[package]]
 name = "aho-corasick"
 version = "1.1.3"
@@ -50,21 +35,6 @@ version = "1.5.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "c08606f8c3cbf4ce6ec8e28fb0014a2c086708fe954eaa885384a6165172e7e8"
 
-[[package]]
-name = "backtrace"
-version = "0.3.75"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "6806a6321ec58106fea15becdad98371e28d92ccbc7c8f1b3b6dd724fe8f1002"
-dependencies = [
- "addr2line",
- "cfg-if",
- "libc",
- "miniz_oxide",
- "object",
- "rustc-demangle",
- "windows-targets",
-]
-
 [[package]]
 name = "base64"
 version = "0.22.1"
@@ -341,12 +311,6 @@ dependencies = [
  "wasm-bindgen",
 ]
 
-[[package]]
-name = "gimli"
-version = "0.31.1"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "07e28edb80900c19c28f1072f2e8aeca7fa06b23cd4169cefe1af5aa3260783f"
-
 [[package]]
 name = "h2"
 version = "0.4.11"
@@ -625,9 +589,9 @@ dependencies = [
 
 [[package]]
 name = "icu_segmenter"
-version = "2.0.0"
+version = "2.0.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "e185fc13b6401c138cf40db12b863b35f5edf31b88192a545857b41aeaf7d3d3"
+checksum = "38e30e593cf9c3ca2f51aa312eb347cd1ba95715e91a842ec3fc9058eab2af4b"
 dependencies = [
  "core_maths",
  "displaydoc",
@@ -684,17 +648,6 @@ version = "2.0.6"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "f4c7245a08504955605670dbf141fceab975f15ca21570696aebe9d2e71576bd"
 
-[[package]]
-name = "io-uring"
-version = "0.7.9"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "d93587f37623a1a17d94ef2bc9ada592f5465fe7732084ab7beefabe5c77c0c4"
-dependencies = [
- "bitflags",
- "cfg-if",
- "libc",
-]
-
 [[package]]
 name = "ipnet"
 version = "2.11.0"
@@ -784,15 +737,6 @@ version = "0.3.17"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "6877bb514081ee2a7ff5ef9de3281f14a4dd4bceac4c09388074a6b5df8a139a"
 
-[[package]]
-name = "miniz_oxide"
-version = "0.8.9"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "1fa76a2c86f704bdb222d66965fb3d63269ce38518b83cb0575fca855ebb6316"
-dependencies = [
- "adler2",
-]
-
 [[package]]
 name = "mio"
 version = "1.0.4"
@@ -804,15 +748,6 @@ dependencies = [
  "windows-sys 0.59.0",
 ]
 
-[[package]]
-name = "object"
-version = "0.36.7"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "62948e14d923ea95ea2c7c86c71013138b66525b86bdc08d2dcc262bdb497b87"
-dependencies = [
- "memchr",
-]
-
 [[package]]
 name = "once_cell"
 version = "1.21.3"
@@ -879,9 +814,9 @@ dependencies = [
 
 [[package]]
 name = "pyo3"
-version = "0.25.1"
+version = "0.26.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "8970a78afe0628a3e3430376fc5fd76b6b45c4d43360ffd6cdd40bdde72b682a"
+checksum = "7ba0117f4212101ee6544044dae45abe1083d30ce7b29c4b5cbdfa2354e07383"
 dependencies = [
  "anyhow",
  "indoc",
@@ -897,19 +832,18 @@ dependencies = [
 
 [[package]]
 name = "pyo3-build-config"
-version = "0.25.1"
+version = "0.26.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "458eb0c55e7ece017adeba38f2248ff3ac615e53660d7c71a238d7d2a01c7598"
+checksum = "4fc6ddaf24947d12a9aa31ac65431fb1b851b8f4365426e182901eabfb87df5f"
 dependencies = [
- "once_cell",
  "target-lexicon",
 ]
 
 [[package]]
 name = "pyo3-ffi"
-version = "0.25.1"
+version = "0.26.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "7114fe5457c61b276ab77c5055f206295b812608083644a5c5b2640c3102565c"
+checksum = "025474d3928738efb38ac36d4744a74a400c901c7596199e20e45d98eb194105"
 dependencies = [
  "libc",
  "pyo3-build-config",
@@ -917,9 +851,9 @@ dependencies = [
 
 [[package]]
 name = "pyo3-log"
-version = "0.12.4"
+version = "0.13.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "45192e5e4a4d2505587e27806c7b710c231c40c56f3bfc19535d0bb25df52264"
+checksum = "d359e20231345f21a3b5b6aea7e73f4dc97e1712ef3bfe2d88997ac6a308d784"
 dependencies = [
  "arc-swap",
  "log",
@@ -928,9 +862,9 @@ dependencies = [
 
 [[package]]
 name = "pyo3-macros"
-version = "0.25.1"
+version = "0.26.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "a8725c0a622b374d6cb051d11a0983786448f7785336139c3c94f5aa6bef7e50"
+checksum = "2e64eb489f22fe1c95911b77c44cc41e7c19f3082fc81cce90f657cdc42ffded"
 dependencies = [
  "proc-macro2",
  "pyo3-macros-backend",
@@ -940,9 +874,9 @@ dependencies = [
 
 [[package]]
 name = "pyo3-macros-backend"
-version = "0.25.1"
+version = "0.26.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "4109984c22491085343c05b0dbc54ddc405c3cf7b4374fc533f5c3313a572ccc"
+checksum = "100246c0ecf400b475341b8455a9213344569af29a3c841d29270e53102e0fcf"
 dependencies = [
  "heck",
  "proc-macro2",
@@ -953,9 +887,9 @@ dependencies = [
 
 [[package]]
 name = "pythonize"
-version = "0.25.0"
+version = "0.26.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "597907139a488b22573158793aa7539df36ae863eba300c75f3a0d65fc475e27"
+checksum = "11e06e4cff9be2bbf2bddf28a486ae619172ea57e79787f856572878c62dcfe2"
 dependencies = [
  "pyo3",
  "serde",
@@ -1062,9 +996,9 @@ dependencies = [
 
 [[package]]
 name = "regex"
-version = "1.11.3"
+version = "1.12.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "8b5288124840bee7b386bc413c487869b360b2b4ec421ea56425128692f2a82c"
+checksum = "843bc0191f75f3e22651ae5f1e72939ab2f72a4bc30fa80a066bd66edefc24d4"
 dependencies = [
  "aho-corasick",
  "memchr",
@@ -1074,9 +1008,9 @@ dependencies = [
 
 [[package]]
 name = "regex-automata"
-version = "0.4.11"
+version = "0.4.13"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "833eb9ce86d40ef33cb1306d8accf7bc8ec2bfea4355cbdebb3df68b40925cad"
+checksum = "5276caf25ac86c8d810222b3dbb938e512c55c6831a10f3e6ed1c93b84041f1c"
 dependencies = [
  "aho-corasick",
  "memchr",
@@ -1091,9 +1025,9 @@ checksum = "2b15c43186be67a4fd63bee50d0303afffcef381492ebe2c5d87f324e1b8815c"
 
 [[package]]
 name = "reqwest"
-version = "0.12.23"
+version = "0.12.24"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "d429f34c8092b2d42c7c93cec323bb4adeb7c67698f70839adec842ec10c7ceb"
+checksum = "9d0946410b9f7b082a427e4ef5c8ff541a88b357bc6c637c40db3a68ac70a36f"
 dependencies = [
  "base64",
  "bytes",
@@ -1145,12 +1079,6 @@ dependencies = [
  "windows-sys 0.52.0",
 ]
 
-[[package]]
-name = "rustc-demangle"
-version = "0.1.26"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "56f7d92ca342cea22a06f2121d944b4fd82af56988c270852495420f961d4ace"
-
 [[package]]
 name = "rustc-hash"
 version = "2.1.1"
@@ -1489,19 +1417,16 @@ checksum = "1f3ccbac311fea05f86f61904b462b55fb3df8837a366dfc601a0161d0532f20"
 
 [[package]]
 name = "tokio"
-version = "1.47.1"
+version = "1.48.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "89e49afdadebb872d3145a5638b59eb0691ea23e46ca484037cfab3b76b95038"
+checksum = "ff360e02eab121e0bc37a2d3b4d4dc622e6eda3a8e5253d5435ecf5bd4c68408"
 dependencies = [
- "backtrace",
  "bytes",
- "io-uring",
  "libc",
  "mio",
  "pin-project-lite",
- "slab",
  "socket2 0.6.0",
- "windows-sys 0.59.0",
+ "windows-sys 0.61.2",
 ]
 
 [[package]]
@@ -1782,6 +1707,12 @@ dependencies = [
  "wasm-bindgen",
 ]
 
+[[package]]
+name = "windows-link"
+version = "0.2.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "f0805222e57f7521d6a62e36fa9163bc891acd422f971defe97d64e70d0a4fe5"
+
 [[package]]
 name = "windows-sys"
 version = "0.52.0"
@@ -1800,6 +1731,15 @@ dependencies = [
  "windows-targets",
 ]
 
+[[package]]
+name = "windows-sys"
+version = "0.61.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "ae137229bcbd6cdf0f7b80a31df61766145077ddf49416a728b02cb3921ff3fc"
+dependencies = [
+ "windows-link",
+]
+
 [[package]]
 name = "windows-targets"
 version = "0.52.6"
diff --git a/build_rust.py b/build_rust.py
index 5c796af461..a9e9265daf 100644
--- a/build_rust.py
+++ b/build_rust.py
@@ -2,13 +2,13 @@
 
 import itertools
 import os
-from typing import Any, Dict
+from typing import Any
 
 from packaging.specifiers import SpecifierSet
 from setuptools_rust import Binding, RustExtension
 
 
-def build(setup_kwargs: Dict[str, Any]) -> None:
+def build(setup_kwargs: dict[str, Any]) -> None:
     original_project_dir = os.path.dirname(os.path.realpath(__file__))
     cargo_toml_path = os.path.join(original_project_dir, "rust", "Cargo.toml")
 
@@ -27,12 +27,12 @@ def build(setup_kwargs: Dict[str, Any]) -> None:
     setup_kwargs["zip_safe"] = False
 
     # We look up the minimum supported Python version with
-    # `python_requires` (e.g. ">=3.9.0,<4.0.0") and finding the first Python
+    # `python_requires` (e.g. ">=3.10.0,<4.0.0") and finding the first Python
     # version that matches. We then convert that into the `py_limited_api` form,
-    # e.g. cp39 for Python 3.9.
+    # e.g. cp310 for Python 3.10.
     py_limited_api: str
     python_bounds = SpecifierSet(setup_kwargs["python_requires"])
-    for minor_version in itertools.count(start=8):
+    for minor_version in itertools.count(start=10):
         if f"3.{minor_version}.0" in python_bounds:
             py_limited_api = f"cp3{minor_version}"
             break
diff --git a/changelog.d/18721.bugfix b/changelog.d/18721.bugfix
deleted file mode 100644
index 0aa0b3962d..0000000000
--- a/changelog.d/18721.bugfix
+++ /dev/null
@@ -1 +0,0 @@
-Fix room upgrade `room_config` argument and documentation for `user_may_create_room` spam-checker callback.
diff --git a/changelog.d/18767.misc b/changelog.d/18767.misc
deleted file mode 100644
index 5fa32a9f97..0000000000
--- a/changelog.d/18767.misc
+++ /dev/null
@@ -1 +0,0 @@
-Update OEmbed providers to use 'X' instead of 'Twitter' in URL previews, following a rebrand. Contributed by @HammyHavoc.
diff --git a/changelog.d/18868.misc b/changelog.d/18868.misc
deleted file mode 100644
index a9251f9da0..0000000000
--- a/changelog.d/18868.misc
+++ /dev/null
@@ -1 +0,0 @@
-Fix `server_name` in logging context for multiple Synapse instances in one process.
diff --git a/changelog.d/18911.feature b/changelog.d/18911.feature
deleted file mode 100644
index ac576e2913..0000000000
--- a/changelog.d/18911.feature
+++ /dev/null
@@ -1,2 +0,0 @@
-Add an Admin API that allows server admins to to query and investigate the metadata of local or cached remote media via
-the `origin/media_id` identifier found in a [Matrix Content URI](https://spec.matrix.org/v1.14/client-server-api/#matrix-content-mxc-uris).
\ No newline at end of file
diff --git a/changelog.d/18913.misc b/changelog.d/18913.misc
deleted file mode 100644
index e9093cb567..0000000000
--- a/changelog.d/18913.misc
+++ /dev/null
@@ -1 +0,0 @@
-Fix the GitHub Actions workflow that moves issues labeled "X-Needs-Info" to the "Needs info" column on the team's internal triage board.
\ No newline at end of file
diff --git a/changelog.d/18914.doc b/changelog.d/18914.doc
deleted file mode 100644
index 9d4f03ade7..0000000000
--- a/changelog.d/18914.doc
+++ /dev/null
@@ -1 +0,0 @@
-Explain how Deferred callbacks interact with logcontexts.
diff --git a/changelog.d/18932.misc b/changelog.d/18932.misc
deleted file mode 100644
index 675412ddb9..0000000000
--- a/changelog.d/18932.misc
+++ /dev/null
@@ -1 +0,0 @@
-Disconnect background process work from request trace.
diff --git a/changelog.d/18934.feature b/changelog.d/18934.feature
deleted file mode 100644
index e24b7a7e34..0000000000
--- a/changelog.d/18934.feature
+++ /dev/null
@@ -1 +0,0 @@
-Update [MSC4284: Policy Servers](https://github.com/matrix-org/matrix-spec-proposals/pull/4284) implementation to support signatures when available.
\ No newline at end of file
diff --git a/changelog.d/18939.misc b/changelog.d/18939.misc
deleted file mode 100644
index 6cfae2ceaf..0000000000
--- a/changelog.d/18939.misc
+++ /dev/null
@@ -1 +0,0 @@
-Reduce overall number of calls to `_get_e2e_cross_signing_signatures_for_devices` by increasing the batch size of devices the query is called with, reducing DB load.
diff --git a/changelog.d/18947.misc b/changelog.d/18947.misc
deleted file mode 100644
index 51c100b6dc..0000000000
--- a/changelog.d/18947.misc
+++ /dev/null
@@ -1 +0,0 @@
-Update error code used when an appservice tries to masquerade as an unknown device using [MSC4326](https://github.com/matrix-org/matrix-spec-proposals/pull/4326). Contributed by @tulir @ Beeper.
diff --git a/changelog.d/18948.bugfix b/changelog.d/18948.bugfix
deleted file mode 100644
index 7a8af0a286..0000000000
--- a/changelog.d/18948.bugfix
+++ /dev/null
@@ -1 +0,0 @@
-Compute a user's last seen timestamp from their devices' last seen timestamps instead of IPs, because the latter are automatically cleared according to `user_ips_max_age`.
diff --git a/changelog.d/18959.misc b/changelog.d/18959.misc
deleted file mode 100644
index e97475eec2..0000000000
--- a/changelog.d/18959.misc
+++ /dev/null
@@ -1 +0,0 @@
-Fix `no active span when trying to log` tracing error on startup (when OpenTracing is enabled).
diff --git a/changelog.d/18964.misc b/changelog.d/18964.misc
deleted file mode 100644
index 69be53ad27..0000000000
--- a/changelog.d/18964.misc
+++ /dev/null
@@ -1 +0,0 @@
-Fix `run_coroutine_in_background(...)` incorrectly handling logcontext.
diff --git a/changelog.d/18971.misc b/changelog.d/18971.misc
deleted file mode 100644
index 2d417d1319..0000000000
--- a/changelog.d/18971.misc
+++ /dev/null
@@ -1 +0,0 @@
-Update dockerfile metadata to fix broken link; point to documentation website.
\ No newline at end of file
diff --git a/changelog.d/18973.misc b/changelog.d/18973.misc
deleted file mode 100644
index e88fd74795..0000000000
--- a/changelog.d/18973.misc
+++ /dev/null
@@ -1 +0,0 @@
-Note that the code is additionally licensed under the [Element Commercial license](https://github.com/element-hq/synapse/blob/develop/LICENSE-COMMERCIAL) in SPDX expression field configs.
\ No newline at end of file
diff --git a/changelog.d/18974.misc b/changelog.d/18974.misc
deleted file mode 100644
index ca300a17a5..0000000000
--- a/changelog.d/18974.misc
+++ /dev/null
@@ -1 +0,0 @@
-Fix logcontext handling in `timeout_deferred` tests.
diff --git a/changelog.d/18988.misc b/changelog.d/18988.misc
deleted file mode 100644
index 14dbe92812..0000000000
--- a/changelog.d/18988.misc
+++ /dev/null
@@ -1 +0,0 @@
-Remove internal `ReplicationUploadKeysForUserRestServlet` as a follow-up to the work in https://github.com/element-hq/synapse/pull/18581 that moved device changes off the main process.
\ No newline at end of file
diff --git a/changelog.d/19111.misc b/changelog.d/19111.misc
new file mode 100644
index 0000000000..cb4ca85c47
--- /dev/null
+++ b/changelog.d/19111.misc
@@ -0,0 +1 @@
+Write union types as `X | Y` where possible, as per PEP 604, added in Python 3.10.
diff --git a/changelog.d/19138.misc b/changelog.d/19138.misc
new file mode 100644
index 0000000000..1183361737
--- /dev/null
+++ b/changelog.d/19138.misc
@@ -0,0 +1 @@
+Minor speed up of processing of inbound replication.
diff --git a/changelog.d/19145.misc b/changelog.d/19145.misc
new file mode 100644
index 0000000000..1183361737
--- /dev/null
+++ b/changelog.d/19145.misc
@@ -0,0 +1 @@
+Minor speed up of processing of inbound replication.
diff --git a/changelog.d/19146.misc b/changelog.d/19146.misc
new file mode 100644
index 0000000000..1183361737
--- /dev/null
+++ b/changelog.d/19146.misc
@@ -0,0 +1 @@
+Minor speed up of processing of inbound replication.
diff --git a/contrib/cmdclient/console.py b/contrib/cmdclient/console.py
index 9b5d33d2b1..1c867d5336 100755
--- a/contrib/cmdclient/console.py
+++ b/contrib/cmdclient/console.py
@@ -33,7 +33,6 @@ import sys
 import time
 import urllib
 from http import TwistedHttpClient
-from typing import Optional
 
 import urlparse
 from signedjson.key import NACL_ED25519, decode_verify_key_bytes
@@ -726,7 +725,7 @@ class SynapseCmd(cmd.Cmd):
         method,
         path,
         data=None,
-        query_params: Optional[dict] = None,
+        query_params: dict | None = None,
         alt_text=None,
     ):
         """Runs an HTTP request and pretty prints the output.
diff --git a/contrib/cmdclient/http.py b/contrib/cmdclient/http.py
index 54363e4259..b92ccdd932 100644
--- a/contrib/cmdclient/http.py
+++ b/contrib/cmdclient/http.py
@@ -22,7 +22,6 @@
 import json
 import urllib
 from pprint import pformat
-from typing import Optional
 
 from twisted.internet import defer, reactor
 from twisted.web.client import Agent, readBody
@@ -90,7 +89,7 @@ class TwistedHttpClient(HttpClient):
         body = yield readBody(response)
         return json.loads(body)
 
-    def _create_put_request(self, url, json_data, headers_dict: Optional[dict] = None):
+    def _create_put_request(self, url, json_data, headers_dict: dict | None = None):
         """Wrapper of _create_request to issue a PUT request"""
         headers_dict = headers_dict or {}
 
@@ -101,7 +100,7 @@ class TwistedHttpClient(HttpClient):
             "PUT", url, producer=_JsonProducer(json_data), headers_dict=headers_dict
         )
 
-    def _create_get_request(self, url, headers_dict: Optional[dict] = None):
+    def _create_get_request(self, url, headers_dict: dict | None = None):
         """Wrapper of _create_request to issue a GET request"""
         return self._create_request("GET", url, headers_dict=headers_dict or {})
 
@@ -113,7 +112,7 @@ class TwistedHttpClient(HttpClient):
         data=None,
         qparams=None,
         jsonreq=True,
-        headers: Optional[dict] = None,
+        headers: dict | None = None,
     ):
         headers = headers or {}
 
@@ -138,7 +137,7 @@ class TwistedHttpClient(HttpClient):
 
     @defer.inlineCallbacks
     def _create_request(
-        self, method, url, producer=None, headers_dict: Optional[dict] = None
+        self, method, url, producer=None, headers_dict: dict | None = None
     ):
         """Creates and sends a request to the given url"""
         headers_dict = headers_dict or {}
diff --git a/contrib/graph/graph.py b/contrib/graph/graph.py
index 9d5f3c7f4f..2898bb3448 100644
--- a/contrib/graph/graph.py
+++ b/contrib/graph/graph.py
@@ -24,7 +24,6 @@ import datetime
 import html
 import json
 import urllib.request
-from typing import List
 
 import pydot
 
@@ -33,7 +32,7 @@ def make_name(pdu_id: str, origin: str) -> str:
     return f"{pdu_id}@{origin}"
 
 
-def make_graph(pdus: List[dict], filename_prefix: str) -> None:
+def make_graph(pdus: list[dict], filename_prefix: str) -> None:
     """
     Generate a dot and SVG file for a graph of events in the room based on the
     topological ordering by querying a homeserver.
@@ -127,7 +126,7 @@ def make_graph(pdus: List[dict], filename_prefix: str) -> None:
     graph.write_svg("%s.svg" % filename_prefix, prog="dot")
 
 
-def get_pdus(host: str, room: str) -> List[dict]:
+def get_pdus(host: str, room: str) -> list[dict]:
     transaction = json.loads(
         urllib.request.urlopen(
             f"http://{host}/_matrix/federation/v1/context/{room}/"
diff --git a/debian/changelog b/debian/changelog
index 6c476674f9..6531a59569 100644
--- a/debian/changelog
+++ b/debian/changelog
@@ -1,4 +1,94 @@
-matrix-synapse-py3 (1.139.0~rc3+nmu1) UNRELEASED; urgency=medium
+matrix-synapse-py3 (1.142.0~rc4) stable; urgency=medium
+
+  * New Synapse release 1.142.0rc4.
+
+ -- Synapse Packaging team <packages@matrix.org>  Fri, 07 Nov 2025 10:54:42 +0000
+
+matrix-synapse-py3 (1.142.0~rc3) stable; urgency=medium
+
+  * New Synapse release 1.142.0rc3.
+
+ -- Synapse Packaging team <packages@matrix.org>  Tue, 04 Nov 2025 17:39:11 +0000
+
+matrix-synapse-py3 (1.142.0~rc2) stable; urgency=medium
+
+  * New Synapse release 1.142.0rc2.
+
+ -- Synapse Packaging team <packages@matrix.org>  Tue, 04 Nov 2025 16:21:30 +0000
+
+matrix-synapse-py3 (1.142.0~rc1) stable; urgency=medium
+
+  * New Synapse release 1.142.0rc1.
+
+ -- Synapse Packaging team <packages@matrix.org>  Tue, 04 Nov 2025 13:20:15 +0000
+
+matrix-synapse-py3 (1.141.0) stable; urgency=medium
+
+  * New Synapse release 1.141.0.
+
+ -- Synapse Packaging team <packages@matrix.org>  Wed, 29 Oct 2025 11:01:43 +0000
+
+matrix-synapse-py3 (1.141.0~rc2) stable; urgency=medium
+
+  * New Synapse release 1.141.0rc2.
+
+ -- Synapse Packaging team <packages@matrix.org>  Tue, 28 Oct 2025 10:20:26 +0000
+
+matrix-synapse-py3 (1.141.0~rc1) stable; urgency=medium
+
+  * New Synapse release 1.141.0rc1.
+
+ -- Synapse Packaging team <packages@matrix.org>  Tue, 21 Oct 2025 11:01:44 +0100
+
+matrix-synapse-py3 (1.140.0) stable; urgency=medium
+
+  * New Synapse release 1.140.0.
+
+ -- Synapse Packaging team <packages@matrix.org>  Tue, 14 Oct 2025 15:22:36 +0100
+
+matrix-synapse-py3 (1.140.0~rc1) stable; urgency=medium
+
+  * New Synapse release 1.140.0rc1.
+
+ -- Synapse Packaging team <packages@matrix.org>  Fri, 10 Oct 2025 10:56:51 +0100
+
+matrix-synapse-py3 (1.139.2) stable; urgency=medium
+
+  * New Synapse release 1.139.2.
+
+ -- Synapse Packaging team <packages@matrix.org>  Tue, 07 Oct 2025 16:29:47 +0100
+
+matrix-synapse-py3 (1.139.1) stable; urgency=medium
+
+  * New Synapse release 1.139.1.
+
+ -- Synapse Packaging team <packages@matrix.org>  Tue, 07 Oct 2025 11:46:51 +0100
+
+matrix-synapse-py3 (1.138.4) stable; urgency=medium
+
+  * New Synapse release 1.138.4.
+
+ -- Synapse Packaging team <packages@matrix.org>  Tue, 07 Oct 2025 16:28:38 +0100
+
+matrix-synapse-py3 (1.138.3) stable; urgency=medium
+
+  * New Synapse release 1.138.3.
+
+ -- Synapse Packaging team <packages@matrix.org>  Tue, 07 Oct 2025 12:54:18 +0100
+
+matrix-synapse-py3 (1.139.0) stable; urgency=medium
+
+  * New Synapse release 1.139.0.
+
+ -- Synapse Packaging team <packages@matrix.org>  Tue, 30 Sep 2025 11:58:55 +0100
+
+matrix-synapse-py3 (1.139.0~rc3) stable; urgency=medium
+
+  * New Synapse release 1.139.0rc3.
+
+ -- Synapse Packaging team <packages@matrix.org>  Thu, 25 Sep 2025 12:13:23 +0100
+
+matrix-synapse-py3 (1.138.2) stable; urgency=medium
 
   * The licensing specifier has been updated to add an optional
     `LicenseRef-Element-Commercial` license. The code was already licensed in
@@ -6,11 +96,11 @@ matrix-synapse-py3 (1.139.0~rc3+nmu1) UNRELEASED; urgency=medium
 
  -- Synapse Packaging team <packages@matrix.org>  Thu, 25 Sep 2025 12:17:17 +0100
 
-matrix-synapse-py3 (1.139.0~rc3) stable; urgency=medium
+matrix-synapse-py3 (1.138.1) stable; urgency=medium
 
-  * New Synapse release 1.139.0rc3.
+  * New Synapse release 1.138.1.
 
- -- Synapse Packaging team <packages@matrix.org>  Thu, 25 Sep 2025 12:13:23 +0100
+ -- Synapse Packaging team <packages@matrix.org>  Wed, 24 Sep 2025 11:32:38 +0100
 
 matrix-synapse-py3 (1.139.0~rc2) stable; urgency=medium
 
@@ -24,24 +114,6 @@ matrix-synapse-py3 (1.139.0~rc1) stable; urgency=medium
 
  -- Synapse Packaging team <packages@matrix.org>  Tue, 23 Sep 2025 13:24:50 +0100
 
-matrix-synapse-py3 (1.138.2) stable; urgency=medium
-
-  * New Synapse release 1.138.2.
-
- -- Synapse Packaging team <packages@matrix.org>  Wed, 24 Sep 2025 12:26:16 +0100
-
-matrix-synapse-py3 (1.138.1) stable; urgency=medium
-
-  * New Synapse release 1.138.1.
-
- -- Synapse Packaging team <packages@matrix.org>  Wed, 24 Sep 2025 11:32:38 +0100
-
-matrix-synapse-py3 (1.138.0) stable; urgency=medium
-
-  * New Synapse release 1.138.0.
-
- -- Synapse Packaging team <packages@matrix.org>  Tue, 09 Sep 2025 11:21:25 +0100
-
 matrix-synapse-py3 (1.138.0~rc1) stable; urgency=medium
 
   * New synapse release 1.138.0rc1.
diff --git a/docker/Dockerfile b/docker/Dockerfile
index 727bc8bf5d..6d10dee1aa 100644
--- a/docker/Dockerfile
+++ b/docker/Dockerfile
@@ -20,8 +20,8 @@
 # `poetry export | pip install -r /dev/stdin`, but beware: we have experienced bugs in
 # in `poetry export` in the past.
 
-ARG DEBIAN_VERSION=bookworm
-ARG PYTHON_VERSION=3.12
+ARG DEBIAN_VERSION=trixie
+ARG PYTHON_VERSION=3.13
 ARG POETRY_VERSION=2.1.1
 
 ###
@@ -142,10 +142,10 @@ RUN \
       libwebp7 \
       xmlsec1 \
       libjemalloc2 \
-      libicu \
     | grep '^\w' > /tmp/pkg-list && \
   for arch in arm64 amd64; do \
     mkdir -p /tmp/debs-${arch} && \
+    chown _apt:root /tmp/debs-${arch} && \
     cd /tmp/debs-${arch} && \
     apt-get -o APT::Architecture="${arch}" download $(cat /tmp/pkg-list); \
   done
@@ -176,15 +176,15 @@ LABEL org.opencontainers.image.documentation='https://element-hq.github.io/synap
 LABEL org.opencontainers.image.source='https://github.com/element-hq/synapse.git'
 LABEL org.opencontainers.image.licenses='AGPL-3.0-or-later OR LicenseRef-Element-Commercial'
 
-# On the runtime image, /lib is a symlink to /usr/lib, so we need to copy the
-# libraries to the right place, else the `COPY` won't work.
-# On amd64, we'll also have a /lib64 folder with ld-linux-x86-64.so.2, which is
-# already present in the runtime image.
-COPY --from=runtime-deps /install-${TARGETARCH}/lib /usr/lib
 COPY --from=runtime-deps /install-${TARGETARCH}/etc /etc
 COPY --from=runtime-deps /install-${TARGETARCH}/usr /usr
 COPY --from=runtime-deps /install-${TARGETARCH}/var /var
-COPY --from=builder /install /usr/local
+
+# Copy the installed python packages from the builder stage.
+#
+# uv will generate a `.lock` file when installing packages, which we don't want
+# to copy to the final image.
+COPY --from=builder  --exclude=.lock /install /usr/local
 COPY ./docker/start.py /start.py
 COPY ./docker/conf /conf
 
diff --git a/docker/Dockerfile-workers b/docker/Dockerfile-workers
index 6d0fc1440b..ba8bb3b753 100644
--- a/docker/Dockerfile-workers
+++ b/docker/Dockerfile-workers
@@ -1,9 +1,10 @@
-# syntax=docker/dockerfile:1
+# syntax=docker/dockerfile:1-labs
 
 ARG SYNAPSE_VERSION=latest
 ARG FROM=matrixdotorg/synapse:$SYNAPSE_VERSION
-ARG DEBIAN_VERSION=bookworm
-ARG PYTHON_VERSION=3.12
+ARG DEBIAN_VERSION=trixie
+ARG PYTHON_VERSION=3.13
+ARG REDIS_VERSION=7.2
 
 # first of all, we create a base image with dependencies which we can copy into the
 # target image. For repeated rebuilds, this is much faster than apt installing
@@ -11,15 +12,27 @@ ARG PYTHON_VERSION=3.12
 
 FROM ghcr.io/astral-sh/uv:python${PYTHON_VERSION}-${DEBIAN_VERSION} AS deps_base
 
+    ARG DEBIAN_VERSION
+    ARG REDIS_VERSION
+
     # Tell apt to keep downloaded package files, as we're using cache mounts.
     RUN rm -f /etc/apt/apt.conf.d/docker-clean; echo 'Binary::apt::APT::Keep-Downloaded-Packages "true";' > /etc/apt/apt.conf.d/keep-cache
 
+    # The upstream redis-server deb has fewer dynamic libraries than Debian's package which makes it easier to copy later on
+    RUN \
+      curl -fsSL https://packages.redis.io/gpg | gpg --dearmor -o /usr/share/keyrings/redis-archive-keyring.gpg && \
+      chmod 644 /usr/share/keyrings/redis-archive-keyring.gpg && \
+      echo "deb [signed-by=/usr/share/keyrings/redis-archive-keyring.gpg] https://packages.redis.io/deb ${DEBIAN_VERSION} main" | tee /etc/apt/sources.list.d/redis.list
+
     RUN \
        --mount=type=cache,target=/var/cache/apt,sharing=locked \
        --mount=type=cache,target=/var/lib/apt,sharing=locked \
       apt-get update -qq && \
       DEBIAN_FRONTEND=noninteractive apt-get install -yqq --no-install-recommends \
-          nginx-light
+          nginx-light \
+          redis-server="6:${REDIS_VERSION}.*" redis-tools="6:${REDIS_VERSION}.*" \
+          # libicu is required by postgres, see `docker/complement/Dockerfile`
+          libicu76
 
     RUN \
     # remove default page
@@ -35,19 +48,12 @@ FROM ghcr.io/astral-sh/uv:python${PYTHON_VERSION}-${DEBIAN_VERSION} AS deps_base
 
     RUN mkdir -p /uv/etc/supervisor/conf.d
 
-# Similarly, a base to copy the redis server from.
-#
-# The redis docker image has fewer dynamic libraries than the debian package,
-# which makes it much easier to copy (but we need to make sure we use an image
-# based on the same debian version as the synapse image, to make sure we get
-# the expected version of libc.
-FROM docker.io/library/redis:7-${DEBIAN_VERSION} AS redis_base
-
 # now build the final image, based on the the regular Synapse docker image
 FROM $FROM
 
     # Copy over dependencies
-    COPY --from=redis_base /usr/local/bin/redis-server /usr/local/bin
+    COPY --from=deps_base --parents /usr/lib/*-linux-gnu/libicu* /
+    COPY --from=deps_base /usr/bin/redis-server /usr/local/bin
     COPY --from=deps_base /uv /
     COPY --from=deps_base /usr/sbin/nginx /usr/sbin
     COPY --from=deps_base /usr/share/nginx /usr/share/nginx
diff --git a/docker/complement/Dockerfile b/docker/complement/Dockerfile
index 6ed084fe5d..8766f14454 100644
--- a/docker/complement/Dockerfile
+++ b/docker/complement/Dockerfile
@@ -9,7 +9,7 @@
 ARG SYNAPSE_VERSION=latest
 # This is an intermediate image, to be built locally (not pulled from a registry).
 ARG FROM=matrixdotorg/synapse-workers:$SYNAPSE_VERSION
-ARG DEBIAN_VERSION=bookworm
+ARG DEBIAN_VERSION=trixie
 
 FROM docker.io/library/postgres:13-${DEBIAN_VERSION} AS postgres_base
 
@@ -18,10 +18,10 @@ FROM $FROM
 # since for repeated rebuilds, this is much faster than apt installing
 # postgres each time.
 
-# This trick only works because (a) the Synapse image happens to have all the
-# shared libraries that postgres wants, (b) we use a postgres image based on
-# the same debian version as Synapse's docker image (so the versions of the
-# shared libraries match).
+# This trick only works because we use a postgres image based on the same
+# debian version as Synapse's docker image (so the versions of the shared
+# libraries match). Any missing libraries need to be added to either the
+# Synapse image or docker/Dockerfile-workers.
 RUN adduser --system --uid 999 postgres --home /var/lib/postgresql
 COPY --from=postgres_base /usr/lib/postgresql /usr/lib/postgresql
 COPY --from=postgres_base /usr/share/postgresql /usr/share/postgresql
diff --git a/docker/configure_workers_and_start.py b/docker/configure_workers_and_start.py
index 6f25653bb7..e19b0a0039 100755
--- a/docker/configure_workers_and_start.py
+++ b/docker/configure_workers_and_start.py
@@ -65,13 +65,9 @@ from itertools import chain
 from pathlib import Path
 from typing import (
     Any,
-    Dict,
-    List,
     Mapping,
     MutableMapping,
     NoReturn,
-    Optional,
-    Set,
     SupportsIndex,
 )
 
@@ -96,7 +92,7 @@ WORKER_PLACEHOLDER_NAME = "placeholder_name"
 # Watching /_matrix/media and related needs a "media" listener
 # Stream Writers require "client" and "replication" listeners because they
 #   have to attach by instance_map to the master process and have client endpoints.
-WORKERS_CONFIG: Dict[str, Dict[str, Any]] = {
+WORKERS_CONFIG: dict[str, dict[str, Any]] = {
     "pusher": {
         "app": "synapse.app.generic_worker",
         "listener_resources": [],
@@ -408,7 +404,7 @@ def convert(src: str, dst: str, **template_vars: object) -> None:
 
 def add_worker_roles_to_shared_config(
     shared_config: dict,
-    worker_types_set: Set[str],
+    worker_types_set: set[str],
     worker_name: str,
     worker_port: int,
 ) -> None:
@@ -471,9 +467,9 @@ def add_worker_roles_to_shared_config(
 
 
 def merge_worker_template_configs(
-    existing_dict: Optional[Dict[str, Any]],
-    to_be_merged_dict: Dict[str, Any],
-) -> Dict[str, Any]:
+    existing_dict: dict[str, Any] | None,
+    to_be_merged_dict: dict[str, Any],
+) -> dict[str, Any]:
     """When given an existing dict of worker template configuration consisting with both
         dicts and lists, merge new template data from WORKERS_CONFIG(or create) and
         return new dict.
@@ -484,7 +480,7 @@ def merge_worker_template_configs(
             existing_dict.
     Returns: The newly merged together dict values.
     """
-    new_dict: Dict[str, Any] = {}
+    new_dict: dict[str, Any] = {}
     if not existing_dict:
         # It doesn't exist yet, just use the new dict(but take a copy not a reference)
         new_dict = to_be_merged_dict.copy()
@@ -509,8 +505,8 @@ def merge_worker_template_configs(
 
 
 def insert_worker_name_for_worker_config(
-    existing_dict: Dict[str, Any], worker_name: str
-) -> Dict[str, Any]:
+    existing_dict: dict[str, Any], worker_name: str
+) -> dict[str, Any]:
     """Insert a given worker name into the worker's configuration dict.
 
     Args:
@@ -526,7 +522,7 @@ def insert_worker_name_for_worker_config(
     return dict_to_edit
 
 
-def apply_requested_multiplier_for_worker(worker_types: List[str]) -> List[str]:
+def apply_requested_multiplier_for_worker(worker_types: list[str]) -> list[str]:
     """
     Apply multiplier(if found) by returning a new expanded list with some basic error
     checking.
@@ -587,7 +583,7 @@ def is_sharding_allowed_for_worker_type(worker_type: str) -> bool:
 
 def split_and_strip_string(
     given_string: str, split_char: str, max_split: SupportsIndex = -1
-) -> List[str]:
+) -> list[str]:
     """
     Helper to split a string on split_char and strip whitespace from each end of each
         element.
@@ -616,8 +612,8 @@ def generate_base_homeserver_config() -> None:
 
 
 def parse_worker_types(
-    requested_worker_types: List[str],
-) -> Dict[str, Set[str]]:
+    requested_worker_types: list[str],
+) -> dict[str, set[str]]:
     """Read the desired list of requested workers and prepare the data for use in
         generating worker config files while also checking for potential gotchas.
 
@@ -633,14 +629,14 @@ def parse_worker_types(
     # A counter of worker_base_name -> int. Used for determining the name for a given
     # worker when generating its config file, as each worker's name is just
     # worker_base_name followed by instance number
-    worker_base_name_counter: Dict[str, int] = defaultdict(int)
+    worker_base_name_counter: dict[str, int] = defaultdict(int)
 
     # Similar to above, but more finely grained. This is used to determine we don't have
     # more than a single worker for cases where multiples would be bad(e.g. presence).
-    worker_type_shard_counter: Dict[str, int] = defaultdict(int)
+    worker_type_shard_counter: dict[str, int] = defaultdict(int)
 
     # The final result of all this processing
-    dict_to_return: Dict[str, Set[str]] = {}
+    dict_to_return: dict[str, set[str]] = {}
 
     # Handle any multipliers requested for given workers.
     multiple_processed_worker_types = apply_requested_multiplier_for_worker(
@@ -684,7 +680,7 @@ def parse_worker_types(
 
         # Split the worker_type_string on "+", remove whitespace from ends then make
         # the list a set so it's deduplicated.
-        worker_types_set: Set[str] = set(
+        worker_types_set: set[str] = set(
             split_and_strip_string(worker_type_string, "+")
         )
 
@@ -743,7 +739,7 @@ def generate_worker_files(
     environ: Mapping[str, str],
     config_path: str,
     data_dir: str,
-    requested_worker_types: Dict[str, Set[str]],
+    requested_worker_types: dict[str, set[str]],
 ) -> None:
     """Read the desired workers(if any) that is passed in and generate shared
         homeserver, nginx and supervisord configs.
@@ -764,7 +760,7 @@ def generate_worker_files(
     # First read the original config file and extract the listeners block. Then we'll
     # add another listener for replication. Later we'll write out the result to the
     # shared config file.
-    listeners: List[Any]
+    listeners: list[Any]
     if using_unix_sockets:
         listeners = [
             {
@@ -792,12 +788,12 @@ def generate_worker_files(
     # base shared worker jinja2 template. This config file will be passed to all
     # workers, included Synapse's main process. It is intended mainly for disabling
     # functionality when certain workers are spun up, and adding a replication listener.
-    shared_config: Dict[str, Any] = {"listeners": listeners}
+    shared_config: dict[str, Any] = {"listeners": listeners}
 
     # List of dicts that describe workers.
     # We pass this to the Supervisor template later to generate the appropriate
     # program blocks.
-    worker_descriptors: List[Dict[str, Any]] = []
+    worker_descriptors: list[dict[str, Any]] = []
 
     # Upstreams for load-balancing purposes. This dict takes the form of the worker
     # type to the ports of each worker. For example:
@@ -805,14 +801,14 @@ def generate_worker_files(
     #   worker_type: {1234, 1235, ...}}
     # }
     # and will be used to construct 'upstream' nginx directives.
-    nginx_upstreams: Dict[str, Set[int]] = {}
+    nginx_upstreams: dict[str, set[int]] = {}
 
     # A map of: {"endpoint": "upstream"}, where "upstream" is a str representing what
     # will be placed after the proxy_pass directive. The main benefit to representing
     # this data as a dict over a str is that we can easily deduplicate endpoints
     # across multiple instances of the same worker. The final rendering will be combined
     # with nginx_upstreams and placed in /etc/nginx/conf.d.
-    nginx_locations: Dict[str, str] = {}
+    nginx_locations: dict[str, str] = {}
 
     # Create the worker configuration directory if it doesn't already exist
     os.makedirs("/conf/workers", exist_ok=True)
@@ -846,7 +842,7 @@ def generate_worker_files(
     # yaml config file
     for worker_name, worker_types_set in requested_worker_types.items():
         # The collected and processed data will live here.
-        worker_config: Dict[str, Any] = {}
+        worker_config: dict[str, Any] = {}
 
         # Merge all worker config templates for this worker into a single config
         for worker_type in worker_types_set:
@@ -1029,7 +1025,7 @@ def generate_worker_log_config(
     Returns: the path to the generated file
     """
     # Check whether we should write worker logs to disk, in addition to the console
-    extra_log_template_args: Dict[str, Optional[str]] = {}
+    extra_log_template_args: dict[str, str | None] = {}
     if environ.get("SYNAPSE_WORKERS_WRITE_LOGS_TO_DISK"):
         extra_log_template_args["LOG_FILE_PATH"] = f"{data_dir}/logs/{worker_name}.log"
 
@@ -1053,7 +1049,7 @@ def generate_worker_log_config(
     return log_config_filepath
 
 
-def main(args: List[str], environ: MutableMapping[str, str]) -> None:
+def main(args: list[str], environ: MutableMapping[str, str]) -> None:
     parser = ArgumentParser()
     parser.add_argument(
         "--generate-only",
@@ -1087,7 +1083,7 @@ def main(args: List[str], environ: MutableMapping[str, str]) -> None:
         if not worker_types_env:
             # No workers, just the main process
             worker_types = []
-            requested_worker_types: Dict[str, Any] = {}
+            requested_worker_types: dict[str, Any] = {}
         else:
             # Split type names by comma, ignoring whitespace.
             worker_types = split_and_strip_string(worker_types_env, ",")
diff --git a/docker/editable.Dockerfile b/docker/editable.Dockerfile
index f18cf6a5d9..b2aff9cb53 100644
--- a/docker/editable.Dockerfile
+++ b/docker/editable.Dockerfile
@@ -3,14 +3,14 @@
 #
 # Used by `complement.sh`. Not suitable for production use.
 
-ARG PYTHON_VERSION=3.9
+ARG PYTHON_VERSION=3.10
 
 ###
 ### Stage 0: generate requirements.txt
 ###
-# We hardcode the use of Debian bookworm here because this could change upstream
-# and other Dockerfiles used for testing are expecting bookworm.
-FROM docker.io/library/python:${PYTHON_VERSION}-slim-bookworm
+# We hardcode the use of Debian trixie here because this could change upstream
+# and other Dockerfiles used for testing are expecting trixie.
+FROM docker.io/library/python:${PYTHON_VERSION}-slim-trixie
 
 # Install Rust and other dependencies (stolen from normal Dockerfile)
 # install the OS build deps
diff --git a/docker/start.py b/docker/start.py
index 0be9976a0c..c88d23695f 100755
--- a/docker/start.py
+++ b/docker/start.py
@@ -6,7 +6,7 @@ import os
 import platform
 import subprocess
 import sys
-from typing import Any, Dict, List, Mapping, MutableMapping, NoReturn, Optional
+from typing import Any, Mapping, MutableMapping, NoReturn
 
 import jinja2
 
@@ -50,7 +50,7 @@ def generate_config_from_template(
     config_dir: str,
     config_path: str,
     os_environ: Mapping[str, str],
-    ownership: Optional[str],
+    ownership: str | None,
 ) -> None:
     """Generate a homeserver.yaml from environment variables
 
@@ -69,7 +69,7 @@ def generate_config_from_template(
             )
 
     # populate some params from data files (if they exist, else create new ones)
-    environ: Dict[str, Any] = dict(os_environ)
+    environ: dict[str, Any] = dict(os_environ)
     secrets = {
         "registration": "SYNAPSE_REGISTRATION_SHARED_SECRET",
         "macaroon": "SYNAPSE_MACAROON_SECRET_KEY",
@@ -147,7 +147,7 @@ def generate_config_from_template(
     subprocess.run(args, check=True)
 
 
-def run_generate_config(environ: Mapping[str, str], ownership: Optional[str]) -> None:
+def run_generate_config(environ: Mapping[str, str], ownership: str | None) -> None:
     """Run synapse with a --generate-config param to generate a template config file
 
     Args:
@@ -200,7 +200,7 @@ def run_generate_config(environ: Mapping[str, str], ownership: Optional[str]) ->
     subprocess.run(args, check=True)
 
 
-def main(args: List[str], environ: MutableMapping[str, str]) -> None:
+def main(args: list[str], environ: MutableMapping[str, str]) -> None:
     mode = args[1] if len(args) > 1 else "run"
 
     # if we were given an explicit user to switch to, do so
diff --git a/docs/SUMMARY.md b/docs/SUMMARY.md
index 52f827c8df..926a6eb848 100644
--- a/docs/SUMMARY.md
+++ b/docs/SUMMARY.md
@@ -60,6 +60,7 @@
     - [Admin API](usage/administration/admin_api/README.md)
       - [Account Validity](admin_api/account_validity.md)
       - [Background Updates](usage/administration/admin_api/background_updates.md)
+      - [Fetch Event](admin_api/fetch_event.md)
       - [Event Reports](admin_api/event_reports.md)
       - [Experimental Features](admin_api/experimental_features.md)
       - [Media](admin_api/media_admin_api.md)
@@ -115,6 +116,8 @@
       - [The Auth Chain Difference Algorithm](auth_chain_difference_algorithm.md)
     - [Media Repository](media_repository.md)
     - [Room and User Statistics](room_and_user_statistics.md)
+    - [Releasing]()
+      - [Release Notes Review Checklist](development/internal_documentation/release_notes_review_checklist.md)
   - [Scripts]()
 
 # Other
diff --git a/docs/admin_api/fetch_event.md b/docs/admin_api/fetch_event.md
new file mode 100644
index 0000000000..baf45b8aa7
--- /dev/null
+++ b/docs/admin_api/fetch_event.md
@@ -0,0 +1,53 @@
+# Fetch Event API
+
+The fetch event API allows admins to fetch an event regardless of their membership in the room it
+originated in.
+
+To use it, you will need to authenticate by providing an `access_token`
+for a server admin: see [Admin API](../usage/administration/admin_api/).
+
+Request:
+```http
+GET /_synapse/admin/v1/fetch_event/<event_id>
+```
+
+The API returns a JSON body like the following:
+
+Response:
+```json
+{
+    "event": {
+        "auth_events": [
+            "$WhLChbYg6atHuFRP7cUd95naUtc8L0f7fqeizlsUVvc",
+            "$9Wj8dt02lrNEWweeq-KjRABUYKba0K9DL2liRvsAdtQ",
+            "$qJxBFxBt8_ODd9b3pgOL_jXP98S_igc1_kizuPSZFi4"
+        ],
+        "content": {
+            "body": "Hey now",
+            "msgtype": "m.text"
+        },
+        "depth": 6,
+        "event_id": "$hJ_kcXbVMcI82JDrbqfUJIHu61tJD86uIFJ_8hNHi7s",
+        "hashes": {
+            "sha256": "LiNw8DtrRVf55EgAH8R42Wz7WCJUqGsPt2We6qZO5Rg"
+        },
+        "origin_server_ts": 799,
+        "prev_events": [
+            "$cnSUrNMnC3Ywh9_W7EquFxYQjC_sT3BAAVzcUVxZq1g"
+        ],
+        "room_id": "!aIhKToCqgPTBloWMpf:test",
+        "sender": "@user:test",
+        "signatures": {
+            "test": {
+                "ed25519:a_lPym": "7mqSDwK1k7rnw34Dd8Fahu0rhPW7jPmcWPRtRDoEN9Yuv+BCM2+Rfdpv2MjxNKy3AYDEBwUwYEuaKMBaEMiKAQ"
+            }
+        },
+        "type": "m.room.message",
+        "unsigned": {
+            "age_ts": 799
+        }
+    }
+}
+```
+
+
diff --git a/docs/admin_api/rooms.md b/docs/admin_api/rooms.md
index 12af87148d..11e787c236 100644
--- a/docs/admin_api/rooms.md
+++ b/docs/admin_api/rooms.md
@@ -1115,3 +1115,76 @@ Example response:
   ]
 }
 ```
+
+# Admin Space Hierarchy Endpoint
+
+This API allows an admin to fetch the space/room hierarchy for a given space, 
+returning details about that room and any children the room may have, paginating
+over the space tree in a depth-first manner to locate child rooms. This is
+functionally similar to the [CS Hierarchy](https://spec.matrix.org/v1.16/client-server-api/#get_matrixclientv1roomsroomidhierarchy) endpoint but does not check for
+room membership when returning room summaries.
+
+The endpoint does not query other servers over federation about remote rooms
+that the server has not joined. This is a deliberate trade-off: while this
+means it will leave some holes in the hierarchy that we could otherwise
+sometimes fill in, it significantly improves the endpoint's response time and
+the admin endpoint is designed for managing rooms local to the homeserver
+anyway.
+
+**Parameters**
+
+The following query parameters are available:
+
+* `from` - An optional pagination token, provided when there are more rooms to 
+    return than the limit. 
+* `limit` - Maximum amount of rooms to return. Must be a non-negative integer,
+   defaults to `50`.
+* `max_depth` - The maximum depth in the tree to explore, must be a non-negative
+   integer. 0 would correspond to just the root room, 1 would include just the
+   root room's children, etc.  If not provided will recurse into the space tree without limit.
+
+Request:
+
+```http
+GET /_synapse/admin/v1/rooms/<room_id>/hierarchy
+```
+
+Response:
+
+```json
+{
+  "rooms":
+      [
+        { "children_state": [
+            {
+              "content": {
+                "via": ["local_test_server"]
+              },
+              "origin_server_ts": 1500,
+              "sender": "@user:test",
+              "state_key": "!QrMkkqBSwYRIFNFCso:test",
+              "type": "m.space.child"
+            }
+        ],
+        "name": "space room",
+        "guest_can_join": false,
+        "join_rule": "public",
+        "num_joined_members": 1,
+        "room_id": "!sPOpNyMHbZAoAOsOFL:test",
+        "room_type": "m.space",
+        "world_readable": false
+      },
+
+      {
+        "children_state": [],
+        "guest_can_join": true,
+        "join_rule": "invite",
+        "name": "nefarious",
+        "num_joined_members": 1,
+        "room_id": "!QrMkkqBSwYRIFNFCso:test",
+        "topic": "being bad",
+        "world_readable": false}
+    ],
+  "next_batch": "KUYmRbeSpAoaAIgOKGgyaCEn"
+}
+```
diff --git a/docs/deprecation_policy.md b/docs/deprecation_policy.md
index 2f3a09723e..06c724d348 100644
--- a/docs/deprecation_policy.md
+++ b/docs/deprecation_policy.md
@@ -21,7 +21,7 @@ people building from source should ensure they can fetch recent versions of Rust
 (e.g. by using [rustup](https://rustup.rs/)).
 
 The oldest supported version of SQLite is the version
-[provided](https://packages.debian.org/bullseye/libsqlite3-0) by
+[provided](https://packages.debian.org/oldstable/libsqlite3-0) by
 [Debian oldstable](https://wiki.debian.org/DebianOldStable).
 
 
diff --git a/docs/development/contributing_guide.md b/docs/development/contributing_guide.md
index eb6f04e301..41fff1d6a3 100644
--- a/docs/development/contributing_guide.md
+++ b/docs/development/contributing_guide.md
@@ -320,7 +320,7 @@ The following command will let you run the integration test with the most common
 configuration:
 
 ```sh
-$ docker run --rm -it -v /path/where/you/have/cloned/the/repository\:/src:ro -v /path/to/where/you/want/logs\:/logs matrixdotorg/sytest-synapse:bullseye
+$ docker run --rm -it -v /path/where/you/have/cloned/the/repository\:/src:ro -v /path/to/where/you/want/logs\:/logs matrixdotorg/sytest-synapse:bookworm
 ```
 (Note that the paths must be full paths! You could also write `$(realpath relative/path)` if needed.)
 
diff --git a/docs/development/dependencies.md b/docs/development/dependencies.md
index e381b3d155..1b3348703f 100644
--- a/docs/development/dependencies.md
+++ b/docs/development/dependencies.md
@@ -79,17 +79,17 @@ phonenumbers = [
 We can see this pinned version inside the docker image for that release:
 
 ```
-$ docker pull vectorim/synapse:v1.97.0
+$ docker pull matrixdotorg/synapse:latest
 ...
-$ docker run --entrypoint pip vectorim/synapse:v1.97.0 show phonenumbers
+$ docker run --entrypoint pip matrixdotorg/synapse:latest show phonenumbers
 Name: phonenumbers
-Version: 8.12.44
+Version: 9.0.15
 Summary: Python version of Google's common library for parsing, formatting, storing and validating international phone numbers.
 Home-page: https://github.com/daviddrysdale/python-phonenumbers
 Author: David Drysdale
 Author-email: dmd@lurklurk.org
 License: Apache License 2.0
-Location: /usr/local/lib/python3.9/site-packages
+Location: /usr/local/lib/python3.12/site-packages
 Requires:
 Required-by: matrix-synapse
 ```
diff --git a/docs/development/internal_documentation/release_notes_review_checklist.md b/docs/development/internal_documentation/release_notes_review_checklist.md
new file mode 100644
index 0000000000..c3d4d665be
--- /dev/null
+++ b/docs/development/internal_documentation/release_notes_review_checklist.md
@@ -0,0 +1,12 @@
+# Release notes review checklist
+
+The Synapse release process includes a step to review the changelog before
+publishing it. The following is a list of common points to check for:
+
+1. Check whether any similar entries that can be merged together (make sure to include all mentioned PRs at the end of the line, i.e. (#1234, #1235, ...)).
+2. Link any MSCXXXX lines to the Matrix Spec Change itself: <https://github.com/matrix-org/matrix-spec-proposals/pull/xxxx>.
+3. Wrap any class names, variable names, etc. in back-ticks, if needed.
+4. Hoist any relevant security, deprecation, etc. announcements to the top of this version's changelog for visibility. This includes any announcements in RCs for this release.
+5. Check the upgrade notes for any important announcements, and link to them from the changelog if warranted.
+6. Quickly skim and check that each entry is in the appropriate section.
+7. Entries under the Bugfixes section should ideally state what Synapse version the bug was introduced in. For example: "Fixed a bug introduced in v1.x.y" or if no version can be identified, "Fixed a long-standing bug ...".
\ No newline at end of file
diff --git a/docs/development/synapse_architecture/cancellation.md b/docs/development/synapse_architecture/cancellation.md
index ef9e022635..a12f119fb5 100644
--- a/docs/development/synapse_architecture/cancellation.md
+++ b/docs/development/synapse_architecture/cancellation.md
@@ -299,7 +299,7 @@ logcontext is not finished before the `async` processing completes.
 
 **Bad**:
 ```python
-cache: Optional[ObservableDeferred[None]] = None
+cache: ObservableDeferred[None] | None = None
 
 async def do_something_else(
     to_resolve: Deferred[None]
@@ -326,7 +326,7 @@ with LoggingContext("request-1"):
 
 **Good**:
 ```python
-cache: Optional[ObservableDeferred[None]] = None
+cache: ObservableDeferred[None] | None = None
 
 async def do_something_else(
     to_resolve: Deferred[None]
@@ -358,7 +358,7 @@ with LoggingContext("request-1"):
 
 **OK**:
 ```python
-cache: Optional[ObservableDeferred[None]] = None
+cache: ObservableDeferred[None] | None = None
 
 async def do_something_else(
     to_resolve: Deferred[None]
diff --git a/docs/log_contexts.md b/docs/log_contexts.md
index bbe9e86827..76710e10e0 100644
--- a/docs/log_contexts.md
+++ b/docs/log_contexts.md
@@ -548,3 +548,19 @@ chain are dropped. Dropping the the reference to an awaitable you're
 supposed to be awaiting is bad practice, so this doesn't
 actually happen too much. Unfortunately, when it does happen, it will
 lead to leaked logcontexts which are incredibly hard to track down.
+
+
+## Debugging logcontext issues
+
+Debugging logcontext issues can be tricky as leaking or losing a logcontext will surface
+downstream and can point to an unrelated part of the codebase. It's best to enable debug
+logging for `synapse.logging.context.debug` (needs to be explicitly configured) and go
+backwards in the logs from the point where the issue is observed to find the root cause.
+
+`log.config.yaml`
+```yaml
+loggers:
+    # Unlike other loggers, this one needs to be explicitly configured to see debug logs.
+    synapse.logging.context.debug:
+        level: DEBUG
+```
diff --git a/docs/modules/account_data_callbacks.md b/docs/modules/account_data_callbacks.md
index 25de911627..02b8c18bbf 100644
--- a/docs/modules/account_data_callbacks.md
+++ b/docs/modules/account_data_callbacks.md
@@ -15,7 +15,7 @@ _First introduced in Synapse v1.57.0_
 ```python
 async def on_account_data_updated(
     user_id: str,
-    room_id: Optional[str],
+    room_id: str | None,
     account_data_type: str,
     content: "synapse.module_api.JsonDict",
 ) -> None:
@@ -82,7 +82,7 @@ class CustomAccountDataModule:
     async def log_new_account_data(
         self,
         user_id: str,
-        room_id: Optional[str],
+        room_id: str | None,
         account_data_type: str,
         content: JsonDict,
     ) -> None:
diff --git a/docs/modules/account_validity_callbacks.md b/docs/modules/account_validity_callbacks.md
index f5eefcd7d6..2deb43c1be 100644
--- a/docs/modules/account_validity_callbacks.md
+++ b/docs/modules/account_validity_callbacks.md
@@ -12,7 +12,7 @@ The available account validity callbacks are:
 _First introduced in Synapse v1.39.0_
 
 ```python
-async def is_user_expired(user: str) -> Optional[bool]
+async def is_user_expired(user: str) -> bool | None
 ```
 
 Called when processing any authenticated request (except for logout requests). The module
diff --git a/docs/modules/media_repository_callbacks.md b/docs/modules/media_repository_callbacks.md
index 7c724038a7..d7c9074bde 100644
--- a/docs/modules/media_repository_callbacks.md
+++ b/docs/modules/media_repository_callbacks.md
@@ -11,7 +11,7 @@ The available media repository callbacks are:
 _First introduced in Synapse v1.132.0_
 
 ```python
-async def get_media_config_for_user(user_id: str) -> Optional[JsonDict]
+async def get_media_config_for_user(user_id: str) -> JsonDict | None
 ```
 
 **<span style="color:red">
@@ -70,7 +70,7 @@ implementations of this callback.
 _First introduced in Synapse v1.139.0_
 
 ```python
-async def get_media_upload_limits_for_user(user_id: str, size: int) -> Optional[List[synapse.module_api.MediaUploadLimit]]
+async def get_media_upload_limits_for_user(user_id: str, size: int) -> list[synapse.module_api.MediaUploadLimit] | None
 ```
 
 **<span style="color:red">
diff --git a/docs/modules/password_auth_provider_callbacks.md b/docs/modules/password_auth_provider_callbacks.md
index d66ac7df31..88b22fdf21 100644
--- a/docs/modules/password_auth_provider_callbacks.md
+++ b/docs/modules/password_auth_provider_callbacks.md
@@ -23,12 +23,7 @@ async def check_auth(
     user: str,
     login_type: str,
     login_dict: "synapse.module_api.JsonDict",
-) -> Optional[
-    Tuple[
-        str, 
-        Optional[Callable[["synapse.module_api.LoginResponse"], Awaitable[None]]]
-    ]
-]
+) -> tuple[str, Callable[["synapse.module_api.LoginResponse"], Awaitable[None]] | None] | None
 ```
 
 The login type and field names should be provided by the user in the
@@ -67,12 +62,7 @@ async def check_3pid_auth(
     medium: str, 
     address: str,
     password: str,
-) -> Optional[
-    Tuple[
-        str, 
-        Optional[Callable[["synapse.module_api.LoginResponse"], Awaitable[None]]]
-    ]
-]
+) -> tuple[str, Callable[["synapse.module_api.LoginResponse"], Awaitable[None]] | None]
 ```
 
 Called when a user attempts to register or log in with a third party identifier,
@@ -98,7 +88,7 @@ _First introduced in Synapse v1.46.0_
 ```python
 async def on_logged_out(
     user_id: str,
-    device_id: Optional[str],
+    device_id: str | None,
     access_token: str
 ) -> None
 ``` 
@@ -119,7 +109,7 @@ _First introduced in Synapse v1.52.0_
 async def get_username_for_registration(
     uia_results: Dict[str, Any],
     params: Dict[str, Any],
-) -> Optional[str]
+) -> str | None
 ```
 
 Called when registering a new user. The module can return a username to set for the user
@@ -180,7 +170,7 @@ _First introduced in Synapse v1.54.0_
 async def get_displayname_for_registration(
     uia_results: Dict[str, Any],
     params: Dict[str, Any],
-) -> Optional[str]
+) -> str | None
 ```
 
 Called when registering a new user. The module can return a display name to set for the
@@ -259,12 +249,7 @@ class MyAuthProvider:
         username: str,
         login_type: str,
         login_dict: "synapse.module_api.JsonDict",
-    ) -> Optional[
-        Tuple[
-            str,
-            Optional[Callable[["synapse.module_api.LoginResponse"], Awaitable[None]]],
-        ]
-    ]:
+    ) -> tuple[str, Callable[["synapse.module_api.LoginResponse"], Awaitable[None]] | None] | None:
         if login_type != "my.login_type":
             return None
 
@@ -276,12 +261,7 @@ class MyAuthProvider:
         username: str,
         login_type: str,
         login_dict: "synapse.module_api.JsonDict",
-    ) -> Optional[
-        Tuple[
-            str,
-            Optional[Callable[["synapse.module_api.LoginResponse"], Awaitable[None]]],
-        ]
-    ]:
+    ) -> tuple[str, Callable[["synapse.module_api.LoginResponse"], Awaitable[None]] | None] | None:
         if login_type != "m.login.password":
             return None
 
diff --git a/docs/modules/presence_router_callbacks.md b/docs/modules/presence_router_callbacks.md
index b210f0e3cd..f865e79f53 100644
--- a/docs/modules/presence_router_callbacks.md
+++ b/docs/modules/presence_router_callbacks.md
@@ -23,7 +23,7 @@ _First introduced in Synapse v1.42.0_
 ```python 
 async def get_users_for_states(
     state_updates: Iterable["synapse.api.UserPresenceState"],
-) -> Dict[str, Set["synapse.api.UserPresenceState"]]
+) -> dict[str, set["synapse.api.UserPresenceState"]]
 ```
 **Requires** `get_interested_users` to also be registered
 
@@ -45,7 +45,7 @@ _First introduced in Synapse v1.42.0_
 ```python
 async def get_interested_users(
     user_id: str
-) -> Union[Set[str], "synapse.module_api.PRESENCE_ALL_USERS"]
+) -> set[str] | "synapse.module_api.PRESENCE_ALL_USERS"
 ```
 **Requires** `get_users_for_states` to also be registered
 
@@ -73,7 +73,7 @@ that `@alice:example.org` receives all presence updates from `@bob:example.com`
 `@charlie:somewhere.org`, regardless of whether Alice shares a room with any of them.
 
 ```python
-from typing import Dict, Iterable, Set, Union
+from typing import Iterable
 
 from synapse.module_api import ModuleApi
 
@@ -90,7 +90,7 @@ class CustomPresenceRouter:
     async def get_users_for_states(
         self,
         state_updates: Iterable["synapse.api.UserPresenceState"],
-    ) -> Dict[str, Set["synapse.api.UserPresenceState"]]:
+    ) -> dict[str, set["synapse.api.UserPresenceState"]]:
         res = {}
         for update in state_updates:
             if (
@@ -104,7 +104,7 @@ class CustomPresenceRouter:
     async def get_interested_users(
         self,
         user_id: str,
-    ) -> Union[Set[str], "synapse.module_api.PRESENCE_ALL_USERS"]:
+    ) -> set[str] | "synapse.module_api.PRESENCE_ALL_USERS":
         if user_id == "@alice:example.com":
             return {"@bob:example.com", "@charlie:somewhere.org"}
 
diff --git a/docs/modules/ratelimit_callbacks.md b/docs/modules/ratelimit_callbacks.md
index 30d94024fa..048bdc6f9e 100644
--- a/docs/modules/ratelimit_callbacks.md
+++ b/docs/modules/ratelimit_callbacks.md
@@ -11,7 +11,7 @@ The available ratelimit callbacks are:
 _First introduced in Synapse v1.132.0_
 
 ```python
-async def get_ratelimit_override_for_user(user: str, limiter_name: str) -> Optional[synapse.module_api.RatelimitOverride]
+async def get_ratelimit_override_for_user(user: str, limiter_name: str) -> synapse.module_api.RatelimitOverride | None
 ```
 
 **<span style="color:red">
diff --git a/docs/modules/spam_checker_callbacks.md b/docs/modules/spam_checker_callbacks.md
index 0f15a9dcc5..0d261e844f 100644
--- a/docs/modules/spam_checker_callbacks.md
+++ b/docs/modules/spam_checker_callbacks.md
@@ -331,9 +331,9 @@ search results; otherwise return `False`.
 The profile is represented as a dictionary with the following keys:
 
 * `user_id: str`. The Matrix ID for this user.
-* `display_name: Optional[str]`. The user's display name, or `None` if this user
+* `display_name: str | None`. The user's display name, or `None` if this user
   has not set a display name.
-* `avatar_url: Optional[str]`. The `mxc://` URL to the user's avatar, or `None`
+* `avatar_url: str | None`. The `mxc://` URL to the user's avatar, or `None`
   if this user has not set an avatar.
 
 The module is given a copy of the original dictionary, so modifying it from within the
@@ -352,10 +352,10 @@ _First introduced in Synapse v1.37.0_
 
 ```python
 async def check_registration_for_spam(
-    email_threepid: Optional[dict],
-    username: Optional[str],
+    email_threepid: dict | None,
+    username: str | None,
     request_info: Collection[Tuple[str, str]],
-    auth_provider_id: Optional[str] = None,
+    auth_provider_id: str | None = None,
 ) -> "synapse.spam_checker_api.RegistrationBehaviour"
 ```
 
@@ -438,10 +438,10 @@ _First introduced in Synapse v1.87.0_
 ```python
 async def check_login_for_spam(
     user_id: str,
-    device_id: Optional[str],
-    initial_display_name: Optional[str],
-    request_info: Collection[Tuple[Optional[str], str]],
-    auth_provider_id: Optional[str] = None,
+    device_id: str | None,
+    initial_display_name: str | None,
+    request_info: Collection[tuple[str | None, str]],
+    auth_provider_id: str | None = None,
 ) -> Union["synapse.module_api.NOT_SPAM", "synapse.module_api.errors.Codes"]
 ```
 
@@ -509,7 +509,7 @@ class ListSpamChecker:
             resource=IsUserEvilResource(config),
         )
 
-    async def check_event_for_spam(self, event: "synapse.events.EventBase") -> Union[Literal["NOT_SPAM"], Codes]:
+    async def check_event_for_spam(self, event: "synapse.events.EventBase") -> Literal["NOT_SPAM"] | Codes:
         if event.sender in self.evil_users:
           return Codes.FORBIDDEN
         else:
diff --git a/docs/modules/third_party_rules_callbacks.md b/docs/modules/third_party_rules_callbacks.md
index b97e28db11..1474b2dfd5 100644
--- a/docs/modules/third_party_rules_callbacks.md
+++ b/docs/modules/third_party_rules_callbacks.md
@@ -16,7 +16,7 @@ _First introduced in Synapse v1.39.0_
 async def check_event_allowed(
     event: "synapse.events.EventBase",
     state_events: "synapse.types.StateMap",
-) -> Tuple[bool, Optional[dict]]
+) -> tuple[bool, dict | None]
 ```
 
 **<span style="color:red">
@@ -340,7 +340,7 @@ class EventCensorer:
         self,
         event: "synapse.events.EventBase",
         state_events: "synapse.types.StateMap",
-    ) -> Tuple[bool, Optional[dict]]:
+    ) -> Tuple[bool, dict | None]:
         event_dict = event.get_dict()
         new_event_content = await self.api.http_client.post_json_get_json(
             uri=self._endpoint, post_json=event_dict,
diff --git a/docs/presence_router_module.md b/docs/presence_router_module.md
index face54fe2b..092b566c5f 100644
--- a/docs/presence_router_module.md
+++ b/docs/presence_router_module.md
@@ -76,7 +76,7 @@ possible.
 #### `get_interested_users`
 
 ```python
-async def get_interested_users(self, user_id: str) -> Union[Set[str], str]
+async def get_interested_users(self, user_id: str) -> set[str] | str
 ```
 
 **Required.** An asynchronous method that is passed a single Matrix User ID. This
@@ -182,7 +182,7 @@ class ExamplePresenceRouter:
     async def get_interested_users(
         self,
         user_id: str,
-    ) -> Union[Set[str], PresenceRouter.ALL_USERS]:
+    ) -> set[str] | PresenceRouter.ALL_USERS:
         """
         Retrieve a list of users that `user_id` is interested in receiving the
         presence of. This will be in addition to those they share a room with.
diff --git a/docs/setup/installation.md b/docs/setup/installation.md
index 0840f532b0..786672c689 100644
--- a/docs/setup/installation.md
+++ b/docs/setup/installation.md
@@ -87,17 +87,13 @@ file when you upgrade the Debian package to a later version.
 Andrej Shadura maintains a
 [`matrix-synapse`](https://packages.debian.org/sid/matrix-synapse) package in
 the Debian repositories.
-For `bookworm` and `sid`, it can be installed simply with:
+For `forky` (14) and `sid` (rolling release), it can be installed simply with:
 
 ```sh
 sudo apt install matrix-synapse
 ```
 
-Synapse is also available in `bullseye-backports`.  Please
-see the [Debian documentation](https://backports.debian.org/Instructions/)
-for information on how to use backports.
-
-`matrix-synapse` is no longer maintained for `buster` and older.
+The downstream Debian `matrix-synapse` package is not available for `trixie` (13) and older. Consider using the Matrix.org packages (above).
 
 ##### Downstream Ubuntu packages
 
@@ -208,7 +204,7 @@ When following this route please make sure that the [Platform-specific prerequis
 System requirements:
 
 - POSIX-compliant system (tested on Linux & OS X)
-- Python 3.9 or later, up to Python 3.13.
+- Python 3.10 or later, up to Python 3.13.
 - At least 1GB of free RAM if you want to join large public rooms like #matrix:matrix.org
 
 If building on an uncommon architecture for which pre-built wheels are
@@ -311,11 +307,16 @@ sudo dnf group install "Development Tools"
 
 ##### Red Hat Enterprise Linux / Rocky Linux / Oracle Linux
 
-*Note: The term "RHEL" below refers to Red Hat Enterprise Linux, Oracle Linux and Rocky Linux. The distributions are 1:1 binary compatible.*
+*Note: The term "RHEL" below refers to Red Hat Enterprise Linux, Oracle Linux and Rocky Linux.
+The distributions are 1:1 binary compatible.*
 
 It's recommended to use the latest Python versions.
 
-RHEL 8 in particular ships with Python 3.6 by default which is EOL and therefore no longer supported by Synapse. RHEL 9 ships with Python 3.9 which is still supported by the Python core team as of this writing. However, newer Python versions provide significant performance improvements and they're available in official distributions' repositories. Therefore it's recommended to use them.
+RHEL 8 & 9 in particular ship with Python 3.6 & 3.9 respectively by default
+which are EOL and therefore no longer supported by Synapse.
+However, newer Python versions provide significant performance improvements
+and they're available in official distributions' repositories.
+Therefore it's recommended to use them.
 
 Python 3.11 and 3.12 are available for both RHEL 8 and 9.
 
diff --git a/docs/upgrade.md b/docs/upgrade.md
index 5f998e9708..b3121a01a0 100644
--- a/docs/upgrade.md
+++ b/docs/upgrade.md
@@ -117,6 +117,44 @@ each upgrade are complete before moving on to the next upgrade, to avoid
 stacking them up. You can monitor the currently running background updates with
 [the Admin API](usage/administration/admin_api/background_updates.html#status).
 
+# Upgrading to v1.142.0
+
+## Python 3.10+ is now required
+
+The minimum supported Python version has been increased from v3.9 to v3.10.
+You will need Python 3.10+ to run Synapse v1.142.0.
+
+If you use current versions of the
+[matrixorg/synapse](setup/installation.html#docker-images-and-ansible-playbooks)
+Docker images, no action is required.
+
+## SQLite 3.40.0+ is now required
+
+The minimum supported SQLite version has been increased from 3.27.0 to 3.40.0.
+
+If you use current versions of the
+[matrixorg/synapse](setup/installation.html#docker-images-and-ansible-playbooks)
+Docker images, no action is required.
+
+
+# Upgrading to v1.141.0
+
+## Docker images now based on Debian `trixie` with Python 3.13
+
+The Docker images are now based on Debian `trixie` and use Python 3.13. If you
+are using the Docker images as a base image you may need to e.g. adjust the
+paths you mount any additional Python packages at.
+
+# Upgrading to v1.140.0
+
+## Users of `synapse-s3-storage-provider` must update the module to `v1.6.0`
+
+Deployments that make use of the
+[synapse-s3-storage-provider](https://github.com/matrix-org/synapse-s3-storage-provider/)
+module must update it to
+[v1.6.0](https://github.com/matrix-org/synapse-s3-storage-provider/releases/tag/v1.6.0),
+otherwise users will be unable to upload or download media.
+
 # Upgrading to v1.139.0
 
 ## `/register` requests from old application service implementations may break when using MAS
diff --git a/docs/usage/configuration/config_documentation.md b/docs/usage/configuration/config_documentation.md
index 3c401d569b..7509e4d715 100644
--- a/docs/usage/configuration/config_documentation.md
+++ b/docs/usage/configuration/config_documentation.md
@@ -2006,9 +2006,8 @@ This setting has the following sub-options:
 Default configuration:
 ```yaml
 rc_reports:
-  per_user:
-    per_second: 1.0
-    burst_count: 5.0
+  per_second: 1.0
+  burst_count: 5.0
 ```
 
 Example configuration:
@@ -2031,9 +2030,8 @@ This setting has the following sub-options:
 Default configuration:
 ```yaml
 rc_room_creation:
-  per_user:
-    per_second: 0.016
-    burst_count: 10.0
+  per_second: 0.016
+  burst_count: 10.0
 ```
 
 Example configuration:
@@ -2575,6 +2573,28 @@ Example configuration:
 turn_allow_guests: false
 ```
 ---
+### `matrix_rtc`
+
+*(object)* Options related to MatrixRTC. Defaults to `{}`.
+
+This setting has the following sub-options:
+
+* `transports` (array): A list of transport types and arguments to use for MatrixRTC connections. Defaults to `[]`.
+
+  Options for each entry include:
+
+  * `type` (string): The type of transport to use to connect to the selective forwarding unit (SFU).
+
+  * `livekit_service_url` (string): The base URL of the LiveKit service. Should only be used with LiveKit-based transports.
+
+Example configuration:
+```yaml
+matrix_rtc:
+  transports:
+  - type: livekit
+    livekit_service_url: https://matrix-rtc.example.com/livekit/jwt
+```
+---
 ## Registration
 
 Registration can be rate-limited using the parameters in the [Ratelimiting](#ratelimiting) section of this manual.
@@ -3795,7 +3815,7 @@ This setting has the following sub-options:
 
 * `localdb_enabled` (boolean): Set to false to disable authentication against the local password database. This is ignored if `enabled` is false, and is only useful if you have other `password_providers`. Defaults to `true`.
 
-* `pepper` (string|null): Set the value here to a secret random string for extra security. DO NOT CHANGE THIS AFTER INITIAL SETUP! Defaults to `null`.
+* `pepper` (string|null): A secret random string that will be appended to user's passwords before they are hashed. This improves the security of short passwords. DO NOT CHANGE THIS AFTER INITIAL SETUP! Defaults to `null`.
 
 * `policy` (object): Define and enforce a password policy, such as minimum lengths for passwords, etc. This is an implementation of MSC2000.
 
diff --git a/docs/workers.md b/docs/workers.md
index 18bb0b76f6..f766b40251 100644
--- a/docs/workers.md
+++ b/docs/workers.md
@@ -120,6 +120,9 @@ worker_replication_secret: ""
 
 redis:
     enabled: true
+    # For additional Redis configuration options (TLS, authentication, etc.), 
+    # see the Synapse configuration documentation:
+    # https://element-hq.github.io/synapse/latest/usage/configuration/config_documentation.html#redis
 
 instance_map:
     main:
diff --git a/mypy.ini b/mypy.ini
index ae903f858a..d6a3434293 100644
--- a/mypy.ini
+++ b/mypy.ini
@@ -37,7 +37,7 @@ strict_equality = True
 
 # Run mypy type checking with the minimum supported Python version to catch new usage
 # that isn't backwards-compatible (types, overloads, etc).
-python_version = 3.9
+python_version = 3.10
 
 files =
   docker/,
@@ -69,7 +69,7 @@ warn_unused_ignores = False
 ;;     https://github.com/python/typeshed/tree/master/stubs
 ;; and for each package `foo` there's a corresponding `types-foo` package on PyPI,
 ;; which we can pull in as a dev dependency by adding to `pyproject.toml`'s
-;; `[tool.poetry.dev-dependencies]` list.
+;; `[tool.poetry.group.dev.dependencies]` list.
 
 # https://github.com/lepture/authlib/issues/460
 [mypy-authlib.*]
diff --git a/poetry.lock b/poetry.lock
index 55de265559..1de977f15c 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -1,4 +1,4 @@
-# This file is automatically @generated by Poetry 2.2.0 and should not be changed by hand.
+# This file is automatically @generated by Poetry 2.2.1 and should not be changed by hand.
 
 [[package]]
 name = "annotated-types"
@@ -6,7 +6,7 @@ version = "0.7.0"
 description = "Reusable constraint types to use with typing.Annotated"
 optional = false
 python-versions = ">=3.8"
-groups = ["main", "dev"]
+groups = ["main"]
 files = [
     {file = "annotated_types-0.7.0-py3-none-any.whl", hash = "sha256:1f02e8b43a8fbbc3f3e0d4f0f4bfc8131bcb4eebe8849b8e5c773f3a1c582a53"},
     {file = "annotated_types-0.7.0.tar.gz", hash = "sha256:aff07c09a53a08bc8cfccb9c85b05f1aa9a2a6f23728d790723543408344ce89"},
@@ -34,15 +34,15 @@ tests-mypy = ["mypy (>=1.11.1) ; platform_python_implementation == \"CPython\" a
 
 [[package]]
 name = "authlib"
-version = "1.6.4"
+version = "1.6.5"
 description = "The ultimate Python library in building OAuth and OpenID Connect servers and clients."
 optional = true
 python-versions = ">=3.9"
 groups = ["main"]
 markers = "extra == \"all\" or extra == \"jwt\" or extra == \"oidc\""
 files = [
-    {file = "authlib-1.6.4-py2.py3-none-any.whl", hash = "sha256:39313d2a2caac3ecf6d8f95fbebdfd30ae6ea6ae6a6db794d976405fdd9aa796"},
-    {file = "authlib-1.6.4.tar.gz", hash = "sha256:104b0442a43061dc8bc23b133d1d06a2b0a9c2e3e33f34c4338929e816287649"},
+    {file = "authlib-1.6.5-py2.py3-none-any.whl", hash = "sha256:3e0e0507807f842b02175507bdee8957a1d5707fd4afb17c32fb43fee90b6e3a"},
+    {file = "authlib-1.6.5.tar.gz", hash = "sha256:6aaf9c79b7cc96c900f0b284061691c5d4e61221640a948fe690b556a6d6d10b"},
 ]
 
 [package.dependencies]
@@ -60,9 +60,6 @@ files = [
     {file = "automat-25.4.16.tar.gz", hash = "sha256:0017591a5477066e90d26b0e696ddc143baafd87b588cfac8100bc6be9634de0"},
 ]
 
-[package.dependencies]
-typing_extensions = {version = "*", markers = "python_version < \"3.10\""}
-
 [package.extras]
 visualize = ["Twisted (>=16.1.1)", "graphviz (>0.5.1)"]
 
@@ -510,7 +507,6 @@ files = [
 
 [package.dependencies]
 gitdb = ">=4.0.1,<5"
-typing-extensions = {version = ">=3.10.0.2", markers = "python_version < \"3.10\""}
 
 [package.extras]
 doc = ["sphinx (>=7.1.2,<7.2)", "sphinx-autodoc-typehints", "sphinx_rtd_theme"]
@@ -518,122 +514,118 @@ test = ["coverage[toml]", "ddt (>=1.1.1,!=1.4.3)", "mock ; python_version < \"3.
 
 [[package]]
 name = "hiredis"
-version = "3.2.1"
+version = "3.3.0"
 description = "Python wrapper for hiredis"
 optional = true
 python-versions = ">=3.8"
 groups = ["main"]
 markers = "extra == \"all\" or extra == \"redis\""
 files = [
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 [[package]]
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 [[package]]
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+version = "3.11"
 description = "Internationalized Domain Names in Applications (IDNA)"
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 ]
 
 [[package]]
@@ -800,7 +802,7 @@ description = "Read metadata from Python packages"
 optional = false
 python-versions = ">=3.7"
 groups = ["dev"]
-markers = "platform_machine != \"ppc64le\" and platform_machine != \"s390x\" and python_version < \"3.12\" or python_version < \"3.10\""
+markers = "platform_machine != \"ppc64le\" and platform_machine != \"s390x\" and python_version < \"3.12\""
 files = [
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@@ -814,26 +816,6 @@ docs = ["furo", "jaraco.packaging (>=9)", "jaraco.tidelift (>=1.4)", "rst.linker
 perf = ["ipython"]
 testing = ["flufl.flake8", "importlib-resources (>=1.3) ; python_version < \"3.9\"", "packaging", "pyfakefs", "pytest (>=6)", "pytest-black (>=0.3.7) ; platform_python_implementation != \"PyPy\"", "pytest-checkdocs (>=2.4)", "pytest-cov", "pytest-enabler (>=1.3)", "pytest-mypy (>=0.9.1) ; platform_python_implementation != \"PyPy\"", "pytest-perf (>=0.9.2)", "pytest-ruff"]
 
-[[package]]
-name = "importlib-resources"
-version = "5.12.0"
-description = "Read resources from Python packages"
-optional = false
-python-versions = ">=3.7"
-groups = ["dev"]
-markers = "python_version < \"3.10\""
-files = [
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-]
-
-[package.dependencies]
-zipp = {version = ">=3.1.0", markers = "python_version < \"3.10\""}
-
-[package.extras]
-docs = ["furo", "jaraco.packaging (>=9)", "jaraco.tidelift (>=1.4)", "rst.linker (>=1.9)", "sphinx (>=3.5)", "sphinx-lint"]
-testing = ["flake8 (<5)", "pytest (>=6)", "pytest-black (>=0.3.7) ; platform_python_implementation != \"PyPy\"", "pytest-checkdocs (>=2.4)", "pytest-cov", "pytest-enabler (>=1.3)", "pytest-flake8 ; python_version < \"3.12\"", "pytest-mypy (>=0.9.1) ; platform_python_implementation != \"PyPy\""]
-
 [[package]]
 name = "incremental"
 version = "24.7.2"
@@ -1181,14 +1163,14 @@ test = ["coverage[toml] (>=7.2.5)", "mypy (>=1.2.0)", "pytest (>=7.3.0)", "pytes
 
 [[package]]
 name = "markdown-it-py"
-version = "3.0.0"
+version = "4.0.0"
 description = "Python port of markdown-it. Markdown parsing, done right!"
 optional = false
-python-versions = ">=3.8"
+python-versions = ">=3.10"
 groups = ["dev"]
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 python-versions = "*"
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 [[package]]
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 [package.extras]
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 [[package]]
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 [package.extras]
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 [[package]]
@@ -2347,138 +2366,156 @@ jupyter = ["ipywidgets (>=7.5.1,<9)"]
 
 [[package]]
 name = "rpds-py"
-version = "0.8.10"
+version = "0.28.0"
 description = "Python bindings to Rust's persistent data structures (rpds)"
 optional = false
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 groups = ["main", "dev"]
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 [[package]]
@@ -2779,6 +2816,7 @@ files = [
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 ]
+markers = {main = "python_version < \"3.14\""}
 
 [[package]]
 name = "tornado"
@@ -2817,8 +2855,6 @@ files = [
 
 [package.dependencies]
 click = "*"
-importlib-metadata = {version = ">=4.6", markers = "python_version < \"3.10\""}
-importlib-resources = {version = ">=5", markers = "python_version < \"3.10\""}
 jinja2 = "*"
 tomli = {version = "*", markers = "python_version < \"3.11\""}
 
@@ -2864,7 +2900,6 @@ files = [
 
 [package.dependencies]
 id = "*"
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 keyring = {version = ">=21.2.0", markers = "platform_machine != \"ppc64le\" and platform_machine != \"s390x\""}
 packaging = ">=24.0"
 readme-renderer = ">=35.0"
@@ -3029,14 +3064,14 @@ files = [
 
 [[package]]
 name = "types-psycopg2"
-version = "2.9.21.20250915"
+version = "2.9.21.20251012"
 description = "Typing stubs for psycopg2"
 optional = false
 python-versions = ">=3.9"
 groups = ["dev"]
 files = [
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 ]
 
 [[package]]
@@ -3057,14 +3092,14 @@ types-cffi = "*"
 
 [[package]]
 name = "types-pyyaml"
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+version = "6.0.12.20250915"
 description = "Typing stubs for PyYAML"
 optional = false
 python-versions = ">=3.9"
 groups = ["dev"]
 files = [
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 ]
 
 [[package]]
@@ -3108,14 +3143,14 @@ files = [
 
 [[package]]
 name = "typing-inspection"
-version = "0.4.0"
+version = "0.4.2"
 description = "Runtime typing introspection tools"
 optional = false
 python-versions = ">=3.9"
-groups = ["main", "dev"]
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 [package.dependencies]
@@ -3191,7 +3226,7 @@ description = "Backport of pathlib-compatible object wrapper for zip files"
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 python-versions = ">=3.8"
 groups = ["dev"]
-markers = "platform_machine != \"ppc64le\" and platform_machine != \"s390x\" and python_version < \"3.12\" or python_version < \"3.10\""
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 files = [
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@@ -3222,54 +3257,45 @@ test = ["zope.testrunner"]
 
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+version = "8.0.1"
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+    {file = "zope_interface-8.0.1-cp39-cp39-win_amd64.whl", hash = "sha256:a0016ca85f93b938824e2f9a43534446e95134a2945b084944786e1ace2020bc"},
+    {file = "zope_interface-8.0.1.tar.gz", hash = "sha256:eba5610d042c3704a48222f7f7c6ab5b243ed26f917e2bc69379456b115e02d1"},
 ]
 
-[package.dependencies]
-setuptools = "*"
-
 [package.extras]
 docs = ["Sphinx", "furo", "repoze.sphinx.autointerface"]
 test = ["coverage[toml]", "zope.event", "zope.testing"]
@@ -3313,5 +3339,5 @@ url-preview = ["lxml"]
 
 [metadata]
 lock-version = "2.1"
-python-versions = "^3.9.0"
-content-hash = "2e8ea085e1a0c6f0ac051d4bc457a96827d01f621b1827086de01a5ffa98cf79"
+python-versions = "^3.10.0"
+content-hash = "2a891bc466355554d5c5873e7f8592e4f693de4d0f734ddb55f8a55bb4e529df"
diff --git a/pyproject.toml b/pyproject.toml
index c9f81850f7..7b60dd06f6 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -36,7 +36,7 @@
 
 [tool.ruff]
 line-length = 88
-target-version = "py39"
+target-version = "py310"
 
 [tool.ruff.lint]
 # See https://beta.ruff.rs/docs/rules/#error-e
@@ -78,6 +78,17 @@ select = [
     "LOG",
     # flake8-logging-format
     "G",
+    # pyupgrade
+    "UP006",
+    "UP007",
+    "UP045",
+]
+extend-safe-fixes = [
+    # pyupgrade rules compatible with Python >= 3.9
+    "UP006",
+    "UP007",
+    # pyupgrade rules compatible with Python >= 3.10
+    "UP045",
 ]
 
 [tool.ruff.lint.isort]
@@ -101,7 +112,7 @@ module-name = "synapse.synapse_rust"
 
 [tool.poetry]
 name = "matrix-synapse"
-version = "1.139.0rc3"
+version = "1.142.0rc4"
 description = "Homeserver for the Matrix decentralised comms protocol"
 authors = ["Matrix.org Team and Contributors <packages@matrix.org>"]
 license = "AGPL-3.0-or-later OR LicenseRef-Element-Commercial"
@@ -159,12 +170,16 @@ synapse_review_recent_signups = "synapse._scripts.review_recent_signups:main"
 update_synapse_database = "synapse._scripts.update_synapse_database:main"
 
 [tool.poetry.dependencies]
-python = "^3.9.0"
+python = "^3.10.0"
 
 # Mandatory Dependencies
 # ----------------------
 # we use the TYPE_CHECKER.redefine method added in jsonschema 3.0.0
 jsonschema = ">=3.0.0"
+# 0.25.0 is the first version to support Python 3.14.
+# We can remove this once https://github.com/python-jsonschema/jsonschema/issues/1426 is fixed
+# and included in a release.
+rpds-py = ">=0.25.0"
 # We choose 2.0 as a lower bound: the most recent backwards incompatible release.
 # It seems generally available, judging by https://pkgs.org/search/?q=immutabledict
 immutabledict = ">=2.0"
@@ -195,7 +210,8 @@ bcrypt = ">=3.1.7"
 # Packagers that already took care of libwebp can lower that down to 5.4.0.
 Pillow = ">=10.0.1"
 # We use SortedDict.peekitem(), which was added in sortedcontainers 1.5.2.
-sortedcontainers = ">=1.5.2"
+# 2.0.5 updates collections.abc imports to avoid Python 3.10 incompatibility.
+sortedcontainers = ">=2.0.5"
 pymacaroons = ">=0.13.0"
 msgpack = ">=0.5.2"
 phonenumbers = ">=8.2.0"
@@ -211,9 +227,10 @@ netaddr = ">=0.7.18"
 # end up with a broken installation, with recent MarkupSafe but old Jinja, we
 # add a lower bound to the Jinja2 dependency.
 Jinja2 = ">=3.0"
-bleach = ">=1.4.3"
-# We use `assert_never`, which were added in `typing-extensions` 4.1.
-typing-extensions = ">=4.1"
+# 3.2.0 updates collections.abc imports to avoid Python 3.10 incompatibility.
+bleach = ">=3.2.0"
+# pydantic 2.12 depends on typing-extensions>=4.14.1
+typing-extensions = ">=4.14.1"
 # We enforce that we have a `cryptography` version that bundles an `openssl`
 # with the latest security patches.
 cryptography = ">=3.4.7"
@@ -222,9 +239,10 @@ ijson = ">=3.1.4"
 matrix-common = "^1.3.0"
 # We need packaging.verison.Version(...).major added in 20.0.
 packaging = ">=20.0"
-# We support pydantic v1 and pydantic v2 via the pydantic.v1 compat module.
-# See https://github.com/matrix-org/synapse/issues/15858
-pydantic = ">=1.7.4, <3"
+pydantic = [
+    { version = "~=2.8", python = "<3.14" },
+    { version = "~=2.12", python = ">=3.14" },
+]
 
 # This is for building the rust components during "poetry install", which
 # currently ignores the `build-system.requires` directive (c.f.
@@ -252,10 +270,12 @@ authlib = { version = ">=0.15.1", optional = true }
 # `contrib/systemd/log_config.yaml`.
 # Note: systemd-python 231 appears to have been yanked from pypi
 systemd-python = { version = ">=231", optional = true }
-lxml = { version = ">=4.5.2", optional = true }
+# 4.6.3 removes usage of _PyGen_Send which is unavailable in CPython as of Python 3.10.
+lxml = { version = ">=4.6.3", optional = true }
 sentry-sdk = { version = ">=0.7.2", optional = true }
 opentracing = { version = ">=2.2.0", optional = true }
-jaeger-client = { version = ">=4.0.0", optional = true }
+# 4.2.0 updates collections.abc imports to avoid Python 3.10 incompatibility.
+jaeger-client = { version = ">=4.2.0", optional = true }
 txredisapi = { version = ">=1.4.7", optional = true }
 hiredis = { version = "*", optional = true }
 Pympler = { version = "*", optional = true }
@@ -319,14 +339,12 @@ all = [
     #   - systemd: this is a system-based requirement
 ]
 
-[tool.poetry.dev-dependencies]
+[tool.poetry.group.dev.dependencies]
 # We pin development dependencies in poetry.lock so that our tests don't start
 # failing on new releases. Keeping lower bounds loose here means that dependabot
 # can bump versions without having to update the content-hash in the lockfile.
 # This helps prevents merge conflicts when running a batch of dependabot updates.
-ruff = "0.12.10"
-# Type checking only works with the pydantic.v1 compat module from pydantic v2
-pydantic = "^2"
+ruff = "0.14.3"
 
 # Typechecking
 lxml-stubs = ">=0.4.0"
@@ -356,7 +374,7 @@ click = ">=8.1.3"
 # GitPython was == 3.1.14; bumped to 3.1.20, the first release with type hints.
 GitPython = ">=3.1.20"
 markdown-it-py = ">=3.0.0"
-pygithub = ">=1.55"
+pygithub = ">=1.59"
 # The following are executed as commands by the release script.
 twine = "*"
 # Towncrier min version comes from https://github.com/matrix-org/synapse/pull/3425. Rationale unclear.
@@ -381,10 +399,10 @@ build-backend = "poetry.core.masonry.api"
 # Skip unsupported platforms (by us or by Rust).
 # See https://cibuildwheel.readthedocs.io/en/stable/options/#build-skip for the list of build targets.
 # We skip:
-#  - CPython and PyPy 3.8: EOLed
+#  - CPython 3.8: EOLed
 #  - musllinux i686: excluded to reduce number of wheels we build.
 #    c.f. https://github.com/matrix-org/synapse/pull/12595#discussion_r963107677
-skip = "cp38* pp38* *-musllinux_i686"
+skip = "cp38* *-musllinux_i686"
 # Enable non-default builds.
 # "pypy" used to be included by default up until cibuildwheel 3.
 enable = "pypy"
diff --git a/rust/Cargo.toml b/rust/Cargo.toml
index 0706357294..e8321d159b 100644
--- a/rust/Cargo.toml
+++ b/rust/Cargo.toml
@@ -30,14 +30,14 @@ http = "1.1.0"
 lazy_static = "1.4.0"
 log = "0.4.17"
 mime = "0.3.17"
-pyo3 = { version = "0.25.1", features = [
+pyo3 = { version = "0.26.0", features = [
     "macros",
     "anyhow",
     "abi3",
-    "abi3-py39",
+    "abi3-py310",
 ] }
-pyo3-log = "0.12.4"
-pythonize = "0.25.0"
+pyo3-log = "0.13.1"
+pythonize = "0.26.0"
 regex = "1.6.0"
 sha2 = "0.10.8"
 serde = { version = "1.0.144", features = ["derive"] }
diff --git a/rust/src/events/internal_metadata.rs b/rust/src/events/internal_metadata.rs
index 4711fc540f..fa40fdcfad 100644
--- a/rust/src/events/internal_metadata.rs
+++ b/rust/src/events/internal_metadata.rs
@@ -41,7 +41,7 @@ use pyo3::{
     pybacked::PyBackedStr,
     pyclass, pymethods,
     types::{PyAnyMethods, PyDict, PyDictMethods, PyString},
-    Bound, IntoPyObject, PyAny, PyObject, PyResult, Python,
+    Bound, IntoPyObject, Py, PyAny, PyResult, Python,
 };
 
 use crate::UnwrapInfallible;
@@ -289,7 +289,7 @@ impl EventInternalMetadata {
     /// Get a dict holding the data stored in the `internal_metadata` column in the database.
     ///
     /// Note that `outlier` and `stream_ordering` are stored in separate columns so are not returned here.
-    fn get_dict(&self, py: Python<'_>) -> PyResult<PyObject> {
+    fn get_dict(&self, py: Python<'_>) -> PyResult<Py<PyAny>> {
         let dict = PyDict::new(py);
 
         for entry in &self.data {
diff --git a/rust/src/http_client.rs b/rust/src/http_client.rs
index b6cdf98f55..4bd80c8e04 100644
--- a/rust/src/http_client.rs
+++ b/rust/src/http_client.rs
@@ -12,7 +12,7 @@
  * <https://www.gnu.org/licenses/agpl-3.0.html>.
  */
 
-use std::{collections::HashMap, future::Future};
+use std::{collections::HashMap, future::Future, sync::OnceLock};
 
 use anyhow::Context;
 use futures::TryStreamExt;
@@ -134,10 +134,10 @@ fn get_runtime<'a>(reactor: &Bound<'a, PyAny>) -> PyResult<PyRef<'a, PyTokioRunt
 }
 
 /// A reference to the `twisted.internet.defer` module.
-static DEFER: OnceCell<PyObject> = OnceCell::new();
+static DEFER: OnceCell<Py<PyAny>> = OnceCell::new();
 
 /// Access to the `twisted.internet.defer` module.
-fn defer(py: Python<'_>) -> PyResult<&Bound<PyAny>> {
+fn defer(py: Python<'_>) -> PyResult<&Bound<'_, PyAny>> {
     Ok(DEFER
         .get_or_try_init(|| py.import("twisted.internet.defer").map(Into::into))?
         .bind(py))
@@ -165,7 +165,7 @@ pub fn register_module(py: Python<'_>, m: &Bound<'_, PyModule>) -> PyResult<()>
 #[pyclass]
 struct HttpClient {
     client: reqwest::Client,
-    reactor: PyObject,
+    reactor: Py<PyAny>,
 }
 
 #[pymethods]
@@ -237,7 +237,7 @@ impl HttpClient {
                 return Err(HttpResponseException::new(status, buffer));
             }
 
-            let r = Python::with_gil(|py| buffer.into_pyobject(py).map(|o| o.unbind()))?;
+            let r = Python::attach(|py| buffer.into_pyobject(py).map(|o| o.unbind()))?;
 
             Ok(r)
         })
@@ -270,7 +270,7 @@ where
     handle.spawn(async move {
         let res = task.await;
 
-        Python::with_gil(move |py| {
+        Python::attach(move |py| {
             // Flatten the panic into standard python error
             let res = match res {
                 Ok(r) => r,
@@ -299,5 +299,22 @@ where
         });
     });
 
-    Ok(deferred)
+    // Make the deferred follow the Synapse logcontext rules
+    make_deferred_yieldable(py, &deferred)
+}
+
+static MAKE_DEFERRED_YIELDABLE: OnceLock<pyo3::Py<pyo3::PyAny>> = OnceLock::new();
+
+/// Given a deferred, make it follow the Synapse logcontext rules
+fn make_deferred_yieldable<'py>(
+    py: Python<'py>,
+    deferred: &Bound<'py, PyAny>,
+) -> PyResult<Bound<'py, PyAny>> {
+    let make_deferred_yieldable = MAKE_DEFERRED_YIELDABLE.get_or_init(|| {
+        let sys = PyModule::import(py, "synapse.logging.context").unwrap();
+        let func = sys.getattr("make_deferred_yieldable").unwrap().unbind();
+        func
+    });
+
+    make_deferred_yieldable.call1(py, (deferred,))?.extract(py)
 }
diff --git a/rust/src/rendezvous/mod.rs b/rust/src/rendezvous/mod.rs
index 3148e0f67a..848b5035bb 100644
--- a/rust/src/rendezvous/mod.rs
+++ b/rust/src/rendezvous/mod.rs
@@ -29,7 +29,7 @@ use pyo3::{
     exceptions::PyValueError,
     pyclass, pymethods,
     types::{PyAnyMethods, PyModule, PyModuleMethods},
-    Bound, IntoPyObject, Py, PyAny, PyObject, PyResult, Python,
+    Bound, IntoPyObject, Py, PyAny, PyResult, Python,
 };
 use ulid::Ulid;
 
@@ -56,7 +56,7 @@ fn prepare_headers(headers: &mut HeaderMap, session: &Session) {
 #[pyclass]
 struct RendezvousHandler {
     base: Uri,
-    clock: PyObject,
+    clock: Py<PyAny>,
     sessions: BTreeMap<Ulid, Session>,
     capacity: usize,
     max_content_length: u64,
diff --git a/schema/synapse-config.schema.yaml b/schema/synapse-config.schema.yaml
index 2a7f94a700..98204a724c 100644
--- a/schema/synapse-config.schema.yaml
+++ b/schema/synapse-config.schema.yaml
@@ -1,5 +1,5 @@
 $schema: https://element-hq.github.io/synapse/latest/schema/v1/meta.schema.json
-$id: https://element-hq.github.io/synapse/schema/synapse/v1.139/synapse-config.schema.json
+$id: https://element-hq.github.io/synapse/schema/synapse/v1.142/synapse-config.schema.json
 type: object
 properties:
   modules:
@@ -2259,9 +2259,8 @@ properties:
       Setting this to a high value allows users to report content quickly, possibly in
       duplicate. This can result in higher database usage.
     default:
-      per_user:
-        per_second: 1.0
-        burst_count: 5.0
+      per_second: 1.0
+      burst_count: 5.0
     examples:
       - per_second: 2.0
         burst_count: 20.0
@@ -2270,9 +2269,8 @@ properties:
     description: >-
       Sets rate limits for how often users are able to create rooms.
     default:
-      per_user:
-        per_second: 0.016
-        burst_count: 10.0
+      per_second: 0.016
+      burst_count: 10.0
     examples:
       - per_second: 1.0
         burst_count: 5.0
@@ -2886,6 +2884,35 @@ properties:
     default: true
     examples:
       - false
+  matrix_rtc:
+    type: object 
+    description: >-
+      Options related to MatrixRTC.
+    properties:
+      transports:
+        type: array
+        items:
+          type: object
+          required:
+            - type
+          properties:
+            type:
+              type: string
+              description: The type of transport to use to connect to the selective forwarding unit (SFU).
+              example: livekit
+            livekit_service_url:
+              type: string
+              description: >-
+                The base URL of the LiveKit service. Should only be used with LiveKit-based transports.
+              example: https://matrix-rtc.example.com/livekit/jwt
+        description:
+          A list of transport types and arguments to use for MatrixRTC connections.
+        default: []
+    default: {}
+    examples:
+      - transports:
+        - type: livekit
+          livekit_service_url: https://matrix-rtc.example.com/livekit/jwt
   enable_registration:
     type: boolean
     description: >-
@@ -4668,8 +4695,9 @@ properties:
       pepper:
         type: ["string", "null"]
         description: >-
-          Set the value here to a secret random string for extra security. DO
-          NOT CHANGE THIS AFTER INITIAL SETUP!
+          A secret random string that will be appended to user's passwords
+          before they are hashed. This improves the security of short passwords.
+          DO NOT CHANGE THIS AFTER INITIAL SETUP!
         default: null
       policy:
         type: object
diff --git a/scripts-dev/build_debian_packages.py b/scripts-dev/build_debian_packages.py
index 6150dc15a3..d462fe6c56 100755
--- a/scripts-dev/build_debian_packages.py
+++ b/scripts-dev/build_debian_packages.py
@@ -18,16 +18,15 @@ import sys
 import threading
 from concurrent.futures import ThreadPoolExecutor
 from types import FrameType
-from typing import Collection, Optional, Sequence, Set
+from typing import Collection, Sequence
 
 # These are expanded inside the dockerfile to be a fully qualified image name.
-# e.g. docker.io/library/debian:bullseye
+# e.g. docker.io/library/debian:bookworm
 #
 # If an EOL is forced by a Python version and we're dropping support for it, make sure
-# to remove references to the distibution across Synapse (search for "bullseye" for
+# to remove references to the distibution across Synapse (search for "bookworm" for
 # example)
 DISTS = (
-    "debian:bullseye",  # (EOL ~2024-07) (our EOL forced by Python 3.9 is 2025-10-05)
     "debian:bookworm",  # (EOL 2026-06) (our EOL forced by Python 3.11 is 2027-10-24)
     "debian:sid",  # (rolling distro, no EOL)
     "ubuntu:jammy",  # 22.04 LTS (EOL 2027-04) (our EOL forced by Python 3.10 is 2026-10-04)
@@ -50,11 +49,11 @@ class Builder:
     def __init__(
         self,
         redirect_stdout: bool = False,
-        docker_build_args: Optional[Sequence[str]] = None,
+        docker_build_args: Sequence[str] | None = None,
     ):
         self.redirect_stdout = redirect_stdout
         self._docker_build_args = tuple(docker_build_args or ())
-        self.active_containers: Set[str] = set()
+        self.active_containers: set[str] = set()
         self._lock = threading.Lock()
         self._failed = False
 
@@ -168,7 +167,7 @@ class Builder:
 def run_builds(
     builder: Builder, dists: Collection[str], jobs: int = 1, skip_tests: bool = False
 ) -> None:
-    def sig(signum: int, _frame: Optional[FrameType]) -> None:
+    def sig(signum: int, _frame: FrameType | None) -> None:
         print("Caught SIGINT")
         builder.kill_containers()
 
diff --git a/scripts-dev/check_locked_deps_have_sdists.py b/scripts-dev/check_locked_deps_have_sdists.py
index cabe3b8de1..f035ecb644 100755
--- a/scripts-dev/check_locked_deps_have_sdists.py
+++ b/scripts-dev/check_locked_deps_have_sdists.py
@@ -21,7 +21,6 @@
 #
 import sys
 from pathlib import Path
-from typing import Dict, List
 
 import tomli
 
@@ -33,7 +32,7 @@ def main() -> None:
 
     # Poetry 1.3+ lockfile format:
     # There's a `files` inline table in each [[package]]
-    packages_to_assets: Dict[str, List[Dict[str, str]]] = {
+    packages_to_assets: dict[str, list[dict[str, str]]] = {
         package["name"]: package["files"] for package in lockfile_content["package"]
     }
 
diff --git a/scripts-dev/check_pydantic_models.py b/scripts-dev/check_pydantic_models.py
deleted file mode 100755
index 26a473a61b..0000000000
--- a/scripts-dev/check_pydantic_models.py
+++ /dev/null
@@ -1,478 +0,0 @@
-#! /usr/bin/env python
-#
-# This file is licensed under the Affero General Public License (AGPL) version 3.
-#
-# Copyright 2022 The Matrix.org Foundation C.I.C.
-# Copyright (C) 2023 New Vector, Ltd
-#
-# This program is free software: you can redistribute it and/or modify
-# it under the terms of the GNU Affero General Public License as
-# published by the Free Software Foundation, either version 3 of the
-# License, or (at your option) any later version.
-#
-# See the GNU Affero General Public License for more details:
-# <https://www.gnu.org/licenses/agpl-3.0.html>.
-#
-# Originally licensed under the Apache License, Version 2.0:
-# <http://www.apache.org/licenses/LICENSE-2.0>.
-#
-# [This file includes modifications made by New Vector Limited]
-#
-#
-"""
-A script which enforces that Synapse always uses strict types when defining a Pydantic
-model.
-
-Pydantic does not yet offer a strict mode, but it is planned for pydantic v2. See
-
-    https://github.com/pydantic/pydantic/issues/1098
-    https://pydantic-docs.helpmanual.io/blog/pydantic-v2/#strict-mode
-
-until then, this script is a best effort to stop us from introducing type coersion bugs
-(like the infamous stringy power levels fixed in room version 10).
-"""
-
-import argparse
-import contextlib
-import functools
-import importlib
-import logging
-import os
-import pkgutil
-import sys
-import textwrap
-import traceback
-import unittest.mock
-from contextlib import contextmanager
-from typing import (
-    Any,
-    Callable,
-    Dict,
-    Generator,
-    List,
-    Set,
-    Type,
-    TypeVar,
-)
-
-from parameterized import parameterized
-from typing_extensions import ParamSpec
-
-from synapse._pydantic_compat import (
-    BaseModel as PydanticBaseModel,
-    conbytes,
-    confloat,
-    conint,
-    constr,
-    get_args,
-)
-
-logger = logging.getLogger(__name__)
-
-CONSTRAINED_TYPE_FACTORIES_WITH_STRICT_FLAG: List[Callable] = [
-    constr,
-    conbytes,
-    conint,
-    confloat,
-]
-
-TYPES_THAT_PYDANTIC_WILL_COERCE_TO = [
-    str,
-    bytes,
-    int,
-    float,
-    bool,
-]
-
-
-P = ParamSpec("P")
-R = TypeVar("R")
-
-
-class ModelCheckerException(Exception):
-    """Dummy exception. Allows us to detect unwanted types during a module import."""
-
-
-class MissingStrictInConstrainedTypeException(ModelCheckerException):
-    factory_name: str
-
-    def __init__(self, factory_name: str):
-        self.factory_name = factory_name
-
-
-class FieldHasUnwantedTypeException(ModelCheckerException):
-    message: str
-
-    def __init__(self, message: str):
-        self.message = message
-
-
-def make_wrapper(factory: Callable[P, R]) -> Callable[P, R]:
-    """We patch `constr` and friends with wrappers that enforce strict=True."""
-
-    @functools.wraps(factory)
-    def wrapper(*args: P.args, **kwargs: P.kwargs) -> R:
-        if "strict" not in kwargs:
-            raise MissingStrictInConstrainedTypeException(factory.__name__)
-        if not kwargs["strict"]:
-            raise MissingStrictInConstrainedTypeException(factory.__name__)
-        return factory(*args, **kwargs)
-
-    return wrapper
-
-
-def field_type_unwanted(type_: Any) -> bool:
-    """Very rough attempt to detect if a type is unwanted as a Pydantic annotation.
-
-    At present, we exclude types which will coerce, or any generic type involving types
-    which will coerce."""
-    logger.debug("Is %s unwanted?")
-    if type_ in TYPES_THAT_PYDANTIC_WILL_COERCE_TO:
-        logger.debug("yes")
-        return True
-    logger.debug("Maybe. Subargs are %s", get_args(type_))
-    rv = any(field_type_unwanted(t) for t in get_args(type_))
-    logger.debug("Conclusion: %s %s unwanted", type_, "is" if rv else "is not")
-    return rv
-
-
-class PatchedBaseModel(PydanticBaseModel):
-    """A patched version of BaseModel that inspects fields after models are defined.
-
-    We complain loudly if we see an unwanted type.
-
-    Beware: ModelField.type_ is presumably private; this is likely to be very brittle.
-    """
-
-    @classmethod
-    def __init_subclass__(cls: Type[PydanticBaseModel], **kwargs: object):
-        for field in cls.__fields__.values():
-            # Note that field.type_ and field.outer_type are computed based on the
-            # annotation type, see pydantic.fields.ModelField._type_analysis
-            if field_type_unwanted(field.outer_type_):
-                # TODO: this only reports the first bad field. Can we find all bad ones
-                #  and report them all?
-                raise FieldHasUnwantedTypeException(
-                    f"{cls.__module__}.{cls.__qualname__} has field '{field.name}' "
-                    f"with unwanted type `{field.outer_type_}`"
-                )
-
-
-@contextmanager
-def monkeypatch_pydantic() -> Generator[None, None, None]:
-    """Patch pydantic with our snooping versions of BaseModel and the con* functions.
-
-    If the snooping functions see something they don't like, they'll raise a
-    ModelCheckingException instance.
-    """
-    with contextlib.ExitStack() as patches:
-        # Most Synapse code ought to import the patched objects directly from
-        # `pydantic`. But we also patch their containing modules `pydantic.main` and
-        # `pydantic.types` for completeness.
-        patch_basemodel = unittest.mock.patch(
-            "synapse._pydantic_compat.BaseModel", new=PatchedBaseModel
-        )
-        patches.enter_context(patch_basemodel)
-        for factory in CONSTRAINED_TYPE_FACTORIES_WITH_STRICT_FLAG:
-            wrapper: Callable = make_wrapper(factory)
-            patch = unittest.mock.patch(
-                f"synapse._pydantic_compat.{factory.__name__}", new=wrapper
-            )
-            patches.enter_context(patch)
-        yield
-
-
-def format_model_checker_exception(e: ModelCheckerException) -> str:
-    """Work out which line of code caused e. Format the line in a human-friendly way."""
-    # TODO. FieldHasUnwantedTypeException gives better error messages. Can we ditch the
-    #   patches of constr() etc, and instead inspect fields to look for ConstrainedStr
-    #   with strict=False? There is some difficulty with the inheritance hierarchy
-    #   because StrictStr < ConstrainedStr < str.
-    if isinstance(e, FieldHasUnwantedTypeException):
-        return e.message
-    elif isinstance(e, MissingStrictInConstrainedTypeException):
-        frame_summary = traceback.extract_tb(e.__traceback__)[-2]
-        return (
-            f"Missing `strict=True` from {e.factory_name}() call \n"
-            + traceback.format_list([frame_summary])[0].lstrip()
-        )
-    else:
-        raise ValueError(f"Unknown exception {e}") from e
-
-
-def lint() -> int:
-    """Try to import all of Synapse and see if we spot any Pydantic type coercions.
-
-    Print any problems, then return a status code suitable for sys.exit."""
-    failures = do_lint()
-    if failures:
-        print(f"Found {len(failures)} problem(s)")
-    for failure in sorted(failures):
-        print(failure)
-    return os.EX_DATAERR if failures else os.EX_OK
-
-
-def do_lint() -> Set[str]:
-    """Try to import all of Synapse and see if we spot any Pydantic type coercions."""
-    failures = set()
-
-    with monkeypatch_pydantic():
-        logger.debug("Importing synapse")
-        try:
-            # TODO: make "synapse" an argument so we can target this script at
-            # a subpackage
-            module = importlib.import_module("synapse")
-        except ModelCheckerException as e:
-            logger.warning("Bad annotation found when importing synapse")
-            failures.add(format_model_checker_exception(e))
-            return failures
-
-        try:
-            logger.debug("Fetching subpackages")
-            module_infos = list(
-                pkgutil.walk_packages(module.__path__, f"{module.__name__}.")
-            )
-        except ModelCheckerException as e:
-            logger.warning("Bad annotation found when looking for modules to import")
-            failures.add(format_model_checker_exception(e))
-            return failures
-
-        for module_info in module_infos:
-            logger.debug("Importing %s", module_info.name)
-            try:
-                importlib.import_module(module_info.name)
-            except ModelCheckerException as e:
-                logger.warning(
-                    "Bad annotation found when importing %s", module_info.name
-                )
-                failures.add(format_model_checker_exception(e))
-
-    return failures
-
-
-def run_test_snippet(source: str) -> None:
-    """Exec a snippet of source code in an isolated environment."""
-    # To emulate `source` being called at the top level of the module,
-    # the globals and locals we provide apparently have to be the same mapping.
-    #
-    # > Remember that at the module level, globals and locals are the same dictionary.
-    # > If exec gets two separate objects as globals and locals, the code will be
-    # > executed as if it were embedded in a class definition.
-    globals_: Dict[str, object]
-    locals_: Dict[str, object]
-    globals_ = locals_ = {}
-    exec(textwrap.dedent(source), globals_, locals_)
-
-
-class TestConstrainedTypesPatch(unittest.TestCase):
-    def test_expression_without_strict_raises(self) -> None:
-        with monkeypatch_pydantic(), self.assertRaises(ModelCheckerException):
-            run_test_snippet(
-                """
-                try:
-                    from pydantic.v1 import constr
-                except ImportError:
-                    from pydantic import constr
-                constr()
-                """
-            )
-
-    def test_called_as_module_attribute_raises(self) -> None:
-        with monkeypatch_pydantic(), self.assertRaises(ModelCheckerException):
-            run_test_snippet(
-                """
-                import pydantic
-                pydantic.constr()
-                """
-            )
-
-    def test_wildcard_import_raises(self) -> None:
-        with monkeypatch_pydantic(), self.assertRaises(ModelCheckerException):
-            run_test_snippet(
-                """
-                try:
-                    from pydantic.v1 import *
-                except ImportError:
-                    from pydantic import *
-                constr()
-                """
-            )
-
-    def test_alternative_import_raises(self) -> None:
-        with monkeypatch_pydantic(), self.assertRaises(ModelCheckerException):
-            run_test_snippet(
-                """
-                try:
-                    from pydantic.v1.types import constr
-                except ImportError:
-                    from pydantic.types import constr
-                constr()
-                """
-            )
-
-    def test_alternative_import_attribute_raises(self) -> None:
-        with monkeypatch_pydantic(), self.assertRaises(ModelCheckerException):
-            run_test_snippet(
-                """
-                try:
-                    from pydantic.v1 import types as pydantic_types
-                except ImportError:
-                    from pydantic import types as pydantic_types
-                pydantic_types.constr()
-                """
-            )
-
-    def test_kwarg_but_no_strict_raises(self) -> None:
-        with monkeypatch_pydantic(), self.assertRaises(ModelCheckerException):
-            run_test_snippet(
-                """
-                try:
-                    from pydantic.v1 import constr
-                except ImportError:
-                    from pydantic import constr
-                constr(min_length=10)
-                """
-            )
-
-    def test_kwarg_strict_False_raises(self) -> None:
-        with monkeypatch_pydantic(), self.assertRaises(ModelCheckerException):
-            run_test_snippet(
-                """
-                try:
-                    from pydantic.v1 import constr
-                except ImportError:
-                    from pydantic import constr
-                constr(strict=False)
-                """
-            )
-
-    def test_kwarg_strict_True_doesnt_raise(self) -> None:
-        with monkeypatch_pydantic():
-            run_test_snippet(
-                """
-                try:
-                    from pydantic.v1 import constr
-                except ImportError:
-                    from pydantic import constr
-                constr(strict=True)
-                """
-            )
-
-    def test_annotation_without_strict_raises(self) -> None:
-        with monkeypatch_pydantic(), self.assertRaises(ModelCheckerException):
-            run_test_snippet(
-                """
-                try:
-                    from pydantic.v1 import constr
-                except ImportError:
-                    from pydantic import constr
-                x: constr()
-                """
-            )
-
-    def test_field_annotation_without_strict_raises(self) -> None:
-        with monkeypatch_pydantic(), self.assertRaises(ModelCheckerException):
-            run_test_snippet(
-                """
-                try:
-                    from pydantic.v1 import BaseModel, conint
-                except ImportError:
-                    from pydantic import BaseModel, conint
-                class C:
-                    x: conint()
-                """
-            )
-
-
-class TestFieldTypeInspection(unittest.TestCase):
-    @parameterized.expand(
-        [
-            ("str",),
-            ("bytes"),
-            ("int",),
-            ("float",),
-            ("bool"),
-            ("Optional[str]",),
-            ("Union[None, str]",),
-            ("List[str]",),
-            ("List[List[str]]",),
-            ("Dict[StrictStr, str]",),
-            ("Dict[str, StrictStr]",),
-            ("TypedDict('D', x=int)",),
-        ]
-    )
-    def test_field_holding_unwanted_type_raises(self, annotation: str) -> None:
-        with monkeypatch_pydantic(), self.assertRaises(ModelCheckerException):
-            run_test_snippet(
-                f"""
-                from typing import *
-                try:
-                    from pydantic.v1 import *
-                except ImportError:
-                    from pydantic import *
-                class C(BaseModel):
-                    f: {annotation}
-                """
-            )
-
-    @parameterized.expand(
-        [
-            ("StrictStr",),
-            ("StrictBytes"),
-            ("StrictInt",),
-            ("StrictFloat",),
-            ("StrictBool"),
-            ("constr(strict=True, min_length=10)",),
-            ("Optional[StrictStr]",),
-            ("Union[None, StrictStr]",),
-            ("List[StrictStr]",),
-            ("List[List[StrictStr]]",),
-            ("Dict[StrictStr, StrictStr]",),
-            ("TypedDict('D', x=StrictInt)",),
-        ]
-    )
-    def test_field_holding_accepted_type_doesnt_raise(self, annotation: str) -> None:
-        with monkeypatch_pydantic():
-            run_test_snippet(
-                f"""
-                from typing import *
-                try:
-                    from pydantic.v1 import *
-                except ImportError:
-                    from pydantic import *
-                class C(BaseModel):
-                    f: {annotation}
-                """
-            )
-
-    def test_field_holding_str_raises_with_alternative_import(self) -> None:
-        with monkeypatch_pydantic(), self.assertRaises(ModelCheckerException):
-            run_test_snippet(
-                """
-                try:
-                    from pydantic.v1.main import BaseModel
-                except ImportError:
-                    from pydantic.main import BaseModel
-                class C(BaseModel):
-                    f: str
-                """
-            )
-
-
-parser = argparse.ArgumentParser()
-parser.add_argument("mode", choices=["lint", "test"], default="lint", nargs="?")
-parser.add_argument("-v", "--verbose", action="store_true")
-
-
-if __name__ == "__main__":
-    args = parser.parse_args(sys.argv[1:])
-    logging.basicConfig(
-        format="%(asctime)s %(name)s:%(lineno)d %(levelname)s %(message)s",
-        level=logging.DEBUG if args.verbose else logging.INFO,
-    )
-    # suppress logs we don't care about
-    logging.getLogger("xmlschema").setLevel(logging.WARNING)
-    if args.mode == "lint":
-        sys.exit(lint())
-    elif args.mode == "test":
-        unittest.main(argv=sys.argv[:1])
diff --git a/scripts-dev/check_schema_delta.py b/scripts-dev/check_schema_delta.py
index 454784c3ae..dd96c904bb 100755
--- a/scripts-dev/check_schema_delta.py
+++ b/scripts-dev/check_schema_delta.py
@@ -5,15 +5,19 @@
 # Also checks that schema deltas do not try and create or drop indices.
 
 import re
-from typing import Any, Dict, List
+from typing import Any
 
 import click
 import git
 
 SCHEMA_FILE_REGEX = re.compile(r"^synapse/storage/schema/(.*)/delta/(.*)/(.*)$")
-INDEX_CREATION_REGEX = re.compile(r"CREATE .*INDEX .*ON ([a-z_]+)", flags=re.IGNORECASE)
-INDEX_DELETION_REGEX = re.compile(r"DROP .*INDEX ([a-z_]+)", flags=re.IGNORECASE)
-TABLE_CREATION_REGEX = re.compile(r"CREATE .*TABLE ([a-z_]+)", flags=re.IGNORECASE)
+INDEX_CREATION_REGEX = re.compile(
+    r"CREATE .*INDEX .*ON ([a-z_0-9]+)", flags=re.IGNORECASE
+)
+INDEX_DELETION_REGEX = re.compile(r"DROP .*INDEX ([a-z_0-9]+)", flags=re.IGNORECASE)
+TABLE_CREATION_REGEX = re.compile(
+    r"CREATE .*TABLE.* ([a-z_0-9]+)\s*\(", flags=re.IGNORECASE
+)
 
 # The base branch we want to check against. We use the main development branch
 # on the assumption that is what we are developing against.
@@ -48,16 +52,16 @@ def main(force_colors: bool) -> None:
 
     r = repo.git.show(f"origin/{DEVELOP_BRANCH}:synapse/storage/schema/__init__.py")
 
-    locals: Dict[str, Any] = {}
+    locals: dict[str, Any] = {}
     exec(r, locals)
     current_schema_version = locals["SCHEMA_VERSION"]
 
-    diffs: List[git.Diff] = repo.remote().refs[DEVELOP_BRANCH].commit.diff(None)
+    diffs: list[git.Diff] = repo.remote().refs[DEVELOP_BRANCH].commit.diff(None)
 
     # Get the schema version of the local file to check against current schema on develop
     with open("synapse/storage/schema/__init__.py") as file:
         local_schema = file.read()
-    new_locals: Dict[str, Any] = {}
+    new_locals: dict[str, Any] = {}
     exec(local_schema, new_locals)
     local_schema_version = new_locals["SCHEMA_VERSION"]
 
@@ -173,11 +177,14 @@ def main(force_colors: bool) -> None:
                 clause = match.group()
 
                 click.secho(
-                    f"Found delta with index deletion: '{clause}' in {delta_file}\nThese should be in background updates.",
+                    f"Found delta with index deletion: '{clause}' in {delta_file}",
                     fg="red",
                     bold=True,
                     color=force_colors,
                 )
+                click.secho(
+                    " ↪ These should be in background updates.",
+                )
                 return_code = 1
 
             # Check for index creation, which is only allowed for tables we've
@@ -188,11 +195,14 @@ def main(force_colors: bool) -> None:
                 table_name = match.group(1)
                 if table_name not in created_tables:
                     click.secho(
-                        f"Found delta with index creation: '{clause}' in {delta_file}\nThese should be in background updates.",
+                        f"Found delta with index creation for existing table: '{clause}' in {delta_file}",
                         fg="red",
                         bold=True,
                         color=force_colors,
                     )
+                    click.secho(
+                        " ↪ These should be in background updates (or the table should be created in the same delta).",
+                    )
                     return_code = 1
 
     click.get_current_context().exit(return_code)
diff --git a/scripts-dev/federation_client.py b/scripts-dev/federation_client.py
index fb879ef555..0fefc23b22 100755
--- a/scripts-dev/federation_client.py
+++ b/scripts-dev/federation_client.py
@@ -43,7 +43,7 @@ import argparse
 import base64
 import json
 import sys
-from typing import Any, Dict, Mapping, Optional, Tuple, Union
+from typing import Any, Mapping
 from urllib import parse as urlparse
 
 import requests
@@ -103,12 +103,12 @@ def sign_json(
 
 
 def request(
-    method: Optional[str],
+    method: str | None,
     origin_name: str,
     origin_key: signedjson.types.SigningKey,
     destination: str,
     path: str,
-    content: Optional[str],
+    content: str | None,
     verify_tls: bool,
 ) -> requests.Response:
     if method is None:
@@ -147,7 +147,7 @@ def request(
     s = requests.Session()
     s.mount("matrix-federation://", MatrixConnectionAdapter())
 
-    headers: Dict[str, str] = {
+    headers: dict[str, str] = {
         "Authorization": authorization_headers[0],
     }
 
@@ -301,9 +301,9 @@ class MatrixConnectionAdapter(HTTPAdapter):
     def get_connection_with_tls_context(
         self,
         request: PreparedRequest,
-        verify: Optional[Union[bool, str]],
-        proxies: Optional[Mapping[str, str]] = None,
-        cert: Optional[Union[Tuple[str, str], str]] = None,
+        verify: bool | str | None,
+        proxies: Mapping[str, str] | None = None,
+        cert: tuple[str, str] | str | None = None,
     ) -> HTTPConnectionPool:
         # overrides the get_connection_with_tls_context() method in the base class
         parsed = urlparse.urlsplit(request.url)
@@ -326,7 +326,7 @@ class MatrixConnectionAdapter(HTTPAdapter):
         )
 
     @staticmethod
-    def _lookup(server_name: str) -> Tuple[str, int, str]:
+    def _lookup(server_name: str) -> tuple[str, int, str]:
         """
         Do an SRV lookup on a server name and return the host:port to connect to
         Given the server_name (after any .well-known lookup), return the host, port and
@@ -368,7 +368,7 @@ class MatrixConnectionAdapter(HTTPAdapter):
             return server_name, 8448, server_name
 
     @staticmethod
-    def _get_well_known(server_name: str) -> Optional[str]:
+    def _get_well_known(server_name: str) -> str | None:
         if ":" in server_name:
             # explicit port, or ipv6 literal. Either way, no .well-known
             return None
diff --git a/scripts-dev/gen_config_documentation.py b/scripts-dev/gen_config_documentation.py
index 9a49c07a34..aad25a4fc1 100755
--- a/scripts-dev/gen_config_documentation.py
+++ b/scripts-dev/gen_config_documentation.py
@@ -4,7 +4,7 @@
 import json
 import re
 import sys
-from typing import Any, Optional
+from typing import Any
 
 import yaml
 
@@ -259,17 +259,17 @@ def indent(text: str, first_line: bool = True) -> str:
     return text
 
 
-def em(s: Optional[str]) -> str:
+def em(s: str | None) -> str:
     """Add emphasis to text."""
     return f"*{s}*" if s else ""
 
 
-def a(s: Optional[str], suffix: str = " ") -> str:
+def a(s: str | None, suffix: str = " ") -> str:
     """Appends a space if the given string is not empty."""
     return s + suffix if s else ""
 
 
-def p(s: Optional[str], prefix: str = " ") -> str:
+def p(s: str | None, prefix: str = " ") -> str:
     """Prepend a space if the given string is not empty."""
     return prefix + s if s else ""
 
diff --git a/scripts-dev/lint.sh b/scripts-dev/lint.sh
index 7096100a3e..d5e10d4292 100755
--- a/scripts-dev/lint.sh
+++ b/scripts-dev/lint.sh
@@ -134,9 +134,6 @@ fi
 # Ensure the formatting of Rust code.
 cargo-fmt
 
-# Ensure all Pydantic models use strict types.
-./scripts-dev/check_pydantic_models.py lint
-
 # Ensure type hints are correct.
 mypy
 
diff --git a/scripts-dev/mypy_synapse_plugin.py b/scripts-dev/mypy_synapse_plugin.py
index e170aabdae..24794a1925 100644
--- a/scripts-dev/mypy_synapse_plugin.py
+++ b/scripts-dev/mypy_synapse_plugin.py
@@ -24,7 +24,7 @@ can crop up, e.g the cache descriptors.
 """
 
 import enum
-from typing import Callable, Mapping, Optional, Tuple, Type, Union
+from typing import Callable, Mapping
 
 import attr
 import mypy.types
@@ -68,18 +68,42 @@ PROMETHEUS_METRIC_MISSING_FROM_LIST_TO_CHECK = ErrorCode(
     category="per-homeserver-tenant-metrics",
 )
 
+PREFER_SYNAPSE_CLOCK_CALL_LATER = ErrorCode(
+    "call-later-not-tracked",
+    "Prefer using `synapse.util.Clock.call_later` instead of `reactor.callLater`",
+    category="synapse-reactor-clock",
+)
+
+PREFER_SYNAPSE_CLOCK_LOOPING_CALL = ErrorCode(
+    "prefer-synapse-clock-looping-call",
+    "Prefer using `synapse.util.Clock.looping_call` instead of `task.LoopingCall`",
+    category="synapse-reactor-clock",
+)
+
 PREFER_SYNAPSE_CLOCK_CALL_WHEN_RUNNING = ErrorCode(
     "prefer-synapse-clock-call-when-running",
-    "`synapse.util.Clock.call_when_running` should be used instead of `reactor.callWhenRunning`",
+    "Prefer using `synapse.util.Clock.call_when_running` instead of `reactor.callWhenRunning`",
     category="synapse-reactor-clock",
 )
 
 PREFER_SYNAPSE_CLOCK_ADD_SYSTEM_EVENT_TRIGGER = ErrorCode(
     "prefer-synapse-clock-add-system-event-trigger",
-    "`synapse.util.Clock.add_system_event_trigger` should be used instead of `reactor.addSystemEventTrigger`",
+    "Prefer using `synapse.util.Clock.add_system_event_trigger` instead of `reactor.addSystemEventTrigger`",
     category="synapse-reactor-clock",
 )
 
+MULTIPLE_INTERNAL_CLOCKS_CREATED = ErrorCode(
+    "multiple-internal-clocks",
+    "Only one instance of `clock.Clock` should be created",
+    category="synapse-reactor-clock",
+)
+
+UNTRACKED_BACKGROUND_PROCESS = ErrorCode(
+    "untracked-background-process",
+    "Prefer using `HomeServer.run_as_background_process` method over the bare `run_as_background_process`",
+    category="synapse-tracked-calls",
+)
+
 
 class Sentinel(enum.Enum):
     # defining a sentinel in this way allows mypy to correctly handle the
@@ -99,7 +123,7 @@ class ArgLocation:
     """
 
 
-prometheus_metric_fullname_to_label_arg_map: Mapping[str, Optional[ArgLocation]] = {
+prometheus_metric_fullname_to_label_arg_map: Mapping[str, ArgLocation | None] = {
     # `Collector` subclasses:
     "prometheus_client.metrics.MetricWrapperBase": ArgLocation("labelnames", 2),
     "prometheus_client.metrics.Counter": ArgLocation("labelnames", 2),
@@ -160,8 +184,8 @@ should be in the source code.
 
 # Unbound at this point because we don't know the mypy version yet.
 # This is set in the `plugin(...)` function below.
-MypyPydanticPluginClass: Type[Plugin]
-MypyZopePluginClass: Type[Plugin]
+MypyPydanticPluginClass: type[Plugin]
+MypyZopePluginClass: type[Plugin]
 
 
 class SynapsePlugin(Plugin):
@@ -187,7 +211,7 @@ class SynapsePlugin(Plugin):
 
     def get_base_class_hook(
         self, fullname: str
-    ) -> Optional[Callable[[ClassDefContext], None]]:
+    ) -> Callable[[ClassDefContext], None] | None:
         def _get_base_class_hook(ctx: ClassDefContext) -> None:
             # Run any `get_base_class_hook` checks from other plugins first.
             #
@@ -208,7 +232,7 @@ class SynapsePlugin(Plugin):
 
     def get_function_signature_hook(
         self, fullname: str
-    ) -> Optional[Callable[[FunctionSigContext], FunctionLike]]:
+    ) -> Callable[[FunctionSigContext], FunctionLike] | None:
         # Strip off the unique identifier for classes that are dynamically created inside
         # functions. ex. `synapse.metrics.jemalloc.JemallocCollector@185` (this is the line
         # number)
@@ -222,11 +246,23 @@ class SynapsePlugin(Plugin):
             # callback, let's just pass it in while we have it.
             return lambda ctx: check_prometheus_metric_instantiation(ctx, fullname)
 
+        if fullname == "twisted.internet.task.LoopingCall":
+            return check_looping_call
+
+        if fullname == "synapse.util.clock.Clock":
+            return check_clock_creation
+
+        if (
+            fullname
+            == "synapse.metrics.background_process_metrics.run_as_background_process"
+        ):
+            return check_background_process
+
         return None
 
     def get_method_signature_hook(
         self, fullname: str
-    ) -> Optional[Callable[[MethodSigContext], CallableType]]:
+    ) -> Callable[[MethodSigContext], CallableType] | None:
         if fullname.startswith(
             (
                 "synapse.util.caches.descriptors.CachedFunction.__call__",
@@ -241,6 +277,13 @@ class SynapsePlugin(Plugin):
         ):
             return check_is_cacheable_wrapper
 
+        if fullname in (
+            "twisted.internet.interfaces.IReactorTime.callLater",
+            "synapse.types.ISynapseThreadlessReactor.callLater",
+            "synapse.types.ISynapseReactor.callLater",
+        ):
+            return check_call_later
+
         if fullname in (
             "twisted.internet.interfaces.IReactorCore.callWhenRunning",
             "synapse.types.ISynapseThreadlessReactor.callWhenRunning",
@@ -258,6 +301,78 @@ class SynapsePlugin(Plugin):
         return None
 
 
+def check_clock_creation(ctx: FunctionSigContext) -> CallableType:
+    """
+    Ensure that the only `clock.Clock` instance is the one used by the `HomeServer`.
+    This is so that the `HomeServer` can cancel any tracked delayed or looping calls
+    during server shutdown.
+
+    Args:
+        ctx: The `FunctionSigContext` from mypy.
+    """
+    signature: CallableType = ctx.default_signature
+    ctx.api.fail(
+        "Expected the only `clock.Clock` instance to be the one used by the `HomeServer`. "
+        "This is so that the `HomeServer` can cancel any tracked delayed or looping calls "
+        "during server shutdown",
+        ctx.context,
+        code=MULTIPLE_INTERNAL_CLOCKS_CREATED,
+    )
+
+    return signature
+
+
+def check_call_later(ctx: MethodSigContext) -> CallableType:
+    """
+    Ensure that the `reactor.callLater` callsites aren't used.
+
+    `synapse.util.Clock.call_later` should always be used instead of `reactor.callLater`.
+    This is because the `synapse.util.Clock` tracks delayed calls in order to cancel any
+    outstanding calls during server shutdown. Delayed calls which are either short lived
+    (<~60s) or frequently called and can be tracked via other means could be candidates for
+    using `synapse.util.Clock.call_later` with `call_later_cancel_on_shutdown` set to
+    `False`. There shouldn't be a need to use `reactor.callLater` outside of tests or the
+    `Clock` class itself. If a need arises, you can use a type ignore comment to disable the
+    check, e.g. `# type: ignore[call-later-not-tracked]`.
+
+    Args:
+        ctx: The `FunctionSigContext` from mypy.
+    """
+    signature: CallableType = ctx.default_signature
+    ctx.api.fail(
+        "Expected all `reactor.callLater` calls to use `synapse.util.Clock.call_later` "
+        "instead. This is so that long lived calls can be tracked for cancellation during "
+        "server shutdown",
+        ctx.context,
+        code=PREFER_SYNAPSE_CLOCK_CALL_LATER,
+    )
+
+    return signature
+
+
+def check_looping_call(ctx: FunctionSigContext) -> CallableType:
+    """
+    Ensure that the `task.LoopingCall` callsites aren't used.
+
+    `synapse.util.Clock.looping_call` should always be used instead of `task.LoopingCall`.
+    `synapse.util.Clock` tracks looping calls in order to cancel any outstanding calls
+    during server shutdown.
+
+    Args:
+        ctx: The `FunctionSigContext` from mypy.
+    """
+    signature: CallableType = ctx.default_signature
+    ctx.api.fail(
+        "Expected all `task.LoopingCall` instances to use `synapse.util.Clock.looping_call` "
+        "instead. This is so that long lived calls can be tracked for cancellation during "
+        "server shutdown",
+        ctx.context,
+        code=PREFER_SYNAPSE_CLOCK_LOOPING_CALL,
+    )
+
+    return signature
+
+
 def check_call_when_running(ctx: MethodSigContext) -> CallableType:
     """
     Ensure that the `reactor.callWhenRunning` callsites aren't used.
@@ -312,6 +427,27 @@ def check_add_system_event_trigger(ctx: MethodSigContext) -> CallableType:
     return signature
 
 
+def check_background_process(ctx: FunctionSigContext) -> CallableType:
+    """
+    Ensure that calls to `run_as_background_process` use the `HomeServer` method.
+    This is so that the `HomeServer` can cancel any running background processes during
+    server shutdown.
+
+    Args:
+        ctx: The `FunctionSigContext` from mypy.
+    """
+    signature: CallableType = ctx.default_signature
+    ctx.api.fail(
+        "Prefer using `HomeServer.run_as_background_process` method over the bare "
+        "`run_as_background_process`. This is so that the `HomeServer` can cancel "
+        "any background processes during server shutdown",
+        ctx.context,
+        code=UNTRACKED_BACKGROUND_PROCESS,
+    )
+
+    return signature
+
+
 def analyze_prometheus_metric_classes(ctx: ClassDefContext) -> None:
     """
     Cross-check the list of Prometheus metric classes against the
@@ -585,7 +721,7 @@ def check_is_cacheable_wrapper(ctx: MethodSigContext) -> CallableType:
 
 def check_is_cacheable(
     signature: CallableType,
-    ctx: Union[MethodSigContext, FunctionSigContext],
+    ctx: MethodSigContext | FunctionSigContext,
 ) -> None:
     """
     Check if a callable returns a type which can be cached.
@@ -659,7 +795,7 @@ AT_CACHED_MUTABLE_RETURN = ErrorCode(
 
 def is_cacheable(
     rt: mypy.types.Type, signature: CallableType, verbose: bool
-) -> Tuple[bool, Optional[str]]:
+) -> tuple[bool, str | None]:
     """
     Check if a particular type is cachable.
 
@@ -769,7 +905,7 @@ def is_cacheable(
         return False, f"Don't know how to handle {type(rt).__qualname__} return type"
 
 
-def plugin(version: str) -> Type[SynapsePlugin]:
+def plugin(version: str) -> type[SynapsePlugin]:
     global MypyPydanticPluginClass, MypyZopePluginClass
     # This is the entry point of the plugin, and lets us deal with the fact
     # that the mypy plugin interface is *not* stable by looking at the version
diff --git a/scripts-dev/release.py b/scripts-dev/release.py
index 73a4e7b7a9..ba95a19382 100755
--- a/scripts-dev/release.py
+++ b/scripts-dev/release.py
@@ -32,11 +32,13 @@ import time
 import urllib.request
 from os import path
 from tempfile import TemporaryDirectory
-from typing import Any, List, Match, Optional, Union
+from typing import Any, Match
 
 import attr
 import click
 import git
+import github
+import github.Auth
 from click.exceptions import ClickException
 from git import GitCommandError, Repo
 from github import BadCredentialsException, Github
@@ -314,7 +316,10 @@ def _prepare() -> None:
     )
 
     print("Opening the changelog in your browser...")
-    print("Please ask #synapse-dev to give it a check.")
+    print(
+        "Please review it using the release notes review checklist: https://element-hq.github.io/synapse/develop/development/internal_documentation/release_notes_review_checklist.html"
+    )
+    print("And post it in #synapse-dev for cursory review from the team.")
     click.launch(
         f"https://github.com/element-hq/synapse/blob/{synapse_repo.active_branch.name}/CHANGES.md"
     )
@@ -322,11 +327,11 @@ def _prepare() -> None:
 
 @cli.command()
 @click.option("--gh-token", envvar=["GH_TOKEN", "GITHUB_TOKEN"])
-def tag(gh_token: Optional[str]) -> None:
+def tag(gh_token: str | None) -> None:
     _tag(gh_token)
 
 
-def _tag(gh_token: Optional[str]) -> None:
+def _tag(gh_token: str | None) -> None:
     """Tags the release and generates a draft GitHub release"""
 
     # Test that the GH Token is valid before continuing.
@@ -397,7 +402,7 @@ def _tag(gh_token: Optional[str]) -> None:
         return
 
     # Create a new draft release
-    gh = Github(gh_token)
+    gh = Github(auth=github.Auth.Token(token=gh_token))
     gh_repo = gh.get_repo("element-hq/synapse")
     release = gh_repo.create_git_release(
         tag=tag_name,
@@ -428,7 +433,7 @@ def _publish(gh_token: str) -> None:
 
     if gh_token:
         # Test that the GH Token is valid before continuing.
-        gh = Github(gh_token)
+        gh = Github(auth=github.Auth.Token(token=gh_token))
         gh.get_user()
 
     # Make sure we're in a git repo.
@@ -441,7 +446,7 @@ def _publish(gh_token: str) -> None:
         return
 
     # Publish the draft release
-    gh = Github(gh_token)
+    gh = Github(auth=github.Auth.Token(token=gh_token))
     gh_repo = gh.get_repo("element-hq/synapse")
     for release in gh_repo.get_releases():
         if release.title == tag_name:
@@ -466,11 +471,11 @@ def _publish(gh_token: str) -> None:
 
 @cli.command()
 @click.option("--gh-token", envvar=["GH_TOKEN", "GITHUB_TOKEN"], required=False)
-def upload(gh_token: Optional[str]) -> None:
+def upload(gh_token: str | None) -> None:
     _upload(gh_token)
 
 
-def _upload(gh_token: Optional[str]) -> None:
+def _upload(gh_token: str | None) -> None:
     """Upload release to pypi."""
 
     # Test that the GH Token is valid before continuing.
@@ -486,8 +491,13 @@ def _upload(gh_token: Optional[str]) -> None:
         click.echo(f"Tag {tag_name} ({tag.commit}) is not currently checked out!")
         click.get_current_context().abort()
 
+    if gh_token:
+        gh = Github(auth=github.Auth.Token(token=gh_token))
+    else:
+        # Use github anonymously.
+        gh = Github()
+
     # Query all the assets corresponding to this release.
-    gh = Github(gh_token)
     gh_repo = gh.get_repo("element-hq/synapse")
     gh_release = gh_repo.get_release(tag_name)
 
@@ -566,11 +576,11 @@ def _merge_into(repo: Repo, source: str, target: str) -> None:
 
 @cli.command()
 @click.option("--gh-token", envvar=["GH_TOKEN", "GITHUB_TOKEN"], required=False)
-def wait_for_actions(gh_token: Optional[str]) -> None:
+def wait_for_actions(gh_token: str | None) -> None:
     _wait_for_actions(gh_token)
 
 
-def _wait_for_actions(gh_token: Optional[str]) -> None:
+def _wait_for_actions(gh_token: str | None) -> None:
     # Test that the GH Token is valid before continuing.
     check_valid_gh_token(gh_token)
 
@@ -639,7 +649,16 @@ def _notify(message: str) -> None:
 
 
 @cli.command()
-def merge_back() -> None:
+# Although this option is not used, allow it anyways. Otherwise the user will
+# receive an error when providing it, which is annoying as other commands accept
+# it.
+@click.option(
+    "--gh-token",
+    "_gh_token",
+    envvar=["GH_TOKEN", "GITHUB_TOKEN"],
+    required=False,
+)
+def merge_back(_gh_token: str | None) -> None:
     _merge_back()
 
 
@@ -687,7 +706,16 @@ def _merge_back() -> None:
 
 
 @cli.command()
-def announce() -> None:
+# Although this option is not used, allow it anyways. Otherwise the user will
+# receive an error when providing it, which is annoying as other commands accept
+# it.
+@click.option(
+    "--gh-token",
+    "_gh_token",
+    envvar=["GH_TOKEN", "GITHUB_TOKEN"],
+    required=False,
+)
+def announce(_gh_token: str | None) -> None:
     _announce()
 
 
@@ -696,18 +724,31 @@ def _announce() -> None:
 
     current_version = get_package_version()
     tag_name = f"v{current_version}"
+    is_rc = "rc" in tag_name
+
+    release_text = f"""
+### Synapse {current_version} {"🧪" if is_rc else "🚀"}
 
-    click.echo(
-        f"""
 Hi everyone. Synapse {current_version} has just been released.
+"""
 
+    if "rc" in tag_name:
+        release_text += (
+            "\nThis is a release candidate. Please help us test it out "
+            "before the final release by deploying it to non-production environments, "
+            "and reporting any issues you find to "
+            "[the issue tracker](https://github.com/element-hq/synapse/issues). Thanks!\n"
+        )
+
+    release_text += f"""
 [notes](https://github.com/element-hq/synapse/releases/tag/{tag_name}) | \
 [docker](https://hub.docker.com/r/matrixdotorg/synapse/tags?name={tag_name}) | \
 [debs](https://packages.matrix.org/debian/) | \
 [pypi](https://pypi.org/project/matrix-synapse/{current_version}/)"""
-    )
 
-    if "rc" in tag_name:
+    click.echo(release_text)
+
+    if is_rc:
         click.echo(
             """
 Announce the RC in
@@ -732,7 +773,7 @@ Ask the designated people to do the blog and tweets."""
 def full(gh_token: str) -> None:
     if gh_token:
         # Test that the GH Token is valid before continuing.
-        gh = Github(gh_token)
+        gh = Github(auth=github.Auth.Token(token=gh_token))
         gh.get_user()
 
     click.echo("1. If this is a security release, read the security wiki page.")
@@ -801,12 +842,16 @@ def get_repo_and_check_clean_checkout(
         raise click.ClickException(
             f"{path} is not a git repository (expecting a {name} repository)."
         )
-    if repo.is_dirty():
-        raise click.ClickException(f"Uncommitted changes exist in {path}.")
+    while repo.is_dirty():
+        if not click.confirm(
+            f"Uncommitted changes exist in {path}. Commit or stash them. Ready to continue?"
+        ):
+            raise click.ClickException("Aborted.")
+
     return repo
 
 
-def check_valid_gh_token(gh_token: Optional[str]) -> None:
+def check_valid_gh_token(gh_token: str | None) -> None:
     """Check that a github token is valid, if supplied"""
 
     if not gh_token:
@@ -814,7 +859,7 @@ def check_valid_gh_token(gh_token: Optional[str]) -> None:
         return
 
     try:
-        gh = Github(gh_token)
+        gh = Github(auth=github.Auth.Token(token=gh_token))
 
         # We need to lookup name to trigger a request.
         _name = gh.get_user().name
@@ -822,7 +867,7 @@ def check_valid_gh_token(gh_token: Optional[str]) -> None:
         raise click.ClickException(f"Github credentials are bad: {e}")
 
 
-def find_ref(repo: git.Repo, ref_name: str) -> Optional[git.HEAD]:
+def find_ref(repo: git.Repo, ref_name: str) -> git.HEAD | None:
     """Find the branch/ref, looking first locally then in the remote."""
     if ref_name in repo.references:
         return repo.references[ref_name]
@@ -859,9 +904,9 @@ def get_changes_for_version(wanted_version: version.Version) -> str:
 
         # These are 0-based.
         start_line: int
-        end_line: Optional[int] = None  # Is none if its the last entry
+        end_line: int | None = None  # Is none if its the last entry
 
-    headings: List[VersionSection] = []
+    headings: list[VersionSection] = []
     for i, token in enumerate(tokens):
         # We look for level 1 headings (h1 tags).
         if token.type != "heading_open" or token.tag != "h1":
@@ -946,7 +991,7 @@ def build_dependabot_changelog(repo: Repo, current_version: version.Version) ->
     messages = []
     for commit in reversed(commits):
         if commit.author.name == "dependabot[bot]":
-            message: Union[str, bytes] = commit.message
+            message: str | bytes = commit.message
             if isinstance(message, bytes):
                 message = message.decode("utf-8")
             messages.append(message.split("\n", maxsplit=1)[0])
diff --git a/scripts-dev/schema_versions.py b/scripts-dev/schema_versions.py
index 5a79a43355..b3946ea7a1 100755
--- a/scripts-dev/schema_versions.py
+++ b/scripts-dev/schema_versions.py
@@ -38,7 +38,7 @@ import io
 import json
 import sys
 from collections import defaultdict
-from typing import Any, Dict, Iterator, Optional, Tuple
+from typing import Any, Iterator
 
 import git
 from packaging import version
@@ -57,7 +57,7 @@ SCHEMA_VERSION_FILES = (
 OLDEST_SHOWN_VERSION = version.parse("v1.0")
 
 
-def get_schema_versions(tag: git.Tag) -> Tuple[Optional[int], Optional[int]]:
+def get_schema_versions(tag: git.Tag) -> tuple[int | None, int | None]:
     """Get the schema and schema compat versions for a tag."""
     schema_version = None
     schema_compat_version = None
@@ -81,7 +81,7 @@ def get_schema_versions(tag: git.Tag) -> Tuple[Optional[int], Optional[int]]:
             # SCHEMA_COMPAT_VERSION is sometimes across multiple lines, the easist
             # thing to do is exec the code. Luckily it has only ever existed in
             # a file which imports nothing else from Synapse.
-            locals: Dict[str, Any] = {}
+            locals: dict[str, Any] = {}
             exec(schema_file.data_stream.read().decode("utf-8"), {}, locals)
             schema_version = locals["SCHEMA_VERSION"]
             schema_compat_version = locals.get("SCHEMA_COMPAT_VERSION")
diff --git a/stubs/sortedcontainers/sorteddict.pyi b/stubs/sortedcontainers/sorteddict.pyi
index 81f581b034..8616f8d4f7 100644
--- a/stubs/sortedcontainers/sorteddict.pyi
+++ b/stubs/sortedcontainers/sorteddict.pyi
@@ -7,20 +7,14 @@ from __future__ import annotations
 from typing import (
     Any,
     Callable,
-    Dict,
     Hashable,
     ItemsView,
     Iterable,
     Iterator,
     KeysView,
-    List,
     Mapping,
-    Optional,
     Sequence,
-    Tuple,
-    Type,
     TypeVar,
-    Union,
     ValuesView,
     overload,
 )
@@ -35,14 +29,14 @@ _VT_co = TypeVar("_VT_co", covariant=True)
 _SD = TypeVar("_SD", bound=SortedDict)
 _Key = Callable[[_T], Any]
 
-class SortedDict(Dict[_KT, _VT]):
+class SortedDict(dict[_KT, _VT]):
     @overload
     def __init__(self, **kwargs: _VT) -> None: ...
     @overload
     def __init__(self, __map: Mapping[_KT, _VT], **kwargs: _VT) -> None: ...
     @overload
     def __init__(
-        self, __iterable: Iterable[Tuple[_KT, _VT]], **kwargs: _VT
+        self, __iterable: Iterable[tuple[_KT, _VT]], **kwargs: _VT
     ) -> None: ...
     @overload
     def __init__(self, __key: _Key[_KT], **kwargs: _VT) -> None: ...
@@ -52,10 +46,10 @@ class SortedDict(Dict[_KT, _VT]):
     ) -> None: ...
     @overload
     def __init__(
-        self, __key: _Key[_KT], __iterable: Iterable[Tuple[_KT, _VT]], **kwargs: _VT
+        self, __key: _Key[_KT], __iterable: Iterable[tuple[_KT, _VT]], **kwargs: _VT
     ) -> None: ...
     @property
-    def key(self) -> Optional[_Key[_KT]]: ...
+    def key(self) -> _Key[_KT] | None: ...
     @property
     def iloc(self) -> SortedKeysView[_KT]: ...
     def clear(self) -> None: ...
@@ -83,10 +77,10 @@ class SortedDict(Dict[_KT, _VT]):
     @overload
     def pop(self, key: _KT) -> _VT: ...
     @overload
-    def pop(self, key: _KT, default: _T = ...) -> Union[_VT, _T]: ...
-    def popitem(self, index: int = ...) -> Tuple[_KT, _VT]: ...
-    def peekitem(self, index: int = ...) -> Tuple[_KT, _VT]: ...
-    def setdefault(self, key: _KT, default: Optional[_VT] = ...) -> _VT: ...
+    def pop(self, key: _KT, default: _T = ...) -> _VT | _T: ...
+    def popitem(self, index: int = ...) -> tuple[_KT, _VT]: ...
+    def peekitem(self, index: int = ...) -> tuple[_KT, _VT]: ...
+    def setdefault(self, key: _KT, default: _VT | None = ...) -> _VT: ...
     # Mypy now reports the first overload as an error, because typeshed widened the type
     # of `__map` to its internal `_typeshed.SupportsKeysAndGetItem` type in
     #   https://github.com/python/typeshed/pull/6653
@@ -102,16 +96,16 @@ class SortedDict(Dict[_KT, _VT]):
     # def update(self, **kwargs: _VT) -> None: ...
     def __reduce__(
         self,
-    ) -> Tuple[
-        Type[SortedDict[_KT, _VT]],
-        Tuple[Callable[[_KT], Any], List[Tuple[_KT, _VT]]],
+    ) -> tuple[
+        type[SortedDict[_KT, _VT]],
+        tuple[Callable[[_KT], Any], list[tuple[_KT, _VT]]],
     ]: ...
     def __repr__(self) -> str: ...
     def _check(self) -> None: ...
     def islice(
         self,
-        start: Optional[int] = ...,
-        stop: Optional[int] = ...,
+        start: int | None = ...,
+        stop: int | None = ...,
         reverse: bool = ...,
     ) -> Iterator[_KT]: ...
     def bisect_left(self, value: _KT) -> int: ...
@@ -121,20 +115,20 @@ class SortedKeysView(KeysView[_KT_co], Sequence[_KT_co]):
     @overload
     def __getitem__(self, index: int) -> _KT_co: ...
     @overload
-    def __getitem__(self, index: slice) -> List[_KT_co]: ...
-    def __delitem__(self, index: Union[int, slice]) -> None: ...
+    def __getitem__(self, index: slice) -> list[_KT_co]: ...
+    def __delitem__(self, index: int | slice) -> None: ...
 
-class SortedItemsView(ItemsView[_KT_co, _VT_co], Sequence[Tuple[_KT_co, _VT_co]]):
-    def __iter__(self) -> Iterator[Tuple[_KT_co, _VT_co]]: ...
+class SortedItemsView(ItemsView[_KT_co, _VT_co], Sequence[tuple[_KT_co, _VT_co]]):
+    def __iter__(self) -> Iterator[tuple[_KT_co, _VT_co]]: ...
     @overload
-    def __getitem__(self, index: int) -> Tuple[_KT_co, _VT_co]: ...
+    def __getitem__(self, index: int) -> tuple[_KT_co, _VT_co]: ...
     @overload
-    def __getitem__(self, index: slice) -> List[Tuple[_KT_co, _VT_co]]: ...
-    def __delitem__(self, index: Union[int, slice]) -> None: ...
+    def __getitem__(self, index: slice) -> list[tuple[_KT_co, _VT_co]]: ...
+    def __delitem__(self, index: int | slice) -> None: ...
 
 class SortedValuesView(ValuesView[_VT_co], Sequence[_VT_co]):
     @overload
     def __getitem__(self, index: int) -> _VT_co: ...
     @overload
-    def __getitem__(self, index: slice) -> List[_VT_co]: ...
-    def __delitem__(self, index: Union[int, slice]) -> None: ...
+    def __getitem__(self, index: slice) -> list[_VT_co]: ...
+    def __delitem__(self, index: int | slice) -> None: ...
diff --git a/stubs/sortedcontainers/sortedlist.pyi b/stubs/sortedcontainers/sortedlist.pyi
index 0e745c0a79..f5e056111b 100644
--- a/stubs/sortedcontainers/sortedlist.pyi
+++ b/stubs/sortedcontainers/sortedlist.pyi
@@ -9,14 +9,9 @@ from typing import (
     Callable,
     Iterable,
     Iterator,
-    List,
     MutableSequence,
-    Optional,
     Sequence,
-    Tuple,
-    Type,
     TypeVar,
-    Union,
     overload,
 )
 
@@ -32,20 +27,20 @@ class SortedList(MutableSequence[_T]):
     DEFAULT_LOAD_FACTOR: int = ...
     def __init__(
         self,
-        iterable: Optional[Iterable[_T]] = ...,
-        key: Optional[_Key[_T]] = ...,
+        iterable: Iterable[_T] | None = ...,
+        key: _Key[_T] | None = ...,
     ): ...
     # NB: currently mypy does not honour return type, see mypy #3307
     @overload
-    def __new__(cls: Type[_SL], iterable: None, key: None) -> _SL: ...
+    def __new__(cls: type[_SL], iterable: None, key: None) -> _SL: ...
     @overload
-    def __new__(cls: Type[_SL], iterable: None, key: _Key[_T]) -> SortedKeyList[_T]: ...
+    def __new__(cls: type[_SL], iterable: None, key: _Key[_T]) -> SortedKeyList[_T]: ...
     @overload
-    def __new__(cls: Type[_SL], iterable: Iterable[_T], key: None) -> _SL: ...
+    def __new__(cls: type[_SL], iterable: Iterable[_T], key: None) -> _SL: ...
     @overload
     def __new__(cls, iterable: Iterable[_T], key: _Key[_T]) -> SortedKeyList[_T]: ...
     @property
-    def key(self) -> Optional[Callable[[_T], Any]]: ...
+    def key(self) -> Callable[[_T], Any] | None: ...
     def _reset(self, load: int) -> None: ...
     def clear(self) -> None: ...
     def _clear(self) -> None: ...
@@ -60,15 +55,15 @@ class SortedList(MutableSequence[_T]):
     def _pos(self, idx: int) -> int: ...
     def _build_index(self) -> None: ...
     def __contains__(self, value: Any) -> bool: ...
-    def __delitem__(self, index: Union[int, slice]) -> None: ...
+    def __delitem__(self, index: int | slice) -> None: ...
     @overload
     def __getitem__(self, index: int) -> _T: ...
     @overload
-    def __getitem__(self, index: slice) -> List[_T]: ...
+    def __getitem__(self, index: slice) -> list[_T]: ...
     @overload
     def _getitem(self, index: int) -> _T: ...
     @overload
-    def _getitem(self, index: slice) -> List[_T]: ...
+    def _getitem(self, index: slice) -> list[_T]: ...
     @overload
     def __setitem__(self, index: int, value: _T) -> None: ...
     @overload
@@ -79,8 +74,8 @@ class SortedList(MutableSequence[_T]):
     def reverse(self) -> None: ...
     def islice(
         self,
-        start: Optional[int] = ...,
-        stop: Optional[int] = ...,
+        start: int | None = ...,
+        stop: int | None = ...,
         reverse: bool = ...,
     ) -> Iterator[_T]: ...
     def _islice(
@@ -93,9 +88,9 @@ class SortedList(MutableSequence[_T]):
     ) -> Iterator[_T]: ...
     def irange(
         self,
-        minimum: Optional[int] = ...,
-        maximum: Optional[int] = ...,
-        inclusive: Tuple[bool, bool] = ...,
+        minimum: int | None = ...,
+        maximum: int | None = ...,
+        inclusive: tuple[bool, bool] = ...,
         reverse: bool = ...,
     ) -> Iterator[_T]: ...
     def bisect_left(self, value: _T) -> int: ...
@@ -110,7 +105,7 @@ class SortedList(MutableSequence[_T]):
     def insert(self, index: int, value: _T) -> None: ...
     def pop(self, index: int = ...) -> _T: ...
     def index(
-        self, value: _T, start: Optional[int] = ..., stop: Optional[int] = ...
+        self, value: _T, start: int | None = ..., stop: int | None = ...
     ) -> int: ...
     def __add__(self: _SL, other: Iterable[_T]) -> _SL: ...
     def __radd__(self: _SL, other: Iterable[_T]) -> _SL: ...
@@ -129,10 +124,10 @@ class SortedList(MutableSequence[_T]):
 
 class SortedKeyList(SortedList[_T]):
     def __init__(
-        self, iterable: Optional[Iterable[_T]] = ..., key: _Key[_T] = ...
+        self, iterable: Iterable[_T] | None = ..., key: _Key[_T] = ...
     ) -> None: ...
     def __new__(
-        cls, iterable: Optional[Iterable[_T]] = ..., key: _Key[_T] = ...
+        cls, iterable: Iterable[_T] | None = ..., key: _Key[_T] = ...
     ) -> SortedKeyList[_T]: ...
     @property
     def key(self) -> Callable[[_T], Any]: ...
@@ -149,16 +144,16 @@ class SortedKeyList(SortedList[_T]):
     def _delete(self, pos: int, idx: int) -> None: ...
     def irange(
         self,
-        minimum: Optional[int] = ...,
-        maximum: Optional[int] = ...,
-        inclusive: Tuple[bool, bool] = ...,
+        minimum: int | None = ...,
+        maximum: int | None = ...,
+        inclusive: tuple[bool, bool] = ...,
         reverse: bool = ...,
     ) -> Iterator[_T]: ...
     def irange_key(
         self,
-        min_key: Optional[Any] = ...,
-        max_key: Optional[Any] = ...,
-        inclusive: Tuple[bool, bool] = ...,
+        min_key: Any | None = ...,
+        max_key: Any | None = ...,
+        inclusive: tuple[bool, bool] = ...,
         reserve: bool = ...,
     ) -> Iterator[_T]: ...
     def bisect_left(self, value: _T) -> int: ...
@@ -173,7 +168,7 @@ class SortedKeyList(SortedList[_T]):
     def copy(self: _SKL) -> _SKL: ...
     def __copy__(self: _SKL) -> _SKL: ...
     def index(
-        self, value: _T, start: Optional[int] = ..., stop: Optional[int] = ...
+        self, value: _T, start: int | None = ..., stop: int | None = ...
     ) -> int: ...
     def __add__(self: _SKL, other: Iterable[_T]) -> _SKL: ...
     def __radd__(self: _SKL, other: Iterable[_T]) -> _SKL: ...
diff --git a/stubs/sortedcontainers/sortedset.pyi b/stubs/sortedcontainers/sortedset.pyi
index 6db11eacbe..da2696b262 100644
--- a/stubs/sortedcontainers/sortedset.pyi
+++ b/stubs/sortedcontainers/sortedset.pyi
@@ -10,15 +10,9 @@ from typing import (
     Hashable,
     Iterable,
     Iterator,
-    List,
     MutableSet,
-    Optional,
     Sequence,
-    Set,
-    Tuple,
-    Type,
     TypeVar,
-    Union,
     overload,
 )
 
@@ -32,21 +26,19 @@ _Key = Callable[[_T], Any]
 class SortedSet(MutableSet[_T], Sequence[_T]):
     def __init__(
         self,
-        iterable: Optional[Iterable[_T]] = ...,
-        key: Optional[_Key[_T]] = ...,
+        iterable: Iterable[_T] | None = ...,
+        key: _Key[_T] | None = ...,
     ) -> None: ...
     @classmethod
-    def _fromset(
-        cls, values: Set[_T], key: Optional[_Key[_T]] = ...
-    ) -> SortedSet[_T]: ...
+    def _fromset(cls, values: set[_T], key: _Key[_T] | None = ...) -> SortedSet[_T]: ...
     @property
-    def key(self) -> Optional[_Key[_T]]: ...
+    def key(self) -> _Key[_T] | None: ...
     def __contains__(self, value: Any) -> bool: ...
     @overload
     def __getitem__(self, index: int) -> _T: ...
     @overload
-    def __getitem__(self, index: slice) -> List[_T]: ...
-    def __delitem__(self, index: Union[int, slice]) -> None: ...
+    def __getitem__(self, index: slice) -> list[_T]: ...
+    def __delitem__(self, index: int | slice) -> None: ...
     def __eq__(self, other: Any) -> bool: ...
     def __ne__(self, other: Any) -> bool: ...
     def __lt__(self, other: Iterable[_T]) -> bool: ...
@@ -66,53 +58,49 @@ class SortedSet(MutableSet[_T], Sequence[_T]):
     def _discard(self, value: _T) -> None: ...
     def pop(self, index: int = ...) -> _T: ...
     def remove(self, value: _T) -> None: ...
-    def difference(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def __sub__(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def difference_update(
-        self, *iterables: Iterable[_S]
-    ) -> SortedSet[Union[_T, _S]]: ...
-    def __isub__(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def intersection(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def __and__(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def __rand__(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def intersection_update(
-        self, *iterables: Iterable[_S]
-    ) -> SortedSet[Union[_T, _S]]: ...
-    def __iand__(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def symmetric_difference(self, other: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def __xor__(self, other: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def __rxor__(self, other: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
+    def difference(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def __sub__(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def difference_update(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def __isub__(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def intersection(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def __and__(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def __rand__(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def intersection_update(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def __iand__(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def symmetric_difference(self, other: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def __xor__(self, other: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def __rxor__(self, other: Iterable[_S]) -> SortedSet[_T | _S]: ...
     def symmetric_difference_update(
         self, other: Iterable[_S]
-    ) -> SortedSet[Union[_T, _S]]: ...
-    def __ixor__(self, other: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def union(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def __or__(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def __ror__(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def update(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def __ior__(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def _update(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
+    ) -> SortedSet[_T | _S]: ...
+    def __ixor__(self, other: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def union(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def __or__(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def __ror__(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def update(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def __ior__(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def _update(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
     def __reduce__(
         self,
-    ) -> Tuple[Type[SortedSet[_T]], Set[_T], Callable[[_T], Any]]: ...
+    ) -> tuple[type[SortedSet[_T]], set[_T], Callable[[_T], Any]]: ...
     def __repr__(self) -> str: ...
     def _check(self) -> None: ...
     def bisect_left(self, value: _T) -> int: ...
     def bisect_right(self, value: _T) -> int: ...
     def islice(
         self,
-        start: Optional[int] = ...,
-        stop: Optional[int] = ...,
+        start: int | None = ...,
+        stop: int | None = ...,
         reverse: bool = ...,
     ) -> Iterator[_T]: ...
     def irange(
         self,
-        minimum: Optional[_T] = ...,
-        maximum: Optional[_T] = ...,
-        inclusive: Tuple[bool, bool] = ...,
+        minimum: _T | None = ...,
+        maximum: _T | None = ...,
+        inclusive: tuple[bool, bool] = ...,
         reverse: bool = ...,
     ) -> Iterator[_T]: ...
     def index(
-        self, value: _T, start: Optional[int] = ..., stop: Optional[int] = ...
+        self, value: _T, start: int | None = ..., stop: int | None = ...
     ) -> int: ...
     def _reset(self, load: int) -> None: ...
diff --git a/stubs/txredisapi.pyi b/stubs/txredisapi.pyi
index c9a4114b1e..50ab54037a 100644
--- a/stubs/txredisapi.pyi
+++ b/stubs/txredisapi.pyi
@@ -15,7 +15,7 @@
 
 """Contains *incomplete* type hints for txredisapi."""
 
-from typing import Any, List, Optional, Type, Union
+from typing import Any
 
 from twisted.internet import protocol
 from twisted.internet.defer import Deferred
@@ -29,8 +29,8 @@ class RedisProtocol(protocol.Protocol):
         self,
         key: str,
         value: Any,
-        expire: Optional[int] = None,
-        pexpire: Optional[int] = None,
+        expire: int | None = None,
+        pexpire: int | None = None,
         only_if_not_exists: bool = False,
         only_if_exists: bool = False,
     ) -> "Deferred[None]": ...
@@ -38,8 +38,8 @@ class RedisProtocol(protocol.Protocol):
 
 class SubscriberProtocol(RedisProtocol):
     def __init__(self, *args: object, **kwargs: object): ...
-    password: Optional[str]
-    def subscribe(self, channels: Union[str, List[str]]) -> "Deferred[None]": ...
+    password: str | None
+    def subscribe(self, channels: str | list[str]) -> "Deferred[None]": ...
     def connectionMade(self) -> None: ...
     # type-ignore: twisted.internet.protocol.Protocol provides a default argument for
     # `reason`. txredisapi's LineReceiver Protocol doesn't. But that's fine: it's what's
@@ -49,12 +49,12 @@ class SubscriberProtocol(RedisProtocol):
 def lazyConnection(
     host: str = ...,
     port: int = ...,
-    dbid: Optional[int] = ...,
+    dbid: int | None = ...,
     reconnect: bool = ...,
     charset: str = ...,
-    password: Optional[str] = ...,
-    connectTimeout: Optional[int] = ...,
-    replyTimeout: Optional[int] = ...,
+    password: str | None = ...,
+    connectTimeout: int | None = ...,
+    replyTimeout: int | None = ...,
     convertNumbers: bool = ...,
 ) -> RedisProtocol: ...
 
@@ -69,19 +69,19 @@ class UnixConnectionHandler(ConnectionHandler): ...
 class RedisFactory(protocol.ReconnectingClientFactory):
     continueTrying: bool
     handler: ConnectionHandler
-    pool: List[RedisProtocol]
-    replyTimeout: Optional[int]
+    pool: list[RedisProtocol]
+    replyTimeout: int | None
     def __init__(
         self,
         uuid: str,
-        dbid: Optional[int],
+        dbid: int | None,
         poolsize: int,
         isLazy: bool = False,
-        handler: Type = ConnectionHandler,
+        handler: type = ConnectionHandler,
         charset: str = "utf-8",
-        password: Optional[str] = None,
-        replyTimeout: Optional[int] = None,
-        convertNumbers: Optional[int] = True,
+        password: str | None = None,
+        replyTimeout: int | None = None,
+        convertNumbers: int | None = True,
     ): ...
     def buildProtocol(self, addr: IAddress) -> RedisProtocol: ...
 
diff --git a/synapse/__init__.py b/synapse/__init__.py
index 3bd1b3307e..2bed060878 100644
--- a/synapse/__init__.py
+++ b/synapse/__init__.py
@@ -24,7 +24,7 @@
 
 import os
 import sys
-from typing import Any, Dict
+from typing import Any
 
 from PIL import ImageFile
 
@@ -39,8 +39,8 @@ ImageFile.LOAD_TRUNCATED_IMAGES = True
 # Note that we use an (unneeded) variable here so that pyupgrade doesn't nuke the
 # if-statement completely.
 py_version = sys.version_info
-if py_version < (3, 9):
-    print("Synapse requires Python 3.9 or above.")
+if py_version < (3, 10):
+    print("Synapse requires Python 3.10 or above.")
     sys.exit(1)
 
 # Allow using the asyncio reactor via env var.
@@ -70,7 +70,7 @@ try:
     from canonicaljson import register_preserialisation_callback
     from immutabledict import immutabledict
 
-    def _immutabledict_cb(d: immutabledict) -> Dict[str, Any]:
+    def _immutabledict_cb(d: immutabledict) -> dict[str, Any]:
         try:
             return d._dict
         except Exception:
diff --git a/synapse/_pydantic_compat.py b/synapse/_pydantic_compat.py
deleted file mode 100644
index a520c0e897..0000000000
--- a/synapse/_pydantic_compat.py
+++ /dev/null
@@ -1,104 +0,0 @@
-#
-# This file is licensed under the Affero General Public License (AGPL) version 3.
-#
-# Copyright 2023 Maxwell G <maxwell@gtmx.me>
-# Copyright (C) 2023 New Vector, Ltd
-#
-# This program is free software: you can redistribute it and/or modify
-# it under the terms of the GNU Affero General Public License as
-# published by the Free Software Foundation, either version 3 of the
-# License, or (at your option) any later version.
-#
-# See the GNU Affero General Public License for more details:
-# <https://www.gnu.org/licenses/agpl-3.0.html>.
-#
-# Originally licensed under the Apache License, Version 2.0:
-# <http://www.apache.org/licenses/LICENSE-2.0>.
-#
-# [This file includes modifications made by New Vector Limited]
-#
-#
-
-from typing import TYPE_CHECKING
-
-from packaging.version import Version
-
-try:
-    from pydantic import __version__ as pydantic_version
-except ImportError:
-    import importlib.metadata
-
-    pydantic_version = importlib.metadata.version("pydantic")
-
-HAS_PYDANTIC_V2: bool = Version(pydantic_version).major == 2
-
-if TYPE_CHECKING or HAS_PYDANTIC_V2:
-    from pydantic.v1 import (
-        AnyHttpUrl,
-        BaseModel,
-        Extra,
-        Field,
-        FilePath,
-        MissingError,
-        PydanticValueError,
-        StrictBool,
-        StrictInt,
-        StrictStr,
-        ValidationError,
-        conbytes,
-        confloat,
-        conint,
-        constr,
-        parse_obj_as,
-        root_validator,
-        validator,
-    )
-    from pydantic.v1.error_wrappers import ErrorWrapper
-    from pydantic.v1.typing import get_args
-else:
-    from pydantic import (
-        AnyHttpUrl,
-        BaseModel,
-        Extra,
-        Field,
-        FilePath,
-        MissingError,
-        PydanticValueError,
-        StrictBool,
-        StrictInt,
-        StrictStr,
-        ValidationError,
-        conbytes,
-        confloat,
-        conint,
-        constr,
-        parse_obj_as,
-        root_validator,
-        validator,
-    )
-    from pydantic.error_wrappers import ErrorWrapper
-    from pydantic.typing import get_args
-
-__all__ = (
-    "HAS_PYDANTIC_V2",
-    "AnyHttpUrl",
-    "BaseModel",
-    "constr",
-    "conbytes",
-    "conint",
-    "confloat",
-    "ErrorWrapper",
-    "Extra",
-    "Field",
-    "FilePath",
-    "get_args",
-    "MissingError",
-    "parse_obj_as",
-    "PydanticValueError",
-    "StrictBool",
-    "StrictInt",
-    "StrictStr",
-    "ValidationError",
-    "validator",
-    "root_validator",
-)
diff --git a/synapse/_scripts/export_signing_key.py b/synapse/_scripts/export_signing_key.py
index 690115aabe..bab5953802 100755
--- a/synapse/_scripts/export_signing_key.py
+++ b/synapse/_scripts/export_signing_key.py
@@ -22,13 +22,13 @@
 import argparse
 import sys
 import time
-from typing import NoReturn, Optional
+from typing import NoReturn
 
 from signedjson.key import encode_verify_key_base64, get_verify_key, read_signing_keys
 from signedjson.types import VerifyKey
 
 
-def exit(status: int = 0, message: Optional[str] = None) -> NoReturn:
+def exit(status: int = 0, message: str | None = None) -> NoReturn:
     if message:
         print(message, file=sys.stderr)
     sys.exit(status)
diff --git a/synapse/_scripts/generate_workers_map.py b/synapse/_scripts/generate_workers_map.py
index 8878e364e2..3fa27b4b2a 100755
--- a/synapse/_scripts/generate_workers_map.py
+++ b/synapse/_scripts/generate_workers_map.py
@@ -25,7 +25,7 @@ import logging
 import re
 from collections import defaultdict
 from dataclasses import dataclass
-from typing import Dict, Iterable, Optional, Pattern, Set, Tuple
+from typing import Iterable, Pattern
 
 import yaml
 
@@ -46,7 +46,7 @@ logger = logging.getLogger("generate_workers_map")
 class MockHomeserver(HomeServer):
     DATASTORE_CLASS = DataStore
 
-    def __init__(self, config: HomeServerConfig, worker_app: Optional[str]) -> None:
+    def __init__(self, config: HomeServerConfig, worker_app: str | None) -> None:
         super().__init__(config.server.server_name, config=config)
         self.config.worker.worker_app = worker_app
 
@@ -65,7 +65,7 @@ class EndpointDescription:
 
     # The category of this endpoint. Is read from the `CATEGORY` constant in the servlet
     # class.
-    category: Optional[str]
+    category: str | None
 
     # TODO:
     #  - does it need to be routed based on a stream writer config?
@@ -81,7 +81,7 @@ class EnumerationResource(HttpServer):
     """
 
     def __init__(self, is_worker: bool) -> None:
-        self.registrations: Dict[Tuple[str, str], EndpointDescription] = {}
+        self.registrations: dict[tuple[str, str], EndpointDescription] = {}
         self._is_worker = is_worker
 
     def register_paths(
@@ -115,7 +115,7 @@ class EnumerationResource(HttpServer):
 
 def get_registered_paths_for_hs(
     hs: HomeServer,
-) -> Dict[Tuple[str, str], EndpointDescription]:
+) -> dict[tuple[str, str], EndpointDescription]:
     """
     Given a homeserver, get all registered endpoints and their descriptions.
     """
@@ -141,8 +141,8 @@ def get_registered_paths_for_hs(
 
 
 def get_registered_paths_for_default(
-    worker_app: Optional[str], base_config: HomeServerConfig
-) -> Dict[Tuple[str, str], EndpointDescription]:
+    worker_app: str | None, base_config: HomeServerConfig
+) -> dict[tuple[str, str], EndpointDescription]:
     """
     Given the name of a worker application and a base homeserver configuration,
     returns:
@@ -157,15 +157,20 @@ def get_registered_paths_for_default(
     # TODO We only do this to avoid an error, but don't need the database etc
     hs.setup()
     registered_paths = get_registered_paths_for_hs(hs)
-    hs.cleanup()
+    # NOTE: a more robust implementation would properly shutdown/cleanup each server
+    # to avoid resource buildup.
+    # However, the call to `shutdown` is `async` so it would require additional complexity here.
+    # We are intentionally skipping this cleanup because this is a short-lived, one-off
+    # utility script where the simpler approach is sufficient and we shouldn't run into
+    # any resource buildup issues.
 
     return registered_paths
 
 
 def elide_http_methods_if_unconflicting(
-    registrations: Dict[Tuple[str, str], EndpointDescription],
-    all_possible_registrations: Dict[Tuple[str, str], EndpointDescription],
-) -> Dict[Tuple[str, str], EndpointDescription]:
+    registrations: dict[tuple[str, str], EndpointDescription],
+    all_possible_registrations: dict[tuple[str, str], EndpointDescription],
+) -> dict[tuple[str, str], EndpointDescription]:
     """
     Elides HTTP methods (by replacing them with `*`) if all possible registered methods
     can be handled by the worker whose registration map is `registrations`.
@@ -175,13 +180,13 @@ def elide_http_methods_if_unconflicting(
     """
 
     def paths_to_methods_dict(
-        methods_and_paths: Iterable[Tuple[str, str]],
-    ) -> Dict[str, Set[str]]:
+        methods_and_paths: Iterable[tuple[str, str]],
+    ) -> dict[str, set[str]]:
         """
         Given (method, path) pairs, produces a dict from path to set of methods
         available at that path.
         """
-        result: Dict[str, Set[str]] = {}
+        result: dict[str, set[str]] = {}
         for method, path in methods_and_paths:
             result.setdefault(path, set()).add(method)
         return result
@@ -205,8 +210,8 @@ def elide_http_methods_if_unconflicting(
 
 
 def simplify_path_regexes(
-    registrations: Dict[Tuple[str, str], EndpointDescription],
-) -> Dict[Tuple[str, str], EndpointDescription]:
+    registrations: dict[tuple[str, str], EndpointDescription],
+) -> dict[tuple[str, str], EndpointDescription]:
     """
     Simplify all the path regexes for the dict of endpoint descriptions,
     so that we don't use the Python-specific regex extensions
@@ -265,8 +270,8 @@ def main() -> None:
 
     # TODO SSO endpoints (pick_idp etc) NOT REGISTERED BY THIS SCRIPT
 
-    categories_to_methods_and_paths: Dict[
-        Optional[str], Dict[Tuple[str, str], EndpointDescription]
+    categories_to_methods_and_paths: dict[
+        str | None, dict[tuple[str, str], EndpointDescription]
     ] = defaultdict(dict)
 
     for (method, path), desc in elided_worker_paths.items():
@@ -277,8 +282,8 @@ def main() -> None:
 
 
 def print_category(
-    category_name: Optional[str],
-    elided_worker_paths: Dict[Tuple[str, str], EndpointDescription],
+    category_name: str | None,
+    elided_worker_paths: dict[tuple[str, str], EndpointDescription],
 ) -> None:
     """
     Prints out a category, in documentation page style.
diff --git a/synapse/_scripts/hash_password.py b/synapse/_scripts/hash_password.py
index 2b7d3585cb..ae475b8490 100755
--- a/synapse/_scripts/hash_password.py
+++ b/synapse/_scripts/hash_password.py
@@ -73,8 +73,18 @@ def main() -> None:
 
     pw = unicodedata.normalize("NFKC", password)
 
+    bytes_to_hash = pw.encode("utf8") + password_pepper.encode("utf8")
+    if len(bytes_to_hash) > 72:
+        # bcrypt only looks at the first 72 bytes
+        print(
+            f"Password + pepper is too long ({len(bytes_to_hash)} bytes); truncating to 72 bytes for bcrypt. "
+            "This is expected behaviour and will not affect a user's ability to log in. 72 bytes is "
+            "sufficient entropy for a password."
+        )
+        bytes_to_hash = bytes_to_hash[:72]
+
     hashed = bcrypt.hashpw(
-        pw.encode("utf8") + password_pepper.encode("utf8"),
+        bytes_to_hash,
         bcrypt.gensalt(bcrypt_rounds),
     ).decode("ascii")
 
diff --git a/synapse/_scripts/register_new_matrix_user.py b/synapse/_scripts/register_new_matrix_user.py
index 4897fa94b0..1ce8221218 100644
--- a/synapse/_scripts/register_new_matrix_user.py
+++ b/synapse/_scripts/register_new_matrix_user.py
@@ -26,7 +26,7 @@ import hashlib
 import hmac
 import logging
 import sys
-from typing import Any, Callable, Dict, Optional
+from typing import Any, Callable
 
 import requests
 import yaml
@@ -54,7 +54,7 @@ def request_registration(
     server_location: str,
     shared_secret: str,
     admin: bool = False,
-    user_type: Optional[str] = None,
+    user_type: str | None = None,
     _print: Callable[[str], None] = print,
     exit: Callable[[int], None] = sys.exit,
     exists_ok: bool = False,
@@ -123,13 +123,13 @@ def register_new_user(
     password: str,
     server_location: str,
     shared_secret: str,
-    admin: Optional[bool],
-    user_type: Optional[str],
+    admin: bool | None,
+    user_type: str | None,
     exists_ok: bool = False,
 ) -> None:
     if not user:
         try:
-            default_user: Optional[str] = getpass.getuser()
+            default_user: str | None = getpass.getuser()
         except Exception:
             default_user = None
 
@@ -262,7 +262,7 @@ def main() -> None:
 
     args = parser.parse_args()
 
-    config: Optional[Dict[str, Any]] = None
+    config: dict[str, Any] | None = None
     if "config" in args and args.config:
         config = yaml.safe_load(args.config)
 
@@ -350,7 +350,7 @@ def _read_file(file_path: Any, config_path: str) -> str:
         sys.exit(1)
 
 
-def _find_client_listener(config: Dict[str, Any]) -> Optional[str]:
+def _find_client_listener(config: dict[str, Any]) -> str | None:
     # try to find a listener in the config. Returns a host:port pair
     for listener in config.get("listeners", []):
         if listener.get("type") != "http" or listener.get("tls", False):
diff --git a/synapse/_scripts/review_recent_signups.py b/synapse/_scripts/review_recent_signups.py
index 0ff7fae567..d760a84bf2 100644
--- a/synapse/_scripts/review_recent_signups.py
+++ b/synapse/_scripts/review_recent_signups.py
@@ -23,7 +23,6 @@ import argparse
 import sys
 import time
 from datetime import datetime
-from typing import List
 
 import attr
 
@@ -50,15 +49,15 @@ class ReviewConfig(RootConfig):
 class UserInfo:
     user_id: str
     creation_ts: int
-    emails: List[str] = attr.Factory(list)
-    private_rooms: List[str] = attr.Factory(list)
-    public_rooms: List[str] = attr.Factory(list)
-    ips: List[str] = attr.Factory(list)
+    emails: list[str] = attr.Factory(list)
+    private_rooms: list[str] = attr.Factory(list)
+    public_rooms: list[str] = attr.Factory(list)
+    ips: list[str] = attr.Factory(list)
 
 
 def get_recent_users(
     txn: LoggingTransaction, since_ms: int, exclude_app_service: bool
-) -> List[UserInfo]:
+) -> list[UserInfo]:
     """Fetches recently registered users and some info on them."""
 
     sql = """
diff --git a/synapse/_scripts/synapse_port_db.py b/synapse/_scripts/synapse_port_db.py
index b0a067edcb..1806e42d90 100755
--- a/synapse/_scripts/synapse_port_db.py
+++ b/synapse/_scripts/synapse_port_db.py
@@ -33,15 +33,10 @@ from typing import (
     Any,
     Awaitable,
     Callable,
-    Dict,
     Generator,
     Iterable,
-    List,
     NoReturn,
     Optional,
-    Set,
-    Tuple,
-    Type,
     TypedDict,
     TypeVar,
     cast,
@@ -98,7 +93,6 @@ from synapse.storage.databases.state.bg_updates import StateBackgroundUpdateStor
 from synapse.storage.engines import create_engine
 from synapse.storage.prepare_database import prepare_database
 from synapse.types import ISynapseReactor
-from synapse.util import SYNAPSE_VERSION
 
 # Cast safety: Twisted does some naughty magic which replaces the
 # twisted.internet.reactor module with a Reactor instance at runtime.
@@ -239,14 +233,14 @@ IGNORED_BACKGROUND_UPDATES = {
 
 # Error returned by the run function. Used at the top-level part of the script to
 # handle errors and return codes.
-end_error: Optional[str] = None
+end_error: str | None = None
 # The exec_info for the error, if any. If error is defined but not exec_info the script
 # will show only the error message without the stacktrace, if exec_info is defined but
 # not the error then the script will show nothing outside of what's printed in the run
 # function. If both are defined, the script will print both the error and the stacktrace.
-end_error_exec_info: Optional[
-    Tuple[Type[BaseException], BaseException, TracebackType]
-] = None
+end_error_exec_info: tuple[type[BaseException], BaseException, TracebackType] | None = (
+    None
+)
 
 R = TypeVar("R")
 
@@ -282,8 +276,8 @@ class Store(
     def execute(self, f: Callable[..., R], *args: Any, **kwargs: Any) -> Awaitable[R]:
         return self.db_pool.runInteraction(f.__name__, f, *args, **kwargs)
 
-    def execute_sql(self, sql: str, *args: object) -> Awaitable[List[Tuple]]:
-        def r(txn: LoggingTransaction) -> List[Tuple]:
+    def execute_sql(self, sql: str, *args: object) -> Awaitable[list[tuple]]:
+        def r(txn: LoggingTransaction) -> list[tuple]:
             txn.execute(sql, args)
             return txn.fetchall()
 
@@ -293,8 +287,8 @@ class Store(
         self,
         txn: LoggingTransaction,
         table: str,
-        headers: List[str],
-        rows: List[Tuple],
+        headers: list[str],
+        rows: list[tuple],
         override_system_value: bool = False,
     ) -> None:
         sql = "INSERT INTO %s (%s) %s VALUES (%s)" % (
@@ -325,14 +319,13 @@ class MockHomeserver(HomeServer):
             hostname=config.server.server_name,
             config=config,
             reactor=reactor,
-            version_string=f"Synapse/{SYNAPSE_VERSION}",
         )
 
 
 class Porter:
     def __init__(
         self,
-        sqlite_config: Dict[str, Any],
+        sqlite_config: dict[str, Any],
         progress: "Progress",
         batch_size: int,
         hs: HomeServer,
@@ -342,7 +335,7 @@ class Porter:
         self.batch_size = batch_size
         self.hs = hs
 
-    async def setup_table(self, table: str) -> Tuple[str, int, int, int, int]:
+    async def setup_table(self, table: str) -> tuple[str, int, int, int, int]:
         if table in APPEND_ONLY_TABLES:
             # It's safe to just carry on inserting.
             row = await self.postgres_store.db_pool.simple_select_one(
@@ -405,10 +398,10 @@ class Porter:
 
         return table, already_ported, total_to_port, forward_chunk, backward_chunk
 
-    async def get_table_constraints(self) -> Dict[str, Set[str]]:
+    async def get_table_constraints(self) -> dict[str, set[str]]:
         """Returns a map of tables that have foreign key constraints to tables they depend on."""
 
-        def _get_constraints(txn: LoggingTransaction) -> Dict[str, Set[str]]:
+        def _get_constraints(txn: LoggingTransaction) -> dict[str, set[str]]:
             # We can pull the information about foreign key constraints out from
             # the postgres schema tables.
             sql = """
@@ -424,7 +417,7 @@ class Porter:
             """
             txn.execute(sql)
 
-            results: Dict[str, Set[str]] = {}
+            results: dict[str, set[str]] = {}
             for table, foreign_table in txn:
                 results.setdefault(table, set()).add(foreign_table)
             return results
@@ -492,7 +485,7 @@ class Porter:
 
             def r(
                 txn: LoggingTransaction,
-            ) -> Tuple[Optional[List[str]], List[Tuple], List[Tuple]]:
+            ) -> tuple[list[str] | None, list[tuple], list[tuple]]:
                 forward_rows = []
                 backward_rows = []
                 if do_forward[0]:
@@ -509,7 +502,7 @@ class Porter:
 
                 if forward_rows or backward_rows:
                     assert txn.description is not None
-                    headers: Optional[List[str]] = [
+                    headers: list[str] | None = [
                         column[0] for column in txn.description
                     ]
                 else:
@@ -576,7 +569,7 @@ class Porter:
 
         while True:
 
-            def r(txn: LoggingTransaction) -> Tuple[List[str], List[Tuple]]:
+            def r(txn: LoggingTransaction) -> tuple[list[str], list[tuple]]:
                 txn.execute(select, (forward_chunk, self.batch_size))
                 rows = txn.fetchall()
                 assert txn.description is not None
@@ -958,7 +951,7 @@ class Porter:
             self.progress.set_state("Copying to postgres")
 
             constraints = await self.get_table_constraints()
-            tables_ported = set()  # type: Set[str]
+            tables_ported = set()  # type: set[str]
 
             while tables_to_port_info_map:
                 # Pulls out all tables that are still to be ported and which
@@ -997,8 +990,8 @@ class Porter:
             reactor.stop()
 
     def _convert_rows(
-        self, table: str, headers: List[str], rows: List[Tuple]
-    ) -> List[Tuple]:
+        self, table: str, headers: list[str], rows: list[tuple]
+    ) -> list[tuple]:
         bool_col_names = BOOLEAN_COLUMNS.get(table, [])
 
         bool_cols = [i for i, h in enumerate(headers) if h in bool_col_names]
@@ -1032,7 +1025,7 @@ class Porter:
 
         return outrows
 
-    async def _setup_sent_transactions(self) -> Tuple[int, int, int]:
+    async def _setup_sent_transactions(self) -> tuple[int, int, int]:
         # Only save things from the last day
         yesterday = int(time.time() * 1000) - 86400000
 
@@ -1044,7 +1037,7 @@ class Porter:
             ")"
         )
 
-        def r(txn: LoggingTransaction) -> Tuple[List[str], List[Tuple]]:
+        def r(txn: LoggingTransaction) -> tuple[list[str], list[tuple]]:
             txn.execute(select)
             rows = txn.fetchall()
             assert txn.description is not None
@@ -1114,14 +1107,14 @@ class Porter:
         self, table: str, forward_chunk: int, backward_chunk: int
     ) -> int:
         frows = cast(
-            List[Tuple[int]],
+            list[tuple[int]],
             await self.sqlite_store.execute_sql(
                 "SELECT count(*) FROM %s WHERE rowid >= ?" % (table,), forward_chunk
             ),
         )
 
         brows = cast(
-            List[Tuple[int]],
+            list[tuple[int]],
             await self.sqlite_store.execute_sql(
                 "SELECT count(*) FROM %s WHERE rowid <= ?" % (table,), backward_chunk
             ),
@@ -1138,7 +1131,7 @@ class Porter:
 
     async def _get_total_count_to_port(
         self, table: str, forward_chunk: int, backward_chunk: int
-    ) -> Tuple[int, int]:
+    ) -> tuple[int, int]:
         remaining, done = await make_deferred_yieldable(
             defer.gatherResults(
                 [
@@ -1159,9 +1152,7 @@ class Porter:
         return done, remaining + done
 
     async def _setup_state_group_id_seq(self) -> None:
-        curr_id: Optional[
-            int
-        ] = await self.sqlite_store.db_pool.simple_select_one_onecol(
+        curr_id: int | None = await self.sqlite_store.db_pool.simple_select_one_onecol(
             table="state_groups", keyvalues={}, retcol="MAX(id)", allow_none=True
         )
 
@@ -1223,7 +1214,7 @@ class Porter:
     async def _setup_sequence(
         self,
         sequence_name: str,
-        stream_id_tables: Iterable[Tuple[str, str]],
+        stream_id_tables: Iterable[tuple[str, str]],
     ) -> None:
         """Set a sequence to the correct value."""
         current_stream_ids = []
@@ -1278,10 +1269,10 @@ class Porter:
 
         await self.postgres_store.db_pool.runInteraction("_setup_%s" % (seq_name,), r)
 
-    async def _pg_get_serial_sequence(self, table: str, column: str) -> Optional[str]:
+    async def _pg_get_serial_sequence(self, table: str, column: str) -> str | None:
         """Returns the name of the postgres sequence associated with a column, or NULL."""
 
-        def r(txn: LoggingTransaction) -> Optional[str]:
+        def r(txn: LoggingTransaction) -> str | None:
             txn.execute("SELECT pg_get_serial_sequence('%s', '%s')" % (table, column))
             result = txn.fetchone()
             if not result:
@@ -1293,9 +1284,9 @@ class Porter:
         )
 
     async def _setup_auth_chain_sequence(self) -> None:
-        curr_chain_id: Optional[
-            int
-        ] = await self.sqlite_store.db_pool.simple_select_one_onecol(
+        curr_chain_id: (
+            int | None
+        ) = await self.sqlite_store.db_pool.simple_select_one_onecol(
             table="event_auth_chains",
             keyvalues={},
             retcol="MAX(chain_id)",
@@ -1333,7 +1324,7 @@ class Progress:
     """Used to report progress of the port"""
 
     def __init__(self) -> None:
-        self.tables: Dict[str, TableProgress] = {}
+        self.tables: dict[str, TableProgress] = {}
 
         self.start_time = int(time.time())
 
diff --git a/synapse/_scripts/synctl.py b/synapse/_scripts/synctl.py
index 2e2aa27a17..29ab955c45 100755
--- a/synapse/_scripts/synctl.py
+++ b/synapse/_scripts/synctl.py
@@ -30,7 +30,7 @@ import signal
 import subprocess
 import sys
 import time
-from typing import Iterable, NoReturn, Optional, TextIO
+from typing import Iterable, NoReturn, TextIO
 
 import yaml
 
@@ -135,7 +135,7 @@ def start(pidfile: str, app: str, config_files: Iterable[str], daemonize: bool)
         return False
 
 
-def stop(pidfile: str, app: str) -> Optional[int]:
+def stop(pidfile: str, app: str) -> int | None:
     """Attempts to kill a synapse worker from the pidfile.
     Args:
         pidfile: path to file containing worker's pid
diff --git a/synapse/_scripts/update_synapse_database.py b/synapse/_scripts/update_synapse_database.py
index caaecda161..ce32f47d63 100644
--- a/synapse/_scripts/update_synapse_database.py
+++ b/synapse/_scripts/update_synapse_database.py
@@ -28,11 +28,9 @@ import yaml
 from twisted.internet import defer, reactor as reactor_
 
 from synapse.config.homeserver import HomeServerConfig
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.server import HomeServer
 from synapse.storage import DataStore
 from synapse.types import ISynapseReactor
-from synapse.util import SYNAPSE_VERSION
 
 # Cast safety: Twisted does some naughty magic which replaces the
 # twisted.internet.reactor module with a Reactor instance at runtime.
@@ -48,12 +46,10 @@ class MockHomeserver(HomeServer):
             hostname=config.server.server_name,
             config=config,
             reactor=reactor,
-            version_string=f"Synapse/{SYNAPSE_VERSION}",
         )
 
 
 def run_background_updates(hs: HomeServer) -> None:
-    server_name = hs.hostname
     main = hs.get_datastores().main
     state = hs.get_datastores().state
 
@@ -67,9 +63,8 @@ def run_background_updates(hs: HomeServer) -> None:
     def run() -> None:
         # Apply all background updates on the database.
         defer.ensureDeferred(
-            run_as_background_process(
+            hs.run_as_background_process(
                 "background_updates",
-                server_name,
                 run_background_updates,
             )
         )
diff --git a/synapse/api/auth/__init__.py b/synapse/api/auth/__init__.py
index d253938329..201c295f06 100644
--- a/synapse/api/auth/__init__.py
+++ b/synapse/api/auth/__init__.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import TYPE_CHECKING, Optional, Protocol, Tuple
+from typing import TYPE_CHECKING, Protocol
 
 from prometheus_client import Histogram
 
@@ -51,7 +51,7 @@ class Auth(Protocol):
         room_id: str,
         requester: Requester,
         allow_departed_users: bool = False,
-    ) -> Tuple[str, Optional[str]]:
+    ) -> tuple[str, str | None]:
         """Check if the user is in the room, or was at some point.
         Args:
             room_id: The room to check.
@@ -190,7 +190,7 @@ class Auth(Protocol):
 
     async def check_user_in_room_or_world_readable(
         self, room_id: str, requester: Requester, allow_departed_users: bool = False
-    ) -> Tuple[str, Optional[str]]:
+    ) -> tuple[str, str | None]:
         """Checks that the user is or was in the room or the room is world
         readable. If it isn't then an exception is raised.
 
diff --git a/synapse/api/auth/base.py b/synapse/api/auth/base.py
index 76c8c71628..ff876b9d22 100644
--- a/synapse/api/auth/base.py
+++ b/synapse/api/auth/base.py
@@ -19,7 +19,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, Optional, Tuple
+from typing import TYPE_CHECKING
 
 from netaddr import IPAddress
 
@@ -64,7 +64,7 @@ class BaseAuth:
         room_id: str,
         requester: Requester,
         allow_departed_users: bool = False,
-    ) -> Tuple[str, Optional[str]]:
+    ) -> tuple[str, str | None]:
         """Check if the user is in the room, or was at some point.
         Args:
             room_id: The room to check.
@@ -114,7 +114,7 @@ class BaseAuth:
     @trace
     async def check_user_in_room_or_world_readable(
         self, room_id: str, requester: Requester, allow_departed_users: bool = False
-    ) -> Tuple[str, Optional[str]]:
+    ) -> tuple[str, str | None]:
         """Checks that the user is or was in the room or the room is world
         readable. If it isn't then an exception is raised.
 
@@ -294,7 +294,7 @@ class BaseAuth:
     @cancellable
     async def get_appservice_user(
         self, request: Request, access_token: str
-    ) -> Optional[Requester]:
+    ) -> Requester | None:
         """
         Given a request, reads the request parameters to determine:
         - whether it's an application service that's making this request
@@ -302,12 +302,9 @@ class BaseAuth:
           (the user_id URI parameter allows an application service to masquerade
           any applicable user in its namespace)
         - what device the application service should be treated as controlling
-          (the device_id[^1] URI parameter allows an application service to masquerade
+          (the device_id URI parameter allows an application service to masquerade
           as any device that exists for the relevant user)
 
-        [^1] Unstable and provided by MSC3202.
-             Must use `org.matrix.msc3202.device_id` in place of `device_id` for now.
-
         Returns:
             the application service `Requester` of that request
 
@@ -319,7 +316,8 @@ class BaseAuth:
         - The returned device ID, if present, has been checked to be a valid device ID
           for the returned user ID.
         """
-        DEVICE_ID_ARG_NAME = b"org.matrix.msc3202.device_id"
+        # TODO: We can drop unstable support after 2026-01-01 (couple months after stable support)
+        UNSTABLE_DEVICE_ID_ARG_NAME = b"org.matrix.msc3202.device_id"
 
         app_service = self.store.get_app_service_by_token(access_token)
         if app_service is None:
@@ -341,13 +339,11 @@ class BaseAuth:
         else:
             effective_user_id = app_service.sender
 
-        effective_device_id: Optional[str] = None
-
-        if (
-            self.hs.config.experimental.msc3202_device_masquerading_enabled
-            and DEVICE_ID_ARG_NAME in request.args
-        ):
-            effective_device_id = request.args[DEVICE_ID_ARG_NAME][0].decode("utf8")
+        effective_device_id_args = request.args.get(
+            b"device_id", request.args.get(UNSTABLE_DEVICE_ID_ARG_NAME)
+        )
+        if effective_device_id_args:
+            effective_device_id = effective_device_id_args[0].decode("utf8")
             # We only just set this so it can't be None!
             assert effective_device_id is not None
             device_opt = await self.store.get_device(
@@ -359,6 +355,8 @@ class BaseAuth:
                     f"Application service trying to use a device that doesn't exist ('{effective_device_id}' for {effective_user_id})",
                     Codes.UNKNOWN_DEVICE,
                 )
+        else:
+            effective_device_id = None
 
         return create_requester(
             effective_user_id, app_service=app_service, device_id=effective_device_id
diff --git a/synapse/api/auth/mas.py b/synapse/api/auth/mas.py
index ef82ea9cc7..e422a1e5c5 100644
--- a/synapse/api/auth/mas.py
+++ b/synapse/api/auth/mas.py
@@ -13,17 +13,19 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, Optional, Set
+from typing import TYPE_CHECKING
 from urllib.parse import urlencode
 
-from synapse._pydantic_compat import (
+from pydantic import (
+    AnyHttpUrl,
     BaseModel,
-    Extra,
+    ConfigDict,
     StrictBool,
     StrictInt,
     StrictStr,
     ValidationError,
 )
+
 from synapse.api.auth.base import BaseAuth
 from synapse.api.errors import (
     AuthError,
@@ -33,7 +35,6 @@ from synapse.api.errors import (
     UnrecognizedRequestError,
 )
 from synapse.http.site import SynapseRequest
-from synapse.logging.context import PreserveLoggingContext
 from synapse.logging.opentracing import (
     active_span,
     force_tracing,
@@ -64,8 +65,7 @@ STABLE_SCOPE_MATRIX_DEVICE_PREFIX = "urn:matrix:client:device:"
 
 
 class ServerMetadata(BaseModel):
-    class Config:
-        extra = Extra.allow
+    model_config = ConfigDict(extra="allow")
 
     issuer: StrictStr
     account_management_uri: StrictStr
@@ -74,14 +74,12 @@ class ServerMetadata(BaseModel):
 class IntrospectionResponse(BaseModel):
     retrieved_at_ms: StrictInt
     active: StrictBool
-    scope: Optional[StrictStr]
-    username: Optional[StrictStr]
-    sub: Optional[StrictStr]
-    device_id: Optional[StrictStr]
-    expires_in: Optional[StrictInt]
-
-    class Config:
-        extra = Extra.allow
+    scope: StrictStr | None = None
+    username: StrictStr | None = None
+    sub: StrictStr | None = None
+    device_id: StrictStr | None = None
+    expires_in: StrictInt | None = None
+    model_config = ConfigDict(extra="allow")
 
     def get_scope_set(self) -> set[str]:
         if not self.scope:
@@ -149,11 +147,33 @@ class MasDelegatedAuth(BaseAuth):
 
     @property
     def _metadata_url(self) -> str:
-        return f"{self._config.endpoint.rstrip('/')}/.well-known/openid-configuration"
+        return str(
+            AnyHttpUrl.build(
+                scheme=self._config.endpoint.scheme,
+                username=self._config.endpoint.username,
+                password=self._config.endpoint.password,
+                host=self._config.endpoint.host or "",
+                port=self._config.endpoint.port,
+                path=".well-known/openid-configuration",
+                query=None,
+                fragment=None,
+            )
+        )
 
     @property
     def _introspection_endpoint(self) -> str:
-        return f"{self._config.endpoint.rstrip('/')}/oauth2/introspect"
+        return str(
+            AnyHttpUrl.build(
+                scheme=self._config.endpoint.scheme,
+                username=self._config.endpoint.username,
+                password=self._config.endpoint.password,
+                host=self._config.endpoint.host or "",
+                port=self._config.endpoint.port,
+                path="oauth2/introspect",
+                query=None,
+                fragment=None,
+            )
+        )
 
     async def _load_metadata(self) -> ServerMetadata:
         response = await self._http_client.get_json(self._metadata_url)
@@ -229,13 +249,12 @@ class MasDelegatedAuth(BaseAuth):
         try:
             with start_active_span("mas-introspect-token"):
                 inject_request_headers(raw_headers)
-                with PreserveLoggingContext():
-                    resp_body = await self._rust_http_client.post(
-                        url=self._introspection_endpoint,
-                        response_limit=1 * 1024 * 1024,
-                        headers=raw_headers,
-                        request_body=body,
-                    )
+                resp_body = await self._rust_http_client.post(
+                    url=self._introspection_endpoint,
+                    response_limit=1 * 1024 * 1024,
+                    headers=raw_headers,
+                    request_body=body,
+                )
         except HttpResponseException as e:
             end_time = self._clock.time()
             introspection_response_timer.labels(
@@ -371,7 +390,7 @@ class MasDelegatedAuth(BaseAuth):
             # We only allow a single device_id in the scope, so we find them all in the
             # scope list, and raise if there are more than one. The OIDC server should be
             # the one enforcing valid scopes, so we raise a 500 if we find an invalid scope.
-            device_ids: Set[str] = set()
+            device_ids: set[str] = set()
             for tok in scope:
                 if tok.startswith(UNSTABLE_SCOPE_MATRIX_DEVICE_PREFIX):
                     device_ids.add(tok[len(UNSTABLE_SCOPE_MATRIX_DEVICE_PREFIX) :])
diff --git a/synapse/api/auth/msc3861_delegated.py b/synapse/api/auth/msc3861_delegated.py
index 11a89dd3ed..7999d6e459 100644
--- a/synapse/api/auth/msc3861_delegated.py
+++ b/synapse/api/auth/msc3861_delegated.py
@@ -20,7 +20,7 @@
 #
 import logging
 from dataclasses import dataclass
-from typing import TYPE_CHECKING, Any, Callable, Dict, List, Optional, Set
+from typing import TYPE_CHECKING, Any, Callable
 from urllib.parse import urlencode
 
 from authlib.oauth2 import ClientAuth
@@ -38,7 +38,6 @@ from synapse.api.errors import (
     UnrecognizedRequestError,
 )
 from synapse.http.site import SynapseRequest
-from synapse.logging.context import PreserveLoggingContext
 from synapse.logging.opentracing import (
     active_span,
     force_tracing,
@@ -71,7 +70,7 @@ STABLE_SCOPE_MATRIX_DEVICE_PREFIX = "urn:matrix:client:device:"
 SCOPE_SYNAPSE_ADMIN = "urn:synapse:admin:*"
 
 
-def scope_to_list(scope: str) -> List[str]:
+def scope_to_list(scope: str) -> list[str]:
     """Convert a scope string to a list of scope tokens"""
     return scope.strip().split(" ")
 
@@ -97,31 +96,31 @@ class IntrospectionResult:
         absolute_expiry_ms = expires_in * 1000 + self.retrieved_at_ms
         return now_ms < absolute_expiry_ms
 
-    def get_scope_list(self) -> List[str]:
+    def get_scope_list(self) -> list[str]:
         value = self._inner.get("scope")
         if not isinstance(value, str):
             return []
         return scope_to_list(value)
 
-    def get_sub(self) -> Optional[str]:
+    def get_sub(self) -> str | None:
         value = self._inner.get("sub")
         if not isinstance(value, str):
             return None
         return value
 
-    def get_username(self) -> Optional[str]:
+    def get_username(self) -> str | None:
         value = self._inner.get("username")
         if not isinstance(value, str):
             return None
         return value
 
-    def get_name(self) -> Optional[str]:
+    def get_name(self) -> str | None:
         value = self._inner.get("name")
         if not isinstance(value, str):
             return None
         return value
 
-    def get_device_id(self) -> Optional[str]:
+    def get_device_id(self) -> str | None:
         value = self._inner.get("device_id")
         if value is not None and not isinstance(value, str):
             raise AuthError(
@@ -175,7 +174,7 @@ class MSC3861DelegatedAuth(BaseAuth):
         self._clock = hs.get_clock()
         self._http_client = hs.get_proxied_http_client()
         self._hostname = hs.hostname
-        self._admin_token: Callable[[], Optional[str]] = self._config.admin_token
+        self._admin_token: Callable[[], str | None] = self._config.admin_token
         self._force_tracing_for_users = hs.config.tracing.force_tracing_for_users
 
         self._rust_http_client = HttpClient(
@@ -248,7 +247,7 @@ class MSC3861DelegatedAuth(BaseAuth):
         metadata = await self._issuer_metadata.get()
         return metadata.issuer or self._config.issuer
 
-    async def account_management_url(self) -> Optional[str]:
+    async def account_management_url(self) -> str | None:
         """
         Get the configured account management URL
 
@@ -265,7 +264,7 @@ class MSC3861DelegatedAuth(BaseAuth):
             logger.warning("Failed to load metadata:", exc_info=True)
             return None
 
-    async def auth_metadata(self) -> Dict[str, Any]:
+    async def auth_metadata(self) -> dict[str, Any]:
         """
         Returns the auth metadata dict
         """
@@ -304,7 +303,7 @@ class MSC3861DelegatedAuth(BaseAuth):
         # By default, we shouldn't cache the result unless we know it's valid
         cache_context.should_cache = False
         introspection_endpoint = await self._introspection_endpoint()
-        raw_headers: Dict[str, str] = {
+        raw_headers: dict[str, str] = {
             "Content-Type": "application/x-www-form-urlencoded",
             "Accept": "application/json",
             # Tell MAS that we support reading the device ID as an explicit
@@ -327,13 +326,12 @@ class MSC3861DelegatedAuth(BaseAuth):
         try:
             with start_active_span("mas-introspect-token"):
                 inject_request_headers(raw_headers)
-                with PreserveLoggingContext():
-                    resp_body = await self._rust_http_client.post(
-                        url=uri,
-                        response_limit=1 * 1024 * 1024,
-                        headers=raw_headers,
-                        request_body=body,
-                    )
+                resp_body = await self._rust_http_client.post(
+                    url=uri,
+                    response_limit=1 * 1024 * 1024,
+                    headers=raw_headers,
+                    request_body=body,
+                )
         except HttpResponseException as e:
             end_time = self._clock.time()
             introspection_response_timer.labels(
@@ -522,7 +520,7 @@ class MSC3861DelegatedAuth(BaseAuth):
             raise InvalidClientTokenError("Token is not active")
 
         # Let's look at the scope
-        scope: List[str] = introspection_result.get_scope_list()
+        scope: list[str] = introspection_result.get_scope_list()
 
         # Determine type of user based on presence of particular scopes
         has_user_scope = (
@@ -577,7 +575,7 @@ class MSC3861DelegatedAuth(BaseAuth):
             # We only allow a single device_id in the scope, so we find them all in the
             # scope list, and raise if there are more than one. The OIDC server should be
             # the one enforcing valid scopes, so we raise a 500 if we find an invalid scope.
-            device_ids: Set[str] = set()
+            device_ids: set[str] = set()
             for tok in scope:
                 if tok.startswith(UNSTABLE_SCOPE_MATRIX_DEVICE_PREFIX):
                     device_ids.add(tok[len(UNSTABLE_SCOPE_MATRIX_DEVICE_PREFIX) :])
diff --git a/synapse/api/auth_blocking.py b/synapse/api/auth_blocking.py
index 303c9ba03e..3ed47b20c4 100644
--- a/synapse/api/auth_blocking.py
+++ b/synapse/api/auth_blocking.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING
 
 from synapse.api.constants import LimitBlockingTypes, UserTypes
 from synapse.api.errors import Codes, ResourceLimitError
@@ -51,10 +51,10 @@ class AuthBlocking:
 
     async def check_auth_blocking(
         self,
-        user_id: Optional[str] = None,
-        threepid: Optional[dict] = None,
-        user_type: Optional[str] = None,
-        requester: Optional[Requester] = None,
+        user_id: str | None = None,
+        threepid: dict | None = None,
+        user_type: str | None = None,
+        requester: Requester | None = None,
     ) -> None:
         """Checks if the user should be rejected for some external reason,
         such as monthly active user limiting or global disable flag
diff --git a/synapse/api/constants.py b/synapse/api/constants.py
index 7a8f546d6b..86620bda33 100644
--- a/synapse/api/constants.py
+++ b/synapse/api/constants.py
@@ -272,6 +272,9 @@ class EventContentFields:
     M_TOPIC: Final = "m.topic"
     M_TEXT: Final = "m.text"
 
+    # Event relations
+    RELATIONS: Final = "m.relates_to"
+
 
 class EventUnsignedContentFields:
     """Fields found inside the 'unsigned' data on events"""
@@ -360,3 +363,10 @@ class Direction(enum.Enum):
 class ProfileFields:
     DISPLAYNAME: Final = "displayname"
     AVATAR_URL: Final = "avatar_url"
+
+
+class MRelatesToFields:
+    """Fields found inside m.relates_to content blocks."""
+
+    EVENT_ID: Final = "event_id"
+    REL_TYPE: Final = "rel_type"
diff --git a/synapse/api/errors.py b/synapse/api/errors.py
index fb6721c0ee..c4339ebef8 100644
--- a/synapse/api/errors.py
+++ b/synapse/api/errors.py
@@ -26,7 +26,7 @@ import math
 import typing
 from enum import Enum
 from http import HTTPStatus
-from typing import Any, Dict, List, Optional, Union
+from typing import Any, Optional
 
 from twisted.web import http
 
@@ -164,9 +164,9 @@ class CodeMessageException(RuntimeError):
 
     def __init__(
         self,
-        code: Union[int, HTTPStatus],
+        code: int | HTTPStatus,
         msg: str,
-        headers: Optional[Dict[str, str]] = None,
+        headers: dict[str, str] | None = None,
     ):
         super().__init__("%d: %s" % (code, msg))
 
@@ -201,7 +201,7 @@ class RedirectException(CodeMessageException):
         super().__init__(code=http_code, msg=msg)
         self.location = location
 
-        self.cookies: List[bytes] = []
+        self.cookies: list[bytes] = []
 
 
 class SynapseError(CodeMessageException):
@@ -223,8 +223,8 @@ class SynapseError(CodeMessageException):
         code: int,
         msg: str,
         errcode: str = Codes.UNKNOWN,
-        additional_fields: Optional[Dict] = None,
-        headers: Optional[Dict[str, str]] = None,
+        additional_fields: dict | None = None,
+        headers: dict[str, str] | None = None,
     ):
         """Constructs a synapse error.
 
@@ -236,7 +236,7 @@ class SynapseError(CodeMessageException):
         super().__init__(code, msg, headers)
         self.errcode = errcode
         if additional_fields is None:
-            self._additional_fields: Dict = {}
+            self._additional_fields: dict = {}
         else:
             self._additional_fields = dict(additional_fields)
 
@@ -244,7 +244,7 @@ class SynapseError(CodeMessageException):
         return cs_error(self.msg, self.errcode, **self._additional_fields)
 
     @property
-    def debug_context(self) -> Optional[str]:
+    def debug_context(self) -> str | None:
         """Override this to add debugging context that shouldn't be sent to clients."""
         return None
 
@@ -276,7 +276,7 @@ class ProxiedRequestError(SynapseError):
         code: int,
         msg: str,
         errcode: str = Codes.UNKNOWN,
-        additional_fields: Optional[Dict] = None,
+        additional_fields: dict | None = None,
     ):
         super().__init__(code, msg, errcode, additional_fields)
 
@@ -340,7 +340,7 @@ class FederationDeniedError(SynapseError):
         destination: The destination which has been denied
     """
 
-    def __init__(self, destination: Optional[str]):
+    def __init__(self, destination: str | None):
         """Raised by federation client or server to indicate that we are
         are deliberately not attempting to contact a given server because it is
         not on our federation whitelist.
@@ -399,7 +399,7 @@ class AuthError(SynapseError):
         code: int,
         msg: str,
         errcode: str = Codes.FORBIDDEN,
-        additional_fields: Optional[dict] = None,
+        additional_fields: dict | None = None,
     ):
         super().__init__(code, msg, errcode, additional_fields)
 
@@ -409,7 +409,7 @@ class OAuthInsufficientScopeError(SynapseError):
 
     def __init__(
         self,
-        required_scopes: List[str],
+        required_scopes: list[str],
     ):
         headers = {
             "WWW-Authenticate": 'Bearer error="insufficient_scope", scope="%s"'
@@ -432,7 +432,7 @@ class UnstableSpecAuthError(AuthError):
         msg: str,
         errcode: str,
         previous_errcode: str = Codes.FORBIDDEN,
-        additional_fields: Optional[dict] = None,
+        additional_fields: dict | None = None,
     ):
         self.previous_errcode = previous_errcode
         super().__init__(code, msg, errcode, additional_fields)
@@ -497,8 +497,8 @@ class ResourceLimitError(SynapseError):
         code: int,
         msg: str,
         errcode: str = Codes.RESOURCE_LIMIT_EXCEEDED,
-        admin_contact: Optional[str] = None,
-        limit_type: Optional[str] = None,
+        admin_contact: str | None = None,
+        limit_type: str | None = None,
     ):
         self.admin_contact = admin_contact
         self.limit_type = limit_type
@@ -542,7 +542,7 @@ class InvalidCaptchaError(SynapseError):
         self,
         code: int = 400,
         msg: str = "Invalid captcha.",
-        error_url: Optional[str] = None,
+        error_url: str | None = None,
         errcode: str = Codes.CAPTCHA_INVALID,
     ):
         super().__init__(code, msg, errcode)
@@ -563,9 +563,9 @@ class LimitExceededError(SynapseError):
         self,
         limiter_name: str,
         code: int = 429,
-        retry_after_ms: Optional[int] = None,
+        retry_after_ms: int | None = None,
         errcode: str = Codes.LIMIT_EXCEEDED,
-        pause: Optional[float] = None,
+        pause: float | None = None,
     ):
         # Use HTTP header Retry-After to enable library-assisted retry handling.
         headers = (
@@ -582,7 +582,7 @@ class LimitExceededError(SynapseError):
         return cs_error(self.msg, self.errcode, retry_after_ms=self.retry_after_ms)
 
     @property
-    def debug_context(self) -> Optional[str]:
+    def debug_context(self) -> str | None:
         return self.limiter_name
 
 
@@ -675,7 +675,7 @@ class RequestSendFailed(RuntimeError):
 
 
 class UnredactedContentDeletedError(SynapseError):
-    def __init__(self, content_keep_ms: Optional[int] = None):
+    def __init__(self, content_keep_ms: int | None = None):
         super().__init__(
             404,
             "The content for that event has already been erased from the database",
@@ -751,7 +751,7 @@ class FederationError(RuntimeError):
         code: int,
         reason: str,
         affected: str,
-        source: Optional[str] = None,
+        source: str | None = None,
     ):
         if level not in ["FATAL", "ERROR", "WARN"]:
             raise ValueError("Level is not valid: %s" % (level,))
@@ -786,7 +786,7 @@ class FederationPullAttemptBackoffError(RuntimeError):
     """
 
     def __init__(
-        self, event_ids: "StrCollection", message: Optional[str], retry_after_ms: int
+        self, event_ids: "StrCollection", message: str | None, retry_after_ms: int
     ):
         event_ids = list(event_ids)
 
diff --git a/synapse/api/filtering.py b/synapse/api/filtering.py
index 34dd12368a..9b47c20437 100644
--- a/synapse/api/filtering.py
+++ b/synapse/api/filtering.py
@@ -26,14 +26,9 @@ from typing import (
     Awaitable,
     Callable,
     Collection,
-    Dict,
     Iterable,
-    List,
     Mapping,
-    Optional,
-    Set,
     TypeVar,
-    Union,
 )
 
 import jsonschema
@@ -158,7 +153,7 @@ class Filtering:
         self.DEFAULT_FILTER_COLLECTION = FilterCollection(hs, {})
 
     async def get_user_filter(
-        self, user_id: UserID, filter_id: Union[int, str]
+        self, user_id: UserID, filter_id: int | str
     ) -> "FilterCollection":
         result = await self.store.get_user_filter(user_id, filter_id)
         return FilterCollection(self._hs, result)
@@ -248,34 +243,34 @@ class FilterCollection:
 
     async def filter_presence(
         self, presence_states: Iterable[UserPresenceState]
-    ) -> List[UserPresenceState]:
+    ) -> list[UserPresenceState]:
         return await self._presence_filter.filter(presence_states)
 
     async def filter_global_account_data(
         self, events: Iterable[JsonDict]
-    ) -> List[JsonDict]:
+    ) -> list[JsonDict]:
         return await self._global_account_data_filter.filter(events)
 
-    async def filter_room_state(self, events: Iterable[EventBase]) -> List[EventBase]:
+    async def filter_room_state(self, events: Iterable[EventBase]) -> list[EventBase]:
         return await self._room_state_filter.filter(
             await self._room_filter.filter(events)
         )
 
     async def filter_room_timeline(
         self, events: Iterable[EventBase]
-    ) -> List[EventBase]:
+    ) -> list[EventBase]:
         return await self._room_timeline_filter.filter(
             await self._room_filter.filter(events)
         )
 
-    async def filter_room_ephemeral(self, events: Iterable[JsonDict]) -> List[JsonDict]:
+    async def filter_room_ephemeral(self, events: Iterable[JsonDict]) -> list[JsonDict]:
         return await self._room_ephemeral_filter.filter(
             await self._room_filter.filter(events)
         )
 
     async def filter_room_account_data(
         self, events: Iterable[JsonDict]
-    ) -> List[JsonDict]:
+    ) -> list[JsonDict]:
         return await self._room_account_data_filter.filter(
             await self._room_filter.filter(events)
         )
@@ -440,7 +435,7 @@ class Filter:
 
             return True
 
-    def _check_fields(self, field_matchers: Dict[str, Callable[[str], bool]]) -> bool:
+    def _check_fields(self, field_matchers: dict[str, Callable[[str], bool]]) -> bool:
         """Checks whether the filter matches the given event fields.
 
         Args:
@@ -474,7 +469,7 @@ class Filter:
         # Otherwise, accept it.
         return True
 
-    def filter_rooms(self, room_ids: Iterable[str]) -> Set[str]:
+    def filter_rooms(self, room_ids: Iterable[str]) -> set[str]:
         """Apply the 'rooms' filter to a given list of rooms.
 
         Args:
@@ -496,7 +491,7 @@ class Filter:
 
     async def _check_event_relations(
         self, events: Collection[FilterEvent]
-    ) -> List[FilterEvent]:
+    ) -> list[FilterEvent]:
         # The event IDs to check, mypy doesn't understand the isinstance check.
         event_ids = [event.event_id for event in events if isinstance(event, EventBase)]  # type: ignore[attr-defined]
         event_ids_to_keep = set(
@@ -511,7 +506,7 @@ class Filter:
             if not isinstance(event, EventBase) or event.event_id in event_ids_to_keep
         ]
 
-    async def filter(self, events: Iterable[FilterEvent]) -> List[FilterEvent]:
+    async def filter(self, events: Iterable[FilterEvent]) -> list[FilterEvent]:
         result = [event for event in events if self._check(event)]
 
         if self.related_by_senders or self.related_by_rel_types:
@@ -534,7 +529,7 @@ class Filter:
         return newFilter
 
 
-def _matches_wildcard(actual_value: Optional[str], filter_value: str) -> bool:
+def _matches_wildcard(actual_value: str | None, filter_value: str) -> bool:
     if filter_value.endswith("*") and isinstance(actual_value, str):
         type_prefix = filter_value[:-1]
         return actual_value.startswith(type_prefix)
diff --git a/synapse/api/presence.py b/synapse/api/presence.py
index 28c10403ce..0e2fe625c9 100644
--- a/synapse/api/presence.py
+++ b/synapse/api/presence.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import Any, Optional
+from typing import Any
 
 import attr
 
@@ -41,15 +41,13 @@ class UserDevicePresenceState:
     """
 
     user_id: str
-    device_id: Optional[str]
+    device_id: str | None
     state: str
     last_active_ts: int
     last_sync_ts: int
 
     @classmethod
-    def default(
-        cls, user_id: str, device_id: Optional[str]
-    ) -> "UserDevicePresenceState":
+    def default(cls, user_id: str, device_id: str | None) -> "UserDevicePresenceState":
         """Returns a default presence state."""
         return cls(
             user_id=user_id,
@@ -81,7 +79,7 @@ class UserPresenceState:
     last_active_ts: int
     last_federation_update_ts: int
     last_user_sync_ts: int
-    status_msg: Optional[str]
+    status_msg: str | None
     currently_active: bool
 
     def as_dict(self) -> JsonDict:
diff --git a/synapse/api/ratelimiting.py b/synapse/api/ratelimiting.py
index 9d1c7801bc..df884d47d7 100644
--- a/synapse/api/ratelimiting.py
+++ b/synapse/api/ratelimiting.py
@@ -20,13 +20,14 @@
 #
 #
 
-from typing import TYPE_CHECKING, Dict, Hashable, Optional, Tuple
+from typing import TYPE_CHECKING, Hashable, Optional
 
 from synapse.api.errors import LimitExceededError
 from synapse.config.ratelimiting import RatelimitSettings
 from synapse.storage.databases.main import DataStore
 from synapse.types import Requester
 from synapse.util.clock import Clock
+from synapse.util.wheel_timer import WheelTimer
 
 if TYPE_CHECKING:
     # To avoid circular imports:
@@ -92,13 +93,16 @@ class Ratelimiter:
         #   * The number of tokens currently in the bucket,
         #   * The time point when the bucket was last completely empty, and
         #   * The rate_hz (leak rate) of this particular bucket.
-        self.actions: Dict[Hashable, Tuple[float, float, float]] = {}
+        self.actions: dict[Hashable, tuple[int, float, float]] = {}
 
-        self.clock.looping_call(self._prune_message_counts, 60 * 1000)
+        # Records when actions should potentially be pruned. Note that we don't
+        # need to be accurate here, as this is just a cleanup job of `actions`
+        # and doesn't affect correctness.
+        self._timer: WheelTimer[Hashable] = WheelTimer()
 
-    def _get_key(
-        self, requester: Optional[Requester], key: Optional[Hashable]
-    ) -> Hashable:
+        self.clock.looping_call(self._prune_message_counts, 15 * 1000)
+
+    def _get_key(self, requester: Requester | None, key: Hashable | None) -> Hashable:
         """Use the requester's MXID as a fallback key if no key is provided."""
         if key is None:
             if not requester:
@@ -109,20 +113,20 @@ class Ratelimiter:
 
     def _get_action_counts(
         self, key: Hashable, time_now_s: float
-    ) -> Tuple[float, float, float]:
+    ) -> tuple[int, float, float]:
         """Retrieve the action counts, with a fallback representing an empty bucket."""
-        return self.actions.get(key, (0.0, time_now_s, 0.0))
+        return self.actions.get(key, (0, time_now_s, self.rate_hz))
 
     async def can_do_action(
         self,
-        requester: Optional[Requester],
-        key: Optional[Hashable] = None,
-        rate_hz: Optional[float] = None,
-        burst_count: Optional[int] = None,
+        requester: Requester | None,
+        key: Hashable | None = None,
+        rate_hz: float | None = None,
+        burst_count: int | None = None,
         update: bool = True,
         n_actions: int = 1,
-        _time_now_s: Optional[float] = None,
-    ) -> Tuple[bool, float]:
+        _time_now_s: float | None = None,
+    ) -> tuple[bool, float]:
         """Can the entity (e.g. user or IP address) perform the action?
 
         Checks if the user has ratelimiting disabled in the database by looking
@@ -217,8 +221,11 @@ class Ratelimiter:
             allowed = True
             action_count = action_count + n_actions
 
-        if update:
-            self.actions[key] = (action_count, time_start, rate_hz)
+        # Only record the action if we're allowed to perform it.
+        if allowed and update:
+            self._record_action_inner(
+                key, action_count, time_start, rate_hz, time_now_s
+            )
 
         if rate_hz > 0:
             # Find out when the count of existing actions expires
@@ -238,10 +245,10 @@ class Ratelimiter:
 
     def record_action(
         self,
-        requester: Optional[Requester],
-        key: Optional[Hashable] = None,
+        requester: Requester | None,
+        key: Hashable | None = None,
         n_actions: int = 1,
-        _time_now_s: Optional[float] = None,
+        _time_now_s: float | None = None,
     ) -> None:
         """Record that an action(s) took place, even if they violate the rate limit.
 
@@ -264,7 +271,37 @@ class Ratelimiter:
         key = self._get_key(requester, key)
         time_now_s = _time_now_s if _time_now_s is not None else self.clock.time()
         action_count, time_start, rate_hz = self._get_action_counts(key, time_now_s)
-        self.actions[key] = (action_count + n_actions, time_start, rate_hz)
+        self._record_action_inner(
+            key, action_count + n_actions, time_start, rate_hz, time_now_s
+        )
+
+    def _record_action_inner(
+        self,
+        key: Hashable,
+        action_count: int,
+        time_start: float,
+        rate_hz: float,
+        time_now_s: float,
+    ) -> None:
+        """Helper to atomically update the action count for a given key."""
+        prune_time_s = time_start + action_count / rate_hz
+
+        # If the prune time is in the past, we can just remove the entry rather
+        # than inserting and immediately pruning.
+        if prune_time_s <= time_now_s:
+            self.actions.pop(key, None)
+            return
+
+        self.actions[key] = (action_count, time_start, rate_hz)
+
+        # We need to make sure that we only call prune *after* the entry
+        # expires, otherwise the scheduled prune may not actually prune it. This
+        # is just a cleanup job, so it doesn't matter if entries aren't pruned
+        # immediately after they expire. Hence we schedule the prune a little
+        # after the entry is due to expire.
+        prune_time_s += 0.1
+
+        self._timer.insert(int(time_now_s * 1000), key, int(prune_time_s * 1000))
 
     def _prune_message_counts(self) -> None:
         """Remove message count entries that have not exceeded their defined
@@ -272,29 +309,35 @@ class Ratelimiter:
         """
         time_now_s = self.clock.time()
 
-        # We create a copy of the key list here as the dictionary is modified during
-        # the loop
-        for key in list(self.actions.keys()):
-            action_count, time_start, rate_hz = self.actions[key]
+        # Pull out all the keys that *might* need pruning. We still need to
+        # verify they haven't since been updated.
+        to_prune = self._timer.fetch(int(time_now_s * 1000))
+
+        for key in to_prune:
+            value = self.actions.get(key)
+            if value is None:
+                continue
+
+            action_count, time_start, rate_hz = value
 
             # Rate limit = "seconds since we started limiting this action" * rate_hz
             # If this limit has not been exceeded, wipe our record of this action
             time_delta = time_now_s - time_start
             if action_count - time_delta * rate_hz > 0:
                 continue
-            else:
-                del self.actions[key]
+
+            del self.actions[key]
 
     async def ratelimit(
         self,
-        requester: Optional[Requester],
-        key: Optional[Hashable] = None,
-        rate_hz: Optional[float] = None,
-        burst_count: Optional[int] = None,
+        requester: Requester | None,
+        key: Hashable | None = None,
+        rate_hz: float | None = None,
+        burst_count: int | None = None,
         update: bool = True,
         n_actions: int = 1,
-        _time_now_s: Optional[float] = None,
-        pause: Optional[float] = 0.5,
+        _time_now_s: float | None = None,
+        pause: float | None = 0.5,
     ) -> None:
         """Checks if an action can be performed. If not, raises a LimitExceededError
 
@@ -351,7 +394,7 @@ class RequestRatelimiter:
         store: DataStore,
         clock: Clock,
         rc_message: RatelimitSettings,
-        rc_admin_redaction: Optional[RatelimitSettings],
+        rc_admin_redaction: RatelimitSettings | None,
     ):
         self.store = store
         self.clock = clock
@@ -367,7 +410,7 @@ class RequestRatelimiter:
         # Check whether ratelimiting room admin message redaction is enabled
         # by the presence of rate limits in the config
         if rc_admin_redaction:
-            self.admin_redaction_ratelimiter: Optional[Ratelimiter] = Ratelimiter(
+            self.admin_redaction_ratelimiter: Ratelimiter | None = Ratelimiter(
                 store=self.store,
                 clock=self.clock,
                 cfg=rc_admin_redaction,
diff --git a/synapse/api/room_versions.py b/synapse/api/room_versions.py
index 71ef5952c3..97dac661a3 100644
--- a/synapse/api/room_versions.py
+++ b/synapse/api/room_versions.py
@@ -18,7 +18,7 @@
 #
 #
 
-from typing import Callable, Dict, Optional, Tuple
+from typing import Callable
 
 import attr
 
@@ -109,7 +109,7 @@ class RoomVersion:
     # is not enough to mark it "supported": the push rule evaluator also needs to
     # support the flag. Unknown flags are ignored by the evaluator, making conditions
     # fail if used.
-    msc3931_push_features: Tuple[str, ...]  # values from PushRuleRoomFlag
+    msc3931_push_features: tuple[str, ...]  # values from PushRuleRoomFlag
     # MSC3757: Restricting who can overwrite a state event
     msc3757_enabled: bool
     # MSC4289: Creator power enabled
@@ -476,7 +476,7 @@ class RoomVersions:
     )
 
 
-KNOWN_ROOM_VERSIONS: Dict[str, RoomVersion] = {
+KNOWN_ROOM_VERSIONS: dict[str, RoomVersion] = {
     v.identifier: v
     for v in (
         RoomVersions.V1,
@@ -503,7 +503,7 @@ class RoomVersionCapability:
     """An object which describes the unique attributes of a room version."""
 
     identifier: str  # the identifier for this capability
-    preferred_version: Optional[RoomVersion]
+    preferred_version: RoomVersion | None
     support_check_lambda: Callable[[RoomVersion], bool]
 
 
diff --git a/synapse/api/urls.py b/synapse/api/urls.py
index baa6e2d390..b6147353d4 100644
--- a/synapse/api/urls.py
+++ b/synapse/api/urls.py
@@ -24,7 +24,6 @@
 import hmac
 import urllib.parse
 from hashlib import sha256
-from typing import Optional
 from urllib.parse import urlencode, urljoin
 
 from synapse.config import ConfigError
@@ -75,7 +74,7 @@ class LoginSSORedirectURIBuilder:
         self._public_baseurl = hs_config.server.public_baseurl
 
     def build_login_sso_redirect_uri(
-        self, *, idp_id: Optional[str], client_redirect_url: str
+        self, *, idp_id: str | None, client_redirect_url: str
     ) -> str:
         """Build a `/login/sso/redirect` URI for the given identity provider.
 
diff --git a/synapse/app/_base.py b/synapse/app/_base.py
index 5638724896..52bdb9e0d7 100644
--- a/synapse/app/_base.py
+++ b/synapse/app/_base.py
@@ -28,18 +28,17 @@ import sys
 import traceback
 import warnings
 from textwrap import indent
+from threading import Thread
+from types import FrameType
 from typing import (
     TYPE_CHECKING,
     Any,
     Awaitable,
     Callable,
-    Dict,
-    List,
     NoReturn,
-    Optional,
-    Tuple,
     cast,
 )
+from wsgiref.simple_server import WSGIServer
 
 from cryptography.utils import CryptographyDeprecationWarning
 from typing_extensions import ParamSpec
@@ -62,7 +61,6 @@ from twisted.web.resource import Resource
 import synapse.util.caches
 from synapse.api.constants import MAX_PDU_SIZE
 from synapse.app import check_bind_error
-from synapse.app.phone_stats_home import start_phone_stats_home
 from synapse.config import ConfigError
 from synapse.config._base import format_config_error
 from synapse.config.homeserver import HomeServerConfig
@@ -74,7 +72,6 @@ from synapse.handlers.auth import load_legacy_password_auth_providers
 from synapse.http.site import SynapseSite
 from synapse.logging.context import LoggingContext, PreserveLoggingContext
 from synapse.metrics import install_gc_manager, register_threadpool
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.metrics.jemalloc import setup_jemalloc_stats
 from synapse.module_api.callbacks.spamchecker_callbacks import load_legacy_spam_checkers
 from synapse.module_api.callbacks.third_party_event_rules_callbacks import (
@@ -97,22 +94,53 @@ reactor = cast(ISynapseReactor, _reactor)
 
 logger = logging.getLogger(__name__)
 
-# list of tuples of function, args list, kwargs dict
-_sighup_callbacks: List[
-    Tuple[Callable[..., None], Tuple[object, ...], Dict[str, object]]
-] = []
+_instance_id_to_sighup_callbacks_map: dict[
+    str, list[tuple[Callable[..., None], tuple[object, ...], dict[str, object]]]
+] = {}
+"""
+Map from homeserver instance_id to a list of callbacks.
+
+We use `instance_id` instead of `server_name` because it's possible to have multiple
+workers running in the same process with the same `server_name`.
+"""
 P = ParamSpec("P")
 
 
-def register_sighup(func: Callable[P, None], *args: P.args, **kwargs: P.kwargs) -> None:
+def register_sighup(
+    hs: "HomeServer",
+    func: Callable[P, None],
+    *args: P.args,
+    **kwargs: P.kwargs,
+) -> None:
     """
     Register a function to be called when a SIGHUP occurs.
 
     Args:
+        homeserver_instance_id: The unique ID for this Synapse process instance
+            (`hs.get_instance_id()`) that this hook is associated with.
         func: Function to be called when sent a SIGHUP signal.
         *args, **kwargs: args and kwargs to be passed to the target function.
     """
-    _sighup_callbacks.append((func, args, kwargs))
+
+    # Wrap the function so we can run it within a logcontext
+    def _callback_wrapper(*args: P.args, **kwargs: P.kwargs) -> None:
+        with LoggingContext(name="sighup", server_name=hs.hostname):
+            func(*args, **kwargs)
+
+    _instance_id_to_sighup_callbacks_map.setdefault(hs.get_instance_id(), []).append(
+        (_callback_wrapper, args, kwargs)
+    )
+
+
+def unregister_sighups(homeserver_instance_id: str) -> None:
+    """
+    Unregister all sighup functions associated with this Synapse instance.
+
+    Args:
+        homeserver_instance_id: The unique ID for this Synapse process instance to
+            unregister hooks for (`hs.get_instance_id()`).
+    """
+    _instance_id_to_sighup_callbacks_map.pop(homeserver_instance_id, [])
 
 
 def start_worker_reactor(
@@ -150,8 +178,8 @@ def start_worker_reactor(
 def start_reactor(
     appname: str,
     soft_file_limit: int,
-    gc_thresholds: Optional[Tuple[int, int, int]],
-    pid_file: Optional[str],
+    gc_thresholds: tuple[int, int, int] | None,
+    pid_file: str | None,
     daemonize: bool,
     print_pidfile: bool,
     logger: logging.Logger,
@@ -281,7 +309,9 @@ def register_start(
     clock.call_when_running(lambda: defer.ensureDeferred(wrapper()))
 
 
-def listen_metrics(bind_addresses: StrCollection, port: int) -> None:
+def listen_metrics(
+    bind_addresses: StrCollection, port: int
+) -> list[tuple[WSGIServer, Thread]]:
     """
     Start Prometheus metrics server.
 
@@ -294,14 +324,22 @@ def listen_metrics(bind_addresses: StrCollection, port: int) -> None:
     bytecode at a time), this still works because the metrics thread can preempt the
     Twisted reactor thread between bytecode boundaries and the metrics thread gets
     scheduled with roughly equal priority to the Twisted reactor thread.
+
+    Returns:
+        List of WSGIServer with the thread they are running on.
     """
     from prometheus_client import start_http_server as start_http_server_prometheus
 
     from synapse.metrics import RegistryProxy
 
+    servers: list[tuple[WSGIServer, Thread]] = []
     for host in bind_addresses:
         logger.info("Starting metrics listener on %s:%d", host, port)
-        start_http_server_prometheus(port, addr=host, registry=RegistryProxy)
+        server, thread = start_http_server_prometheus(
+            port, addr=host, registry=RegistryProxy
+        )
+        servers.append((server, thread))
+    return servers
 
 
 def listen_manhole(
@@ -309,7 +347,7 @@ def listen_manhole(
     port: int,
     manhole_settings: ManholeConfig,
     manhole_globals: dict,
-) -> None:
+) -> list[Port]:
     # twisted.conch.manhole 21.1.0 uses "int_from_bytes", which produces a confusing
     # warning. It's fixed by https://github.com/twisted/twisted/pull/1522), so
     # suppress the warning for now.
@@ -321,7 +359,7 @@ def listen_manhole(
 
     from synapse.util.manhole import manhole
 
-    listen_tcp(
+    return listen_tcp(
         bind_addresses,
         port,
         manhole(settings=manhole_settings, globals=manhole_globals),
@@ -334,7 +372,7 @@ def listen_tcp(
     factory: ServerFactory,
     reactor: IReactorTCP = reactor,
     backlog: int = 50,
-) -> List[Port]:
+) -> list[Port]:
     """
     Create a TCP socket for a port and several addresses
 
@@ -359,7 +397,7 @@ def listen_unix(
     factory: ServerFactory,
     reactor: IReactorUNIX = reactor,
     backlog: int = 50,
-) -> List[Port]:
+) -> list[Port]:
     """
     Create a UNIX socket for a given path and 'mode' permission
 
@@ -381,20 +419,29 @@ def listen_http(
     root_resource: Resource,
     version_string: str,
     max_request_body_size: int,
-    context_factory: Optional[IOpenSSLContextFactory],
+    context_factory: IOpenSSLContextFactory | None,
     reactor: ISynapseReactor = reactor,
-) -> List[Port]:
+) -> list[Port]:
+    """
+    Args:
+        listener_config: TODO
+        root_resource: TODO
+        version_string: A string to present for the Server header
+        max_request_body_size: TODO
+        context_factory: TODO
+        reactor: TODO
+    """
     assert listener_config.http_options is not None
 
     site_tag = listener_config.get_site_tag()
 
     site = SynapseSite(
-        "synapse.access.%s.%s"
+        logger_name="synapse.access.%s.%s"
         % ("https" if listener_config.is_tls() else "http", site_tag),
-        site_tag,
-        listener_config,
-        root_resource,
-        version_string,
+        site_tag=site_tag,
+        config=listener_config,
+        resource=root_resource,
+        server_version_string=version_string,
         max_request_body_size=max_request_body_size,
         reactor=reactor,
         hs=hs,
@@ -444,7 +491,7 @@ def listen_ssl(
     context_factory: IOpenSSLContextFactory,
     reactor: IReactorSSL = reactor,
     backlog: int = 50,
-) -> List[Port]:
+) -> list[Port]:
     """
     Create an TLS-over-TCP socket for a port and several addresses
 
@@ -498,7 +545,60 @@ def refresh_certificate(hs: "HomeServer") -> None:
         logger.info("Context factories updated.")
 
 
-async def start(hs: "HomeServer") -> None:
+_already_setup_sighup_handling = False
+"""
+Marks whether we've already successfully ran `setup_sighup_handling()`.
+"""
+
+
+def setup_sighup_handling() -> None:
+    """
+    Set up SIGHUP handling to call registered callbacks.
+
+    This can be called multiple times safely.
+    """
+    global _already_setup_sighup_handling
+    # We only need to set things up once per process.
+    if _already_setup_sighup_handling:
+        return
+
+    previous_sighup_handler: Callable[[int, FrameType | None], Any] | int | None = None
+
+    # Set up the SIGHUP machinery.
+    if hasattr(signal, "SIGHUP"):
+
+        def handle_sighup(*args: Any, **kwargs: Any) -> None:
+            # Tell systemd our state, if we're using it. This will silently fail if
+            # we're not using systemd.
+            sdnotify(b"RELOADING=1")
+
+            if callable(previous_sighup_handler):
+                previous_sighup_handler(*args, **kwargs)
+
+            for sighup_callbacks in _instance_id_to_sighup_callbacks_map.values():
+                for func, args, kwargs in sighup_callbacks:
+                    func(*args, **kwargs)
+
+            sdnotify(b"READY=1")
+
+        # We defer running the sighup handlers until next reactor tick. This
+        # is so that we're in a sane state, e.g. flushing the logs may fail
+        # if the sighup happens in the middle of writing a log entry.
+        def run_sighup(*args: Any, **kwargs: Any) -> None:
+            # `callFromThread` should be "signal safe" as well as thread
+            # safe.
+            reactor.callFromThread(handle_sighup, *args, **kwargs)
+
+        # Register for the SIGHUP signal, chaining any existing handler as there can
+        # only be one handler per signal and we don't want to clobber any existing
+        # handlers (like the `multi_synapse` shard process in the context of Synapse Pro
+        # for small hosts)
+        previous_sighup_handler = signal.signal(signal.SIGHUP, run_sighup)
+
+    _already_setup_sighup_handling = True
+
+
+async def start(hs: "HomeServer", *, freeze: bool = True) -> None:
     """
     Start a Synapse server or worker.
 
@@ -509,6 +609,11 @@ async def start(hs: "HomeServer") -> None:
 
     Args:
         hs: homeserver instance
+        freeze: whether to freeze the homeserver base objects in the garbage collector.
+            May improve garbage collection performance by marking objects with an effectively
+            static lifetime as frozen so they don't need to be considered for cleanup.
+            If you ever want to `shutdown` the homeserver, this needs to be
+            False otherwise the homeserver cannot be garbage collected after `shutdown`.
     """
     server_name = hs.hostname
     reactor = hs.get_reactor()
@@ -532,44 +637,23 @@ async def start(hs: "HomeServer") -> None:
         name="gai_resolver", server_name=server_name, threadpool=resolver_threadpool
     )
 
-    # Set up the SIGHUP machinery.
-    if hasattr(signal, "SIGHUP"):
-
-        def handle_sighup(*args: Any, **kwargs: Any) -> "defer.Deferred[None]":
-            async def _handle_sighup(*args: Any, **kwargs: Any) -> None:
-                # Tell systemd our state, if we're using it. This will silently fail if
-                # we're not using systemd.
-                sdnotify(b"RELOADING=1")
-
-                for i, args, kwargs in _sighup_callbacks:
-                    i(*args, **kwargs)
-
-                sdnotify(b"READY=1")
-
-            return run_as_background_process(
-                "sighup",
-                server_name,
-                _handle_sighup,
-                *args,
-                **kwargs,
-            )
-
-        # We defer running the sighup handlers until next reactor tick. This
-        # is so that we're in a sane state, e.g. flushing the logs may fail
-        # if the sighup happens in the middle of writing a log entry.
-        def run_sighup(*args: Any, **kwargs: Any) -> None:
-            # `callFromThread` should be "signal safe" as well as thread
-            # safe.
-            reactor.callFromThread(handle_sighup, *args, **kwargs)
-
-        signal.signal(signal.SIGHUP, run_sighup)
-
-        register_sighup(refresh_certificate, hs)
-        register_sighup(reload_cache_config, hs.config)
+    setup_sighup_handling()
+    register_sighup(hs, refresh_certificate, hs)
+    register_sighup(hs, reload_cache_config, hs.config)
 
     # Apply the cache config.
     hs.config.caches.resize_all_caches()
 
+    # Load the OIDC provider metadatas, if OIDC is enabled.
+    if hs.config.oidc.oidc_enabled:
+        oidc = hs.get_oidc_handler()
+        # Loading the provider metadata also ensures the provider config is valid.
+        #
+        # FIXME: It feels a bit strange to validate and block on startup as one of these
+        # OIDC providers could be temporarily unavailable and cause Synapse to be unable
+        # to start.
+        await oidc.load_metadata()
+
     # Load the certificate from disk.
     refresh_certificate(hs)
 
@@ -603,7 +687,11 @@ async def start(hs: "HomeServer") -> None:
             logger.info("Shutting down...")
 
     # Log when we start the shut down process.
-    hs.get_clock().add_system_event_trigger("before", "shutdown", log_shutdown)
+    hs.register_sync_shutdown_handler(
+        phase="before",
+        eventType="shutdown",
+        shutdown_func=log_shutdown,
+    )
 
     setup_sentry(hs)
     setup_sdnotify(hs)
@@ -623,27 +711,24 @@ async def start(hs: "HomeServer") -> None:
     if hs.config.worker.run_background_tasks:
         hs.start_background_tasks()
 
-        # TODO: This should be moved to same pattern we use for other background tasks:
-        # Add to `REQUIRED_ON_BACKGROUND_TASK_STARTUP` and rely on
-        # `start_background_tasks` to start it.
-        await hs.get_common_usage_metrics_manager().setup()
+    if freeze:
+        # We now freeze all allocated objects in the hopes that (almost)
+        # everything currently allocated are things that will be used for the
+        # rest of time. Doing so means less work each GC (hopefully).
+        #
+        # Note that freezing the homeserver object means that it won't be able to be
+        # garbage collected in the case of attempting an in-memory `shutdown`. This only
+        # needs to be considered if such a case is desirable. Exiting the entire Python
+        # process will function expectedly either way.
+        #
+        # PyPy does not (yet?) implement gc.freeze()
+        if hasattr(gc, "freeze"):
+            gc.collect()
+            gc.freeze()
 
-        # TODO: This feels like another pattern that should refactored as one of the
-        # `REQUIRED_ON_BACKGROUND_TASK_STARTUP`
-        start_phone_stats_home(hs)
-
-    # We now freeze all allocated objects in the hopes that (almost)
-    # everything currently allocated are things that will be used for the
-    # rest of time. Doing so means less work each GC (hopefully).
-    #
-    # PyPy does not (yet?) implement gc.freeze()
-    if hasattr(gc, "freeze"):
-        gc.collect()
-        gc.freeze()
-
-        # Speed up shutdowns by freezing all allocated objects. This moves everything
-        # into the permanent generation and excludes them from the final GC.
-        atexit.register(gc.freeze)
+            # Speed up process exit by freezing all allocated objects. This moves everything
+            # into the permanent generation and excludes them from the final GC.
+            atexit.register(gc.freeze)
 
 
 def reload_cache_config(config: HomeServerConfig) -> None:
diff --git a/synapse/app/admin_cmd.py b/synapse/app/admin_cmd.py
index bc84dbdf49..facc98164e 100644
--- a/synapse/app/admin_cmd.py
+++ b/synapse/app/admin_cmd.py
@@ -24,7 +24,7 @@ import logging
 import os
 import sys
 import tempfile
-from typing import List, Mapping, Optional, Sequence, Tuple
+from typing import Mapping, Sequence
 
 from twisted.internet import defer, task
 
@@ -64,8 +64,7 @@ from synapse.storage.databases.main.state import StateGroupWorkerStore
 from synapse.storage.databases.main.stream import StreamWorkerStore
 from synapse.storage.databases.main.tags import TagsWorkerStore
 from synapse.storage.databases.main.user_erasure_store import UserErasureWorkerStore
-from synapse.types import JsonMapping, StateMap
-from synapse.util import SYNAPSE_VERSION
+from synapse.types import ISynapseReactor, JsonMapping, StateMap
 from synapse.util.logcontext import LoggingContext
 
 logger = logging.getLogger("synapse.app.admin_cmd")
@@ -137,7 +136,7 @@ class FileExfiltrationWriter(ExfiltrationWriter):
             to a temporary directory.
     """
 
-    def __init__(self, user_id: str, directory: Optional[str] = None):
+    def __init__(self, user_id: str, directory: str | None = None):
         self.user_id = user_id
 
         if directory:
@@ -151,7 +150,7 @@ class FileExfiltrationWriter(ExfiltrationWriter):
         if list(os.listdir(self.base_directory)):
             raise Exception("Directory must be empty")
 
-    def write_events(self, room_id: str, events: List[EventBase]) -> None:
+    def write_events(self, room_id: str, events: list[EventBase]) -> None:
         room_directory = os.path.join(self.base_directory, "rooms", room_id)
         os.makedirs(room_directory, exist_ok=True)
         events_file = os.path.join(room_directory, "events")
@@ -256,7 +255,7 @@ class FileExfiltrationWriter(ExfiltrationWriter):
         return self.base_directory
 
 
-def load_config(argv_options: List[str]) -> Tuple[HomeServerConfig, argparse.Namespace]:
+def load_config(argv_options: list[str]) -> tuple[HomeServerConfig, argparse.Namespace]:
     parser = argparse.ArgumentParser(description="Synapse Admin Command")
     HomeServerConfig.add_arguments_to_parser(parser)
 
@@ -290,7 +289,21 @@ def load_config(argv_options: List[str]) -> Tuple[HomeServerConfig, argparse.Nam
     return config, args
 
 
-def start(config: HomeServerConfig, args: argparse.Namespace) -> None:
+def create_homeserver(
+    config: HomeServerConfig,
+    reactor: ISynapseReactor | None = None,
+) -> AdminCmdServer:
+    """
+    Create a homeserver instance for the Synapse admin command process.
+
+    Args:
+        config: The configuration for the homeserver.
+        reactor: Optionally provide a reactor to use. Can be useful in different
+            scenarios that you want control over the reactor, such as tests.
+
+    Returns:
+        A homeserver instance.
+    """
     if config.worker.worker_app is not None:
         assert config.worker.worker_app == "synapse.app.admin_cmd"
 
@@ -313,34 +326,63 @@ def start(config: HomeServerConfig, args: argparse.Namespace) -> None:
 
     synapse.events.USE_FROZEN_DICTS = config.server.use_frozen_dicts
 
-    ss = AdminCmdServer(
+    admin_command_server = AdminCmdServer(
         config.server.server_name,
         config=config,
-        version_string=f"Synapse/{SYNAPSE_VERSION}",
+        reactor=reactor,
     )
 
-    setup_logging(ss, config, use_worker_options=True)
+    return admin_command_server
 
-    ss.setup()
 
-    # We use task.react as the basic run command as it correctly handles tearing
-    # down the reactor when the deferreds resolve and setting the return value.
-    # We also make sure that `_base.start` gets run before we actually run the
-    # command.
+def setup(admin_command_server: AdminCmdServer) -> None:
+    """
+    Setup a `AdminCmdServer` instance.
 
-    async def run() -> None:
-        with LoggingContext(name="command", server_name=config.server.server_name):
-            await _base.start(ss)
-            await args.func(ss, args)
-
-    _base.start_worker_reactor(
-        "synapse-admin-cmd",
-        config,
-        run_command=lambda: task.react(lambda _reactor: defer.ensureDeferred(run())),
+    Args:
+        admin_command_server: The homeserver to setup.
+    """
+    setup_logging(
+        admin_command_server, admin_command_server.config, use_worker_options=True
     )
 
+    admin_command_server.setup()
+
+
+async def start(admin_command_server: AdminCmdServer, args: argparse.Namespace) -> None:
+    """
+    Should be called once the reactor is running.
+
+    Args:
+        admin_command_server: The homeserver to setup.
+        args: Command line arguments.
+    """
+    # This needs a logcontext unlike other entrypoints because we're not using
+    # `register_start(...)` to run this function.
+    with LoggingContext(name="start", server_name=admin_command_server.hostname):
+        # We make sure that `_base.start` gets run before we actually run the command.
+        await _base.start(admin_command_server)
+        # Run the command
+        await args.func(admin_command_server, args)
+
+
+def main() -> None:
+    homeserver_config, args = load_config(sys.argv[1:])
+    with LoggingContext(name="main", server_name=homeserver_config.server.server_name):
+        # Initialize and setup the homeserver
+        admin_command_server = create_homeserver(homeserver_config)
+        setup(admin_command_server)
+
+        _base.start_worker_reactor(
+            "synapse-admin-cmd",
+            admin_command_server.config,
+            # We use task.react as the basic run command as it correctly handles tearing
+            # down the reactor when the deferreds resolve and setting the return value.
+            run_command=lambda: task.react(
+                lambda _reactor: defer.ensureDeferred(start(admin_command_server, args))
+            ),
+        )
+
 
 if __name__ == "__main__":
-    homeserver_config, args = load_config(sys.argv[1:])
-    with LoggingContext(name="main", server_name=homeserver_config.server.server_name):
-        start(homeserver_config, args)
+    main()
diff --git a/synapse/app/appservice.py b/synapse/app/appservice.py
index 823e1908b5..d251d0ab64 100644
--- a/synapse/app/appservice.py
+++ b/synapse/app/appservice.py
@@ -19,16 +19,11 @@
 #
 #
 
-import sys
-
-from synapse.app.generic_worker import load_config, start
-from synapse.util.logcontext import LoggingContext
+from synapse.app.generic_worker import main as worker_main
 
 
 def main() -> None:
-    homeserver_config = load_config(sys.argv[1:])
-    with LoggingContext(name="main", server_name=homeserver_config.server.server_name):
-        start(homeserver_config)
+    worker_main()
 
 
 if __name__ == "__main__":
diff --git a/synapse/app/client_reader.py b/synapse/app/client_reader.py
index 823e1908b5..d251d0ab64 100644
--- a/synapse/app/client_reader.py
+++ b/synapse/app/client_reader.py
@@ -19,16 +19,11 @@
 #
 #
 
-import sys
-
-from synapse.app.generic_worker import load_config, start
-from synapse.util.logcontext import LoggingContext
+from synapse.app.generic_worker import main as worker_main
 
 
 def main() -> None:
-    homeserver_config = load_config(sys.argv[1:])
-    with LoggingContext(name="main", server_name=homeserver_config.server.server_name):
-        start(homeserver_config)
+    worker_main()
 
 
 if __name__ == "__main__":
diff --git a/synapse/app/complement_fork_starter.py b/synapse/app/complement_fork_starter.py
index b981a7631b..dcb45e234b 100644
--- a/synapse/app/complement_fork_starter.py
+++ b/synapse/app/complement_fork_starter.py
@@ -26,13 +26,13 @@ import os
 import signal
 import sys
 from types import FrameType
-from typing import Any, Callable, Dict, List, Optional
+from typing import Any, Callable
 
 from twisted.internet.main import installReactor
 
 # a list of the original signal handlers, before we installed our custom ones.
 # We restore these in our child processes.
-_original_signal_handlers: Dict[int, Any] = {}
+_original_signal_handlers: dict[int, Any] = {}
 
 
 class ProxiedReactor:
@@ -72,7 +72,7 @@ class ProxiedReactor:
 
 
 def _worker_entrypoint(
-    func: Callable[[], None], proxy_reactor: ProxiedReactor, args: List[str]
+    func: Callable[[], None], proxy_reactor: ProxiedReactor, args: list[str]
 ) -> None:
     """
     Entrypoint for a forked worker process.
@@ -128,7 +128,7 @@ def main() -> None:
 
     # Split up the subsequent arguments into each workers' arguments;
     # `--` is our delimiter of choice.
-    args_by_worker: List[List[str]] = [
+    args_by_worker: list[list[str]] = [
         list(args)
         for cond, args in itertools.groupby(ns.args, lambda ele: ele != "--")
         if cond and args
@@ -167,12 +167,12 @@ def main() -> None:
     update_proc.join()
     print("===== PREPARED DATABASE =====", file=sys.stderr)
 
-    processes: List[multiprocessing.Process] = []
+    processes: list[multiprocessing.Process] = []
 
     # Install signal handlers to propagate signals to all our children, so that they
     # shut down cleanly. This also inhibits our own exit, but that's good: we want to
     # wait until the children have exited.
-    def handle_signal(signum: int, frame: Optional[FrameType]) -> None:
+    def handle_signal(signum: int, frame: FrameType | None) -> None:
         print(
             f"complement_fork_starter: Caught signal {signum}. Stopping children.",
             file=sys.stderr,
diff --git a/synapse/app/event_creator.py b/synapse/app/event_creator.py
index 1a9b0ad155..5b18578bd0 100644
--- a/synapse/app/event_creator.py
+++ b/synapse/app/event_creator.py
@@ -18,16 +18,11 @@
 #
 #
 
-import sys
-
-from synapse.app.generic_worker import load_config, start
-from synapse.util.logcontext import LoggingContext
+from synapse.app.generic_worker import main as worker_main
 
 
 def main() -> None:
-    homeserver_config = load_config(sys.argv[1:])
-    with LoggingContext(name="main", server_name=homeserver_config.server.server_name):
-        start(homeserver_config)
+    worker_main()
 
 
 if __name__ == "__main__":
diff --git a/synapse/app/federation_reader.py b/synapse/app/federation_reader.py
index 823e1908b5..d251d0ab64 100644
--- a/synapse/app/federation_reader.py
+++ b/synapse/app/federation_reader.py
@@ -19,16 +19,11 @@
 #
 #
 
-import sys
-
-from synapse.app.generic_worker import load_config, start
-from synapse.util.logcontext import LoggingContext
+from synapse.app.generic_worker import main as worker_main
 
 
 def main() -> None:
-    homeserver_config = load_config(sys.argv[1:])
-    with LoggingContext(name="main", server_name=homeserver_config.server.server_name):
-        start(homeserver_config)
+    worker_main()
 
 
 if __name__ == "__main__":
diff --git a/synapse/app/federation_sender.py b/synapse/app/federation_sender.py
index 823e1908b5..d251d0ab64 100644
--- a/synapse/app/federation_sender.py
+++ b/synapse/app/federation_sender.py
@@ -19,16 +19,11 @@
 #
 #
 
-import sys
-
-from synapse.app.generic_worker import load_config, start
-from synapse.util.logcontext import LoggingContext
+from synapse.app.generic_worker import main as worker_main
 
 
 def main() -> None:
-    homeserver_config = load_config(sys.argv[1:])
-    with LoggingContext(name="main", server_name=homeserver_config.server.server_name):
-        start(homeserver_config)
+    worker_main()
 
 
 if __name__ == "__main__":
diff --git a/synapse/app/frontend_proxy.py b/synapse/app/frontend_proxy.py
index 823e1908b5..d251d0ab64 100644
--- a/synapse/app/frontend_proxy.py
+++ b/synapse/app/frontend_proxy.py
@@ -19,16 +19,11 @@
 #
 #
 
-import sys
-
-from synapse.app.generic_worker import load_config, start
-from synapse.util.logcontext import LoggingContext
+from synapse.app.generic_worker import main as worker_main
 
 
 def main() -> None:
-    homeserver_config = load_config(sys.argv[1:])
-    with LoggingContext(name="main", server_name=homeserver_config.server.server_name):
-        start(homeserver_config)
+    worker_main()
 
 
 if __name__ == "__main__":
diff --git a/synapse/app/generic_worker.py b/synapse/app/generic_worker.py
index 51b8adaa27..9939c0fe7d 100644
--- a/synapse/app/generic_worker.py
+++ b/synapse/app/generic_worker.py
@@ -21,7 +21,6 @@
 #
 import logging
 import sys
-from typing import Dict, List
 
 from twisted.web.resource import Resource
 
@@ -112,7 +111,7 @@ from synapse.storage.databases.main.transactions import TransactionWorkerStore
 from synapse.storage.databases.main.ui_auth import UIAuthWorkerStore
 from synapse.storage.databases.main.user_directory import UserDirectoryStore
 from synapse.storage.databases.main.user_erasure_store import UserErasureWorkerStore
-from synapse.util import SYNAPSE_VERSION
+from synapse.types import ISynapseReactor
 from synapse.util.httpresourcetree import create_resource_tree
 
 logger = logging.getLogger("synapse.app.generic_worker")
@@ -182,7 +181,7 @@ class GenericWorkerServer(HomeServer):
 
         # We always include an admin resource that we populate with servlets as needed
         admin_resource = JsonResource(self, canonical_json=False)
-        resources: Dict[str, Resource] = {
+        resources: dict[str, Resource] = {
             # We always include a health resource.
             "/health": HealthResource(),
             "/_synapse/admin": admin_resource,
@@ -278,11 +277,13 @@ class GenericWorkerServer(HomeServer):
                 self._listen_http(listener)
             elif listener.type == "manhole":
                 if isinstance(listener, TCPListenerConfig):
-                    _base.listen_manhole(
-                        listener.bind_addresses,
-                        listener.port,
-                        manhole_settings=self.config.server.manhole_settings,
-                        manhole_globals={"hs": self},
+                    self._listening_services.extend(
+                        _base.listen_manhole(
+                            listener.bind_addresses,
+                            listener.port,
+                            manhole_settings=self.config.server.manhole_settings,
+                            manhole_globals={"hs": self},
+                        )
                     )
                 else:
                     raise ConfigError(
@@ -296,9 +297,11 @@ class GenericWorkerServer(HomeServer):
                     )
                 else:
                     if isinstance(listener, TCPListenerConfig):
-                        _base.listen_metrics(
-                            listener.bind_addresses,
-                            listener.port,
+                        self._metrics_listeners.extend(
+                            _base.listen_metrics(
+                                listener.bind_addresses,
+                                listener.port,
+                            )
                         )
                     else:
                         raise ConfigError(
@@ -311,7 +314,7 @@ class GenericWorkerServer(HomeServer):
         self.get_replication_command_handler().start_replication(self)
 
 
-def load_config(argv_options: List[str]) -> HomeServerConfig:
+def load_config(argv_options: list[str]) -> HomeServerConfig:
     """
     Parse the commandline and config files (does not generate config)
 
@@ -330,7 +333,30 @@ def load_config(argv_options: List[str]) -> HomeServerConfig:
     return config
 
 
-def start(config: HomeServerConfig) -> None:
+def create_homeserver(
+    config: HomeServerConfig,
+    reactor: ISynapseReactor | None = None,
+) -> GenericWorkerServer:
+    """
+    Create a homeserver instance for the Synapse worker process.
+
+    Our composable functions (`create_homeserver`, `setup`, `start`) should not exit the
+    Python process (call `exit(...)`) and instead raise exceptions which can be handled
+    by the caller as desired. This doesn't matter for the normal case of one Synapse
+    instance running in the Python process (as we're only affecting ourselves), but is
+    important when we have multiple Synapse homeserver tenants running in the same
+    Python process (c.f. Synapse Pro for small hosts) as we don't want some problem from
+    one tenant stopping the rest of the tenants.
+
+    Args:
+        config: The configuration for the homeserver.
+        reactor: Optionally provide a reactor to use. Can be useful in different
+            scenarios that you want control over the reactor, such as tests.
+
+    Returns:
+        A homeserver instance.
+    """
+
     # For backwards compatibility let any of the old app names.
     assert config.worker.worker_app in (
         "synapse.app.appservice",
@@ -355,39 +381,93 @@ def start(config: HomeServerConfig) -> None:
     hs = GenericWorkerServer(
         config.server.server_name,
         config=config,
-        version_string=f"Synapse/{SYNAPSE_VERSION}",
+        reactor=reactor,
     )
 
-    setup_logging(hs, config, use_worker_options=True)
+    return hs
+
+
+def setup(hs: GenericWorkerServer) -> None:
+    """
+    Setup a `GenericWorkerServer` (worker) instance.
+
+    Our composable functions (`create_homeserver`, `setup`, `start`) should not exit the
+    Python process (call `exit(...)`) and instead raise exceptions which can be handled
+    by the caller as desired. This doesn't matter for the normal case of one Synapse
+    instance running in the Python process (as we're only affecting ourselves), but is
+    important when we have multiple Synapse homeserver tenants running in the same
+    Python process (c.f. Synapse Pro for small hosts) as we don't want some problem from
+    one tenant stopping the rest of the tenants.
+
+    Args:
+        hs: The homeserver to setup.
+    """
+
+    setup_logging(hs, hs.config, use_worker_options=True)
 
     # Start the tracer
     init_tracer(hs)  # noqa
 
-    try:
-        hs.setup()
+    hs.setup()
 
-        # Ensure the replication streamer is always started in case we write to any
-        # streams. Will no-op if no streams can be written to by this worker.
-        hs.get_replication_streamer()
-    except Exception as e:
-        handle_startup_exception(e)
+    # Ensure the replication streamer is always started in case we write to any
+    # streams. Will no-op if no streams can be written to by this worker.
+    hs.get_replication_streamer()
 
-    async def start() -> None:
-        await _base.start(hs)
 
-    register_start(hs, start)
+async def start(
+    hs: GenericWorkerServer,
+    *,
+    freeze: bool = True,
+) -> None:
+    """
+    Should be called once the reactor is running.
 
-    # redirect stdio to the logs, if configured.
-    if not hs.config.logging.no_redirect_stdio:
-        redirect_stdio_to_logs()
+    Our composable functions (`create_homeserver`, `setup`, `start`) should not exit the
+    Python process (call `exit(...)`) and instead raise exceptions which can be handled
+    by the caller as desired. This doesn't matter for the normal case of one Synapse
+    instance running in the Python process (as we're only affecting ourselves), but is
+    important when we have multiple Synapse homeserver tenants running in the same
+    Python process (c.f. Synapse Pro for small hosts) as we don't want some problem from
+    one tenant stopping the rest of the tenants.
 
-    _base.start_worker_reactor("synapse-generic-worker", config)
+    Args:
+        hs: The homeserver to setup.
+        freeze: whether to freeze the homeserver base objects in the garbage collector.
+            May improve garbage collection performance by marking objects with an effectively
+            static lifetime as frozen so they don't need to be considered for cleanup.
+            If you ever want to `shutdown` the homeserver, this needs to be
+            False otherwise the homeserver cannot be garbage collected after `shutdown`.
+    """
+
+    await _base.start(hs, freeze=freeze)
 
 
 def main() -> None:
     homeserver_config = load_config(sys.argv[1:])
+
+    # Create a logging context as soon as possible so we can start associating
+    # everything with this homeserver.
     with LoggingContext(name="main", server_name=homeserver_config.server.server_name):
-        start(homeserver_config)
+        # Initialize and setup the homeserver
+        hs = create_homeserver(homeserver_config)
+        try:
+            setup(hs)
+        except Exception as e:
+            handle_startup_exception(e)
+
+        # For problems immediately apparent during initialization, we want to log to
+        # stderr in the terminal so that they are obvious and visible to the operator.
+        #
+        # Now that we're past the initialization stage, we can redirect anything printed
+        # to stdio to the logs, if configured.
+        if not homeserver_config.logging.no_redirect_stdio:
+            redirect_stdio_to_logs()
+
+        # Register a callback to be invoked once the reactor is running
+        register_start(hs, start, hs)
+
+        _base.start_worker_reactor("synapse-generic-worker", homeserver_config)
 
 
 if __name__ == "__main__":
diff --git a/synapse/app/homeserver.py b/synapse/app/homeserver.py
index 35d633d527..8fb906cdf7 100644
--- a/synapse/app/homeserver.py
+++ b/synapse/app/homeserver.py
@@ -22,7 +22,7 @@
 import logging
 import os
 import sys
-from typing import Dict, Iterable, List
+from typing import Iterable
 
 from twisted.internet.tcp import Port
 from twisted.web.resource import EncodingResourceWrapper, Resource
@@ -70,7 +70,7 @@ from synapse.rest.synapse.client import build_synapse_client_resource_tree
 from synapse.rest.well_known import well_known_resource
 from synapse.server import HomeServer
 from synapse.storage import DataStore
-from synapse.util.check_dependencies import VERSION, check_requirements
+from synapse.types import ISynapseReactor
 from synapse.util.httpresourcetree import create_resource_tree
 from synapse.util.module_loader import load_module
 
@@ -82,6 +82,10 @@ def gz_wrap(r: Resource) -> Resource:
 
 
 class SynapseHomeServer(HomeServer):
+    """
+    Homeserver class for the main Synapse process.
+    """
+
     DATASTORE_CLASS = DataStore
 
     def _listener_http(
@@ -94,7 +98,7 @@ class SynapseHomeServer(HomeServer):
         site_tag = listener_config.get_site_tag()
 
         # We always include a health resource.
-        resources: Dict[str, Resource] = {"/health": HealthResource()}
+        resources: dict[str, Resource] = {"/health": HealthResource()}
 
         for res in listener_config.http_options.resources:
             for name in res.names:
@@ -165,7 +169,7 @@ class SynapseHomeServer(HomeServer):
 
     def _configure_named_resource(
         self, name: str, compress: bool = False
-    ) -> Dict[str, Resource]:
+    ) -> dict[str, Resource]:
         """Build a resource map for a named resource
 
         Args:
@@ -175,7 +179,7 @@ class SynapseHomeServer(HomeServer):
         Returns:
             map from path to HTTP resource
         """
-        resources: Dict[str, Resource] = {}
+        resources: dict[str, Resource] = {}
         if name == "client":
             client_resource: Resource = ClientRestResource(self)
             if compress:
@@ -277,11 +281,13 @@ class SynapseHomeServer(HomeServer):
                 )
             elif listener.type == "manhole":
                 if isinstance(listener, TCPListenerConfig):
-                    _base.listen_manhole(
-                        listener.bind_addresses,
-                        listener.port,
-                        manhole_settings=self.config.server.manhole_settings,
-                        manhole_globals={"hs": self},
+                    self._listening_services.extend(
+                        _base.listen_manhole(
+                            listener.bind_addresses,
+                            listener.port,
+                            manhole_settings=self.config.server.manhole_settings,
+                            manhole_globals={"hs": self},
+                        )
                     )
                 else:
                     raise ConfigError(
@@ -294,9 +300,11 @@ class SynapseHomeServer(HomeServer):
                     )
                 else:
                     if isinstance(listener, TCPListenerConfig):
-                        _base.listen_metrics(
-                            listener.bind_addresses,
-                            listener.port,
+                        self._metrics_listeners.extend(
+                            _base.listen_metrics(
+                                listener.bind_addresses,
+                                listener.port,
+                            )
                         )
                     else:
                         raise ConfigError(
@@ -309,7 +317,7 @@ class SynapseHomeServer(HomeServer):
                 logger.warning("Unrecognized listener type: %s", listener.type)
 
 
-def load_or_generate_config(argv_options: List[str]) -> HomeServerConfig:
+def load_or_generate_config(argv_options: list[str]) -> HomeServerConfig:
     """
     Parse the commandline and config files
 
@@ -340,12 +348,25 @@ def load_or_generate_config(argv_options: List[str]) -> HomeServerConfig:
     return config
 
 
-def setup(config: HomeServerConfig) -> SynapseHomeServer:
+def create_homeserver(
+    config: HomeServerConfig,
+    reactor: ISynapseReactor | None = None,
+) -> SynapseHomeServer:
     """
-    Create and setup a Synapse homeserver instance given a configuration.
+    Create a homeserver instance for the Synapse main process.
+
+    Our composable functions (`create_homeserver`, `setup`, `start`) should not exit the
+    Python process (call `exit(...)`) and instead raise exceptions which can be handled
+    by the caller as desired. This doesn't matter for the normal case of one Synapse
+    instance running in the Python process (as we're only affecting ourselves), but is
+    important when we have multiple Synapse homeserver tenants running in the same
+    Python process (c.f. Synapse Pro for small hosts) as we don't want some problem from
+    one tenant stopping the rest of the tenants.
 
     Args:
         config: The configuration for the homeserver.
+        reactor: Optionally provide a reactor to use. Can be useful in different
+            scenarios that you want control over the reactor, such as tests.
 
     Returns:
         A homeserver instance.
@@ -353,10 +374,9 @@ def setup(config: HomeServerConfig) -> SynapseHomeServer:
 
     if config.worker.worker_app:
         raise ConfigError(
-            "You have specified `worker_app` in the config but are attempting to start a non-worker "
+            "You have specified `worker_app` in the config but are attempting to setup a non-worker "
             "instance. Please use `python -m synapse.app.generic_worker` instead (or remove the option if this is the main process)."
         )
-        sys.exit(1)
 
     events.USE_FROZEN_DICTS = config.server.use_frozen_dicts
     synapse.util.caches.TRACK_MEMORY_USAGE = config.caches.track_memory_usage
@@ -364,64 +384,91 @@ def setup(config: HomeServerConfig) -> SynapseHomeServer:
     if config.server.gc_seconds:
         synapse.metrics.MIN_TIME_BETWEEN_GCS = config.server.gc_seconds
 
-    if (
-        config.registration.enable_registration
-        and not config.registration.enable_registration_without_verification
-    ):
-        if (
-            not config.captcha.enable_registration_captcha
-            and not config.registration.registrations_require_3pid
-            and not config.registration.registration_requires_token
-        ):
-            raise ConfigError(
-                "You have enabled open registration without any verification. This is a known vector for "
-                "spam and abuse. If you would like to allow public registration, please consider adding email, "
-                "captcha, or token-based verification. Otherwise this check can be removed by setting the "
-                "`enable_registration_without_verification` config option to `true`."
-            )
-
     hs = SynapseHomeServer(
-        config.server.server_name,
+        hostname=config.server.server_name,
         config=config,
-        version_string=f"Synapse/{VERSION}",
+        reactor=reactor,
     )
 
-    setup_logging(hs, config, use_worker_options=False)
-
-    # Start the tracer
-    init_tracer(hs)  # noqa
-
-    logger.info("Setting up server")
-
-    try:
-        hs.setup()
-    except Exception as e:
-        handle_startup_exception(e)
-
-    async def start() -> None:
-        # Load the OIDC provider metadatas, if OIDC is enabled.
-        if hs.config.oidc.oidc_enabled:
-            oidc = hs.get_oidc_handler()
-            # Loading the provider metadata also ensures the provider config is valid.
-            await oidc.load_metadata()
-
-        await _base.start(hs)
-
-        hs.get_datastores().main.db_pool.updates.start_doing_background_updates()
-
-    register_start(hs, start)
-
     return hs
 
 
-def run(hs: HomeServer) -> None:
+def setup(
+    hs: SynapseHomeServer,
+) -> None:
+    """
+    Setup a `SynapseHomeServer` (main) instance.
+
+    Our composable functions (`create_homeserver`, `setup`, `start`) should not exit the
+    Python process (call `exit(...)`) and instead raise exceptions which can be handled
+    by the caller as desired. This doesn't matter for the normal case of one Synapse
+    instance running in the Python process (as we're only affecting ourselves), but is
+    important when we have multiple Synapse homeserver tenants running in the same
+    Python process (c.f. Synapse Pro for small hosts) as we don't want some problem from
+    one tenant stopping the rest of the tenants.
+
+    Args:
+        hs: The homeserver to setup.
+    """
+
+    setup_logging(hs, hs.config, use_worker_options=False)
+
+    # Log after we've configured logging.
+    logger.info("Setting up server")
+
+    # Start the tracer
+    init_tracer(hs)  # noqa
+
+    hs.setup()
+
+
+async def start(
+    hs: SynapseHomeServer,
+    *,
+    freeze: bool = True,
+) -> None:
+    """
+    Should be called once the reactor is running.
+
+    Our composable functions (`create_homeserver`, `setup`, `start`) should not exit the
+    Python process (call `exit(...)`) and instead raise exceptions which can be handled
+    by the caller as desired. This doesn't matter for the normal case of one Synapse
+    instance running in the Python process (as we're only affecting ourselves), but is
+    important when we have multiple Synapse homeserver tenants running in the same
+    Python process (c.f. Synapse Pro for small hosts) as we don't want some problem from
+    one tenant stopping the rest of the tenants.
+
+    Args:
+        hs: The homeserver to setup.
+        freeze: whether to freeze the homeserver base objects in the garbage collector.
+            May improve garbage collection performance by marking objects with an effectively
+            static lifetime as frozen so they don't need to be considered for cleanup.
+            If you ever want to `shutdown` the homeserver, this needs to be
+            False otherwise the homeserver cannot be garbage collected after `shutdown`.
+    """
+
+    await _base.start(hs, freeze=freeze)
+
+    # TODO: Feels like this should be moved somewhere else.
+    hs.get_datastores().main.db_pool.updates.start_doing_background_updates()
+
+
+def start_reactor(
+    config: HomeServerConfig,
+) -> None:
+    """
+    Start the reactor (Twisted event-loop).
+
+    Args:
+        config: The configuration for the homeserver.
+    """
     _base.start_reactor(
         "synapse-homeserver",
-        soft_file_limit=hs.config.server.soft_file_limit,
-        gc_thresholds=hs.config.server.gc_thresholds,
-        pid_file=hs.config.server.pid_file,
-        daemonize=hs.config.server.daemonize,
-        print_pidfile=hs.config.server.print_pidfile,
+        soft_file_limit=config.server.soft_file_limit,
+        gc_thresholds=config.server.gc_thresholds,
+        pid_file=config.server.pid_file,
+        daemonize=config.server.daemonize,
+        print_pidfile=config.server.print_pidfile,
         logger=logger,
     )
 
@@ -429,16 +476,28 @@ def run(hs: HomeServer) -> None:
 def main() -> None:
     homeserver_config = load_or_generate_config(sys.argv[1:])
 
+    # Create a logging context as soon as possible so we can start associating
+    # everything with this homeserver.
     with LoggingContext(name="main", server_name=homeserver_config.server.server_name):
-        # check base requirements
-        check_requirements()
-        hs = setup(homeserver_config)
+        # Initialize and setup the homeserver
+        hs = create_homeserver(homeserver_config)
+        try:
+            setup(hs)
+        except Exception as e:
+            handle_startup_exception(e)
 
-        # redirect stdio to the logs, if configured.
-        if not hs.config.logging.no_redirect_stdio:
+        # For problems immediately apparent during initialization, we want to log to
+        # stderr in the terminal so that they are obvious and visible to the operator.
+        #
+        # Now that we're past the initialization stage, we can redirect anything printed
+        # to stdio to the logs, if configured.
+        if not homeserver_config.logging.no_redirect_stdio:
             redirect_stdio_to_logs()
 
-        run(hs)
+        # Register a callback to be invoked once the reactor is running
+        register_start(hs, start, hs)
+
+        start_reactor(homeserver_config)
 
 
 if __name__ == "__main__":
diff --git a/synapse/app/media_repository.py b/synapse/app/media_repository.py
index 823e1908b5..d251d0ab64 100644
--- a/synapse/app/media_repository.py
+++ b/synapse/app/media_repository.py
@@ -19,16 +19,11 @@
 #
 #
 
-import sys
-
-from synapse.app.generic_worker import load_config, start
-from synapse.util.logcontext import LoggingContext
+from synapse.app.generic_worker import main as worker_main
 
 
 def main() -> None:
-    homeserver_config = load_config(sys.argv[1:])
-    with LoggingContext(name="main", server_name=homeserver_config.server.server_name):
-        start(homeserver_config)
+    worker_main()
 
 
 if __name__ == "__main__":
diff --git a/synapse/app/phone_stats_home.py b/synapse/app/phone_stats_home.py
index 69d3ac78fd..13a0e3db7c 100644
--- a/synapse/app/phone_stats_home.py
+++ b/synapse/app/phone_stats_home.py
@@ -22,26 +22,25 @@ import logging
 import math
 import resource
 import sys
-from typing import TYPE_CHECKING, List, Mapping, Sized, Tuple
+from typing import TYPE_CHECKING, Mapping, Sized
 
 from prometheus_client import Gauge
 
 from twisted.internet import defer
 
 from synapse.metrics import SERVER_NAME_LABEL
-from synapse.metrics.background_process_metrics import (
-    run_as_background_process,
-)
 from synapse.types import JsonDict
-from synapse.util.constants import ONE_HOUR_SECONDS, ONE_MINUTE_SECONDS
+from synapse.util.constants import (
+    MILLISECONDS_PER_SECOND,
+    ONE_HOUR_SECONDS,
+    ONE_MINUTE_SECONDS,
+)
 
 if TYPE_CHECKING:
     from synapse.server import HomeServer
 
 logger = logging.getLogger("synapse.app.homeserver")
 
-MILLISECONDS_PER_SECOND = 1000
-
 INITIAL_DELAY_BEFORE_FIRST_PHONE_HOME_SECONDS = 5 * ONE_MINUTE_SECONDS
 """
 We wait 5 minutes to send the first set of stats as the server can be quite busy the
@@ -55,7 +54,7 @@ Phone home stats are sent every 3 hours
 
 # Contains the list of processes we will be monitoring
 # currently either 0 or 1
-_stats_process: List[Tuple[int, "resource.struct_rusage"]] = []
+_stats_process: list[tuple[int, "resource.struct_rusage"]] = []
 
 # Gauges to expose monthly active user control metrics
 current_mau_gauge = Gauge(
@@ -83,14 +82,12 @@ registered_reserved_users_mau_gauge = Gauge(
 def phone_stats_home(
     hs: "HomeServer",
     stats: JsonDict,
-    stats_process: List[Tuple[int, "resource.struct_rusage"]] = _stats_process,
+    stats_process: list[tuple[int, "resource.struct_rusage"]] = _stats_process,
 ) -> "defer.Deferred[None]":
-    server_name = hs.hostname
-
     async def _phone_stats_home(
         hs: "HomeServer",
         stats: JsonDict,
-        stats_process: List[Tuple[int, "resource.struct_rusage"]] = _stats_process,
+        stats_process: list[tuple[int, "resource.struct_rusage"]] = _stats_process,
     ) -> None:
         """Collect usage statistics and send them to the configured endpoint.
 
@@ -200,8 +197,8 @@ def phone_stats_home(
         except Exception as e:
             logger.warning("Error reporting stats: %s", e)
 
-    return run_as_background_process(
-        "phone_stats_home", server_name, _phone_stats_home, hs, stats, stats_process
+    return hs.run_as_background_process(
+        "phone_stats_home", _phone_stats_home, hs, stats, stats_process
     )
 
 
@@ -263,9 +260,8 @@ def start_phone_stats_home(hs: "HomeServer") -> None:
                 float(hs.config.server.max_mau_value)
             )
 
-        return run_as_background_process(
+        return hs.run_as_background_process(
             "generate_monthly_active_users",
-            server_name,
             _generate_monthly_active_users,
         )
 
@@ -285,10 +281,16 @@ def start_phone_stats_home(hs: "HomeServer") -> None:
 
         # We need to defer this init for the cases that we daemonize
         # otherwise the process ID we get is that of the non-daemon process
-        clock.call_later(0, performance_stats_init)
+        clock.call_later(
+            0,
+            performance_stats_init,
+        )
 
         # We wait 5 minutes to send the first set of stats as the server can
         # be quite busy the first few minutes
         clock.call_later(
-            INITIAL_DELAY_BEFORE_FIRST_PHONE_HOME_SECONDS, phone_stats_home, hs, stats
+            INITIAL_DELAY_BEFORE_FIRST_PHONE_HOME_SECONDS,
+            phone_stats_home,
+            hs,
+            stats,
         )
diff --git a/synapse/app/pusher.py b/synapse/app/pusher.py
index 823e1908b5..d251d0ab64 100644
--- a/synapse/app/pusher.py
+++ b/synapse/app/pusher.py
@@ -19,16 +19,11 @@
 #
 #
 
-import sys
-
-from synapse.app.generic_worker import load_config, start
-from synapse.util.logcontext import LoggingContext
+from synapse.app.generic_worker import main as worker_main
 
 
 def main() -> None:
-    homeserver_config = load_config(sys.argv[1:])
-    with LoggingContext(name="main", server_name=homeserver_config.server.server_name):
-        start(homeserver_config)
+    worker_main()
 
 
 if __name__ == "__main__":
diff --git a/synapse/app/synchrotron.py b/synapse/app/synchrotron.py
index 823e1908b5..d251d0ab64 100644
--- a/synapse/app/synchrotron.py
+++ b/synapse/app/synchrotron.py
@@ -19,16 +19,11 @@
 #
 #
 
-import sys
-
-from synapse.app.generic_worker import load_config, start
-from synapse.util.logcontext import LoggingContext
+from synapse.app.generic_worker import main as worker_main
 
 
 def main() -> None:
-    homeserver_config = load_config(sys.argv[1:])
-    with LoggingContext(name="main", server_name=homeserver_config.server.server_name):
-        start(homeserver_config)
+    worker_main()
 
 
 if __name__ == "__main__":
diff --git a/synapse/app/user_dir.py b/synapse/app/user_dir.py
index f64d82e41f..2c47d9f4fd 100644
--- a/synapse/app/user_dir.py
+++ b/synapse/app/user_dir.py
@@ -19,16 +19,12 @@
 #
 #
 
-import sys
 
-from synapse.app.generic_worker import load_config, start
-from synapse.util.logcontext import LoggingContext
+from synapse.app.generic_worker import main as worker_main
 
 
 def main() -> None:
-    homeserver_config = load_config(sys.argv[1:])
-    with LoggingContext(name="main", server_name=homeserver_config.server.server_name):
-        start(homeserver_config)
+    worker_main()
 
 
 if __name__ == "__main__":
diff --git a/synapse/appservice/__init__.py b/synapse/appservice/__init__.py
index 2d8d382e68..620aa29dfc 100644
--- a/synapse/appservice/__init__.py
+++ b/synapse/appservice/__init__.py
@@ -23,15 +23,30 @@
 import logging
 import re
 from enum import Enum
-from typing import TYPE_CHECKING, Dict, Iterable, List, Optional, Pattern, Sequence
+from typing import (
+    TYPE_CHECKING,
+    Iterable,
+    Pattern,
+    Sequence,
+    cast,
+)
 
 import attr
 from netaddr import IPSet
 
+from twisted.internet import reactor
+
 from synapse.api.constants import EventTypes
 from synapse.events import EventBase
-from synapse.types import DeviceListUpdates, JsonDict, JsonMapping, UserID
+from synapse.types import (
+    DeviceListUpdates,
+    ISynapseThreadlessReactor,
+    JsonDict,
+    JsonMapping,
+    UserID,
+)
 from synapse.util.caches.descriptors import _CacheContext, cached
+from synapse.util.clock import Clock
 
 if TYPE_CHECKING:
     from synapse.appservice.api import ApplicationServiceApi
@@ -41,11 +56,11 @@ logger = logging.getLogger(__name__)
 
 # Type for the `device_one_time_keys_count` field in an appservice transaction
 #   user ID -> {device ID -> {algorithm -> count}}
-TransactionOneTimeKeysCount = Dict[str, Dict[str, Dict[str, int]]]
+TransactionOneTimeKeysCount = dict[str, dict[str, dict[str, int]]]
 
 # Type for the `device_unused_fallback_key_types` field in an appservice transaction
 #   user ID -> {device ID -> [algorithm]}
-TransactionUnusedFallbackKeys = Dict[str, Dict[str, List[str]]]
+TransactionUnusedFallbackKeys = dict[str, dict[str, list[str]]]
 
 
 class ApplicationServiceState(Enum):
@@ -79,12 +94,12 @@ class ApplicationService:
         token: str,
         id: str,
         sender: UserID,
-        url: Optional[str] = None,
-        namespaces: Optional[JsonDict] = None,
-        hs_token: Optional[str] = None,
-        protocols: Optional[Iterable[str]] = None,
+        url: str | None = None,
+        namespaces: JsonDict | None = None,
+        hs_token: str | None = None,
+        protocols: Iterable[str] | None = None,
         rate_limited: bool = True,
-        ip_range_whitelist: Optional[IPSet] = None,
+        ip_range_whitelist: IPSet | None = None,
         supports_ephemeral: bool = False,
         msc3202_transaction_extensions: bool = False,
         msc4190_device_management: bool = False,
@@ -98,6 +113,15 @@ class ApplicationService:
         self.sender = sender
         # The application service user should be part of the server's domain.
         self.server_name = sender.domain  # nb must be called this for @cached
+
+        # Ideally we would require passing in the `HomeServer` `Clock` instance.
+        # However this is not currently possible as there are places which use
+        # `@cached` that aren't aware of the `HomeServer` instance.
+        # nb must be called this for @cached
+        self.clock = Clock(
+            cast(ISynapseThreadlessReactor, reactor), server_name=self.server_name
+        )  # type: ignore[multiple-internal-clocks]
+
         self.namespaces = self._check_namespaces(namespaces)
         self.id = id
         self.ip_range_whitelist = ip_range_whitelist
@@ -117,8 +141,8 @@ class ApplicationService:
         self.rate_limited = rate_limited
 
     def _check_namespaces(
-        self, namespaces: Optional[JsonDict]
-    ) -> Dict[str, List[Namespace]]:
+        self, namespaces: JsonDict | None
+    ) -> dict[str, list[Namespace]]:
         # Sanity check that it is of the form:
         # {
         #   users: [ {regex: "[A-z]+.*", exclusive: true}, ...],
@@ -128,7 +152,7 @@ class ApplicationService:
         if namespaces is None:
             namespaces = {}
 
-        result: Dict[str, List[Namespace]] = {}
+        result: dict[str, list[Namespace]] = {}
 
         for ns in ApplicationService.NS_LIST:
             result[ns] = []
@@ -154,9 +178,7 @@ class ApplicationService:
 
         return result
 
-    def _matches_regex(
-        self, namespace_key: str, test_string: str
-    ) -> Optional[Namespace]:
+    def _matches_regex(self, namespace_key: str, test_string: str) -> Namespace | None:
         for namespace in self.namespaces[namespace_key]:
             if namespace.regex.match(test_string):
                 return namespace
@@ -361,7 +383,7 @@ class ApplicationService:
     def is_exclusive_room(self, room_id: str) -> bool:
         return self._is_exclusive(ApplicationService.NS_ROOMS, room_id)
 
-    def get_exclusive_user_regexes(self) -> List[Pattern[str]]:
+    def get_exclusive_user_regexes(self) -> list[Pattern[str]]:
         """Get the list of regexes used to determine if a user is exclusively
         registered by the AS
         """
@@ -390,8 +412,8 @@ class AppServiceTransaction:
         service: ApplicationService,
         id: int,
         events: Sequence[EventBase],
-        ephemeral: List[JsonMapping],
-        to_device_messages: List[JsonMapping],
+        ephemeral: list[JsonMapping],
+        to_device_messages: list[JsonMapping],
         one_time_keys_count: TransactionOneTimeKeysCount,
         unused_fallback_keys: TransactionUnusedFallbackKeys,
         device_list_summary: DeviceListUpdates,
diff --git a/synapse/appservice/api.py b/synapse/appservice/api.py
index 55069cc5d3..71094de9be 100644
--- a/synapse/appservice/api.py
+++ b/synapse/appservice/api.py
@@ -23,15 +23,10 @@ import logging
 import urllib.parse
 from typing import (
     TYPE_CHECKING,
-    Dict,
     Iterable,
-    List,
     Mapping,
-    Optional,
     Sequence,
-    Tuple,
     TypeVar,
-    Union,
 )
 
 from prometheus_client import Counter
@@ -133,14 +128,14 @@ class ApplicationServiceApi(SimpleHttpClient):
         self.clock = hs.get_clock()
         self.config = hs.config.appservice
 
-        self.protocol_meta_cache: ResponseCache[Tuple[str, str]] = ResponseCache(
+        self.protocol_meta_cache: ResponseCache[tuple[str, str]] = ResponseCache(
             clock=hs.get_clock(),
             name="as_protocol_meta",
             server_name=self.server_name,
             timeout_ms=HOUR_IN_MS,
         )
 
-    def _get_headers(self, service: "ApplicationService") -> Dict[bytes, List[bytes]]:
+    def _get_headers(self, service: "ApplicationService") -> dict[bytes, list[bytes]]:
         """This makes sure we have always the auth header and opentracing headers set."""
 
         # This is also ensured before in the functions. However this is needed to please
@@ -210,8 +205,8 @@ class ApplicationServiceApi(SimpleHttpClient):
         service: "ApplicationService",
         kind: str,
         protocol: str,
-        fields: Dict[bytes, List[bytes]],
-    ) -> List[JsonDict]:
+        fields: dict[bytes, list[bytes]],
+    ) -> list[JsonDict]:
         if kind == ThirdPartyEntityKind.USER:
             required_field = "userid"
         elif kind == ThirdPartyEntityKind.LOCATION:
@@ -225,7 +220,7 @@ class ApplicationServiceApi(SimpleHttpClient):
         assert service.hs_token is not None
 
         try:
-            args: Mapping[bytes, Union[List[bytes], str]] = fields
+            args: Mapping[bytes, list[bytes] | str] = fields
             if self.config.use_appservice_legacy_authorization:
                 args = {
                     **fields,
@@ -261,11 +256,11 @@ class ApplicationServiceApi(SimpleHttpClient):
 
     async def get_3pe_protocol(
         self, service: "ApplicationService", protocol: str
-    ) -> Optional[JsonDict]:
+    ) -> JsonDict | None:
         if service.url is None:
             return {}
 
-        async def _get() -> Optional[JsonDict]:
+        async def _get() -> JsonDict | None:
             # This is required by the configuration.
             assert service.hs_token is not None
             try:
@@ -303,7 +298,7 @@ class ApplicationServiceApi(SimpleHttpClient):
         key = (service.id, protocol)
         return await self.protocol_meta_cache.wrap(key, _get)
 
-    async def ping(self, service: "ApplicationService", txn_id: Optional[str]) -> None:
+    async def ping(self, service: "ApplicationService", txn_id: str | None) -> None:
         # The caller should check that url is set
         assert service.url is not None, "ping called without URL being set"
 
@@ -320,12 +315,12 @@ class ApplicationServiceApi(SimpleHttpClient):
         self,
         service: "ApplicationService",
         events: Sequence[EventBase],
-        ephemeral: List[JsonMapping],
-        to_device_messages: List[JsonMapping],
+        ephemeral: list[JsonMapping],
+        to_device_messages: list[JsonMapping],
         one_time_keys_count: TransactionOneTimeKeysCount,
         unused_fallback_keys: TransactionUnusedFallbackKeys,
         device_list_summary: DeviceListUpdates,
-        txn_id: Optional[int] = None,
+        txn_id: int | None = None,
     ) -> bool:
         """
         Push data to an application service.
@@ -429,9 +424,9 @@ class ApplicationServiceApi(SimpleHttpClient):
         return False
 
     async def claim_client_keys(
-        self, service: "ApplicationService", query: List[Tuple[str, str, str, int]]
-    ) -> Tuple[
-        Dict[str, Dict[str, Dict[str, JsonDict]]], List[Tuple[str, str, str, int]]
+        self, service: "ApplicationService", query: list[tuple[str, str, str, int]]
+    ) -> tuple[
+        dict[str, dict[str, dict[str, JsonDict]]], list[tuple[str, str, str, int]]
     ]:
         """Claim one time keys from an application service.
 
@@ -457,7 +452,7 @@ class ApplicationServiceApi(SimpleHttpClient):
         assert service.hs_token is not None
 
         # Create the expected payload shape.
-        body: Dict[str, Dict[str, List[str]]] = {}
+        body: dict[str, dict[str, list[str]]] = {}
         for user_id, device, algorithm, count in query:
             body.setdefault(user_id, {}).setdefault(device, []).extend(
                 [algorithm] * count
@@ -502,8 +497,8 @@ class ApplicationServiceApi(SimpleHttpClient):
         return response, missing
 
     async def query_keys(
-        self, service: "ApplicationService", query: Dict[str, List[str]]
-    ) -> Dict[str, Dict[str, Dict[str, JsonDict]]]:
+        self, service: "ApplicationService", query: dict[str, list[str]]
+    ) -> dict[str, dict[str, dict[str, JsonDict]]]:
         """Query the application service for keys.
 
         Note that any error (including a timeout) is treated as the application
@@ -545,7 +540,7 @@ class ApplicationServiceApi(SimpleHttpClient):
 
     def _serialize(
         self, service: "ApplicationService", events: Iterable[EventBase]
-    ) -> List[JsonDict]:
+    ) -> list[JsonDict]:
         time_now = self.clock.time_msec()
         return [
             serialize_event(
diff --git a/synapse/appservice/scheduler.py b/synapse/appservice/scheduler.py
index c8678406a1..30c22780bd 100644
--- a/synapse/appservice/scheduler.py
+++ b/synapse/appservice/scheduler.py
@@ -61,13 +61,8 @@ from typing import (
     Awaitable,
     Callable,
     Collection,
-    Dict,
     Iterable,
-    List,
-    Optional,
     Sequence,
-    Set,
-    Tuple,
 )
 
 from twisted.internet.interfaces import IDelayedCall
@@ -81,7 +76,6 @@ from synapse.appservice import (
 from synapse.appservice.api import ApplicationServiceApi
 from synapse.events import EventBase
 from synapse.logging.context import run_in_background
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.storage.databases.main import DataStore
 from synapse.types import DeviceListUpdates, JsonMapping
 from synapse.util.clock import Clock
@@ -128,10 +122,10 @@ class ApplicationServiceScheduler:
     def enqueue_for_appservice(
         self,
         appservice: ApplicationService,
-        events: Optional[Collection[EventBase]] = None,
-        ephemeral: Optional[Collection[JsonMapping]] = None,
-        to_device_messages: Optional[Collection[JsonMapping]] = None,
-        device_list_summary: Optional[DeviceListUpdates] = None,
+        events: Collection[EventBase] | None = None,
+        ephemeral: Collection[JsonMapping] | None = None,
+        to_device_messages: Collection[JsonMapping] | None = None,
+        device_list_summary: DeviceListUpdates | None = None,
     ) -> None:
         """
         Enqueue some data to be sent off to an application service.
@@ -184,22 +178,23 @@ class _ServiceQueuer:
 
     def __init__(self, txn_ctrl: "_TransactionController", hs: "HomeServer"):
         # dict of {service_id: [events]}
-        self.queued_events: Dict[str, List[EventBase]] = {}
+        self.queued_events: dict[str, list[EventBase]] = {}
         # dict of {service_id: [events]}
-        self.queued_ephemeral: Dict[str, List[JsonMapping]] = {}
+        self.queued_ephemeral: dict[str, list[JsonMapping]] = {}
         # dict of {service_id: [to_device_message_json]}
-        self.queued_to_device_messages: Dict[str, List[JsonMapping]] = {}
+        self.queued_to_device_messages: dict[str, list[JsonMapping]] = {}
         # dict of {service_id: [device_list_summary]}
-        self.queued_device_list_summaries: Dict[str, List[DeviceListUpdates]] = {}
+        self.queued_device_list_summaries: dict[str, list[DeviceListUpdates]] = {}
 
         # the appservices which currently have a transaction in flight
-        self.requests_in_flight: Set[str] = set()
+        self.requests_in_flight: set[str] = set()
         self.txn_ctrl = txn_ctrl
         self._msc3202_transaction_extensions_enabled: bool = (
             hs.config.experimental.msc3202_transaction_extensions
         )
         self.server_name = hs.hostname
         self.clock = hs.get_clock()
+        self.hs = hs
         self._store = hs.get_datastores().main
 
     def start_background_request(self, service: ApplicationService) -> None:
@@ -207,9 +202,7 @@ class _ServiceQueuer:
         if service.id in self.requests_in_flight:
             return
 
-        run_as_background_process(
-            "as-sender", self.server_name, self._send_request, service
-        )
+        self.hs.run_as_background_process("as-sender", self._send_request, service)
 
     async def _send_request(self, service: ApplicationService) -> None:
         # sanity-check: we shouldn't get here if this service already has a sender
@@ -266,8 +259,8 @@ class _ServiceQueuer:
                 ):
                     return
 
-                one_time_keys_count: Optional[TransactionOneTimeKeysCount] = None
-                unused_fallback_keys: Optional[TransactionUnusedFallbackKeys] = None
+                one_time_keys_count: TransactionOneTimeKeysCount | None = None
+                unused_fallback_keys: TransactionUnusedFallbackKeys | None = None
 
                 if (
                     self._msc3202_transaction_extensions_enabled
@@ -304,7 +297,7 @@ class _ServiceQueuer:
         events: Iterable[EventBase],
         ephemerals: Iterable[JsonMapping],
         to_device_messages: Iterable[JsonMapping],
-    ) -> Tuple[TransactionOneTimeKeysCount, TransactionUnusedFallbackKeys]:
+    ) -> tuple[TransactionOneTimeKeysCount, TransactionUnusedFallbackKeys]:
         """
         Given a list of the events, ephemeral messages and to-device messages,
         - first computes a list of application services users that may have
@@ -315,14 +308,14 @@ class _ServiceQueuer:
         """
 
         # Set of 'interesting' users who may have updates
-        users: Set[str] = set()
+        users: set[str] = set()
 
         # The sender is always included
         users.add(service.sender.to_string())
 
         # All AS users that would receive the PDUs or EDUs sent to these rooms
         # are classed as 'interesting'.
-        rooms_of_interesting_users: Set[str] = set()
+        rooms_of_interesting_users: set[str] = set()
         # PDUs
         rooms_of_interesting_users.update(event.room_id for event in events)
         # EDUs
@@ -361,11 +354,12 @@ class _TransactionController:
     def __init__(self, hs: "HomeServer"):
         self.server_name = hs.hostname
         self.clock = hs.get_clock()
+        self.hs = hs
         self.store = hs.get_datastores().main
         self.as_api = hs.get_application_service_api()
 
         # map from service id to recoverer instance
-        self.recoverers: Dict[str, "_Recoverer"] = {}
+        self.recoverers: dict[str, "_Recoverer"] = {}
 
         # for UTs
         self.RECOVERER_CLASS = _Recoverer
@@ -374,11 +368,11 @@ class _TransactionController:
         self,
         service: ApplicationService,
         events: Sequence[EventBase],
-        ephemeral: Optional[List[JsonMapping]] = None,
-        to_device_messages: Optional[List[JsonMapping]] = None,
-        one_time_keys_count: Optional[TransactionOneTimeKeysCount] = None,
-        unused_fallback_keys: Optional[TransactionUnusedFallbackKeys] = None,
-        device_list_summary: Optional[DeviceListUpdates] = None,
+        ephemeral: list[JsonMapping] | None = None,
+        to_device_messages: list[JsonMapping] | None = None,
+        one_time_keys_count: TransactionOneTimeKeysCount | None = None,
+        unused_fallback_keys: TransactionUnusedFallbackKeys | None = None,
+        device_list_summary: DeviceListUpdates | None = None,
     ) -> None:
         """
         Create a transaction with the given data and send to the provided
@@ -448,6 +442,7 @@ class _TransactionController:
         recoverer = self.RECOVERER_CLASS(
             self.server_name,
             self.clock,
+            self.hs,
             self.store,
             self.as_api,
             service,
@@ -494,6 +489,7 @@ class _Recoverer:
         self,
         server_name: str,
         clock: Clock,
+        hs: "HomeServer",
         store: DataStore,
         as_api: ApplicationServiceApi,
         service: ApplicationService,
@@ -501,21 +497,21 @@ class _Recoverer:
     ):
         self.server_name = server_name
         self.clock = clock
+        self.hs = hs
         self.store = store
         self.as_api = as_api
         self.service = service
         self.callback = callback
         self.backoff_counter = 1
-        self.scheduled_recovery: Optional[IDelayedCall] = None
+        self.scheduled_recovery: IDelayedCall | None = None
 
     def recover(self) -> None:
         delay = 2**self.backoff_counter
         logger.info("Scheduling retries on %s in %fs", self.service.id, delay)
         self.scheduled_recovery = self.clock.call_later(
             delay,
-            run_as_background_process,
+            self.hs.run_as_background_process,
             "as-recoverer",
-            self.server_name,
             self.retry,
         )
 
@@ -535,9 +531,8 @@ class _Recoverer:
         if self.scheduled_recovery:
             self.clock.cancel_call_later(self.scheduled_recovery)
         # Run a retry, which will resechedule a recovery if it fails.
-        run_as_background_process(
+        self.hs.run_as_background_process(
             "retry",
-            self.server_name,
             self.retry,
         )
 
diff --git a/synapse/config/__main__.py b/synapse/config/__main__.py
index ef9d36b507..9169b062bf 100644
--- a/synapse/config/__main__.py
+++ b/synapse/config/__main__.py
@@ -20,13 +20,12 @@
 #
 #
 import sys
-from typing import List
 
 from synapse.config._base import ConfigError
 from synapse.config.homeserver import HomeServerConfig
 
 
-def main(args: List[str]) -> None:
+def main(args: list[str]) -> None:
     action = args[1] if len(args) > 1 and args[1] == "read" else None
     # If we're reading a key in the config file, then `args[1]` will be `read`  and `args[2]`
     # will be the key to read.
diff --git a/synapse/config/_base.py b/synapse/config/_base.py
index 6de4c12c96..95a00c6718 100644
--- a/synapse/config/_base.py
+++ b/synapse/config/_base.py
@@ -33,16 +33,10 @@ from textwrap import dedent
 from typing import (
     Any,
     ClassVar,
-    Dict,
     Iterable,
     Iterator,
-    List,
     MutableMapping,
-    Optional,
-    Tuple,
-    Type,
     TypeVar,
-    Union,
 )
 
 import attr
@@ -64,7 +58,7 @@ class ConfigError(Exception):
            the problem lies.
     """
 
-    def __init__(self, msg: str, path: Optional[StrSequence] = None):
+    def __init__(self, msg: str, path: StrSequence | None = None):
         self.msg = msg
         self.path = path
 
@@ -179,7 +173,7 @@ class Config:
         )
 
     @staticmethod
-    def parse_size(value: Union[str, int]) -> int:
+    def parse_size(value: str | int) -> int:
         """Interpret `value` as a number of bytes.
 
         If an integer is provided it is treated as bytes and is unchanged.
@@ -206,7 +200,7 @@ class Config:
             raise TypeError(f"Bad byte size {value!r}")
 
     @staticmethod
-    def parse_duration(value: Union[str, int]) -> int:
+    def parse_duration(value: str | int) -> int:
         """Convert a duration as a string or integer to a number of milliseconds.
 
         If an integer is provided it is treated as milliseconds and is unchanged.
@@ -274,7 +268,7 @@ class Config:
         return path_exists(file_path)
 
     @classmethod
-    def check_file(cls, file_path: Optional[str], config_name: str) -> str:
+    def check_file(cls, file_path: str | None, config_name: str) -> str:
         if file_path is None:
             raise ConfigError("Missing config for %s." % (config_name,))
         try:
@@ -321,9 +315,9 @@ class Config:
 
     def read_templates(
         self,
-        filenames: List[str],
-        custom_template_directories: Optional[Iterable[str]] = None,
-    ) -> List[jinja2.Template]:
+        filenames: list[str],
+        custom_template_directories: Iterable[str] | None = None,
+    ) -> list[jinja2.Template]:
         """Load a list of template files from disk using the given variables.
 
         This function will attempt to load the given templates from the default Synapse
@@ -402,7 +396,7 @@ class RootConfig:
     class, lower-cased and with "Config" removed.
     """
 
-    config_classes: List[Type[Config]] = []
+    config_classes: list[type[Config]] = []
 
     def __init__(self, config_files: StrSequence = ()):
         # Capture absolute paths here, so we can reload config after we daemonize.
@@ -469,11 +463,11 @@ class RootConfig:
         data_dir_path: str,
         server_name: str,
         generate_secrets: bool = False,
-        report_stats: Optional[bool] = None,
+        report_stats: bool | None = None,
         open_private_ports: bool = False,
-        listeners: Optional[List[dict]] = None,
-        tls_certificate_path: Optional[str] = None,
-        tls_private_key_path: Optional[str] = None,
+        listeners: list[dict] | None = None,
+        tls_certificate_path: str | None = None,
+        tls_private_key_path: str | None = None,
     ) -> str:
         """
         Build a default configuration file
@@ -545,18 +539,22 @@ class RootConfig:
 
     @classmethod
     def load_config(
-        cls: Type[TRootConfig], description: str, argv: List[str]
+        cls: type[TRootConfig], description: str, argv_options: list[str]
     ) -> TRootConfig:
         """Parse the commandline and config files
 
         Doesn't support config-file-generation: used by the worker apps.
 
+        Args:
+            description: TODO
+            argv_options: The options passed to Synapse. Usually `sys.argv[1:]`.
+
         Returns:
             Config object.
         """
         config_parser = argparse.ArgumentParser(description=description)
         cls.add_arguments_to_parser(config_parser)
-        obj, _ = cls.load_config_with_parser(config_parser, argv)
+        obj, _ = cls.load_config_with_parser(config_parser, argv_options)
 
         return obj
 
@@ -601,14 +599,18 @@ class RootConfig:
 
     @classmethod
     def load_config_with_parser(
-        cls: Type[TRootConfig], parser: argparse.ArgumentParser, argv_options: List[str]
-    ) -> Tuple[TRootConfig, argparse.Namespace]:
+        cls: type[TRootConfig], parser: argparse.ArgumentParser, argv_options: list[str]
+    ) -> tuple[TRootConfig, argparse.Namespace]:
         """Parse the commandline and config files with the given parser
 
         Doesn't support config-file-generation: used by the worker apps.
 
         Used for workers where we want to add extra flags/subcommands.
 
+        Note: This is the common denominator for loading config and is also used by
+        `load_config` and `load_or_generate_config`. Which is why we call
+        `validate_config()` here.
+
         Args:
             parser
             argv_options: The options passed to Synapse. Usually `sys.argv[1:]`.
@@ -642,12 +644,16 @@ class RootConfig:
 
         obj.invoke_all("read_arguments", config_args)
 
+        # Now that we finally have the full config sections parsed, allow subclasses to
+        # do some extra validation across the entire config.
+        obj.validate_config()
+
         return obj, config_args
 
     @classmethod
     def load_or_generate_config(
-        cls: Type[TRootConfig], description: str, argv_options: List[str]
-    ) -> Optional[TRootConfig]:
+        cls: type[TRootConfig], description: str, argv_options: list[str]
+    ) -> TRootConfig | None:
         """Parse the commandline and config files
 
         Supports generation of config files, so is used for the main homeserver app.
@@ -842,19 +848,11 @@ class RootConfig:
         ):
             return None
 
-        obj.parse_config_dict(
-            config_dict,
-            config_dir_path=config_dir_path,
-            data_dir_path=data_dir_path,
-            allow_secrets_in_config=config_args.secrets_in_config,
-        )
-        obj.invoke_all("read_arguments", config_args)
-
-        return obj
+        return cls.load_config(description, argv_options)
 
     def parse_config_dict(
         self,
-        config_dict: Dict[str, Any],
+        config_dict: dict[str, Any],
         config_dir_path: str,
         data_dir_path: str,
         allow_secrets_in_config: bool = True,
@@ -879,7 +877,7 @@ class RootConfig:
         )
 
     def generate_missing_files(
-        self, config_dict: Dict[str, Any], config_dir_path: str
+        self, config_dict: dict[str, Any], config_dir_path: str
     ) -> None:
         self.invoke_all("generate_files", config_dict, config_dir_path)
 
@@ -898,7 +896,7 @@ class RootConfig:
         :returns: the previous config object, which no longer has a reference to this
             RootConfig.
         """
-        existing_config: Optional[Config] = getattr(self, section_name, None)
+        existing_config: Config | None = getattr(self, section_name, None)
         if existing_config is None:
             raise ValueError(f"Unknown config section '{section_name}'")
         logger.info("Reloading config section '%s'", section_name)
@@ -911,8 +909,22 @@ class RootConfig:
         existing_config.root = None
         return existing_config
 
+    def validate_config(self) -> None:
+        """
+        Additional config validation across all config sections.
 
-def read_config_files(config_files: Iterable[str]) -> Dict[str, Any]:
+        Override this in subclasses to add extra validation. This is called once all
+        config option values have been populated.
+
+        XXX: This should only validate, not modify the configuration, as the final
+        config state is required for proper validation across all config sections.
+
+        Raises:
+            ConfigError: if the config is invalid.
+        """
+
+
+def read_config_files(config_files: Iterable[str]) -> dict[str, Any]:
     """Read the config files and shallowly merge them into a dict.
 
     Successive configurations are shallowly merged into ones provided earlier,
@@ -946,7 +958,7 @@ def read_config_files(config_files: Iterable[str]) -> Dict[str, Any]:
     return specified_config
 
 
-def find_config_files(search_paths: List[str]) -> List[str]:
+def find_config_files(search_paths: list[str]) -> list[str]:
     """Finds config files using a list of search paths. If a path is a file
     then that file path is added to the list. If a search path is a directory
     then all the "*.yaml" files in that directory are added to the list in
@@ -1000,7 +1012,7 @@ class ShardedWorkerHandlingConfig:
     below).
     """
 
-    instances: List[str]
+    instances: list[str]
 
     def should_handle(self, instance_name: str, key: str) -> bool:
         """Whether this instance is responsible for handling the given key."""
diff --git a/synapse/config/_base.pyi b/synapse/config/_base.pyi
index 5e03635206..fe9b3333c4 100644
--- a/synapse/config/_base.pyi
+++ b/synapse/config/_base.pyi
@@ -2,17 +2,11 @@ import argparse
 from typing import (
     Any,
     Collection,
-    Dict,
     Iterable,
     Iterator,
-    List,
     Literal,
     MutableMapping,
-    Optional,
-    Tuple,
-    Type,
     TypeVar,
-    Union,
     overload,
 )
 
@@ -37,6 +31,7 @@ from synapse.config import (  # noqa: F401
     key,
     logger,
     mas,
+    matrixrtc,
     metrics,
     modules,
     oembed,
@@ -67,7 +62,7 @@ from synapse.config import (  # noqa: F401
 from synapse.types import StrSequence
 
 class ConfigError(Exception):
-    def __init__(self, msg: str, path: Optional[StrSequence] = None):
+    def __init__(self, msg: str, path: StrSequence | None = None):
         self.msg = msg
         self.path = path
 
@@ -126,9 +121,10 @@ class RootConfig:
     auto_accept_invites: auto_accept_invites.AutoAcceptInvitesConfig
     user_types: user_types.UserTypesConfig
     mas: mas.MasConfig
+    matrix_rtc: matrixrtc.MatrixRtcConfig
 
-    config_classes: List[Type["Config"]] = ...
-    config_files: List[str]
+    config_classes: list[type["Config"]] = ...
+    config_files: list[str]
     def __init__(self, config_files: Collection[str] = ...) -> None: ...
     def invoke_all(
         self, func_name: str, *args: Any, **kwargs: Any
@@ -137,7 +133,7 @@ class RootConfig:
     def invoke_all_static(cls, func_name: str, *args: Any, **kwargs: Any) -> None: ...
     def parse_config_dict(
         self,
-        config_dict: Dict[str, Any],
+        config_dict: dict[str, Any],
         config_dir_path: str,
         data_dir_path: str,
         allow_secrets_in_config: bool = ...,
@@ -148,19 +144,19 @@ class RootConfig:
         data_dir_path: str,
         server_name: str,
         generate_secrets: bool = ...,
-        report_stats: Optional[bool] = ...,
+        report_stats: bool | None = ...,
         open_private_ports: bool = ...,
-        listeners: Optional[Any] = ...,
-        tls_certificate_path: Optional[str] = ...,
-        tls_private_key_path: Optional[str] = ...,
+        listeners: Any | None = ...,
+        tls_certificate_path: str | None = ...,
+        tls_private_key_path: str | None = ...,
     ) -> str: ...
     @classmethod
     def load_or_generate_config(
-        cls: Type[TRootConfig], description: str, argv: List[str]
-    ) -> Optional[TRootConfig]: ...
+        cls: type[TRootConfig], description: str, argv_options: list[str]
+    ) -> TRootConfig | None: ...
     @classmethod
     def load_config(
-        cls: Type[TRootConfig], description: str, argv: List[str]
+        cls: type[TRootConfig], description: str, argv_options: list[str]
     ) -> TRootConfig: ...
     @classmethod
     def add_arguments_to_parser(
@@ -168,8 +164,8 @@ class RootConfig:
     ) -> None: ...
     @classmethod
     def load_config_with_parser(
-        cls: Type[TRootConfig], parser: argparse.ArgumentParser, argv: List[str]
-    ) -> Tuple[TRootConfig, argparse.Namespace]: ...
+        cls: type[TRootConfig], parser: argparse.ArgumentParser, argv_options: list[str]
+    ) -> tuple[TRootConfig, argparse.Namespace]: ...
     def generate_missing_files(
         self, config_dict: dict, config_dir_path: str
     ) -> None: ...
@@ -185,11 +181,11 @@ class Config:
     default_template_dir: str
     def __init__(self, root_config: RootConfig = ...) -> None: ...
     @staticmethod
-    def parse_size(value: Union[str, int]) -> int: ...
+    def parse_size(value: str | int) -> int: ...
     @staticmethod
-    def parse_duration(value: Union[str, int]) -> int: ...
+    def parse_duration(value: str | int) -> int: ...
     @staticmethod
-    def abspath(file_path: Optional[str]) -> str: ...
+    def abspath(file_path: str | None) -> str: ...
     @classmethod
     def path_exists(cls, file_path: str) -> bool: ...
     @classmethod
@@ -201,16 +197,16 @@ class Config:
     def read_template(self, filenames: str) -> jinja2.Template: ...
     def read_templates(
         self,
-        filenames: List[str],
-        custom_template_directories: Optional[Iterable[str]] = None,
-    ) -> List[jinja2.Template]: ...
+        filenames: list[str],
+        custom_template_directories: Iterable[str] | None = None,
+    ) -> list[jinja2.Template]: ...
 
-def read_config_files(config_files: Iterable[str]) -> Dict[str, Any]: ...
-def find_config_files(search_paths: List[str]) -> List[str]: ...
+def read_config_files(config_files: Iterable[str]) -> dict[str, Any]: ...
+def find_config_files(search_paths: list[str]) -> list[str]: ...
 
 class ShardedWorkerHandlingConfig:
-    instances: List[str]
-    def __init__(self, instances: List[str]) -> None: ...
+    instances: list[str]
+    def __init__(self, instances: list[str]) -> None: ...
     def should_handle(self, instance_name: str, key: str) -> bool: ...  # noqa: F811
 
 class RoutableShardedWorkerHandlingConfig(ShardedWorkerHandlingConfig):
diff --git a/synapse/config/_util.py b/synapse/config/_util.py
index 731b60a840..e09c68ebd4 100644
--- a/synapse/config/_util.py
+++ b/synapse/config/_util.py
@@ -18,11 +18,11 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Any, Dict, Type, TypeVar
+from typing import Any, TypeVar
 
 import jsonschema
+from pydantic import BaseModel, TypeAdapter, ValidationError
 
-from synapse._pydantic_compat import BaseModel, ValidationError, parse_obj_as
 from synapse.config._base import ConfigError
 from synapse.types import JsonDict, StrSequence
 
@@ -79,8 +79,8 @@ Model = TypeVar("Model", bound=BaseModel)
 
 def parse_and_validate_mapping(
     config: Any,
-    model_type: Type[Model],
-) -> Dict[str, Model]:
+    model_type: type[Model],
+) -> dict[str, Model]:
     """Parse `config` as a mapping from strings to a given `Model` type.
     Args:
         config: The configuration data to check
@@ -93,7 +93,7 @@ def parse_and_validate_mapping(
     try:
         # type-ignore: mypy doesn't like constructing `Dict[str, model_type]` because
         # `model_type` is a runtime variable. Pydantic is fine with this.
-        instances = parse_obj_as(Dict[str, model_type], config)  # type: ignore[valid-type]
+        instances = TypeAdapter(dict[str, model_type]).validate_python(config)  # type: ignore[valid-type]
     except ValidationError as e:
         raise ConfigError(str(e)) from e
     return instances
diff --git a/synapse/config/api.py b/synapse/config/api.py
index 0bb99d4228..03b92249a9 100644
--- a/synapse/config/api.py
+++ b/synapse/config/api.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import Any, Iterable, Optional, Tuple
+from typing import Any, Iterable
 
 from synapse.api.constants import EventTypes
 from synapse.config._base import Config, ConfigError
@@ -46,7 +46,7 @@ class ApiConfig(Config):
 
     def _get_prejoin_state_entries(
         self, config: JsonDict
-    ) -> Iterable[Tuple[str, Optional[str]]]:
+    ) -> Iterable[tuple[str, str | None]]:
         """Get the event types and state keys to include in the prejoin state."""
         room_prejoin_state_config = config.get("room_prejoin_state") or {}
 
diff --git a/synapse/config/appservice.py b/synapse/config/appservice.py
index 81dbd330cc..b9ed1a702c 100644
--- a/synapse/config/appservice.py
+++ b/synapse/config/appservice.py
@@ -21,7 +21,7 @@
 #
 
 import logging
-from typing import Any, Dict, List
+from typing import Any
 from urllib import parse as urlparse
 
 import yaml
@@ -61,13 +61,13 @@ class AppServiceConfig(Config):
 
 
 def load_appservices(
-    hostname: str, config_files: List[str]
-) -> List[ApplicationService]:
+    hostname: str, config_files: list[str]
+) -> list[ApplicationService]:
     """Returns a list of Application Services from the config files."""
 
     # Dicts of value -> filename
-    seen_as_tokens: Dict[str, str] = {}
-    seen_ids: Dict[str, str] = {}
+    seen_as_tokens: dict[str, str] = {}
+    seen_ids: dict[str, str] = {}
 
     appservices = []
 
diff --git a/synapse/config/cache.py b/synapse/config/cache.py
index 35a052b254..c9ce826e1a 100644
--- a/synapse/config/cache.py
+++ b/synapse/config/cache.py
@@ -23,7 +23,7 @@ import logging
 import os
 import re
 import threading
-from typing import Any, Callable, Dict, Mapping, Optional
+from typing import Any, Callable, Mapping
 
 import attr
 
@@ -38,7 +38,7 @@ logger = logging.getLogger(__name__)
 _CACHE_PREFIX = "SYNAPSE_CACHE_FACTOR"
 
 # Map from canonicalised cache name to cache.
-_CACHES: Dict[str, Callable[[float], None]] = {}
+_CACHES: dict[str, Callable[[float], None]] = {}
 
 # a lock on the contents of _CACHES
 _CACHES_LOCK = threading.Lock()
@@ -53,7 +53,7 @@ class CacheProperties:
     default_factor_size: float = float(
         os.environ.get(_CACHE_PREFIX, _DEFAULT_FACTOR_SIZE)
     )
-    resize_all_caches_func: Optional[Callable[[], None]] = None
+    resize_all_caches_func: Callable[[], None] | None = None
 
 
 properties = CacheProperties()
@@ -104,10 +104,10 @@ class CacheConfig(Config):
     _environ: Mapping[str, str] = os.environ
 
     event_cache_size: int
-    cache_factors: Dict[str, float]
+    cache_factors: dict[str, float]
     global_factor: float
     track_memory_usage: bool
-    expiry_time_msec: Optional[int]
+    expiry_time_msec: int | None
     sync_response_cache_duration: int
 
     @staticmethod
diff --git a/synapse/config/cas.py b/synapse/config/cas.py
index 60d66d7019..dc5be7ccf1 100644
--- a/synapse/config/cas.py
+++ b/synapse/config/cas.py
@@ -20,7 +20,7 @@
 #
 #
 
-from typing import Any, List, Optional
+from typing import Any
 
 from synapse.config.sso import SsoAttributeRequirement
 from synapse.types import JsonDict
@@ -49,7 +49,7 @@ class CasConfig(Config):
 
             # TODO Update this to a _synapse URL.
             public_baseurl = self.root.server.public_baseurl
-            self.cas_service_url: Optional[str] = (
+            self.cas_service_url: str | None = (
                 public_baseurl + "_matrix/client/r0/login/cas/ticket"
             )
 
@@ -107,7 +107,7 @@ REQUIRED_ATTRIBUTES_SCHEMA = {
 
 def _parsed_required_attributes_def(
     required_attributes: Any,
-) -> List[SsoAttributeRequirement]:
+) -> list[SsoAttributeRequirement]:
     validate_config(
         REQUIRED_ATTRIBUTES_SCHEMA,
         required_attributes,
diff --git a/synapse/config/consent.py b/synapse/config/consent.py
index 7dc80d4cf8..35484ee033 100644
--- a/synapse/config/consent.py
+++ b/synapse/config/consent.py
@@ -19,7 +19,7 @@
 #
 
 from os import path
-from typing import Any, Optional
+from typing import Any
 
 from synapse.config import ConfigError
 from synapse.types import JsonDict
@@ -33,11 +33,11 @@ class ConsentConfig(Config):
     def __init__(self, *args: Any):
         super().__init__(*args)
 
-        self.user_consent_version: Optional[str] = None
-        self.user_consent_template_dir: Optional[str] = None
-        self.user_consent_server_notice_content: Optional[JsonDict] = None
+        self.user_consent_version: str | None = None
+        self.user_consent_template_dir: str | None = None
+        self.user_consent_server_notice_content: JsonDict | None = None
         self.user_consent_server_notice_to_guests = False
-        self.block_events_without_consent_error: Optional[str] = None
+        self.block_events_without_consent_error: str | None = None
         self.user_consent_at_registration = False
         self.user_consent_policy_name = "Privacy Policy"
 
diff --git a/synapse/config/database.py b/synapse/config/database.py
index c4ca63a1fa..8e9d253820 100644
--- a/synapse/config/database.py
+++ b/synapse/config/database.py
@@ -22,7 +22,7 @@
 import argparse
 import logging
 import os
-from typing import Any, List
+from typing import Any
 
 from synapse.config._base import Config, ConfigError
 from synapse.types import JsonDict
@@ -83,7 +83,7 @@ class DatabaseConfig(Config):
     def __init__(self, *args: Any):
         super().__init__(*args)
 
-        self.databases: List[DatabaseConnectionConfig] = []
+        self.databases: list[DatabaseConnectionConfig] = []
 
     def read_config(self, config: JsonDict, **kwargs: Any) -> None:
         # We *experimentally* support specifying multiple databases via the
diff --git a/synapse/config/experimental.py b/synapse/config/experimental.py
index 8546e2fc40..13f5e1fcd8 100644
--- a/synapse/config/experimental.py
+++ b/synapse/config/experimental.py
@@ -59,7 +59,7 @@ class ClientAuthMethod(enum.Enum):
     PRIVATE_KEY_JWT = "private_key_jwt"
 
 
-def _parse_jwks(jwks: Optional[JsonDict]) -> Optional["JsonWebKey"]:
+def _parse_jwks(jwks: JsonDict | None) -> Optional["JsonWebKey"]:
     """A helper function to parse a JWK dict into a JsonWebKey."""
 
     if jwks is None:
@@ -71,7 +71,7 @@ def _parse_jwks(jwks: Optional[JsonDict]) -> Optional["JsonWebKey"]:
 
 
 def _check_client_secret(
-    instance: "MSC3861", _attribute: attr.Attribute, _value: Optional[str]
+    instance: "MSC3861", _attribute: attr.Attribute, _value: str | None
 ) -> None:
     if instance._client_secret and instance._client_secret_path:
         raise ConfigError(
@@ -88,7 +88,7 @@ def _check_client_secret(
 
 
 def _check_admin_token(
-    instance: "MSC3861", _attribute: attr.Attribute, _value: Optional[str]
+    instance: "MSC3861", _attribute: attr.Attribute, _value: str | None
 ) -> None:
     if instance._admin_token and instance._admin_token_path:
         raise ConfigError(
@@ -124,7 +124,7 @@ class MSC3861:
     issuer: str = attr.ib(default="", validator=attr.validators.instance_of(str))
     """The URL of the OIDC Provider."""
 
-    issuer_metadata: Optional[JsonDict] = attr.ib(default=None)
+    issuer_metadata: JsonDict | None = attr.ib(default=None)
     """The issuer metadata to use, otherwise discovered from /.well-known/openid-configuration as per MSC2965."""
 
     client_id: str = attr.ib(
@@ -138,7 +138,7 @@ class MSC3861:
     )
     """The auth method used when calling the introspection endpoint."""
 
-    _client_secret: Optional[str] = attr.ib(
+    _client_secret: str | None = attr.ib(
         default=None,
         validator=[
             attr.validators.optional(attr.validators.instance_of(str)),
@@ -150,7 +150,7 @@ class MSC3861:
     when using any of the client_secret_* client auth methods.
     """
 
-    _client_secret_path: Optional[str] = attr.ib(
+    _client_secret_path: str | None = attr.ib(
         default=None,
         validator=[
             attr.validators.optional(attr.validators.instance_of(str)),
@@ -196,19 +196,19 @@ class MSC3861:
                 ("experimental", "msc3861", "client_auth_method"),
             )
 
-    introspection_endpoint: Optional[str] = attr.ib(
+    introspection_endpoint: str | None = attr.ib(
         default=None,
         validator=attr.validators.optional(attr.validators.instance_of(str)),
     )
     """The URL of the introspection endpoint used to validate access tokens."""
 
-    account_management_url: Optional[str] = attr.ib(
+    account_management_url: str | None = attr.ib(
         default=None,
         validator=attr.validators.optional(attr.validators.instance_of(str)),
     )
     """The URL of the My Account page on the OIDC Provider as per MSC2965."""
 
-    _admin_token: Optional[str] = attr.ib(
+    _admin_token: str | None = attr.ib(
         default=None,
         validator=[
             attr.validators.optional(attr.validators.instance_of(str)),
@@ -220,7 +220,7 @@ class MSC3861:
     This is used by the OIDC provider, to make admin calls to Synapse.
     """
 
-    _admin_token_path: Optional[str] = attr.ib(
+    _admin_token_path: str | None = attr.ib(
         default=None,
         validator=[
             attr.validators.optional(attr.validators.instance_of(str)),
@@ -232,7 +232,7 @@ class MSC3861:
     external file.
     """
 
-    def client_secret(self) -> Optional[str]:
+    def client_secret(self) -> str | None:
         """Returns the secret given via `client_secret` or `client_secret_path`."""
         if self._client_secret_path:
             return read_secret_from_file_once(
@@ -241,7 +241,7 @@ class MSC3861:
             )
         return self._client_secret
 
-    def admin_token(self) -> Optional[str]:
+    def admin_token(self) -> str | None:
         """Returns the admin token given via `admin_token` or `admin_token_path`."""
         if self._admin_token_path:
             return read_secret_from_file_once(
@@ -412,11 +412,6 @@ class ExperimentalConfig(Config):
             "msc2409_to_device_messages_enabled", False
         )
 
-        # The portion of MSC3202 which is related to device masquerading.
-        self.msc3202_device_masquerading_enabled: bool = experimental.get(
-            "msc3202_device_masquerading", False
-        )
-
         # The portion of MSC3202 related to transaction extensions:
         # sending device list changes, one-time key counts and fallback key
         # usage to application services.
@@ -531,7 +526,7 @@ class ExperimentalConfig(Config):
         # MSC4108: Mechanism to allow OIDC sign in and E2EE set up via QR code
         self.msc4108_enabled = experimental.get("msc4108_enabled", False)
 
-        self.msc4108_delegation_endpoint: Optional[str] = experimental.get(
+        self.msc4108_delegation_endpoint: str | None = experimental.get(
             "msc4108_delegation_endpoint", None
         )
 
@@ -556,6 +551,9 @@ class ExperimentalConfig(Config):
         # MSC4133: Custom profile fields
         self.msc4133_enabled: bool = experimental.get("msc4133_enabled", False)
 
+        # MSC4143: Matrix RTC Transport using Livekit Backend
+        self.msc4143_enabled: bool = experimental.get("msc4143_enabled", False)
+
         # MSC4169: Backwards-compatible redaction sending using `/send`
         self.msc4169_enabled: bool = experimental.get("msc4169_enabled", False)
 
diff --git a/synapse/config/federation.py b/synapse/config/federation.py
index 31f46e420d..ad0bd56a80 100644
--- a/synapse/config/federation.py
+++ b/synapse/config/federation.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Any, Optional
+from typing import Any
 
 from synapse.config._base import Config
 from synapse.config._util import validate_config
@@ -32,7 +32,7 @@ class FederationConfig(Config):
         federation_config = config.setdefault("federation", {})
 
         # FIXME: federation_domain_whitelist needs sytests
-        self.federation_domain_whitelist: Optional[dict] = None
+        self.federation_domain_whitelist: dict | None = None
         federation_domain_whitelist = config.get("federation_domain_whitelist", None)
 
         if federation_domain_whitelist is not None:
diff --git a/synapse/config/homeserver.py b/synapse/config/homeserver.py
index 5d7089c2e6..94ebe583a4 100644
--- a/synapse/config/homeserver.py
+++ b/synapse/config/homeserver.py
@@ -18,7 +18,8 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from ._base import RootConfig
+
+from ._base import ConfigError, RootConfig
 from .account_validity import AccountValidityConfig
 from .api import ApiConfig
 from .appservice import AppServiceConfig
@@ -37,6 +38,7 @@ from .jwt import JWTConfig
 from .key import KeyConfig
 from .logger import LoggingConfig
 from .mas import MasConfig
+from .matrixrtc import MatrixRtcConfig
 from .metrics import MetricsConfig
 from .modules import ModulesConfig
 from .oembed import OembedConfig
@@ -66,6 +68,10 @@ from .workers import WorkerConfig
 
 
 class HomeServerConfig(RootConfig):
+    """
+    Top-level config object for Synapse homeserver (main process and workers).
+    """
+
     config_classes = [
         ModulesConfig,
         ServerConfig,
@@ -80,6 +86,7 @@ class HomeServerConfig(RootConfig):
         OembedConfig,
         CaptchaConfig,
         VoipConfig,
+        MatrixRtcConfig,
         RegistrationConfig,
         AccountValidityConfig,
         MetricsConfig,
@@ -113,3 +120,22 @@ class HomeServerConfig(RootConfig):
         # This must be last, as it checks for conflicts with other config options.
         MasConfig,
     ]
+
+    def validate_config(
+        self,
+    ) -> None:
+        if (
+            self.registration.enable_registration
+            and not self.registration.enable_registration_without_verification
+        ):
+            if (
+                not self.captcha.enable_registration_captcha
+                and not self.registration.registrations_require_3pid
+                and not self.registration.registration_requires_token
+            ):
+                raise ConfigError(
+                    "You have enabled open registration without any verification. This is a known vector for "
+                    "spam and abuse. If you would like to allow public registration, please consider adding email, "
+                    "captcha, or token-based verification. Otherwise this check can be removed by setting the "
+                    "`enable_registration_without_verification` config option to `true`."
+                )
diff --git a/synapse/config/key.py b/synapse/config/key.py
index f78ff5114f..bfeeac5e30 100644
--- a/synapse/config/key.py
+++ b/synapse/config/key.py
@@ -23,7 +23,7 @@
 import hashlib
 import logging
 import os
-from typing import TYPE_CHECKING, Any, Dict, Iterator, List, Optional
+from typing import TYPE_CHECKING, Any, Iterator
 
 import attr
 import jsonschema
@@ -110,7 +110,7 @@ class TrustedKeyServer:
     server_name: str
 
     # map from key id to key object, or None to disable signature verification.
-    verify_keys: Optional[Dict[str, VerifyKey]] = None
+    verify_keys: dict[str, VerifyKey] | None = None
 
 
 class KeyConfig(Config):
@@ -219,7 +219,7 @@ class KeyConfig(Config):
         if form_secret_path:
             if form_secret:
                 raise ConfigError(CONFLICTING_FORM_SECRET_OPTS_ERROR)
-            self.form_secret: Optional[str] = read_file(
+            self.form_secret: str | None = read_file(
                 form_secret_path, ("form_secret_path",)
             ).strip()
         else:
@@ -250,7 +250,7 @@ class KeyConfig(Config):
           - server_name: "matrix.org"
         """ % locals()
 
-    def read_signing_keys(self, signing_key_path: str, name: str) -> List[SigningKey]:
+    def read_signing_keys(self, signing_key_path: str, name: str) -> list[SigningKey]:
         """Read the signing keys in the given path.
 
         Args:
@@ -279,8 +279,8 @@ class KeyConfig(Config):
             raise ConfigError("Error reading %s: %s" % (name, str(e)))
 
     def read_old_signing_keys(
-        self, old_signing_keys: Optional[JsonDict]
-    ) -> Dict[str, "VerifyKeyWithExpiry"]:
+        self, old_signing_keys: JsonDict | None
+    ) -> dict[str, "VerifyKeyWithExpiry"]:
         if old_signing_keys is None:
             return {}
         keys = {}
@@ -299,7 +299,7 @@ class KeyConfig(Config):
                 )
         return keys
 
-    def generate_files(self, config: Dict[str, Any], config_dir_path: str) -> None:
+    def generate_files(self, config: dict[str, Any], config_dir_path: str) -> None:
         if "signing_key" in config:
             return
 
@@ -393,7 +393,7 @@ TRUSTED_KEY_SERVERS_SCHEMA = {
 
 
 def _parse_key_servers(
-    key_servers: List[Any], federation_verify_certificates: bool
+    key_servers: list[Any], federation_verify_certificates: bool
 ) -> Iterator[TrustedKeyServer]:
     try:
         jsonschema.validate(key_servers, TRUSTED_KEY_SERVERS_SCHEMA)
@@ -408,7 +408,7 @@ def _parse_key_servers(
         server_name = server["server_name"]
         result = TrustedKeyServer(server_name=server_name)
 
-        verify_keys: Optional[Dict[str, str]] = server.get("verify_keys")
+        verify_keys: dict[str, str] | None = server.get("verify_keys")
         if verify_keys is not None:
             result.verify_keys = {}
             for key_id, key_base64 in verify_keys.items():
diff --git a/synapse/config/logger.py b/synapse/config/logger.py
index 0531ae7875..4af73627be 100644
--- a/synapse/config/logger.py
+++ b/synapse/config/logger.py
@@ -26,7 +26,7 @@ import os
 import sys
 import threading
 from string import Template
-from typing import TYPE_CHECKING, Any, Dict, Optional
+from typing import TYPE_CHECKING, Any
 
 import yaml
 from zope.interface import implementer
@@ -186,7 +186,7 @@ class LoggingConfig(Config):
             help=argparse.SUPPRESS,
         )
 
-    def generate_files(self, config: Dict[str, Any], config_dir_path: str) -> None:
+    def generate_files(self, config: dict[str, Any], config_dir_path: str) -> None:
         log_config = config.get("log_config")
         if log_config and not os.path.exists(log_config):
             log_file = self.abspath("homeserver.log")
@@ -198,12 +198,27 @@ class LoggingConfig(Config):
                 log_config_file.write(DEFAULT_LOG_CONFIG.substitute(log_file=log_file))
 
 
-def _setup_stdlib_logging(
-    config: "HomeServerConfig", log_config_path: Optional[str], logBeginner: LogBeginner
-) -> None:
+_already_performed_one_time_logging_setup: bool = False
+"""
+Marks whether we've already successfully ran `one_time_logging_setup()`.
+"""
+
+
+def one_time_logging_setup(*, logBeginner: LogBeginner = globalLogBeginner) -> None:
     """
-    Set up Python standard library logging.
+    Perform one-time logging configuration for the Python process.
+
+    For example, we don't need to have multiple log record factories. Once we've
+    configured it once, we don't need to do it again.
+
+    This matters because multiple Synapse instances can be run in the same Python
+    process (c.f. Synapse Pro for small hosts)
     """
+    global _already_performed_one_time_logging_setup
+
+    # We only need to set things up once.
+    if _already_performed_one_time_logging_setup:
+        return
 
     # We add a log record factory that runs all messages through the
     # LoggingContextFilter so that we get the context *at the time we log*
@@ -221,26 +236,6 @@ def _setup_stdlib_logging(
 
     logging.setLogRecordFactory(factory)
 
-    # Configure the logger with the initial configuration.
-    if log_config_path is None:
-        log_format = (
-            "%(asctime)s - %(name)s - %(lineno)d - %(levelname)s - %(request)s"
-            " - %(message)s"
-        )
-
-        logger = logging.getLogger("")
-        logger.setLevel(logging.INFO)
-        logging.getLogger("synapse.storage.SQL").setLevel(logging.INFO)
-
-        formatter = logging.Formatter(log_format)
-
-        handler = logging.StreamHandler()
-        handler.setFormatter(formatter)
-        logger.addHandler(handler)
-    else:
-        # Load the logging configuration.
-        _load_logging_config(log_config_path)
-
     # Route Twisted's native logging through to the standard library logging
     # system.
     observer = STDLibLogObserver()
@@ -281,6 +276,36 @@ def _setup_stdlib_logging(
 
     logBeginner.beginLoggingTo([_log], redirectStandardIO=False)
 
+    _already_performed_one_time_logging_setup = True
+
+
+def _setup_stdlib_logging(
+    config: "HomeServerConfig", log_config_path: str | None
+) -> None:
+    """
+    Set up Python standard library logging.
+    """
+
+    # Configure the logger with the initial configuration.
+    if log_config_path is None:
+        log_format = (
+            "%(asctime)s - %(name)s - %(lineno)d - %(levelname)s - %(request)s"
+            " - %(message)s"
+        )
+
+        logger = logging.getLogger("")
+        logger.setLevel(logging.INFO)
+        logging.getLogger("synapse.storage.SQL").setLevel(logging.INFO)
+
+        formatter = logging.Formatter(log_format)
+
+        handler = logging.StreamHandler()
+        handler.setFormatter(formatter)
+        logger.addHandler(handler)
+    else:
+        # Load the logging configuration.
+        _load_logging_config(log_config_path)
+
 
 def _load_logging_config(log_config_path: str) -> None:
     """
@@ -302,7 +327,7 @@ def _load_logging_config(log_config_path: str) -> None:
     reset_logging_config()
 
 
-def _reload_logging_config(log_config_path: Optional[str]) -> None:
+def _reload_logging_config(log_config_path: str | None) -> None:
     """
     Reload the log configuration from the file and apply it.
     """
@@ -318,19 +343,14 @@ def setup_logging(
     hs: "HomeServer",
     config: "HomeServerConfig",
     use_worker_options: bool = False,
-    logBeginner: LogBeginner = globalLogBeginner,
 ) -> None:
     """
     Set up the logging subsystem.
 
     Args:
         config: configuration data
-
         use_worker_options: True to use the 'worker_log_config' option
             instead of 'log_config'.
-
-        logBeginner: The Twisted logBeginner to use.
-
     """
     from twisted.internet import reactor
 
@@ -341,11 +361,17 @@ def setup_logging(
     )
 
     # Perform one-time logging configuration.
-    _setup_stdlib_logging(config, log_config_path, logBeginner=logBeginner)
+    one_time_logging_setup()
+
+    # Configure logging.
+    _setup_stdlib_logging(config, log_config_path)
     # Add a SIGHUP handler to reload the logging configuration, if one is available.
     from synapse.app import _base as appbase
 
-    appbase.register_sighup(_reload_logging_config, log_config_path)
+    # We only need to reload the config if there is a log config file path provided to
+    # reload from.
+    if log_config_path:
+        appbase.register_sighup(hs, _reload_logging_config, log_config_path)
 
     # Log immediately so we can grep backwards.
     logger.warning("***** STARTING SERVER *****")
diff --git a/synapse/config/mas.py b/synapse/config/mas.py
index fe0d326f7a..104ba17ab7 100644
--- a/synapse/config/mas.py
+++ b/synapse/config/mas.py
@@ -13,17 +13,19 @@
 #
 #
 
-from typing import Any, Optional
+from typing import Any
 
-from synapse._pydantic_compat import (
+from pydantic import (
     AnyHttpUrl,
     Field,
     FilePath,
     StrictBool,
     StrictStr,
     ValidationError,
-    validator,
+    model_validator,
 )
+from typing_extensions import Self
+
 from synapse.config.experimental import read_secret_from_file_once
 from synapse.types import JsonDict
 from synapse.util.pydantic_models import ParseModel
@@ -33,27 +35,25 @@ from ._base import Config, ConfigError, RootConfig
 
 class MasConfigModel(ParseModel):
     enabled: StrictBool = False
-    endpoint: AnyHttpUrl = Field(default="http://localhost:8080")
-    secret: Optional[StrictStr] = Field(default=None)
-    secret_path: Optional[FilePath] = Field(default=None)
+    endpoint: AnyHttpUrl = AnyHttpUrl("http://localhost:8080")
+    secret: StrictStr | None = Field(default=None)
+    # We set `strict=False` to allow `str` instances.
+    secret_path: FilePath | None = Field(default=None, strict=False)
 
-    @validator("secret")
-    def validate_secret_is_set_if_enabled(cls, v: Any, values: dict) -> Any:
-        if values.get("enabled", False) and not values.get("secret_path") and not v:
+    @model_validator(mode="after")
+    def verify_secret(self) -> Self:
+        if not self.enabled:
+            return self
+        if not self.secret and not self.secret_path:
             raise ValueError(
-                "You must set a `secret` or `secret_path` when enabling Matrix Authentication Service integration."
+                "You must set a `secret` or `secret_path` when enabling the Matrix "
+                "Authentication Service integration."
             )
-
-        return v
-
-    @validator("secret_path")
-    def validate_secret_path_is_set_if_enabled(cls, v: Any, values: dict) -> Any:
-        if values.get("secret"):
+        if self.secret and self.secret_path:
             raise ValueError(
                 "`secret` and `secret_path` cannot be set at the same time."
             )
-
-        return v
+        return self
 
 
 class MasConfig(Config):
diff --git a/synapse/config/matrixrtc.py b/synapse/config/matrixrtc.py
new file mode 100644
index 0000000000..84c245e286
--- /dev/null
+++ b/synapse/config/matrixrtc.py
@@ -0,0 +1,66 @@
+#
+# This file is licensed under the Affero General Public License (AGPL) version 3.
+#
+# Copyright (C) 2025 New Vector, Ltd
+#
+# This program is free software: you can redistribute it and/or modify
+# it under the terms of the GNU Affero General Public License as
+# published by the Free Software Foundation, either version 3 of the
+# License, or (at your option) any later version.
+#
+# See the GNU Affero General Public License for more details:
+# <https://www.gnu.org/licenses/agpl-3.0.html>.
+#
+# [This file includes modifications made by New Vector Limited]
+#
+#
+
+from typing import Any
+
+from pydantic import Field, StrictStr, ValidationError, model_validator
+from typing_extensions import Self
+
+from synapse.types import JsonDict
+from synapse.util.pydantic_models import ParseModel
+
+from ._base import Config, ConfigError
+
+
+class TransportConfigModel(ParseModel):
+    type: StrictStr
+
+    livekit_service_url: StrictStr | None = Field(default=None)
+    """An optional livekit service URL. Only required if type is "livekit"."""
+
+    @model_validator(mode="after")
+    def validate_livekit_service_url(self) -> Self:
+        if self.type == "livekit" and not self.livekit_service_url:
+            raise ValueError(
+                "You must set a `livekit_service_url` when using the 'livekit' transport."
+            )
+        return self
+
+
+class MatrixRtcConfigModel(ParseModel):
+    transports: list = []
+
+
+class MatrixRtcConfig(Config):
+    section = "matrix_rtc"
+
+    def read_config(
+        self, config: JsonDict, allow_secrets_in_config: bool, **kwargs: Any
+    ) -> None:
+        matrix_rtc = config.get("matrix_rtc", {})
+        if matrix_rtc is None:
+            matrix_rtc = {}
+
+        try:
+            parsed = MatrixRtcConfigModel(**matrix_rtc)
+        except ValidationError as e:
+            raise ConfigError(
+                "Could not validate matrix_rtc config",
+                ("matrix_rtc",),
+            ) from e
+
+        self.transports = parsed.transports
diff --git a/synapse/config/metrics.py b/synapse/config/metrics.py
index 8a4ded62ef..83dbee53b6 100644
--- a/synapse/config/metrics.py
+++ b/synapse/config/metrics.py
@@ -20,7 +20,7 @@
 #
 #
 
-from typing import Any, Optional
+from typing import Any
 
 import attr
 
@@ -75,7 +75,7 @@ class MetricsConfig(Config):
                 )
 
     def generate_config_section(
-        self, report_stats: Optional[bool] = None, **kwargs: Any
+        self, report_stats: bool | None = None, **kwargs: Any
     ) -> str:
         if report_stats is not None:
             res = "report_stats: %s\n" % ("true" if report_stats else "false")
diff --git a/synapse/config/modules.py b/synapse/config/modules.py
index 37dc26e130..17319c9e37 100644
--- a/synapse/config/modules.py
+++ b/synapse/config/modules.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Any, Dict, List, Tuple
+from typing import Any
 
 from synapse.config._base import Config, ConfigError
 from synapse.types import JsonDict
@@ -29,7 +29,7 @@ class ModulesConfig(Config):
     section = "modules"
 
     def read_config(self, config: JsonDict, **kwargs: Any) -> None:
-        self.loaded_modules: List[Tuple[Any, Dict]] = []
+        self.loaded_modules: list[tuple[Any, dict]] = []
 
         configured_modules = config.get("modules") or []
         for i, module in enumerate(configured_modules):
diff --git a/synapse/config/oembed.py b/synapse/config/oembed.py
index 1b6c521087..208f86374b 100644
--- a/synapse/config/oembed.py
+++ b/synapse/config/oembed.py
@@ -21,7 +21,7 @@
 import importlib.resources as importlib_resources
 import json
 import re
-from typing import Any, Dict, Iterable, List, Optional, Pattern
+from typing import Any, Iterable, Pattern
 from urllib import parse as urlparse
 
 import attr
@@ -37,9 +37,9 @@ class OEmbedEndpointConfig:
     # The API endpoint to fetch.
     api_endpoint: str
     # The patterns to match.
-    url_patterns: List[Pattern[str]]
+    url_patterns: list[Pattern[str]]
     # The supported formats.
-    formats: Optional[List[str]]
+    formats: list[str] | None
 
 
 class OembedConfig(Config):
@@ -48,10 +48,10 @@ class OembedConfig(Config):
     section = "oembed"
 
     def read_config(self, config: JsonDict, **kwargs: Any) -> None:
-        oembed_config: Dict[str, Any] = config.get("oembed") or {}
+        oembed_config: dict[str, Any] = config.get("oembed") or {}
 
         # A list of patterns which will be used.
-        self.oembed_patterns: List[OEmbedEndpointConfig] = list(
+        self.oembed_patterns: list[OEmbedEndpointConfig] = list(
             self._parse_and_validate_providers(oembed_config)
         )
 
@@ -92,7 +92,7 @@ class OembedConfig(Config):
             )
 
     def _parse_and_validate_provider(
-        self, providers: List[JsonDict], config_path: StrSequence
+        self, providers: list[JsonDict], config_path: StrSequence
     ) -> Iterable[OEmbedEndpointConfig]:
         # Ensure it is the proper form.
         validate_config(
diff --git a/synapse/config/oidc.py b/synapse/config/oidc.py
index 3ddf65a3e9..73fe6891cd 100644
--- a/synapse/config/oidc.py
+++ b/synapse/config/oidc.py
@@ -21,7 +21,7 @@
 #
 
 from collections import Counter
-from typing import Any, Collection, Iterable, List, Mapping, Optional, Tuple, Type
+from typing import Any, Collection, Iterable, Mapping
 
 import attr
 
@@ -213,7 +213,7 @@ def _parse_oidc_provider_configs(config: JsonDict) -> Iterable["OidcProviderConf
 
 
 def _parse_oidc_config_dict(
-    oidc_config: JsonDict, config_path: Tuple[str, ...]
+    oidc_config: JsonDict, config_path: tuple[str, ...]
 ) -> "OidcProviderConfig":
     """Take the configuration dict and parse it into an OidcProviderConfig
 
@@ -276,7 +276,7 @@ def _parse_oidc_config_dict(
             ) from e
 
     client_secret_jwt_key_config = oidc_config.get("client_secret_jwt_key")
-    client_secret_jwt_key: Optional[OidcProviderClientSecretJwtKey] = None
+    client_secret_jwt_key: OidcProviderClientSecretJwtKey | None = None
     if client_secret_jwt_key_config is not None:
         keyfile = client_secret_jwt_key_config.get("key_file")
         if keyfile:
@@ -384,10 +384,10 @@ class OidcProviderConfig:
     idp_name: str
 
     # Optional MXC URI for icon for this IdP.
-    idp_icon: Optional[str]
+    idp_icon: str | None
 
     # Optional brand identifier for this IdP.
-    idp_brand: Optional[str]
+    idp_brand: str | None
 
     # whether the OIDC discovery mechanism is used to discover endpoints
     discover: bool
@@ -401,11 +401,11 @@ class OidcProviderConfig:
 
     # oauth2 client secret to use. if `None`, use client_secret_jwt_key to generate
     # a secret.
-    client_secret: Optional[str]
+    client_secret: str | None
 
     # key to use to construct a JWT to use as a client secret. May be `None` if
     # `client_secret` is set.
-    client_secret_jwt_key: Optional[OidcProviderClientSecretJwtKey]
+    client_secret_jwt_key: OidcProviderClientSecretJwtKey | None
 
     # auth method to use when exchanging the token.
     # Valid values are 'client_secret_basic', 'client_secret_post' and
@@ -416,7 +416,7 @@ class OidcProviderConfig:
     # Valid values are 'auto', 'always', and 'never'.
     pkce_method: str
 
-    id_token_signing_alg_values_supported: Optional[List[str]]
+    id_token_signing_alg_values_supported: list[str] | None
     """
     List of the JWS signing algorithms (`alg` values) that are supported for signing the
     `id_token`.
@@ -448,18 +448,18 @@ class OidcProviderConfig:
     scopes: Collection[str]
 
     # the oauth2 authorization endpoint. Required if discovery is disabled.
-    authorization_endpoint: Optional[str]
+    authorization_endpoint: str | None
 
     # the oauth2 token endpoint. Required if discovery is disabled.
-    token_endpoint: Optional[str]
+    token_endpoint: str | None
 
     # the OIDC userinfo endpoint. Required if discovery is disabled and the
     # "openid" scope is not requested.
-    userinfo_endpoint: Optional[str]
+    userinfo_endpoint: str | None
 
     # URI where to fetch the JWKS. Required if discovery is disabled and the
     # "openid" scope is used.
-    jwks_uri: Optional[str]
+    jwks_uri: str | None
 
     # Whether Synapse should react to backchannel logouts
     backchannel_logout_enabled: bool
@@ -474,7 +474,7 @@ class OidcProviderConfig:
     # values are: "auto" or "userinfo_endpoint".
     user_profile_method: str
 
-    redirect_uri: Optional[str]
+    redirect_uri: str | None
     """
     An optional replacement for Synapse's hardcoded `redirect_uri` URL
     (`<public_baseurl>/_synapse/client/oidc/callback`). This can be used to send
@@ -491,13 +491,13 @@ class OidcProviderConfig:
     allow_existing_users: bool
 
     # the class of the user mapping provider
-    user_mapping_provider_class: Type
+    user_mapping_provider_class: type
 
     # the config of the user mapping provider
     user_mapping_provider_config: Any
 
     # required attributes to require in userinfo to allow login/registration
-    attribute_requirements: List[SsoAttributeRequirement]
+    attribute_requirements: list[SsoAttributeRequirement]
 
     # Whether automatic registrations are enabled in the ODIC flow. Defaults to True
     enable_registration: bool
diff --git a/synapse/config/password_auth_providers.py b/synapse/config/password_auth_providers.py
index b2b624aea2..c2894f58dc 100644
--- a/synapse/config/password_auth_providers.py
+++ b/synapse/config/password_auth_providers.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import Any, List, Tuple, Type
+from typing import Any
 
 from synapse.types import JsonDict
 from synapse.util.module_loader import load_module
@@ -56,7 +56,7 @@ class PasswordAuthProviderConfig(Config):
         for backwards compatibility.
         """
 
-        self.password_providers: List[Tuple[Type, Any]] = []
+        self.password_providers: list[tuple[type, Any]] = []
         providers = []
 
         # We want to be backwards compatible with the old `ldap_config`
diff --git a/synapse/config/ratelimiting.py b/synapse/config/ratelimiting.py
index b082daa8f7..78d9d61d3c 100644
--- a/synapse/config/ratelimiting.py
+++ b/synapse/config/ratelimiting.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import Any, Dict, Optional, cast
+from typing import Any, cast
 
 import attr
 
@@ -37,9 +37,9 @@ class RatelimitSettings:
     @classmethod
     def parse(
         cls,
-        config: Dict[str, Any],
+        config: dict[str, Any],
         key: str,
-        defaults: Optional[Dict[str, float]] = None,
+        defaults: dict[str, float] | None = None,
     ) -> "RatelimitSettings":
         """Parse config[key] as a new-style rate limiter config.
 
@@ -62,7 +62,7 @@ class RatelimitSettings:
 
         # By this point we should have hit the rate limiter parameters.
         # We don't actually check this though!
-        rl_config = cast(Dict[str, float], rl_config)
+        rl_config = cast(dict[str, float], rl_config)
 
         return cls(
             key=key,
diff --git a/synapse/config/registration.py b/synapse/config/registration.py
index 283199aa11..7f7a224e02 100644
--- a/synapse/config/registration.py
+++ b/synapse/config/registration.py
@@ -20,7 +20,7 @@
 #
 #
 import argparse
-from typing import Any, Dict, Optional
+from typing import Any
 
 from synapse.api.constants import RoomCreationPreset
 from synapse.config._base import Config, ConfigError, read_file
@@ -181,7 +181,7 @@ class RegistrationConfig(Config):
             refreshable_access_token_lifetime = self.parse_duration(
                 refreshable_access_token_lifetime
             )
-        self.refreshable_access_token_lifetime: Optional[int] = (
+        self.refreshable_access_token_lifetime: int | None = (
             refreshable_access_token_lifetime
         )
 
@@ -226,7 +226,7 @@ class RegistrationConfig(Config):
         refresh_token_lifetime = config.get("refresh_token_lifetime")
         if refresh_token_lifetime is not None:
             refresh_token_lifetime = self.parse_duration(refresh_token_lifetime)
-        self.refresh_token_lifetime: Optional[int] = refresh_token_lifetime
+        self.refresh_token_lifetime: int | None = refresh_token_lifetime
 
         if (
             self.session_lifetime is not None
@@ -266,7 +266,7 @@ class RegistrationConfig(Config):
         else:
             return ""
 
-    def generate_files(self, config: Dict[str, Any], config_dir_path: str) -> None:
+    def generate_files(self, config: dict[str, Any], config_dir_path: str) -> None:
         # if 'registration_shared_secret_path' is specified, and the target file
         # does not exist, generate it.
         registration_shared_secret_path = config.get("registration_shared_secret_path")
diff --git a/synapse/config/repository.py b/synapse/config/repository.py
index e7d23740f9..221130b0cd 100644
--- a/synapse/config/repository.py
+++ b/synapse/config/repository.py
@@ -21,7 +21,7 @@
 
 import logging
 import os
-from typing import Any, Dict, List, Tuple
+from typing import Any
 
 import attr
 
@@ -80,8 +80,8 @@ class MediaStorageProviderConfig:
 
 
 def parse_thumbnail_requirements(
-    thumbnail_sizes: List[JsonDict],
-) -> Dict[str, Tuple[ThumbnailRequirement, ...]]:
+    thumbnail_sizes: list[JsonDict],
+) -> dict[str, tuple[ThumbnailRequirement, ...]]:
     """Takes a list of dictionaries with "width", "height", and "method" keys
     and creates a map from image media types to the thumbnail size, thumbnailing
     method, and thumbnail media type to precalculate
@@ -92,7 +92,7 @@ def parse_thumbnail_requirements(
     Returns:
         Dictionary mapping from media type string to list of ThumbnailRequirement.
     """
-    requirements: Dict[str, List[ThumbnailRequirement]] = {}
+    requirements: dict[str, list[ThumbnailRequirement]] = {}
     for size in thumbnail_sizes:
         width = size["width"]
         height = size["height"]
@@ -206,7 +206,7 @@ class ContentRepositoryConfig(Config):
         #
         # We don't create the storage providers here as not all workers need
         # them to be started.
-        self.media_storage_providers: List[tuple] = []
+        self.media_storage_providers: list[tuple] = []
 
         for i, provider_config in enumerate(storage_providers):
             # We special case the module "file_system" so as not to need to
@@ -298,7 +298,7 @@ class ContentRepositoryConfig(Config):
 
         self.enable_authenticated_media = config.get("enable_authenticated_media", True)
 
-        self.media_upload_limits: List[MediaUploadLimit] = []
+        self.media_upload_limits: list[MediaUploadLimit] = []
         for limit_config in config.get("media_upload_limits", []):
             time_period_ms = self.parse_duration(limit_config["time_period"])
             max_bytes = self.parse_size(limit_config["max_size"])
diff --git a/synapse/config/retention.py b/synapse/config/retention.py
index 7e329c7f42..ab80ac214d 100644
--- a/synapse/config/retention.py
+++ b/synapse/config/retention.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import Any, List, Optional
+from typing import Any
 
 import attr
 
@@ -35,8 +35,8 @@ class RetentionPurgeJob:
     """Object describing the configuration of the manhole"""
 
     interval: int
-    shortest_max_lifetime: Optional[int]
-    longest_max_lifetime: Optional[int]
+    shortest_max_lifetime: int | None
+    longest_max_lifetime: int | None
 
 
 class RetentionConfig(Config):
@@ -119,7 +119,7 @@ class RetentionConfig(Config):
                 " greater than 'allowed_lifetime_max'"
             )
 
-        self.retention_purge_jobs: List[RetentionPurgeJob] = []
+        self.retention_purge_jobs: list[RetentionPurgeJob] = []
         for purge_job_config in retention_config.get("purge_jobs", []):
             interval_config = purge_job_config.get("interval")
 
diff --git a/synapse/config/saml2.py b/synapse/config/saml2.py
index 9d7ef94507..acba63ee9b 100644
--- a/synapse/config/saml2.py
+++ b/synapse/config/saml2.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import Any, List, Set
+from typing import Any
 
 from synapse.config.sso import SsoAttributeRequirement
 from synapse.types import JsonDict
@@ -160,8 +160,11 @@ class SAML2Config(Config):
             )
 
         # Get the desired saml auth response attributes from the module
+        # type-ignore: the provider class was already checked for having the method being called
+        # with the runtime checks above, which mypy is not aware of, and treats as an error
+        # ever since the typehint of provider class was changed from "typing.Type" to "type"
         saml2_config_dict = self._default_saml_config_dict(
-            *self.saml2_user_mapping_provider_class.get_saml_attributes(
+            *self.saml2_user_mapping_provider_class.get_saml_attributes(  # type: ignore[attr-defined]
                 self.saml2_user_mapping_provider_config
             )
         )
@@ -191,7 +194,7 @@ class SAML2Config(Config):
         )
 
     def _default_saml_config_dict(
-        self, required_attributes: Set[str], optional_attributes: Set[str]
+        self, required_attributes: set[str], optional_attributes: set[str]
     ) -> JsonDict:
         """Generate a configuration dictionary with required and optional attributes that
         will be needed to process new user registration
@@ -239,7 +242,7 @@ ATTRIBUTE_REQUIREMENTS_SCHEMA = {
 
 def _parse_attribute_requirements_def(
     attribute_requirements: Any,
-) -> List[SsoAttributeRequirement]:
+) -> list[SsoAttributeRequirement]:
     validate_config(
         ATTRIBUTE_REQUIREMENTS_SCHEMA,
         attribute_requirements,
diff --git a/synapse/config/server.py b/synapse/config/server.py
index e15bceb296..495f289159 100644
--- a/synapse/config/server.py
+++ b/synapse/config/server.py
@@ -25,7 +25,7 @@ import logging
 import os.path
 import urllib.parse
 from textwrap import indent
-from typing import Any, Dict, Iterable, List, Optional, Set, Tuple, TypedDict, Union
+from typing import Any, Iterable, TypedDict
 from urllib.request import getproxies_environment
 
 import attr
@@ -95,9 +95,9 @@ def _6to4(network: IPNetwork) -> IPNetwork:
 
 
 def generate_ip_set(
-    ip_addresses: Optional[Iterable[str]],
-    extra_addresses: Optional[Iterable[str]] = None,
-    config_path: Optional[StrSequence] = None,
+    ip_addresses: Iterable[str] | None,
+    extra_addresses: Iterable[str] | None = None,
+    config_path: StrSequence | None = None,
 ) -> IPSet:
     """
     Generate an IPSet from a list of IP addresses or CIDRs.
@@ -213,7 +213,7 @@ KNOWN_RESOURCES = {
 
 @attr.s(frozen=True)
 class HttpResourceConfig:
-    names: List[str] = attr.ib(
+    names: list[str] = attr.ib(
         factory=list,
         validator=attr.validators.deep_iterable(attr.validators.in_(KNOWN_RESOURCES)),
     )
@@ -228,10 +228,10 @@ class HttpListenerConfig:
     """Object describing the http-specific parts of the config of a listener"""
 
     x_forwarded: bool = False
-    resources: List[HttpResourceConfig] = attr.Factory(list)
-    additional_resources: Dict[str, dict] = attr.Factory(dict)
-    tag: Optional[str] = None
-    request_id_header: Optional[str] = None
+    resources: list[HttpResourceConfig] = attr.Factory(list)
+    additional_resources: dict[str, dict] = attr.Factory(dict)
+    tag: str | None = None
+    request_id_header: str | None = None
 
 
 @attr.s(slots=True, frozen=True, auto_attribs=True)
@@ -239,12 +239,12 @@ class TCPListenerConfig:
     """Object describing the configuration of a single TCP listener."""
 
     port: int = attr.ib(validator=attr.validators.instance_of(int))
-    bind_addresses: List[str] = attr.ib(validator=attr.validators.instance_of(List))
+    bind_addresses: list[str] = attr.ib(validator=attr.validators.instance_of(list))
     type: str = attr.ib(validator=attr.validators.in_(KNOWN_LISTENER_TYPES))
     tls: bool = False
 
     # http_options is only populated if type=http
-    http_options: Optional[HttpListenerConfig] = None
+    http_options: HttpListenerConfig | None = None
 
     def get_site_tag(self) -> str:
         """Retrieves http_options.tag if it exists, otherwise the port number."""
@@ -269,7 +269,7 @@ class UnixListenerConfig:
     type: str = attr.ib(validator=attr.validators.in_(KNOWN_LISTENER_TYPES))
 
     # http_options is only populated if type=http
-    http_options: Optional[HttpListenerConfig] = None
+    http_options: HttpListenerConfig | None = None
 
     def get_site_tag(self) -> str:
         return "unix"
@@ -279,7 +279,7 @@ class UnixListenerConfig:
         return False
 
 
-ListenerConfig = Union[TCPListenerConfig, UnixListenerConfig]
+ListenerConfig = TCPListenerConfig | UnixListenerConfig
 
 
 @attr.s(slots=True, frozen=True, auto_attribs=True)
@@ -288,14 +288,14 @@ class ManholeConfig:
 
     username: str = attr.ib(validator=attr.validators.instance_of(str))
     password: str = attr.ib(validator=attr.validators.instance_of(str))
-    priv_key: Optional[Key]
-    pub_key: Optional[Key]
+    priv_key: Key | None
+    pub_key: Key | None
 
 
 @attr.s(frozen=True)
 class LimitRemoteRoomsConfig:
     enabled: bool = attr.ib(validator=attr.validators.instance_of(bool), default=False)
-    complexity: Union[float, int] = attr.ib(
+    complexity: float | int = attr.ib(
         validator=attr.validators.instance_of((float, int)),  # noqa
         default=1.0,
     )
@@ -313,11 +313,11 @@ class ProxyConfigDictionary(TypedDict):
     Dictionary of proxy settings suitable for interacting with `urllib.request` API's
     """
 
-    http: Optional[str]
+    http: str | None
     """
     Proxy server to use for HTTP requests.
     """
-    https: Optional[str]
+    https: str | None
     """
     Proxy server to use for HTTPS requests.
     """
@@ -336,15 +336,15 @@ class ProxyConfig:
     Synapse configuration for HTTP proxy settings.
     """
 
-    http_proxy: Optional[str]
+    http_proxy: str | None
     """
     Proxy server to use for HTTP requests.
     """
-    https_proxy: Optional[str]
+    https_proxy: str | None
     """
     Proxy server to use for HTTPS requests.
     """
-    no_proxy_hosts: Optional[List[str]]
+    no_proxy_hosts: list[str] | None
     """
     List of hosts, IP addresses, or IP ranges in CIDR format which should not use the
     proxy. Synapse will directly connect to these hosts.
@@ -607,7 +607,7 @@ class ServerConfig(Config):
         # before redacting them.
         redaction_retention_period = config.get("redaction_retention_period", "7d")
         if redaction_retention_period is not None:
-            self.redaction_retention_period: Optional[int] = self.parse_duration(
+            self.redaction_retention_period: int | None = self.parse_duration(
                 redaction_retention_period
             )
         else:
@@ -618,7 +618,7 @@ class ServerConfig(Config):
             "forgotten_room_retention_period", None
         )
         if forgotten_room_retention_period is not None:
-            self.forgotten_room_retention_period: Optional[int] = self.parse_duration(
+            self.forgotten_room_retention_period: int | None = self.parse_duration(
                 forgotten_room_retention_period
             )
         else:
@@ -627,7 +627,7 @@ class ServerConfig(Config):
         # How long to keep entries in the `users_ips` table.
         user_ips_max_age = config.get("user_ips_max_age", "28d")
         if user_ips_max_age is not None:
-            self.user_ips_max_age: Optional[int] = self.parse_duration(user_ips_max_age)
+            self.user_ips_max_age: int | None = self.parse_duration(user_ips_max_age)
         else:
             self.user_ips_max_age = None
 
@@ -864,11 +864,11 @@ class ServerConfig(Config):
         )
 
         # Whitelist of domain names that given next_link parameters must have
-        next_link_domain_whitelist: Optional[List[str]] = config.get(
+        next_link_domain_whitelist: list[str] | None = config.get(
             "next_link_domain_whitelist"
         )
 
-        self.next_link_domain_whitelist: Optional[Set[str]] = None
+        self.next_link_domain_whitelist: set[str] | None = None
         if next_link_domain_whitelist is not None:
             if not isinstance(next_link_domain_whitelist, list):
                 raise ConfigError("'next_link_domain_whitelist' must be a list")
@@ -880,7 +880,7 @@ class ServerConfig(Config):
         if not isinstance(templates_config, dict):
             raise ConfigError("The 'templates' section must be a dictionary")
 
-        self.custom_template_directory: Optional[str] = templates_config.get(
+        self.custom_template_directory: str | None = templates_config.get(
             "custom_template_directory"
         )
         if self.custom_template_directory is not None and not isinstance(
@@ -892,16 +892,16 @@ class ServerConfig(Config):
             config.get("use_account_validity_in_account_status") or False
         )
 
-        self.rooms_to_exclude_from_sync: List[str] = (
+        self.rooms_to_exclude_from_sync: list[str] = (
             config.get("exclude_rooms_from_sync") or []
         )
 
-        delete_stale_devices_after: Optional[str] = (
+        delete_stale_devices_after: str | None = (
             config.get("delete_stale_devices_after") or None
         )
 
         if delete_stale_devices_after is not None:
-            self.delete_stale_devices_after: Optional[int] = self.parse_duration(
+            self.delete_stale_devices_after: int | None = self.parse_duration(
                 delete_stale_devices_after
             )
         else:
@@ -910,7 +910,7 @@ class ServerConfig(Config):
         # The maximum allowed delay duration for delayed events (MSC4140).
         max_event_delay_duration = config.get("max_event_delay_duration")
         if max_event_delay_duration is not None:
-            self.max_event_delay_ms: Optional[int] = self.parse_duration(
+            self.max_event_delay_ms: int | None = self.parse_duration(
                 max_event_delay_duration
             )
             if self.max_event_delay_ms <= 0:
@@ -927,7 +927,7 @@ class ServerConfig(Config):
         data_dir_path: str,
         server_name: str,
         open_private_ports: bool,
-        listeners: Optional[List[dict]],
+        listeners: list[dict] | None,
         **kwargs: Any,
     ) -> str:
         _, bind_port = parse_and_validate_server_name(server_name)
@@ -1028,7 +1028,7 @@ class ServerConfig(Config):
             help="Turn on the twisted telnet manhole service on the given port.",
         )
 
-    def read_gc_intervals(self, durations: Any) -> Optional[Tuple[float, float, float]]:
+    def read_gc_intervals(self, durations: Any) -> tuple[float, float, float] | None:
         """Reads the three durations for the GC min interval option, returning seconds."""
         if durations is None:
             return None
@@ -1048,7 +1048,7 @@ class ServerConfig(Config):
 
 
 def is_threepid_reserved(
-    reserved_threepids: List[JsonDict], threepid: JsonDict
+    reserved_threepids: list[JsonDict], threepid: JsonDict
 ) -> bool:
     """Check the threepid against the reserved threepid config
     Args:
@@ -1066,8 +1066,8 @@ def is_threepid_reserved(
 
 
 def read_gc_thresholds(
-    thresholds: Optional[List[Any]],
-) -> Optional[Tuple[int, int, int]]:
+    thresholds: list[Any] | None,
+) -> tuple[int, int, int] | None:
     """Reads the three integer thresholds for garbage collection. Ensures that
     the thresholds are integers if thresholds are supplied.
     """
diff --git a/synapse/config/server_notices.py b/synapse/config/server_notices.py
index 4de2d62b54..d19e2569a1 100644
--- a/synapse/config/server_notices.py
+++ b/synapse/config/server_notices.py
@@ -18,7 +18,7 @@
 #
 #
 
-from typing import Any, Optional
+from typing import Any
 
 from synapse.types import JsonDict, UserID
 
@@ -58,12 +58,12 @@ class ServerNoticesConfig(Config):
 
     def __init__(self, *args: Any):
         super().__init__(*args)
-        self.server_notices_mxid: Optional[str] = None
-        self.server_notices_mxid_display_name: Optional[str] = None
-        self.server_notices_mxid_avatar_url: Optional[str] = None
-        self.server_notices_room_name: Optional[str] = None
-        self.server_notices_room_avatar_url: Optional[str] = None
-        self.server_notices_room_topic: Optional[str] = None
+        self.server_notices_mxid: str | None = None
+        self.server_notices_mxid_display_name: str | None = None
+        self.server_notices_mxid_avatar_url: str | None = None
+        self.server_notices_room_name: str | None = None
+        self.server_notices_room_avatar_url: str | None = None
+        self.server_notices_room_topic: str | None = None
         self.server_notices_auto_join: bool = False
 
     def read_config(self, config: JsonDict, **kwargs: Any) -> None:
diff --git a/synapse/config/spam_checker.py b/synapse/config/spam_checker.py
index 014c55d702..02d7cee88f 100644
--- a/synapse/config/spam_checker.py
+++ b/synapse/config/spam_checker.py
@@ -19,7 +19,7 @@
 #
 
 import logging
-from typing import Any, Dict, List, Tuple
+from typing import Any
 
 from synapse.config import ConfigError
 from synapse.types import JsonDict
@@ -41,7 +41,7 @@ class SpamCheckerConfig(Config):
     section = "spamchecker"
 
     def read_config(self, config: JsonDict, **kwargs: Any) -> None:
-        self.spam_checkers: List[Tuple[Any, Dict]] = []
+        self.spam_checkers: list[tuple[Any, dict]] = []
 
         spam_checkers = config.get("spam_checker") or []
         if isinstance(spam_checkers, dict):
diff --git a/synapse/config/sso.py b/synapse/config/sso.py
index cf27a7ee13..1d08bef868 100644
--- a/synapse/config/sso.py
+++ b/synapse/config/sso.py
@@ -19,7 +19,7 @@
 #
 #
 import logging
-from typing import Any, Dict, List, Optional
+from typing import Any
 
 import attr
 
@@ -44,8 +44,8 @@ class SsoAttributeRequirement:
 
     attribute: str
     # If neither `value` nor `one_of` is given, the attribute must simply exist.
-    value: Optional[str] = None
-    one_of: Optional[List[str]] = None
+    value: str | None = None
+    one_of: list[str] | None = None
 
     JSON_SCHEMA = {
         "type": "object",
@@ -64,7 +64,7 @@ class SSOConfig(Config):
     section = "sso"
 
     def read_config(self, config: JsonDict, **kwargs: Any) -> None:
-        sso_config: Dict[str, Any] = config.get("sso") or {}
+        sso_config: dict[str, Any] = config.get("sso") or {}
 
         # The sso-specific template_dir
         self.sso_template_dir = sso_config.get("template_dir")
diff --git a/synapse/config/tls.py b/synapse/config/tls.py
index a48d81fdc3..de4d676e08 100644
--- a/synapse/config/tls.py
+++ b/synapse/config/tls.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import Any, List, Optional, Pattern
+from typing import Any, Pattern
 
 from matrix_common.regex import glob_to_regex
 
@@ -84,7 +84,7 @@ class TlsConfig(Config):
             fed_whitelist_entries = []
 
         # Support globs (*) in whitelist values
-        self.federation_certificate_verification_whitelist: List[Pattern] = []
+        self.federation_certificate_verification_whitelist: list[Pattern] = []
         for entry in fed_whitelist_entries:
             try:
                 entry_regex = glob_to_regex(entry.encode("ascii").decode("ascii"))
@@ -135,8 +135,8 @@ class TlsConfig(Config):
             "use_insecure_ssl_client_just_for_testing_do_not_use"
         )
 
-        self.tls_certificate: Optional[crypto.X509] = None
-        self.tls_private_key: Optional[crypto.PKey] = None
+        self.tls_certificate: crypto.X509 | None = None
+        self.tls_private_key: crypto.PKey | None = None
 
     def read_certificate_from_disk(self) -> None:
         """
@@ -147,8 +147,8 @@ class TlsConfig(Config):
 
     def generate_config_section(
         self,
-        tls_certificate_path: Optional[str],
-        tls_private_key_path: Optional[str],
+        tls_certificate_path: str | None,
+        tls_private_key_path: str | None,
         **kwargs: Any,
     ) -> str:
         """If the TLS paths are not specified the default will be certs in the
diff --git a/synapse/config/tracer.py b/synapse/config/tracer.py
index d31fd41082..ccfeed4d07 100644
--- a/synapse/config/tracer.py
+++ b/synapse/config/tracer.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import Any, List, Set
+from typing import Any
 
 from synapse.types import JsonDict
 from synapse.util.check_dependencies import check_requirements
@@ -42,7 +42,7 @@ class TracerConfig(Config):
             {"sampler": {"type": "const", "param": 1}, "logging": False},
         )
 
-        self.force_tracing_for_users: Set[str] = set()
+        self.force_tracing_for_users: set[str] = set()
 
         if not self.opentracer_enabled:
             return
@@ -51,7 +51,7 @@ class TracerConfig(Config):
 
         # The tracer is enabled so sanitize the config
 
-        self.opentracer_whitelist: List[str] = opentracing_config.get(
+        self.opentracer_whitelist: list[str] = opentracing_config.get(
             "homeserver_whitelist", []
         )
         if not isinstance(self.opentracer_whitelist, list):
diff --git a/synapse/config/user_types.py b/synapse/config/user_types.py
index 2d9c9f7afb..e47713b7f4 100644
--- a/synapse/config/user_types.py
+++ b/synapse/config/user_types.py
@@ -12,7 +12,7 @@
 # <https://www.gnu.org/licenses/agpl-3.0.html>.
 #
 
-from typing import Any, List, Optional
+from typing import Any
 
 from synapse.api.constants import UserTypes
 from synapse.types import JsonDict
@@ -26,12 +26,10 @@ class UserTypesConfig(Config):
     def read_config(self, config: JsonDict, **kwargs: Any) -> None:
         user_types: JsonDict = config.get("user_types", {})
 
-        self.default_user_type: Optional[str] = user_types.get(
-            "default_user_type", None
-        )
-        self.extra_user_types: List[str] = user_types.get("extra_user_types", [])
+        self.default_user_type: str | None = user_types.get("default_user_type", None)
+        self.extra_user_types: list[str] = user_types.get("extra_user_types", [])
 
-        all_user_types: List[str] = []
+        all_user_types: list[str] = []
         all_user_types.extend(UserTypes.ALL_BUILTIN_USER_TYPES)
         all_user_types.extend(self.extra_user_types)
 
diff --git a/synapse/config/workers.py b/synapse/config/workers.py
index 825ba78482..ec8ab9506b 100644
--- a/synapse/config/workers.py
+++ b/synapse/config/workers.py
@@ -22,15 +22,15 @@
 
 import argparse
 import logging
-from typing import Any, Dict, List, Optional, Union
+from typing import Any
 
 import attr
-
-from synapse._pydantic_compat import (
+from pydantic import (
     StrictBool,
     StrictInt,
     StrictStr,
 )
+
 from synapse.config._base import (
     Config,
     ConfigError,
@@ -79,7 +79,7 @@ MAIN_PROCESS_INSTANCE_MAP_NAME = "main"
 logger = logging.getLogger(__name__)
 
 
-def _instance_to_list_converter(obj: Union[str, List[str]]) -> List[str]:
+def _instance_to_list_converter(obj: str | list[str]) -> list[str]:
     """Helper for allowing parsing a string or list of strings to a config
     option expecting a list of strings.
     """
@@ -119,7 +119,7 @@ class InstanceUnixLocationConfig(ParseModel):
         return f"{self.path}"
 
 
-InstanceLocationConfig = Union[InstanceTcpLocationConfig, InstanceUnixLocationConfig]
+InstanceLocationConfig = InstanceTcpLocationConfig | InstanceUnixLocationConfig
 
 
 @attr.s
@@ -142,39 +142,39 @@ class WriterLocations:
         device_lists: The instances that write to the device list stream.
     """
 
-    events: List[str] = attr.ib(
+    events: list[str] = attr.ib(
         default=[MAIN_PROCESS_INSTANCE_NAME],
         converter=_instance_to_list_converter,
     )
-    typing: List[str] = attr.ib(
+    typing: list[str] = attr.ib(
         default=[MAIN_PROCESS_INSTANCE_NAME],
         converter=_instance_to_list_converter,
     )
-    to_device: List[str] = attr.ib(
+    to_device: list[str] = attr.ib(
         default=[MAIN_PROCESS_INSTANCE_NAME],
         converter=_instance_to_list_converter,
     )
-    account_data: List[str] = attr.ib(
+    account_data: list[str] = attr.ib(
         default=[MAIN_PROCESS_INSTANCE_NAME],
         converter=_instance_to_list_converter,
     )
-    receipts: List[str] = attr.ib(
+    receipts: list[str] = attr.ib(
         default=[MAIN_PROCESS_INSTANCE_NAME],
         converter=_instance_to_list_converter,
     )
-    presence: List[str] = attr.ib(
+    presence: list[str] = attr.ib(
         default=[MAIN_PROCESS_INSTANCE_NAME],
         converter=_instance_to_list_converter,
     )
-    push_rules: List[str] = attr.ib(
+    push_rules: list[str] = attr.ib(
         default=[MAIN_PROCESS_INSTANCE_NAME],
         converter=_instance_to_list_converter,
     )
-    device_lists: List[str] = attr.ib(
+    device_lists: list[str] = attr.ib(
         default=[MAIN_PROCESS_INSTANCE_NAME],
         converter=_instance_to_list_converter,
     )
-    thread_subscriptions: List[str] = attr.ib(
+    thread_subscriptions: list[str] = attr.ib(
         default=["master"],
         converter=_instance_to_list_converter,
     )
@@ -190,8 +190,8 @@ class OutboundFederationRestrictedTo:
         locations: list of instance locations to connect to proxy via.
     """
 
-    instances: Optional[List[str]]
-    locations: List[InstanceLocationConfig] = attr.Factory(list)
+    instances: list[str] | None
+    locations: list[InstanceLocationConfig] = attr.Factory(list)
 
     def __contains__(self, instance: str) -> bool:
         # It feels a bit dirty to return `True` if `instances` is `None`, but it makes
@@ -246,7 +246,7 @@ class WorkerConfig(Config):
         if worker_replication_secret_path:
             if worker_replication_secret:
                 raise ConfigError(CONFLICTING_WORKER_REPLICATION_SECRET_OPTS_ERROR)
-            self.worker_replication_secret: Optional[str] = read_file(
+            self.worker_replication_secret: str | None = read_file(
                 worker_replication_secret_path, ("worker_replication_secret_path",)
             ).strip()
         else:
@@ -295,7 +295,7 @@ class WorkerConfig(Config):
         # A map from instance name to host/port of their HTTP replication endpoint.
         # Check if the main process is declared. The main process itself doesn't need
         # this data as it would never have to talk to itself.
-        instance_map: Dict[str, Any] = config.get("instance_map", {})
+        instance_map: dict[str, Any] = config.get("instance_map", {})
 
         if self.instance_name is not MAIN_PROCESS_INSTANCE_NAME:
             # TODO: The next 3 condition blocks can be deleted after some time has
@@ -341,8 +341,8 @@ class WorkerConfig(Config):
                     % MAIN_PROCESS_INSTANCE_MAP_NAME
                 )
 
-        # type-ignore: the expression `Union[A, B]` is not a Type[Union[A, B]] currently
-        self.instance_map: Dict[str, InstanceLocationConfig] = (
+        # type-ignore: the expression `A | B` is not a `type[A | B]` currently
+        self.instance_map: dict[str, InstanceLocationConfig] = (
             parse_and_validate_mapping(
                 instance_map,
                 InstanceLocationConfig,  # type: ignore[arg-type]
@@ -481,7 +481,7 @@ class WorkerConfig(Config):
 
     def _should_this_worker_perform_duty(
         self,
-        config: Dict[str, Any],
+        config: dict[str, Any],
         legacy_master_option_name: str,
         legacy_worker_app_name: str,
         new_option_name: str,
@@ -574,11 +574,11 @@ class WorkerConfig(Config):
 
     def _worker_names_performing_this_duty(
         self,
-        config: Dict[str, Any],
+        config: dict[str, Any],
         legacy_option_name: str,
         legacy_app_name: str,
         modern_instance_list_name: str,
-    ) -> List[str]:
+    ) -> list[str]:
         """
         Retrieves the names of the workers handling a given duty, by either legacy
         option or instance list.
diff --git a/synapse/crypto/event_signing.py b/synapse/crypto/event_signing.py
index c36398cec0..d13d5d04c3 100644
--- a/synapse/crypto/event_signing.py
+++ b/synapse/crypto/event_signing.py
@@ -23,7 +23,7 @@
 import collections.abc
 import hashlib
 import logging
-from typing import Any, Callable, Dict, Tuple
+from typing import Any, Callable
 
 from canonicaljson import encode_canonical_json
 from signedjson.sign import sign_json
@@ -80,8 +80,8 @@ def check_event_content_hash(
 
 
 def compute_content_hash(
-    event_dict: Dict[str, Any], hash_algorithm: Hasher
-) -> Tuple[str, bytes]:
+    event_dict: dict[str, Any], hash_algorithm: Hasher
+) -> tuple[str, bytes]:
     """Compute the content hash of an event, which is the hash of the
     unredacted event.
 
@@ -112,7 +112,7 @@ def compute_content_hash(
 
 def compute_event_reference_hash(
     event: EventBase, hash_algorithm: Hasher = hashlib.sha256
-) -> Tuple[str, bytes]:
+) -> tuple[str, bytes]:
     """Computes the event reference hash. This is the hash of the redacted
     event.
 
@@ -139,7 +139,7 @@ def compute_event_signature(
     event_dict: JsonDict,
     signature_name: str,
     signing_key: SigningKey,
-) -> Dict[str, Dict[str, str]]:
+) -> dict[str, dict[str, str]]:
     """Compute the signature of the event for the given name and key.
 
     Args:
diff --git a/synapse/crypto/keyring.py b/synapse/crypto/keyring.py
index eac2d776f9..3abb644df5 100644
--- a/synapse/crypto/keyring.py
+++ b/synapse/crypto/keyring.py
@@ -21,7 +21,7 @@
 
 import abc
 import logging
-from typing import TYPE_CHECKING, Callable, Dict, Iterable, List, Optional, Tuple
+from typing import TYPE_CHECKING, Callable, Iterable
 
 import attr
 from signedjson.key import (
@@ -82,7 +82,7 @@ class VerifyJsonRequest:
     server_name: str
     get_json_object: Callable[[], JsonDict]
     minimum_valid_until_ts: int
-    key_ids: List[str]
+    key_ids: list[str]
 
     @staticmethod
     def from_json_object(
@@ -141,7 +141,7 @@ class _FetchKeyRequest:
 
     server_name: str
     minimum_valid_until_ts: int
-    key_ids: List[str]
+    key_ids: list[str]
 
 
 class Keyring:
@@ -150,13 +150,13 @@ class Keyring:
     """
 
     def __init__(
-        self, hs: "HomeServer", key_fetchers: "Optional[Iterable[KeyFetcher]]" = None
+        self, hs: "HomeServer", key_fetchers: "Iterable[KeyFetcher] | None" = None
     ):
         self.server_name = hs.hostname
 
         if key_fetchers is None:
             # Always fetch keys from the database.
-            mutable_key_fetchers: List[KeyFetcher] = [StoreKeyFetcher(hs)]
+            mutable_key_fetchers: list[KeyFetcher] = [StoreKeyFetcher(hs)]
             # Fetch keys from configured trusted key servers, if any exist.
             key_servers = hs.config.key.key_servers
             if key_servers:
@@ -169,10 +169,10 @@ class Keyring:
             self._key_fetchers = key_fetchers
 
         self._fetch_keys_queue: BatchingQueue[
-            _FetchKeyRequest, Dict[str, Dict[str, FetchKeyResult]]
+            _FetchKeyRequest, dict[str, dict[str, FetchKeyResult]]
         ] = BatchingQueue(
             name="keyring_server",
-            server_name=self.server_name,
+            hs=hs,
             clock=hs.get_clock(),
             # The method called to fetch each key
             process_batch_callback=self._inner_fetch_key_requests,
@@ -182,7 +182,7 @@ class Keyring:
 
         # build a FetchKeyResult for each of our own keys, to shortcircuit the
         # fetcher.
-        self._local_verify_keys: Dict[str, FetchKeyResult] = {}
+        self._local_verify_keys: dict[str, FetchKeyResult] = {}
         for key_id, key in hs.config.key.old_signing_keys.items():
             self._local_verify_keys[key_id] = FetchKeyResult(
                 verify_key=key, valid_until_ts=key.expired
@@ -194,6 +194,14 @@ class Keyring:
             valid_until_ts=2**63,  # fake future timestamp
         )
 
+    def shutdown(self) -> None:
+        """
+        Prepares the KeyRing for garbage collection by shutting down it's queues.
+        """
+        self._fetch_keys_queue.shutdown()
+        for key_fetcher in self._key_fetchers:
+            key_fetcher.shutdown()
+
     async def verify_json_for_server(
         self,
         server_name: str,
@@ -221,8 +229,8 @@ class Keyring:
         return await self.process_request(request)
 
     def verify_json_objects_for_server(
-        self, server_and_json: Iterable[Tuple[str, dict, int]]
-    ) -> List["defer.Deferred[None]"]:
+        self, server_and_json: Iterable[tuple[str, dict, int]]
+    ) -> list["defer.Deferred[None]"]:
         """Bulk verifies signatures of json objects, bulk fetching keys as
         necessary.
 
@@ -278,7 +286,7 @@ class Keyring:
                 Codes.UNAUTHORIZED,
             )
 
-        found_keys: Dict[str, FetchKeyResult] = {}
+        found_keys: dict[str, FetchKeyResult] = {}
 
         # If we are the originating server, short-circuit the key-fetch for any keys
         # we already have
@@ -360,8 +368,8 @@ class Keyring:
             )
 
     async def _inner_fetch_key_requests(
-        self, requests: List[_FetchKeyRequest]
-    ) -> Dict[str, Dict[str, FetchKeyResult]]:
+        self, requests: list[_FetchKeyRequest]
+    ) -> dict[str, dict[str, FetchKeyResult]]:
         """Processing function for the queue of `_FetchKeyRequest`.
 
         Takes a list of key fetch requests, de-duplicates them and then carries out
@@ -379,7 +387,7 @@ class Keyring:
         # First we need to deduplicate requests for the same key. We do this by
         # taking the *maximum* requested `minimum_valid_until_ts` for each pair
         # of server name/key ID.
-        server_to_key_to_ts: Dict[str, Dict[str, int]] = {}
+        server_to_key_to_ts: dict[str, dict[str, int]] = {}
         for request in requests:
             by_server = server_to_key_to_ts.setdefault(request.server_name, {})
             for key_id in request.key_ids:
@@ -404,7 +412,7 @@ class Keyring:
 
         # We now convert the returned list of results into a map from server
         # name to key ID to FetchKeyResult, to return.
-        to_return: Dict[str, Dict[str, FetchKeyResult]] = {}
+        to_return: dict[str, dict[str, FetchKeyResult]] = {}
         for request, results in zip(deduped_requests, results_per_request):
             to_return_by_server = to_return.setdefault(request.server_name, {})
             for key_id, key_result in results.items():
@@ -416,7 +424,7 @@ class Keyring:
 
     async def _inner_fetch_key_request(
         self, verify_request: _FetchKeyRequest
-    ) -> Dict[str, FetchKeyResult]:
+    ) -> dict[str, FetchKeyResult]:
         """Attempt to fetch the given key by calling each key fetcher one by one.
 
         If a key is found, check whether its `valid_until_ts` attribute satisfies the
@@ -437,7 +445,7 @@ class Keyring:
         """
         logger.debug("Starting fetch for %s", verify_request)
 
-        found_keys: Dict[str, FetchKeyResult] = {}
+        found_keys: dict[str, FetchKeyResult] = {}
         missing_key_ids = set(verify_request.key_ids)
 
         for fetcher in self._key_fetchers:
@@ -479,14 +487,20 @@ class KeyFetcher(metaclass=abc.ABCMeta):
         self.server_name = hs.hostname
         self._queue = BatchingQueue(
             name=self.__class__.__name__,
-            server_name=self.server_name,
+            hs=hs,
             clock=hs.get_clock(),
             process_batch_callback=self._fetch_keys,
         )
 
+    def shutdown(self) -> None:
+        """
+        Prepares the KeyFetcher for garbage collection by shutting down it's queue.
+        """
+        self._queue.shutdown()
+
     async def get_keys(
-        self, server_name: str, key_ids: List[str], minimum_valid_until_ts: int
-    ) -> Dict[str, FetchKeyResult]:
+        self, server_name: str, key_ids: list[str], minimum_valid_until_ts: int
+    ) -> dict[str, FetchKeyResult]:
         results = await self._queue.add_to_queue(
             _FetchKeyRequest(
                 server_name=server_name,
@@ -498,8 +512,8 @@ class KeyFetcher(metaclass=abc.ABCMeta):
 
     @abc.abstractmethod
     async def _fetch_keys(
-        self, keys_to_fetch: List[_FetchKeyRequest]
-    ) -> Dict[str, Dict[str, FetchKeyResult]]:
+        self, keys_to_fetch: list[_FetchKeyRequest]
+    ) -> dict[str, dict[str, FetchKeyResult]]:
         pass
 
 
@@ -512,8 +526,8 @@ class StoreKeyFetcher(KeyFetcher):
         self.store = hs.get_datastores().main
 
     async def _fetch_keys(
-        self, keys_to_fetch: List[_FetchKeyRequest]
-    ) -> Dict[str, Dict[str, FetchKeyResult]]:
+        self, keys_to_fetch: list[_FetchKeyRequest]
+    ) -> dict[str, dict[str, FetchKeyResult]]:
         key_ids_to_fetch = (
             (queue_value.server_name, key_id)
             for queue_value in keys_to_fetch
@@ -521,7 +535,7 @@ class StoreKeyFetcher(KeyFetcher):
         )
 
         res = await self.store.get_server_keys_json(key_ids_to_fetch)
-        keys: Dict[str, Dict[str, FetchKeyResult]] = {}
+        keys: dict[str, dict[str, FetchKeyResult]] = {}
         for (server_name, key_id), key in res.items():
             keys.setdefault(server_name, {})[key_id] = key
         return keys
@@ -535,7 +549,7 @@ class BaseV2KeyFetcher(KeyFetcher):
 
     async def process_v2_response(
         self, from_server: str, response_json: JsonDict, time_added_ms: int
-    ) -> Dict[str, FetchKeyResult]:
+    ) -> dict[str, FetchKeyResult]:
         """Parse a 'Server Keys' structure from the result of a /key request
 
         This is used to parse either the entirety of the response from
@@ -626,11 +640,11 @@ class PerspectivesKeyFetcher(BaseV2KeyFetcher):
         self.key_servers = hs.config.key.key_servers
 
     async def _fetch_keys(
-        self, keys_to_fetch: List[_FetchKeyRequest]
-    ) -> Dict[str, Dict[str, FetchKeyResult]]:
+        self, keys_to_fetch: list[_FetchKeyRequest]
+    ) -> dict[str, dict[str, FetchKeyResult]]:
         """see KeyFetcher._fetch_keys"""
 
-        async def get_key(key_server: TrustedKeyServer) -> Dict:
+        async def get_key(key_server: TrustedKeyServer) -> dict:
             try:
                 return await self.get_server_verify_key_v2_indirect(
                     keys_to_fetch, key_server
@@ -656,7 +670,7 @@ class PerspectivesKeyFetcher(BaseV2KeyFetcher):
             ).addErrback(unwrapFirstError)
         )
 
-        union_of_keys: Dict[str, Dict[str, FetchKeyResult]] = {}
+        union_of_keys: dict[str, dict[str, FetchKeyResult]] = {}
         for result in results:
             for server_name, keys in result.items():
                 union_of_keys.setdefault(server_name, {}).update(keys)
@@ -664,8 +678,8 @@ class PerspectivesKeyFetcher(BaseV2KeyFetcher):
         return union_of_keys
 
     async def get_server_verify_key_v2_indirect(
-        self, keys_to_fetch: List[_FetchKeyRequest], key_server: TrustedKeyServer
-    ) -> Dict[str, Dict[str, FetchKeyResult]]:
+        self, keys_to_fetch: list[_FetchKeyRequest], key_server: TrustedKeyServer
+    ) -> dict[str, dict[str, FetchKeyResult]]:
         """
         Args:
             keys_to_fetch:
@@ -717,8 +731,8 @@ class PerspectivesKeyFetcher(BaseV2KeyFetcher):
             "Response from notary server %s: %s", perspective_name, query_response
         )
 
-        keys: Dict[str, Dict[str, FetchKeyResult]] = {}
-        added_keys: Dict[Tuple[str, str], FetchKeyResult] = {}
+        keys: dict[str, dict[str, FetchKeyResult]] = {}
+        added_keys: dict[tuple[str, str], FetchKeyResult] = {}
 
         time_now_ms = self.clock.time_msec()
 
@@ -822,8 +836,8 @@ class ServerKeyFetcher(BaseV2KeyFetcher):
         self.client = hs.get_federation_http_client()
 
     async def get_keys(
-        self, server_name: str, key_ids: List[str], minimum_valid_until_ts: int
-    ) -> Dict[str, FetchKeyResult]:
+        self, server_name: str, key_ids: list[str], minimum_valid_until_ts: int
+    ) -> dict[str, FetchKeyResult]:
         results = await self._queue.add_to_queue(
             _FetchKeyRequest(
                 server_name=server_name,
@@ -835,8 +849,8 @@ class ServerKeyFetcher(BaseV2KeyFetcher):
         return results.get(server_name, {})
 
     async def _fetch_keys(
-        self, keys_to_fetch: List[_FetchKeyRequest]
-    ) -> Dict[str, Dict[str, FetchKeyResult]]:
+        self, keys_to_fetch: list[_FetchKeyRequest]
+    ) -> dict[str, dict[str, FetchKeyResult]]:
         """
         Args:
             keys_to_fetch:
@@ -865,7 +879,7 @@ class ServerKeyFetcher(BaseV2KeyFetcher):
 
     async def get_server_verify_keys_v2_direct(
         self, server_name: str
-    ) -> Dict[str, FetchKeyResult]:
+    ) -> dict[str, FetchKeyResult]:
         """
 
         Args:
diff --git a/synapse/event_auth.py b/synapse/event_auth.py
index 64de3f7ef8..66f50115e3 100644
--- a/synapse/event_auth.py
+++ b/synapse/event_auth.py
@@ -26,15 +26,11 @@ import typing
 from typing import (
     Any,
     ChainMap,
-    Dict,
     Iterable,
-    List,
     Mapping,
     MutableMapping,
     Optional,
     Protocol,
-    Set,
-    Tuple,
     Union,
     cast,
 )
@@ -91,7 +87,7 @@ class _EventSourceStore(Protocol):
         redact_behaviour: EventRedactBehaviour,
         get_prev_content: bool = False,
         allow_rejected: bool = False,
-    ) -> Dict[str, "EventBase"]: ...
+    ) -> dict[str, "EventBase"]: ...
 
 
 def validate_event_for_room_version(event: "EventBase") -> None:
@@ -164,7 +160,7 @@ def validate_event_for_room_version(event: "EventBase") -> None:
 async def check_state_independent_auth_rules(
     store: _EventSourceStore,
     event: "EventBase",
-    batched_auth_events: Optional[Mapping[str, "EventBase"]] = None,
+    batched_auth_events: Mapping[str, "EventBase"] | None = None,
 ) -> None:
     """Check that an event complies with auth rules that are independent of room state
 
@@ -792,7 +788,7 @@ def _check_joined_room(
 
 
 def get_send_level(
-    etype: str, state_key: Optional[str], power_levels_event: Optional["EventBase"]
+    etype: str, state_key: str | None, power_levels_event: Optional["EventBase"]
 ) -> int:
     """Get the power level required to send an event of a given type
 
@@ -993,7 +989,7 @@ def _check_power_levels(
     user_level = get_user_power_level(event.user_id, auth_events)
 
     # Check other levels:
-    levels_to_check: List[Tuple[str, Optional[str]]] = [
+    levels_to_check: list[tuple[str, str | None]] = [
         ("users_default", None),
         ("events_default", None),
         ("state_default", None),
@@ -1031,12 +1027,12 @@ def _check_power_levels(
             new_loc = new_loc.get(dir, {})
 
         if level_to_check in old_loc:
-            old_level: Optional[int] = int(old_loc[level_to_check])
+            old_level: int | None = int(old_loc[level_to_check])
         else:
             old_level = None
 
         if level_to_check in new_loc:
-            new_level: Optional[int] = int(new_loc[level_to_check])
+            new_level: int | None = int(new_loc[level_to_check])
         else:
             new_level = None
 
@@ -1191,7 +1187,7 @@ def _verify_third_party_invite(
     return False
 
 
-def get_public_keys(invite_event: "EventBase") -> List[Dict[str, Any]]:
+def get_public_keys(invite_event: "EventBase") -> list[dict[str, Any]]:
     public_keys = []
     if "public_key" in invite_event.content:
         o = {"public_key": invite_event.content["public_key"]}
@@ -1204,7 +1200,7 @@ def get_public_keys(invite_event: "EventBase") -> List[Dict[str, Any]]:
 
 def auth_types_for_event(
     room_version: RoomVersion, event: Union["EventBase", "EventBuilder"]
-) -> Set[Tuple[str, str]]:
+) -> set[tuple[str, str]]:
     """Given an event, return a list of (EventType, StateKey) that may be
     needed to auth the event. The returned list may be a superset of what
     would actually be required depending on the full state of the room.
diff --git a/synapse/events/__init__.py b/synapse/events/__init__.py
index db38754280..5f78603782 100644
--- a/synapse/events/__init__.py
+++ b/synapse/events/__init__.py
@@ -25,14 +25,9 @@ import collections.abc
 from typing import (
     TYPE_CHECKING,
     Any,
-    Dict,
     Generic,
     Iterable,
-    List,
     Literal,
-    Optional,
-    Tuple,
-    Type,
     TypeVar,
     Union,
     overload,
@@ -94,21 +89,21 @@ class DictProperty(Generic[T]):
     def __get__(
         self,
         instance: Literal[None],
-        owner: Optional[Type[_DictPropertyInstance]] = None,
+        owner: type[_DictPropertyInstance] | None = None,
     ) -> "DictProperty": ...
 
     @overload
     def __get__(
         self,
         instance: _DictPropertyInstance,
-        owner: Optional[Type[_DictPropertyInstance]] = None,
+        owner: type[_DictPropertyInstance] | None = None,
     ) -> T: ...
 
     def __get__(
         self,
-        instance: Optional[_DictPropertyInstance],
-        owner: Optional[Type[_DictPropertyInstance]] = None,
-    ) -> Union[T, "DictProperty"]:
+        instance: _DictPropertyInstance | None,
+        owner: type[_DictPropertyInstance] | None = None,
+    ) -> T | "DictProperty":
         # if the property is accessed as a class property rather than an instance
         # property, return the property itself rather than the value
         if instance is None:
@@ -160,21 +155,21 @@ class DefaultDictProperty(DictProperty, Generic[T]):
     def __get__(
         self,
         instance: Literal[None],
-        owner: Optional[Type[_DictPropertyInstance]] = None,
+        owner: type[_DictPropertyInstance] | None = None,
     ) -> "DefaultDictProperty": ...
 
     @overload
     def __get__(
         self,
         instance: _DictPropertyInstance,
-        owner: Optional[Type[_DictPropertyInstance]] = None,
+        owner: type[_DictPropertyInstance] | None = None,
     ) -> T: ...
 
     def __get__(
         self,
-        instance: Optional[_DictPropertyInstance],
-        owner: Optional[Type[_DictPropertyInstance]] = None,
-    ) -> Union[T, "DefaultDictProperty"]:
+        instance: _DictPropertyInstance | None,
+        owner: type[_DictPropertyInstance] | None = None,
+    ) -> T | "DefaultDictProperty":
         if instance is None:
             return self
         assert isinstance(instance, EventBase)
@@ -192,10 +187,10 @@ class EventBase(metaclass=abc.ABCMeta):
         self,
         event_dict: JsonDict,
         room_version: RoomVersion,
-        signatures: Dict[str, Dict[str, str]],
+        signatures: dict[str, dict[str, str]],
         unsigned: JsonDict,
         internal_metadata_dict: JsonDict,
-        rejected_reason: Optional[str],
+        rejected_reason: str | None,
     ):
         assert room_version.event_format == self.format_version
 
@@ -210,10 +205,10 @@ class EventBase(metaclass=abc.ABCMeta):
 
     depth: DictProperty[int] = DictProperty("depth")
     content: DictProperty[JsonDict] = DictProperty("content")
-    hashes: DictProperty[Dict[str, str]] = DictProperty("hashes")
+    hashes: DictProperty[dict[str, str]] = DictProperty("hashes")
     origin_server_ts: DictProperty[int] = DictProperty("origin_server_ts")
     sender: DictProperty[str] = DictProperty("sender")
-    # TODO state_key should be Optional[str]. This is generally asserted in Synapse
+    # TODO state_key should be str | None. This is generally asserted in Synapse
     # by calling is_state() first (which ensures it is not None), but it is hard (not possible?)
     # to properly annotate that calling is_state() asserts that state_key exists
     # and is non-None. It would be better to replace such direct references with
@@ -235,7 +230,7 @@ class EventBase(metaclass=abc.ABCMeta):
         return self.content["membership"]
 
     @property
-    def redacts(self) -> Optional[str]:
+    def redacts(self) -> str | None:
         """MSC2176 moved the redacts field into the content."""
         if self.room_version.updated_redaction_rules:
             return self.content.get("redacts")
@@ -244,7 +239,7 @@ class EventBase(metaclass=abc.ABCMeta):
     def is_state(self) -> bool:
         return self.get_state_key() is not None
 
-    def get_state_key(self) -> Optional[str]:
+    def get_state_key(self) -> str | None:
         """Get the state key of this event, or None if it's not a state event"""
         return self._dict.get("state_key")
 
@@ -254,13 +249,13 @@ class EventBase(metaclass=abc.ABCMeta):
 
         return d
 
-    def get(self, key: str, default: Optional[Any] = None) -> Any:
+    def get(self, key: str, default: Any | None = None) -> Any:
         return self._dict.get(key, default)
 
     def get_internal_metadata_dict(self) -> JsonDict:
         return self.internal_metadata.get_dict()
 
-    def get_pdu_json(self, time_now: Optional[int] = None) -> JsonDict:
+    def get_pdu_json(self, time_now: int | None = None) -> JsonDict:
         pdu_json = self.get_dict()
 
         if time_now is not None and "age_ts" in pdu_json["unsigned"]:
@@ -287,19 +282,19 @@ class EventBase(metaclass=abc.ABCMeta):
 
         return template_json
 
-    def __getitem__(self, field: str) -> Optional[Any]:
+    def __getitem__(self, field: str) -> Any | None:
         return self._dict[field]
 
     def __contains__(self, field: str) -> bool:
         return field in self._dict
 
-    def items(self) -> List[Tuple[str, Optional[Any]]]:
+    def items(self) -> list[tuple[str, Any | None]]:
         return list(self._dict.items())
 
     def keys(self) -> Iterable[str]:
         return self._dict.keys()
 
-    def prev_event_ids(self) -> List[str]:
+    def prev_event_ids(self) -> list[str]:
         """Returns the list of prev event IDs. The order matches the order
         specified in the event, though there is no meaning to it.
 
@@ -352,8 +347,8 @@ class FrozenEvent(EventBase):
         self,
         event_dict: JsonDict,
         room_version: RoomVersion,
-        internal_metadata_dict: Optional[JsonDict] = None,
-        rejected_reason: Optional[str] = None,
+        internal_metadata_dict: JsonDict | None = None,
+        rejected_reason: str | None = None,
     ):
         internal_metadata_dict = internal_metadata_dict or {}
 
@@ -404,8 +399,8 @@ class FrozenEventV2(EventBase):
         self,
         event_dict: JsonDict,
         room_version: RoomVersion,
-        internal_metadata_dict: Optional[JsonDict] = None,
-        rejected_reason: Optional[str] = None,
+        internal_metadata_dict: JsonDict | None = None,
+        rejected_reason: str | None = None,
     ):
         internal_metadata_dict = internal_metadata_dict or {}
 
@@ -431,7 +426,7 @@ class FrozenEventV2(EventBase):
         else:
             frozen_dict = event_dict
 
-        self._event_id: Optional[str] = None
+        self._event_id: str | None = None
 
         super().__init__(
             frozen_dict,
@@ -457,7 +452,7 @@ class FrozenEventV2(EventBase):
     def room_id(self) -> str:
         return self._dict["room_id"]
 
-    def prev_event_ids(self) -> List[str]:
+    def prev_event_ids(self) -> list[str]:
         """Returns the list of prev event IDs. The order matches the order
         specified in the event, though there is no meaning to it.
 
@@ -506,8 +501,8 @@ class FrozenEventV4(FrozenEventV3):
         self,
         event_dict: JsonDict,
         room_version: RoomVersion,
-        internal_metadata_dict: Optional[JsonDict] = None,
-        rejected_reason: Optional[str] = None,
+        internal_metadata_dict: JsonDict | None = None,
+        rejected_reason: str | None = None,
     ):
         super().__init__(
             event_dict=event_dict,
@@ -515,7 +510,7 @@ class FrozenEventV4(FrozenEventV3):
             internal_metadata_dict=internal_metadata_dict,
             rejected_reason=rejected_reason,
         )
-        self._room_id: Optional[str] = None
+        self._room_id: str | None = None
 
     @property
     def room_id(self) -> str:
@@ -558,7 +553,7 @@ class FrozenEventV4(FrozenEventV3):
 
 def _event_type_from_format_version(
     format_version: int,
-) -> Type[Union[FrozenEvent, FrozenEventV2, FrozenEventV3]]:
+) -> type[FrozenEvent | FrozenEventV2 | FrozenEventV3]:
     """Returns the python type to use to construct an Event object for the
     given event format version.
 
@@ -584,8 +579,8 @@ def _event_type_from_format_version(
 def make_event_from_dict(
     event_dict: JsonDict,
     room_version: RoomVersion = RoomVersions.V1,
-    internal_metadata_dict: Optional[JsonDict] = None,
-    rejected_reason: Optional[str] = None,
+    internal_metadata_dict: JsonDict | None = None,
+    rejected_reason: str | None = None,
 ) -> EventBase:
     """Construct an EventBase from the given event dict"""
     event_type = _event_type_from_format_version(room_version.event_format)
@@ -602,10 +597,10 @@ class _EventRelation:
     rel_type: str
     # The aggregation key. Will be None if the rel_type is not m.annotation or is
     # not a string.
-    aggregation_key: Optional[str]
+    aggregation_key: str | None
 
 
-def relation_from_event(event: EventBase) -> Optional[_EventRelation]:
+def relation_from_event(event: EventBase) -> _EventRelation | None:
     """
     Attempt to parse relation information an event.
 
@@ -669,4 +664,4 @@ class StrippedStateEvent:
     type: str
     state_key: str
     sender: str
-    content: Dict[str, Any]
+    content: dict[str, Any]
diff --git a/synapse/events/auto_accept_invites.py b/synapse/events/auto_accept_invites.py
index 9e17edd227..4c59f0dffe 100644
--- a/synapse/events/auto_accept_invites.py
+++ b/synapse/events/auto_accept_invites.py
@@ -20,7 +20,7 @@
 #
 import logging
 from http import HTTPStatus
-from typing import Any, Dict, Tuple
+from typing import Any
 
 from synapse.api.constants import AccountDataTypes, EventTypes, Membership
 from synapse.api.errors import SynapseError
@@ -146,7 +146,7 @@ class InviteAutoAccepter:
         # Be careful: we convert the outer frozendict into a dict here,
         # but the contents of the dict are still frozen (tuples in lieu of lists,
         # etc.)
-        dm_map: Dict[str, Tuple[str, ...]] = dict(
+        dm_map: dict[str, tuple[str, ...]] = dict(
             await self._api.account_data_manager.get_global(
                 user_id, AccountDataTypes.DIRECT
             )
diff --git a/synapse/events/builder.py b/synapse/events/builder.py
index 1c9f78c7ca..6a2812109d 100644
--- a/synapse/events/builder.py
+++ b/synapse/events/builder.py
@@ -19,7 +19,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, Any, Dict, List, Optional, Tuple, Union
+from typing import TYPE_CHECKING, Any
 
 import attr
 from signedjson.types import SigningKey
@@ -83,7 +83,7 @@ class EventBuilder:
     room_version: RoomVersion
 
     # MSC4291 makes the room ID == the create event ID. This means the create event has no room_id.
-    room_id: Optional[str]
+    room_id: str | None
     type: str
     sender: str
 
@@ -92,9 +92,9 @@ class EventBuilder:
 
     # These only exist on a subset of events, so they raise AttributeError if
     # someone tries to get them when they don't exist.
-    _state_key: Optional[str] = None
-    _redacts: Optional[str] = None
-    _origin_server_ts: Optional[int] = None
+    _state_key: str | None = None
+    _redacts: str | None = None
+    _origin_server_ts: int | None = None
 
     internal_metadata: EventInternalMetadata = attr.Factory(
         lambda: EventInternalMetadata({})
@@ -125,9 +125,9 @@ class EventBuilder:
 
     async def build(
         self,
-        prev_event_ids: List[str],
-        auth_event_ids: Optional[List[str]],
-        depth: Optional[int] = None,
+        prev_event_ids: list[str],
+        auth_event_ids: list[str] | None,
+        depth: int | None = None,
     ) -> EventBase:
         """Transform into a fully signed and hashed event
 
@@ -205,8 +205,8 @@ class EventBuilder:
 
         format_version = self.room_version.event_format
         # The types of auth/prev events changes between event versions.
-        prev_events: Union[StrCollection, List[Tuple[str, Dict[str, str]]]]
-        auth_events: Union[List[str], List[Tuple[str, Dict[str, str]]]]
+        prev_events: StrCollection | list[tuple[str, dict[str, str]]]
+        auth_events: list[str] | list[tuple[str, dict[str, str]]]
         if format_version == EventFormatVersions.ROOM_V1_V2:
             auth_events = await self._store.add_event_hashes(auth_event_ids)
             prev_events = await self._store.add_event_hashes(prev_event_ids)
@@ -228,7 +228,7 @@ class EventBuilder:
         # the db)
         depth = min(depth, MAX_DEPTH)
 
-        event_dict: Dict[str, Any] = {
+        event_dict: dict[str, Any] = {
             "auth_events": auth_events,
             "prev_events": prev_events,
             "type": self.type,
@@ -327,7 +327,7 @@ def create_local_event_from_event_dict(
     signing_key: SigningKey,
     room_version: RoomVersion,
     event_dict: JsonDict,
-    internal_metadata_dict: Optional[JsonDict] = None,
+    internal_metadata_dict: JsonDict | None = None,
 ) -> EventBase:
     """Takes a fully formed event dict, ensuring that fields like
     `origin_server_ts` have correct values for a locally produced event,
diff --git a/synapse/events/presence_router.py b/synapse/events/presence_router.py
index 9713b141bc..d71d3f8feb 100644
--- a/synapse/events/presence_router.py
+++ b/synapse/events/presence_router.py
@@ -24,13 +24,8 @@ from typing import (
     Any,
     Awaitable,
     Callable,
-    Dict,
     Iterable,
-    List,
-    Optional,
-    Set,
     TypeVar,
-    Union,
 )
 
 from typing_extensions import ParamSpec
@@ -44,10 +39,10 @@ if TYPE_CHECKING:
     from synapse.server import HomeServer
 
 GET_USERS_FOR_STATES_CALLBACK = Callable[
-    [Iterable[UserPresenceState]], Awaitable[Dict[str, Set[UserPresenceState]]]
+    [Iterable[UserPresenceState]], Awaitable[dict[str, set[UserPresenceState]]]
 ]
 # This must either return a set of strings or the constant PresenceRouter.ALL_USERS.
-GET_INTERESTED_USERS_CALLBACK = Callable[[str], Awaitable[Union[Set[str], str]]]
+GET_INTERESTED_USERS_CALLBACK = Callable[[str], Awaitable[set[str] | str]]
 
 logger = logging.getLogger(__name__)
 
@@ -80,8 +75,8 @@ def load_legacy_presence_router(hs: "HomeServer") -> None:
     # All methods that the module provides should be async, but this wasn't enforced
     # in the old module system, so we wrap them if needed
     def async_wrapper(
-        f: Optional[Callable[P, R]],
-    ) -> Optional[Callable[P, Awaitable[R]]]:
+        f: Callable[P, R] | None,
+    ) -> Callable[P, Awaitable[R]] | None:
         # f might be None if the callback isn't implemented by the module. In this
         # case we don't want to register a callback at all so we return None.
         if f is None:
@@ -98,7 +93,7 @@ def load_legacy_presence_router(hs: "HomeServer") -> None:
         return run
 
     # Register the hooks through the module API.
-    hooks: Dict[str, Optional[Callable[..., Any]]] = {
+    hooks: dict[str, Callable[..., Any] | None] = {
         hook: async_wrapper(getattr(presence_router, hook, None))
         for hook in presence_router_methods
     }
@@ -116,13 +111,13 @@ class PresenceRouter:
 
     def __init__(self, hs: "HomeServer"):
         # Initially there are no callbacks
-        self._get_users_for_states_callbacks: List[GET_USERS_FOR_STATES_CALLBACK] = []
-        self._get_interested_users_callbacks: List[GET_INTERESTED_USERS_CALLBACK] = []
+        self._get_users_for_states_callbacks: list[GET_USERS_FOR_STATES_CALLBACK] = []
+        self._get_interested_users_callbacks: list[GET_INTERESTED_USERS_CALLBACK] = []
 
     def register_presence_router_callbacks(
         self,
-        get_users_for_states: Optional[GET_USERS_FOR_STATES_CALLBACK] = None,
-        get_interested_users: Optional[GET_INTERESTED_USERS_CALLBACK] = None,
+        get_users_for_states: GET_USERS_FOR_STATES_CALLBACK | None = None,
+        get_interested_users: GET_INTERESTED_USERS_CALLBACK | None = None,
     ) -> None:
         # PresenceRouter modules are required to implement both of these methods
         # or neither of them as they are assumed to act in a complementary manner
@@ -143,7 +138,7 @@ class PresenceRouter:
     async def get_users_for_states(
         self,
         state_updates: Iterable[UserPresenceState],
-    ) -> Dict[str, Set[UserPresenceState]]:
+    ) -> dict[str, set[UserPresenceState]]:
         """
         Given an iterable of user presence updates, determine where each one
         needs to go.
@@ -161,7 +156,7 @@ class PresenceRouter:
             # Don't include any extra destinations for presence updates
             return {}
 
-        users_for_states: Dict[str, Set[UserPresenceState]] = {}
+        users_for_states: dict[str, set[UserPresenceState]] = {}
         # run all the callbacks for get_users_for_states and combine the results
         for callback in self._get_users_for_states_callbacks:
             try:
@@ -174,7 +169,7 @@ class PresenceRouter:
                 logger.warning("Failed to run module API callback %s: %s", callback, e)
                 continue
 
-            if not isinstance(result, Dict):
+            if not isinstance(result, dict):
                 logger.warning(
                     "Wrong type returned by module API callback %s: %s, expected Dict",
                     callback,
@@ -183,7 +178,7 @@ class PresenceRouter:
                 continue
 
             for key, new_entries in result.items():
-                if not isinstance(new_entries, Set):
+                if not isinstance(new_entries, set):
                     logger.warning(
                         "Wrong type returned by module API callback %s: %s, expected Set",
                         callback,
@@ -194,7 +189,7 @@ class PresenceRouter:
 
         return users_for_states
 
-    async def get_interested_users(self, user_id: str) -> Union[Set[str], str]:
+    async def get_interested_users(self, user_id: str) -> set[str] | str:
         """
         Retrieve a list of users that `user_id` is interested in receiving the
         presence of. This will be in addition to those they share a room with.
@@ -234,7 +229,7 @@ class PresenceRouter:
             if result == PresenceRouter.ALL_USERS:
                 return PresenceRouter.ALL_USERS
 
-            if not isinstance(result, Set):
+            if not isinstance(result, set):
                 logger.warning(
                     "Wrong type returned by module API callback %s: %s, expected set",
                     callback,
diff --git a/synapse/events/snapshot.py b/synapse/events/snapshot.py
index 63551143d8..d7a987d52f 100644
--- a/synapse/events/snapshot.py
+++ b/synapse/events/snapshot.py
@@ -19,7 +19,7 @@
 #
 #
 from abc import ABC, abstractmethod
-from typing import TYPE_CHECKING, Dict, List, Optional, Tuple
+from typing import TYPE_CHECKING, Optional
 
 import attr
 from immutabledict import immutabledict
@@ -51,7 +51,7 @@ class UnpersistedEventContextBase(ABC):
 
     def __init__(self, storage_controller: "StorageControllers"):
         self._storage: "StorageControllers" = storage_controller
-        self.app_service: Optional[ApplicationService] = None
+        self.app_service: ApplicationService | None = None
 
     @abstractmethod
     async def persist(
@@ -133,23 +133,23 @@ class EventContext(UnpersistedEventContextBase):
     """
 
     _storage: "StorageControllers"
-    state_group_deltas: Dict[Tuple[int, int], StateMap[str]]
-    rejected: Optional[str] = None
-    _state_group: Optional[int] = None
-    state_group_before_event: Optional[int] = None
-    _state_delta_due_to_event: Optional[StateMap[str]] = None
-    app_service: Optional[ApplicationService] = None
+    state_group_deltas: dict[tuple[int, int], StateMap[str]]
+    rejected: str | None = None
+    _state_group: int | None = None
+    state_group_before_event: int | None = None
+    _state_delta_due_to_event: StateMap[str] | None = None
+    app_service: ApplicationService | None = None
 
     partial_state: bool = False
 
     @staticmethod
     def with_state(
         storage: "StorageControllers",
-        state_group: Optional[int],
-        state_group_before_event: Optional[int],
-        state_delta_due_to_event: Optional[StateMap[str]],
+        state_group: int | None,
+        state_group_before_event: int | None,
+        state_delta_due_to_event: StateMap[str] | None,
         partial_state: bool,
-        state_group_deltas: Dict[Tuple[int, int], StateMap[str]],
+        state_group_deltas: dict[tuple[int, int], StateMap[str]],
     ) -> "EventContext":
         return EventContext(
             storage=storage,
@@ -227,7 +227,7 @@ class EventContext(UnpersistedEventContextBase):
         return context
 
     @property
-    def state_group(self) -> Optional[int]:
+    def state_group(self) -> int | None:
         """The ID of the state group for this event.
 
         Note that state events are persisted with a state group which includes the new
@@ -306,7 +306,7 @@ class EventContext(UnpersistedEventContextBase):
         )
 
 
-EventPersistencePair = Tuple[EventBase, EventContext]
+EventPersistencePair = tuple[EventBase, EventContext]
 """
 The combination of an event to be persisted and its context.
 """
@@ -354,22 +354,22 @@ class UnpersistedEventContext(UnpersistedEventContextBase):
     """
 
     _storage: "StorageControllers"
-    state_group_before_event: Optional[int]
-    state_group_after_event: Optional[int]
-    state_delta_due_to_event: Optional[StateMap[str]]
-    prev_group_for_state_group_before_event: Optional[int]
-    delta_ids_to_state_group_before_event: Optional[StateMap[str]]
+    state_group_before_event: int | None
+    state_group_after_event: int | None
+    state_delta_due_to_event: StateMap[str] | None
+    prev_group_for_state_group_before_event: int | None
+    delta_ids_to_state_group_before_event: StateMap[str] | None
     partial_state: bool
-    state_map_before_event: Optional[StateMap[str]] = None
+    state_map_before_event: StateMap[str] | None = None
 
     @classmethod
     async def batch_persist_unpersisted_contexts(
         cls,
-        events_and_context: List[Tuple[EventBase, "UnpersistedEventContextBase"]],
+        events_and_context: list[tuple[EventBase, "UnpersistedEventContextBase"]],
         room_id: str,
         last_known_state_group: int,
         datastore: "StateGroupDataStore",
-    ) -> List[EventPersistencePair]:
+    ) -> list[EventPersistencePair]:
         """
         Takes a list of events and their associated unpersisted contexts and persists
         the unpersisted contexts, returning a list of events and persisted contexts.
@@ -472,7 +472,7 @@ class UnpersistedEventContext(UnpersistedEventContextBase):
             partial_state=self.partial_state,
         )
 
-    def _build_state_group_deltas(self) -> Dict[Tuple[int, int], StateMap]:
+    def _build_state_group_deltas(self) -> dict[tuple[int, int], StateMap]:
         """
         Collect deltas between the state groups associated with this context
         """
@@ -510,8 +510,8 @@ class UnpersistedEventContext(UnpersistedEventContextBase):
 
 
 def _encode_state_group_delta(
-    state_group_delta: Dict[Tuple[int, int], StateMap[str]],
-) -> List[Tuple[int, int, Optional[List[Tuple[str, str, str]]]]]:
+    state_group_delta: dict[tuple[int, int], StateMap[str]],
+) -> list[tuple[int, int, list[tuple[str, str, str]] | None]]:
     if not state_group_delta:
         return []
 
@@ -523,8 +523,8 @@ def _encode_state_group_delta(
 
 
 def _decode_state_group_delta(
-    input: List[Tuple[int, int, List[Tuple[str, str, str]]]],
-) -> Dict[Tuple[int, int], StateMap[str]]:
+    input: list[tuple[int, int, list[tuple[str, str, str]]]],
+) -> dict[tuple[int, int], StateMap[str]]:
     if not input:
         return {}
 
@@ -538,8 +538,8 @@ def _decode_state_group_delta(
 
 
 def _encode_state_dict(
-    state_dict: Optional[StateMap[str]],
-) -> Optional[List[Tuple[str, str, str]]]:
+    state_dict: StateMap[str] | None,
+) -> list[tuple[str, str, str]] | None:
     """Since dicts of (type, state_key) -> event_id cannot be serialized in
     JSON we need to convert them to a form that can.
     """
@@ -550,8 +550,8 @@ def _encode_state_dict(
 
 
 def _decode_state_dict(
-    input: Optional[List[Tuple[str, str, str]]],
-) -> Optional[StateMap[str]]:
+    input: list[tuple[str, str, str]] | None,
+) -> StateMap[str] | None:
     """Decodes a state dict encoded using `_encode_state_dict` above"""
     if input is None:
         return None
diff --git a/synapse/events/utils.py b/synapse/events/utils.py
index 942072cf84..b79a68f589 100644
--- a/synapse/events/utils.py
+++ b/synapse/events/utils.py
@@ -27,13 +27,9 @@ from typing import (
     Awaitable,
     Callable,
     Collection,
-    Dict,
-    List,
     Mapping,
     Match,
     MutableMapping,
-    Optional,
-    Union,
 )
 
 import attr
@@ -239,7 +235,7 @@ def prune_event_dict(room_version: RoomVersion, event_dict: JsonDict) -> JsonDic
     return allowed_fields
 
 
-def _copy_field(src: JsonDict, dst: JsonDict, field: List[str]) -> None:
+def _copy_field(src: JsonDict, dst: JsonDict, field: list[str]) -> None:
     """Copy the field in 'src' to 'dst'.
 
     For example, if src={"foo":{"bar":5}} and dst={}, and field=["foo","bar"]
@@ -292,7 +288,7 @@ def _escape_slash(m: Match[str]) -> str:
     return m.group(0)
 
 
-def _split_field(field: str) -> List[str]:
+def _split_field(field: str) -> list[str]:
     """
     Splits strings on unescaped dots and removes escaping.
 
@@ -333,7 +329,7 @@ def _split_field(field: str) -> List[str]:
     return result
 
 
-def only_fields(dictionary: JsonDict, fields: List[str]) -> JsonDict:
+def only_fields(dictionary: JsonDict, fields: list[str]) -> JsonDict:
     """Return a new dict with only the fields in 'dictionary' which are present
     in 'fields'.
 
@@ -417,9 +413,9 @@ class SerializeEventConfig:
     event_format: Callable[[JsonDict], JsonDict] = format_event_for_client_v1
     # The entity that requested the event. This is used to determine whether to include
     # the transaction_id in the unsigned section of the event.
-    requester: Optional[Requester] = None
+    requester: Requester | None = None
     # List of event fields to include. If empty, all fields will be returned.
-    only_event_fields: Optional[List[str]] = None
+    only_event_fields: list[str] | None = None
     # Some events can have stripped room state stored in the `unsigned` field.
     # This is required for invite and knock functionality. If this option is
     # False, that state will be removed from the event before it is returned.
@@ -441,7 +437,7 @@ def make_config_for_admin(existing: SerializeEventConfig) -> SerializeEventConfi
 
 
 def serialize_event(
-    e: Union[JsonDict, EventBase],
+    e: JsonDict | EventBase,
     time_now_ms: int,
     *,
     config: SerializeEventConfig = _DEFAULT_SERIALIZE_EVENT_CONFIG,
@@ -482,7 +478,7 @@ def serialize_event(
     # If we have a txn_id saved in the internal_metadata, we should include it in the
     # unsigned section of the event if it was sent by the same session as the one
     # requesting the event.
-    txn_id: Optional[str] = getattr(e.internal_metadata, "txn_id", None)
+    txn_id: str | None = getattr(e.internal_metadata, "txn_id", None)
     if (
         txn_id is not None
         and config.requester is not None
@@ -492,7 +488,7 @@ def serialize_event(
         # this includes old events as well as those created by appservice, guests,
         # or with tokens minted with the admin API. For those events, fallback
         # to using the access token instead.
-        event_device_id: Optional[str] = getattr(e.internal_metadata, "device_id", None)
+        event_device_id: str | None = getattr(e.internal_metadata, "device_id", None)
         if event_device_id is not None:
             if event_device_id == config.requester.device_id:
                 d["unsigned"]["transaction_id"] = txn_id
@@ -506,9 +502,7 @@ def serialize_event(
             #
             # For guests and appservice users, we can't check the access token ID
             # so assume it is the same session.
-            event_token_id: Optional[int] = getattr(
-                e.internal_metadata, "token_id", None
-            )
+            event_token_id: int | None = getattr(e.internal_metadata, "token_id", None)
             if (
                 (
                     event_token_id is not None
@@ -573,17 +567,17 @@ class EventClientSerializer:
     def __init__(self, hs: "HomeServer") -> None:
         self._store = hs.get_datastores().main
         self._auth = hs.get_auth()
-        self._add_extra_fields_to_unsigned_client_event_callbacks: List[
+        self._add_extra_fields_to_unsigned_client_event_callbacks: list[
             ADD_EXTRA_FIELDS_TO_UNSIGNED_CLIENT_EVENT_CALLBACK
         ] = []
 
     async def serialize_event(
         self,
-        event: Union[JsonDict, EventBase],
+        event: JsonDict | EventBase,
         time_now: int,
         *,
         config: SerializeEventConfig = _DEFAULT_SERIALIZE_EVENT_CONFIG,
-        bundle_aggregations: Optional[Dict[str, "BundledAggregations"]] = None,
+        bundle_aggregations: dict[str, "BundledAggregations"] | None = None,
     ) -> JsonDict:
         """Serializes a single event.
 
@@ -641,7 +635,7 @@ class EventClientSerializer:
         event: EventBase,
         time_now: int,
         config: SerializeEventConfig,
-        bundled_aggregations: Dict[str, "BundledAggregations"],
+        bundled_aggregations: dict[str, "BundledAggregations"],
         serialized_event: JsonDict,
     ) -> None:
         """Potentially injects bundled aggregations into the unsigned portion of the serialized event.
@@ -714,12 +708,12 @@ class EventClientSerializer:
     @trace
     async def serialize_events(
         self,
-        events: Collection[Union[JsonDict, EventBase]],
+        events: Collection[JsonDict | EventBase],
         time_now: int,
         *,
         config: SerializeEventConfig = _DEFAULT_SERIALIZE_EVENT_CONFIG,
-        bundle_aggregations: Optional[Dict[str, "BundledAggregations"]] = None,
-    ) -> List[JsonDict]:
+        bundle_aggregations: dict[str, "BundledAggregations"] | None = None,
+    ) -> list[JsonDict]:
         """Serializes multiple events.
 
         Args:
@@ -757,13 +751,13 @@ class EventClientSerializer:
         self._add_extra_fields_to_unsigned_client_event_callbacks.append(callback)
 
 
-_PowerLevel = Union[str, int]
-PowerLevelsContent = Mapping[str, Union[_PowerLevel, Mapping[str, _PowerLevel]]]
+_PowerLevel = str | int
+PowerLevelsContent = Mapping[str, _PowerLevel | Mapping[str, _PowerLevel]]
 
 
 def copy_and_fixup_power_levels_contents(
     old_power_levels: PowerLevelsContent,
-) -> Dict[str, Union[int, Dict[str, int]]]:
+) -> dict[str, int | dict[str, int]]:
     """Copy the content of a power_levels event, unfreezing immutabledicts along the way.
 
     We accept as input power level values which are strings, provided they represent an
@@ -779,11 +773,11 @@ def copy_and_fixup_power_levels_contents(
     if not isinstance(old_power_levels, collections.abc.Mapping):
         raise TypeError("Not a valid power-levels content: %r" % (old_power_levels,))
 
-    power_levels: Dict[str, Union[int, Dict[str, int]]] = {}
+    power_levels: dict[str, int | dict[str, int]] = {}
 
     for k, v in old_power_levels.items():
         if isinstance(v, collections.abc.Mapping):
-            h: Dict[str, int] = {}
+            h: dict[str, int] = {}
             power_levels[k] = h
             for k1, v1 in v.items():
                 _copy_power_level_value_as_integer(v1, h, k1)
@@ -903,7 +897,7 @@ def strip_event(event: EventBase) -> JsonDict:
     }
 
 
-def parse_stripped_state_event(raw_stripped_event: Any) -> Optional[StrippedStateEvent]:
+def parse_stripped_state_event(raw_stripped_event: Any) -> StrippedStateEvent | None:
     """
     Given a raw value from an event's `unsigned` field, attempt to parse it into a
     `StrippedStateEvent`.
diff --git a/synapse/events/validator.py b/synapse/events/validator.py
index 4d9ba15829..b27f8a942a 100644
--- a/synapse/events/validator.py
+++ b/synapse/events/validator.py
@@ -19,11 +19,11 @@
 #
 #
 import collections.abc
-from typing import List, Type, Union, cast
+from typing import cast
 
 import jsonschema
+from pydantic import Field, StrictBool, StrictStr
 
-from synapse._pydantic_compat import Field, StrictBool, StrictStr
 from synapse.api.constants import (
     MAX_ALIAS_LENGTH,
     EventContentFields,
@@ -177,7 +177,7 @@ class EventValidator:
                 errcode=Codes.BAD_JSON,
             )
 
-    def validate_builder(self, event: Union[EventBase, EventBuilder]) -> None:
+    def validate_builder(self, event: EventBase | EventBuilder) -> None:
         """Validates that the builder/event has roughly the right format. Only
         checks values that we expect a proto event to have, rather than all the
         fields an event would have
@@ -249,7 +249,7 @@ class EventValidator:
             if not isinstance(d[s], str):
                 raise SynapseError(400, "'%s' not a string type" % (s,))
 
-    def _ensure_state_event(self, event: Union[EventBase, EventBuilder]) -> None:
+    def _ensure_state_event(self, event: EventBase | EventBuilder) -> None:
         if not event.is_state():
             raise SynapseError(400, "'%s' must be state events" % (event.type,))
 
@@ -283,13 +283,13 @@ POWER_LEVELS_SCHEMA = {
 
 
 class Mentions(RequestBodyModel):
-    user_ids: List[StrictStr] = Field(default_factory=list)
+    user_ids: list[StrictStr] = Field(default_factory=list)
     room: StrictBool = False
 
 
 # This could return something newer than Draft 7, but that's the current "latest"
 # validator.
-def _create_validator(schema: JsonDict) -> Type[jsonschema.Draft7Validator]:
+def _create_validator(schema: JsonDict) -> type[jsonschema.Draft7Validator]:
     validator = jsonschema.validators.validator_for(schema)
 
     # by default jsonschema does not consider a immutabledict to be an object so
diff --git a/synapse/federation/federation_base.py b/synapse/federation/federation_base.py
index a1c9c286ac..04ba5b86db 100644
--- a/synapse/federation/federation_base.py
+++ b/synapse/federation/federation_base.py
@@ -20,7 +20,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, Awaitable, Callable, List, Optional, Sequence
+from typing import TYPE_CHECKING, Awaitable, Callable, Sequence
 
 from synapse.api.constants import MAX_DEPTH, EventContentFields, EventTypes, Membership
 from synapse.api.errors import Codes, SynapseError
@@ -67,7 +67,7 @@ class FederationBase:
 
         # We need to define this lazily otherwise we get a cyclic dependency.
         # self._policy_handler = hs.get_room_policy_handler()
-        self._policy_handler: Optional[RoomPolicyHandler] = None
+        self._policy_handler: RoomPolicyHandler | None = None
 
     def _lazily_get_policy_handler(self) -> RoomPolicyHandler:
         """Lazily get the room policy handler.
@@ -88,9 +88,8 @@ class FederationBase:
         self,
         room_version: RoomVersion,
         pdu: EventBase,
-        record_failure_callback: Optional[
-            Callable[[EventBase, str], Awaitable[None]]
-        ] = None,
+        record_failure_callback: Callable[[EventBase, str], Awaitable[None]]
+        | None = None,
     ) -> EventBase:
         """Checks that event is correctly signed by the sending server.
 
@@ -305,7 +304,7 @@ def _is_invite_via_3pid(event: EventBase) -> bool:
 
 def parse_events_from_pdu_json(
     pdus_json: Sequence[JsonDict], room_version: RoomVersion
-) -> List[EventBase]:
+) -> list[EventBase]:
     return [
         event_from_pdu_json(pdu_json, room_version)
         for pdu_json in filter_pdus_for_valid_depth(pdus_json)
diff --git a/synapse/federation/federation_client.py b/synapse/federation/federation_client.py
index 41595043d1..4110a90ed6 100644
--- a/synapse/federation/federation_client.py
+++ b/synapse/federation/federation_client.py
@@ -32,15 +32,11 @@ from typing import (
     Callable,
     Collection,
     Container,
-    Dict,
     Iterable,
-    List,
     Mapping,
     Optional,
     Sequence,
-    Tuple,
     TypeVar,
-    Union,
 )
 
 import attr
@@ -120,8 +116,8 @@ class SendJoinResult:
     event: EventBase
     # A string giving the server the event was sent to.
     origin: str
-    state: List[EventBase]
-    auth_chain: List[EventBase]
+    state: list[EventBase]
+    auth_chain: list[EventBase]
 
     # True if 'state' elides non-critical membership events
     partial_state: bool
@@ -135,7 +131,7 @@ class FederationClient(FederationBase):
     def __init__(self, hs: "HomeServer"):
         super().__init__(hs)
 
-        self.pdu_destination_tried: Dict[str, Dict[str, int]] = {}
+        self.pdu_destination_tried: dict[str, dict[str, int]] = {}
         self._clock.looping_call(self._clear_tried_cache, 60 * 1000)
         self.state = hs.get_state_handler()
         self.transport_layer = hs.get_federation_transport_client()
@@ -145,9 +141,10 @@ class FederationClient(FederationBase):
 
         # Cache mapping `event_id` to a tuple of the event itself and the `pull_origin`
         # (which server we pulled the event from)
-        self._get_pdu_cache: ExpiringCache[str, Tuple[EventBase, str]] = ExpiringCache(
+        self._get_pdu_cache: ExpiringCache[str, tuple[EventBase, str]] = ExpiringCache(
             cache_name="get_pdu_cache",
             server_name=self.server_name,
+            hs=self.hs,
             clock=self._clock,
             max_len=1000,
             expiry_ms=120 * 1000,
@@ -162,11 +159,12 @@ class FederationClient(FederationBase):
         # It is a map of (room ID, suggested-only) -> the response of
         # get_room_hierarchy.
         self._get_room_hierarchy_cache: ExpiringCache[
-            Tuple[str, bool],
-            Tuple[JsonDict, Sequence[JsonDict], Sequence[JsonDict], Sequence[str]],
+            tuple[str, bool],
+            tuple[JsonDict, Sequence[JsonDict], Sequence[JsonDict], Sequence[str]],
         ] = ExpiringCache(
             cache_name="get_room_hierarchy_cache",
             server_name=self.server_name,
+            hs=self.hs,
             clock=self._clock,
             max_len=1000,
             expiry_ms=5 * 60 * 1000,
@@ -263,8 +261,8 @@ class FederationClient(FederationBase):
         self,
         user: UserID,
         destination: str,
-        query: Dict[str, Dict[str, Dict[str, int]]],
-        timeout: Optional[int],
+        query: dict[str, dict[str, dict[str, int]]],
+        timeout: int | None,
     ) -> JsonDict:
         """Claims one-time keys for a device hosted on a remote server.
 
@@ -283,8 +281,8 @@ class FederationClient(FederationBase):
 
         # Convert the query with counts into a stable and unstable query and check
         # if attempting to claim more than 1 OTK.
-        content: Dict[str, Dict[str, str]] = {}
-        unstable_content: Dict[str, Dict[str, List[str]]] = {}
+        content: dict[str, dict[str, str]] = {}
+        unstable_content: dict[str, dict[str, list[str]]] = {}
         use_unstable = False
         for user_id, one_time_keys in query.items():
             for device_id, algorithms in one_time_keys.items():
@@ -335,7 +333,7 @@ class FederationClient(FederationBase):
     @tag_args
     async def backfill(
         self, dest: str, room_id: str, limit: int, extremities: Collection[str]
-    ) -> Optional[List[EventBase]]:
+    ) -> list[EventBase] | None:
         """Requests some more historic PDUs for the given room from the
         given destination server.
 
@@ -382,8 +380,8 @@ class FederationClient(FederationBase):
         destination: str,
         event_id: str,
         room_version: RoomVersion,
-        timeout: Optional[int] = None,
-    ) -> Optional[EventBase]:
+        timeout: int | None = None,
+    ) -> EventBase | None:
         """Requests the PDU with given origin and ID from the remote home
         server. Does not have any caching or rate limiting!
 
@@ -442,7 +440,7 @@ class FederationClient(FederationBase):
     @trace
     @tag_args
     async def get_pdu_policy_recommendation(
-        self, destination: str, pdu: EventBase, timeout: Optional[int] = None
+        self, destination: str, pdu: EventBase, timeout: int | None = None
     ) -> str:
         """Requests that the destination server (typically a policy server)
         check the event and return its recommendation on how to handle the
@@ -498,8 +496,8 @@ class FederationClient(FederationBase):
     @trace
     @tag_args
     async def ask_policy_server_to_sign_event(
-        self, destination: str, pdu: EventBase, timeout: Optional[int] = None
-    ) -> Optional[JsonDict]:
+        self, destination: str, pdu: EventBase, timeout: int | None = None
+    ) -> JsonDict | None:
         """Requests that the destination server (typically a policy server)
         sign the event as not spam.
 
@@ -539,8 +537,8 @@ class FederationClient(FederationBase):
         destinations: Collection[str],
         event_id: str,
         room_version: RoomVersion,
-        timeout: Optional[int] = None,
-    ) -> Optional[PulledPduInfo]:
+        timeout: int | None = None,
+    ) -> PulledPduInfo | None:
         """Requests the PDU with given origin and ID from the remote home
         servers.
 
@@ -660,7 +658,7 @@ class FederationClient(FederationBase):
     @tag_args
     async def get_room_state_ids(
         self, destination: str, room_id: str, event_id: str
-    ) -> Tuple[List[str], List[str]]:
+    ) -> tuple[list[str], list[str]]:
         """Calls the /state_ids endpoint to fetch the state at a particular point
         in the room, and the auth events for the given event
 
@@ -709,7 +707,7 @@ class FederationClient(FederationBase):
         room_id: str,
         event_id: str,
         room_version: RoomVersion,
-    ) -> Tuple[List[EventBase], List[EventBase]]:
+    ) -> tuple[list[EventBase], list[EventBase]]:
         """Calls the /state endpoint to fetch the state at a particular point
         in the room.
 
@@ -770,7 +768,7 @@ class FederationClient(FederationBase):
         origin: str,
         pdus: Collection[EventBase],
         room_version: RoomVersion,
-    ) -> List[EventBase]:
+    ) -> list[EventBase]:
         """
         Checks the signatures and hashes of a list of pulled events we got from
         federation and records any signature failures as failed pull attempts.
@@ -804,7 +802,7 @@ class FederationClient(FederationBase):
         # We limit how many PDUs we check at once, as if we try to do hundreds
         # of thousands of PDUs at once we see large memory spikes.
 
-        valid_pdus: List[EventBase] = []
+        valid_pdus: list[EventBase] = []
 
         async def _record_failure_callback(event: EventBase, cause: str) -> None:
             await self.store.record_event_failed_pull_attempt(
@@ -833,10 +831,9 @@ class FederationClient(FederationBase):
         pdu: EventBase,
         origin: str,
         room_version: RoomVersion,
-        record_failure_callback: Optional[
-            Callable[[EventBase, str], Awaitable[None]]
-        ] = None,
-    ) -> Optional[EventBase]:
+        record_failure_callback: Callable[[EventBase, str], Awaitable[None]]
+        | None = None,
+    ) -> EventBase | None:
         """Takes a PDU and checks its signatures and hashes.
 
         If the PDU fails its signature check then we check if we have it in the
@@ -914,7 +911,7 @@ class FederationClient(FederationBase):
 
     async def get_event_auth(
         self, destination: str, room_id: str, event_id: str
-    ) -> List[EventBase]:
+    ) -> list[EventBase]:
         res = await self.transport_layer.get_event_auth(destination, room_id, event_id)
 
         room_version = await self.store.get_room_version(room_id)
@@ -932,7 +929,7 @@ class FederationClient(FederationBase):
         description: str,
         destinations: Iterable[str],
         callback: Callable[[str], Awaitable[T]],
-        failover_errcodes: Optional[Container[str]] = None,
+        failover_errcodes: Container[str] | None = None,
         failover_on_unknown_endpoint: bool = False,
     ) -> T:
         """Try an operation on a series of servers, until it succeeds
@@ -1047,8 +1044,8 @@ class FederationClient(FederationBase):
         user_id: str,
         membership: str,
         content: dict,
-        params: Optional[Mapping[str, Union[str, Iterable[str]]]],
-    ) -> Tuple[str, EventBase, RoomVersion]:
+        params: Mapping[str, str | Iterable[str]] | None,
+    ) -> tuple[str, EventBase, RoomVersion]:
         """
         Creates an m.room.member event, with context, without participating in the room.
 
@@ -1090,7 +1087,7 @@ class FederationClient(FederationBase):
                 % (membership, ",".join(valid_memberships))
             )
 
-        async def send_request(destination: str) -> Tuple[str, EventBase, RoomVersion]:
+        async def send_request(destination: str) -> tuple[str, EventBase, RoomVersion]:
             ret = await self.transport_layer.make_membership_event(
                 destination, room_id, user_id, membership, params
             )
@@ -1235,7 +1232,7 @@ class FederationClient(FederationBase):
             # We now go and check the signatures and hashes for the event. Note
             # that we limit how many events we process at a time to keep the
             # memory overhead from exploding.
-            valid_pdus_map: Dict[str, EventBase] = {}
+            valid_pdus_map: dict[str, EventBase] = {}
 
             async def _execute(pdu: EventBase) -> None:
                 valid_pdu = await self._check_sigs_and_hash_and_fetch_one(
@@ -1505,7 +1502,7 @@ class FederationClient(FederationBase):
         # content.
         return resp[1]
 
-    async def send_knock(self, destinations: List[str], pdu: EventBase) -> JsonDict:
+    async def send_knock(self, destinations: list[str], pdu: EventBase) -> JsonDict:
         """Attempts to send a knock event to a given list of servers. Iterates
         through the list until one attempt succeeds.
 
@@ -1564,11 +1561,11 @@ class FederationClient(FederationBase):
     async def get_public_rooms(
         self,
         remote_server: str,
-        limit: Optional[int] = None,
-        since_token: Optional[str] = None,
-        search_filter: Optional[Dict] = None,
+        limit: int | None = None,
+        since_token: str | None = None,
+        search_filter: dict | None = None,
         include_all_networks: bool = False,
-        third_party_instance_id: Optional[str] = None,
+        third_party_instance_id: str | None = None,
     ) -> JsonDict:
         """Get the list of public rooms from a remote homeserver
 
@@ -1610,7 +1607,7 @@ class FederationClient(FederationBase):
         limit: int,
         min_depth: int,
         timeout: int,
-    ) -> List[EventBase]:
+    ) -> list[EventBase]:
         """Tries to fetch events we are missing. This is called when we receive
         an event without having received all of its ancestors.
 
@@ -1677,7 +1674,7 @@ class FederationClient(FederationBase):
 
     async def get_room_complexity(
         self, destination: str, room_id: str
-    ) -> Optional[JsonDict]:
+    ) -> JsonDict | None:
         """
         Fetch the complexity of a remote room from another server.
 
@@ -1716,7 +1713,7 @@ class FederationClient(FederationBase):
         destinations: Iterable[str],
         room_id: str,
         suggested_only: bool,
-    ) -> Tuple[JsonDict, Sequence[JsonDict], Sequence[JsonDict], Sequence[str]]:
+    ) -> tuple[JsonDict, Sequence[JsonDict], Sequence[JsonDict], Sequence[str]]:
         """
         Call other servers to get a hierarchy of the given room.
 
@@ -1747,7 +1744,7 @@ class FederationClient(FederationBase):
 
         async def send_request(
             destination: str,
-        ) -> Tuple[JsonDict, Sequence[JsonDict], Sequence[JsonDict], Sequence[str]]:
+        ) -> tuple[JsonDict, Sequence[JsonDict], Sequence[JsonDict], Sequence[str]]:
             try:
                 res = await self.transport_layer.get_room_hierarchy(
                     destination=destination,
@@ -1922,8 +1919,8 @@ class FederationClient(FederationBase):
             raise InvalidResponseError(str(e))
 
     async def get_account_status(
-        self, destination: str, user_ids: List[str]
-    ) -> Tuple[JsonDict, List[str]]:
+        self, destination: str, user_ids: list[str]
+    ) -> tuple[JsonDict, list[str]]:
         """Retrieves account statuses for a given list of users on a given remote
         homeserver.
 
@@ -1988,10 +1985,10 @@ class FederationClient(FederationBase):
         max_timeout_ms: int,
         download_ratelimiter: Ratelimiter,
         ip_address: str,
-    ) -> Union[
-        Tuple[int, Dict[bytes, List[bytes]], bytes],
-        Tuple[int, Dict[bytes, List[bytes]]],
-    ]:
+    ) -> (
+        tuple[int, dict[bytes, list[bytes]], bytes]
+        | tuple[int, dict[bytes, list[bytes]]]
+    ):
         try:
             return await self.transport_layer.federation_download_media(
                 destination,
@@ -2034,7 +2031,7 @@ class FederationClient(FederationBase):
         max_timeout_ms: int,
         download_ratelimiter: Ratelimiter,
         ip_address: str,
-    ) -> Tuple[int, Dict[bytes, List[bytes]]]:
+    ) -> tuple[int, dict[bytes, list[bytes]]]:
         try:
             return await self.transport_layer.download_media_v3(
                 destination,
diff --git a/synapse/federation/federation_server.py b/synapse/federation/federation_server.py
index e7da8fda0d..34abac1cec 100644
--- a/synapse/federation/federation_server.py
+++ b/synapse/federation/federation_server.py
@@ -27,12 +27,7 @@ from typing import (
     Awaitable,
     Callable,
     Collection,
-    Dict,
-    List,
     Mapping,
-    Optional,
-    Tuple,
-    Union,
 )
 
 from prometheus_client import Counter, Gauge, Histogram
@@ -163,10 +158,10 @@ class FederationServer(FederationBase):
 
         # origins that we are currently processing a transaction from.
         # a dict from origin to txn id.
-        self._active_transactions: Dict[str, str] = {}
+        self._active_transactions: dict[str, str] = {}
 
         # We cache results for transaction with the same ID
-        self._transaction_resp_cache: ResponseCache[Tuple[str, str]] = ResponseCache(
+        self._transaction_resp_cache: ResponseCache[tuple[str, str]] = ResponseCache(
             clock=hs.get_clock(),
             name="fed_txn_handler",
             server_name=self.server_name,
@@ -179,15 +174,13 @@ class FederationServer(FederationBase):
 
         # We cache responses to state queries, as they take a while and often
         # come in waves.
-        self._state_resp_cache: ResponseCache[Tuple[str, Optional[str]]] = (
-            ResponseCache(
-                clock=hs.get_clock(),
-                name="state_resp",
-                server_name=self.server_name,
-                timeout_ms=30000,
-            )
+        self._state_resp_cache: ResponseCache[tuple[str, str | None]] = ResponseCache(
+            clock=hs.get_clock(),
+            name="state_resp",
+            server_name=self.server_name,
+            timeout_ms=30000,
         )
-        self._state_ids_resp_cache: ResponseCache[Tuple[str, str]] = ResponseCache(
+        self._state_ids_resp_cache: ResponseCache[tuple[str, str]] = ResponseCache(
             clock=hs.get_clock(),
             name="state_ids_resp",
             server_name=self.server_name,
@@ -236,8 +229,8 @@ class FederationServer(FederationBase):
             await self._clock.sleep(random.uniform(0, 0.1))
 
     async def on_backfill_request(
-        self, origin: str, room_id: str, versions: List[str], limit: int
-    ) -> Tuple[int, Dict[str, Any]]:
+        self, origin: str, room_id: str, versions: list[str], limit: int
+    ) -> tuple[int, dict[str, Any]]:
         async with self._server_linearizer.queue((origin, room_id)):
             origin_host, _ = parse_server_name(origin)
             await self.check_server_matches_acl(origin_host, room_id)
@@ -252,7 +245,7 @@ class FederationServer(FederationBase):
 
     async def on_timestamp_to_event_request(
         self, origin: str, room_id: str, timestamp: int, direction: Direction
-    ) -> Tuple[int, Dict[str, Any]]:
+    ) -> tuple[int, dict[str, Any]]:
         """When we receive a federated `/timestamp_to_event` request,
         handle all of the logic for validating and fetching the event.
 
@@ -298,7 +291,7 @@ class FederationServer(FederationBase):
         transaction_id: str,
         destination: str,
         transaction_data: JsonDict,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         # If we receive a transaction we should make sure that kick off handling
         # any old events in the staging area.
         if not self._started_handling_of_staged_events:
@@ -365,7 +358,7 @@ class FederationServer(FederationBase):
 
     async def _on_incoming_transaction_inner(
         self, origin: str, transaction: Transaction, request_time: int
-    ) -> Tuple[int, Dict[str, Any]]:
+    ) -> tuple[int, dict[str, Any]]:
         # CRITICAL SECTION: the first thing we must do (before awaiting) is
         # add an entry to _active_transactions.
         assert origin not in self._active_transactions
@@ -381,7 +374,7 @@ class FederationServer(FederationBase):
 
     async def _handle_incoming_transaction(
         self, origin: str, transaction: Transaction, request_time: int
-    ) -> Tuple[int, Dict[str, Any]]:
+    ) -> tuple[int, dict[str, Any]]:
         """Process an incoming transaction and return the HTTP response
 
         Args:
@@ -429,7 +422,7 @@ class FederationServer(FederationBase):
 
     async def _handle_pdus_in_txn(
         self, origin: str, transaction: Transaction, request_time: int
-    ) -> Dict[str, dict]:
+    ) -> dict[str, dict]:
         """Process the PDUs in a received transaction.
 
         Args:
@@ -448,7 +441,7 @@ class FederationServer(FederationBase):
 
         origin_host, _ = parse_server_name(origin)
 
-        pdus_by_room: Dict[str, List[EventBase]] = {}
+        pdus_by_room: dict[str, list[EventBase]] = {}
 
         newest_pdu_ts = 0
 
@@ -601,7 +594,7 @@ class FederationServer(FederationBase):
 
     async def on_room_state_request(
         self, origin: str, room_id: str, event_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await self._event_auth_handler.assert_host_in_room(room_id, origin)
         origin_host, _ = parse_server_name(origin)
         await self.check_server_matches_acl(origin_host, room_id)
@@ -625,7 +618,7 @@ class FederationServer(FederationBase):
     @tag_args
     async def on_state_ids_request(
         self, origin: str, room_id: str, event_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         if not event_id:
             raise NotImplementedError("Specify an event")
 
@@ -653,7 +646,7 @@ class FederationServer(FederationBase):
 
     async def _on_context_state_request_compute(
         self, room_id: str, event_id: str
-    ) -> Dict[str, list]:
+    ) -> dict[str, list]:
         pdus: Collection[EventBase]
         event_ids = await self.handler.get_state_ids_for_pdu(room_id, event_id)
         pdus = await self.store.get_events_as_list(event_ids)
@@ -669,7 +662,7 @@ class FederationServer(FederationBase):
 
     async def on_pdu_request(
         self, origin: str, event_id: str
-    ) -> Tuple[int, Union[JsonDict, str]]:
+    ) -> tuple[int, JsonDict | str]:
         pdu = await self.handler.get_persisted_pdu(origin, event_id)
 
         if pdu:
@@ -678,8 +671,8 @@ class FederationServer(FederationBase):
             return 404, ""
 
     async def on_query_request(
-        self, query_type: str, args: Dict[str, str]
-    ) -> Tuple[int, Dict[str, Any]]:
+        self, query_type: str, args: dict[str, str]
+    ) -> tuple[int, dict[str, Any]]:
         received_queries_counter.labels(
             type=query_type,
             **{SERVER_NAME_LABEL: self.server_name},
@@ -688,8 +681,8 @@ class FederationServer(FederationBase):
         return 200, resp
 
     async def on_make_join_request(
-        self, origin: str, room_id: str, user_id: str, supported_versions: List[str]
-    ) -> Dict[str, Any]:
+        self, origin: str, room_id: str, user_id: str, supported_versions: list[str]
+    ) -> dict[str, Any]:
         origin_host, _ = parse_server_name(origin)
         await self.check_server_matches_acl(origin_host, room_id)
 
@@ -714,7 +707,7 @@ class FederationServer(FederationBase):
 
     async def on_invite_request(
         self, origin: str, content: JsonDict, room_version_id: str
-    ) -> Dict[str, Any]:
+    ) -> dict[str, Any]:
         room_version = KNOWN_ROOM_VERSIONS.get(room_version_id)
         if not room_version:
             raise SynapseError(
@@ -748,7 +741,7 @@ class FederationServer(FederationBase):
         content: JsonDict,
         room_id: str,
         caller_supports_partial_state: bool = False,
-    ) -> Dict[str, Any]:
+    ) -> dict[str, Any]:
         set_tag(
             SynapseTags.SEND_JOIN_RESPONSE_IS_PARTIAL_STATE,
             caller_supports_partial_state,
@@ -766,7 +759,7 @@ class FederationServer(FederationBase):
         prev_state_ids = await context.get_prev_state_ids()
 
         state_event_ids: Collection[str]
-        servers_in_room: Optional[Collection[str]]
+        servers_in_room: Collection[str] | None
         if caller_supports_partial_state:
             summary = await self.store.get_room_summary(room_id)
             state_event_ids = _get_event_ids_for_partial_state_join(
@@ -809,7 +802,7 @@ class FederationServer(FederationBase):
 
     async def on_make_leave_request(
         self, origin: str, room_id: str, user_id: str
-    ) -> Dict[str, Any]:
+    ) -> dict[str, Any]:
         origin_host, _ = parse_server_name(origin)
         await self.check_server_matches_acl(origin_host, room_id)
         pdu = await self.handler.on_make_leave_request(origin, room_id, user_id)
@@ -826,7 +819,7 @@ class FederationServer(FederationBase):
         return {}
 
     async def on_make_knock_request(
-        self, origin: str, room_id: str, user_id: str, supported_versions: List[str]
+        self, origin: str, room_id: str, user_id: str, supported_versions: list[str]
     ) -> JsonDict:
         """We've received a /make_knock/ request, so we create a partial knock
         event for the room and hand that back, along with the room version, to the knocking
@@ -884,7 +877,7 @@ class FederationServer(FederationBase):
         origin: str,
         content: JsonDict,
         room_id: str,
-    ) -> Dict[str, List[JsonDict]]:
+    ) -> dict[str, list[JsonDict]]:
         """
         We have received a knock event for a room. Verify and send the event into the room
         on the knocking homeserver's behalf. Then reply with some stripped state from the
@@ -1034,7 +1027,7 @@ class FederationServer(FederationBase):
 
     async def on_event_auth(
         self, origin: str, room_id: str, event_id: str
-    ) -> Tuple[int, Dict[str, Any]]:
+    ) -> tuple[int, dict[str, Any]]:
         async with self._server_linearizer.queue((origin, room_id)):
             await self._event_auth_handler.assert_host_in_room(room_id, origin)
             origin_host, _ = parse_server_name(origin)
@@ -1046,20 +1039,20 @@ class FederationServer(FederationBase):
         return 200, res
 
     async def on_query_client_keys(
-        self, origin: str, content: Dict[str, str]
-    ) -> Tuple[int, Dict[str, Any]]:
+        self, origin: str, content: dict[str, str]
+    ) -> tuple[int, dict[str, Any]]:
         return await self.on_query_request("client_keys", content)
 
     async def on_query_user_devices(
         self, origin: str, user_id: str
-    ) -> Tuple[int, Dict[str, Any]]:
+    ) -> tuple[int, dict[str, Any]]:
         keys = await self.device_handler.on_federation_query_user_devices(user_id)
         return 200, keys
 
     @trace
     async def on_claim_client_keys(
-        self, query: List[Tuple[str, str, str, int]], always_include_fallback_keys: bool
-    ) -> Dict[str, Any]:
+        self, query: list[tuple[str, str, str, int]], always_include_fallback_keys: bool
+    ) -> dict[str, Any]:
         if any(
             not self.hs.is_mine(UserID.from_string(user_id))
             for user_id, _, _, _ in query
@@ -1071,7 +1064,7 @@ class FederationServer(FederationBase):
             query, always_include_fallback_keys=always_include_fallback_keys
         )
 
-        json_result: Dict[str, Dict[str, Dict[str, JsonDict]]] = {}
+        json_result: dict[str, dict[str, dict[str, JsonDict]]] = {}
         for result in results:
             for user_id, device_keys in result.items():
                 for device_id, keys in device_keys.items():
@@ -1098,10 +1091,10 @@ class FederationServer(FederationBase):
         self,
         origin: str,
         room_id: str,
-        earliest_events: List[str],
-        latest_events: List[str],
+        earliest_events: list[str],
+        latest_events: list[str],
         limit: int,
-    ) -> Dict[str, list]:
+    ) -> dict[str, list]:
         async with self._server_linearizer.queue((origin, room_id)):
             origin_host, _ = parse_server_name(origin)
             await self.check_server_matches_acl(origin_host, room_id)
@@ -1129,11 +1122,11 @@ class FederationServer(FederationBase):
 
         return {"events": serialize_and_filter_pdus(missing_events, time_now)}
 
-    async def on_openid_userinfo(self, token: str) -> Optional[str]:
+    async def on_openid_userinfo(self, token: str) -> str | None:
         ts_now_ms = self._clock.time_msec()
         return await self.store.get_user_id_for_open_id_token(token, ts_now_ms)
 
-    def _transaction_dict_from_pdus(self, pdu_list: List[EventBase]) -> JsonDict:
+    def _transaction_dict_from_pdus(self, pdu_list: list[EventBase]) -> JsonDict:
         """Returns a new Transaction containing the given PDUs suitable for
         transmission.
         """
@@ -1208,7 +1201,7 @@ class FederationServer(FederationBase):
 
     async def _get_next_nonspam_staged_event_for_room(
         self, room_id: str, room_version: RoomVersion
-    ) -> Optional[Tuple[str, EventBase]]:
+    ) -> tuple[str, EventBase] | None:
         """Fetch the first non-spam event from staging queue.
 
         Args:
@@ -1249,8 +1242,8 @@ class FederationServer(FederationBase):
         room_id: str,
         room_version: RoomVersion,
         lock: Lock,
-        latest_origin: Optional[str] = None,
-        latest_event: Optional[EventBase] = None,
+        latest_origin: str | None = None,
+        latest_event: EventBase | None = None,
     ) -> None:
         """Process events in the staging area for the given room.
 
@@ -1363,13 +1356,13 @@ class FederationServer(FederationBase):
             lock = new_lock
 
     async def exchange_third_party_invite(
-        self, sender_user_id: str, target_user_id: str, room_id: str, signed: Dict
+        self, sender_user_id: str, target_user_id: str, room_id: str, signed: dict
     ) -> None:
         await self.handler.exchange_third_party_invite(
             sender_user_id, target_user_id, room_id, signed
         )
 
-    async def on_exchange_third_party_invite_request(self, event_dict: Dict) -> None:
+    async def on_exchange_third_party_invite_request(self, event_dict: dict) -> None:
         await self.handler.on_exchange_third_party_invite_request(event_dict)
 
     async def check_server_matches_acl(self, server_name: str, room_id: str) -> None:
@@ -1407,13 +1400,13 @@ class FederationHandlerRegistry:
         # the case.
         self._send_edu = ReplicationFederationSendEduRestServlet.make_client(hs)
 
-        self.edu_handlers: Dict[str, Callable[[str, dict], Awaitable[None]]] = {}
-        self.query_handlers: Dict[str, Callable[[dict], Awaitable[JsonDict]]] = {}
+        self.edu_handlers: dict[str, Callable[[str, dict], Awaitable[None]]] = {}
+        self.query_handlers: dict[str, Callable[[dict], Awaitable[JsonDict]]] = {}
 
         # Map from type to instance names that we should route EDU handling to.
         # We randomly choose one instance from the list to route to for each new
         # EDU received.
-        self._edu_type_to_instance: Dict[str, List[str]] = {}
+        self._edu_type_to_instance: dict[str, list[str]] = {}
 
     def register_edu_handler(
         self, edu_type: str, handler: Callable[[str, JsonDict], Awaitable[None]]
@@ -1455,7 +1448,7 @@ class FederationHandlerRegistry:
         self.query_handlers[query_type] = handler
 
     def register_instances_for_edu(
-        self, edu_type: str, instance_names: List[str]
+        self, edu_type: str, instance_names: list[str]
     ) -> None:
         """Register that the EDU handler is on multiple instances."""
         self._edu_type_to_instance[edu_type] = instance_names
diff --git a/synapse/federation/persistence.py b/synapse/federation/persistence.py
index 8340b48503..dca13191fc 100644
--- a/synapse/federation/persistence.py
+++ b/synapse/federation/persistence.py
@@ -27,7 +27,6 @@ These actions are mostly only used by the :py:mod:`.replication` module.
 """
 
 import logging
-from typing import Optional, Tuple
 
 from synapse.federation.units import Transaction
 from synapse.storage.databases.main import DataStore
@@ -44,7 +43,7 @@ class TransactionActions:
 
     async def have_responded(
         self, origin: str, transaction: Transaction
-    ) -> Optional[Tuple[int, JsonDict]]:
+    ) -> tuple[int, JsonDict] | None:
         """Have we already responded to a transaction with the same id and
         origin?
 
diff --git a/synapse/federation/send_queue.py b/synapse/federation/send_queue.py
index 2fdee9ac54..cf70e10a58 100644
--- a/synapse/federation/send_queue.py
+++ b/synapse/federation/send_queue.py
@@ -40,14 +40,9 @@ import logging
 from enum import Enum
 from typing import (
     TYPE_CHECKING,
-    Dict,
     Hashable,
     Iterable,
-    List,
-    Optional,
     Sized,
-    Tuple,
-    Type,
 )
 
 import attr
@@ -77,7 +72,7 @@ class QueueNames(str, Enum):
     PRESENCE_DESTINATIONS = "presence_destinations"
 
 
-queue_name_to_gauge_map: Dict[QueueNames, LaterGauge] = {}
+queue_name_to_gauge_map: dict[QueueNames, LaterGauge] = {}
 
 for queue_name in QueueNames:
     queue_name_to_gauge_map[queue_name] = LaterGauge(
@@ -100,23 +95,23 @@ class FederationRemoteSendQueue(AbstractFederationSender):
         # We may have multiple federation sender instances, so we need to track
         # their positions separately.
         self._sender_instances = hs.config.worker.federation_shard_config.instances
-        self._sender_positions: Dict[str, int] = {}
+        self._sender_positions: dict[str, int] = {}
 
         # Pending presence map user_id -> UserPresenceState
-        self.presence_map: Dict[str, UserPresenceState] = {}
+        self.presence_map: dict[str, UserPresenceState] = {}
 
         # Stores the destinations we need to explicitly send presence to about a
         # given user.
         # Stream position -> (user_id, destinations)
-        self.presence_destinations: SortedDict[int, Tuple[str, Iterable[str]]] = (
+        self.presence_destinations: SortedDict[int, tuple[str, Iterable[str]]] = (
             SortedDict()
         )
 
         # (destination, key) -> EDU
-        self.keyed_edu: Dict[Tuple[str, tuple], Edu] = {}
+        self.keyed_edu: dict[tuple[str, tuple], Edu] = {}
 
         # stream position -> (destination, key)
-        self.keyed_edu_changed: SortedDict[int, Tuple[str, tuple]] = SortedDict()
+        self.keyed_edu_changed: SortedDict[int, tuple[str, tuple]] = SortedDict()
 
         self.edus: SortedDict[int, Edu] = SortedDict()
 
@@ -144,6 +139,9 @@ class FederationRemoteSendQueue(AbstractFederationSender):
 
         self.clock.looping_call(self._clear_queue, 30 * 1000)
 
+    def shutdown(self) -> None:
+        """Stops this federation sender instance from sending further transactions."""
+
     def _next_pos(self) -> int:
         pos = self.pos
         self.pos += 1
@@ -218,7 +216,7 @@ class FederationRemoteSendQueue(AbstractFederationSender):
         destination: str,
         edu_type: str,
         content: JsonDict,
-        key: Optional[Hashable] = None,
+        key: Hashable | None = None,
     ) -> None:
         """As per FederationSender"""
         if self.is_mine_server_name(destination):
@@ -292,7 +290,7 @@ class FederationRemoteSendQueue(AbstractFederationSender):
 
     async def get_replication_rows(
         self, instance_name: str, from_token: int, to_token: int, target_row_count: int
-    ) -> Tuple[List[Tuple[int, Tuple]], int, bool]:
+    ) -> tuple[list[tuple[int, tuple]], int, bool]:
         """Get rows to be sent over federation between the two tokens
 
         Args:
@@ -315,7 +313,7 @@ class FederationRemoteSendQueue(AbstractFederationSender):
 
         # list of tuple(int, BaseFederationRow), where the first is the position
         # of the federation stream.
-        rows: List[Tuple[int, BaseFederationRow]] = []
+        rows: list[tuple[int, BaseFederationRow]] = []
 
         # Fetch presence to send to destinations
         i = self.presence_destinations.bisect_right(from_token)
@@ -410,7 +408,7 @@ class BaseFederationRow:
 @attr.s(slots=True, frozen=True, auto_attribs=True)
 class PresenceDestinationsRow(BaseFederationRow):
     state: UserPresenceState
-    destinations: List[str]
+    destinations: list[str]
 
     TypeId = "pd"
 
@@ -433,7 +431,7 @@ class KeyedEduRow(BaseFederationRow):
     typing EDUs clobber based on room_id.
     """
 
-    key: Tuple[str, ...]  # the edu key passed to send_edu
+    key: tuple[str, ...]  # the edu key passed to send_edu
     edu: Edu
 
     TypeId = "k"
@@ -468,7 +466,7 @@ class EduRow(BaseFederationRow):
         buff.edus.setdefault(self.edu.destination, []).append(self.edu)
 
 
-_rowtypes: Tuple[Type[BaseFederationRow], ...] = (
+_rowtypes: tuple[type[BaseFederationRow], ...] = (
     PresenceDestinationsRow,
     KeyedEduRow,
     EduRow,
@@ -480,16 +478,16 @@ TypeToRow = {Row.TypeId: Row for Row in _rowtypes}
 @attr.s(slots=True, frozen=True, auto_attribs=True)
 class ParsedFederationStreamData:
     # list of tuples of UserPresenceState and destinations
-    presence_destinations: List[Tuple[UserPresenceState, List[str]]]
+    presence_destinations: list[tuple[UserPresenceState, list[str]]]
     # dict of destination -> { key -> Edu }
-    keyed_edus: Dict[str, Dict[Tuple[str, ...], Edu]]
+    keyed_edus: dict[str, dict[tuple[str, ...], Edu]]
     # dict of destination -> [Edu]
-    edus: Dict[str, List[Edu]]
+    edus: dict[str, list[Edu]]
 
 
 async def process_rows_for_federation(
     transaction_queue: FederationSender,
-    rows: List[FederationStream.FederationStreamRow],
+    rows: list[FederationStream.FederationStreamRow],
 ) -> None:
     """Parse a list of rows from the federation stream and put them in the
     transaction queue ready for sending to the relevant homeservers.
diff --git a/synapse/federation/sender/__init__.py b/synapse/federation/sender/__init__.py
index 8e3619d1bc..0bd97c25df 100644
--- a/synapse/federation/sender/__init__.py
+++ b/synapse/federation/sender/__init__.py
@@ -135,13 +135,9 @@ from collections import OrderedDict
 from typing import (
     TYPE_CHECKING,
     Collection,
-    Dict,
     Hashable,
     Iterable,
-    List,
     Literal,
-    Optional,
-    Tuple,
 )
 
 import attr
@@ -168,7 +164,6 @@ from synapse.metrics import (
     events_processed_counter,
 )
 from synapse.metrics.background_process_metrics import (
-    run_as_background_process,
     wrap_as_background_process,
 )
 from synapse.types import (
@@ -232,6 +227,11 @@ WAKEUP_INTERVAL_BETWEEN_DESTINATIONS_SEC = 5
 
 
 class AbstractFederationSender(metaclass=abc.ABCMeta):
+    @abc.abstractmethod
+    def shutdown(self) -> None:
+        """Stops this federation sender instance from sending further transactions."""
+        raise NotImplementedError()
+
     @abc.abstractmethod
     def notify_new_events(self, max_token: RoomStreamToken) -> None:
         """This gets called when we have some new events we might want to
@@ -265,7 +265,7 @@ class AbstractFederationSender(metaclass=abc.ABCMeta):
         destination: str,
         edu_type: str,
         content: JsonDict,
-        key: Optional[Hashable] = None,
+        key: Hashable | None = None,
     ) -> None:
         """Construct an Edu object, and queue it for sending
 
@@ -308,7 +308,7 @@ class AbstractFederationSender(metaclass=abc.ABCMeta):
     @abc.abstractmethod
     async def get_replication_rows(
         self, instance_name: str, from_token: int, to_token: int, target_row_count: int
-    ) -> Tuple[List[Tuple[int, Tuple]], int, bool]:
+    ) -> tuple[list[tuple[int, tuple]], int, bool]:
         raise NotImplementedError()
 
 
@@ -326,6 +326,7 @@ class _DestinationWakeupQueue:
     _MAX_TIME_IN_QUEUE = 30.0
 
     sender: "FederationSender" = attr.ib()
+    hs: "HomeServer" = attr.ib()
     server_name: str = attr.ib()
     """
     Our homeserver name (used to label metrics) (`hs.hostname`).
@@ -408,14 +409,14 @@ class FederationSender(AbstractFederationSender):
         self.is_mine_id = hs.is_mine_id
         self.is_mine_server_name = hs.is_mine_server_name
 
-        self._presence_router: Optional["PresenceRouter"] = None
+        self._presence_router: "PresenceRouter" | None = None
         self._transaction_manager = TransactionManager(hs)
 
         self._instance_name = hs.get_instance_name()
         self._federation_shard_config = hs.config.worker.federation_shard_config
 
         # map from destination to PerDestinationQueue
-        self._per_destination_queues: Dict[str, PerDestinationQueue] = {}
+        self._per_destination_queues: dict[str, PerDestinationQueue] = {}
 
         transaction_queue_pending_destinations_gauge.register_hook(
             homeserver_instance_id=hs.get_instance_id(),
@@ -453,21 +454,33 @@ class FederationSender(AbstractFederationSender):
             1.0 / hs.config.ratelimiting.federation_rr_transactions_per_room_per_second
         )
         self._destination_wakeup_queue = _DestinationWakeupQueue(
-            self, self.server_name, self.clock, max_delay_s=rr_txn_interval_per_room_s
+            self,
+            hs,
+            self.server_name,
+            self.clock,
+            max_delay_s=rr_txn_interval_per_room_s,
         )
 
+        # It is important for `_is_shutdown` to be instantiated before the looping call
+        # for `wake_destinations_needing_catchup`.
+        self._is_shutdown = False
+
         # Regularly wake up destinations that have outstanding PDUs to be caught up
         self.clock.looping_call_now(
-            run_as_background_process,
+            self.hs.run_as_background_process,
             WAKEUP_RETRY_PERIOD_SEC * 1000.0,
             "wake_destinations_needing_catchup",
-            self.server_name,
             self._wake_destinations_needing_catchup,
         )
 
+    def shutdown(self) -> None:
+        self._is_shutdown = True
+        for queue in self._per_destination_queues.values():
+            queue.shutdown()
+
     def _get_per_destination_queue(
         self, destination: str
-    ) -> Optional[PerDestinationQueue]:
+    ) -> PerDestinationQueue | None:
         """Get or create a PerDestinationQueue for the given destination
 
         Args:
@@ -503,16 +516,15 @@ class FederationSender(AbstractFederationSender):
             return
 
         # fire off a processing loop in the background
-        run_as_background_process(
+        self.hs.run_as_background_process(
             "process_event_queue_for_federation",
-            self.server_name,
             self._process_event_queue_loop,
         )
 
     async def _process_event_queue_loop(self) -> None:
         try:
             self._is_processing = True
-            while True:
+            while not self._is_shutdown:
                 last_token = await self.store.get_federation_out_pos("events")
                 (
                     next_token,
@@ -592,7 +604,7 @@ class FederationSender(AbstractFederationSender):
                         )
                         return
 
-                    destinations: Optional[Collection[str]] = None
+                    destinations: Collection[str] | None = None
                     if not event.prev_event_ids():
                         # If there are no prev event IDs then the state is empty
                         # and so no remote servers in the room
@@ -708,7 +720,7 @@ class FederationSender(AbstractFederationSender):
                             **{SERVER_NAME_LABEL: self.server_name},
                         ).observe((now - ts) / 1000)
 
-                async def handle_room_events(events: List[EventBase]) -> None:
+                async def handle_room_events(events: list[EventBase]) -> None:
                     logger.debug(
                         "Handling %i events in room %s", len(events), events[0].room_id
                     )
@@ -720,7 +732,7 @@ class FederationSender(AbstractFederationSender):
                         for event in events:
                             await handle_event(event)
 
-                events_by_room: Dict[str, List[EventBase]] = {}
+                events_by_room: dict[str, list[EventBase]] = {}
 
                 for event_id in event_ids:
                     # `event_entries` is unsorted, so we have to iterate over `event_ids`
@@ -997,7 +1009,7 @@ class FederationSender(AbstractFederationSender):
         destination: str,
         edu_type: str,
         content: JsonDict,
-        key: Optional[Hashable] = None,
+        key: Hashable | None = None,
     ) -> None:
         """Construct an Edu object, and queue it for sending
 
@@ -1025,7 +1037,7 @@ class FederationSender(AbstractFederationSender):
 
         self.send_edu(edu, key)
 
-    def send_edu(self, edu: Edu, key: Optional[Hashable]) -> None:
+    def send_edu(self, edu: Edu, key: Hashable | None) -> None:
         """Queue an EDU for sending
 
         Args:
@@ -1108,7 +1120,7 @@ class FederationSender(AbstractFederationSender):
     @staticmethod
     async def get_replication_rows(
         instance_name: str, from_token: int, to_token: int, target_row_count: int
-    ) -> Tuple[List[Tuple[int, Tuple]], int, bool]:
+    ) -> tuple[list[tuple[int, tuple]], int, bool]:
         # Dummy implementation for case where federation sender isn't offloaded
         # to a worker.
         return [], 0, False
@@ -1121,9 +1133,9 @@ class FederationSender(AbstractFederationSender):
         In order to reduce load spikes, adds a delay between each destination.
         """
 
-        last_processed: Optional[str] = None
+        last_processed: str | None = None
 
-        while True:
+        while not self._is_shutdown:
             destinations_to_wake = (
                 await self.store.get_catch_up_outstanding_destinations(last_processed)
             )
diff --git a/synapse/federation/sender/per_destination_queue.py b/synapse/federation/sender/per_destination_queue.py
index 4c844d403a..4a1b84aed7 100644
--- a/synapse/federation/sender/per_destination_queue.py
+++ b/synapse/federation/sender/per_destination_queue.py
@@ -23,11 +23,13 @@ import datetime
 import logging
 from collections import OrderedDict
 from types import TracebackType
-from typing import TYPE_CHECKING, Dict, Hashable, Iterable, List, Optional, Tuple, Type
+from typing import TYPE_CHECKING, Hashable, Iterable
 
 import attr
 from prometheus_client import Counter
 
+from twisted.internet import defer
+
 from synapse.api.constants import EduTypes
 from synapse.api.errors import (
     FederationDeniedError,
@@ -41,7 +43,6 @@ from synapse.handlers.presence import format_user_presence_state
 from synapse.logging import issue9533_logger
 from synapse.logging.opentracing import SynapseTags, set_tag
 from synapse.metrics import SERVER_NAME_LABEL, sent_transactions_counter
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.types import JsonDict, ReadReceipt
 from synapse.util.retryutils import NotRetryingDestination, get_retry_limiter
 from synapse.visibility import filter_events_for_server
@@ -79,6 +80,7 @@ MAX_PRESENCE_STATES_PER_EDU = 50
 class PerDestinationQueue:
     """
     Manages the per-destination transmission queues.
+    Runs until `shutdown()` is called on the queue.
 
     Args:
         hs
@@ -94,6 +96,7 @@ class PerDestinationQueue:
         destination: str,
     ):
         self.server_name = hs.hostname
+        self._hs = hs
         self._clock = hs.get_clock()
         self._storage_controllers = hs.get_storage_controllers()
         self._store = hs.get_datastores().main
@@ -117,6 +120,8 @@ class PerDestinationQueue:
 
         self._destination = destination
         self.transmission_loop_running = False
+        self._transmission_loop_enabled = True
+        self.active_transmission_loop: defer.Deferred | None = None
 
         # Flag to signal to any running transmission loop that there is new data
         # queued up to be sent.
@@ -137,19 +142,19 @@ class PerDestinationQueue:
 
         # Cache of the last successfully-transmitted stream ordering for this
         # destination (we are the only updater so this is safe)
-        self._last_successful_stream_ordering: Optional[int] = None
+        self._last_successful_stream_ordering: int | None = None
 
         # a queue of pending PDUs
-        self._pending_pdus: List[EventBase] = []
+        self._pending_pdus: list[EventBase] = []
 
         # XXX this is never actually used: see
         # https://github.com/matrix-org/synapse/issues/7549
-        self._pending_edus: List[Edu] = []
+        self._pending_edus: list[Edu] = []
 
         # Pending EDUs by their "key". Keyed EDUs are EDUs that get clobbered
         # based on their key (e.g. typing events by room_id)
         # Map of (edu_type, key) -> Edu
-        self._pending_edus_keyed: Dict[Tuple[str, Hashable], Edu] = {}
+        self._pending_edus_keyed: dict[tuple[str, Hashable], Edu] = {}
 
         # Map of user_id -> UserPresenceState of pending presence to be sent to this
         # destination
@@ -159,7 +164,7 @@ class PerDestinationQueue:
         #
         # Each receipt can only have a single receipt per
         # (room ID, receipt type, user ID, thread ID) tuple.
-        self._pending_receipt_edus: List[Dict[str, Dict[str, Dict[str, dict]]]] = []
+        self._pending_receipt_edus: list[dict[str, dict[str, dict[str, dict]]]] = []
 
         # stream_id of last successfully sent to-device message.
         # NB: may be a long or an int.
@@ -171,6 +176,20 @@ class PerDestinationQueue:
     def __str__(self) -> str:
         return "PerDestinationQueue[%s]" % self._destination
 
+    def shutdown(self) -> None:
+        """Instruct the queue to stop processing any further requests"""
+        self._transmission_loop_enabled = False
+        # The transaction manager must be shutdown before cancelling the active
+        # transmission loop. Otherwise the transmission loop can enter a new cycle of
+        # sleeping before retrying since the shutdown flag of the _transaction_manager
+        # hasn't been set yet.
+        self._transaction_manager.shutdown()
+        try:
+            if self.active_transmission_loop is not None:
+                self.active_transmission_loop.cancel()
+        except Exception:
+            pass
+
     def pending_pdu_count(self) -> int:
         return len(self._pending_pdus)
 
@@ -309,25 +328,28 @@ class PerDestinationQueue:
             )
             return
 
+        if not self._transmission_loop_enabled:
+            logger.warning("Shutdown has been requested. Not sending transaction")
+            return
+
         logger.debug("TX [%s] Starting transaction loop", self._destination)
 
-        run_as_background_process(
+        self.active_transmission_loop = self._hs.run_as_background_process(
             "federation_transaction_transmission_loop",
-            self.server_name,
             self._transaction_transmission_loop,
         )
 
     async def _transaction_transmission_loop(self) -> None:
-        pending_pdus: List[EventBase] = []
+        pending_pdus: list[EventBase] = []
         try:
             self.transmission_loop_running = True
-
             # This will throw if we wouldn't retry. We do this here so we fail
             # quickly, but we will later check this again in the http client,
             # hence why we throw the result away.
             await get_retry_limiter(
                 destination=self._destination,
                 our_server_name=self.server_name,
+                hs=self._hs,
                 clock=self._clock,
                 store=self._store,
             )
@@ -339,7 +361,7 @@ class PerDestinationQueue:
                     # not caught up yet
                     return
 
-            while True:
+            while self._transmission_loop_enabled:
                 self._new_data_to_send = False
 
                 async with _TransactionQueueManager(self) as (
@@ -352,8 +374,8 @@ class PerDestinationQueue:
                         # If we've gotten told about new things to send during
                         # checking for things to send, we try looking again.
                         # Otherwise new PDUs or EDUs might arrive in the meantime,
-                        # but not get sent because we hold the
-                        # `transmission_loop_running` flag.
+                        # but not get sent because we currently have an
+                        # `_active_transmission_loop` running.
                         if self._new_data_to_send:
                             continue
                         else:
@@ -442,6 +464,7 @@ class PerDestinationQueue:
                 )
         finally:
             # We want to be *very* sure we clear this after we stop processing
+            self.active_transmission_loop = None
             self.transmission_loop_running = False
 
     async def _catch_up_transmission_loop(self) -> None:
@@ -469,7 +492,7 @@ class PerDestinationQueue:
         last_successful_stream_ordering: int = _tmp_last_successful_stream_ordering
 
         # get at most 50 catchup room/PDUs
-        while True:
+        while self._transmission_loop_enabled:
             event_ids = await self._store.get_catch_up_room_event_ids(
                 self._destination, last_successful_stream_ordering
             )
@@ -642,12 +665,12 @@ class PerDestinationQueue:
         if not self._pending_receipt_edus:
             self._rrs_pending_flush = False
 
-    def _pop_pending_edus(self, limit: int) -> List[Edu]:
+    def _pop_pending_edus(self, limit: int) -> list[Edu]:
         pending_edus = self._pending_edus
         pending_edus, self._pending_edus = pending_edus[:limit], pending_edus[limit:]
         return pending_edus
 
-    async def _get_device_update_edus(self, limit: int) -> Tuple[List[Edu], int]:
+    async def _get_device_update_edus(self, limit: int) -> tuple[list[Edu], int]:
         last_device_list = self._last_device_list_stream_id
 
         # Retrieve list of new device updates to send to the destination
@@ -668,7 +691,7 @@ class PerDestinationQueue:
 
         return edus, now_stream_id
 
-    async def _get_to_device_message_edus(self, limit: int) -> Tuple[List[Edu], int]:
+    async def _get_to_device_message_edus(self, limit: int) -> tuple[list[Edu], int]:
         last_device_stream_id = self._last_device_stream_id
         to_device_stream_id = self._store.get_to_device_stream_token()
         contents, stream_id = await self._store.get_new_device_msgs_for_remote(
@@ -719,12 +742,12 @@ class _TransactionQueueManager:
 
     queue: PerDestinationQueue
 
-    _device_stream_id: Optional[int] = None
-    _device_list_id: Optional[int] = None
-    _last_stream_ordering: Optional[int] = None
-    _pdus: List[EventBase] = attr.Factory(list)
+    _device_stream_id: int | None = None
+    _device_list_id: int | None = None
+    _last_stream_ordering: int | None = None
+    _pdus: list[EventBase] = attr.Factory(list)
 
-    async def __aenter__(self) -> Tuple[List[EventBase], List[Edu]]:
+    async def __aenter__(self) -> tuple[list[EventBase], list[Edu]]:
         # First we calculate the EDUs we want to send, if any.
 
         # There's a maximum number of EDUs that can be sent with a transaction,
@@ -744,7 +767,7 @@ class _TransactionQueueManager:
         if self.queue._pending_presence:
             # Only send max 50 presence entries in the EDU, to bound the amount
             # of data we're sending.
-            presence_to_add: List[JsonDict] = []
+            presence_to_add: list[JsonDict] = []
             while (
                 self.queue._pending_presence
                 and len(presence_to_add) < MAX_PRESENCE_STATES_PER_EDU
@@ -822,9 +845,9 @@ class _TransactionQueueManager:
 
     async def __aexit__(
         self,
-        exc_type: Optional[Type[BaseException]],
-        exc: Optional[BaseException],
-        tb: Optional[TracebackType],
+        exc_type: type[BaseException] | None,
+        exc: BaseException | None,
+        tb: TracebackType | None,
     ) -> None:
         if exc_type is not None:
             # Failed to send transaction, so we bail out.
diff --git a/synapse/federation/sender/transaction_manager.py b/synapse/federation/sender/transaction_manager.py
index b548d9ed70..99aa05ebd6 100644
--- a/synapse/federation/sender/transaction_manager.py
+++ b/synapse/federation/sender/transaction_manager.py
@@ -18,7 +18,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, List
+from typing import TYPE_CHECKING
 
 from prometheus_client import Gauge
 
@@ -72,12 +72,18 @@ class TransactionManager:
         # HACK to get unique tx id
         self._next_txn_id = int(self.clock.time_msec())
 
+        self._is_shutdown = False
+
+    def shutdown(self) -> None:
+        self._is_shutdown = True
+        self._transport_layer.shutdown()
+
     @measure_func("_send_new_transaction")
     async def send_new_transaction(
         self,
         destination: str,
-        pdus: List[EventBase],
-        edus: List[Edu],
+        pdus: list[EventBase],
+        edus: list[Edu],
     ) -> None:
         """
         Args:
@@ -86,6 +92,12 @@ class TransactionManager:
             edus: List of EDUs to send
         """
 
+        if self._is_shutdown:
+            logger.warning(
+                "TransactionManager has been shutdown, not sending transaction"
+            )
+            return
+
         # Make a transaction-sending opentracing span. This span follows on from
         # all the edus in that transaction. This needs to be done since there is
         # no active span here, so if the edus were not received by the remote the
diff --git a/synapse/federation/transport/client.py b/synapse/federation/transport/client.py
index 5a5dc45f10..35d3c30c69 100644
--- a/synapse/federation/transport/client.py
+++ b/synapse/federation/transport/client.py
@@ -28,14 +28,9 @@ from typing import (
     BinaryIO,
     Callable,
     Collection,
-    Dict,
     Generator,
     Iterable,
-    List,
     Mapping,
-    Optional,
-    Tuple,
-    Union,
 )
 
 import attr
@@ -70,6 +65,9 @@ class TransportLayerClient:
         self.client = hs.get_federation_http_client()
         self._is_mine_server_name = hs.is_mine_server_name
 
+    def shutdown(self) -> None:
+        self.client.shutdown()
+
     async def get_room_state_ids(
         self, destination: str, room_id: str, event_id: str
     ) -> JsonDict:
@@ -122,7 +120,7 @@ class TransportLayerClient:
         )
 
     async def get_event(
-        self, destination: str, event_id: str, timeout: Optional[int] = None
+        self, destination: str, event_id: str, timeout: int | None = None
     ) -> JsonDict:
         """Requests the pdu with give id and origin from the given server.
 
@@ -144,7 +142,7 @@ class TransportLayerClient:
         )
 
     async def get_policy_recommendation_for_pdu(
-        self, destination: str, event: EventBase, timeout: Optional[int] = None
+        self, destination: str, event: EventBase, timeout: int | None = None
     ) -> JsonDict:
         """Requests the policy recommendation for the given pdu from the given policy server.
 
@@ -171,7 +169,7 @@ class TransportLayerClient:
         )
 
     async def ask_policy_server_to_sign_event(
-        self, destination: str, event: EventBase, timeout: Optional[int] = None
+        self, destination: str, event: EventBase, timeout: int | None = None
     ) -> JsonDict:
         """Requests that the destination server (typically a policy server)
         sign the event as not spam.
@@ -198,7 +196,7 @@ class TransportLayerClient:
 
     async def backfill(
         self, destination: str, room_id: str, event_tuples: Collection[str], limit: int
-    ) -> Optional[Union[JsonDict, list]]:
+    ) -> JsonDict | list | None:
         """Requests `limit` previous PDUs in a given context before list of
         PDUs.
 
@@ -235,7 +233,7 @@ class TransportLayerClient:
 
     async def timestamp_to_event(
         self, destination: str, room_id: str, timestamp: int, direction: Direction
-    ) -> Union[JsonDict, List]:
+    ) -> JsonDict | list:
         """
         Calls a remote federating server at `destination` asking for their
         closest event to the given timestamp in the given direction.
@@ -270,7 +268,7 @@ class TransportLayerClient:
     async def send_transaction(
         self,
         transaction: Transaction,
-        json_data_callback: Optional[Callable[[], JsonDict]] = None,
+        json_data_callback: Callable[[], JsonDict] | None = None,
     ) -> JsonDict:
         """Sends the given Transaction to its destination
 
@@ -343,7 +341,7 @@ class TransportLayerClient:
         room_id: str,
         user_id: str,
         membership: str,
-        params: Optional[Mapping[str, Union[str, Iterable[str]]]],
+        params: Mapping[str, str | Iterable[str]] | None,
     ) -> JsonDict:
         """Asks a remote server to build and sign us a membership event
 
@@ -425,7 +423,7 @@ class TransportLayerClient:
         omit_members: bool,
     ) -> "SendJoinResponse":
         path = _create_v2_path("/send_join/%s/%s", room_id, event_id)
-        query_params: Dict[str, str] = {}
+        query_params: dict[str, str] = {}
         # lazy-load state on join
         query_params["omit_members"] = "true" if omit_members else "false"
 
@@ -439,7 +437,7 @@ class TransportLayerClient:
 
     async def send_leave_v1(
         self, destination: str, room_id: str, event_id: str, content: JsonDict
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         path = _create_v1_path("/send_leave/%s/%s", room_id, event_id)
 
         return await self.client.put_json(
@@ -505,7 +503,7 @@ class TransportLayerClient:
 
     async def send_invite_v1(
         self, destination: str, room_id: str, event_id: str, content: JsonDict
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         path = _create_v1_path("/invite/%s/%s", room_id, event_id)
 
         return await self.client.put_json(
@@ -528,11 +526,11 @@ class TransportLayerClient:
     async def get_public_rooms(
         self,
         remote_server: str,
-        limit: Optional[int] = None,
-        since_token: Optional[str] = None,
-        search_filter: Optional[Dict] = None,
+        limit: int | None = None,
+        since_token: str | None = None,
+        search_filter: dict | None = None,
         include_all_networks: bool = False,
-        third_party_instance_id: Optional[str] = None,
+        third_party_instance_id: str | None = None,
     ) -> JsonDict:
         """Get the list of public rooms from a remote homeserver
 
@@ -543,7 +541,7 @@ class TransportLayerClient:
 
         if search_filter:
             # this uses MSC2197 (Search Filtering over Federation)
-            data: Dict[str, Any] = {"include_all_networks": include_all_networks}
+            data: dict[str, Any] = {"include_all_networks": include_all_networks}
             if third_party_instance_id:
                 data["third_party_instance_id"] = third_party_instance_id
             if limit:
@@ -567,7 +565,7 @@ class TransportLayerClient:
                     )
                 raise
         else:
-            args: Dict[str, Union[str, Iterable[str]]] = {
+            args: dict[str, str | Iterable[str]] = {
                 "include_all_networks": "true" if include_all_networks else "false"
             }
             if third_party_instance_id:
@@ -694,7 +692,7 @@ class TransportLayerClient:
         user: UserID,
         destination: str,
         query_content: JsonDict,
-        timeout: Optional[int],
+        timeout: int | None,
     ) -> JsonDict:
         """Claim one-time keys for a list of devices hosted on a remote server.
 
@@ -740,7 +738,7 @@ class TransportLayerClient:
         user: UserID,
         destination: str,
         query_content: JsonDict,
-        timeout: Optional[int],
+        timeout: int | None,
     ) -> JsonDict:
         """Claim one-time keys for a list of devices hosted on a remote server.
 
@@ -851,7 +849,7 @@ class TransportLayerClient:
         )
 
     async def get_account_status(
-        self, destination: str, user_ids: List[str]
+        self, destination: str, user_ids: list[str]
     ) -> JsonDict:
         """
         Args:
@@ -875,7 +873,7 @@ class TransportLayerClient:
         max_timeout_ms: int,
         download_ratelimiter: Ratelimiter,
         ip_address: str,
-    ) -> Tuple[int, Dict[bytes, List[bytes]]]:
+    ) -> tuple[int, dict[bytes, list[bytes]]]:
         path = f"/_matrix/media/r0/download/{destination}/{media_id}"
         return await self.client.get_file(
             destination,
@@ -902,7 +900,7 @@ class TransportLayerClient:
         max_timeout_ms: int,
         download_ratelimiter: Ratelimiter,
         ip_address: str,
-    ) -> Tuple[int, Dict[bytes, List[bytes]]]:
+    ) -> tuple[int, dict[bytes, list[bytes]]]:
         path = f"/_matrix/media/v3/download/{destination}/{media_id}"
         return await self.client.get_file(
             destination,
@@ -933,7 +931,7 @@ class TransportLayerClient:
         max_timeout_ms: int,
         download_ratelimiter: Ratelimiter,
         ip_address: str,
-    ) -> Tuple[int, Dict[bytes, List[bytes]], bytes]:
+    ) -> tuple[int, dict[bytes, list[bytes]], bytes]:
         path = f"/_matrix/federation/v1/media/download/{media_id}"
         return await self.client.federation_get_file(
             destination,
@@ -990,32 +988,32 @@ class SendJoinResponse:
     """The parsed response of a `/send_join` request."""
 
     # The list of auth events from the /send_join response.
-    auth_events: List[EventBase]
+    auth_events: list[EventBase]
     # The list of state from the /send_join response.
-    state: List[EventBase]
+    state: list[EventBase]
     # The raw join event from the /send_join response.
     event_dict: JsonDict
     # The parsed join event from the /send_join response. This will be None if
     # "event" is not included in the response.
-    event: Optional[EventBase] = None
+    event: EventBase | None = None
 
     # The room state is incomplete
     members_omitted: bool = False
 
     # List of servers in the room
-    servers_in_room: Optional[List[str]] = None
+    servers_in_room: list[str] | None = None
 
 
 @attr.s(slots=True, auto_attribs=True)
 class StateRequestResponse:
     """The parsed response of a `/state` request."""
 
-    auth_events: List[EventBase]
-    state: List[EventBase]
+    auth_events: list[EventBase]
+    state: list[EventBase]
 
 
 @ijson.coroutine
-def _event_parser(event_dict: JsonDict) -> Generator[None, Tuple[str, Any], None]:
+def _event_parser(event_dict: JsonDict) -> Generator[None, tuple[str, Any], None]:
     """Helper function for use with `ijson.kvitems_coro` to parse key-value pairs
     to add them to a given dictionary.
     """
@@ -1027,7 +1025,7 @@ def _event_parser(event_dict: JsonDict) -> Generator[None, Tuple[str, Any], None
 
 @ijson.coroutine
 def _event_list_parser(
-    room_version: RoomVersion, events: List[EventBase]
+    room_version: RoomVersion, events: list[EventBase]
 ) -> Generator[None, JsonDict, None]:
     """Helper function for use with `ijson.items_coro` to parse an array of
     events and add them to the given list.
@@ -1083,7 +1081,7 @@ class SendJoinParser(ByteParser[SendJoinResponse]):
     def __init__(self, room_version: RoomVersion, v1_api: bool):
         self._response = SendJoinResponse([], [], event_dict={})
         self._room_version = room_version
-        self._coros: List[Generator[None, bytes, None]] = []
+        self._coros: list[Generator[None, bytes, None]] = []
 
         # The V1 API has the shape of `[200, {...}]`, which we handle by
         # prefixing with `item.*`.
@@ -1156,7 +1154,7 @@ class _StateParser(ByteParser[StateRequestResponse]):
     def __init__(self, room_version: RoomVersion):
         self._response = StateRequestResponse([], [])
         self._room_version = room_version
-        self._coros: List[Generator[None, bytes, None]] = [
+        self._coros: list[Generator[None, bytes, None]] = [
             ijson.items_coro(
                 _event_list_parser(room_version, self._response.state),
                 "pdus.item",
diff --git a/synapse/federation/transport/server/__init__.py b/synapse/federation/transport/server/__init__.py
index c4905e63dd..6d92d00523 100644
--- a/synapse/federation/transport/server/__init__.py
+++ b/synapse/federation/transport/server/__init__.py
@@ -20,7 +20,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, Dict, Iterable, List, Literal, Optional, Tuple, Type
+from typing import TYPE_CHECKING, Iterable, Literal
 
 from synapse.api.errors import FederationDeniedError, SynapseError
 from synapse.federation.transport.server._base import (
@@ -52,7 +52,7 @@ logger = logging.getLogger(__name__)
 class TransportLayerServer(JsonResource):
     """Handles incoming federation HTTP requests"""
 
-    def __init__(self, hs: "HomeServer", servlet_groups: Optional[List[str]] = None):
+    def __init__(self, hs: "HomeServer", servlet_groups: list[str] | None = None):
         """Initialize the TransportLayerServer
 
         Will by default register all servlets. For custom behaviour, pass in
@@ -130,12 +130,12 @@ class PublicRoomList(BaseFederationServlet):
         self.allow_access = hs.config.server.allow_public_rooms_over_federation
 
     async def on_GET(
-        self, origin: str, content: Literal[None], query: Dict[bytes, List[bytes]]
-    ) -> Tuple[int, JsonDict]:
+        self, origin: str, content: Literal[None], query: dict[bytes, list[bytes]]
+    ) -> tuple[int, JsonDict]:
         if not self.allow_access:
             raise FederationDeniedError(origin)
 
-        limit: Optional[int] = parse_integer_from_args(query, "limit", 0)
+        limit: int | None = parse_integer_from_args(query, "limit", 0)
         since_token = parse_string_from_args(query, "since", None)
         include_all_networks = parse_boolean_from_args(
             query, "include_all_networks", default=False
@@ -164,13 +164,13 @@ class PublicRoomList(BaseFederationServlet):
         return 200, data
 
     async def on_POST(
-        self, origin: str, content: JsonDict, query: Dict[bytes, List[bytes]]
-    ) -> Tuple[int, JsonDict]:
+        self, origin: str, content: JsonDict, query: dict[bytes, list[bytes]]
+    ) -> tuple[int, JsonDict]:
         # This implements MSC2197 (Search Filtering over Federation)
         if not self.allow_access:
             raise FederationDeniedError(origin)
 
-        limit: Optional[int] = int(content.get("limit", 100))
+        limit: int | None = int(content.get("limit", 100))
         since_token = content.get("since", None)
         search_filter = content.get("filter", None)
 
@@ -240,10 +240,10 @@ class OpenIdUserInfo(BaseFederationServlet):
 
     async def on_GET(
         self,
-        origin: Optional[str],
+        origin: str | None,
         content: Literal[None],
-        query: Dict[bytes, List[bytes]],
-    ) -> Tuple[int, JsonDict]:
+        query: dict[bytes, list[bytes]],
+    ) -> tuple[int, JsonDict]:
         token = parse_string_from_args(query, "access_token")
         if token is None:
             return (
@@ -265,7 +265,7 @@ class OpenIdUserInfo(BaseFederationServlet):
         return 200, {"sub": user_id}
 
 
-SERVLET_GROUPS: Dict[str, Iterable[Type[BaseFederationServlet]]] = {
+SERVLET_GROUPS: dict[str, Iterable[type[BaseFederationServlet]]] = {
     "federation": FEDERATION_SERVLET_CLASSES,
     "room_list": (PublicRoomList,),
     "openid": (OpenIdUserInfo,),
@@ -281,7 +281,7 @@ def register_servlets(
     resource: HttpServer,
     authenticator: Authenticator,
     ratelimiter: FederationRateLimiter,
-    servlet_groups: Optional[Iterable[str]] = None,
+    servlet_groups: Iterable[str] | None = None,
 ) -> None:
     """Initialize and register servlet classes.
 
diff --git a/synapse/federation/transport/server/_base.py b/synapse/federation/transport/server/_base.py
index cba309635b..52c0c96a3f 100644
--- a/synapse/federation/transport/server/_base.py
+++ b/synapse/federation/transport/server/_base.py
@@ -24,7 +24,7 @@ import logging
 import re
 import time
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Any, Awaitable, Callable, Dict, Optional, Tuple, cast
+from typing import TYPE_CHECKING, Any, Awaitable, Callable, cast
 
 from synapse.api.errors import Codes, FederationDeniedError, SynapseError
 from synapse.api.urls import FEDERATION_V1_PREFIX
@@ -77,7 +77,7 @@ class Authenticator:
 
     # A method just so we can pass 'self' as the authenticator to the Servlets
     async def authenticate_request(
-        self, request: SynapseRequest, content: Optional[JsonDict]
+        self, request: SynapseRequest, content: JsonDict | None
     ) -> str:
         now = self._clock.time_msec()
         json_request: JsonDict = {
@@ -165,7 +165,7 @@ class Authenticator:
             logger.exception("Error resetting retry timings on %s", origin)
 
 
-def _parse_auth_header(header_bytes: bytes) -> Tuple[str, str, str, Optional[str]]:
+def _parse_auth_header(header_bytes: bytes) -> tuple[str, str, str, str | None]:
     """Parse an X-Matrix auth header
 
     Args:
@@ -185,7 +185,7 @@ def _parse_auth_header(header_bytes: bytes) -> Tuple[str, str, str, Optional[str
             rf"{space_or_tab}*,{space_or_tab}*",
             re.split(r"^X-Matrix +", header_str, maxsplit=1)[1],
         )
-        param_dict: Dict[str, str] = {
+        param_dict: dict[str, str] = {
             k.lower(): v for k, v in [param.split("=", maxsplit=1) for param in params]
         }
 
@@ -252,7 +252,7 @@ class BaseFederationServlet:
                 components as specified in the path match regexp.
 
         Returns:
-            Optional[Tuple[int, object]]: either (response code, response object) to
+            tuple[int, object] | None: either (response code, response object) to
                  return a JSON response, or None if the request has already been handled.
 
         Raises:
@@ -282,14 +282,14 @@ class BaseFederationServlet:
         self.ratelimiter = ratelimiter
         self.server_name = server_name
 
-    def _wrap(self, func: Callable[..., Awaitable[Tuple[int, Any]]]) -> ServletCallback:
+    def _wrap(self, func: Callable[..., Awaitable[tuple[int, Any]]]) -> ServletCallback:
         authenticator = self.authenticator
         ratelimiter = self.ratelimiter
 
         @functools.wraps(func)
         async def new_func(
             request: SynapseRequest, *args: Any, **kwargs: str
-        ) -> Optional[Tuple[int, Any]]:
+        ) -> tuple[int, Any] | None:
             """A callback which can be passed to HttpServer.RegisterPaths
 
             Args:
@@ -309,7 +309,7 @@ class BaseFederationServlet:
 
             try:
                 with start_active_span("authenticate_request"):
-                    origin: Optional[str] = await authenticator.authenticate_request(
+                    origin: str | None = await authenticator.authenticate_request(
                         request, content
                     )
             except NoAuthenticationError:
diff --git a/synapse/federation/transport/server/federation.py b/synapse/federation/transport/server/federation.py
index eb96ff27f9..a7c297c0b7 100644
--- a/synapse/federation/transport/server/federation.py
+++ b/synapse/federation/transport/server/federation.py
@@ -22,15 +22,9 @@ import logging
 from collections import Counter
 from typing import (
     TYPE_CHECKING,
-    Dict,
-    List,
     Literal,
     Mapping,
-    Optional,
     Sequence,
-    Tuple,
-    Type,
-    Union,
 )
 
 from synapse.api.constants import Direction, EduTypes
@@ -93,9 +87,9 @@ class FederationSendServlet(BaseFederationServerServlet):
         self,
         origin: str,
         content: JsonDict,
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         transaction_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         """Called on PUT /send/<transaction_id>/
 
         Args:
@@ -158,9 +152,9 @@ class FederationEventServlet(BaseFederationServerServlet):
         self,
         origin: str,
         content: Literal[None],
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         event_id: str,
-    ) -> Tuple[int, Union[JsonDict, str]]:
+    ) -> tuple[int, JsonDict | str]:
         return await self.handler.on_pdu_request(origin, event_id)
 
 
@@ -173,9 +167,9 @@ class FederationStateV1Servlet(BaseFederationServerServlet):
         self,
         origin: str,
         content: Literal[None],
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         room_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         return await self.handler.on_room_state_request(
             origin,
             room_id,
@@ -191,9 +185,9 @@ class FederationStateIdsServlet(BaseFederationServerServlet):
         self,
         origin: str,
         content: Literal[None],
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         room_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         return await self.handler.on_state_ids_request(
             origin,
             room_id,
@@ -209,9 +203,9 @@ class FederationBackfillServlet(BaseFederationServerServlet):
         self,
         origin: str,
         content: Literal[None],
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         room_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         versions = [x.decode("ascii") for x in query[b"v"]]
         limit = parse_integer_from_args(query, "limit", None)
 
@@ -248,9 +242,9 @@ class FederationTimestampLookupServlet(BaseFederationServerServlet):
         self,
         origin: str,
         content: Literal[None],
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         room_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         timestamp = parse_integer_from_args(query, "ts", required=True)
         direction_str = parse_string_from_args(
             query, "dir", allowed_values=["f", "b"], required=True
@@ -271,9 +265,9 @@ class FederationQueryServlet(BaseFederationServerServlet):
         self,
         origin: str,
         content: Literal[None],
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         query_type: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         args = {k.decode("utf8"): v[0].decode("utf-8") for k, v in query.items()}
         args["origin"] = origin
         return await self.handler.on_query_request(query_type, args)
@@ -287,10 +281,10 @@ class FederationMakeJoinServlet(BaseFederationServerServlet):
         self,
         origin: str,
         content: Literal[None],
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         room_id: str,
         user_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         """
         Args:
             origin: The authenticated server_name of the calling server
@@ -323,10 +317,10 @@ class FederationMakeLeaveServlet(BaseFederationServerServlet):
         self,
         origin: str,
         content: Literal[None],
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         room_id: str,
         user_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         result = await self.handler.on_make_leave_request(origin, room_id, user_id)
         return 200, result
 
@@ -339,10 +333,10 @@ class FederationV1SendLeaveServlet(BaseFederationServerServlet):
         self,
         origin: str,
         content: JsonDict,
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         room_id: str,
         event_id: str,
-    ) -> Tuple[int, Tuple[int, JsonDict]]:
+    ) -> tuple[int, tuple[int, JsonDict]]:
         result = await self.handler.on_send_leave_request(origin, content, room_id)
         return 200, (200, result)
 
@@ -357,10 +351,10 @@ class FederationV2SendLeaveServlet(BaseFederationServerServlet):
         self,
         origin: str,
         content: JsonDict,
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         room_id: str,
         event_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         result = await self.handler.on_send_leave_request(origin, content, room_id)
         return 200, result
 
@@ -373,10 +367,10 @@ class FederationMakeKnockServlet(BaseFederationServerServlet):
         self,
         origin: str,
         content: Literal[None],
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         room_id: str,
         user_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         # Retrieve the room versions the remote homeserver claims to support
         supported_versions = parse_strings_from_args(
             query, "ver", required=True, encoding="utf-8"
@@ -396,10 +390,10 @@ class FederationV1SendKnockServlet(BaseFederationServerServlet):
         self,
         origin: str,
         content: JsonDict,
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         room_id: str,
         event_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         result = await self.handler.on_send_knock_request(origin, content, room_id)
         return 200, result
 
@@ -412,10 +406,10 @@ class FederationEventAuthServlet(BaseFederationServerServlet):
         self,
         origin: str,
         content: Literal[None],
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         room_id: str,
         event_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         return await self.handler.on_event_auth(origin, room_id, event_id)
 
 
@@ -427,10 +421,10 @@ class FederationV1SendJoinServlet(BaseFederationServerServlet):
         self,
         origin: str,
         content: JsonDict,
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         room_id: str,
         event_id: str,
-    ) -> Tuple[int, Tuple[int, JsonDict]]:
+    ) -> tuple[int, tuple[int, JsonDict]]:
         # TODO(paul): assert that event_id parsed from path actually
         #   match those given in content
         result = await self.handler.on_send_join_request(origin, content, room_id)
@@ -447,10 +441,10 @@ class FederationV2SendJoinServlet(BaseFederationServerServlet):
         self,
         origin: str,
         content: JsonDict,
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         room_id: str,
         event_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         # TODO(paul): assert that event_id parsed from path actually
         #   match those given in content
 
@@ -470,10 +464,10 @@ class FederationV1InviteServlet(BaseFederationServerServlet):
         self,
         origin: str,
         content: JsonDict,
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         room_id: str,
         event_id: str,
-    ) -> Tuple[int, Tuple[int, JsonDict]]:
+    ) -> tuple[int, tuple[int, JsonDict]]:
         # We don't get a room version, so we have to assume its EITHER v1 or
         # v2. This is "fine" as the only difference between V1 and V2 is the
         # state resolution algorithm, and we don't use that for processing
@@ -497,10 +491,10 @@ class FederationV2InviteServlet(BaseFederationServerServlet):
         self,
         origin: str,
         content: JsonDict,
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         room_id: str,
         event_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         # TODO(paul): assert that room_id/event_id parsed from path actually
         #   match those given in content
 
@@ -535,9 +529,9 @@ class FederationThirdPartyInviteExchangeServlet(BaseFederationServerServlet):
         self,
         origin: str,
         content: JsonDict,
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         room_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await self.handler.on_exchange_third_party_invite_request(content)
         return 200, {}
 
@@ -547,8 +541,8 @@ class FederationClientKeysQueryServlet(BaseFederationServerServlet):
     CATEGORY = "Federation requests"
 
     async def on_POST(
-        self, origin: str, content: JsonDict, query: Dict[bytes, List[bytes]]
-    ) -> Tuple[int, JsonDict]:
+        self, origin: str, content: JsonDict, query: dict[bytes, list[bytes]]
+    ) -> tuple[int, JsonDict]:
         return await self.handler.on_query_client_keys(origin, content)
 
 
@@ -560,9 +554,9 @@ class FederationUserDevicesQueryServlet(BaseFederationServerServlet):
         self,
         origin: str,
         content: Literal[None],
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         user_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         return await self.handler.on_query_user_devices(origin, user_id)
 
 
@@ -571,10 +565,10 @@ class FederationClientKeysClaimServlet(BaseFederationServerServlet):
     CATEGORY = "Federation requests"
 
     async def on_POST(
-        self, origin: str, content: JsonDict, query: Dict[bytes, List[bytes]]
-    ) -> Tuple[int, JsonDict]:
+        self, origin: str, content: JsonDict, query: dict[bytes, list[bytes]]
+    ) -> tuple[int, JsonDict]:
         # Generate a count for each algorithm, which is hard-coded to 1.
-        key_query: List[Tuple[str, str, str, int]] = []
+        key_query: list[tuple[str, str, str, int]] = []
         for user_id, device_keys in content.get("one_time_keys", {}).items():
             for device_id, algorithm in device_keys.items():
                 key_query.append((user_id, device_id, algorithm, 1))
@@ -597,10 +591,10 @@ class FederationUnstableClientKeysClaimServlet(BaseFederationServerServlet):
     CATEGORY = "Federation requests"
 
     async def on_POST(
-        self, origin: str, content: JsonDict, query: Dict[bytes, List[bytes]]
-    ) -> Tuple[int, JsonDict]:
+        self, origin: str, content: JsonDict, query: dict[bytes, list[bytes]]
+    ) -> tuple[int, JsonDict]:
         # Generate a count for each algorithm.
-        key_query: List[Tuple[str, str, str, int]] = []
+        key_query: list[tuple[str, str, str, int]] = []
         for user_id, device_keys in content.get("one_time_keys", {}).items():
             for device_id, algorithms in device_keys.items():
                 counts = Counter(algorithms)
@@ -621,9 +615,9 @@ class FederationGetMissingEventsServlet(BaseFederationServerServlet):
         self,
         origin: str,
         content: JsonDict,
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         room_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         limit = int(content.get("limit", 10))
         earliest_events = content.get("earliest_events", [])
         latest_events = content.get("latest_events", [])
@@ -646,8 +640,8 @@ class On3pidBindServlet(BaseFederationServerServlet):
     REQUIRE_AUTH = False
 
     async def on_POST(
-        self, origin: Optional[str], content: JsonDict, query: Dict[bytes, List[bytes]]
-    ) -> Tuple[int, JsonDict]:
+        self, origin: str | None, content: JsonDict, query: dict[bytes, list[bytes]]
+    ) -> tuple[int, JsonDict]:
         if "invites" in content:
             last_exception = None
             for invite in content["invites"]:
@@ -680,10 +674,10 @@ class FederationVersionServlet(BaseFederationServlet):
 
     async def on_GET(
         self,
-        origin: Optional[str],
+        origin: str | None,
         content: Literal[None],
-        query: Dict[bytes, List[bytes]],
-    ) -> Tuple[int, JsonDict]:
+        query: dict[bytes, list[bytes]],
+    ) -> tuple[int, JsonDict]:
         return (
             200,
             {
@@ -715,7 +709,7 @@ class FederationRoomHierarchyServlet(BaseFederationServlet):
         content: Literal[None],
         query: Mapping[bytes, Sequence[bytes]],
         room_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         suggested_only = parse_boolean_from_args(query, "suggested_only", default=False)
         return 200, await self.handler.get_federation_hierarchy(
             origin, room_id, suggested_only
@@ -746,9 +740,9 @@ class RoomComplexityServlet(BaseFederationServlet):
         self,
         origin: str,
         content: Literal[None],
-        query: Dict[bytes, List[bytes]],
+        query: dict[bytes, list[bytes]],
         room_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         is_public = await self._store.is_room_world_readable_or_publicly_joinable(
             room_id
         )
@@ -780,7 +774,7 @@ class FederationAccountStatusServlet(BaseFederationServerServlet):
         content: JsonDict,
         query: Mapping[bytes, Sequence[bytes]],
         room_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         if "user_ids" not in content:
             raise SynapseError(
                 400, "Required parameter 'user_ids' is missing", Codes.MISSING_PARAM
@@ -816,7 +810,7 @@ class FederationMediaDownloadServlet(BaseFederationServerServlet):
 
     async def on_GET(
         self,
-        origin: Optional[str],
+        origin: str | None,
         content: Literal[None],
         request: SynapseRequest,
         media_id: str,
@@ -856,7 +850,7 @@ class FederationMediaThumbnailServlet(BaseFederationServerServlet):
 
     async def on_GET(
         self,
-        origin: Optional[str],
+        origin: str | None,
         content: Literal[None],
         request: SynapseRequest,
         media_id: str,
@@ -882,7 +876,7 @@ class FederationMediaThumbnailServlet(BaseFederationServerServlet):
         self.media_repo.mark_recently_accessed(None, media_id)
 
 
-FEDERATION_SERVLET_CLASSES: Tuple[Type[BaseFederationServlet], ...] = (
+FEDERATION_SERVLET_CLASSES: tuple[type[BaseFederationServlet], ...] = (
     FederationSendServlet,
     FederationEventServlet,
     FederationStateV1Servlet,
diff --git a/synapse/federation/units.py b/synapse/federation/units.py
index 3bb5f824b7..547db9a394 100644
--- a/synapse/federation/units.py
+++ b/synapse/federation/units.py
@@ -24,7 +24,7 @@ server protocol.
 """
 
 import logging
-from typing import List, Optional, Sequence
+from typing import Sequence
 
 import attr
 
@@ -70,7 +70,7 @@ class Edu:
         getattr(self, "content", {})["org.matrix.opentracing_context"] = "{}"
 
 
-def _none_to_list(edus: Optional[List[JsonDict]]) -> List[JsonDict]:
+def _none_to_list(edus: list[JsonDict] | None) -> list[JsonDict]:
     if edus is None:
         return []
     return edus
@@ -98,8 +98,8 @@ class Transaction:
     origin: str
     destination: str
     origin_server_ts: int
-    pdus: List[JsonDict] = attr.ib(factory=list, converter=_none_to_list)
-    edus: List[JsonDict] = attr.ib(factory=list, converter=_none_to_list)
+    pdus: list[JsonDict] = attr.ib(factory=list, converter=_none_to_list)
+    edus: list[JsonDict] = attr.ib(factory=list, converter=_none_to_list)
 
     def get_dict(self) -> JsonDict:
         """A JSON-ready dictionary of valid keys which aren't internal."""
@@ -113,7 +113,7 @@ class Transaction:
         return result
 
 
-def filter_pdus_for_valid_depth(pdus: Sequence[JsonDict]) -> List[JsonDict]:
+def filter_pdus_for_valid_depth(pdus: Sequence[JsonDict]) -> list[JsonDict]:
     filtered_pdus = []
     for pdu in pdus:
         # Drop PDUs that have a depth that is outside of the range allowed
@@ -128,6 +128,6 @@ def filter_pdus_for_valid_depth(pdus: Sequence[JsonDict]) -> List[JsonDict]:
 
 
 def serialize_and_filter_pdus(
-    pdus: Sequence[EventBase], time_now: Optional[int] = None
-) -> List[JsonDict]:
+    pdus: Sequence[EventBase], time_now: int | None = None
+) -> list[JsonDict]:
     return filter_pdus_for_valid_depth([pdu.get_pdu_json(time_now) for pdu in pdus])
diff --git a/synapse/handlers/account.py b/synapse/handlers/account.py
index 37cc3d3ff5..855027f08e 100644
--- a/synapse/handlers/account.py
+++ b/synapse/handlers/account.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import TYPE_CHECKING, Dict, List, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.errors import Codes, SynapseError
 from synapse.types import JsonDict, UserID
@@ -40,9 +40,9 @@ class AccountHandler:
 
     async def get_account_statuses(
         self,
-        user_ids: List[str],
+        user_ids: list[str],
         allow_remote: bool,
-    ) -> Tuple[JsonDict, List[str]]:
+    ) -> tuple[JsonDict, list[str]]:
         """Get account statuses for a list of user IDs.
 
         If one or more account(s) belong to remote homeservers, retrieve their status(es)
@@ -63,7 +63,7 @@ class AccountHandler:
         """
         statuses = {}
         failures = []
-        remote_users: List[UserID] = []
+        remote_users: list[UserID] = []
 
         for raw_user_id in user_ids:
             try:
@@ -127,8 +127,8 @@ class AccountHandler:
         return status
 
     async def _get_remote_account_statuses(
-        self, remote_users: List[UserID]
-    ) -> Tuple[JsonDict, List[str]]:
+        self, remote_users: list[UserID]
+    ) -> tuple[JsonDict, list[str]]:
         """Send out federation requests to retrieve the statuses of remote accounts.
 
         Args:
@@ -140,7 +140,7 @@ class AccountHandler:
         """
         # Group remote users by destination, so we only send one request per remote
         # homeserver.
-        by_destination: Dict[str, List[str]] = {}
+        by_destination: dict[str, list[str]] = {}
         for user in remote_users:
             if user.domain not in by_destination:
                 by_destination[user.domain] = []
@@ -149,7 +149,7 @@ class AccountHandler:
 
         # Retrieve the statuses and failures for remote accounts.
         final_statuses: JsonDict = {}
-        final_failures: List[str] = []
+        final_failures: list[str] = []
         for destination, users in by_destination.items():
             statuses, failures = await self._federation_client.get_account_status(
                 destination,
diff --git a/synapse/handlers/account_data.py b/synapse/handlers/account_data.py
index 228132db48..c6168377ee 100644
--- a/synapse/handlers/account_data.py
+++ b/synapse/handlers/account_data.py
@@ -21,7 +21,7 @@
 #
 import logging
 import random
-from typing import TYPE_CHECKING, Awaitable, Callable, List, Optional, Tuple
+from typing import TYPE_CHECKING, Awaitable, Callable
 
 from synapse.api.constants import AccountDataTypes
 from synapse.replication.http.account_data import (
@@ -40,9 +40,7 @@ if TYPE_CHECKING:
 
 logger = logging.getLogger(__name__)
 
-ON_ACCOUNT_DATA_UPDATED_CALLBACK = Callable[
-    [str, Optional[str], str, JsonDict], Awaitable
-]
+ON_ACCOUNT_DATA_UPDATED_CALLBACK = Callable[[str, str | None, str, JsonDict], Awaitable]
 
 
 class AccountDataHandler:
@@ -67,12 +65,12 @@ class AccountDataHandler:
         self._remove_tag_client = ReplicationRemoveTagRestServlet.make_client(hs)
         self._account_data_writers = hs.config.worker.writers.account_data
 
-        self._on_account_data_updated_callbacks: List[
+        self._on_account_data_updated_callbacks: list[
             ON_ACCOUNT_DATA_UPDATED_CALLBACK
         ] = []
 
     def register_module_callbacks(
-        self, on_account_data_updated: Optional[ON_ACCOUNT_DATA_UPDATED_CALLBACK] = None
+        self, on_account_data_updated: ON_ACCOUNT_DATA_UPDATED_CALLBACK | None = None
     ) -> None:
         """Register callbacks from modules."""
         if on_account_data_updated is not None:
@@ -81,7 +79,7 @@ class AccountDataHandler:
     async def _notify_modules(
         self,
         user_id: str,
-        room_id: Optional[str],
+        room_id: str | None,
         account_data_type: str,
         content: JsonDict,
     ) -> None:
@@ -143,7 +141,7 @@ class AccountDataHandler:
 
     async def remove_account_data_for_room(
         self, user_id: str, room_id: str, account_data_type: str
-    ) -> Optional[int]:
+    ) -> int | None:
         """
         Deletes the room account data for the given user and account data type.
 
@@ -219,7 +217,7 @@ class AccountDataHandler:
 
     async def remove_account_data_for_user(
         self, user_id: str, account_data_type: str
-    ) -> Optional[int]:
+    ) -> int | None:
         """Removes a piece of global account_data for a user.
 
         Args:
@@ -324,8 +322,8 @@ class AccountDataEventSource(EventSource[int, JsonDict]):
         limit: int,
         room_ids: StrCollection,
         is_guest: bool,
-        explicit_room_id: Optional[str] = None,
-    ) -> Tuple[List[JsonDict], int]:
+        explicit_room_id: str | None = None,
+    ) -> tuple[list[JsonDict], int]:
         user_id = user.to_string()
         last_stream_id = from_key
 
diff --git a/synapse/handlers/account_validity.py b/synapse/handlers/account_validity.py
index 39a22b8cbb..bc50efa1a7 100644
--- a/synapse/handlers/account_validity.py
+++ b/synapse/handlers/account_validity.py
@@ -21,7 +21,7 @@
 import email.mime.multipart
 import email.utils
 import logging
-from typing import TYPE_CHECKING, List, Optional, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.errors import AuthError, StoreError, SynapseError
 from synapse.metrics.background_process_metrics import wrap_as_background_process
@@ -37,10 +37,8 @@ logger = logging.getLogger(__name__)
 
 class AccountValidityHandler:
     def __init__(self, hs: "HomeServer"):
-        self.hs = hs
-        self.server_name = (
-            hs.hostname
-        )  # nb must be called this for @wrap_as_background_process
+        self.hs = hs  # nb must be called this for @wrap_as_background_process
+        self.server_name = hs.hostname
         self.config = hs.config
         self.store = hs.get_datastores().main
         self.send_email_handler = hs.get_send_email_handler()
@@ -110,8 +108,8 @@ class AccountValidityHandler:
     async def on_user_login(
         self,
         user_id: str,
-        auth_provider_type: Optional[str],
-        auth_provider_id: Optional[str],
+        auth_provider_type: str | None,
+        auth_provider_id: str | None,
     ) -> None:
         """Tell third-party modules about a user logins.
 
@@ -224,7 +222,7 @@ class AccountValidityHandler:
 
         await self.store.set_renewal_mail_status(user_id=user_id, email_sent=True)
 
-    async def _get_email_addresses_for_user(self, user_id: str) -> List[str]:
+    async def _get_email_addresses_for_user(self, user_id: str) -> list[str]:
         """Retrieve the list of email addresses attached to a user's account.
 
         Args:
@@ -265,7 +263,7 @@ class AccountValidityHandler:
                 attempts += 1
         raise StoreError(500, "Couldn't generate a unique string as refresh string.")
 
-    async def renew_account(self, renewal_token: str) -> Tuple[bool, bool, int]:
+    async def renew_account(self, renewal_token: str) -> tuple[bool, bool, int]:
         """Renews the account attached to a given renewal token by pushing back the
         expiration date by the current validity period in the server's configuration.
 
@@ -328,9 +326,9 @@ class AccountValidityHandler:
     async def renew_account_for_user(
         self,
         user_id: str,
-        expiration_ts: Optional[int] = None,
+        expiration_ts: int | None = None,
         email_sent: bool = False,
-        renewal_token: Optional[str] = None,
+        renewal_token: str | None = None,
     ) -> int:
         """Renews the account attached to a given user by pushing back the
         expiration date by the current validity period in the server's
diff --git a/synapse/handlers/admin.py b/synapse/handlers/admin.py
index e90d675b59..c979752f7f 100644
--- a/synapse/handlers/admin.py
+++ b/synapse/handlers/admin.py
@@ -24,13 +24,8 @@ import logging
 from typing import (
     TYPE_CHECKING,
     Any,
-    Dict,
-    List,
     Mapping,
-    Optional,
     Sequence,
-    Set,
-    Tuple,
 )
 
 import attr
@@ -75,7 +70,7 @@ class AdminHandler:
 
         self.hs = hs
 
-    async def get_redact_task(self, redact_id: str) -> Optional[ScheduledTask]:
+    async def get_redact_task(self, redact_id: str) -> ScheduledTask | None:
         """Get the current status of an active redaction process
 
         Args:
@@ -103,11 +98,9 @@ class AdminHandler:
 
         return ret
 
-    async def get_user(self, user: UserID) -> Optional[JsonMapping]:
+    async def get_user(self, user: UserID) -> JsonMapping | None:
         """Function to get user details"""
-        user_info: Optional[UserInfo] = await self._store.get_user_by_id(
-            user.to_string()
-        )
+        user_info: UserInfo | None = await self._store.get_user_by_id(user.to_string())
         if user_info is None:
             return None
 
@@ -218,7 +211,7 @@ class AdminHandler:
             to_key = RoomStreamToken(stream=stream_ordering)
 
             # Events that we've processed in this room
-            written_events: Set[str] = set()
+            written_events: set[str] = set()
 
             # We need to track gaps in the events stream so that we can then
             # write out the state at those events. We do this by keeping track
@@ -231,7 +224,7 @@ class AdminHandler:
             # The reverse mapping to above, i.e. map from unseen event to events
             # that have the unseen event in their prev_events, i.e. the unseen
             # events "children".
-            unseen_to_child_events: Dict[str, Set[str]] = {}
+            unseen_to_child_events: dict[str, set[str]] = {}
 
             # We fetch events in the room the user could see by fetching *all*
             # events that we have and then filtering, this isn't the most
@@ -359,8 +352,8 @@ class AdminHandler:
         rooms: list,
         requester: JsonMapping,
         use_admin: bool,
-        reason: Optional[str],
-        limit: Optional[int],
+        reason: str | None,
+        limit: int | None,
     ) -> str:
         """
         Start a task redacting the events of the given user in the given rooms
@@ -412,7 +405,7 @@ class AdminHandler:
 
     async def _redact_all_events(
         self, task: ScheduledTask
-    ) -> Tuple[TaskStatus, Optional[Mapping[str, Any]], Optional[str]]:
+    ) -> tuple[TaskStatus, Mapping[str, Any] | None, str | None]:
         """
         Task to redact all of a users events in the given rooms, tracking which, if any, events
         whose redaction failed
@@ -518,7 +511,7 @@ class ExfiltrationWriter(metaclass=abc.ABCMeta):
     """Interface used to specify how to write exported data."""
 
     @abc.abstractmethod
-    def write_events(self, room_id: str, events: List[EventBase]) -> None:
+    def write_events(self, room_id: str, events: list[EventBase]) -> None:
         """Write a batch of events for a room."""
         raise NotImplementedError()
 
diff --git a/synapse/handlers/appservice.py b/synapse/handlers/appservice.py
index bf36cf39a1..c91d2adbe1 100644
--- a/synapse/handlers/appservice.py
+++ b/synapse/handlers/appservice.py
@@ -22,13 +22,8 @@ import logging
 from typing import (
     TYPE_CHECKING,
     Collection,
-    Dict,
     Iterable,
-    List,
     Mapping,
-    Optional,
-    Tuple,
-    Union,
 )
 
 from prometheus_client import Counter
@@ -47,7 +42,6 @@ from synapse.metrics import (
     event_processing_loop_room_count,
 )
 from synapse.metrics.background_process_metrics import (
-    run_as_background_process,
     wrap_as_background_process,
 )
 from synapse.storage.databases.main.directory import RoomAliasMapping
@@ -76,9 +70,8 @@ events_processed_counter = Counter(
 
 class ApplicationServicesHandler:
     def __init__(self, hs: "HomeServer"):
-        self.server_name = (
-            hs.hostname
-        )  # nb must be called this for @wrap_as_background_process
+        self.server_name = hs.hostname
+        self.hs = hs  # nb must be called this for @wrap_as_background_process
         self.store = hs.get_datastores().main
         self.is_mine_id = hs.is_mine_id
         self.appservice_api = hs.get_application_service_api()
@@ -145,7 +138,7 @@ class ApplicationServicesHandler:
                         event_to_received_ts.keys(), get_prev_content=True
                     )
 
-                    events_by_room: Dict[str, List[EventBase]] = {}
+                    events_by_room: dict[str, list[EventBase]] = {}
                     for event in events:
                         events_by_room.setdefault(event.room_id, []).append(event)
 
@@ -171,8 +164,8 @@ class ApplicationServicesHandler:
                                 except Exception:
                                     logger.error("Application Services Failure")
 
-                            run_as_background_process(
-                                "as_scheduler", self.server_name, start_scheduler
+                            self.hs.run_as_background_process(
+                                "as_scheduler", start_scheduler
                             )
                             self.started_scheduler = True
 
@@ -245,8 +238,8 @@ class ApplicationServicesHandler:
     def notify_interested_services_ephemeral(
         self,
         stream_key: StreamKeyType,
-        new_token: Union[int, RoomStreamToken, MultiWriterStreamToken],
-        users: Collection[Union[str, UserID]],
+        new_token: int | RoomStreamToken | MultiWriterStreamToken,
+        users: Collection[str | UserID],
     ) -> None:
         """
         This is called by the notifier in the background when an ephemeral event is handled
@@ -343,10 +336,10 @@ class ApplicationServicesHandler:
     @wrap_as_background_process("notify_interested_services_ephemeral")
     async def _notify_interested_services_ephemeral(
         self,
-        services: List[ApplicationService],
+        services: list[ApplicationService],
         stream_key: StreamKeyType,
-        new_token: Union[int, MultiWriterStreamToken],
-        users: Collection[Union[str, UserID]],
+        new_token: int | MultiWriterStreamToken,
+        users: Collection[str | UserID],
     ) -> None:
         logger.debug("Checking interested services for %s", stream_key)
         with Measure(
@@ -431,7 +424,7 @@ class ApplicationServicesHandler:
 
     async def _handle_typing(
         self, service: ApplicationService, new_token: int
-    ) -> List[JsonMapping]:
+    ) -> list[JsonMapping]:
         """
         Return the typing events since the given stream token that the given application
         service should receive.
@@ -466,7 +459,7 @@ class ApplicationServicesHandler:
 
     async def _handle_receipts(
         self, service: ApplicationService, new_token: MultiWriterStreamToken
-    ) -> List[JsonMapping]:
+    ) -> list[JsonMapping]:
         """
         Return the latest read receipts that the given application service should receive.
 
@@ -503,9 +496,9 @@ class ApplicationServicesHandler:
     async def _handle_presence(
         self,
         service: ApplicationService,
-        users: Collection[Union[str, UserID]],
-        new_token: Optional[int],
-    ) -> List[JsonMapping]:
+        users: Collection[str | UserID],
+        new_token: int | None,
+    ) -> list[JsonMapping]:
         """
         Return the latest presence updates that the given application service should receive.
 
@@ -525,7 +518,7 @@ class ApplicationServicesHandler:
             A list of json dictionaries containing data derived from the presence events
             that should be sent to the given application service.
         """
-        events: List[JsonMapping] = []
+        events: list[JsonMapping] = []
         presence_source = self.event_sources.sources.presence
         from_key = await self.store.get_type_stream_id_for_appservice(
             service, "presence"
@@ -564,8 +557,8 @@ class ApplicationServicesHandler:
         self,
         service: ApplicationService,
         new_token: int,
-        users: Collection[Union[str, UserID]],
-    ) -> List[JsonDict]:
+        users: Collection[str | UserID],
+    ) -> list[JsonDict]:
         """
         Given an application service, determine which events it should receive
         from those between the last-recorded to-device message stream token for this
@@ -587,7 +580,7 @@ class ApplicationServicesHandler:
         )
 
         # Filter out users that this appservice is not interested in
-        users_appservice_is_interested_in: List[str] = []
+        users_appservice_is_interested_in: list[str] = []
         for user in users:
             # FIXME: We should do this farther up the call stack. We currently repeat
             #  this operation in _handle_presence.
@@ -614,7 +607,7 @@ class ApplicationServicesHandler:
         #
         # So we mangle this dict into a flat list of to-device messages with the relevant
         # user ID and device ID embedded inside each message dict.
-        message_payload: List[JsonDict] = []
+        message_payload: list[JsonDict] = []
         for (
             user_id,
             device_id,
@@ -738,7 +731,7 @@ class ApplicationServicesHandler:
 
     async def query_room_alias_exists(
         self, room_alias: RoomAlias
-    ) -> Optional[RoomAliasMapping]:
+    ) -> RoomAliasMapping | None:
         """Check if an application service knows this room alias exists.
 
         Args:
@@ -763,8 +756,8 @@ class ApplicationServicesHandler:
         return None
 
     async def query_3pe(
-        self, kind: str, protocol: str, fields: Dict[bytes, List[bytes]]
-    ) -> List[JsonDict]:
+        self, kind: str, protocol: str, fields: dict[bytes, list[bytes]]
+    ) -> list[JsonDict]:
         services = self._get_services_for_3pn(protocol)
 
         results = await make_deferred_yieldable(
@@ -787,10 +780,10 @@ class ApplicationServicesHandler:
         return ret
 
     async def get_3pe_protocols(
-        self, only_protocol: Optional[str] = None
-    ) -> Dict[str, JsonDict]:
+        self, only_protocol: str | None = None
+    ) -> dict[str, JsonDict]:
         services = self.store.get_app_services()
-        protocols: Dict[str, List[JsonDict]] = {}
+        protocols: dict[str, list[JsonDict]] = {}
 
         # Collect up all the individual protocol responses out of the ASes
         for s in services:
@@ -806,7 +799,7 @@ class ApplicationServicesHandler:
                 if info is not None:
                     protocols[p].append(info)
 
-        def _merge_instances(infos: List[JsonDict]) -> JsonDict:
+        def _merge_instances(infos: list[JsonDict]) -> JsonDict:
             # Merge the 'instances' lists of multiple results, but just take
             # the other fields from the first as they ought to be identical
             # copy the result so as not to corrupt the cached one
@@ -824,7 +817,7 @@ class ApplicationServicesHandler:
 
     async def _get_services_for_event(
         self, event: EventBase
-    ) -> List[ApplicationService]:
+    ) -> list[ApplicationService]:
         """Retrieve a list of application services interested in this event.
 
         Args:
@@ -844,11 +837,11 @@ class ApplicationServicesHandler:
 
         return interested_list
 
-    def _get_services_for_user(self, user_id: str) -> List[ApplicationService]:
+    def _get_services_for_user(self, user_id: str) -> list[ApplicationService]:
         services = self.store.get_app_services()
         return [s for s in services if (s.is_interested_in_user(user_id))]
 
-    def _get_services_for_3pn(self, protocol: str) -> List[ApplicationService]:
+    def _get_services_for_3pn(self, protocol: str) -> list[ApplicationService]:
         services = self.store.get_app_services()
         return [s for s in services if s.is_interested_in_protocol(protocol)]
 
@@ -874,9 +867,9 @@ class ApplicationServicesHandler:
         return True
 
     async def claim_e2e_one_time_keys(
-        self, query: Iterable[Tuple[str, str, str, int]]
-    ) -> Tuple[
-        Dict[str, Dict[str, Dict[str, JsonDict]]], List[Tuple[str, str, str, int]]
+        self, query: Iterable[tuple[str, str, str, int]]
+    ) -> tuple[
+        dict[str, dict[str, dict[str, JsonDict]]], list[tuple[str, str, str, int]]
     ]:
         """Claim one time keys from application services.
 
@@ -898,7 +891,7 @@ class ApplicationServicesHandler:
         services = self.store.get_app_services()
 
         # Partition the users by appservice.
-        query_by_appservice: Dict[str, List[Tuple[str, str, str, int]]] = {}
+        query_by_appservice: dict[str, list[tuple[str, str, str, int]]] = {}
         missing = []
         for user_id, device, algorithm, count in query:
             if not self.store.get_if_app_services_interested_in_user(user_id):
@@ -931,7 +924,7 @@ class ApplicationServicesHandler:
 
         # Patch together the results -- they are all independent (since they
         # require exclusive control over the users, which is the outermost key).
-        claimed_keys: Dict[str, Dict[str, Dict[str, JsonDict]]] = {}
+        claimed_keys: dict[str, dict[str, dict[str, JsonDict]]] = {}
         for success, result in results:
             if success:
                 claimed_keys.update(result[0])
@@ -940,8 +933,8 @@ class ApplicationServicesHandler:
         return claimed_keys, missing
 
     async def query_keys(
-        self, query: Mapping[str, Optional[List[str]]]
-    ) -> Dict[str, Dict[str, Dict[str, JsonDict]]]:
+        self, query: Mapping[str, list[str] | None]
+    ) -> dict[str, dict[str, dict[str, JsonDict]]]:
         """Query application services for device keys.
 
         Users which are exclusively owned by an application service are queried
@@ -956,7 +949,7 @@ class ApplicationServicesHandler:
         services = self.store.get_app_services()
 
         # Partition the users by appservice.
-        query_by_appservice: Dict[str, Dict[str, List[str]]] = {}
+        query_by_appservice: dict[str, dict[str, list[str]]] = {}
         for user_id, device_ids in query.items():
             if not self.store.get_if_app_services_interested_in_user(user_id):
                 continue
@@ -988,7 +981,7 @@ class ApplicationServicesHandler:
         # Patch together the results -- they are all independent (since they
         # require exclusive control over the users). They get returned as a single
         # dictionary.
-        key_queries: Dict[str, Dict[str, Dict[str, JsonDict]]] = {}
+        key_queries: dict[str, dict[str, dict[str, JsonDict]]] = {}
         for success, result in results:
             if success:
                 key_queries.update(result)
diff --git a/synapse/handlers/auth.py b/synapse/handlers/auth.py
index 2d1990cce5..d9355d33da 100644
--- a/synapse/handlers/auth.py
+++ b/synapse/handlers/auth.py
@@ -31,14 +31,8 @@ from typing import (
     Any,
     Awaitable,
     Callable,
-    Dict,
     Iterable,
-    List,
     Mapping,
-    Optional,
-    Tuple,
-    Type,
-    Union,
     cast,
 )
 
@@ -102,7 +96,7 @@ invalid_login_token_counter = Counter(
 
 def convert_client_dict_legacy_fields_to_identifier(
     submission: JsonDict,
-) -> Dict[str, str]:
+) -> dict[str, str]:
     """
     Convert a legacy-formatted login submission to an identifier dict.
 
@@ -154,7 +148,7 @@ def convert_client_dict_legacy_fields_to_identifier(
     return identifier
 
 
-def login_id_phone_to_thirdparty(identifier: JsonDict) -> Dict[str, str]:
+def login_id_phone_to_thirdparty(identifier: JsonDict) -> dict[str, str]:
     """
     Convert a phone login identifier type to a generic threepid identifier.
 
@@ -205,7 +199,7 @@ class AuthHandler:
         self.auth = hs.get_auth()
         self.auth_blocking = hs.get_auth_blocking()
         self.clock = hs.get_clock()
-        self.checkers: Dict[str, UserInteractiveAuthChecker] = {}
+        self.checkers: dict[str, UserInteractiveAuthChecker] = {}
         for auth_checker_class in INTERACTIVE_AUTH_CHECKERS:
             inst = auth_checker_class(hs)
             if inst.is_enabled():
@@ -280,7 +274,7 @@ class AuthHandler:
 
         # A mapping of user ID to extra attributes to include in the login
         # response.
-        self._extra_attributes: Dict[str, SsoLoginExtraAttributes] = {}
+        self._extra_attributes: dict[str, SsoLoginExtraAttributes] = {}
 
         self._auth_delegation_enabled = (
             hs.config.mas.enabled or hs.config.experimental.msc3861.enabled
@@ -290,10 +284,10 @@ class AuthHandler:
         self,
         requester: Requester,
         request: SynapseRequest,
-        request_body: Dict[str, Any],
+        request_body: dict[str, Any],
         description: str,
         can_skip_ui_auth: bool = False,
-    ) -> Tuple[dict, Optional[str]]:
+    ) -> tuple[dict, str | None]:
         """
         Checks that the user is who they claim to be, via a UI auth.
 
@@ -440,12 +434,12 @@ class AuthHandler:
 
     async def check_ui_auth(
         self,
-        flows: List[List[str]],
+        flows: list[list[str]],
         request: SynapseRequest,
-        clientdict: Dict[str, Any],
+        clientdict: dict[str, Any],
         description: str,
-        get_new_session_data: Optional[Callable[[], JsonDict]] = None,
-    ) -> Tuple[dict, dict, str]:
+        get_new_session_data: Callable[[], JsonDict] | None = None,
+    ) -> tuple[dict, dict, str]:
         """
         Takes a dictionary sent by the client in the login / registration
         protocol and handles the User-Interactive Auth flow.
@@ -491,7 +485,7 @@ class AuthHandler:
                 all the stages in any of the permitted flows.
         """
 
-        sid: Optional[str] = None
+        sid: str | None = None
         authdict = clientdict.pop("auth", {})
         if "session" in authdict:
             sid = authdict["session"]
@@ -579,7 +573,7 @@ class AuthHandler:
             )
 
         # check auth type currently being presented
-        errordict: Dict[str, Any] = {}
+        errordict: dict[str, Any] = {}
         if "type" in authdict:
             login_type: str = authdict["type"]
             try:
@@ -617,7 +611,7 @@ class AuthHandler:
         raise InteractiveAuthIncompleteError(session.session_id, ret)
 
     async def add_oob_auth(
-        self, stagetype: str, authdict: Dict[str, Any], clientip: str
+        self, stagetype: str, authdict: dict[str, Any], clientip: str
     ) -> None:
         """
         Adds the result of out-of-band authentication into an existing auth
@@ -641,7 +635,7 @@ class AuthHandler:
             authdict["session"], stagetype, result
         )
 
-    def get_session_id(self, clientdict: Dict[str, Any]) -> Optional[str]:
+    def get_session_id(self, clientdict: dict[str, Any]) -> str | None:
         """
         Gets the session ID for a client given the client dictionary
 
@@ -677,7 +671,7 @@ class AuthHandler:
             raise SynapseError(400, "Unknown session ID: %s" % (session_id,))
 
     async def get_session_data(
-        self, session_id: str, key: str, default: Optional[Any] = None
+        self, session_id: str, key: str, default: Any | None = None
     ) -> Any:
         """
         Retrieve data stored with set_session_data
@@ -702,8 +696,8 @@ class AuthHandler:
         await self.store.delete_old_ui_auth_sessions(expiration_time)
 
     async def _check_auth_dict(
-        self, authdict: Dict[str, Any], clientip: str
-    ) -> Union[Dict[str, Any], str]:
+        self, authdict: dict[str, Any], clientip: str
+    ) -> dict[str, Any] | str:
         """Attempt to validate the auth dict provided by a client
 
         Args:
@@ -750,9 +744,9 @@ class AuthHandler:
 
     def _auth_dict_for_flows(
         self,
-        flows: List[List[str]],
+        flows: list[list[str]],
         session_id: str,
-    ) -> Dict[str, Any]:
+    ) -> dict[str, Any]:
         public_flows = []
         for f in flows:
             public_flows.append(f)
@@ -762,7 +756,7 @@ class AuthHandler:
             LoginType.TERMS: self._get_params_terms,
         }
 
-        params: Dict[str, Any] = {}
+        params: dict[str, Any] = {}
 
         for f in public_flows:
             for stage in f:
@@ -778,9 +772,9 @@ class AuthHandler:
     async def refresh_token(
         self,
         refresh_token: str,
-        access_token_valid_until_ms: Optional[int],
-        refresh_token_valid_until_ms: Optional[int],
-    ) -> Tuple[str, str, Optional[int]]:
+        access_token_valid_until_ms: int | None,
+        refresh_token_valid_until_ms: int | None,
+    ) -> tuple[str, str, int | None]:
         """
         Consumes a refresh token and generate both a new access token and a new refresh token from it.
 
@@ -913,8 +907,8 @@ class AuthHandler:
         self,
         user_id: str,
         duration_ms: int = (2 * 60 * 1000),
-        auth_provider_id: Optional[str] = None,
-        auth_provider_session_id: Optional[str] = None,
+        auth_provider_id: str | None = None,
+        auth_provider_session_id: str | None = None,
     ) -> str:
         login_token = self.generate_login_token()
         now = self._clock.time_msec()
@@ -932,9 +926,9 @@ class AuthHandler:
         self,
         user_id: str,
         device_id: str,
-        expiry_ts: Optional[int],
-        ultimate_session_expiry_ts: Optional[int],
-    ) -> Tuple[str, int]:
+        expiry_ts: int | None,
+        ultimate_session_expiry_ts: int | None,
+    ) -> tuple[str, int]:
         """
         Creates a new refresh token for the user with the given user ID.
 
@@ -965,11 +959,11 @@ class AuthHandler:
     async def create_access_token_for_user_id(
         self,
         user_id: str,
-        device_id: Optional[str],
-        valid_until_ms: Optional[int],
-        puppets_user_id: Optional[str] = None,
+        device_id: str | None,
+        valid_until_ms: int | None,
+        puppets_user_id: str | None = None,
         is_appservice_ghost: bool = False,
-        refresh_token_id: Optional[int] = None,
+        refresh_token_id: int | None = None,
     ) -> str:
         """
         Creates a new access token for the user with the given user ID.
@@ -1038,7 +1032,7 @@ class AuthHandler:
 
         return access_token
 
-    async def check_user_exists(self, user_id: str) -> Optional[str]:
+    async def check_user_exists(self, user_id: str) -> str | None:
         """
         Checks to see if a user with the given id exists. Will check case
         insensitively, but return None if there are multiple inexact matches.
@@ -1065,9 +1059,7 @@ class AuthHandler:
         """
         return await self.store.is_user_approved(user_id)
 
-    async def _find_user_id_and_pwd_hash(
-        self, user_id: str
-    ) -> Optional[Tuple[str, str]]:
+    async def _find_user_id_and_pwd_hash(self, user_id: str) -> tuple[str, str] | None:
         """Checks to see if a user with the given id exists. Will check case
         insensitively, but will return None if there are multiple inexact
         matches.
@@ -1142,10 +1134,10 @@ class AuthHandler:
 
     async def validate_login(
         self,
-        login_submission: Dict[str, Any],
+        login_submission: dict[str, Any],
         ratelimit: bool = False,
         is_reauth: bool = False,
-    ) -> Tuple[str, Optional[Callable[["LoginResponse"], Awaitable[None]]]]:
+    ) -> tuple[str, Callable[["LoginResponse"], Awaitable[None]] | None]:
         """Authenticates the user for the /login API
 
         Also used by the user-interactive auth flow to validate auth types which don't
@@ -1300,8 +1292,8 @@ class AuthHandler:
     async def _validate_userid_login(
         self,
         username: str,
-        login_submission: Dict[str, Any],
-    ) -> Tuple[str, Optional[Callable[["LoginResponse"], Awaitable[None]]]]:
+        login_submission: dict[str, Any],
+    ) -> tuple[str, Callable[["LoginResponse"], Awaitable[None]] | None]:
         """Helper for validate_login
 
         Handles login, once we've mapped 3pids onto userids
@@ -1390,7 +1382,7 @@ class AuthHandler:
 
     async def check_password_provider_3pid(
         self, medium: str, address: str, password: str
-    ) -> Tuple[Optional[str], Optional[Callable[["LoginResponse"], Awaitable[None]]]]:
+    ) -> tuple[str | None, Callable[["LoginResponse"], Awaitable[None]] | None]:
         """Check if a password provider is able to validate a thirdparty login
 
         Args:
@@ -1417,7 +1409,7 @@ class AuthHandler:
         # if result is None then return (None, None)
         return None, None
 
-    async def _check_local_password(self, user_id: str, password: str) -> Optional[str]:
+    async def _check_local_password(self, user_id: str, password: str) -> str | None:
         """Authenticate a user against the local password database.
 
         user_id is checked case insensitively, but will return None if there are
@@ -1532,8 +1524,8 @@ class AuthHandler:
     async def delete_access_tokens_for_user(
         self,
         user_id: str,
-        except_token_id: Optional[int] = None,
-        device_id: Optional[str] = None,
+        except_token_id: int | None = None,
+        device_id: str | None = None,
     ) -> None:
         """Invalidate access tokens belonging to a user
 
@@ -1683,16 +1675,28 @@ class AuthHandler:
             # Normalise the Unicode in the password
             pw = unicodedata.normalize("NFKC", password)
 
+            bytes_to_hash = pw.encode(
+                "utf8"
+            ) + self.hs.config.auth.password_pepper.encode("utf8")
+            if len(bytes_to_hash) > 72:
+                # bcrypt only looks at the first 72 bytes.
+                #
+                # Note: we explicitly DO NOT log the length of the user's password here.
+                logger.debug(
+                    "Password + pepper is too long; truncating to 72 bytes for bcrypt. "
+                    "This is expected behaviour and will not affect a user's ability to log in. 72 bytes is "
+                    "sufficient entropy for a password."
+                )
+                bytes_to_hash = bytes_to_hash[:72]
+
             return bcrypt.hashpw(
-                pw.encode("utf8") + self.hs.config.auth.password_pepper.encode("utf8"),
+                bytes_to_hash,
                 bcrypt.gensalt(self.bcrypt_rounds),
             ).decode("ascii")
 
         return await defer_to_thread(self.hs.get_reactor(), _do_hash)
 
-    async def validate_hash(
-        self, password: str, stored_hash: Union[bytes, str]
-    ) -> bool:
+    async def validate_hash(self, password: str, stored_hash: bytes | str) -> bool:
         """Validates that self.hash(password) == stored_hash.
 
         Args:
@@ -1706,9 +1710,20 @@ class AuthHandler:
         def _do_validate_hash(checked_hash: bytes) -> bool:
             # Normalise the Unicode in the password
             pw = unicodedata.normalize("NFKC", password)
+            password_pepper = self.hs.config.auth.password_pepper
+
+            bytes_to_hash = pw.encode("utf8") + password_pepper.encode("utf8")
+            if len(bytes_to_hash) > 72:
+                # bcrypt only looks at the first 72 bytes
+                logger.debug(
+                    "Password + pepper is too long; truncating to 72 bytes for bcrypt. "
+                    "This is expected behaviour and will not affect a user's ability to log in. 72 bytes is "
+                    "sufficient entropy for a password."
+                )
+                bytes_to_hash = bytes_to_hash[:72]
 
             return bcrypt.checkpw(
-                pw.encode("utf8") + self.hs.config.auth.password_pepper.encode("utf8"),
+                bytes_to_hash,
                 checked_hash,
             )
 
@@ -1778,9 +1793,9 @@ class AuthHandler:
         auth_provider_id: str,
         request: Request,
         client_redirect_url: str,
-        extra_attributes: Optional[JsonDict] = None,
+        extra_attributes: JsonDict | None = None,
         new_user: bool = False,
-        auth_provider_session_id: Optional[str] = None,
+        auth_provider_session_id: str | None = None,
     ) -> None:
         """Having figured out a mxid for this user, complete the HTTP request
 
@@ -1891,7 +1906,7 @@ class AuthHandler:
 
         extra_attributes = self._extra_attributes.get(login_result["user_id"])
         if extra_attributes:
-            login_result_dict = cast(Dict[str, Any], login_result)
+            login_result_dict = cast(dict[str, Any], login_result)
             login_result_dict.update(extra_attributes.extra_attributes)
 
     def _expire_sso_extra_attributes(self) -> None:
@@ -1927,7 +1942,7 @@ def load_legacy_password_auth_providers(hs: "HomeServer") -> None:
 
 
 def load_single_legacy_password_auth_provider(
-    module: Type,
+    module: type,
     config: JsonDict,
     api: "ModuleApi",
 ) -> None:
@@ -1939,7 +1954,7 @@ def load_single_legacy_password_auth_provider(
 
     # All methods that the module provides should be async, but this wasn't enforced
     # in the old module system, so we wrap them if needed
-    def async_wrapper(f: Optional[Callable]) -> Optional[Callable[..., Awaitable]]:
+    def async_wrapper(f: Callable | None) -> Callable[..., Awaitable] | None:
         # f might be None if the callback isn't implemented by the module. In this
         # case we don't want to register a callback at all so we return None.
         if f is None:
@@ -1952,7 +1967,7 @@ def load_single_legacy_password_auth_provider(
 
             async def wrapped_check_password(
                 username: str, login_type: str, login_dict: JsonDict
-            ) -> Optional[Tuple[str, Optional[Callable]]]:
+            ) -> tuple[str, Callable | None] | None:
                 # We've already made sure f is not None above, but mypy doesn't do well
                 # across function boundaries so we need to tell it f is definitely not
                 # None.
@@ -1971,12 +1986,12 @@ def load_single_legacy_password_auth_provider(
             return wrapped_check_password
 
         # We need to wrap check_auth as in the old form it could return
-        # just a str, but now it must return Optional[Tuple[str, Optional[Callable]]
+        # just a str, but now it must return tuple[str, Callable | None] | None
         if f.__name__ == "check_auth":
 
             async def wrapped_check_auth(
                 username: str, login_type: str, login_dict: JsonDict
-            ) -> Optional[Tuple[str, Optional[Callable]]]:
+            ) -> tuple[str, Callable | None] | None:
                 # We've already made sure f is not None above, but mypy doesn't do well
                 # across function boundaries so we need to tell it f is definitely not
                 # None.
@@ -1992,12 +2007,12 @@ def load_single_legacy_password_auth_provider(
             return wrapped_check_auth
 
         # We need to wrap check_3pid_auth as in the old form it could return
-        # just a str, but now it must return Optional[Tuple[str, Optional[Callable]]
+        # just a str, but now it must return tuple[str, Callable | None] | None
         if f.__name__ == "check_3pid_auth":
 
             async def wrapped_check_3pid_auth(
                 medium: str, address: str, password: str
-            ) -> Optional[Tuple[str, Optional[Callable]]]:
+            ) -> tuple[str, Callable | None] | None:
                 # We've already made sure f is not None above, but mypy doesn't do well
                 # across function boundaries so we need to tell it f is definitely not
                 # None.
@@ -2012,7 +2027,7 @@ def load_single_legacy_password_auth_provider(
 
             return wrapped_check_3pid_auth
 
-        def run(*args: Tuple, **kwargs: Dict) -> Awaitable:
+        def run(*args: tuple, **kwargs: dict) -> Awaitable:
             # mypy doesn't do well across function boundaries so we need to tell it
             # f is definitely not None.
             assert f is not None
@@ -2023,10 +2038,10 @@ def load_single_legacy_password_auth_provider(
 
     # If the module has these methods implemented, then we pull them out
     # and register them as hooks.
-    check_3pid_auth_hook: Optional[CHECK_3PID_AUTH_CALLBACK] = async_wrapper(
+    check_3pid_auth_hook: CHECK_3PID_AUTH_CALLBACK | None = async_wrapper(
         getattr(provider, "check_3pid_auth", None)
     )
-    on_logged_out_hook: Optional[ON_LOGGED_OUT_CALLBACK] = async_wrapper(
+    on_logged_out_hook: ON_LOGGED_OUT_CALLBACK | None = async_wrapper(
         getattr(provider, "on_logged_out", None)
     )
 
@@ -2064,24 +2079,20 @@ def load_single_legacy_password_auth_provider(
 
 CHECK_3PID_AUTH_CALLBACK = Callable[
     [str, str, str],
-    Awaitable[
-        Optional[Tuple[str, Optional[Callable[["LoginResponse"], Awaitable[None]]]]]
-    ],
+    Awaitable[tuple[str, Callable[["LoginResponse"], Awaitable[None]] | None] | None],
 ]
-ON_LOGGED_OUT_CALLBACK = Callable[[str, Optional[str], str], Awaitable]
+ON_LOGGED_OUT_CALLBACK = Callable[[str, str | None, str], Awaitable]
 CHECK_AUTH_CALLBACK = Callable[
     [str, str, JsonDict],
-    Awaitable[
-        Optional[Tuple[str, Optional[Callable[["LoginResponse"], Awaitable[None]]]]]
-    ],
+    Awaitable[tuple[str, Callable[["LoginResponse"], Awaitable[None]] | None] | None],
 ]
 GET_USERNAME_FOR_REGISTRATION_CALLBACK = Callable[
     [JsonDict, JsonDict],
-    Awaitable[Optional[str]],
+    Awaitable[str | None],
 ]
 GET_DISPLAYNAME_FOR_REGISTRATION_CALLBACK = Callable[
     [JsonDict, JsonDict],
-    Awaitable[Optional[str]],
+    Awaitable[str | None],
 ]
 IS_3PID_ALLOWED_CALLBACK = Callable[[str, str, bool], Awaitable[bool]]
 
@@ -2094,36 +2105,33 @@ class PasswordAuthProvider:
 
     def __init__(self) -> None:
         # lists of callbacks
-        self.check_3pid_auth_callbacks: List[CHECK_3PID_AUTH_CALLBACK] = []
-        self.on_logged_out_callbacks: List[ON_LOGGED_OUT_CALLBACK] = []
-        self.get_username_for_registration_callbacks: List[
+        self.check_3pid_auth_callbacks: list[CHECK_3PID_AUTH_CALLBACK] = []
+        self.on_logged_out_callbacks: list[ON_LOGGED_OUT_CALLBACK] = []
+        self.get_username_for_registration_callbacks: list[
             GET_USERNAME_FOR_REGISTRATION_CALLBACK
         ] = []
-        self.get_displayname_for_registration_callbacks: List[
+        self.get_displayname_for_registration_callbacks: list[
             GET_DISPLAYNAME_FOR_REGISTRATION_CALLBACK
         ] = []
-        self.is_3pid_allowed_callbacks: List[IS_3PID_ALLOWED_CALLBACK] = []
+        self.is_3pid_allowed_callbacks: list[IS_3PID_ALLOWED_CALLBACK] = []
 
         # Mapping from login type to login parameters
-        self._supported_login_types: Dict[str, Tuple[str, ...]] = {}
+        self._supported_login_types: dict[str, tuple[str, ...]] = {}
 
         # Mapping from login type to auth checker callbacks
-        self.auth_checker_callbacks: Dict[str, List[CHECK_AUTH_CALLBACK]] = {}
+        self.auth_checker_callbacks: dict[str, list[CHECK_AUTH_CALLBACK]] = {}
 
     def register_password_auth_provider_callbacks(
         self,
-        check_3pid_auth: Optional[CHECK_3PID_AUTH_CALLBACK] = None,
-        on_logged_out: Optional[ON_LOGGED_OUT_CALLBACK] = None,
-        is_3pid_allowed: Optional[IS_3PID_ALLOWED_CALLBACK] = None,
-        auth_checkers: Optional[
-            Dict[Tuple[str, Tuple[str, ...]], CHECK_AUTH_CALLBACK]
-        ] = None,
-        get_username_for_registration: Optional[
-            GET_USERNAME_FOR_REGISTRATION_CALLBACK
-        ] = None,
-        get_displayname_for_registration: Optional[
-            GET_DISPLAYNAME_FOR_REGISTRATION_CALLBACK
-        ] = None,
+        check_3pid_auth: CHECK_3PID_AUTH_CALLBACK | None = None,
+        on_logged_out: ON_LOGGED_OUT_CALLBACK | None = None,
+        is_3pid_allowed: IS_3PID_ALLOWED_CALLBACK | None = None,
+        auth_checkers: dict[tuple[str, tuple[str, ...]], CHECK_AUTH_CALLBACK]
+        | None = None,
+        get_username_for_registration: GET_USERNAME_FOR_REGISTRATION_CALLBACK
+        | None = None,
+        get_displayname_for_registration: GET_DISPLAYNAME_FOR_REGISTRATION_CALLBACK
+        | None = None,
     ) -> None:
         # Register check_3pid_auth callback
         if check_3pid_auth is not None:
@@ -2193,7 +2201,7 @@ class PasswordAuthProvider:
 
     async def check_auth(
         self, username: str, login_type: str, login_dict: JsonDict
-    ) -> Optional[Tuple[str, Optional[Callable[["LoginResponse"], Awaitable[None]]]]]:
+    ) -> tuple[str, Callable[["LoginResponse"], Awaitable[None]] | None] | None:
         """Check if the user has presented valid login credentials
 
         Args:
@@ -2224,14 +2232,14 @@ class PasswordAuthProvider:
                 continue
 
             if result is not None:
-                # Check that the callback returned a Tuple[str, Optional[Callable]]
+                # Check that the callback returned a tuple[str, Callable | None]
                 # "type: ignore[unreachable]" is used after some isinstance checks because mypy thinks
                 # result is always the right type, but as it is 3rd party code it might not be
 
                 if not isinstance(result, tuple) or len(result) != 2:
                     logger.warning(  # type: ignore[unreachable]
                         "Wrong type returned by module API callback %s: %s, expected"
-                        " Optional[Tuple[str, Optional[Callable]]]",
+                        " tuple[str, Callable | None] | None",
                         callback,
                         result,
                     )
@@ -2244,24 +2252,24 @@ class PasswordAuthProvider:
                 if not isinstance(str_result, str):
                     logger.warning(  # type: ignore[unreachable]
                         "Wrong type returned by module API callback %s: %s, expected"
-                        " Optional[Tuple[str, Optional[Callable]]]",
+                        " tuple[str, Callable | None] | None",
                         callback,
                         result,
                     )
                     continue
 
-                # the second should be Optional[Callable]
+                # the second should be Callable | None
                 if callback_result is not None:
                     if not callable(callback_result):
                         logger.warning(  # type: ignore[unreachable]
                             "Wrong type returned by module API callback %s: %s, expected"
-                            " Optional[Tuple[str, Optional[Callable]]]",
+                            " tuple[str, Callable | None] | None",
                             callback,
                             result,
                         )
                         continue
 
-                # The result is a (str, Optional[callback]) tuple so return the successful result
+                # The result is a (str, callback | None) tuple so return the successful result
                 return result
 
         # If this point has been reached then none of the callbacks successfully authenticated
@@ -2270,7 +2278,7 @@ class PasswordAuthProvider:
 
     async def check_3pid_auth(
         self, medium: str, address: str, password: str
-    ) -> Optional[Tuple[str, Optional[Callable[["LoginResponse"], Awaitable[None]]]]]:
+    ) -> tuple[str, Callable[["LoginResponse"], Awaitable[None]] | None] | None:
         # This function is able to return a deferred that either
         # resolves None, meaning authentication failure, or upon
         # success, to a str (which is the user_id) or a tuple of
@@ -2287,14 +2295,14 @@ class PasswordAuthProvider:
                 continue
 
             if result is not None:
-                # Check that the callback returned a Tuple[str, Optional[Callable]]
+                # Check that the callback returned a tuple[str, Callable | None]
                 # "type: ignore[unreachable]" is used after some isinstance checks because mypy thinks
                 # result is always the right type, but as it is 3rd party code it might not be
 
                 if not isinstance(result, tuple) or len(result) != 2:
                     logger.warning(  # type: ignore[unreachable]
                         "Wrong type returned by module API callback %s: %s, expected"
-                        " Optional[Tuple[str, Optional[Callable]]]",
+                        " tuple[str, Callable | None] | None",
                         callback,
                         result,
                     )
@@ -2307,24 +2315,24 @@ class PasswordAuthProvider:
                 if not isinstance(str_result, str):
                     logger.warning(  # type: ignore[unreachable]
                         "Wrong type returned by module API callback %s: %s, expected"
-                        " Optional[Tuple[str, Optional[Callable]]]",
+                        " tuple[str, Callable | None] | None",
                         callback,
                         result,
                     )
                     continue
 
-                # the second should be Optional[Callable]
+                # the second should be Callable | None
                 if callback_result is not None:
                     if not callable(callback_result):
                         logger.warning(  # type: ignore[unreachable]
                             "Wrong type returned by module API callback %s: %s, expected"
-                            " Optional[Tuple[str, Optional[Callable]]]",
+                            " tuple[str, Callable | None] | None",
                             callback,
                             result,
                         )
                         continue
 
-                # The result is a (str, Optional[callback]) tuple so return the successful result
+                # The result is a (str, callback | None) tuple so return the successful result
                 return result
 
         # If this point has been reached then none of the callbacks successfully authenticated
@@ -2332,7 +2340,7 @@ class PasswordAuthProvider:
         return None
 
     async def on_logged_out(
-        self, user_id: str, device_id: Optional[str], access_token: str
+        self, user_id: str, device_id: str | None, access_token: str
     ) -> None:
         # call all of the on_logged_out callbacks
         for callback in self.on_logged_out_callbacks:
@@ -2346,7 +2354,7 @@ class PasswordAuthProvider:
         self,
         uia_results: JsonDict,
         params: JsonDict,
-    ) -> Optional[str]:
+    ) -> str | None:
         """Defines the username to use when registering the user, using the credentials
         and parameters provided during the UIA flow.
 
@@ -2391,7 +2399,7 @@ class PasswordAuthProvider:
         self,
         uia_results: JsonDict,
         params: JsonDict,
-    ) -> Optional[str]:
+    ) -> str | None:
         """Defines the display name to use when registering the user, using the
         credentials and parameters provided during the UIA flow.
 
diff --git a/synapse/handlers/cas.py b/synapse/handlers/cas.py
index fbe79c2e4c..dbcf074d2b 100644
--- a/synapse/handlers/cas.py
+++ b/synapse/handlers/cas.py
@@ -20,7 +20,7 @@
 #
 import logging
 import urllib.parse
-from typing import TYPE_CHECKING, Dict, List, Optional
+from typing import TYPE_CHECKING
 from xml.etree import ElementTree as ET
 
 import attr
@@ -41,7 +41,7 @@ logger = logging.getLogger(__name__)
 class CasError(Exception):
     """Used to catch errors when validating the CAS ticket."""
 
-    def __init__(self, error: str, error_description: Optional[str] = None):
+    def __init__(self, error: str, error_description: str | None = None):
         self.error = error
         self.error_description = error_description
 
@@ -54,7 +54,7 @@ class CasError(Exception):
 @attr.s(slots=True, frozen=True, auto_attribs=True)
 class CasResponse:
     username: str
-    attributes: Dict[str, List[Optional[str]]]
+    attributes: dict[str, list[str | None]]
 
 
 class CasHandler:
@@ -99,7 +99,7 @@ class CasHandler:
 
         self._sso_handler.register_identity_provider(self)
 
-    def _build_service_param(self, args: Dict[str, str]) -> str:
+    def _build_service_param(self, args: dict[str, str]) -> str:
         """
         Generates a value to use as the "service" parameter when redirecting or
         querying the CAS service.
@@ -116,7 +116,7 @@ class CasHandler:
         )
 
     async def _validate_ticket(
-        self, ticket: str, service_args: Dict[str, str]
+        self, ticket: str, service_args: dict[str, str]
     ) -> CasResponse:
         """
         Validate a CAS ticket with the server, and return the parsed the response.
@@ -145,7 +145,7 @@ class CasHandler:
         except PartialDownloadError as pde:
             # Twisted raises this error if the connection is closed,
             # even if that's being used old-http style to signal end-of-data
-            # Assertion is for mypy's benefit. Error.response is Optional[bytes],
+            # Assertion is for mypy's benefit. Error.response is bytes | None,
             # but a PartialDownloadError should always have a non-None response.
             assert pde.response is not None
             body = pde.response
@@ -186,7 +186,7 @@ class CasHandler:
 
         # Iterate through the nodes and pull out the user and any extra attributes.
         user = None
-        attributes: Dict[str, List[Optional[str]]] = {}
+        attributes: dict[str, list[str | None]] = {}
         for child in root[0]:
             if child.tag.endswith("user"):
                 user = child.text
@@ -213,8 +213,8 @@ class CasHandler:
     async def handle_redirect_request(
         self,
         request: SynapseRequest,
-        client_redirect_url: Optional[bytes],
-        ui_auth_session_id: Optional[str] = None,
+        client_redirect_url: bytes | None,
+        ui_auth_session_id: str | None = None,
     ) -> str:
         """Generates a URL for the CAS server where the client should be redirected.
 
@@ -245,8 +245,8 @@ class CasHandler:
         self,
         request: SynapseRequest,
         ticket: str,
-        client_redirect_url: Optional[str],
-        session: Optional[str],
+        client_redirect_url: str | None,
+        session: str | None,
     ) -> None:
         """
         Called once the user has successfully authenticated with the SSO.
@@ -292,8 +292,8 @@ class CasHandler:
         self,
         request: SynapseRequest,
         cas_response: CasResponse,
-        client_redirect_url: Optional[str],
-        session: Optional[str],
+        client_redirect_url: str | None,
+        session: str | None,
     ) -> None:
         """Handle a CAS response to a ticket request.
 
@@ -384,7 +384,7 @@ class CasHandler:
 
             return UserAttributes(localpart=localpart, display_name=display_name)
 
-        async def grandfather_existing_users() -> Optional[str]:
+        async def grandfather_existing_users() -> str | None:
             # Since CAS did not always use the user_external_ids table, always
             # to attempt to map to existing users.
             user_id = UserID(localpart, self._hostname).to_string()
diff --git a/synapse/handlers/deactivate_account.py b/synapse/handlers/deactivate_account.py
index c0684380a7..e4c646ce87 100644
--- a/synapse/handlers/deactivate_account.py
+++ b/synapse/handlers/deactivate_account.py
@@ -20,11 +20,10 @@
 #
 import itertools
 import logging
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING
 
 from synapse.api.constants import Membership
 from synapse.api.errors import SynapseError
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.replication.http.deactivate_account import (
     ReplicationNotifyAccountDeactivatedServlet,
 )
@@ -77,7 +76,7 @@ class DeactivateAccountHandler:
         user_id: str,
         erase_data: bool,
         requester: Requester,
-        id_server: Optional[str] = None,
+        id_server: str | None = None,
         by_admin: bool = False,
     ) -> bool:
         """Deactivate a user's account
@@ -272,8 +271,8 @@ class DeactivateAccountHandler:
         pending deactivation, if it isn't already running.
         """
         if not self._user_parter_running:
-            run_as_background_process(
-                "user_parter_loop", self.server_name, self._user_parter_loop
+            self.hs.run_as_background_process(
+                "user_parter_loop", self._user_parter_loop
             )
 
     async def _user_parter_loop(self) -> None:
diff --git a/synapse/handlers/delayed_events.py b/synapse/handlers/delayed_events.py
index d47e3fd263..3342420d7d 100644
--- a/synapse/handlers/delayed_events.py
+++ b/synapse/handlers/delayed_events.py
@@ -13,7 +13,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, List, Optional, Set, Tuple
+from typing import TYPE_CHECKING
 
 from twisted.internet.interfaces import IDelayedCall
 
@@ -24,9 +24,6 @@ from synapse.config.workers import MAIN_PROCESS_INSTANCE_NAME
 from synapse.logging.context import make_deferred_yieldable
 from synapse.logging.opentracing import set_tag
 from synapse.metrics import SERVER_NAME_LABEL, event_processing_positions
-from synapse.metrics.background_process_metrics import (
-    run_as_background_process,
-)
 from synapse.replication.http.delayed_events import (
     ReplicationAddedDelayedEventRestServlet,
 )
@@ -58,6 +55,7 @@ logger = logging.getLogger(__name__)
 
 class DelayedEventsHandler:
     def __init__(self, hs: "HomeServer"):
+        self.hs = hs
         self.server_name = hs.hostname
         self._store = hs.get_datastores().main
         self._storage_controllers = hs.get_storage_controllers()
@@ -76,10 +74,10 @@ class DelayedEventsHandler:
             cfg=self._config.ratelimiting.rc_delayed_event_mgmt,
         )
 
-        self._next_delayed_event_call: Optional[IDelayedCall] = None
+        self._next_delayed_event_call: IDelayedCall | None = None
 
         # The current position in the current_state_delta stream
-        self._event_pos: Optional[int] = None
+        self._event_pos: int | None = None
 
         # Guard to ensure we only process event deltas one at a time
         self._event_processing = False
@@ -94,7 +92,10 @@ class DelayedEventsHandler:
                 hs.get_notifier().add_replication_callback(self.notify_new_event)
                 # Kick off again (without blocking) to catch any missed notifications
                 # that may have fired before the callback was added.
-                self._clock.call_later(0, self.notify_new_event)
+                self._clock.call_later(
+                    0,
+                    self.notify_new_event,
+                )
 
                 # Delayed events that are already marked as processed on startup might not have been
                 # sent properly on the last run of the server, so unmark them to send them again.
@@ -112,15 +113,14 @@ class DelayedEventsHandler:
                     self._schedule_next_at(next_send_ts)
 
                 # Can send the events in background after having awaited on marking them as processed
-                run_as_background_process(
+                self.hs.run_as_background_process(
                     "_send_events",
-                    self.server_name,
                     self._send_events,
                     events,
                 )
 
-            self._initialized_from_db = run_as_background_process(
-                "_schedule_db_events", self.server_name, _schedule_db_events
+            self._initialized_from_db = self.hs.run_as_background_process(
+                "_schedule_db_events", _schedule_db_events
             )
         else:
             self._repl_client = ReplicationAddedDelayedEventRestServlet.make_client(hs)
@@ -145,9 +145,7 @@ class DelayedEventsHandler:
             finally:
                 self._event_processing = False
 
-        run_as_background_process(
-            "delayed_events.notify_new_event", self.server_name, process
-        )
+        self.hs.run_as_background_process("delayed_events.notify_new_event", process)
 
     async def _unsafe_process_new_event(self) -> None:
         # We purposefully fetch the current max room stream ordering before
@@ -228,7 +226,7 @@ class DelayedEventsHandler:
 
                 await self._store.update_delayed_events_stream_pos(max_pos)
 
-    async def _handle_state_deltas(self, deltas: List[StateDelta]) -> None:
+    async def _handle_state_deltas(self, deltas: list[StateDelta]) -> None:
         """
         Process current state deltas to cancel other users' pending delayed events
         that target the same state.
@@ -329,8 +327,8 @@ class DelayedEventsHandler:
         *,
         room_id: str,
         event_type: str,
-        state_key: Optional[str],
-        origin_server_ts: Optional[int],
+        state_key: str | None,
+        origin_server_ts: int | None,
         content: JsonDict,
         delay: int,
     ) -> str:
@@ -504,8 +502,8 @@ class DelayedEventsHandler:
 
         await self._send_events(events)
 
-    async def _send_events(self, events: List[DelayedEventDetails]) -> None:
-        sent_state: Set[Tuple[RoomID, EventType, StateKey]] = set()
+    async def _send_events(self, events: list[DelayedEventDetails]) -> None:
+        sent_state: set[tuple[RoomID, EventType, StateKey]] = set()
         for event in events:
             if event.state_key is not None:
                 state_info = (event.room_id, event.type, event.state_key)
@@ -528,7 +526,7 @@ class DelayedEventsHandler:
                     state_key=state_key,
                 )
 
-    def _schedule_next_at_or_none(self, next_send_ts: Optional[Timestamp]) -> None:
+    def _schedule_next_at_or_none(self, next_send_ts: Timestamp | None) -> None:
         if next_send_ts is not None:
             self._schedule_next_at(next_send_ts)
         elif self._next_delayed_event_call is not None:
@@ -542,15 +540,14 @@ class DelayedEventsHandler:
         if self._next_delayed_event_call is None:
             self._next_delayed_event_call = self._clock.call_later(
                 delay_sec,
-                run_as_background_process,
+                self.hs.run_as_background_process,
                 "_send_on_timeout",
-                self.server_name,
                 self._send_on_timeout,
             )
         else:
             self._next_delayed_event_call.reset(delay_sec)
 
-    async def get_all_for_user(self, requester: Requester) -> List[JsonDict]:
+    async def get_all_for_user(self, requester: Requester) -> list[JsonDict]:
         """Return all pending delayed events requested by the given user."""
         await self._delayed_event_mgmt_ratelimiter.ratelimit(
             requester,
@@ -563,7 +560,7 @@ class DelayedEventsHandler:
     async def _send_event(
         self,
         event: DelayedEventDetails,
-        txn_id: Optional[str] = None,
+        txn_id: str | None = None,
     ) -> None:
         user_id = UserID(event.user_localpart, self._config.server.server_name)
         user_id_str = user_id.to_string()
@@ -625,7 +622,7 @@ class DelayedEventsHandler:
     def _get_current_ts(self) -> Timestamp:
         return Timestamp(self._clock.time_msec())
 
-    def _next_send_ts_changed(self, next_send_ts: Optional[Timestamp]) -> bool:
+    def _next_send_ts_changed(self, next_send_ts: Timestamp | None) -> bool:
         # The DB alone knows if the next send time changed after adding/modifying
         # a delayed event, but if we were to ever miss updating our delayed call's
         # firing time, we may miss other updates. So, keep track of changes to the
diff --git a/synapse/handlers/device.py b/synapse/handlers/device.py
index 9509ac422e..3f1a5fe6d6 100644
--- a/synapse/handlers/device.py
+++ b/synapse/handlers/device.py
@@ -25,13 +25,8 @@ from threading import Lock
 from typing import (
     TYPE_CHECKING,
     AbstractSet,
-    Dict,
     Iterable,
-    List,
     Mapping,
-    Optional,
-    Set,
-    Tuple,
     cast,
 )
 
@@ -47,7 +42,6 @@ from synapse.api.errors import (
 )
 from synapse.logging.opentracing import log_kv, set_tag, trace
 from synapse.metrics.background_process_metrics import (
-    run_as_background_process,
     wrap_as_background_process,
 )
 from synapse.replication.http.devices import (
@@ -94,7 +88,7 @@ MAX_DEVICE_DISPLAY_NAME_LEN = 100
 DELETE_STALE_DEVICES_INTERVAL_MS = 24 * 60 * 60 * 1000
 
 
-def _check_device_name_length(name: Optional[str]) -> None:
+def _check_device_name_length(name: str | None) -> None:
     """
     Checks whether a device name is longer than the maximum allowed length.
 
@@ -125,7 +119,7 @@ class DeviceHandler:
     def __init__(self, hs: "HomeServer"):
         self.server_name = hs.hostname  # nb must be called this for @measure_func
         self.clock = hs.get_clock()  # nb must be called this for @measure_func
-        self.hs = hs
+        self.hs = hs  # nb must be called this for @wrap_as_background_process
         self.store = cast("GenericWorkerStore", hs.get_datastores().main)
         self.notifier = hs.get_notifier()
         self.state = hs.get_state_handler()
@@ -191,10 +185,9 @@ class DeviceHandler:
             and self._delete_stale_devices_after is not None
         ):
             self.clock.looping_call(
-                run_as_background_process,
+                self.hs.run_as_background_process,
                 DELETE_STALE_DEVICES_INTERVAL_MS,
                 desc="delete_stale_devices",
-                server_name=self.server_name,
                 func=self._delete_stale_devices,
             )
 
@@ -214,10 +207,10 @@ class DeviceHandler:
     async def check_device_registered(
         self,
         user_id: str,
-        device_id: Optional[str],
-        initial_device_display_name: Optional[str] = None,
-        auth_provider_id: Optional[str] = None,
-        auth_provider_session_id: Optional[str] = None,
+        device_id: str | None,
+        initial_device_display_name: str | None = None,
+        auth_provider_id: str | None = None,
+        auth_provider_session_id: str | None = None,
     ) -> str:
         """
         If the given device has not been registered, register it with the
@@ -275,7 +268,7 @@ class DeviceHandler:
 
     @trace
     async def delete_all_devices_for_user(
-        self, user_id: str, except_device_id: Optional[str] = None
+        self, user_id: str, except_device_id: str | None = None
     ) -> None:
         """Delete all of the user's devices
 
@@ -350,7 +343,7 @@ class DeviceHandler:
         await self.notify_device_update(user_id, device_ids)
 
     async def upsert_device(
-        self, user_id: str, device_id: str, display_name: Optional[str] = None
+        self, user_id: str, device_id: str, display_name: str | None = None
     ) -> bool:
         """Create or update a device
 
@@ -409,7 +402,7 @@ class DeviceHandler:
                 raise
 
     @trace
-    async def get_devices_by_user(self, user_id: str) -> List[JsonDict]:
+    async def get_devices_by_user(self, user_id: str) -> list[JsonDict]:
         """
         Retrieve the given user's devices
 
@@ -431,9 +424,7 @@ class DeviceHandler:
         log_kv(device_map)
         return devices
 
-    async def get_dehydrated_device(
-        self, user_id: str
-    ) -> Optional[Tuple[str, JsonDict]]:
+    async def get_dehydrated_device(self, user_id: str) -> tuple[str, JsonDict] | None:
         """Retrieve the information for a dehydrated device.
 
         Args:
@@ -447,10 +438,10 @@ class DeviceHandler:
     async def store_dehydrated_device(
         self,
         user_id: str,
-        device_id: Optional[str],
+        device_id: str | None,
         device_data: JsonDict,
-        initial_device_display_name: Optional[str] = None,
-        keys_for_device: Optional[JsonDict] = None,
+        initial_device_display_name: str | None = None,
+        keys_for_device: JsonDict | None = None,
     ) -> str:
         """Store a dehydrated device for a user, optionally storing the keys associated with
         it as well.  If the user had a previous dehydrated device, it is removed.
@@ -569,8 +560,8 @@ class DeviceHandler:
         user_id: str,
         room_ids: StrCollection,
         from_token: StreamToken,
-        now_token: Optional[StreamToken] = None,
-    ) -> Set[str]:
+        now_token: StreamToken | None = None,
+    ) -> set[str]:
         """Get the set of users whose devices have changed who share a room with
         the given user.
         """
@@ -646,8 +637,8 @@ class DeviceHandler:
         # Check for newly joined or left rooms. We need to make sure that we add
         # to newly joined in the case membership goes from join -> leave -> join
         # again.
-        newly_joined_rooms: Set[str] = set()
-        newly_left_rooms: Set[str] = set()
+        newly_joined_rooms: set[str] = set()
+        newly_left_rooms: set[str] = set()
         for change in membership_changes:
             # We check for changes in "joinedness", i.e. if the membership has
             # changed to or from JOIN.
@@ -663,10 +654,10 @@ class DeviceHandler:
         # the user is currently in.
 
         # List of membership changes per room
-        room_to_deltas: Dict[str, List[StateDelta]] = {}
+        room_to_deltas: dict[str, list[StateDelta]] = {}
         # The set of event IDs of membership events (so we can fetch their
         # associated membership).
-        memberships_to_fetch: Set[str] = set()
+        memberships_to_fetch: set[str] = set()
 
         # TODO: Only pull out membership events?
         state_changes = await self.store.get_current_state_deltas_for_rooms(
@@ -683,7 +674,7 @@ class DeviceHandler:
                 memberships_to_fetch.add(delta.prev_event_id)
 
         # Fetch all the memberships for the membership events
-        event_id_to_memberships: Mapping[str, Optional[EventIdMembership]] = {}
+        event_id_to_memberships: Mapping[str, EventIdMembership | None] = {}
         if memberships_to_fetch:
             event_id_to_memberships = await self.store.get_membership_from_event_ids(
                 memberships_to_fetch
@@ -697,8 +688,8 @@ class DeviceHandler:
 
         # We now want to find any user that have newly joined/invited/knocked,
         # or newly left, similarly to above.
-        newly_joined_or_invited_or_knocked_users: Set[str] = set()
-        newly_left_users: Set[str] = set()
+        newly_joined_or_invited_or_knocked_users: set[str] = set()
+        newly_left_users: set[str] = set()
         for _, deltas in room_to_deltas.items():
             for delta in deltas:
                 # Get the prev/new memberships for the delta
@@ -840,7 +831,7 @@ class DeviceHandler:
         # Check if the application services have any results.
         if self._query_appservices_for_keys:
             # Query the appservice for all devices for this user.
-            query: Dict[str, Optional[List[str]]] = {user_id: None}
+            query: dict[str, list[str] | None] = {user_id: None}
 
             # Query the appservices for any keys.
             appservice_results = await self._appservice_handler.query_keys(query)
@@ -900,7 +891,7 @@ class DeviceHandler:
     async def notify_user_signature_update(
         self,
         from_user_id: str,
-        user_ids: List[str],
+        user_ids: list[str],
     ) -> None:
         """Notify a device writer that a user have made new signatures of other users.
 
@@ -929,7 +920,7 @@ class DeviceHandler:
     async def _delete_device_messages(
         self,
         task: ScheduledTask,
-    ) -> Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]:
+    ) -> tuple[TaskStatus, JsonMapping | None, str | None]:
         """Scheduler task to delete device messages in batch of `DEVICE_MSGS_DELETE_BATCH_LIMIT`."""
         assert task.params is not None
         user_id = task.params["user_id"]
@@ -963,10 +954,9 @@ class DeviceWriterHandler(DeviceHandler):
 
     def __init__(self, hs: "HomeServer"):
         super().__init__(hs)
+        self.server_name = hs.hostname  # nb must be called this for @measure_func
+        self.hs = hs  # nb must be called this for @wrap_as_background_process
 
-        self.server_name = (
-            hs.hostname
-        )  # nb must be called this for @measure_func and @wrap_as_background_process
         # We only need to poke the federation sender explicitly if its on the
         # same instance. Other federation sender instances will get notified by
         # `synapse.app.generic_worker.FederationSenderHandler` when it sees it
@@ -1054,7 +1044,7 @@ class DeviceWriterHandler(DeviceHandler):
             await self.handle_new_device_update()
 
     async def notify_user_signature_update(
-        self, from_user_id: str, user_ids: List[str]
+        self, from_user_id: str, user_ids: list[str]
     ) -> None:
         """Notify a user that they have made new signatures of other users.
 
@@ -1115,7 +1105,7 @@ class DeviceWriterHandler(DeviceHandler):
         # hosts we've already poked about for this update. This is so that we
         # don't poke the same remote server about the same update repeatedly.
         current_stream_id = None
-        hosts_already_sent_to: Set[str] = set()
+        hosts_already_sent_to: set[str] = set()
 
         try:
             stream_id, room_id = await self.store.get_device_change_last_converted_pos()
@@ -1314,7 +1304,7 @@ class DeviceWriterHandler(DeviceHandler):
 
 
 def _update_device_from_client_ips(
-    device: JsonDict, client_ips: Mapping[Tuple[str, str], DeviceLastConnectionInfo]
+    device: JsonDict, client_ips: Mapping[tuple[str, str], DeviceLastConnectionInfo]
 ) -> None:
     ip = client_ips.get((device["user_id"], device["device_id"]))
     device.update(
@@ -1341,8 +1331,8 @@ class DeviceListWorkerUpdater:
 
     async def multi_user_device_resync(
         self,
-        user_ids: List[str],
-    ) -> Dict[str, Optional[JsonMapping]]:
+        user_ids: list[str],
+    ) -> dict[str, JsonMapping | None]:
         """
         Like `user_device_resync` but operates on multiple users **from the same origin**
         at once.
@@ -1366,9 +1356,9 @@ class DeviceListWorkerUpdater:
     async def process_cross_signing_key_update(
         self,
         user_id: str,
-        master_key: Optional[JsonDict],
-        self_signing_key: Optional[JsonDict],
-    ) -> List[str]:
+        master_key: JsonDict | None,
+        self_signing_key: JsonDict | None,
+    ) -> list[str]:
         """Process the given new master and self-signing key for the given remote user.
 
         Args:
@@ -1444,7 +1434,7 @@ class DeviceListUpdater(DeviceListWorkerUpdater):
     def __init__(self, hs: "HomeServer", device_handler: DeviceWriterHandler):
         super().__init__(hs)
 
-        self.server_name = hs.hostname
+        self.hs = hs
         self.federation = hs.get_federation_client()
         self.server_name = hs.hostname  # nb must be called this for @measure_func
         self.clock = hs.get_clock()  # nb must be called this for @measure_func
@@ -1458,16 +1448,17 @@ class DeviceListUpdater(DeviceListWorkerUpdater):
         )
 
         # user_id -> list of updates waiting to be handled.
-        self._pending_updates: Dict[
-            str, List[Tuple[str, str, Iterable[str], JsonDict]]
+        self._pending_updates: dict[
+            str, list[tuple[str, str, Iterable[str], JsonDict]]
         ] = {}
 
         # Recently seen stream ids. We don't bother keeping these in the DB,
         # but they're useful to have them about to reduce the number of spurious
         # resyncs.
-        self._seen_updates: ExpiringCache[str, Set[str]] = ExpiringCache(
+        self._seen_updates: ExpiringCache[str, set[str]] = ExpiringCache(
             cache_name="device_update_edu",
             server_name=self.server_name,
+            hs=self.hs,
             clock=self.clock,
             max_len=10000,
             expiry_ms=30 * 60 * 1000,
@@ -1477,9 +1468,8 @@ class DeviceListUpdater(DeviceListWorkerUpdater):
         # Attempt to resync out of sync device lists every 30s.
         self._resync_retry_lock = Lock()
         self.clock.looping_call(
-            run_as_background_process,
+            self.hs.run_as_background_process,
             30 * 1000,
-            server_name=self.server_name,
             func=self._maybe_retry_device_resync,
             desc="_maybe_retry_device_resync",
         )
@@ -1599,9 +1589,8 @@ class DeviceListUpdater(DeviceListWorkerUpdater):
             if resync:
                 # We mark as stale up front in case we get restarted.
                 await self.store.mark_remote_users_device_caches_as_stale([user_id])
-                run_as_background_process(
+                self.hs.run_as_background_process(
                     "_maybe_retry_device_resync",
-                    self.server_name,
                     self.multi_user_device_resync,
                     [user_id],
                     False,
@@ -1623,12 +1612,12 @@ class DeviceListUpdater(DeviceListWorkerUpdater):
                 )
 
     async def _need_to_do_resync(
-        self, user_id: str, updates: Iterable[Tuple[str, str, Iterable[str], JsonDict]]
+        self, user_id: str, updates: Iterable[tuple[str, str, Iterable[str], JsonDict]]
     ) -> bool:
         """Given a list of updates for a user figure out if we need to do a full
         resync, or whether we have enough data that we can just apply the delta.
         """
-        seen_updates: Set[str] = self._seen_updates.get(user_id, set())
+        seen_updates: set[str] = self._seen_updates.get(user_id, set())
 
         extremity = await self.store.get_device_list_last_stream_id_for_remote(user_id)
 
@@ -1706,8 +1695,8 @@ class DeviceListUpdater(DeviceListWorkerUpdater):
             self._resync_retry_lock.release()
 
     async def multi_user_device_resync(
-        self, user_ids: List[str], mark_failed_as_stale: bool = True
-    ) -> Dict[str, Optional[JsonMapping]]:
+        self, user_ids: list[str], mark_failed_as_stale: bool = True
+    ) -> dict[str, JsonMapping | None]:
         """
         Like `user_device_resync` but operates on multiple users **from the same origin**
         at once.
@@ -1743,7 +1732,7 @@ class DeviceListUpdater(DeviceListWorkerUpdater):
 
     async def _user_device_resync_returning_failed(
         self, user_id: str
-    ) -> Tuple[Optional[JsonMapping], bool]:
+    ) -> tuple[JsonMapping | None, bool]:
         """Fetches all devices for a user and updates the device cache with them.
 
         Args:
diff --git a/synapse/handlers/devicemessage.py b/synapse/handlers/devicemessage.py
index 860e24d79d..0ef14b31da 100644
--- a/synapse/handlers/devicemessage.py
+++ b/synapse/handlers/devicemessage.py
@@ -21,7 +21,7 @@
 
 import logging
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Any, Dict, Optional
+from typing import TYPE_CHECKING, Any
 
 from synapse.api.constants import EduTypes, EventContentFields, ToDeviceEventTypes
 from synapse.api.errors import Codes, SynapseError
@@ -158,7 +158,7 @@ class DeviceMessageHandler:
         self,
         message_type: str,
         sender_user_id: str,
-        by_device: Dict[str, Dict[str, Any]],
+        by_device: dict[str, dict[str, Any]],
     ) -> None:
         """Checks inbound device messages for unknown remote devices, and if
         found marks the remote cache for the user as stale.
@@ -207,7 +207,7 @@ class DeviceMessageHandler:
         self,
         requester: Requester,
         message_type: str,
-        messages: Dict[str, Dict[str, JsonDict]],
+        messages: dict[str, dict[str, JsonDict]],
     ) -> None:
         """
         Handle a request from a user to send to-device message(s).
@@ -222,7 +222,7 @@ class DeviceMessageHandler:
         set_tag(SynapseTags.TO_DEVICE_TYPE, message_type)
         set_tag(SynapseTags.TO_DEVICE_SENDER, sender_user_id)
         local_messages = {}
-        remote_messages: Dict[str, Dict[str, Dict[str, JsonDict]]] = {}
+        remote_messages: dict[str, dict[str, dict[str, JsonDict]]] = {}
         for user_id, by_device in messages.items():
             if not UserID.is_valid(user_id):
                 logger.warning(
@@ -315,7 +315,7 @@ class DeviceMessageHandler:
         self,
         requester: Requester,
         device_id: str,
-        since_token: Optional[str],
+        since_token: str | None,
         limit: int,
     ) -> JsonDict:
         """Fetches up to `limit` events sent to `device_id` starting from `since_token`
diff --git a/synapse/handlers/directory.py b/synapse/handlers/directory.py
index 11284ccd0b..03b23fe0be 100644
--- a/synapse/handlers/directory.py
+++ b/synapse/handlers/directory.py
@@ -21,7 +21,7 @@
 
 import logging
 import string
-from typing import TYPE_CHECKING, Iterable, List, Literal, Optional, Sequence
+from typing import TYPE_CHECKING, Iterable, Literal, Sequence
 
 from synapse.api.constants import MAX_ALIAS_LENGTH, EventTypes
 from synapse.api.errors import (
@@ -73,8 +73,8 @@ class DirectoryHandler:
         self,
         room_alias: RoomAlias,
         room_id: str,
-        servers: Optional[Iterable[str]] = None,
-        creator: Optional[str] = None,
+        servers: Iterable[str] | None = None,
+        creator: str | None = None,
     ) -> None:
         # general association creation for both human users and app services
 
@@ -108,7 +108,7 @@ class DirectoryHandler:
         requester: Requester,
         room_alias: RoomAlias,
         room_id: str,
-        servers: Optional[List[str]] = None,
+        servers: list[str] | None = None,
         check_membership: bool = True,
     ) -> None:
         """Attempt to create a new alias
@@ -252,7 +252,7 @@ class DirectoryHandler:
             )
         await self._delete_association(room_alias)
 
-    async def _delete_association(self, room_alias: RoomAlias) -> Optional[str]:
+    async def _delete_association(self, room_alias: RoomAlias) -> str | None:
         if not self.hs.is_mine(room_alias):
             raise SynapseError(400, "Room alias must be local")
 
@@ -263,16 +263,16 @@ class DirectoryHandler:
     async def get_association(self, room_alias: RoomAlias) -> JsonDict:
         room_id = None
         if self.hs.is_mine(room_alias):
-            result: Optional[
-                RoomAliasMapping
-            ] = await self.get_association_from_room_alias(room_alias)
+            result: (
+                RoomAliasMapping | None
+            ) = await self.get_association_from_room_alias(room_alias)
 
             if result:
                 room_id = result.room_id
                 servers = result.servers
         else:
             try:
-                fed_result: Optional[JsonDict] = await self.federation.make_query(
+                fed_result: JsonDict | None = await self.federation.make_query(
                     destination=room_alias.domain,
                     query_type="directory",
                     args={"room_alias": room_alias.to_string()},
@@ -387,7 +387,7 @@ class DirectoryHandler:
 
     async def get_association_from_room_alias(
         self, room_alias: RoomAlias
-    ) -> Optional[RoomAliasMapping]:
+    ) -> RoomAliasMapping | None:
         result = await self.store.get_association_from_room_alias(room_alias)
         if not result:
             # Query AS to see if it exists
@@ -395,7 +395,7 @@ class DirectoryHandler:
             result = await as_handler.query_room_alias_exists(room_alias)
         return result
 
-    def can_modify_alias(self, alias: RoomAlias, user_id: Optional[str] = None) -> bool:
+    def can_modify_alias(self, alias: RoomAlias, user_id: str | None = None) -> bool:
         # Any application service "interested" in an alias they are regexing on
         # can modify the alias.
         # Users can only modify the alias if ALL the interested services have
diff --git a/synapse/handlers/e2e_keys.py b/synapse/handlers/e2e_keys.py
index 2774417c0b..41d27d47da 100644
--- a/synapse/handlers/e2e_keys.py
+++ b/synapse/handlers/e2e_keys.py
@@ -20,7 +20,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, Dict, Iterable, List, Mapping, Optional, Tuple
+from typing import TYPE_CHECKING, Iterable, Mapping
 
 import attr
 from canonicaljson import encode_canonical_json
@@ -57,7 +57,6 @@ if TYPE_CHECKING:
 
 logger = logging.getLogger(__name__)
 
-
 ONE_TIME_KEY_UPLOAD = "one_time_key_upload_lock"
 
 
@@ -133,7 +132,7 @@ class E2eKeysHandler:
         query_body: JsonDict,
         timeout: int,
         from_user_id: str,
-        from_device_id: Optional[str],
+        from_device_id: str | None,
     ) -> JsonDict:
         """Handle a device key query from a client
 
@@ -163,8 +162,8 @@ class E2eKeysHandler:
         async with self._query_devices_linearizer.queue((from_user_id, from_device_id)):
 
             async def filter_device_key_query(
-                query: Dict[str, List[str]],
-            ) -> Dict[str, List[str]]:
+                query: dict[str, list[str]],
+            ) -> dict[str, list[str]]:
                 if not self.config.experimental.msc4263_limit_key_queries_to_users_who_share_rooms:
                     # Only ignore invalid user IDs, which is the same behaviour as if
                     # the user existed but had no keys.
@@ -189,7 +188,7 @@ class E2eKeysHandler:
                     if user_id in allowed_user_ids
                 }
 
-            device_keys_query: Dict[str, List[str]] = await filter_device_key_query(
+            device_keys_query: dict[str, list[str]] = await filter_device_key_query(
                 query_body.get("device_keys", {})
             )
 
@@ -210,7 +209,7 @@ class E2eKeysHandler:
 
             # First get local devices.
             # A map of destination -> failure response.
-            failures: Dict[str, JsonDict] = {}
+            failures: dict[str, JsonDict] = {}
             results = {}
             if local_query:
                 local_result = await self.query_local_devices(local_query)
@@ -225,10 +224,10 @@ class E2eKeysHandler:
 
             # Now attempt to get any remote devices from our local cache.
             # A map of destination -> user ID -> device IDs.
-            remote_queries_not_in_cache: Dict[str, Dict[str, Iterable[str]]] = {}
+            remote_queries_not_in_cache: dict[str, dict[str, Iterable[str]]] = {}
             if remote_queries:
                 user_ids = set()
-                user_and_device_ids: List[Tuple[str, str]] = []
+                user_and_device_ids: list[tuple[str, str]] = []
                 for user_id, device_ids in remote_queries.items():
                     if device_ids:
                         user_and_device_ids.extend(
@@ -356,9 +355,9 @@ class E2eKeysHandler:
         self,
         results: JsonDict,
         cross_signing_keys: JsonDict,
-        failures: Dict[str, JsonDict],
+        failures: dict[str, JsonDict],
         destination: str,
-        destination_query: Dict[str, Iterable[str]],
+        destination_query: dict[str, Iterable[str]],
         timeout: int,
     ) -> None:
         """This is called when we are querying the device list of a user on
@@ -480,8 +479,8 @@ class E2eKeysHandler:
 
     @cancellable
     async def get_cross_signing_keys_from_cache(
-        self, query: Iterable[str], from_user_id: Optional[str]
-    ) -> Dict[str, Dict[str, JsonMapping]]:
+        self, query: Iterable[str], from_user_id: str | None
+    ) -> dict[str, dict[str, JsonMapping]]:
         """Get cross-signing keys for users from the database
 
         Args:
@@ -528,9 +527,9 @@ class E2eKeysHandler:
     @cancellable
     async def query_local_devices(
         self,
-        query: Mapping[str, Optional[List[str]]],
+        query: Mapping[str, list[str] | None],
         include_displaynames: bool = True,
-    ) -> Dict[str, Dict[str, dict]]:
+    ) -> dict[str, dict[str, dict]]:
         """Get E2E device keys for local users
 
         Args:
@@ -543,9 +542,9 @@ class E2eKeysHandler:
             A map from user_id -> device_id -> device details
         """
         set_tag("local_query", str(query))
-        local_query: List[Tuple[str, Optional[str]]] = []
+        local_query: list[tuple[str, str | None]] = []
 
-        result_dict: Dict[str, Dict[str, dict]] = {}
+        result_dict: dict[str, dict[str, dict]] = {}
         for user_id, device_ids in query.items():
             # we use UserID.from_string to catch invalid user ids
             if not self.is_mine(UserID.from_string(user_id)):
@@ -595,7 +594,7 @@ class E2eKeysHandler:
         return result_dict
 
     async def on_federation_query_client_keys(
-        self, query_body: Dict[str, Dict[str, Optional[List[str]]]]
+        self, query_body: dict[str, dict[str, list[str] | None]]
     ) -> JsonDict:
         """Handle a device key query from a federated server:
 
@@ -615,7 +614,7 @@ class E2eKeysHandler:
                 - self_signing_key: An optional dictionary of user ID -> self-signing
                     key info.
         """
-        device_keys_query: Dict[str, Optional[List[str]]] = query_body.get(
+        device_keys_query: dict[str, list[str] | None] = query_body.get(
             "device_keys", {}
         )
         if any(
@@ -640,9 +639,9 @@ class E2eKeysHandler:
 
     async def claim_local_one_time_keys(
         self,
-        local_query: List[Tuple[str, str, str, int]],
+        local_query: list[tuple[str, str, str, int]],
         always_include_fallback_keys: bool,
-    ) -> Iterable[Dict[str, Dict[str, Dict[str, JsonDict]]]]:
+    ) -> Iterable[dict[str, dict[str, dict[str, JsonDict]]]]:
         """Claim one time keys for local users.
 
         1. Attempt to claim OTKs from the database.
@@ -736,9 +735,9 @@ class E2eKeysHandler:
     @trace
     async def claim_one_time_keys(
         self,
-        query: Dict[str, Dict[str, Dict[str, int]]],
+        query: dict[str, dict[str, dict[str, int]]],
         user: UserID,
-        timeout: Optional[int],
+        timeout: int | None,
         always_include_fallback_keys: bool,
     ) -> JsonDict:
         """
@@ -755,8 +754,8 @@ class E2eKeysHandler:
             one_time_keys: chain of maps user ID -> device ID -> key ID -> key.
             failures: map from remote destination to a JsonDict describing the error.
         """
-        local_query: List[Tuple[str, str, str, int]] = []
-        remote_queries: Dict[str, Dict[str, Dict[str, Dict[str, int]]]] = {}
+        local_query: list[tuple[str, str, str, int]] = []
+        remote_queries: dict[str, dict[str, dict[str, dict[str, int]]]] = {}
 
         for user_id, one_time_keys in query.items():
             # we use UserID.from_string to catch invalid user ids
@@ -776,7 +775,7 @@ class E2eKeysHandler:
         )
 
         # A map of user ID -> device ID -> key ID -> key.
-        json_result: Dict[str, Dict[str, Dict[str, JsonDict]]] = {}
+        json_result: dict[str, dict[str, dict[str, JsonDict]]] = {}
         for result in results:
             for user_id, device_keys in result.items():
                 for device_id, keys in device_keys.items():
@@ -786,7 +785,7 @@ class E2eKeysHandler:
                         ).update({key_id: key})
 
         # Remote failures.
-        failures: Dict[str, JsonDict] = {}
+        failures: dict[str, JsonDict] = {}
 
         @trace
         async def claim_client_keys(destination: str) -> None:
@@ -847,14 +846,22 @@ class E2eKeysHandler:
         """
         time_now = self.clock.time_msec()
 
-        # TODO: Validate the JSON to make sure it has the right keys.
         device_keys = keys.get("device_keys", None)
         if device_keys:
+            log_kv(
+                {
+                    "message": "Updating device_keys for user.",
+                    "user_id": user_id,
+                    "device_id": device_id,
+                }
+            )
             await self.upload_device_keys_for_user(
                 user_id=user_id,
                 device_id=device_id,
                 keys={"device_keys": device_keys},
             )
+        else:
+            log_kv({"message": "Did not update device_keys", "reason": "not a dict"})
 
         one_time_keys = keys.get("one_time_keys", None)
         if one_time_keys:
@@ -872,10 +879,9 @@ class E2eKeysHandler:
             log_kv(
                 {"message": "Did not update one_time_keys", "reason": "no keys given"}
             )
-        fallback_keys = keys.get("fallback_keys") or keys.get(
-            "org.matrix.msc2732.fallback_keys"
-        )
-        if fallback_keys and isinstance(fallback_keys, dict):
+
+        fallback_keys = keys.get("fallback_keys")
+        if fallback_keys:
             log_kv(
                 {
                     "message": "Updating fallback_keys for device.",
@@ -884,8 +890,6 @@ class E2eKeysHandler:
                 }
             )
             await self.store.set_e2e_fallback_keys(user_id, device_id, fallback_keys)
-        elif fallback_keys:
-            log_kv({"message": "Did not update fallback_keys", "reason": "not a dict"})
         else:
             log_kv(
                 {"message": "Did not update fallback_keys", "reason": "no keys given"}
@@ -1127,7 +1131,7 @@ class E2eKeysHandler:
 
     async def _process_self_signatures(
         self, user_id: str, signatures: JsonDict
-    ) -> Tuple[List["SignatureListItem"], Dict[str, Dict[str, dict]]]:
+    ) -> tuple[list["SignatureListItem"], dict[str, dict[str, dict]]]:
         """Process uploaded signatures of the user's own keys.
 
         Signatures of the user's own keys from this API come in two forms:
@@ -1145,8 +1149,8 @@ class E2eKeysHandler:
         Raises:
             SynapseError: if the input is malformed
         """
-        signature_list: List["SignatureListItem"] = []
-        failures: Dict[str, Dict[str, JsonDict]] = {}
+        signature_list: list["SignatureListItem"] = []
+        failures: dict[str, dict[str, JsonDict]] = {}
         if not signatures:
             return signature_list, failures
 
@@ -1246,8 +1250,8 @@ class E2eKeysHandler:
         master_key_id: str,
         signed_master_key: JsonDict,
         stored_master_key: JsonMapping,
-        devices: Dict[str, Dict[str, JsonDict]],
-    ) -> List["SignatureListItem"]:
+        devices: dict[str, dict[str, JsonDict]],
+    ) -> list["SignatureListItem"]:
         """Check signatures of a user's master key made by their devices.
 
         Args:
@@ -1290,8 +1294,8 @@ class E2eKeysHandler:
         return master_key_signature_list
 
     async def _process_other_signatures(
-        self, user_id: str, signatures: Dict[str, dict]
-    ) -> Tuple[List["SignatureListItem"], Dict[str, Dict[str, dict]]]:
+        self, user_id: str, signatures: dict[str, dict]
+    ) -> tuple[list["SignatureListItem"], dict[str, dict[str, dict]]]:
         """Process uploaded signatures of other users' keys.  These will be the
         target user's master keys, signed by the uploading user's user-signing
         key.
@@ -1307,8 +1311,8 @@ class E2eKeysHandler:
         Raises:
             SynapseError: if the input is malformed
         """
-        signature_list: List["SignatureListItem"] = []
-        failures: Dict[str, Dict[str, JsonDict]] = {}
+        signature_list: list["SignatureListItem"] = []
+        failures: dict[str, dict[str, JsonDict]] = {}
         if not signatures:
             return signature_list, failures
 
@@ -1391,8 +1395,8 @@ class E2eKeysHandler:
         return signature_list, failures
 
     async def _get_e2e_cross_signing_verify_key(
-        self, user_id: str, key_type: str, from_user_id: Optional[str] = None
-    ) -> Tuple[JsonMapping, str, VerifyKey]:
+        self, user_id: str, key_type: str, from_user_id: str | None = None
+    ) -> tuple[JsonMapping, str, VerifyKey]:
         """Fetch locally or remotely query for a cross-signing public key.
 
         First, attempt to fetch the cross-signing public key from storage.
@@ -1447,7 +1451,7 @@ class E2eKeysHandler:
         self,
         user: UserID,
         desired_key_type: str,
-    ) -> Optional[Tuple[JsonMapping, str, VerifyKey]]:
+    ) -> tuple[JsonMapping, str, VerifyKey] | None:
         """Queries cross-signing keys for a remote user and saves them to the database
 
         Only the key specified by `key_type` will be returned, while all retrieved keys
@@ -1537,7 +1541,7 @@ class E2eKeysHandler:
 
         return desired_key_data
 
-    async def check_cross_signing_setup(self, user_id: str) -> Tuple[bool, bool]:
+    async def check_cross_signing_setup(self, user_id: str) -> tuple[bool, bool]:
         """Checks if the user has cross-signing set up
 
         Args:
@@ -1595,7 +1599,7 @@ class E2eKeysHandler:
 
     async def _delete_old_one_time_keys_task(
         self, task: ScheduledTask
-    ) -> Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]:
+    ) -> tuple[TaskStatus, JsonMapping | None, str | None]:
         """Scheduler task to delete old one time keys.
 
         Until Synapse 1.119, Synapse used to issue one-time-keys in a random order, leading to the possibility
@@ -1634,7 +1638,7 @@ class E2eKeysHandler:
 
 
 def _check_cross_signing_key(
-    key: JsonDict, user_id: str, key_type: str, signing_key: Optional[VerifyKey] = None
+    key: JsonDict, user_id: str, key_type: str, signing_key: VerifyKey | None = None
 ) -> None:
     """Check a cross-signing key uploaded by a user.  Performs some basic sanity
     checking, and ensures that it is signed, if a signature is required.
@@ -1769,7 +1773,7 @@ class SigningKeyEduUpdater:
         )
 
         # user_id -> list of updates waiting to be handled.
-        self._pending_updates: Dict[str, List[Tuple[JsonDict, JsonDict]]] = {}
+        self._pending_updates: dict[str, list[tuple[JsonDict, JsonDict]]] = {}
 
     async def incoming_signing_key_update(
         self, origin: str, edu_content: JsonDict
@@ -1815,7 +1819,7 @@ class SigningKeyEduUpdater:
                 # This can happen since we batch updates
                 return
 
-            device_ids: List[str] = []
+            device_ids: list[str] = []
 
             logger.info("pending updates: %r", pending_updates)
 
diff --git a/synapse/handlers/e2e_room_keys.py b/synapse/handlers/e2e_room_keys.py
index 623fd33f13..017fbcf8b3 100644
--- a/synapse/handlers/e2e_room_keys.py
+++ b/synapse/handlers/e2e_room_keys.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Dict, Literal, Optional, cast
+from typing import TYPE_CHECKING, Literal, cast
 
 from synapse.api.errors import (
     Codes,
@@ -63,10 +63,10 @@ class E2eRoomKeysHandler:
         self,
         user_id: str,
         version: str,
-        room_id: Optional[str] = None,
-        session_id: Optional[str] = None,
-    ) -> Dict[
-        Literal["rooms"], Dict[str, Dict[Literal["sessions"], Dict[str, RoomKey]]]
+        room_id: str | None = None,
+        session_id: str | None = None,
+    ) -> dict[
+        Literal["rooms"], dict[str, dict[Literal["sessions"], dict[str, RoomKey]]]
     ]:
         """Bulk get the E2E room keys for a given backup, optionally filtered to a given
         room, or a given session.
@@ -109,8 +109,8 @@ class E2eRoomKeysHandler:
         self,
         user_id: str,
         version: str,
-        room_id: Optional[str] = None,
-        session_id: Optional[str] = None,
+        room_id: str | None = None,
+        session_id: str | None = None,
     ) -> JsonDict:
         """Bulk delete the E2E room keys for a given backup, optionally filtered to a given
         room or a given session.
@@ -299,7 +299,7 @@ class E2eRoomKeysHandler:
 
     @staticmethod
     def _should_replace_room_key(
-        current_room_key: Optional[RoomKey], room_key: RoomKey
+        current_room_key: RoomKey | None, room_key: RoomKey
     ) -> bool:
         """
         Determine whether to replace a given current_room_key (if any)
@@ -360,7 +360,7 @@ class E2eRoomKeysHandler:
             return new_version
 
     async def get_version_info(
-        self, user_id: str, version: Optional[str] = None
+        self, user_id: str, version: str | None = None
     ) -> JsonDict:
         """Get the info about a given version of the user's backup
 
@@ -394,7 +394,7 @@ class E2eRoomKeysHandler:
             return res
 
     @trace
-    async def delete_version(self, user_id: str, version: Optional[str] = None) -> None:
+    async def delete_version(self, user_id: str, version: str | None = None) -> None:
         """Deletes a given version of the user's e2e_room_keys backup
 
         Args:
diff --git a/synapse/handlers/event_auth.py b/synapse/handlers/event_auth.py
index 1f1f67dc0d..4f2657bba8 100644
--- a/synapse/handlers/event_auth.py
+++ b/synapse/handlers/event_auth.py
@@ -19,7 +19,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, List, Mapping, Optional, Union
+from typing import TYPE_CHECKING, Mapping
 
 from synapse import event_auth
 from synapse.api.constants import (
@@ -61,7 +61,7 @@ class EventAuthHandler:
     async def check_auth_rules_from_context(
         self,
         event: EventBase,
-        batched_auth_events: Optional[Mapping[str, EventBase]] = None,
+        batched_auth_events: Mapping[str, EventBase] | None = None,
     ) -> None:
         """Check an event passes the auth rules at its own auth events
         Args:
@@ -89,10 +89,10 @@ class EventAuthHandler:
 
     def compute_auth_events(
         self,
-        event: Union[EventBase, EventBuilder],
+        event: EventBase | EventBuilder,
         current_state_ids: StateMap[str],
         for_verification: bool = False,
-    ) -> List[str]:
+    ) -> list[str]:
         """Given an event and current state return the list of event IDs used
         to auth an event.
 
@@ -236,7 +236,7 @@ class EventAuthHandler:
         state_ids: StateMap[str],
         room_version: RoomVersion,
         user_id: str,
-        prev_membership: Optional[str],
+        prev_membership: str | None,
     ) -> None:
         """
         Check whether a user can join a room without an invite due to restricted join rules.
diff --git a/synapse/handlers/events.py b/synapse/handlers/events.py
index 3f46032a43..ae17639206 100644
--- a/synapse/handlers/events.py
+++ b/synapse/handlers/events.py
@@ -21,7 +21,7 @@
 
 import logging
 import random
-from typing import TYPE_CHECKING, Iterable, List, Optional
+from typing import TYPE_CHECKING, Iterable
 
 from synapse.api.constants import EduTypes, EventTypes, Membership, PresenceState
 from synapse.api.errors import AuthError, SynapseError
@@ -58,7 +58,7 @@ class EventStreamHandler:
         timeout: int = 0,
         as_client_event: bool = True,
         affect_presence: bool = True,
-        room_id: Optional[str] = None,
+        room_id: str | None = None,
     ) -> JsonDict:
         """Fetches the events stream for a given user."""
 
@@ -100,7 +100,7 @@ class EventStreamHandler:
 
             # When the user joins a new room, or another user joins a currently
             # joined room, we need to send down presence for those users.
-            to_add: List[JsonDict] = []
+            to_add: list[JsonDict] = []
             for event in events:
                 if not isinstance(event, EventBase):
                     continue
@@ -152,10 +152,10 @@ class EventHandler:
     async def get_event(
         self,
         user: UserID,
-        room_id: Optional[str],
+        room_id: str | None,
         event_id: str,
         show_redacted: bool = False,
-    ) -> Optional[EventBase]:
+    ) -> EventBase | None:
         """Retrieve a single specified event.
 
         Args:
diff --git a/synapse/handlers/federation.py b/synapse/handlers/federation.py
index 41fb3076c3..1bba3fc758 100644
--- a/synapse/handlers/federation.py
+++ b/synapse/handlers/federation.py
@@ -30,13 +30,7 @@ from http import HTTPStatus
 from typing import (
     TYPE_CHECKING,
     AbstractSet,
-    Dict,
     Iterable,
-    List,
-    Optional,
-    Set,
-    Tuple,
-    Union,
 )
 
 import attr
@@ -72,7 +66,6 @@ from synapse.http.servlet import assert_params_in_dict
 from synapse.logging.context import nested_logging_context
 from synapse.logging.opentracing import SynapseTags, set_tag, tag_args, trace
 from synapse.metrics import SERVER_NAME_LABEL
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.module_api import NOT_SPAM
 from synapse.storage.databases.main.events_worker import EventRedactBehaviour
 from synapse.storage.invite_rule import InviteRule
@@ -169,12 +162,12 @@ class FederationHandler:
         # Tracks running partial state syncs by room ID.
         # Partial state syncs currently only run on the main process, so it's okay to
         # track them in-memory for now.
-        self._active_partial_state_syncs: Set[str] = set()
+        self._active_partial_state_syncs: set[str] = set()
         # Tracks partial state syncs we may want to restart.
         # A dictionary mapping room IDs to (initial destination, other destinations)
         # tuples.
-        self._partial_state_syncs_maybe_needing_restart: Dict[
-            str, Tuple[Optional[str], AbstractSet[str]]
+        self._partial_state_syncs_maybe_needing_restart: dict[
+            str, tuple[str | None, AbstractSet[str]]
         ] = {}
         # A lock guarding the partial state flag for rooms.
         # When the lock is held for a given room, no other concurrent code may
@@ -188,9 +181,8 @@ class FederationHandler:
         # any partial-state-resync operations which were in flight when we
         # were shut down.
         if not hs.config.worker.worker_app:
-            run_as_background_process(
+            self.hs.run_as_background_process(
                 "resume_sync_partial_state_room",
-                self.server_name,
                 self._resume_partial_state_room_sync,
             )
 
@@ -238,7 +230,7 @@ class FederationHandler:
         current_depth: int,
         limit: int,
         *,
-        processing_start_time: Optional[int],
+        processing_start_time: int | None,
     ) -> bool:
         """
         Checks whether the `current_depth` is at or approaching any backfill
@@ -274,7 +266,7 @@ class FederationHandler:
 
         # we now have a list of potential places to backpaginate from. We prefer to
         # start with the most recent (ie, max depth), so let's sort the list.
-        sorted_backfill_points: List[_BackfillPoint] = sorted(
+        sorted_backfill_points: list[_BackfillPoint] = sorted(
             backwards_extremities,
             key=lambda e: -int(e.depth),
         )
@@ -318,9 +310,8 @@ class FederationHandler:
             logger.debug(
                 "_maybe_backfill_inner: all backfill points are *after* current depth. Trying again with later backfill points."
             )
-            run_as_background_process(
+            self.hs.run_as_background_process(
                 "_maybe_backfill_inner_anyway_with_max_depth",
-                self.server_name,
                 self.maybe_backfill,
                 room_id=room_id,
                 # We use `MAX_DEPTH` so that we find all backfill points next
@@ -383,7 +374,7 @@ class FederationHandler:
         # there is it's often sufficiently long ago that clients would stop
         # attempting to paginate before backfill reached the visible history.
 
-        extremities_to_request: List[str] = []
+        extremities_to_request: list[str] = []
         for bp in sorted_backfill_points:
             if len(extremities_to_request) >= 5:
                 break
@@ -565,7 +556,7 @@ class FederationHandler:
 
         return pdu
 
-    async def on_event_auth(self, event_id: str) -> List[EventBase]:
+    async def on_event_auth(self, event_id: str) -> list[EventBase]:
         event = await self.store.get_event(event_id)
         auth = await self.store.get_auth_chain(
             event.room_id, list(event.auth_event_ids()), include_given=True
@@ -574,7 +565,7 @@ class FederationHandler:
 
     async def do_invite_join(
         self, target_hosts: Iterable[str], room_id: str, joinee: str, content: JsonDict
-    ) -> Tuple[str, int]:
+    ) -> tuple[str, int]:
         """Attempts to join the `joinee` to the room `room_id` via the
         servers contained in `target_hosts`.
 
@@ -802,20 +793,19 @@ class FederationHandler:
             # lots of requests for missing prev_events which we do actually
             # have. Hence we fire off the background task, but don't wait for it.
 
-            run_as_background_process(
+            self.hs.run_as_background_process(
                 "handle_queued_pdus",
-                self.server_name,
                 self._handle_queued_pdus,
                 room_queue,
             )
 
     async def do_knock(
         self,
-        target_hosts: List[str],
+        target_hosts: list[str],
         room_id: str,
         knockee: str,
         content: JsonDict,
-    ) -> Tuple[str, int]:
+    ) -> tuple[str, int]:
         """Sends the knock to the remote server.
 
         This first triggers a make_knock request that returns a partial
@@ -844,7 +834,7 @@ class FederationHandler:
 
         # Ask the remote server to create a valid knock event for us. Once received,
         # we sign the event
-        params: Dict[str, Iterable[str]] = {"ver": supported_room_versions}
+        params: dict[str, Iterable[str]] = {"ver": supported_room_versions}
         origin, event, event_format_version = await self._make_and_verify_event(
             target_hosts, room_id, knockee, Membership.KNOCK, content, params=params
         )
@@ -893,7 +883,7 @@ class FederationHandler:
         return event.event_id, stream_id
 
     async def _handle_queued_pdus(
-        self, room_queue: List[Tuple[EventBase, str]]
+        self, room_queue: list[tuple[EventBase, str]]
     ) -> None:
         """Process PDUs which got queued up while we were busy send_joining.
 
@@ -1148,7 +1138,7 @@ class FederationHandler:
 
     async def do_remotely_reject_invite(
         self, target_hosts: Iterable[str], room_id: str, user_id: str, content: JsonDict
-    ) -> Tuple[EventBase, int]:
+    ) -> tuple[EventBase, int]:
         origin, event, room_version = await self._make_and_verify_event(
             target_hosts, room_id, user_id, "leave", content=content
         )
@@ -1182,8 +1172,8 @@ class FederationHandler:
         user_id: str,
         membership: str,
         content: JsonDict,
-        params: Optional[Dict[str, Union[str, Iterable[str]]]] = None,
-    ) -> Tuple[str, EventBase, RoomVersion]:
+        params: dict[str, str | Iterable[str]] | None = None,
+    ) -> tuple[str, EventBase, RoomVersion]:
         (
             origin,
             event,
@@ -1310,7 +1300,7 @@ class FederationHandler:
 
     @trace
     @tag_args
-    async def get_state_ids_for_pdu(self, room_id: str, event_id: str) -> List[str]:
+    async def get_state_ids_for_pdu(self, room_id: str, event_id: str) -> list[str]:
         """Returns the state at the event. i.e. not including said event."""
         event = await self.store.get_event(event_id, check_room_id=room_id)
         if event.internal_metadata.outlier:
@@ -1343,8 +1333,8 @@ class FederationHandler:
         return list(state_map.values())
 
     async def on_backfill_request(
-        self, origin: str, room_id: str, pdu_list: List[str], limit: int
-    ) -> List[EventBase]:
+        self, origin: str, room_id: str, pdu_list: list[str], limit: int
+    ) -> list[EventBase]:
         # We allow partially joined rooms since in this case we are filtering out
         # non-local events in `filter_events_for_server`.
         await self._event_auth_handler.assert_host_in_room(room_id, origin, True)
@@ -1379,9 +1369,7 @@ class FederationHandler:
 
         return events
 
-    async def get_persisted_pdu(
-        self, origin: str, event_id: str
-    ) -> Optional[EventBase]:
+    async def get_persisted_pdu(self, origin: str, event_id: str) -> EventBase | None:
         """Get an event from the database for the given server.
 
         Args:
@@ -1420,10 +1408,10 @@ class FederationHandler:
         self,
         origin: str,
         room_id: str,
-        earliest_events: List[str],
-        latest_events: List[str],
+        earliest_events: list[str],
+        latest_events: list[str],
         limit: int,
-    ) -> List[EventBase]:
+    ) -> list[EventBase]:
         # We allow partially joined rooms since in this case we are filtering out
         # non-local events in `filter_events_for_server`.
         await self._event_auth_handler.assert_host_in_room(room_id, origin, True)
@@ -1606,7 +1594,7 @@ class FederationHandler:
         event_dict: JsonDict,
         event: EventBase,
         context: UnpersistedEventContextBase,
-    ) -> Tuple[EventBase, UnpersistedEventContextBase]:
+    ) -> tuple[EventBase, UnpersistedEventContextBase]:
         key = (
             EventTypes.ThirdPartyInvite,
             event.content["third_party_invite"]["signed"]["token"],
@@ -1678,7 +1666,7 @@ class FederationHandler:
 
         logger.debug("Checking auth on event %r", event.content)
 
-        last_exception: Optional[Exception] = None
+        last_exception: Exception | None = None
 
         # for each public key in the 3pid invite event
         for public_key_object in event_auth.get_public_keys(invite_event):
@@ -1762,8 +1750,8 @@ class FederationHandler:
             raise AuthError(403, "Third party certificate was invalid")
 
     async def get_room_complexity(
-        self, remote_room_hosts: List[str], room_id: str
-    ) -> Optional[dict]:
+        self, remote_room_hosts: list[str], room_id: str
+    ) -> dict | None:
         """
         Fetch the complexity of a remote room over federation.
 
@@ -1801,7 +1789,7 @@ class FederationHandler:
 
     def _start_partial_state_room_sync(
         self,
-        initial_destination: Optional[str],
+        initial_destination: str | None,
         other_destinations: AbstractSet[str],
         room_id: str,
     ) -> None:
@@ -1877,15 +1865,14 @@ class FederationHandler:
                             room_id=room_id,
                         )
 
-        run_as_background_process(
+        self.hs.run_as_background_process(
             desc="sync_partial_state_room",
-            server_name=self.server_name,
             func=_sync_partial_state_room_wrapper,
         )
 
     async def _sync_partial_state_room(
         self,
-        initial_destination: Optional[str],
+        initial_destination: str | None,
         other_destinations: AbstractSet[str],
         room_id: str,
     ) -> None:
@@ -2027,7 +2014,7 @@ class FederationHandler:
 
 
 def _prioritise_destinations_for_partial_state_resync(
-    initial_destination: Optional[str],
+    initial_destination: str | None,
     other_destinations: AbstractSet[str],
     room_id: str,
 ) -> StrCollection:
diff --git a/synapse/handlers/federation_event.py b/synapse/handlers/federation_event.py
index 59886f04c4..01e98f60ad 100644
--- a/synapse/handlers/federation_event.py
+++ b/synapse/handlers/federation_event.py
@@ -27,13 +27,8 @@ from typing import (
     TYPE_CHECKING,
     Collection,
     Container,
-    Dict,
     Iterable,
-    List,
-    Optional,
     Sequence,
-    Set,
-    Tuple,
 )
 
 from prometheus_client import Counter, Histogram
@@ -81,7 +76,6 @@ from synapse.logging.opentracing import (
     trace,
 )
 from synapse.metrics import SERVER_NAME_LABEL
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.replication.http.federation import (
     ReplicationFederationSendEventsRestServlet,
 )
@@ -153,6 +147,7 @@ class FederationEventHandler:
 
     def __init__(self, hs: "HomeServer"):
         self.server_name = hs.hostname
+        self.hs = hs
         self._clock = hs.get_clock()
         self._store = hs.get_datastores().main
         self._state_store = hs.get_datastores().state
@@ -175,6 +170,7 @@ class FederationEventHandler:
         )
         self._notifier = hs.get_notifier()
 
+        self._server_name = hs.hostname
         self._is_mine_id = hs.is_mine_id
         self._is_mine_server_name = hs.is_mine_server_name
         self._instance_name = hs.get_instance_name()
@@ -189,7 +185,7 @@ class FederationEventHandler:
         # For each room, a list of (pdu, origin) tuples.
         # TODO: replace this with something more elegant, probably based around the
         # federation event staging area.
-        self.room_queues: Dict[str, List[Tuple[EventBase, str]]] = {}
+        self.room_queues: dict[str, list[tuple[EventBase, str]]] = {}
 
         self._room_pdu_linearizer = Linearizer(name="fed_room_pdu", clock=self._clock)
 
@@ -510,8 +506,8 @@ class FederationEventHandler:
         self,
         origin: str,
         room_id: str,
-        auth_events: List[EventBase],
-        state: List[EventBase],
+        auth_events: list[EventBase],
+        state: list[EventBase],
         event: EventBase,
         room_version: RoomVersion,
         partial_state: bool,
@@ -594,7 +590,7 @@ class FederationEventHandler:
                 )
                 missing_event_ids = prev_event_ids - seen_event_ids
 
-                state_maps_to_resolve: List[StateMap[str]] = []
+                state_maps_to_resolve: list[StateMap[str]] = []
 
                 # Fetch the state after the prev events that we know about.
                 state_maps_to_resolve.extend(
@@ -754,7 +750,7 @@ class FederationEventHandler:
 
     @trace
     async def _get_missing_events_for_pdu(
-        self, origin: str, pdu: EventBase, prevs: Set[str], min_depth: int
+        self, origin: str, pdu: EventBase, prevs: set[str], min_depth: int
     ) -> None:
         """
         Args:
@@ -901,7 +897,7 @@ class FederationEventHandler:
             [event.event_id for event in events]
         )
 
-        new_events: List[EventBase] = []
+        new_events: list[EventBase] = []
         for event in events:
             event_id = event.event_id
 
@@ -974,9 +970,8 @@ class FederationEventHandler:
         # Process previously failed backfill events in the background to not waste
         # time on something that is likely to fail again.
         if len(events_with_failed_pull_attempts) > 0:
-            run_as_background_process(
+            self.hs.run_as_background_process(
                 "_process_new_pulled_events_with_failed_pull_attempts",
-                self.server_name,
                 _process_new_pulled_events,
                 events_with_failed_pull_attempts,
             )
@@ -1186,7 +1181,7 @@ class FederationEventHandler:
             partial_state = any(partial_state_flags.values())
 
             # state_maps is a list of mappings from (type, state_key) to event_id
-            state_maps: List[StateMap[str]] = []
+            state_maps: list[StateMap[str]] = []
 
             # Ask the remote server for the states we don't
             # know about
@@ -1568,9 +1563,8 @@ class FederationEventHandler:
                     resync = True
 
             if resync:
-                run_as_background_process(
+                self.hs.run_as_background_process(
                     "resync_device_due_to_pdu",
-                    self.server_name,
                     self._resync_device,
                     event.sender,
                 )
@@ -1648,7 +1642,7 @@ class FederationEventHandler:
 
         room_version = await self._store.get_room_version(room_id)
 
-        events: List[EventBase] = []
+        events: list[EventBase] = []
 
         async def get_event(event_id: str) -> None:
             with nested_logging_context(event_id):
@@ -1754,7 +1748,7 @@ class FederationEventHandler:
             )
             auth_map.update(persisted_events)
 
-        events_and_contexts_to_persist: List[EventPersistencePair] = []
+        events_and_contexts_to_persist: list[EventPersistencePair] = []
 
         async def prep(event: EventBase) -> None:
             with nested_logging_context(suffix=event.event_id):
@@ -1823,7 +1817,7 @@ class FederationEventHandler:
 
     @trace
     async def _check_event_auth(
-        self, origin: Optional[str], event: EventBase, context: EventContext
+        self, origin: str | None, event: EventBase, context: EventContext
     ) -> None:
         """
         Checks whether an event should be rejected (for failing auth checks).
@@ -2051,7 +2045,7 @@ class FederationEventHandler:
             state_sets_d = await self._state_storage_controller.get_state_groups_ids(
                 event.room_id, extrem_ids
             )
-            state_sets: List[StateMap[str]] = list(state_sets_d.values())
+            state_sets: list[StateMap[str]] = list(state_sets_d.values())
             state_ids = await context.get_prev_state_ids()
             state_sets.append(state_ids)
             current_state_ids = (
@@ -2106,7 +2100,7 @@ class FederationEventHandler:
             event.internal_metadata.soft_failed = True
 
     async def _load_or_fetch_auth_events_for_event(
-        self, destination: Optional[str], event: EventBase
+        self, destination: str | None, event: EventBase
     ) -> Collection[EventBase]:
         """Fetch this event's auth_events, from database or remote
 
diff --git a/synapse/handlers/identity.py b/synapse/handlers/identity.py
index be757201fc..1596c55570 100644
--- a/synapse/handlers/identity.py
+++ b/synapse/handlers/identity.py
@@ -24,7 +24,7 @@
 
 import logging
 import urllib.parse
-from typing import TYPE_CHECKING, Awaitable, Callable, Dict, List, Optional, Tuple
+from typing import TYPE_CHECKING, Awaitable, Callable
 
 import attr
 
@@ -105,8 +105,8 @@ class IdentityHandler:
         )
 
     async def threepid_from_creds(
-        self, id_server: str, creds: Dict[str, str]
-    ) -> Optional[JsonDict]:
+        self, id_server: str, creds: dict[str, str]
+    ) -> JsonDict | None:
         """
         Retrieve and validate a threepid identifier from a "credentials" dictionary against a
         given identity server
@@ -227,7 +227,7 @@ class IdentityHandler:
             return data
 
     async def try_unbind_threepid(
-        self, mxid: str, medium: str, address: str, id_server: Optional[str]
+        self, mxid: str, medium: str, address: str, id_server: str | None
     ) -> bool:
         """Attempt to remove a 3PID from one or more identity servers.
 
@@ -338,7 +338,7 @@ class IdentityHandler:
         client_secret: str,
         send_attempt: int,
         send_email_func: Callable[[str, str, str, str], Awaitable],
-        next_link: Optional[str] = None,
+        next_link: str | None = None,
     ) -> str:
         """Send a threepid validation email for password reset or
         registration purposes
@@ -426,7 +426,7 @@ class IdentityHandler:
         phone_number: str,
         client_secret: str,
         send_attempt: int,
-        next_link: Optional[str] = None,
+        next_link: str | None = None,
     ) -> JsonDict:
         """
         Request an external server send an SMS message on our behalf for the purposes of
@@ -473,7 +473,7 @@ class IdentityHandler:
 
     async def validate_threepid_session(
         self, client_secret: str, sid: str
-    ) -> Optional[JsonDict]:
+    ) -> JsonDict | None:
         """Validates a threepid session with only the client secret and session ID
         Tries validating against any configured account_threepid_delegates as well as locally.
 
@@ -541,7 +541,7 @@ class IdentityHandler:
 
     async def lookup_3pid(
         self, id_server: str, medium: str, address: str, id_access_token: str
-    ) -> Optional[str]:
+    ) -> str | None:
         """Looks up a 3pid in the passed identity server.
 
         Args:
@@ -567,7 +567,7 @@ class IdentityHandler:
 
     async def _lookup_3pid_v2(
         self, id_server: str, id_access_token: str, medium: str, address: str
-    ) -> Optional[str]:
+    ) -> str | None:
         """Looks up a 3pid in the passed identity server using v2 lookup.
 
         Args:
@@ -689,11 +689,11 @@ class IdentityHandler:
         room_avatar_url: str,
         room_join_rules: str,
         room_name: str,
-        room_type: Optional[str],
+        room_type: str | None,
         inviter_display_name: str,
         inviter_avatar_url: str,
         id_access_token: str,
-    ) -> Tuple[str, List[Dict[str, str]], Dict[str, str], str]:
+    ) -> tuple[str, list[dict[str, str]], dict[str, str], str]:
         """
         Asks an identity server for a third party invite.
 
@@ -779,7 +779,7 @@ class IdentityHandler:
         return token, public_keys, fallback_public_key, display_name
 
 
-def create_id_access_token_header(id_access_token: str) -> List[str]:
+def create_id_access_token_header(id_access_token: str) -> list[str]:
     """Create an Authorization header for passing to SimpleHttpClient as the header value
     of an HTTP request.
 
diff --git a/synapse/handlers/initial_sync.py b/synapse/handlers/initial_sync.py
index 75d64d2d50..611c4fa7b3 100644
--- a/synapse/handlers/initial_sync.py
+++ b/synapse/handlers/initial_sync.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, List, Optional, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.constants import (
     AccountDataTypes,
@@ -69,10 +69,10 @@ class InitialSyncHandler:
         self.clock = hs.get_clock()
         self.validator = EventValidator()
         self.snapshot_cache: ResponseCache[
-            Tuple[
+            tuple[
                 str,
-                Optional[StreamToken],
-                Optional[StreamToken],
+                StreamToken | None,
+                StreamToken | None,
                 Direction,
                 int,
                 bool,
@@ -451,7 +451,7 @@ class InitialSyncHandler:
 
         presence_handler = self.hs.get_presence_handler()
 
-        async def get_presence() -> List[JsonDict]:
+        async def get_presence() -> list[JsonDict]:
             # If presence is disabled, return an empty list
             if not self.hs.config.server.presence_enabled:
                 return []
@@ -468,7 +468,7 @@ class InitialSyncHandler:
                 for s in states
             ]
 
-        async def get_receipts() -> List[JsonMapping]:
+        async def get_receipts() -> list[JsonMapping]:
             receipts = await self.store.get_linearized_receipts_for_room(
                 room_id, to_key=now_token.receipt_key
             )
diff --git a/synapse/handlers/jwt.py b/synapse/handlers/jwt.py
index 400f3a59aa..67b2b7c31d 100644
--- a/synapse/handlers/jwt.py
+++ b/synapse/handlers/jwt.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import TYPE_CHECKING, Optional, Tuple
+from typing import TYPE_CHECKING
 
 from authlib.jose import JsonWebToken, JWTClaims
 from authlib.jose.errors import BadSignatureError, InvalidClaimError, JoseError
@@ -41,7 +41,7 @@ class JwtHandler:
         self.jwt_issuer = hs.config.jwt.jwt_issuer
         self.jwt_audiences = hs.config.jwt.jwt_audiences
 
-    def validate_login(self, login_submission: JsonDict) -> Tuple[str, Optional[str]]:
+    def validate_login(self, login_submission: JsonDict) -> tuple[str, str | None]:
         """
         Authenticates the user for the /login API
 
diff --git a/synapse/handlers/message.py b/synapse/handlers/message.py
index 4ff8b3704b..7679303a36 100644
--- a/synapse/handlers/message.py
+++ b/synapse/handlers/message.py
@@ -22,7 +22,7 @@
 import logging
 import random
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Any, Dict, List, Mapping, Optional, Sequence, Tuple
+from typing import TYPE_CHECKING, Any, Mapping, Sequence
 
 from canonicaljson import encode_canonical_json
 
@@ -67,7 +67,6 @@ from synapse.handlers.directory import DirectoryHandler
 from synapse.handlers.worker_lock import NEW_EVENT_DURING_PURGE_LOCK_NAME
 from synapse.logging import opentracing
 from synapse.logging.context import make_deferred_yieldable, run_in_background
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.replication.http.send_events import ReplicationSendEventsRestServlet
 from synapse.storage.databases.main.events_worker import EventRedactBehaviour
 from synapse.types import (
@@ -99,6 +98,7 @@ class MessageHandler:
 
     def __init__(self, hs: "HomeServer"):
         self.server_name = hs.hostname
+        self.hs = hs
         self.auth = hs.get_auth()
         self.clock = hs.get_clock()
         self.state = hs.get_state_handler()
@@ -110,11 +110,11 @@ class MessageHandler:
 
         # The scheduled call to self._expire_event. None if no call is currently
         # scheduled.
-        self._scheduled_expiry: Optional[IDelayedCall] = None
+        self._scheduled_expiry: IDelayedCall | None = None
 
         if not hs.config.worker.worker_app:
-            run_as_background_process(
-                "_schedule_next_expiry", self.server_name, self._schedule_next_expiry
+            self.hs.run_as_background_process(
+                "_schedule_next_expiry", self._schedule_next_expiry
             )
 
     async def get_room_data(
@@ -123,7 +123,7 @@ class MessageHandler:
         room_id: str,
         event_type: str,
         state_key: str,
-    ) -> Optional[EventBase]:
+    ) -> EventBase | None:
         """Get data from a room.
 
         Args:
@@ -178,9 +178,9 @@ class MessageHandler:
         self,
         requester: Requester,
         room_id: str,
-        state_filter: Optional[StateFilter] = None,
-        at_token: Optional[StreamToken] = None,
-    ) -> List[dict]:
+        state_filter: StateFilter | None = None,
+        at_token: StreamToken | None = None,
+    ) -> list[dict]:
         """Retrieve all state events for a given room. If the user is
         joined to the room then return the current state. If the user has
         left the room return the state events from when they left. If an explicit
@@ -444,9 +444,8 @@ class MessageHandler:
 
         self._scheduled_expiry = self.clock.call_later(
             delay,
-            run_as_background_process,
+            self.hs.run_as_background_process,
             "_expire_event",
-            self.server_name,
             self._expire_event,
             event_id,
         )
@@ -539,7 +538,7 @@ class EventCreationHandler:
         #
         # map from room id to time-of-last-attempt.
         #
-        self._rooms_to_exclude_from_dummy_event_insertion: Dict[str, int] = {}
+        self._rooms_to_exclude_from_dummy_event_insertion: dict[str, int] = {}
         # The number of forward extremeities before a dummy event is sent.
         self._dummy_events_threshold = hs.config.server.dummy_events_threshold
 
@@ -548,9 +547,8 @@ class EventCreationHandler:
             and self.config.server.cleanup_extremities_with_dummy_events
         ):
             self.clock.looping_call(
-                lambda: run_as_background_process(
+                lambda: self.hs.run_as_background_process(
                     "send_dummy_events_to_fill_extremities",
-                    self.server_name,
                     self._send_dummy_events_to_fill_extremities,
                 ),
                 5 * 60 * 1000,
@@ -565,11 +563,12 @@ class EventCreationHandler:
         # Stores the state groups we've recently added to the joined hosts
         # external cache. Note that the timeout must be significantly less than
         # the TTL on the external cache.
-        self._external_cache_joined_hosts_updates: Optional[ExpiringCache] = None
+        self._external_cache_joined_hosts_updates: ExpiringCache | None = None
         if self._external_cache.is_enabled():
             self._external_cache_joined_hosts_updates = ExpiringCache(
                 cache_name="_external_cache_joined_hosts_updates",
                 server_name=self.server_name,
+                hs=self.hs,
                 clock=self.clock,
                 expiry_ms=30 * 60 * 1000,
             )
@@ -578,17 +577,17 @@ class EventCreationHandler:
         self,
         requester: Requester,
         event_dict: dict,
-        txn_id: Optional[str] = None,
-        prev_event_ids: Optional[List[str]] = None,
-        auth_event_ids: Optional[List[str]] = None,
-        state_event_ids: Optional[List[str]] = None,
+        txn_id: str | None = None,
+        prev_event_ids: list[str] | None = None,
+        auth_event_ids: list[str] | None = None,
+        state_event_ids: list[str] | None = None,
         require_consent: bool = True,
         outlier: bool = False,
-        depth: Optional[int] = None,
-        state_map: Optional[StateMap[str]] = None,
+        depth: int | None = None,
+        state_map: StateMap[str] | None = None,
         for_batch: bool = False,
-        current_state_group: Optional[int] = None,
-    ) -> Tuple[EventBase, UnpersistedEventContextBase]:
+        current_state_group: int | None = None,
+    ) -> tuple[EventBase, UnpersistedEventContextBase]:
         """
         Given a dict from a client, create a new event. If bool for_batch is true, will
         create an event using the prev_event_ids, and will create an event context for
@@ -866,7 +865,7 @@ class EventCreationHandler:
 
     async def deduplicate_state_event(
         self, event: EventBase, context: EventContext
-    ) -> Optional[EventBase]:
+    ) -> EventBase | None:
         """
         Checks whether event is in the latest resolved state in context.
 
@@ -904,7 +903,7 @@ class EventCreationHandler:
         requester: Requester,
         txn_id: str,
         room_id: str,
-    ) -> Optional[str]:
+    ) -> str | None:
         """For the given transaction ID and room ID, check if there is a matching event ID.
 
         Args:
@@ -938,7 +937,7 @@ class EventCreationHandler:
         requester: Requester,
         txn_id: str,
         room_id: str,
-    ) -> Optional[EventBase]:
+    ) -> EventBase | None:
         """For the given transaction ID and room ID, check if there is a matching event.
         If so, fetch it and return it.
 
@@ -962,14 +961,14 @@ class EventCreationHandler:
         self,
         requester: Requester,
         event_dict: dict,
-        prev_event_ids: Optional[List[str]] = None,
-        state_event_ids: Optional[List[str]] = None,
+        prev_event_ids: list[str] | None = None,
+        state_event_ids: list[str] | None = None,
         ratelimit: bool = True,
-        txn_id: Optional[str] = None,
+        txn_id: str | None = None,
         ignore_shadow_ban: bool = False,
         outlier: bool = False,
-        depth: Optional[int] = None,
-    ) -> Tuple[EventBase, int]:
+        depth: int | None = None,
+    ) -> tuple[EventBase, int]:
         """
         Creates an event, then sends it.
 
@@ -1099,14 +1098,14 @@ class EventCreationHandler:
         self,
         requester: Requester,
         event_dict: dict,
-        prev_event_ids: Optional[List[str]] = None,
-        state_event_ids: Optional[List[str]] = None,
+        prev_event_ids: list[str] | None = None,
+        state_event_ids: list[str] | None = None,
         ratelimit: bool = True,
-        txn_id: Optional[str] = None,
+        txn_id: str | None = None,
         ignore_shadow_ban: bool = False,
         outlier: bool = False,
-        depth: Optional[int] = None,
-    ) -> Tuple[EventBase, int]:
+        depth: int | None = None,
+    ) -> tuple[EventBase, int]:
         room_id = event_dict["room_id"]
 
         # If we don't have any prev event IDs specified then we need to
@@ -1220,15 +1219,15 @@ class EventCreationHandler:
     async def create_new_client_event(
         self,
         builder: EventBuilder,
-        requester: Optional[Requester] = None,
-        prev_event_ids: Optional[List[str]] = None,
-        auth_event_ids: Optional[List[str]] = None,
-        state_event_ids: Optional[List[str]] = None,
-        depth: Optional[int] = None,
-        state_map: Optional[StateMap[str]] = None,
+        requester: Requester | None = None,
+        prev_event_ids: list[str] | None = None,
+        auth_event_ids: list[str] | None = None,
+        state_event_ids: list[str] | None = None,
+        depth: int | None = None,
+        state_map: StateMap[str] | None = None,
         for_batch: bool = False,
-        current_state_group: Optional[int] = None,
-    ) -> Tuple[EventBase, UnpersistedEventContextBase]:
+        current_state_group: int | None = None,
+    ) -> tuple[EventBase, UnpersistedEventContextBase]:
         """Create a new event for a local client. If bool for_batch is true, will
         create an event using the prev_event_ids, and will create an event context for
         the event using the parameters state_map and current_state_group, thus these parameters
@@ -1472,9 +1471,9 @@ class EventCreationHandler:
     async def handle_new_client_event(
         self,
         requester: Requester,
-        events_and_context: List[EventPersistencePair],
+        events_and_context: list[EventPersistencePair],
         ratelimit: bool = True,
-        extra_users: Optional[List[UserID]] = None,
+        extra_users: list[UserID] | None = None,
         ignore_shadow_ban: bool = False,
     ) -> EventBase:
         """Processes new events. Please note that if batch persisting events, an error in
@@ -1593,7 +1592,7 @@ class EventCreationHandler:
         self,
         requester: Requester,
         room_id: str,
-        prev_event_id: Optional[str],
+        prev_event_id: str | None,
         event_dicts: Sequence[JsonDict],
         ratelimit: bool = True,
         ignore_shadow_ban: bool = False,
@@ -1684,9 +1683,9 @@ class EventCreationHandler:
     async def _persist_events(
         self,
         requester: Requester,
-        events_and_context: List[EventPersistencePair],
+        events_and_context: list[EventPersistencePair],
         ratelimit: bool = True,
-        extra_users: Optional[List[UserID]] = None,
+        extra_users: list[UserID] | None = None,
     ) -> EventBase:
         """Actually persists new events. Should only be called by
         `handle_new_client_event`, and see its docstring for documentation of
@@ -1770,7 +1769,7 @@ class EventCreationHandler:
             raise
 
     async def cache_joined_hosts_for_events(
-        self, events_and_context: List[EventPersistencePair]
+        self, events_and_context: list[EventPersistencePair]
     ) -> None:
         """Precalculate the joined hosts at each of the given events, when using Redis, so that
         external federation senders don't have to recalculate it themselves.
@@ -1876,9 +1875,9 @@ class EventCreationHandler:
     async def persist_and_notify_client_events(
         self,
         requester: Requester,
-        events_and_context: List[EventPersistencePair],
+        events_and_context: list[EventPersistencePair],
         ratelimit: bool = True,
-        extra_users: Optional[List[UserID]] = None,
+        extra_users: list[UserID] | None = None,
     ) -> EventBase:
         """Called when we have fully built the events, have already
         calculated the push actions for the events, and checked auth.
@@ -2113,9 +2112,8 @@ class EventCreationHandler:
             if event.type == EventTypes.Message:
                 # We don't want to block sending messages on any presence code. This
                 # matters as sometimes presence code can take a while.
-                run_as_background_process(
+                self.hs.run_as_background_process(
                     "bump_presence_active_time",
-                    self.server_name,
                     self._bump_active_time,
                     requester.user,
                     requester.device_id,
@@ -2134,7 +2132,7 @@ class EventCreationHandler:
         return persisted_events[-1]
 
     async def is_admin_redaction(
-        self, event_type: str, sender: str, redacts: Optional[str]
+        self, event_type: str, sender: str, redacts: str | None
     ) -> bool:
         """Return whether the event is a redaction made by an admin, and thus
         should use a different ratelimiter.
@@ -2176,7 +2174,7 @@ class EventCreationHandler:
         logger.info("maybe_kick_guest_users %r", current_state)
         await self.hs.get_room_member_handler().kick_guest_users(current_state)
 
-    async def _bump_active_time(self, user: UserID, device_id: Optional[str]) -> None:
+    async def _bump_active_time(self, user: UserID, device_id: str | None) -> None:
         try:
             presence = self.hs.get_presence_handler()
             await presence.bump_presence_active_time(user, device_id)
@@ -2287,7 +2285,7 @@ class EventCreationHandler:
 
     async def _rebuild_event_after_third_party_rules(
         self, third_party_result: dict, original_event: EventBase
-    ) -> Tuple[EventBase, UnpersistedEventContextBase]:
+    ) -> tuple[EventBase, UnpersistedEventContextBase]:
         # the third_party_event_rules want to replace the event.
         # we do some basic checks, and then return the replacement event.
 
diff --git a/synapse/handlers/oidc.py b/synapse/handlers/oidc.py
index fc93c6b2a8..429a739380 100644
--- a/synapse/handlers/oidc.py
+++ b/synapse/handlers/oidc.py
@@ -26,14 +26,9 @@ import logging
 from typing import (
     TYPE_CHECKING,
     Any,
-    Dict,
     Generic,
-    List,
-    Optional,
-    Type,
     TypedDict,
     TypeVar,
-    Union,
 )
 from urllib.parse import urlencode, urlparse
 
@@ -96,7 +91,7 @@ logger = logging.getLogger(__name__)
 # Here we have the names of the cookies, and the options we use to set them.
 _SESSION_COOKIES = [
     (b"oidc_session", b"HttpOnly; Secure; SameSite=None"),
-    (b"oidc_session_no_samesite", b"HttpOnly"),
+    (b"oidc_session_no_samesite", b"HttpOnly; Secure"),
 ]
 
 
@@ -105,22 +100,22 @@ _SESSION_COOKIES = [
 class Token(TypedDict):
     access_token: str
     token_type: str
-    id_token: Optional[str]
-    refresh_token: Optional[str]
+    id_token: str | None
+    refresh_token: str | None
     expires_in: int
-    scope: Optional[str]
+    scope: str | None
 
 
 #: A JWK, as per RFC7517 sec 4. The type could be more precise than that, but
 #: there is no real point of doing this in our case.
-JWK = Dict[str, str]
+JWK = dict[str, str]
 
 C = TypeVar("C")
 
 
 #: A JWK Set, as per RFC7517 sec 5.
 class JWKS(TypedDict):
-    keys: List[JWK]
+    keys: list[JWK]
 
 
 class OidcHandler:
@@ -134,7 +129,7 @@ class OidcHandler:
         assert provider_confs
 
         self._macaroon_generator = hs.get_macaroon_generator()
-        self._providers: Dict[str, "OidcProvider"] = {
+        self._providers: dict[str, "OidcProvider"] = {
             p.idp_id: OidcProvider(hs, self._macaroon_generator, p)
             for p in provider_confs
         }
@@ -209,7 +204,7 @@ class OidcHandler:
         # are two.
 
         for cookie_name, _ in _SESSION_COOKIES:
-            session: Optional[bytes] = request.getCookie(cookie_name)
+            session: bytes | None = request.getCookie(cookie_name)
             if session is not None:
                 break
         else:
@@ -332,13 +327,13 @@ class OidcHandler:
 
             # At this point we properly checked both claims types
             issuer: str = iss
-            audience: List[str] = aud
+            audience: list[str] = aud
         except (TypeError, KeyError):
             raise SynapseError(400, "Invalid issuer/audience in logout_token")
 
         # Now that we know the audience and the issuer, we can figure out from
         # what provider it is coming from
-        oidc_provider: Optional[OidcProvider] = None
+        oidc_provider: OidcProvider | None = None
         for provider in self._providers.values():
             if provider.issuer == issuer and provider.client_id in audience:
                 oidc_provider = provider
@@ -354,7 +349,7 @@ class OidcHandler:
 class OidcError(Exception):
     """Used to catch errors when calling the token_endpoint"""
 
-    def __init__(self, error: str, error_description: Optional[str] = None):
+    def __init__(self, error: str, error_description: str | None = None):
         self.error = error
         self.error_description = error_description
 
@@ -401,7 +396,7 @@ class OidcProvider:
         self._scopes = provider.scopes
         self._user_profile_method = provider.user_profile_method
 
-        client_secret: Optional[Union[str, JwtClientSecret]] = None
+        client_secret: str | JwtClientSecret | None = None
         if provider.client_secret:
             client_secret = provider.client_secret
         elif provider.client_secret_jwt_key:
@@ -428,8 +423,10 @@ class OidcProvider:
         # from the IdP's jwks_uri, if required.
         self._jwks = RetryOnExceptionCachedCall(self._load_jwks)
 
+        # type-ignore: we will not be instantiating a subclass of the provider class,
+        # so the warning about directly accessing __init__ being unsound does not apply here
         user_mapping_provider_init_method = (
-            provider.user_mapping_provider_class.__init__
+            provider.user_mapping_provider_class.__init__  # type: ignore[misc]
         )
         if len(inspect.signature(user_mapping_provider_init_method).parameters) == 3:
             self._user_mapping_provider = provider.user_mapping_provider_class(
@@ -758,7 +755,7 @@ class OidcProvider:
         """
         metadata = await self.load_metadata()
         token_endpoint = metadata.get("token_endpoint")
-        raw_headers: Dict[str, str] = {
+        raw_headers: dict[str, str] = {
             "Content-Type": "application/x-www-form-urlencoded",
             "User-Agent": self._http_client.user_agent.decode("ascii"),
             "Accept": "application/json",
@@ -902,11 +899,11 @@ class OidcProvider:
 
     async def _verify_jwt(
         self,
-        alg_values: List[str],
+        alg_values: list[str],
         token: str,
-        claims_cls: Type[C],
-        claims_options: Optional[dict] = None,
-        claims_params: Optional[dict] = None,
+        claims_cls: type[C],
+        claims_options: dict | None = None,
+        claims_params: dict | None = None,
     ) -> C:
         """Decode and validate a JWT, re-fetching the JWKS as needed.
 
@@ -1006,8 +1003,8 @@ class OidcProvider:
     async def handle_redirect_request(
         self,
         request: SynapseRequest,
-        client_redirect_url: Optional[bytes],
-        ui_auth_session_id: Optional[str] = None,
+        client_redirect_url: bytes | None,
+        ui_auth_session_id: str | None = None,
     ) -> str:
         """Handle an incoming request to /login/sso/redirect
 
@@ -1236,7 +1233,7 @@ class OidcProvider:
         token: Token,
         request: SynapseRequest,
         client_redirect_url: str,
-        sid: Optional[str],
+        sid: str | None,
     ) -> None:
         """Given a UserInfo response, complete the login flow
 
@@ -1301,7 +1298,7 @@ class OidcProvider:
 
             return UserAttributes(**attributes)
 
-        async def grandfather_existing_users() -> Optional[str]:
+        async def grandfather_existing_users() -> str | None:
             if self._allow_existing_users:
                 # If allowing existing users we want to generate a single localpart
                 # and attempt to match it.
@@ -1445,8 +1442,8 @@ class OidcProvider:
         # If the `sub` claim was included in the logout token, we check that it matches
         # that it matches the right user. We can have cases where the `sub` claim is not
         # the ID saved in database, so we let admins disable this check in config.
-        sub: Optional[str] = claims.get("sub")
-        expected_user_id: Optional[str] = None
+        sub: str | None = claims.get("sub")
+        expected_user_id: str | None = None
         if sub is not None and not self._config.backchannel_logout_ignore_sub:
             expected_user_id = await self._store.get_user_by_external_id(
                 self.idp_id, sub
@@ -1474,7 +1471,7 @@ class LogoutToken(JWTClaims):  # type: ignore[misc]
 
     REGISTERED_CLAIMS = ["iss", "sub", "aud", "iat", "jti", "events", "sid"]
 
-    def validate(self, now: Optional[int] = None, leeway: int = 0) -> None:
+    def validate(self, now: int | None = None, leeway: int = 0) -> None:
         """Validate everything in claims payload."""
         super().validate(now, leeway)
         self.validate_sid()
@@ -1585,11 +1582,11 @@ class JwtClientSecret:
 
 
 class UserAttributeDict(TypedDict):
-    localpart: Optional[str]
+    localpart: str | None
     confirm_localpart: bool
-    display_name: Optional[str]
-    picture: Optional[str]  # may be omitted by older `OidcMappingProviders`
-    emails: List[str]
+    display_name: str | None
+    picture: str | None  # may be omitted by older `OidcMappingProviders`
+    emails: list[str]
 
 
 class OidcMappingProvider(Generic[C]):
@@ -1675,10 +1672,10 @@ env.filters.update(
 class JinjaOidcMappingConfig:
     subject_template: Template
     picture_template: Template
-    localpart_template: Optional[Template]
-    display_name_template: Optional[Template]
-    email_template: Optional[Template]
-    extra_attributes: Dict[str, Template]
+    localpart_template: Template | None
+    display_name_template: Template | None
+    email_template: Template | None
+    extra_attributes: dict[str, Template]
     confirm_localpart: bool = False
 
 
@@ -1711,7 +1708,7 @@ class JinjaOidcMappingProvider(OidcMappingProvider[JinjaOidcMappingConfig]):
         subject_template = parse_template_config_with_claim("subject", "sub")
         picture_template = parse_template_config_with_claim("picture", "picture")
 
-        def parse_template_config(option_name: str) -> Optional[Template]:
+        def parse_template_config(option_name: str) -> Template | None:
             if option_name not in config:
                 return None
             try:
@@ -1769,7 +1766,7 @@ class JinjaOidcMappingProvider(OidcMappingProvider[JinjaOidcMappingConfig]):
             # a usable mxid.
             localpart += str(failures) if failures else ""
 
-        def render_template_field(template: Optional[Template]) -> Optional[str]:
+        def render_template_field(template: Template | None) -> str | None:
             if template is None:
                 return None
             return template.render(user=userinfo).strip()
@@ -1778,7 +1775,7 @@ class JinjaOidcMappingProvider(OidcMappingProvider[JinjaOidcMappingConfig]):
         if display_name == "":
             display_name = None
 
-        emails: List[str] = []
+        emails: list[str] = []
         email = render_template_field(self._config.email_template)
         if email:
             emails.append(email)
@@ -1794,7 +1791,7 @@ class JinjaOidcMappingProvider(OidcMappingProvider[JinjaOidcMappingConfig]):
         )
 
     async def get_extra_attributes(self, userinfo: UserInfo, token: Token) -> JsonDict:
-        extras: Dict[str, str] = {}
+        extras: dict[str, str] = {}
         for key, template in self._config.extra_attributes.items():
             try:
                 extras[key] = template.render(user=userinfo).strip()
diff --git a/synapse/handlers/pagination.py b/synapse/handlers/pagination.py
index df1a7e714c..a90ed3193c 100644
--- a/synapse/handlers/pagination.py
+++ b/synapse/handlers/pagination.py
@@ -19,7 +19,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, List, Optional, Set, Tuple, cast
+from typing import TYPE_CHECKING, cast
 
 from twisted.python.failure import Failure
 
@@ -29,7 +29,6 @@ from synapse.api.filtering import Filter
 from synapse.events.utils import SerializeEventConfig
 from synapse.handlers.worker_lock import NEW_EVENT_DURING_PURGE_LOCK_NAME
 from synapse.logging.opentracing import trace
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.rest.admin._base import assert_user_is_admin
 from synapse.streams.config import PaginationConfig
 from synapse.types import (
@@ -92,7 +91,7 @@ class PaginationHandler:
 
         self.pagination_lock = ReadWriteLock()
         # IDs of rooms in which there currently an active purge *or delete* operation.
-        self._purges_in_progress_by_room: Set[str] = set()
+        self._purges_in_progress_by_room: set[str] = set()
         self._event_serializer = hs.get_event_client_serializer()
 
         self._retention_default_max_lifetime = (
@@ -116,10 +115,9 @@ class PaginationHandler:
                 logger.info("Setting up purge job with config: %s", job)
 
                 self.clock.looping_call(
-                    run_as_background_process,
+                    self.hs.run_as_background_process,
                     job.interval,
                     "purge_history_for_rooms_in_range",
-                    self.server_name,
                     self.purge_history_for_rooms_in_range,
                     job.shortest_max_lifetime,
                     job.longest_max_lifetime,
@@ -134,7 +132,7 @@ class PaginationHandler:
         )
 
     async def purge_history_for_rooms_in_range(
-        self, min_ms: Optional[int], max_ms: Optional[int]
+        self, min_ms: int | None, max_ms: int | None
     ) -> None:
         """Purge outdated events from rooms within the given retention range.
 
@@ -244,9 +242,8 @@ class PaginationHandler:
             # We want to purge everything, including local events, and to run the purge in
             # the background so that it's not blocking any other operation apart from
             # other purges in the same room.
-            run_as_background_process(
+            self.hs.run_as_background_process(
                 PURGE_HISTORY_ACTION_NAME,
-                self.server_name,
                 self.purge_history,
                 room_id,
                 token,
@@ -282,7 +279,7 @@ class PaginationHandler:
     async def _purge_history(
         self,
         task: ScheduledTask,
-    ) -> Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]:
+    ) -> tuple[TaskStatus, JsonMapping | None, str | None]:
         """
         Scheduler action to purge some history of a room.
         """
@@ -311,7 +308,7 @@ class PaginationHandler:
         room_id: str,
         token: str,
         delete_local_events: bool,
-    ) -> Optional[str]:
+    ) -> str | None:
         """Carry out a history purge on a room.
 
         Args:
@@ -335,7 +332,7 @@ class PaginationHandler:
             )
             return f.getErrorMessage()
 
-    async def get_delete_task(self, delete_id: str) -> Optional[ScheduledTask]:
+    async def get_delete_task(self, delete_id: str) -> ScheduledTask | None:
         """Get the current status of an active deleting
 
         Args:
@@ -345,8 +342,8 @@ class PaginationHandler:
         return await self._task_scheduler.get_task(delete_id)
 
     async def get_delete_tasks_by_room(
-        self, room_id: str, only_active: Optional[bool] = False
-    ) -> List[ScheduledTask]:
+        self, room_id: str, only_active: bool | None = False
+    ) -> list[ScheduledTask]:
         """Get complete, failed or active delete tasks by room
 
         Args:
@@ -366,7 +363,7 @@ class PaginationHandler:
     async def _purge_room(
         self,
         task: ScheduledTask,
-    ) -> Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]:
+    ) -> tuple[TaskStatus, JsonMapping | None, str | None]:
         """
         Scheduler action to purge a room.
         """
@@ -418,7 +415,7 @@ class PaginationHandler:
         room_id: str,
         pagin_config: PaginationConfig,
         as_client_event: bool = True,
-        event_filter: Optional[Filter] = None,
+        event_filter: Filter | None = None,
         use_admin_priviledge: bool = False,
     ) -> JsonDict:
         """Get messages in a room.
@@ -526,7 +523,7 @@ class PaginationHandler:
             # We use a `Set` because there can be multiple events at a given depth
             # and we only care about looking at the unique continum of depths to
             # find gaps.
-            event_depths: Set[int] = {event.depth for event in events}
+            event_depths: set[int] = {event.depth for event in events}
             sorted_event_depths = sorted(event_depths)
 
             # Inspect the depths of the returned events to see if there are any gaps
@@ -604,9 +601,8 @@ class PaginationHandler:
                 # Otherwise, we can backfill in the background for eventual
                 # consistency's sake but we don't need to block the client waiting
                 # for a costly federation call and processing.
-                run_as_background_process(
+                self.hs.run_as_background_process(
                     "maybe_backfill_in_the_background",
-                    self.server_name,
                     self.hs.get_federation_handler().maybe_backfill,
                     room_id,
                     curr_topo,
@@ -695,7 +691,7 @@ class PaginationHandler:
     async def _shutdown_and_purge_room(
         self,
         task: ScheduledTask,
-    ) -> Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]:
+    ) -> tuple[TaskStatus, JsonMapping | None, str | None]:
         """
         Scheduler action to shutdown and purge a room.
         """
@@ -706,7 +702,7 @@ class PaginationHandler:
 
         room_id = task.resource_id
 
-        async def update_result(result: Optional[JsonMapping]) -> None:
+        async def update_result(result: JsonMapping | None) -> None:
             await self._task_scheduler.update_task(task.id, result=result)
 
         shutdown_result = (
diff --git a/synapse/handlers/presence.py b/synapse/handlers/presence.py
index 4d246fadbd..ca5002cab3 100644
--- a/synapse/handlers/presence.py
+++ b/synapse/handlers/presence.py
@@ -86,14 +86,8 @@ from typing import (
     Callable,
     Collection,
     ContextManager,
-    Dict,
     Generator,
     Iterable,
-    List,
-    Optional,
-    Set,
-    Tuple,
-    Type,
 )
 
 from prometheus_client import Counter
@@ -107,7 +101,6 @@ from synapse.events.presence_router import PresenceRouter
 from synapse.logging.context import run_in_background
 from synapse.metrics import SERVER_NAME_LABEL, LaterGauge
 from synapse.metrics.background_process_metrics import (
-    run_as_background_process,
     wrap_as_background_process,
 )
 from synapse.replication.http.presence import (
@@ -237,7 +230,7 @@ class BasePresenceHandler(abc.ABC):
 
         self._federation_queue = PresenceFederationQueue(hs, self)
 
-        self.VALID_PRESENCE: Tuple[str, ...] = (
+        self.VALID_PRESENCE: tuple[str, ...] = (
             PresenceState.ONLINE,
             PresenceState.UNAVAILABLE,
             PresenceState.OFFLINE,
@@ -254,7 +247,7 @@ class BasePresenceHandler(abc.ABC):
     async def user_syncing(
         self,
         user_id: str,
-        device_id: Optional[str],
+        device_id: str | None,
         affect_presence: bool,
         presence_state: str,
     ) -> ContextManager[None]:
@@ -277,7 +270,7 @@ class BasePresenceHandler(abc.ABC):
     @abc.abstractmethod
     def get_currently_syncing_users_for_replication(
         self,
-    ) -> Iterable[Tuple[str, Optional[str]]]:
+    ) -> Iterable[tuple[str, str | None]]:
         """Get an iterable of syncing users and devices on this worker, to send to the presence handler
 
         This is called when a replication connection is established. It should return
@@ -294,7 +287,7 @@ class BasePresenceHandler(abc.ABC):
 
     async def get_states(
         self, target_user_ids: Iterable[str]
-    ) -> List[UserPresenceState]:
+    ) -> list[UserPresenceState]:
         """Get the presence state for users."""
 
         updates_d = await self.current_state_for_users(target_user_ids)
@@ -307,7 +300,7 @@ class BasePresenceHandler(abc.ABC):
 
     async def current_state_for_users(
         self, user_ids: Iterable[str]
-    ) -> Dict[str, UserPresenceState]:
+    ) -> dict[str, UserPresenceState]:
         """Get the current presence state for multiple users.
 
         Returns:
@@ -346,7 +339,7 @@ class BasePresenceHandler(abc.ABC):
     async def set_state(
         self,
         target_user: UserID,
-        device_id: Optional[str],
+        device_id: str | None,
         state: JsonDict,
         force_notify: bool = False,
         is_sync: bool = False,
@@ -366,7 +359,7 @@ class BasePresenceHandler(abc.ABC):
 
     @abc.abstractmethod
     async def bump_presence_active_time(
-        self, user: UserID, device_id: Optional[str]
+        self, user: UserID, device_id: str | None
     ) -> None:
         """We've seen the user do something that indicates they're interacting
         with the app.
@@ -376,7 +369,7 @@ class BasePresenceHandler(abc.ABC):
         self,
         process_id: str,
         user_id: str,
-        device_id: Optional[str],
+        device_id: str | None,
         is_syncing: bool,
         sync_time_msec: int,
     ) -> None:
@@ -418,7 +411,7 @@ class BasePresenceHandler(abc.ABC):
         return self._federation_queue
 
     async def maybe_send_presence_to_interested_destinations(
-        self, states: List[UserPresenceState]
+        self, states: list[UserPresenceState]
     ) -> None:
         """If this instance is a federation sender, send the states to all
         destinations that are interested. Filters out any states for remote
@@ -502,9 +495,9 @@ class _NullContextManager(ContextManager[None]):
 
     def __exit__(
         self,
-        exc_type: Optional[Type[BaseException]],
-        exc_val: Optional[BaseException],
-        exc_tb: Optional[TracebackType],
+        exc_type: type[BaseException] | None,
+        exc_val: BaseException | None,
+        exc_tb: TracebackType | None,
     ) -> None:
         pass
 
@@ -523,33 +516,27 @@ class WorkerPresenceHandler(BasePresenceHandler):
 
         # The number of ongoing syncs on this process, by (user ID, device ID).
         # Empty if _presence_enabled is false.
-        self._user_device_to_num_current_syncs: Dict[
-            Tuple[str, Optional[str]], int
-        ] = {}
+        self._user_device_to_num_current_syncs: dict[tuple[str, str | None], int] = {}
 
         self.notifier = hs.get_notifier()
         self.instance_id = hs.get_instance_id()
 
         # (user_id, device_id) -> last_sync_ms. Lists the devices that have stopped
         # syncing but we haven't notified the presence writer of that yet
-        self._user_devices_going_offline: Dict[Tuple[str, Optional[str]], int] = {}
+        self._user_devices_going_offline: dict[tuple[str, str | None], int] = {}
 
         self._bump_active_client = ReplicationBumpPresenceActiveTime.make_client(hs)
         self._set_state_client = ReplicationPresenceSetState.make_client(hs)
 
-        self._send_stop_syncing_loop = self.clock.looping_call(
-            self.send_stop_syncing, UPDATE_SYNCING_USERS_MS
-        )
-
-        hs.get_clock().add_system_event_trigger(
-            "before",
-            "shutdown",
-            run_as_background_process,
-            "generic_presence.on_shutdown",
-            self.server_name,
-            self._on_shutdown,
+        self.clock.looping_call(self.send_stop_syncing, UPDATE_SYNCING_USERS_MS)
+
+        hs.register_async_shutdown_handler(
+            phase="before",
+            eventType="shutdown",
+            shutdown_func=self._on_shutdown,
         )
 
+    @wrap_as_background_process("WorkerPresenceHandler._on_shutdown")
     async def _on_shutdown(self) -> None:
         if self._track_presence:
             self.hs.get_replication_command_handler().send_command(
@@ -559,7 +546,7 @@ class WorkerPresenceHandler(BasePresenceHandler):
     def send_user_sync(
         self,
         user_id: str,
-        device_id: Optional[str],
+        device_id: str | None,
         is_syncing: bool,
         last_sync_ms: int,
     ) -> None:
@@ -568,7 +555,7 @@ class WorkerPresenceHandler(BasePresenceHandler):
                 self.instance_id, user_id, device_id, is_syncing, last_sync_ms
             )
 
-    def mark_as_coming_online(self, user_id: str, device_id: Optional[str]) -> None:
+    def mark_as_coming_online(self, user_id: str, device_id: str | None) -> None:
         """A user has started syncing. Send a UserSync to the presence writer,
         unless they had recently stopped syncing.
         """
@@ -578,7 +565,7 @@ class WorkerPresenceHandler(BasePresenceHandler):
             # were offline
             self.send_user_sync(user_id, device_id, True, self.clock.time_msec())
 
-    def mark_as_going_offline(self, user_id: str, device_id: Optional[str]) -> None:
+    def mark_as_going_offline(self, user_id: str, device_id: str | None) -> None:
         """A user has stopped syncing. We wait before notifying the presence
         writer as its likely they'll come back soon. This allows us to avoid
         sending a stopped syncing immediately followed by a started syncing
@@ -601,7 +588,7 @@ class WorkerPresenceHandler(BasePresenceHandler):
     async def user_syncing(
         self,
         user_id: str,
-        device_id: Optional[str],
+        device_id: str | None,
         affect_presence: bool,
         presence_state: str,
     ) -> ContextManager[None]:
@@ -650,7 +637,7 @@ class WorkerPresenceHandler(BasePresenceHandler):
         return _user_syncing()
 
     async def notify_from_replication(
-        self, states: List[UserPresenceState], stream_id: int
+        self, states: list[UserPresenceState], stream_id: int
     ) -> None:
         parties = await get_interested_parties(self.store, self.presence_router, states)
         room_ids_to_states, users_to_states = parties
@@ -709,7 +696,7 @@ class WorkerPresenceHandler(BasePresenceHandler):
 
     def get_currently_syncing_users_for_replication(
         self,
-    ) -> Iterable[Tuple[str, Optional[str]]]:
+    ) -> Iterable[tuple[str, str | None]]:
         return [
             user_id_device_id
             for user_id_device_id, count in self._user_device_to_num_current_syncs.items()
@@ -719,7 +706,7 @@ class WorkerPresenceHandler(BasePresenceHandler):
     async def set_state(
         self,
         target_user: UserID,
-        device_id: Optional[str],
+        device_id: str | None,
         state: JsonDict,
         force_notify: bool = False,
         is_sync: bool = False,
@@ -758,7 +745,7 @@ class WorkerPresenceHandler(BasePresenceHandler):
         )
 
     async def bump_presence_active_time(
-        self, user: UserID, device_id: Optional[str]
+        self, user: UserID, device_id: str | None
     ) -> None:
         """We've seen the user do something that indicates they're interacting
         with the app.
@@ -779,9 +766,7 @@ class WorkerPresenceHandler(BasePresenceHandler):
 class PresenceHandler(BasePresenceHandler):
     def __init__(self, hs: "HomeServer"):
         super().__init__(hs)
-        self.server_name = (
-            hs.hostname
-        )  # nb must be called this for @wrap_as_background_process
+        self.server_name = hs.hostname
         self.wheel_timer: WheelTimer[str] = WheelTimer()
         self.notifier = hs.get_notifier()
 
@@ -797,8 +782,8 @@ class PresenceHandler(BasePresenceHandler):
         )
 
         # The per-device presence state, maps user to devices to per-device presence state.
-        self._user_to_device_to_current_state: Dict[
-            str, Dict[Optional[str], UserDevicePresenceState]
+        self._user_to_device_to_current_state: dict[
+            str, dict[str | None, UserDevicePresenceState]
         ] = {}
 
         now = self.clock.time_msec()
@@ -840,22 +825,17 @@ class PresenceHandler(BasePresenceHandler):
 
         # Set of users who have presence in the `user_to_current_state` that
         # have not yet been persisted
-        self.unpersisted_users_changes: Set[str] = set()
+        self.unpersisted_users_changes: set[str] = set()
 
-        hs.get_clock().add_system_event_trigger(
-            "before",
-            "shutdown",
-            run_as_background_process,
-            "presence.on_shutdown",
-            self.server_name,
-            self._on_shutdown,
+        hs.register_async_shutdown_handler(
+            phase="before",
+            eventType="shutdown",
+            shutdown_func=self._on_shutdown,
         )
 
         # Keeps track of the number of *ongoing* syncs on this process. While
         # this is non zero a user will never go offline.
-        self._user_device_to_num_current_syncs: Dict[
-            Tuple[str, Optional[str]], int
-        ] = {}
+        self._user_device_to_num_current_syncs: dict[tuple[str, str | None], int] = {}
 
         # Keeps track of the number of *ongoing* syncs on other processes.
         #
@@ -867,10 +847,10 @@ class PresenceHandler(BasePresenceHandler):
         # we assume that all the sync requests on that process have stopped.
         # Stored as a dict from process_id to set of (user_id, device_id), and
         # a dict of process_id to millisecond timestamp last updated.
-        self.external_process_to_current_syncs: Dict[
-            str, Set[Tuple[str, Optional[str]]]
+        self.external_process_to_current_syncs: dict[
+            str, set[tuple[str, str | None]]
         ] = {}
-        self.external_process_last_updated_ms: Dict[str, int] = {}
+        self.external_process_last_updated_ms: dict[str, int] = {}
 
         self.external_sync_linearizer = Linearizer(
             name="external_sync_linearizer", clock=self.clock
@@ -881,7 +861,10 @@ class PresenceHandler(BasePresenceHandler):
             # The initial delay is to allow disconnected clients a chance to
             # reconnect before we treat them as offline.
             self.clock.call_later(
-                30, self.clock.looping_call, self._handle_timeouts, 5000
+                30,
+                self.clock.looping_call,
+                self._handle_timeouts,
+                5000,
             )
 
         # Presence information is persisted, whether or not it is being tracked
@@ -908,6 +891,7 @@ class PresenceHandler(BasePresenceHandler):
         self._event_pos = self.store.get_room_max_stream_ordering()
         self._event_processing = False
 
+    @wrap_as_background_process("PresenceHandler._on_shutdown")
     async def _on_shutdown(self) -> None:
         """Gets called when shutting down. This lets us persist any updates that
         we haven't yet persisted, e.g. updates that only changes some internal
@@ -1128,7 +1112,7 @@ class PresenceHandler(BasePresenceHandler):
         return await self._update_states(changes)
 
     async def bump_presence_active_time(
-        self, user: UserID, device_id: Optional[str]
+        self, user: UserID, device_id: str | None
     ) -> None:
         """We've seen the user do something that indicates they're interacting
         with the app.
@@ -1157,7 +1141,7 @@ class PresenceHandler(BasePresenceHandler):
         # Update the user state, this will always update last_active_ts and
         # might update the presence state.
         prev_state = await self.current_state_for_user(user_id)
-        new_fields: Dict[str, Any] = {
+        new_fields: dict[str, Any] = {
             "last_active_ts": now,
             "state": _combine_device_states(devices.values()),
         }
@@ -1167,7 +1151,7 @@ class PresenceHandler(BasePresenceHandler):
     async def user_syncing(
         self,
         user_id: str,
-        device_id: Optional[str],
+        device_id: str | None,
         affect_presence: bool = True,
         presence_state: str = PresenceState.ONLINE,
     ) -> ContextManager[None]:
@@ -1227,7 +1211,7 @@ class PresenceHandler(BasePresenceHandler):
 
     def get_currently_syncing_users_for_replication(
         self,
-    ) -> Iterable[Tuple[str, Optional[str]]]:
+    ) -> Iterable[tuple[str, str | None]]:
         # since we are the process handling presence, there is nothing to do here.
         return []
 
@@ -1235,7 +1219,7 @@ class PresenceHandler(BasePresenceHandler):
         self,
         process_id: str,
         user_id: str,
-        device_id: Optional[str],
+        device_id: str | None,
         is_syncing: bool,
         sync_time_msec: int,
     ) -> None:
@@ -1323,7 +1307,7 @@ class PresenceHandler(BasePresenceHandler):
             )
             self.external_process_last_updated_ms.pop(process_id, None)
 
-    async def _persist_and_notify(self, states: List[UserPresenceState]) -> None:
+    async def _persist_and_notify(self, states: list[UserPresenceState]) -> None:
         """Persist states in the database, poke the notifier and send to
         interested remote servers
         """
@@ -1399,7 +1383,7 @@ class PresenceHandler(BasePresenceHandler):
     async def set_state(
         self,
         target_user: UserID,
-        device_id: Optional[str],
+        device_id: str | None,
         state: JsonDict,
         force_notify: bool = False,
         is_sync: bool = False,
@@ -1483,7 +1467,7 @@ class PresenceHandler(BasePresenceHandler):
 
     async def get_all_presence_updates(
         self, instance_name: str, last_id: int, current_id: int, limit: int
-    ) -> Tuple[List[Tuple[int, list]], int, bool]:
+    ) -> tuple[list[tuple[int, list]], int, bool]:
         """
         Gets a list of presence update rows from between the given stream ids.
         Each row has:
@@ -1539,8 +1523,8 @@ class PresenceHandler(BasePresenceHandler):
             finally:
                 self._event_processing = False
 
-        run_as_background_process(
-            "presence.notify_new_event", self.server_name, _process_presence
+        self.hs.run_as_background_process(
+            "presence.notify_new_event", _process_presence
         )
 
     async def _unsafe_process(self) -> None:
@@ -1568,7 +1552,7 @@ class PresenceHandler(BasePresenceHandler):
                 # We may get multiple deltas for different rooms, but we want to
                 # handle them on a room by room basis, so we batch them up by
                 # room.
-                deltas_by_room: Dict[str, List[StateDelta]] = {}
+                deltas_by_room: dict[str, list[StateDelta]] = {}
                 for delta in deltas:
                     deltas_by_room.setdefault(delta.room_id, []).append(delta)
 
@@ -1582,7 +1566,7 @@ class PresenceHandler(BasePresenceHandler):
                     name="presence", **{SERVER_NAME_LABEL: self.server_name}
                 ).set(max_pos)
 
-    async def _handle_state_delta(self, room_id: str, deltas: List[StateDelta]) -> None:
+    async def _handle_state_delta(self, room_id: str, deltas: list[StateDelta]) -> None:
         """Process current state deltas for the room to find new joins that need
         to be handled.
         """
@@ -1846,16 +1830,16 @@ class PresenceEventSource(EventSource[int, UserPresenceState]):
     async def get_new_events(
         self,
         user: UserID,
-        from_key: Optional[int],
+        from_key: int | None,
         # Having a default limit doesn't match the EventSource API, but some
         # callers do not provide it. It is unused in this class.
         limit: int = 0,
-        room_ids: Optional[StrCollection] = None,
+        room_ids: StrCollection | None = None,
         is_guest: bool = False,
-        explicit_room_id: Optional[str] = None,
+        explicit_room_id: str | None = None,
         include_offline: bool = True,
-        service: Optional[ApplicationService] = None,
-    ) -> Tuple[List[UserPresenceState], int]:
+        service: ApplicationService | None = None,
+    ) -> tuple[list[UserPresenceState], int]:
         # The process for getting presence events are:
         #  1. Get the rooms the user is in.
         #  2. Get the list of user in the rooms.
@@ -2006,8 +1990,8 @@ class PresenceEventSource(EventSource[int, UserPresenceState]):
         self,
         user_id: str,
         include_offline: bool,
-        from_key: Optional[int] = None,
-    ) -> List[UserPresenceState]:
+        from_key: int | None = None,
+    ) -> list[UserPresenceState]:
         """
         Computes the presence updates a user should receive.
 
@@ -2064,7 +2048,7 @@ class PresenceEventSource(EventSource[int, UserPresenceState]):
 
     def _filter_offline_presence_state(
         self, presence_updates: Iterable[UserPresenceState]
-    ) -> List[UserPresenceState]:
+    ) -> list[UserPresenceState]:
         """Given an iterable containing user presence updates, return a list with any offline
         presence states removed.
 
@@ -2085,12 +2069,12 @@ class PresenceEventSource(EventSource[int, UserPresenceState]):
 
 
 def handle_timeouts(
-    user_states: List[UserPresenceState],
+    user_states: list[UserPresenceState],
     is_mine_fn: Callable[[str], bool],
-    syncing_user_devices: AbstractSet[Tuple[str, Optional[str]]],
-    user_to_devices: Dict[str, Dict[Optional[str], UserDevicePresenceState]],
+    syncing_user_devices: AbstractSet[tuple[str, str | None]],
+    user_to_devices: dict[str, dict[str | None, UserDevicePresenceState]],
     now: int,
-) -> List[UserPresenceState]:
+) -> list[UserPresenceState]:
     """Checks the presence of users that have timed out and updates as
     appropriate.
 
@@ -2126,10 +2110,10 @@ def handle_timeouts(
 def handle_timeout(
     state: UserPresenceState,
     is_mine: bool,
-    syncing_device_ids: AbstractSet[Tuple[str, Optional[str]]],
-    user_devices: Dict[Optional[str], UserDevicePresenceState],
+    syncing_device_ids: AbstractSet[tuple[str, str | None]],
+    user_devices: dict[str | None, UserDevicePresenceState],
     now: int,
-) -> Optional[UserPresenceState]:
+) -> UserPresenceState | None:
     """Checks the presence of the user to see if any of the timers have elapsed
 
     Args:
@@ -2224,7 +2208,7 @@ def handle_update(
     wheel_timer: WheelTimer,
     now: int,
     persist: bool,
-) -> Tuple[UserPresenceState, bool, bool]:
+) -> tuple[UserPresenceState, bool, bool]:
     """Given a presence update:
         1. Add any appropriate timers.
         2. Check if we should notify anyone.
@@ -2350,8 +2334,8 @@ def _combine_device_states(
 
 
 async def get_interested_parties(
-    store: DataStore, presence_router: PresenceRouter, states: List[UserPresenceState]
-) -> Tuple[Dict[str, List[UserPresenceState]], Dict[str, List[UserPresenceState]]]:
+    store: DataStore, presence_router: PresenceRouter, states: list[UserPresenceState]
+) -> tuple[dict[str, list[UserPresenceState]], dict[str, list[UserPresenceState]]]:
     """Given a list of states return which entities (rooms, users)
     are interested in the given states.
 
@@ -2364,8 +2348,8 @@ async def get_interested_parties(
         A 2-tuple of `(room_ids_to_states, users_to_states)`,
         with each item being a dict of `entity_name` -> `[UserPresenceState]`
     """
-    room_ids_to_states: Dict[str, List[UserPresenceState]] = {}
-    users_to_states: Dict[str, List[UserPresenceState]] = {}
+    room_ids_to_states: dict[str, list[UserPresenceState]] = {}
+    users_to_states: dict[str, list[UserPresenceState]] = {}
     for state in states:
         room_ids = await store.get_rooms_for_user(state.user_id)
         for room_id in room_ids:
@@ -2388,8 +2372,8 @@ async def get_interested_parties(
 async def get_interested_remotes(
     store: DataStore,
     presence_router: PresenceRouter,
-    states: List[UserPresenceState],
-) -> List[Tuple[StrCollection, Collection[UserPresenceState]]]:
+    states: list[UserPresenceState],
+) -> list[tuple[StrCollection, Collection[UserPresenceState]]]:
     """Given a list of presence states figure out which remote servers
     should be sent which.
 
@@ -2403,14 +2387,14 @@ async def get_interested_remotes(
     Returns:
         A map from destinations to presence states to send to that destination.
     """
-    hosts_and_states: List[Tuple[StrCollection, Collection[UserPresenceState]]] = []
+    hosts_and_states: list[tuple[StrCollection, Collection[UserPresenceState]]] = []
 
     # First we look up the rooms each user is in (as well as any explicit
     # subscriptions), then for each distinct room we look up the remote
     # hosts in those rooms.
     for state in states:
         room_ids = await store.get_rooms_for_user(state.user_id)
-        hosts: Set[str] = set()
+        hosts: set[str] = set()
         for room_id in room_ids:
             room_hosts = await store.get_current_hosts_in_room(room_id)
             hosts.update(room_hosts)
@@ -2479,12 +2463,12 @@ class PresenceFederationQueue:
         # stream_id, destinations, user_ids)`. We don't store the full states
         # for efficiency, and remote workers will already have the full states
         # cached.
-        self._queue: List[Tuple[int, int, StrCollection, Set[str]]] = []
+        self._queue: list[tuple[int, int, StrCollection, set[str]]] = []
 
         self._next_id = 1
 
         # Map from instance name to current token
-        self._current_tokens: Dict[str, int] = {}
+        self._current_tokens: dict[str, int] = {}
 
         if self._queue_presence_updates:
             self._clock.looping_call(self._clear_queue, self._CLEAR_ITEMS_EVERY_MS)
@@ -2553,7 +2537,7 @@ class PresenceFederationQueue:
         from_token: int,
         upto_token: int,
         target_row_count: int,
-    ) -> Tuple[List[Tuple[int, Tuple[str, str]]], int, bool]:
+    ) -> tuple[list[tuple[int, tuple[str, str]]], int, bool]:
         """Get all the updates between the two tokens.
 
         We return rows in the form of `(destination, user_id)` to keep the size
@@ -2589,7 +2573,7 @@ class PresenceFederationQueue:
         # handle the case where `from_token` stream ID has already been dropped.
         start_idx = max(from_token + 1 - self._next_id, -len(self._queue))
 
-        to_send: List[Tuple[int, Tuple[str, str]]] = []
+        to_send: list[tuple[int, tuple[str, str]]] = []
         limited = False
         new_id = upto_token
         for _, stream_id, destinations, user_ids in self._queue[start_idx:]:
@@ -2637,7 +2621,7 @@ class PresenceFederationQueue:
         if not self._federation:
             return
 
-        hosts_to_users: Dict[str, Set[str]] = {}
+        hosts_to_users: dict[str, set[str]] = {}
         for row in rows:
             hosts_to_users.setdefault(row.destination, set()).add(row.user_id)
 
diff --git a/synapse/handlers/profile.py b/synapse/handlers/profile.py
index dbff28e7fb..59904cd995 100644
--- a/synapse/handlers/profile.py
+++ b/synapse/handlers/profile.py
@@ -20,7 +20,7 @@
 #
 import logging
 import random
-from typing import TYPE_CHECKING, List, Optional, Union
+from typing import TYPE_CHECKING
 
 from synapse.api.constants import ProfileFields
 from synapse.api.errors import (
@@ -56,8 +56,8 @@ class ProfileHandler:
 
     def __init__(self, hs: "HomeServer"):
         self.server_name = hs.hostname  # nb must be called this for @cached
+        self.clock = hs.get_clock()  # nb must be called this for @cached
         self.store = hs.get_datastores().main
-        self.clock = hs.get_clock()
         self.hs = hs
 
         self.federation = hs.get_federation_client()
@@ -68,8 +68,8 @@ class ProfileHandler:
         self.user_directory_handler = hs.get_user_directory_handler()
         self.request_ratelimiter = hs.get_request_ratelimiter()
 
-        self.max_avatar_size: Optional[int] = hs.config.server.max_avatar_size
-        self.allowed_avatar_mimetypes: Optional[List[str]] = (
+        self.max_avatar_size: int | None = hs.config.server.max_avatar_size
+        self.allowed_avatar_mimetypes: list[str] | None = (
             hs.config.server.allowed_avatar_mimetypes
         )
 
@@ -133,7 +133,7 @@ class ProfileHandler:
                     raise SynapseError(502, "Failed to fetch profile")
                 raise e.to_synapse_error()
 
-    async def get_displayname(self, target_user: UserID) -> Optional[str]:
+    async def get_displayname(self, target_user: UserID) -> str | None:
         """
         Fetch a user's display name from their profile.
 
@@ -211,7 +211,7 @@ class ProfileHandler:
                 400, "Displayname is too long (max %i)" % (MAX_DISPLAYNAME_LEN,)
             )
 
-        displayname_to_set: Optional[str] = new_displayname.strip()
+        displayname_to_set: str | None = new_displayname.strip()
         if new_displayname == "":
             displayname_to_set = None
 
@@ -238,7 +238,7 @@ class ProfileHandler:
         if propagate:
             await self._update_join_states(requester, target_user)
 
-    async def get_avatar_url(self, target_user: UserID) -> Optional[str]:
+    async def get_avatar_url(self, target_user: UserID) -> str | None:
         """
         Fetch a user's avatar URL from their profile.
 
@@ -316,7 +316,7 @@ class ProfileHandler:
         if not await self.check_avatar_size_and_mime_type(new_avatar_url):
             raise SynapseError(403, "This avatar is not allowed", Codes.FORBIDDEN)
 
-        avatar_url_to_set: Optional[str] = new_avatar_url
+        avatar_url_to_set: str | None = new_avatar_url
         if new_avatar_url == "":
             avatar_url_to_set = None
 
@@ -367,9 +367,9 @@ class ProfileHandler:
             server_name = host
 
         if self._is_mine_server_name(server_name):
-            media_info: Optional[
-                Union[LocalMedia, RemoteMedia]
-            ] = await self.store.get_local_media(media_id)
+            media_info: (
+                LocalMedia | RemoteMedia | None
+            ) = await self.store.get_local_media(media_id)
         else:
             media_info = await self.store.get_cached_remote_media(server_name, media_id)
 
@@ -606,7 +606,7 @@ class ProfileHandler:
                 )
 
     async def check_profile_query_allowed(
-        self, target_user: UserID, requester: Optional[UserID] = None
+        self, target_user: UserID, requester: UserID | None = None
     ) -> None:
         """Checks whether a profile query is allowed. If the
         'require_auth_for_profile_requests' config flag is set to True and a
diff --git a/synapse/handlers/push_rules.py b/synapse/handlers/push_rules.py
index 4ef6a04c51..746c712bac 100644
--- a/synapse/handlers/push_rules.py
+++ b/synapse/handlers/push_rules.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import TYPE_CHECKING, Any, Dict, List, Optional, Union
+from typing import TYPE_CHECKING, Any
 
 import attr
 
@@ -40,7 +40,7 @@ class RuleSpec:
     scope: str
     template: str
     rule_id: str
-    attr: Optional[str]
+    attr: str | None
 
 
 class PushRulesHandler:
@@ -51,7 +51,7 @@ class PushRulesHandler:
         self._main_store = hs.get_datastores().main
 
     async def set_rule_attr(
-        self, user_id: str, spec: RuleSpec, val: Union[bool, JsonDict]
+        self, user_id: str, spec: RuleSpec, val: bool | JsonDict
     ) -> None:
         """Set an attribute (enabled or actions) on an existing push rule.
 
@@ -127,7 +127,7 @@ class PushRulesHandler:
 
     async def push_rules_for_user(
         self, user: UserID
-    ) -> Dict[str, Dict[str, List[Dict[str, Any]]]]:
+    ) -> dict[str, dict[str, list[dict[str, Any]]]]:
         """
         Push rules aren't really account data, but get formatted as such for /sync.
         """
@@ -137,7 +137,7 @@ class PushRulesHandler:
         return rules
 
 
-def check_actions(actions: List[Union[str, JsonDict]]) -> None:
+def check_actions(actions: list[str | JsonDict]) -> None:
     """Check if the given actions are spec compliant.
 
     Args:
diff --git a/synapse/handlers/receipts.py b/synapse/handlers/receipts.py
index c776654d12..f6383baf0b 100644
--- a/synapse/handlers/receipts.py
+++ b/synapse/handlers/receipts.py
@@ -19,7 +19,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, Iterable, List, Optional, Sequence, Tuple
+from typing import TYPE_CHECKING, Iterable, Sequence
 
 from synapse.api.constants import EduTypes, ReceiptTypes
 from synapse.appservice import ApplicationService
@@ -136,10 +136,10 @@ class ReceiptsHandler:
 
         await self._handle_new_receipts(receipts)
 
-    async def _handle_new_receipts(self, receipts: List[ReadReceipt]) -> bool:
+    async def _handle_new_receipts(self, receipts: list[ReadReceipt]) -> bool:
         """Takes a list of receipts, stores them and informs the notifier."""
 
-        receipts_persisted: List[ReadReceipt] = []
+        receipts_persisted: list[ReadReceipt] = []
         for receipt in receipts:
             stream_id = await self.store.insert_receipt(
                 receipt.room_id,
@@ -180,7 +180,7 @@ class ReceiptsHandler:
         receipt_type: str,
         user_id: UserID,
         event_id: str,
-        thread_id: Optional[str],
+        thread_id: str | None,
     ) -> None:
         """Called when a client tells us a local user has read up to the given
         event_id in the room.
@@ -216,7 +216,7 @@ class ReceiptEventSource(EventSource[MultiWriterStreamToken, JsonMapping]):
     @staticmethod
     def filter_out_private_receipts(
         rooms: Sequence[JsonMapping], user_id: str
-    ) -> List[JsonMapping]:
+    ) -> list[JsonMapping]:
         """
         Filters a list of serialized receipts (as returned by /sync and /initialSync)
         and removes private read receipts of other users.
@@ -233,7 +233,7 @@ class ReceiptEventSource(EventSource[MultiWriterStreamToken, JsonMapping]):
             The same as rooms, but filtered.
         """
 
-        result: List[JsonMapping] = []
+        result: list[JsonMapping] = []
 
         # Iterate through each room's receipt content.
         for room in rooms:
@@ -285,9 +285,9 @@ class ReceiptEventSource(EventSource[MultiWriterStreamToken, JsonMapping]):
         limit: int,
         room_ids: Iterable[str],
         is_guest: bool,
-        explicit_room_id: Optional[str] = None,
-        to_key: Optional[MultiWriterStreamToken] = None,
-    ) -> Tuple[List[JsonMapping], MultiWriterStreamToken]:
+        explicit_room_id: str | None = None,
+        to_key: MultiWriterStreamToken | None = None,
+    ) -> tuple[list[JsonMapping], MultiWriterStreamToken]:
         """
         Find read receipts for given rooms (> `from_token` and <= `to_token`)
         """
@@ -313,7 +313,7 @@ class ReceiptEventSource(EventSource[MultiWriterStreamToken, JsonMapping]):
         from_key: MultiWriterStreamToken,
         to_key: MultiWriterStreamToken,
         service: ApplicationService,
-    ) -> Tuple[List[JsonMapping], MultiWriterStreamToken]:
+    ) -> tuple[list[JsonMapping], MultiWriterStreamToken]:
         """Returns a set of new read receipt events that an appservice
         may be interested in.
 
diff --git a/synapse/handlers/register.py b/synapse/handlers/register.py
index 5761a7f70b..139c14dcf4 100644
--- a/synapse/handlers/register.py
+++ b/synapse/handlers/register.py
@@ -23,7 +23,11 @@
 """Contains functions for registering clients."""
 
 import logging
-from typing import TYPE_CHECKING, Iterable, List, Optional, Tuple, TypedDict
+from typing import (
+    TYPE_CHECKING,
+    Iterable,
+    TypedDict,
+)
 
 from prometheus_client import Counter
 
@@ -101,8 +105,8 @@ def init_counters_for_auth_provider(auth_provider_id: str, server_name: str) ->
 class LoginDict(TypedDict):
     device_id: str
     access_token: str
-    valid_until_ms: Optional[int]
-    refresh_token: Optional[str]
+    valid_until_ms: int | None
+    refresh_token: str | None
 
 
 class RegistrationHandler:
@@ -155,8 +159,8 @@ class RegistrationHandler:
     async def check_username(
         self,
         localpart: str,
-        guest_access_token: Optional[str] = None,
-        assigned_user_id: Optional[str] = None,
+        guest_access_token: str | None = None,
+        assigned_user_id: str | None = None,
         inhibit_user_in_use_error: bool = False,
     ) -> None:
         if types.contains_invalid_mxid_characters(localpart):
@@ -223,19 +227,19 @@ class RegistrationHandler:
 
     async def register_user(
         self,
-        localpart: Optional[str] = None,
-        password_hash: Optional[str] = None,
-        guest_access_token: Optional[str] = None,
+        localpart: str | None = None,
+        password_hash: str | None = None,
+        guest_access_token: str | None = None,
         make_guest: bool = False,
         admin: bool = False,
-        threepid: Optional[dict] = None,
-        user_type: Optional[str] = None,
-        default_display_name: Optional[str] = None,
-        address: Optional[str] = None,
-        bind_emails: Optional[Iterable[str]] = None,
+        threepid: dict | None = None,
+        user_type: str | None = None,
+        default_display_name: str | None = None,
+        address: str | None = None,
+        bind_emails: Iterable[str] | None = None,
         by_admin: bool = False,
-        user_agent_ips: Optional[List[Tuple[str, str]]] = None,
-        auth_provider_id: Optional[str] = None,
+        user_agent_ips: list[tuple[str, str]] | None = None,
+        auth_provider_id: str | None = None,
         approved: bool = False,
     ) -> str:
         """Registers a new client on the server.
@@ -648,7 +652,7 @@ class RegistrationHandler:
 
     async def appservice_register(
         self, user_localpart: str, as_token: str
-    ) -> Tuple[str, ApplicationService]:
+    ) -> tuple[str, ApplicationService]:
         user = UserID(user_localpart, self.hs.hostname)
         user_id = user.to_string()
         service = self.store.get_app_service_by_token(as_token)
@@ -674,7 +678,7 @@ class RegistrationHandler:
         return (user_id, service)
 
     def check_user_id_not_appservice_exclusive(
-        self, user_id: str, allowed_appservice: Optional[ApplicationService] = None
+        self, user_id: str, allowed_appservice: ApplicationService | None = None
     ) -> None:
         # don't allow people to register the server notices mxid
         if self._server_notices_mxid is not None:
@@ -699,7 +703,7 @@ class RegistrationHandler:
                     errcode=Codes.EXCLUSIVE,
                 )
 
-    async def check_registration_ratelimit(self, address: Optional[str]) -> None:
+    async def check_registration_ratelimit(self, address: str | None) -> None:
         """A simple helper method to check whether the registration rate limit has been hit
         for a given IP address
 
@@ -718,14 +722,14 @@ class RegistrationHandler:
     async def register_with_store(
         self,
         user_id: str,
-        password_hash: Optional[str] = None,
+        password_hash: str | None = None,
         was_guest: bool = False,
         make_guest: bool = False,
-        appservice_id: Optional[str] = None,
-        create_profile_with_displayname: Optional[str] = None,
+        appservice_id: str | None = None,
+        create_profile_with_displayname: str | None = None,
         admin: bool = False,
-        user_type: Optional[str] = None,
-        address: Optional[str] = None,
+        user_type: str | None = None,
+        address: str | None = None,
         shadow_banned: bool = False,
         approved: bool = False,
     ) -> None:
@@ -766,14 +770,14 @@ class RegistrationHandler:
     async def register_device(
         self,
         user_id: str,
-        device_id: Optional[str],
-        initial_display_name: Optional[str],
+        device_id: str | None,
+        initial_display_name: str | None,
         is_guest: bool = False,
         is_appservice_ghost: bool = False,
-        auth_provider_id: Optional[str] = None,
+        auth_provider_id: str | None = None,
         should_issue_refresh_token: bool = False,
-        auth_provider_session_id: Optional[str] = None,
-    ) -> Tuple[str, str, Optional[int], Optional[str]]:
+        auth_provider_session_id: str | None = None,
+    ) -> tuple[str, str, int | None, str | None]:
         """Register a device for a user and generate an access token.
 
         The access token will be limited by the homeserver's session_lifetime config.
@@ -816,13 +820,13 @@ class RegistrationHandler:
     async def register_device_inner(
         self,
         user_id: str,
-        device_id: Optional[str],
-        initial_display_name: Optional[str],
+        device_id: str | None,
+        initial_display_name: str | None,
         is_guest: bool = False,
         is_appservice_ghost: bool = False,
         should_issue_refresh_token: bool = False,
-        auth_provider_id: Optional[str] = None,
-        auth_provider_session_id: Optional[str] = None,
+        auth_provider_id: str | None = None,
+        auth_provider_session_id: str | None = None,
     ) -> LoginDict:
         """Helper for register_device
 
@@ -922,7 +926,7 @@ class RegistrationHandler:
         }
 
     async def post_registration_actions(
-        self, user_id: str, auth_result: dict, access_token: Optional[str]
+        self, user_id: str, auth_result: dict, access_token: str | None
     ) -> None:
         """A user has completed registration
 
@@ -972,7 +976,7 @@ class RegistrationHandler:
         await self.post_consent_actions(user_id)
 
     async def _register_email_threepid(
-        self, user_id: str, threepid: dict, token: Optional[str]
+        self, user_id: str, threepid: dict, token: str | None
     ) -> None:
         """Add an email address as a 3pid identifier
 
diff --git a/synapse/handlers/relations.py b/synapse/handlers/relations.py
index 54901b5645..1c5f2f4980 100644
--- a/synapse/handlers/relations.py
+++ b/synapse/handlers/relations.py
@@ -20,15 +20,12 @@
 #
 import enum
 import logging
+from collections import defaultdict
 from typing import (
     TYPE_CHECKING,
     Collection,
-    Dict,
-    FrozenSet,
     Iterable,
-    List,
     Mapping,
-    Optional,
     Sequence,
 )
 
@@ -40,7 +37,11 @@ from synapse.events import EventBase, relation_from_event
 from synapse.events.utils import SerializeEventConfig
 from synapse.logging.context import make_deferred_yieldable, run_in_background
 from synapse.logging.opentracing import trace
-from synapse.storage.databases.main.relations import ThreadsNextBatch, _RelatedEvent
+from synapse.storage.databases.main.relations import (
+    ThreadsNextBatch,
+    ThreadUpdateInfo,
+    _RelatedEvent,
+)
 from synapse.streams.config import PaginationConfig
 from synapse.types import JsonDict, Requester, UserID
 from synapse.util.async_helpers import gather_results
@@ -52,6 +53,11 @@ if TYPE_CHECKING:
 
 logger = logging.getLogger(__name__)
 
+# Type aliases for thread update processing
+ThreadUpdatesMap = dict[str, list[ThreadUpdateInfo]]
+ThreadRootsMap = dict[str, EventBase]
+AggregationsMap = dict[str, "BundledAggregations"]
+
 
 class ThreadsListInclude(str, enum.Enum):
     """Valid values for the 'include' flag of /threads."""
@@ -78,9 +84,9 @@ class BundledAggregations:
     Some values require additional processing during serialization.
     """
 
-    references: Optional[JsonDict] = None
-    replace: Optional[EventBase] = None
-    thread: Optional[_ThreadAggregation] = None
+    references: JsonDict | None = None
+    replace: EventBase | None = None
+    thread: _ThreadAggregation | None = None
 
     def __bool__(self) -> bool:
         return bool(self.references or self.replace or self.thread)
@@ -104,8 +110,8 @@ class RelationsHandler:
         pagin_config: PaginationConfig,
         recurse: bool,
         include_original_event: bool,
-        relation_type: Optional[str] = None,
-        event_type: Optional[str] = None,
+        relation_type: str | None = None,
+        event_type: str | None = None,
     ) -> JsonDict:
         """Get related events of a event, ordered by topological ordering.
 
@@ -210,7 +216,7 @@ class RelationsHandler:
         requester: Requester,
         event_id: str,
         initial_redaction_event: EventBase,
-        relation_types: List[str],
+        relation_types: list[str],
     ) -> None:
         """Redacts all events related to the given event ID with one of the given
         relation types.
@@ -265,7 +271,7 @@ class RelationsHandler:
                 )
 
     async def get_references_for_events(
-        self, event_ids: Collection[str], ignored_users: FrozenSet[str] = frozenset()
+        self, event_ids: Collection[str], ignored_users: frozenset[str] = frozenset()
     ) -> Mapping[str, Sequence[_RelatedEvent]]:
         """Get a list of references to the given events.
 
@@ -306,11 +312,11 @@ class RelationsHandler:
 
     async def _get_threads_for_events(
         self,
-        events_by_id: Dict[str, EventBase],
-        relations_by_id: Dict[str, str],
+        events_by_id: dict[str, EventBase],
+        relations_by_id: dict[str, str],
         user_id: str,
-        ignored_users: FrozenSet[str],
-    ) -> Dict[str, _ThreadAggregation]:
+        ignored_users: frozenset[str],
+    ) -> dict[str, _ThreadAggregation]:
         """Get the bundled aggregations for threads for the requested events.
 
         Args:
@@ -435,7 +441,7 @@ class RelationsHandler:
     @trace
     async def get_bundled_aggregations(
         self, events: Iterable[EventBase], user_id: str
-    ) -> Dict[str, BundledAggregations]:
+    ) -> dict[str, BundledAggregations]:
         """Generate bundled aggregations for events.
 
         Args:
@@ -454,7 +460,7 @@ class RelationsHandler:
         # De-duplicated events by ID to handle the same event requested multiple times.
         events_by_id = {}
         # A map of event ID to the relation in that event, if there is one.
-        relations_by_id: Dict[str, str] = {}
+        relations_by_id: dict[str, str] = {}
         for event in events:
             # State events do not get bundled aggregations.
             if event.is_state():
@@ -477,7 +483,7 @@ class RelationsHandler:
             events_by_id[event.event_id] = event
 
         # event ID -> bundled aggregation in non-serialized form.
-        results: Dict[str, BundledAggregations] = {}
+        results: dict[str, BundledAggregations] = {}
 
         # Fetch any ignored users of the requesting user.
         ignored_users = await self._main_store.ignored_users(user_id)
@@ -548,13 +554,87 @@ class RelationsHandler:
 
         return results
 
+    async def process_thread_updates_for_visibility(
+        self,
+        all_thread_updates: ThreadUpdatesMap,
+        user_id: str,
+    ) -> ThreadUpdatesMap:
+        """Process thread updates by filtering for visibility.
+
+        Takes raw thread updates from storage and filters them based on whether the
+        user can see the events. Preserves the ordering of updates within each thread.
+
+        Args:
+            all_thread_updates: Map of thread_id to list of ThreadUpdateInfo objects
+            user_id: The user ID to filter events for
+
+        Returns:
+            Filtered map of thread_id to list of ThreadUpdateInfo objects, containing
+            only updates for events the user can see.
+        """
+        # Build a mapping of event_id -> (thread_id, update) for efficient lookup
+        # during visibility filtering.
+        event_to_thread_map: dict[str, tuple[str, ThreadUpdateInfo]] = {}
+        for thread_id, updates in all_thread_updates.items():
+            for update in updates:
+                event_to_thread_map[update.event_id] = (thread_id, update)
+
+        # Fetch and filter events for visibility
+        all_events = await self._main_store.get_events_as_list(
+            event_to_thread_map.keys()
+        )
+        filtered_events = await filter_events_for_client(
+            self._storage_controllers, user_id, all_events
+        )
+
+        # Rebuild thread updates from filtered events
+        filtered_updates: ThreadUpdatesMap = defaultdict(list)
+        for event in filtered_events:
+            if event.event_id in event_to_thread_map:
+                thread_id, update = event_to_thread_map[event.event_id]
+                filtered_updates[thread_id].append(update)
+
+        return filtered_updates
+
+    async def fetch_thread_roots_and_aggregations(
+        self,
+        thread_ids: Iterable[str],
+        user_id: str,
+    ) -> tuple[ThreadRootsMap, AggregationsMap]:
+        """Fetch thread root events and their bundled aggregations.
+
+        Args:
+            thread_ids: The thread root event IDs to fetch
+            user_id: The user ID requesting the aggregations
+
+        Returns:
+            A tuple of:
+            - Map of event_id to EventBase for thread root events
+            - Map of event_id to BundledAggregations for those events
+        """
+        # Fetch thread root events
+        thread_root_events = await self._main_store.get_events_as_list(thread_ids)
+        thread_root_event_map: ThreadRootsMap = {
+            e.event_id: e for e in thread_root_events
+        }
+
+        # Fetch bundled aggregations for the thread roots
+        aggregations_map: AggregationsMap = {}
+        if thread_root_event_map:
+            aggregations_map = await self.get_bundled_aggregations(
+                thread_root_event_map.values(),
+                user_id,
+            )
+
+        return thread_root_event_map, aggregations_map
+
     async def get_threads(
         self,
         requester: Requester,
         room_id: str,
         include: ThreadsListInclude,
         limit: int = 5,
-        from_token: Optional[ThreadsNextBatch] = None,
+        from_token: ThreadsNextBatch | None = None,
     ) -> JsonDict:
         """Get related events of a event, ordered by topological ordering.
 
diff --git a/synapse/handlers/room.py b/synapse/handlers/room.py
index db6dc5efd0..d62ad5393f 100644
--- a/synapse/handlers/room.py
+++ b/synapse/handlers/room.py
@@ -33,10 +33,6 @@ from typing import (
     Any,
     Awaitable,
     Callable,
-    Dict,
-    List,
-    Optional,
-    Tuple,
     cast,
 )
 
@@ -112,11 +108,11 @@ FIVE_MINUTES_IN_MS = 5 * 60 * 1000
 
 @attr.s(slots=True, frozen=True, auto_attribs=True)
 class EventContext:
-    events_before: List[EventBase]
+    events_before: list[EventBase]
     event: EventBase
-    events_after: List[EventBase]
-    state: List[EventBase]
-    aggregations: Dict[str, BundledAggregations]
+    events_after: list[EventBase]
+    state: list[EventBase]
+    aggregations: dict[str, BundledAggregations]
     start: str
     end: str
 
@@ -143,7 +139,7 @@ class RoomCreationHandler:
         )
 
         # Room state based off defined presets
-        self._presets_dict: Dict[str, Dict[str, Any]] = {
+        self._presets_dict: dict[str, dict[str, Any]] = {
             RoomCreationPreset.PRIVATE_CHAT: {
                 "join_rules": JoinRules.INVITE,
                 "history_visibility": HistoryVisibility.SHARED,
@@ -184,7 +180,7 @@ class RoomCreationHandler:
         # If a user tries to update the same room multiple times in quick
         # succession, only process the first attempt and return its result to
         # subsequent requests
-        self._upgrade_response_cache: ResponseCache[Tuple[str, str]] = ResponseCache(
+        self._upgrade_response_cache: ResponseCache[tuple[str, str]] = ResponseCache(
             clock=hs.get_clock(),
             name="room_upgrade",
             server_name=self.server_name,
@@ -201,7 +197,7 @@ class RoomCreationHandler:
         requester: Requester,
         old_room_id: str,
         new_version: RoomVersion,
-        additional_creators: Optional[List[str]],
+        additional_creators: list[str] | None,
         auto_member: bool = False,
         ratelimit: bool = True,
     ) -> str:
@@ -339,15 +335,16 @@ class RoomCreationHandler:
         self,
         requester: Requester,
         old_room_id: str,
-        old_room: Tuple[bool, str, bool],
+        old_room: tuple[bool, str, bool],
         new_room_id: str,
         new_version: RoomVersion,
         tombstone_event: EventBase,
         tombstone_context: synapse.events.snapshot.EventContext,
-        additional_creators: Optional[List[str]],
-        creation_event_with_context: Optional[
-            Tuple[EventBase, synapse.events.snapshot.EventContext]
-        ] = None,
+        additional_creators: list[str] | None,
+        creation_event_with_context: tuple[
+            EventBase, synapse.events.snapshot.EventContext
+        ]
+        | None = None,
         auto_member: bool = False,
     ) -> str:
         """
@@ -437,7 +434,7 @@ class RoomCreationHandler:
         old_room_id: str,
         new_room_id: str,
         old_room_state: StateMap[str],
-        additional_creators: Optional[List[str]],
+        additional_creators: list[str] | None,
     ) -> None:
         """Send updated power levels in both rooms after an upgrade
 
@@ -527,9 +524,9 @@ class RoomCreationHandler:
     def _calculate_upgraded_room_creation_content(
         self,
         old_room_create_event: EventBase,
-        tombstone_event_id: Optional[str],
+        tombstone_event_id: str | None,
         new_room_version: RoomVersion,
-        additional_creators: Optional[List[str]],
+        additional_creators: list[str] | None,
     ) -> JsonDict:
         creation_content: JsonDict = {
             "room_version": new_room_version.identifier,
@@ -561,10 +558,11 @@ class RoomCreationHandler:
         new_room_id: str,
         new_room_version: RoomVersion,
         tombstone_event_id: str,
-        additional_creators: Optional[List[str]],
-        creation_event_with_context: Optional[
-            Tuple[EventBase, synapse.events.snapshot.EventContext]
-        ] = None,
+        additional_creators: list[str] | None,
+        creation_event_with_context: tuple[
+            EventBase, synapse.events.snapshot.EventContext
+        ]
+        | None = None,
         auto_member: bool = False,
     ) -> None:
         """Populate a new room based on an old room
@@ -600,7 +598,7 @@ class RoomCreationHandler:
         initial_state: MutableStateMap = {}
 
         # Replicate relevant room events
-        types_to_copy: List[Tuple[str, Optional[str]]] = [
+        types_to_copy: list[tuple[str, str | None]] = [
             (EventTypes.JoinRules, ""),
             (EventTypes.Name, ""),
             (EventTypes.Topic, ""),
@@ -1042,9 +1040,9 @@ class RoomCreationHandler:
         requester: Requester,
         config: JsonDict,
         ratelimit: bool = True,
-        creator_join_profile: Optional[JsonDict] = None,
+        creator_join_profile: JsonDict | None = None,
         ignore_forced_encryption: bool = False,
-    ) -> Tuple[str, Optional[RoomAlias], int]:
+    ) -> tuple[str, RoomAlias | None, int]:
         """Creates a new room.
 
         Args:
@@ -1394,7 +1392,7 @@ class RoomCreationHandler:
         creation_content: JsonDict,
         is_public: bool,
         room_version: RoomVersion,
-    ) -> Tuple[EventBase, synapse.events.snapshot.EventContext]:
+    ) -> tuple[EventBase, synapse.events.snapshot.EventContext]:
         (
             creation_event,
             new_unpersisted_context,
@@ -1426,17 +1424,18 @@ class RoomCreationHandler:
         room_id: str,
         room_version: RoomVersion,
         room_config: JsonDict,
-        invite_list: List[str],
+        invite_list: list[str],
         initial_state: MutableStateMap,
         creation_content: JsonDict,
-        room_alias: Optional[RoomAlias] = None,
-        power_level_content_override: Optional[JsonDict] = None,
-        creator_join_profile: Optional[JsonDict] = None,
+        room_alias: RoomAlias | None = None,
+        power_level_content_override: JsonDict | None = None,
+        creator_join_profile: JsonDict | None = None,
         ignore_forced_encryption: bool = False,
-        creation_event_with_context: Optional[
-            Tuple[EventBase, synapse.events.snapshot.EventContext]
-        ] = None,
-    ) -> Tuple[int, str, int]:
+        creation_event_with_context: tuple[
+            EventBase, synapse.events.snapshot.EventContext
+        ]
+        | None = None,
+    ) -> tuple[int, str, int]:
         """Sends the initial events into a new room. Sends the room creation, membership,
         and power level events into the room sequentially, then creates and batches up the
         rest of the events to persist as a batch to the DB.
@@ -1485,7 +1484,7 @@ class RoomCreationHandler:
         depth = 1
 
         # the most recently created event
-        prev_event: List[str] = []
+        prev_event: list[str] = []
         # a map of event types, state keys -> event_ids. We collect these mappings this as events are
         # created (but not persisted to the db) to determine state for future created events
         # (as this info can't be pulled from the db)
@@ -1496,7 +1495,7 @@ class RoomCreationHandler:
             content: JsonDict,
             for_batch: bool,
             **kwargs: Any,
-        ) -> Tuple[EventBase, synapse.events.snapshot.UnpersistedEventContextBase]:
+        ) -> tuple[EventBase, synapse.events.snapshot.UnpersistedEventContextBase]:
             """
             Creates an event and associated event context.
             Args:
@@ -1792,7 +1791,7 @@ class RoomCreationHandler:
                             f"You cannot create an encrypted room. user_level ({room_admin_level}) < send_level ({encryption_level})",
                         )
 
-    def _room_preset_config(self, room_config: JsonDict) -> Tuple[str, dict]:
+    def _room_preset_config(self, room_config: JsonDict) -> tuple[str, dict]:
         # The spec says rooms should default to private visibility if
         # `visibility` is not specified.
         visibility = room_config.get("visibility", "private")
@@ -1814,9 +1813,9 @@ class RoomCreationHandler:
 
     def _remove_creators_from_pl_users_map(
         self,
-        users_map: Dict[str, int],
+        users_map: dict[str, int],
         creator: str,
-        additional_creators: Optional[List[str]],
+        additional_creators: list[str] | None,
     ) -> None:
         creators = [creator]
         if additional_creators:
@@ -1883,9 +1882,9 @@ class RoomContextHandler:
         room_id: str,
         event_id: str,
         limit: int,
-        event_filter: Optional[Filter],
+        event_filter: Filter | None,
         use_admin_priviledge: bool = False,
-    ) -> Optional[EventContext]:
+    ) -> EventContext | None:
         """Retrieves events, pagination tokens and state around a given event
         in a room.
 
@@ -1916,7 +1915,7 @@ class RoomContextHandler:
         # The user is peeking if they aren't in the room already
         is_peeking = not is_user_in_room
 
-        async def filter_evts(events: List[EventBase]) -> List[EventBase]:
+        async def filter_evts(events: list[EventBase]) -> list[EventBase]:
             if use_admin_priviledge:
                 return events
             return await filter_events_for_client(
@@ -2021,7 +2020,7 @@ class TimestampLookupHandler:
         room_id: str,
         timestamp: int,
         direction: Direction,
-    ) -> Tuple[str, int]:
+    ) -> tuple[str, int]:
         """Find the closest event to the given timestamp in the given direction.
         If we can't find an event locally or the event we have locally is next to a gap,
         it will ask other federated homeservers for an event.
@@ -2171,8 +2170,8 @@ class RoomEventSource(EventSource[RoomStreamToken, EventBase]):
         limit: int,
         room_ids: StrCollection,
         is_guest: bool,
-        explicit_room_id: Optional[str] = None,
-    ) -> Tuple[List[EventBase], RoomStreamToken]:
+        explicit_room_id: str | None = None,
+    ) -> tuple[list[EventBase], RoomStreamToken]:
         # We just ignore the key for now.
 
         to_key = self.get_current_key()
@@ -2247,11 +2246,10 @@ class RoomShutdownHandler:
         self,
         room_id: str,
         params: ShutdownRoomParams,
-        result: Optional[ShutdownRoomResponse] = None,
-        update_result_fct: Optional[
-            Callable[[Optional[JsonMapping]], Awaitable[None]]
-        ] = None,
-    ) -> Optional[ShutdownRoomResponse]:
+        result: ShutdownRoomResponse | None = None,
+        update_result_fct: Callable[[JsonMapping | None], Awaitable[None]]
+        | None = None,
+    ) -> ShutdownRoomResponse | None:
         """
         Shuts down a room. Moves all joined local users and room aliases automatically
         to a new room if `new_room_user_id` is set. Otherwise local users only
diff --git a/synapse/handlers/room_list.py b/synapse/handlers/room_list.py
index 9d4307fb07..6377931b39 100644
--- a/synapse/handlers/room_list.py
+++ b/synapse/handlers/room_list.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Any, List, Optional, Tuple
+from typing import TYPE_CHECKING, Any
 
 import attr
 import msgpack
@@ -67,14 +67,14 @@ class RoomListHandler:
         self.hs = hs
         self.enable_room_list_search = hs.config.roomdirectory.enable_room_list_search
         self.response_cache: ResponseCache[
-            Tuple[Optional[int], Optional[str], Optional[ThirdPartyInstanceID]]
+            tuple[int | None, str | None, ThirdPartyInstanceID | None]
         ] = ResponseCache(
             clock=hs.get_clock(),
             name="room_list",
             server_name=self.server_name,
         )
         self.remote_response_cache: ResponseCache[
-            Tuple[str, Optional[int], Optional[str], bool, Optional[str]]
+            tuple[str, int | None, str | None, bool, str | None]
         ] = ResponseCache(
             clock=hs.get_clock(),
             name="remote_room_list",
@@ -84,11 +84,11 @@ class RoomListHandler:
 
     async def get_local_public_room_list(
         self,
-        limit: Optional[int] = None,
-        since_token: Optional[str] = None,
-        search_filter: Optional[dict] = None,
-        network_tuple: Optional[ThirdPartyInstanceID] = EMPTY_THIRD_PARTY_ID,
-        from_federation_origin: Optional[str] = None,
+        limit: int | None = None,
+        since_token: str | None = None,
+        search_filter: dict | None = None,
+        network_tuple: ThirdPartyInstanceID | None = EMPTY_THIRD_PARTY_ID,
+        from_federation_origin: str | None = None,
     ) -> JsonDict:
         """Generate a local public room list.
 
@@ -150,10 +150,10 @@ class RoomListHandler:
     async def _get_public_room_list(
         self,
         limit: int,
-        since_token: Optional[str] = None,
-        search_filter: Optional[dict] = None,
-        network_tuple: Optional[ThirdPartyInstanceID] = EMPTY_THIRD_PARTY_ID,
-        from_federation_origin: Optional[str] = None,
+        since_token: str | None = None,
+        search_filter: dict | None = None,
+        network_tuple: ThirdPartyInstanceID | None = EMPTY_THIRD_PARTY_ID,
+        from_federation_origin: str | None = None,
     ) -> JsonDict:
         """Generate a public room list.
         Args:
@@ -175,7 +175,7 @@ class RoomListHandler:
         if since_token:
             batch_token = RoomListNextBatch.from_token(since_token)
 
-            bounds: Optional[Tuple[int, str]] = (
+            bounds: tuple[int, str] | None = (
                 batch_token.last_joined_members,
                 batch_token.last_room_id,
             )
@@ -226,7 +226,7 @@ class RoomListHandler:
             return {k: v for k, v in entry.items() if v is not None}
 
         # Build a list of up to `limit` entries.
-        room_entries: List[JsonDict] = []
+        room_entries: list[JsonDict] = []
         rooms_iterator = results if forwards else reversed(results)
 
         # Track the first and last 'considered' rooms so that we can provide correct
@@ -235,8 +235,8 @@ class RoomListHandler:
         # `len(room_entries) >= limit` and we might be left with rooms we didn't
         # 'consider' (iterate over) and we should save those rooms for the next
         # batch.
-        first_considered_room: Optional[LargestRoomStats] = None
-        last_considered_room: Optional[LargestRoomStats] = None
+        first_considered_room: LargestRoomStats | None = None
+        last_considered_room: LargestRoomStats | None = None
         cut_off_due_to_limit: bool = False
 
         for room_result in rooms_iterator:
@@ -349,7 +349,7 @@ class RoomListHandler:
         cache_context: _CacheContext,
         with_alias: bool = True,
         allow_private: bool = False,
-    ) -> Optional[JsonMapping]:
+    ) -> JsonMapping | None:
         """Returns the entry for a room
 
         Args:
@@ -455,11 +455,11 @@ class RoomListHandler:
     async def get_remote_public_room_list(
         self,
         server_name: str,
-        limit: Optional[int] = None,
-        since_token: Optional[str] = None,
-        search_filter: Optional[dict] = None,
+        limit: int | None = None,
+        since_token: str | None = None,
+        search_filter: dict | None = None,
         include_all_networks: bool = False,
-        third_party_instance_id: Optional[str] = None,
+        third_party_instance_id: str | None = None,
     ) -> JsonDict:
         """Get the public room list from remote server
 
@@ -531,11 +531,11 @@ class RoomListHandler:
     async def _get_remote_list_cached(
         self,
         server_name: str,
-        limit: Optional[int] = None,
-        since_token: Optional[str] = None,
-        search_filter: Optional[dict] = None,
+        limit: int | None = None,
+        since_token: str | None = None,
+        search_filter: dict | None = None,
         include_all_networks: bool = False,
-        third_party_instance_id: Optional[str] = None,
+        third_party_instance_id: str | None = None,
     ) -> JsonDict:
         """Wrapper around FederationClient.get_public_rooms that caches the
         result.
diff --git a/synapse/handlers/room_member.py b/synapse/handlers/room_member.py
index 623823acb0..d5f72c1732 100644
--- a/synapse/handlers/room_member.py
+++ b/synapse/handlers/room_member.py
@@ -23,7 +23,7 @@ import abc
 import logging
 import random
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Iterable, List, Optional, Set, Tuple
+from typing import TYPE_CHECKING, Iterable
 
 from synapse import types
 from synapse.api.constants import (
@@ -50,7 +50,6 @@ from synapse.handlers.state_deltas import MatchChange, StateDeltasHandler
 from synapse.handlers.worker_lock import NEW_EVENT_DURING_PURGE_LOCK_NAME
 from synapse.logging import opentracing
 from synapse.metrics import SERVER_NAME_LABEL, event_processing_positions
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.replication.http.push import ReplicationCopyPusherRestServlet
 from synapse.storage.databases.main.state_deltas import StateDelta
 from synapse.storage.invite_rule import InviteRule
@@ -218,11 +217,11 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
     async def _remote_join(
         self,
         requester: Requester,
-        remote_room_hosts: List[str],
+        remote_room_hosts: list[str],
         room_id: str,
         user: UserID,
         content: dict,
-    ) -> Tuple[str, int]:
+    ) -> tuple[str, int]:
         """Try and join a room that this server is not in
 
         Args:
@@ -242,11 +241,11 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
     async def remote_knock(
         self,
         requester: Requester,
-        remote_room_hosts: List[str],
+        remote_room_hosts: list[str],
         room_id: str,
         user: UserID,
         content: dict,
-    ) -> Tuple[str, int]:
+    ) -> tuple[str, int]:
         """Try and knock on a room that this server is not in
 
         Args:
@@ -261,10 +260,10 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
     async def remote_reject_invite(
         self,
         invite_event_id: str,
-        txn_id: Optional[str],
+        txn_id: str | None,
         requester: Requester,
         content: JsonDict,
-    ) -> Tuple[str, int]:
+    ) -> tuple[str, int]:
         """
         Rejects an out-of-band invite we have received from a remote server
 
@@ -284,10 +283,10 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
     async def remote_rescind_knock(
         self,
         knock_event_id: str,
-        txn_id: Optional[str],
+        txn_id: str | None,
         requester: Requester,
         content: JsonDict,
-    ) -> Tuple[str, int]:
+    ) -> tuple[str, int]:
         """Rescind a local knock made on a remote room.
 
         Args:
@@ -350,8 +349,8 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
 
     async def ratelimit_multiple_invites(
         self,
-        requester: Optional[Requester],
-        room_id: Optional[str],
+        requester: Requester | None,
+        room_id: str | None,
         n_invites: int,
         update: bool = True,
     ) -> None:
@@ -375,8 +374,8 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
 
     async def ratelimit_invite(
         self,
-        requester: Optional[Requester],
-        room_id: Optional[str],
+        requester: Requester | None,
+        room_id: str | None,
         invitee_user_id: str,
     ) -> None:
         """Ratelimit invites by room and by target user.
@@ -397,16 +396,16 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
         target: UserID,
         room_id: str,
         membership: str,
-        prev_event_ids: Optional[List[str]] = None,
-        state_event_ids: Optional[List[str]] = None,
-        depth: Optional[int] = None,
-        txn_id: Optional[str] = None,
+        prev_event_ids: list[str] | None = None,
+        state_event_ids: list[str] | None = None,
+        depth: int | None = None,
+        txn_id: str | None = None,
         ratelimit: bool = True,
-        content: Optional[dict] = None,
+        content: dict | None = None,
         require_consent: bool = True,
         outlier: bool = False,
-        origin_server_ts: Optional[int] = None,
-    ) -> Tuple[str, int]:
+        origin_server_ts: int | None = None,
+    ) -> tuple[str, int]:
         """
         Internal membership update function to get an existing event or create
         and persist a new event for the new membership change.
@@ -573,19 +572,19 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
         target: UserID,
         room_id: str,
         action: str,
-        txn_id: Optional[str] = None,
-        remote_room_hosts: Optional[List[str]] = None,
-        third_party_signed: Optional[dict] = None,
+        txn_id: str | None = None,
+        remote_room_hosts: list[str] | None = None,
+        third_party_signed: dict | None = None,
         ratelimit: bool = True,
-        content: Optional[dict] = None,
+        content: dict | None = None,
         new_room: bool = False,
         require_consent: bool = True,
         outlier: bool = False,
-        prev_event_ids: Optional[List[str]] = None,
-        state_event_ids: Optional[List[str]] = None,
-        depth: Optional[int] = None,
-        origin_server_ts: Optional[int] = None,
-    ) -> Tuple[str, int]:
+        prev_event_ids: list[str] | None = None,
+        state_event_ids: list[str] | None = None,
+        depth: int | None = None,
+        origin_server_ts: int | None = None,
+    ) -> tuple[str, int]:
         """Update a user's membership in a room.
 
         Params:
@@ -687,19 +686,19 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
         target: UserID,
         room_id: str,
         action: str,
-        txn_id: Optional[str] = None,
-        remote_room_hosts: Optional[List[str]] = None,
-        third_party_signed: Optional[dict] = None,
+        txn_id: str | None = None,
+        remote_room_hosts: list[str] | None = None,
+        third_party_signed: dict | None = None,
         ratelimit: bool = True,
-        content: Optional[dict] = None,
+        content: dict | None = None,
         new_room: bool = False,
         require_consent: bool = True,
         outlier: bool = False,
-        prev_event_ids: Optional[List[str]] = None,
-        state_event_ids: Optional[List[str]] = None,
-        depth: Optional[int] = None,
-        origin_server_ts: Optional[int] = None,
-    ) -> Tuple[str, int]:
+        prev_event_ids: list[str] | None = None,
+        state_event_ids: list[str] | None = None,
+        depth: int | None = None,
+        origin_server_ts: int | None = None,
+    ) -> tuple[str, int]:
         """Helper for update_membership.
 
         Assumes that the membership linearizer is already held for the room.
@@ -1225,12 +1224,12 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
         self,
         user_id: str,
         room_id: str,
-        remote_room_hosts: List[str],
+        remote_room_hosts: list[str],
         content: JsonDict,
         is_partial_state_room: bool,
         is_host_in_room: bool,
         partial_state_before_join: StateMap[str],
-    ) -> Tuple[bool, List[str]]:
+    ) -> tuple[bool, list[str]]:
         """
         Check whether the server should do a remote join (as opposed to a local
         join) for a user.
@@ -1421,7 +1420,7 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
 
     async def send_membership_event(
         self,
-        requester: Optional[Requester],
+        requester: Requester | None,
         event: EventBase,
         context: EventContext,
         ratelimit: bool = True,
@@ -1566,7 +1565,7 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
 
     async def lookup_room_alias(
         self, room_alias: RoomAlias
-    ) -> Tuple[RoomID, List[str]]:
+    ) -> tuple[RoomID, list[str]]:
         """
         Get the room ID associated with a room alias.
 
@@ -1595,7 +1594,7 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
 
         return RoomID.from_string(room_id), servers
 
-    async def _get_inviter(self, user_id: str, room_id: str) -> Optional[UserID]:
+    async def _get_inviter(self, user_id: str, room_id: str) -> UserID | None:
         invite = await self.store.get_invite_for_local_user_in_room(
             user_id=user_id, room_id=room_id
         )
@@ -1611,11 +1610,11 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
         address: str,
         id_server: str,
         requester: Requester,
-        txn_id: Optional[str],
+        txn_id: str | None,
         id_access_token: str,
-        prev_event_ids: Optional[List[str]] = None,
-        depth: Optional[int] = None,
-    ) -> Tuple[str, int]:
+        prev_event_ids: list[str] | None = None,
+        depth: int | None = None,
+    ) -> tuple[str, int]:
         """Invite a 3PID to a room.
 
         Args:
@@ -1725,11 +1724,11 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
         address: str,
         room_id: str,
         user: UserID,
-        txn_id: Optional[str],
+        txn_id: str | None,
         id_access_token: str,
-        prev_event_ids: Optional[List[str]] = None,
-        depth: Optional[int] = None,
-    ) -> Tuple[EventBase, int]:
+        prev_event_ids: list[str] | None = None,
+        depth: int | None = None,
+    ) -> tuple[EventBase, int]:
         room_state = await self._storage_controllers.state.get_current_state(
             room_id,
             StateFilter.from_types(
@@ -1864,8 +1863,8 @@ class RoomMemberMasterHandler(RoomMemberHandler):
         self.distributor.declare("user_left_room")
 
     async def _is_remote_room_too_complex(
-        self, room_id: str, remote_room_hosts: List[str]
-    ) -> Optional[bool]:
+        self, room_id: str, remote_room_hosts: list[str]
+    ) -> bool | None:
         """
         Check if complexity of a remote room is too great.
 
@@ -1900,11 +1899,11 @@ class RoomMemberMasterHandler(RoomMemberHandler):
     async def _remote_join(
         self,
         requester: Requester,
-        remote_room_hosts: List[str],
+        remote_room_hosts: list[str],
         room_id: str,
         user: UserID,
         content: dict,
-    ) -> Tuple[str, int]:
+    ) -> tuple[str, int]:
         """Implements RoomMemberHandler._remote_join"""
         # filter ourselves out of remote_room_hosts: do_invite_join ignores it
         # and if it is the only entry we'd like to return a 404 rather than a
@@ -1978,10 +1977,10 @@ class RoomMemberMasterHandler(RoomMemberHandler):
     async def remote_reject_invite(
         self,
         invite_event_id: str,
-        txn_id: Optional[str],
+        txn_id: str | None,
         requester: Requester,
         content: JsonDict,
-    ) -> Tuple[str, int]:
+    ) -> tuple[str, int]:
         """
         Rejects an out-of-band invite received from a remote user
 
@@ -2015,10 +2014,10 @@ class RoomMemberMasterHandler(RoomMemberHandler):
     async def remote_rescind_knock(
         self,
         knock_event_id: str,
-        txn_id: Optional[str],
+        txn_id: str | None,
         requester: Requester,
         content: JsonDict,
-    ) -> Tuple[str, int]:
+    ) -> tuple[str, int]:
         """
         Rescinds a local knock made on a remote room
 
@@ -2044,10 +2043,10 @@ class RoomMemberMasterHandler(RoomMemberHandler):
     async def _generate_local_out_of_band_leave(
         self,
         previous_membership_event: EventBase,
-        txn_id: Optional[str],
+        txn_id: str | None,
         requester: Requester,
         content: JsonDict,
-    ) -> Tuple[str, int]:
+    ) -> tuple[str, int]:
         """Generate a local leave event for a room
 
         This can be called after we e.g fail to reject an invite via a remote server.
@@ -2127,11 +2126,11 @@ class RoomMemberMasterHandler(RoomMemberHandler):
     async def remote_knock(
         self,
         requester: Requester,
-        remote_room_hosts: List[str],
+        remote_room_hosts: list[str],
         room_id: str,
         user: UserID,
         content: dict,
-    ) -> Tuple[str, int]:
+    ) -> tuple[str, int]:
         """Sends a knock to a room. Attempts to do so via one remote out of a given list.
 
         Args:
@@ -2181,7 +2180,7 @@ class RoomForgetterHandler(StateDeltasHandler):
         self._room_member_handler = hs.get_room_member_handler()
 
         # The current position in the current_state_delta stream
-        self.pos: Optional[int] = None
+        self.pos: int | None = None
 
         # Guard to ensure we only process deltas one at a time
         self._is_processing = False
@@ -2190,7 +2189,10 @@ class RoomForgetterHandler(StateDeltasHandler):
             self._notifier.add_replication_callback(self.notify_new_event)
 
             # We kick this off to pick up outstanding work from before the last restart.
-            self._clock.call_later(0, self.notify_new_event)
+            self._clock.call_later(
+                0,
+                self.notify_new_event,
+            )
 
     def notify_new_event(self) -> None:
         """Called when there may be more deltas to process"""
@@ -2205,9 +2207,7 @@ class RoomForgetterHandler(StateDeltasHandler):
             finally:
                 self._is_processing = False
 
-        run_as_background_process(
-            "room_forgetter.notify_new_event", self.server_name, process
-        )
+        self._hs.run_as_background_process("room_forgetter.notify_new_event", process)
 
     async def _unsafe_process(self) -> None:
         # If self.pos is None then means we haven't fetched it from DB
@@ -2270,7 +2270,7 @@ class RoomForgetterHandler(StateDeltasHandler):
 
             await self._store.update_room_forgetter_stream_pos(max_pos)
 
-    async def _handle_deltas(self, deltas: List[StateDelta]) -> None:
+    async def _handle_deltas(self, deltas: list[StateDelta]) -> None:
         """Called with the state deltas to process"""
         for delta in deltas:
             if delta.event_type != EventTypes.Member:
@@ -2300,7 +2300,7 @@ class RoomForgetterHandler(StateDeltasHandler):
                         raise
 
 
-def get_users_which_can_issue_invite(auth_events: StateMap[EventBase]) -> List[str]:
+def get_users_which_can_issue_invite(auth_events: StateMap[EventBase]) -> list[str]:
     """
     Return the list of users which can issue invites.
 
@@ -2346,7 +2346,7 @@ def get_users_which_can_issue_invite(auth_events: StateMap[EventBase]) -> List[s
     return result
 
 
-def get_servers_from_users(users: List[str]) -> Set[str]:
+def get_servers_from_users(users: list[str]) -> set[str]:
     """
     Resolve a list of users into their servers.
 
diff --git a/synapse/handlers/room_member_worker.py b/synapse/handlers/room_member_worker.py
index 0616a9864d..b56519ab0a 100644
--- a/synapse/handlers/room_member_worker.py
+++ b/synapse/handlers/room_member_worker.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, List, Optional, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.handlers.room_member import NoKnownServersError, RoomMemberHandler
 from synapse.replication.http.membership import (
@@ -51,11 +51,11 @@ class RoomMemberWorkerHandler(RoomMemberHandler):
     async def _remote_join(
         self,
         requester: Requester,
-        remote_room_hosts: List[str],
+        remote_room_hosts: list[str],
         room_id: str,
         user: UserID,
         content: dict,
-    ) -> Tuple[str, int]:
+    ) -> tuple[str, int]:
         """Implements RoomMemberHandler._remote_join"""
         if len(remote_room_hosts) == 0:
             raise NoKnownServersError()
@@ -73,10 +73,10 @@ class RoomMemberWorkerHandler(RoomMemberHandler):
     async def remote_reject_invite(
         self,
         invite_event_id: str,
-        txn_id: Optional[str],
+        txn_id: str | None,
         requester: Requester,
         content: dict,
-    ) -> Tuple[str, int]:
+    ) -> tuple[str, int]:
         """
         Rejects an out-of-band invite received from a remote user
 
@@ -93,10 +93,10 @@ class RoomMemberWorkerHandler(RoomMemberHandler):
     async def remote_rescind_knock(
         self,
         knock_event_id: str,
-        txn_id: Optional[str],
+        txn_id: str | None,
         requester: Requester,
         content: JsonDict,
-    ) -> Tuple[str, int]:
+    ) -> tuple[str, int]:
         """
         Rescinds a local knock made on a remote room
 
@@ -121,11 +121,11 @@ class RoomMemberWorkerHandler(RoomMemberHandler):
     async def remote_knock(
         self,
         requester: Requester,
-        remote_room_hosts: List[str],
+        remote_room_hosts: list[str],
         room_id: str,
         user: UserID,
         content: dict,
-    ) -> Tuple[str, int]:
+    ) -> tuple[str, int]:
         """Sends a knock to a room.
 
         Implements RoomMemberHandler.remote_knock
diff --git a/synapse/handlers/room_summary.py b/synapse/handlers/room_summary.py
index 838fee6a30..9ec0d33f11 100644
--- a/synapse/handlers/room_summary.py
+++ b/synapse/handlers/room_summary.py
@@ -22,7 +22,7 @@
 import itertools
 import logging
 import re
-from typing import TYPE_CHECKING, Dict, Iterable, List, Optional, Sequence, Set, Tuple
+from typing import TYPE_CHECKING, Iterable, Optional, Sequence
 
 import attr
 
@@ -71,7 +71,7 @@ class _PaginationKey:
     # during a pagination session).
     room_id: str
     suggested_only: bool
-    max_depth: Optional[int]
+    max_depth: int | None
     # The randomly generated token.
     token: str
 
@@ -83,9 +83,9 @@ class _PaginationSession:
     # The time the pagination session was created, in milliseconds.
     creation_time_ms: int
     # The queue of rooms which are still to process.
-    room_queue: List["_RoomQueueEntry"]
+    room_queue: list["_RoomQueueEntry"]
     # A set of rooms which have been processed.
-    processed_rooms: Set[str]
+    processed_rooms: set[str]
 
 
 class RoomSummaryHandler:
@@ -112,14 +112,16 @@ class RoomSummaryHandler:
         # If a user tries to fetch the same page multiple times in quick succession,
         # only process the first attempt and return its result to subsequent requests.
         self._pagination_response_cache: ResponseCache[
-            Tuple[
+            tuple[
                 str,
                 str,
                 bool,
-                Optional[int],
-                Optional[int],
-                Optional[str],
-                Optional[Tuple[str, ...]],
+                bool,
+                bool,
+                int | None,
+                int | None,
+                str | None,
+                tuple[str, ...] | None,
             ]
         ] = ResponseCache(
             clock=hs.get_clock(),
@@ -133,10 +135,12 @@ class RoomSummaryHandler:
         requester: Requester,
         requested_room_id: str,
         suggested_only: bool = False,
-        max_depth: Optional[int] = None,
-        limit: Optional[int] = None,
-        from_token: Optional[str] = None,
-        remote_room_hosts: Optional[Tuple[str, ...]] = None,
+        omit_remote_room_hierarchy: bool = False,
+        admin_skip_room_visibility_check: bool = False,
+        max_depth: int | None = None,
+        limit: int | None = None,
+        from_token: str | None = None,
+        remote_room_hosts: tuple[str, ...] | None = None,
     ) -> JsonDict:
         """
         Implementation of the room hierarchy C-S API.
@@ -146,6 +150,11 @@ class RoomSummaryHandler:
             requested_room_id: The room ID to start the hierarchy at (the "root" room).
             suggested_only: Whether we should only return children with the "suggested"
                 flag set.
+            omit_remote_room_hierarchy: Whether to skip reaching out over
+                federation to get information on rooms which the server
+                is not currently joined to
+            admin_skip_room_visibility_check: Whether to skip checking if the room can
+                be accessed by the requester, used for the admin endpoints.
             max_depth: The maximum depth in the tree to explore, must be a
                 non-negative integer.
 
@@ -173,6 +182,8 @@ class RoomSummaryHandler:
                 requester.user.to_string(),
                 requested_room_id,
                 suggested_only,
+                omit_remote_room_hierarchy,
+                admin_skip_room_visibility_check,
                 max_depth,
                 limit,
                 from_token,
@@ -182,6 +193,8 @@ class RoomSummaryHandler:
             requester.user.to_string(),
             requested_room_id,
             suggested_only,
+            omit_remote_room_hierarchy,
+            admin_skip_room_visibility_check,
             max_depth,
             limit,
             from_token,
@@ -193,10 +206,12 @@ class RoomSummaryHandler:
         requester: str,
         requested_room_id: str,
         suggested_only: bool = False,
-        max_depth: Optional[int] = None,
-        limit: Optional[int] = None,
-        from_token: Optional[str] = None,
-        remote_room_hosts: Optional[Tuple[str, ...]] = None,
+        omit_remote_room_hierarchy: bool = False,
+        admin_skip_room_visibility_check: bool = False,
+        max_depth: int | None = None,
+        limit: int | None = None,
+        from_token: str | None = None,
+        remote_room_hosts: tuple[str, ...] | None = None,
     ) -> JsonDict:
         """See docstring for SpaceSummaryHandler.get_room_hierarchy."""
 
@@ -204,17 +219,18 @@ class RoomSummaryHandler:
         local_room = await self._store.is_host_joined(
             requested_room_id, self._server_name
         )
-        if local_room and not await self._is_local_room_accessible(
-            requested_room_id, requester
-        ):
-            raise UnstableSpecAuthError(
-                403,
-                "User %s not in room %s, and room previews are disabled"
-                % (requester, requested_room_id),
-                errcode=Codes.NOT_JOINED,
-            )
+        if not admin_skip_room_visibility_check:
+            if local_room and not await self._is_local_room_accessible(
+                requested_room_id, requester
+            ):
+                raise UnstableSpecAuthError(
+                    403,
+                    "User %s not in room %s, and room previews are disabled"
+                    % (requester, requested_room_id),
+                    errcode=Codes.NOT_JOINED,
+                )
 
-        if not local_room:
+        if not local_room and not omit_remote_room_hierarchy:
             room_hierarchy = await self._summarize_remote_room_hierarchy(
                 _RoomQueueEntry(requested_room_id, remote_room_hosts or ()),
                 False,
@@ -223,12 +239,13 @@ class RoomSummaryHandler:
             if not root_room_entry or not await self._is_remote_room_accessible(
                 requester, requested_room_id, root_room_entry.room
             ):
-                raise UnstableSpecAuthError(
-                    403,
-                    "User %s not in room %s, and room previews are disabled"
-                    % (requester, requested_room_id),
-                    errcode=Codes.NOT_JOINED,
-                )
+                if not admin_skip_room_visibility_check:
+                    raise UnstableSpecAuthError(
+                        403,
+                        "User %s not in room %s, and room previews are disabled"
+                        % (requester, requested_room_id),
+                        errcode=Codes.NOT_JOINED,
+                    )
 
         # If this is continuing a previous session, pull the persisted data.
         if from_token:
@@ -240,13 +257,18 @@ class RoomSummaryHandler:
             except StoreError:
                 raise SynapseError(400, "Unknown pagination token", Codes.INVALID_PARAM)
 
-            # If the requester, room ID, suggested-only, or max depth were modified
-            # the session is invalid.
+            # If the requester, room ID, suggested-only, max depth,
+            # omit_remote_room_hierarchy, or admin_skip_room_visibility_check
+            # were modified the session is invalid.
             if (
                 requester != pagination_session["requester"]
                 or requested_room_id != pagination_session["room_id"]
                 or suggested_only != pagination_session["suggested_only"]
                 or max_depth != pagination_session["max_depth"]
+                or omit_remote_room_hierarchy
+                != pagination_session["omit_remote_room_hierarchy"]
+                or admin_skip_room_visibility_check
+                != pagination_session["admin_skip_room_visibility_check"]
             ):
                 raise SynapseError(400, "Unknown pagination token", Codes.INVALID_PARAM)
 
@@ -262,7 +284,7 @@ class RoomSummaryHandler:
             # Rooms we have already processed.
             processed_rooms = set()
 
-        rooms_result: List[JsonDict] = []
+        rooms_result: list[JsonDict] = []
 
         # Cap the limit to a server-side maximum.
         if limit is None:
@@ -286,12 +308,12 @@ class RoomSummaryHandler:
             # federation. The rationale for caching these and *maybe* using them
             # is to prefer any information local to the homeserver before trusting
             # data received over federation.
-            children_room_entries: Dict[str, JsonDict] = {}
+            children_room_entries: dict[str, JsonDict] = {}
             # A set of room IDs which are children that did not have information
             # returned over federation and are known to be inaccessible to the
             # current server. We should not reach out over federation to try to
             # summarise these rooms.
-            inaccessible_children: Set[str] = set()
+            inaccessible_children: set[str] = set()
 
             # If the room is known locally, summarise it!
             is_in_room = await self._store.is_host_joined(room_id, self._server_name)
@@ -301,6 +323,7 @@ class RoomSummaryHandler:
                     None,
                     room_id,
                     suggested_only,
+                    admin_skip_room_visibility_check=admin_skip_room_visibility_check,
                 )
 
             # Otherwise, attempt to use information for federation.
@@ -321,7 +344,7 @@ class RoomSummaryHandler:
 
                 # If the above isn't true, attempt to fetch the room
                 # information over federation.
-                else:
+                elif not omit_remote_room_hierarchy:
                     (
                         room_entry,
                         children_room_entries,
@@ -378,6 +401,8 @@ class RoomSummaryHandler:
                     "room_id": requested_room_id,
                     "suggested_only": suggested_only,
                     "max_depth": max_depth,
+                    "omit_remote_room_hierarchy": omit_remote_room_hierarchy,
+                    "admin_skip_room_visibility_check": admin_skip_room_visibility_check,
                     # The stored state.
                     "room_queue": [
                         attr.astuple(room_entry) for room_entry in room_queue
@@ -418,8 +443,8 @@ class RoomSummaryHandler:
             # Room is inaccessible to the requesting server.
             raise SynapseError(404, "Unknown room: %s" % (requested_room_id,))
 
-        children_rooms_result: List[JsonDict] = []
-        inaccessible_children: List[str] = []
+        children_rooms_result: list[JsonDict] = []
+        inaccessible_children: list[str] = []
 
         # Iterate through each child and potentially add it, but not its children,
         # to the response.
@@ -455,11 +480,12 @@ class RoomSummaryHandler:
 
     async def _summarize_local_room(
         self,
-        requester: Optional[str],
-        origin: Optional[str],
+        requester: str | None,
+        origin: str | None,
         room_id: str,
         suggested_only: bool,
         include_children: bool = True,
+        admin_skip_room_visibility_check: bool = False,
     ) -> Optional["_RoomEntry"]:
         """
         Generate a room entry and a list of event entries for a given room.
@@ -476,11 +502,16 @@ class RoomSummaryHandler:
                 Otherwise, all children are returned.
             include_children:
                 Whether to include the events of any children.
+            admin_skip_room_visibility_check: Whether to skip checking if the room
+                can be accessed by the requester, used for the admin endpoints.
 
         Returns:
             A room entry if the room should be returned. None, otherwise.
         """
-        if not await self._is_local_room_accessible(room_id, requester, origin):
+        if (
+            not admin_skip_room_visibility_check
+            and not await self._is_local_room_accessible(room_id, requester, origin)
+        ):
             return None
 
         room_entry = await self._build_room_entry(room_id, for_federation=bool(origin))
@@ -496,7 +527,7 @@ class RoomSummaryHandler:
             # we only care about suggested children
             child_events = filter(_is_suggested_child_event, child_events)
 
-        stripped_events: List[JsonDict] = [
+        stripped_events: list[JsonDict] = [
             {
                 "type": e.type,
                 "state_key": e.state_key,
@@ -510,7 +541,7 @@ class RoomSummaryHandler:
 
     async def _summarize_remote_room_hierarchy(
         self, room: "_RoomQueueEntry", suggested_only: bool
-    ) -> Tuple[Optional["_RoomEntry"], Dict[str, JsonDict], Set[str]]:
+    ) -> tuple[Optional["_RoomEntry"], dict[str, JsonDict], set[str]]:
         """
         Request room entries and a list of event entries for a given room by querying a remote server.
 
@@ -563,7 +594,7 @@ class RoomSummaryHandler:
         )
 
     async def _is_local_room_accessible(
-        self, room_id: str, requester: Optional[str], origin: Optional[str] = None
+        self, room_id: str, requester: str | None, origin: str | None = None
     ) -> bool:
         """
         Calculate whether the room should be shown to the requester.
@@ -692,7 +723,7 @@ class RoomSummaryHandler:
         return False
 
     async def _is_remote_room_accessible(
-        self, requester: Optional[str], room_id: str, room: JsonDict
+        self, requester: str | None, room_id: str, room: JsonDict
     ) -> bool:
         """
         Calculate whether the room received over federation should be shown to the requester.
@@ -833,9 +864,9 @@ class RoomSummaryHandler:
 
     async def get_room_summary(
         self,
-        requester: Optional[str],
+        requester: str | None,
         room_id: str,
-        remote_room_hosts: Optional[List[str]] = None,
+        remote_room_hosts: list[str] | None = None,
     ) -> JsonDict:
         """
         Implementation of the room summary C-S API from MSC3266
@@ -934,7 +965,7 @@ class _RoomQueueEntry:
     depth: int = 0
     # The room summary for this room returned via federation. This will only be
     # used if the room is not known locally (and is not a space).
-    remote_room: Optional[JsonDict] = None
+    remote_room: JsonDict | None = None
 
 
 @attr.s(frozen=True, slots=True, auto_attribs=True)
@@ -995,7 +1026,7 @@ _INVALID_ORDER_CHARS_RE = re.compile(r"[^\x20-\x7E]")
 
 def _child_events_comparison_key(
     child: EventBase,
-) -> Tuple[bool, Optional[str], int, str]:
+) -> tuple[bool, str | None, int, str]:
     """
     Generate a value for comparing two child events for ordering.
 
diff --git a/synapse/handlers/saml.py b/synapse/handlers/saml.py
index 81bec7499c..8f2b37c46d 100644
--- a/synapse/handlers/saml.py
+++ b/synapse/handlers/saml.py
@@ -20,7 +20,7 @@
 #
 import logging
 import re
-from typing import TYPE_CHECKING, Callable, Dict, Optional, Set, Tuple
+from typing import TYPE_CHECKING, Callable
 
 import attr
 import saml2
@@ -54,7 +54,7 @@ class Saml2SessionData:
     creation_time: int
     # The user interactive authentication session ID associated with this SAML
     # session (or None if this SAML session is for an initial login).
-    ui_auth_session_id: Optional[str] = None
+    ui_auth_session_id: str | None = None
 
 
 class SamlHandler:
@@ -90,7 +90,7 @@ class SamlHandler:
         self.idp_brand = hs.config.saml2.idp_brand
 
         # a map from saml session id to Saml2SessionData object
-        self._outstanding_requests_dict: Dict[str, Saml2SessionData] = {}
+        self._outstanding_requests_dict: dict[str, Saml2SessionData] = {}
 
         self._sso_handler = hs.get_sso_handler()
         self._sso_handler.register_identity_provider(self)
@@ -98,8 +98,8 @@ class SamlHandler:
     async def handle_redirect_request(
         self,
         request: SynapseRequest,
-        client_redirect_url: Optional[bytes],
-        ui_auth_session_id: Optional[str] = None,
+        client_redirect_url: bytes | None,
+        ui_auth_session_id: str | None = None,
     ) -> str:
         """Handle an incoming request to /login/sso/redirect
 
@@ -303,7 +303,7 @@ class SamlHandler:
                 emails=result.get("emails", []),
             )
 
-        async def grandfather_existing_users() -> Optional[str]:
+        async def grandfather_existing_users() -> str | None:
             # backwards-compatibility hack: see if there is an existing user with a
             # suitable mapping from the uid
             if (
@@ -341,7 +341,7 @@ class SamlHandler:
     def _remote_id_from_saml_response(
         self,
         saml2_auth: saml2.response.AuthnResponse,
-        client_redirect_url: Optional[str],
+        client_redirect_url: str | None,
     ) -> str:
         """Extract the unique remote id from a SAML2 AuthnResponse
 
@@ -393,7 +393,7 @@ def dot_replace_for_mxid(username: str) -> str:
     return username
 
 
-MXID_MAPPER_MAP: Dict[str, Callable[[str], str]] = {
+MXID_MAPPER_MAP: dict[str, Callable[[str], str]] = {
     "hexencode": map_username_to_mxid_localpart,
     "dotreplace": dot_replace_for_mxid,
 }
@@ -509,7 +509,7 @@ class DefaultSamlMappingProvider:
         return SamlConfig(mxid_source_attribute, mxid_mapper)
 
     @staticmethod
-    def get_saml_attributes(config: SamlConfig) -> Tuple[Set[str], Set[str]]:
+    def get_saml_attributes(config: SamlConfig) -> tuple[set[str], set[str]]:
         """Returns the required attributes of a SAML
 
         Args:
diff --git a/synapse/handlers/search.py b/synapse/handlers/search.py
index 1a71135d5f..20b38427a6 100644
--- a/synapse/handlers/search.py
+++ b/synapse/handlers/search.py
@@ -21,7 +21,7 @@
 
 import itertools
 import logging
-from typing import TYPE_CHECKING, Dict, Iterable, List, Optional, Set, Tuple
+from typing import TYPE_CHECKING, Iterable
 
 import attr
 from unpaddedbase64 import decode_base64, encode_base64
@@ -46,13 +46,13 @@ class _SearchResult:
     # The count of results.
     count: int
     # A mapping of event ID to the rank of that event.
-    rank_map: Dict[str, int]
+    rank_map: dict[str, int]
     # A list of the resulting events.
-    allowed_events: List[EventBase]
+    allowed_events: list[EventBase]
     # A map of room ID to results.
-    room_groups: Dict[str, JsonDict]
+    room_groups: dict[str, JsonDict]
     # A set of event IDs to highlight.
-    highlights: Set[str]
+    highlights: set[str]
 
 
 class SearchHandler:
@@ -117,7 +117,7 @@ class SearchHandler:
         return historical_room_ids
 
     async def search(
-        self, requester: Requester, content: JsonDict, batch: Optional[str] = None
+        self, requester: Requester, content: JsonDict, batch: str | None = None
     ) -> JsonDict:
         """Performs a full text search for a user.
 
@@ -226,18 +226,18 @@ class SearchHandler:
     async def _search(
         self,
         requester: Requester,
-        batch_group: Optional[str],
-        batch_group_key: Optional[str],
-        batch_token: Optional[str],
+        batch_group: str | None,
+        batch_group_key: str | None,
+        batch_token: str | None,
         search_term: str,
-        keys: List[str],
+        keys: list[str],
         filter_dict: JsonDict,
         order_by: str,
         include_state: bool,
-        group_keys: List[str],
-        event_context: Optional[bool],
-        before_limit: Optional[int],
-        after_limit: Optional[int],
+        group_keys: list[str],
+        event_context: bool | None,
+        before_limit: int | None,
+        after_limit: int | None,
         include_profile: bool,
     ) -> JsonDict:
         """Performs a full text search for a user.
@@ -286,7 +286,7 @@ class SearchHandler:
         # If doing a subset of all rooms search, check if any of the rooms
         # are from an upgraded room, and search their contents as well
         if search_filter.rooms:
-            historical_room_ids: List[str] = []
+            historical_room_ids: list[str] = []
             for room_id in search_filter.rooms:
                 # Add any previous rooms to the search if they exist
                 ids = await self.get_old_rooms_from_upgraded_room(room_id)
@@ -307,7 +307,7 @@ class SearchHandler:
                 }
             }
 
-        sender_group: Optional[Dict[str, JsonDict]]
+        sender_group: dict[str, JsonDict] | None
 
         if order_by == "rank":
             search_result, sender_group = await self._search_by_rank(
@@ -442,7 +442,7 @@ class SearchHandler:
         search_term: str,
         keys: Iterable[str],
         search_filter: Filter,
-    ) -> Tuple[_SearchResult, Dict[str, JsonDict]]:
+    ) -> tuple[_SearchResult, dict[str, JsonDict]]:
         """
         Performs a full text search for a user ordering by rank.
 
@@ -461,9 +461,9 @@ class SearchHandler:
         """
         rank_map = {}  # event_id -> rank of event
         # Holds result of grouping by room, if applicable
-        room_groups: Dict[str, JsonDict] = {}
+        room_groups: dict[str, JsonDict] = {}
         # Holds result of grouping by sender, if applicable
-        sender_group: Dict[str, JsonDict] = {}
+        sender_group: dict[str, JsonDict] = {}
 
         search_result = await self.store.search_msgs(room_ids, search_term, keys)
 
@@ -517,10 +517,10 @@ class SearchHandler:
         search_term: str,
         keys: Iterable[str],
         search_filter: Filter,
-        batch_group: Optional[str],
-        batch_group_key: Optional[str],
-        batch_token: Optional[str],
-    ) -> Tuple[_SearchResult, Optional[str]]:
+        batch_group: str | None,
+        batch_group_key: str | None,
+        batch_token: str | None,
+    ) -> tuple[_SearchResult, str | None]:
         """
         Performs a full text search for a user ordering by recent.
 
@@ -542,14 +542,14 @@ class SearchHandler:
         """
         rank_map = {}  # event_id -> rank of event
         # Holds result of grouping by room, if applicable
-        room_groups: Dict[str, JsonDict] = {}
+        room_groups: dict[str, JsonDict] = {}
 
         # Holds the next_batch for the entire result set if one of those exists
         global_next_batch = None
 
         highlights = set()
 
-        room_events: List[EventBase] = []
+        room_events: list[EventBase] = []
         i = 0
 
         pagination_token = batch_token
@@ -632,11 +632,11 @@ class SearchHandler:
     async def _calculate_event_contexts(
         self,
         user: UserID,
-        allowed_events: List[EventBase],
+        allowed_events: list[EventBase],
         before_limit: int,
         after_limit: int,
         include_profile: bool,
-    ) -> Dict[str, JsonDict]:
+    ) -> dict[str, JsonDict]:
         """
         Calculates the contextual events for any search results.
 
diff --git a/synapse/handlers/send_email.py b/synapse/handlers/send_email.py
index 6469b182c8..8cdf9c6a87 100644
--- a/synapse/handlers/send_email.py
+++ b/synapse/handlers/send_email.py
@@ -24,7 +24,7 @@ import logging
 from email.mime.multipart import MIMEMultipart
 from email.mime.text import MIMEText
 from io import BytesIO
-from typing import TYPE_CHECKING, Dict, Optional
+from typing import TYPE_CHECKING
 
 from twisted.internet.defer import Deferred
 from twisted.internet.endpoints import HostnameEndpoint
@@ -49,13 +49,13 @@ async def _sendmail(
     from_addr: str,
     to_addr: str,
     msg_bytes: bytes,
-    username: Optional[bytes] = None,
-    password: Optional[bytes] = None,
+    username: bytes | None = None,
+    password: bytes | None = None,
     require_auth: bool = False,
     require_tls: bool = False,
     enable_tls: bool = True,
     force_tls: bool = False,
-    tlsname: Optional[str] = None,
+    tlsname: str | None = None,
 ) -> None:
     """A simple wrapper around ESMTPSenderFactory, to allow substitution in tests
 
@@ -136,7 +136,7 @@ class SendEmailHandler:
         app_name: str,
         html: str,
         text: str,
-        additional_headers: Optional[Dict[str, str]] = None,
+        additional_headers: dict[str, str] | None = None,
     ) -> None:
         """Send a multipart email with the given information.
 
diff --git a/synapse/handlers/set_password.py b/synapse/handlers/set_password.py
index 54116a9b72..042cb4e1b5 100644
--- a/synapse/handlers/set_password.py
+++ b/synapse/handlers/set_password.py
@@ -18,7 +18,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING
 
 from synapse.api.errors import Codes, StoreError, SynapseError
 from synapse.types import Requester
@@ -42,7 +42,7 @@ class SetPasswordHandler:
         user_id: str,
         password_hash: str,
         logout_devices: bool,
-        requester: Optional[Requester] = None,
+        requester: Requester | None = None,
     ) -> None:
         if not self._auth_handler.can_change_password():
             raise SynapseError(403, "Password change disabled", errcode=Codes.FORBIDDEN)
diff --git a/synapse/handlers/sliding_sync/__init__.py b/synapse/handlers/sliding_sync/__init__.py
index 255a041d0e..748f485489 100644
--- a/synapse/handlers/sliding_sync/__init__.py
+++ b/synapse/handlers/sliding_sync/__init__.py
@@ -15,7 +15,7 @@
 import itertools
 import logging
 from itertools import chain
-from typing import TYPE_CHECKING, AbstractSet, Dict, List, Mapping, Optional, Set, Tuple
+from typing import TYPE_CHECKING, AbstractSet, Mapping
 
 from prometheus_client import Histogram
 from typing_extensions import assert_never
@@ -114,9 +114,9 @@ class SlidingSyncHandler:
         self,
         requester: Requester,
         sync_config: SlidingSyncConfig,
-        from_token: Optional[SlidingSyncStreamToken] = None,
+        from_token: SlidingSyncStreamToken | None = None,
         timeout_ms: int = 0,
-    ) -> Tuple[SlidingSyncResult, bool]:
+    ) -> tuple[SlidingSyncResult, bool]:
         """
         Get the sync for a client if we have new data for it now. Otherwise
         wait for new data to arrive on the server. If the timeout expires, then
@@ -201,7 +201,7 @@ class SlidingSyncHandler:
         self,
         sync_config: SlidingSyncConfig,
         to_token: StreamToken,
-        from_token: Optional[SlidingSyncStreamToken] = None,
+        from_token: SlidingSyncStreamToken | None = None,
     ) -> SlidingSyncResult:
         """
         Generates the response body of a Sliding Sync result, represented as a
@@ -262,7 +262,7 @@ class SlidingSyncHandler:
         relevant_rooms_to_send_map = interested_rooms.relevant_rooms_to_send_map
 
         # Fetch room data
-        rooms: Dict[str, SlidingSyncResult.RoomResult] = {}
+        rooms: dict[str, SlidingSyncResult.RoomResult] = {}
 
         new_connection_state = previous_connection_state.get_mutable()
 
@@ -305,6 +305,7 @@ class SlidingSyncHandler:
             # account data, read receipts, typing indicators, to-device messages, etc).
             actual_room_ids=set(relevant_room_map.keys()),
             actual_room_response_map=rooms,
+            room_membership_for_user_at_to_token_map=room_membership_for_user_map,
             from_token=from_token,
             to_token=to_token,
         )
@@ -490,7 +491,7 @@ class SlidingSyncHandler:
         room_membership_for_user_at_to_token: RoomsForUserType,
         from_token: RoomStreamToken,
         to_token: RoomStreamToken,
-    ) -> List[StateDelta]:
+    ) -> list[StateDelta]:
         """
         Get the state deltas between two tokens taking into account the user's
         membership. If the user is LEAVE/BAN, we will only get the state deltas up to
@@ -550,7 +551,7 @@ class SlidingSyncHandler:
         room_id: str,
         room_sync_config: RoomSyncConfig,
         room_membership_for_user_at_to_token: RoomsForUserType,
-        from_token: Optional[SlidingSyncStreamToken],
+        from_token: SlidingSyncStreamToken | None,
         to_token: StreamToken,
         newly_joined: bool,
         newly_left: bool,
@@ -677,11 +678,11 @@ class SlidingSyncHandler:
         # membership. Currently, we have to make all of these optional because
         # `invite`/`knock` rooms only have `stripped_state`. See
         # https://github.com/matrix-org/matrix-spec-proposals/pull/3575#discussion_r1653045932
-        timeline_events: List[EventBase] = []
-        bundled_aggregations: Optional[Dict[str, BundledAggregations]] = None
-        limited: Optional[bool] = None
-        prev_batch_token: Optional[StreamToken] = None
-        num_live: Optional[int] = None
+        timeline_events: list[EventBase] = []
+        bundled_aggregations: dict[str, BundledAggregations] | None = None
+        limited: bool | None = None
+        prev_batch_token: StreamToken | None = None
+        num_live: int | None = None
         if (
             room_sync_config.timeline_limit > 0
             # No timeline for invite/knock rooms (just `stripped_state`)
@@ -813,7 +814,7 @@ class SlidingSyncHandler:
 
         # Figure out any stripped state events for invite/knocks. This allows the
         # potential joiner to identify the room.
-        stripped_state: List[JsonDict] = []
+        stripped_state: list[JsonDict] = []
         if room_membership_for_user_at_to_token.membership in (
             Membership.INVITE,
             Membership.KNOCK,
@@ -850,7 +851,7 @@ class SlidingSyncHandler:
         # For incremental syncs, we can do this first to determine if something relevant
         # has changed and strategically avoid fetching other costly things.
         room_state_delta_id_map: MutableStateMap[str] = {}
-        name_event_id: Optional[str] = None
+        name_event_id: str | None = None
         membership_changed = False
         name_changed = False
         avatar_changed = False
@@ -914,7 +915,7 @@ class SlidingSyncHandler:
         # We only need the room summary for calculating heroes, however if we do
         # fetch it then we can use it to calculate `joined_count` and
         # `invited_count`.
-        room_membership_summary: Optional[Mapping[str, MemberSummary]] = None
+        room_membership_summary: Mapping[str, MemberSummary] | None = None
 
         # `heroes` are required if the room name is not set.
         #
@@ -924,7 +925,7 @@ class SlidingSyncHandler:
         # see https://github.com/matrix-org/matrix-spec/issues/380. This means that
         # clients won't be able to calculate the room name when necessary and just a
         # pitfall we have to deal with until that spec issue is resolved.
-        hero_user_ids: List[str] = []
+        hero_user_ids: list[str] = []
         # TODO: Should we also check for `EventTypes.CanonicalAlias`
         # (`m.room.canonical_alias`) as a fallback for the room name? see
         # https://github.com/matrix-org/matrix-spec-proposals/pull/3575#discussion_r1671260153
@@ -950,8 +951,8 @@ class SlidingSyncHandler:
         #
         # Similarly to other metadata, we only need to calculate the member
         # counts if this is an initial sync or the memberships have changed.
-        joined_count: Optional[int] = None
-        invited_count: Optional[int] = None
+        joined_count: int | None = None
+        invited_count: int | None = None
         if (
             initial or membership_changed
         ) and room_membership_for_user_at_to_token.membership == Membership.JOIN:
@@ -1036,7 +1037,7 @@ class SlidingSyncHandler:
                 )
                 required_state_filter = StateFilter.all()
             else:
-                required_state_types: List[Tuple[str, Optional[str]]] = []
+                required_state_types: list[tuple[str, str | None]] = []
                 num_wild_state_keys = 0
                 lazy_load_room_members = False
                 num_others = 0
@@ -1057,7 +1058,7 @@ class SlidingSyncHandler:
                             lazy_load_room_members = True
 
                             # Everyone in the timeline is relevant
-                            timeline_membership: Set[str] = set()
+                            timeline_membership: set[str] = set()
                             if timeline_events is not None:
                                 for timeline_event in timeline_events:
                                     # Anyone who sent a message is relevant
@@ -1146,7 +1147,7 @@ class SlidingSyncHandler:
 
         # The required state map to store in the room sync config, if it has
         # changed.
-        changed_required_state_map: Optional[Mapping[str, AbstractSet[str]]] = None
+        changed_required_state_map: Mapping[str, AbstractSet[str]] | None = None
 
         # We can return all of the state that was requested if this was the first
         # time we've sent the room down this connection.
@@ -1205,7 +1206,7 @@ class SlidingSyncHandler:
             required_room_state = required_state_filter.filter_state(room_state)
 
         # Find the room name and avatar from the state
-        room_name: Optional[str] = None
+        room_name: str | None = None
         # TODO: Should we also check for `EventTypes.CanonicalAlias`
         # (`m.room.canonical_alias`) as a fallback for the room name? see
         # https://github.com/matrix-org/matrix-spec-proposals/pull/3575#discussion_r1671260153
@@ -1213,13 +1214,13 @@ class SlidingSyncHandler:
         if name_event is not None:
             room_name = name_event.content.get("name")
 
-        room_avatar: Optional[str] = None
+        room_avatar: str | None = None
         avatar_event = room_state.get((EventTypes.RoomAvatar, ""))
         if avatar_event is not None:
             room_avatar = avatar_event.content.get("url")
 
         # Assemble heroes: extract the info from the state we just fetched
-        heroes: List[SlidingSyncResult.RoomResult.StrippedHero] = []
+        heroes: list[SlidingSyncResult.RoomResult.StrippedHero] = []
         for hero_user_id in hero_user_ids:
             member_event = room_state.get((EventTypes.Member, hero_user_id))
             if member_event is not None:
@@ -1374,9 +1375,9 @@ class SlidingSyncHandler:
         self,
         room_id: str,
         to_token: StreamToken,
-        timeline: List[EventBase],
+        timeline: list[EventBase],
         check_outside_timeline: bool,
-    ) -> Optional[int]:
+    ) -> int | None:
         """Get a bump stamp for the room, if we have a bump event and it has
         changed.
 
@@ -1479,7 +1480,7 @@ def _required_state_changes(
     prev_required_state_map: Mapping[str, AbstractSet[str]],
     request_required_state_map: Mapping[str, AbstractSet[str]],
     state_deltas: StateMap[str],
-) -> Tuple[Optional[Mapping[str, AbstractSet[str]]], StateFilter]:
+) -> tuple[Mapping[str, AbstractSet[str]] | None, StateFilter]:
     """Calculates the changes between the required state room config from the
     previous requests compared with the current request.
 
@@ -1524,15 +1525,15 @@ def _required_state_changes(
 
     # Contains updates to the required state map compared with the previous room
     # config. This has the same format as `RoomSyncConfig.required_state`
-    changes: Dict[str, AbstractSet[str]] = {}
+    changes: dict[str, AbstractSet[str]] = {}
 
     # The set of types/state keys that we need to fetch and return to the
     # client. Passed to `StateFilter.from_types(...)`
-    added: List[Tuple[str, Optional[str]]] = []
+    added: list[tuple[str, str | None]] = []
 
     # Convert the list of state deltas to map from type to state_keys that have
     # changed.
-    changed_types_to_state_keys: Dict[str, Set[str]] = {}
+    changed_types_to_state_keys: dict[str, set[str]] = {}
     for event_type, state_key in state_deltas:
         changed_types_to_state_keys.setdefault(event_type, set()).add(state_key)
 
diff --git a/synapse/handlers/sliding_sync/extensions.py b/synapse/handlers/sliding_sync/extensions.py
index 2c39838fa8..828587adf5 100644
--- a/synapse/handlers/sliding_sync/extensions.py
+++ b/synapse/handlers/sliding_sync/extensions.py
@@ -18,28 +18,36 @@ from typing import (
     TYPE_CHECKING,
     AbstractSet,
     ChainMap,
-    Dict,
     Mapping,
     MutableMapping,
-    Optional,
     Sequence,
-    Set,
-    Tuple,
     cast,
 )
 
 from typing_extensions import TypeAlias, assert_never
 
-from synapse.api.constants import AccountDataTypes, EduTypes, RelationTypes
+from synapse.api.constants import (
+    AccountDataTypes,
+    EduTypes,
+    EventContentFields,
+    Membership,
+    MRelatesToFields,
+    RelationTypes,
+)
+from synapse.events import EventBase
 from synapse.handlers.receipts import ReceiptEventSource
+from synapse.handlers.sliding_sync.room_lists import RoomsForUserType
 from synapse.logging.opentracing import trace
 from synapse.storage.databases.main.receipts import ReceiptInRoom
+from synapse.storage.databases.main.relations import ThreadUpdateInfo
 from synapse.types import (
     DeviceListUpdates,
     JsonMapping,
     MultiWriterStreamToken,
+    RoomStreamToken,
     SlidingSyncStreamToken,
     StrCollection,
+    StreamKeyType,
     StreamToken,
     ThreadSubscriptionsToken,
 )
@@ -79,6 +87,7 @@ class SlidingSyncExtensionHandler:
         self.device_handler = hs.get_device_handler()
         self.push_rules_handler = hs.get_push_rules_handler()
         self.relations_handler = hs.get_relations_handler()
+        self._storage_controllers = hs.get_storage_controllers()
         self._enable_thread_subscriptions = hs.config.experimental.msc4306_enabled
         self._enable_threads_ext = hs.config.experimental.msc4360_enabled
 
@@ -89,10 +98,11 @@ class SlidingSyncExtensionHandler:
         previous_connection_state: "PerConnectionState",
         new_connection_state: "MutablePerConnectionState",
         actual_lists: Mapping[str, SlidingSyncResult.SlidingWindowList],
-        actual_room_ids: Set[str],
+        actual_room_ids: set[str],
         actual_room_response_map: Mapping[str, SlidingSyncResult.RoomResult],
+        room_membership_for_user_at_to_token_map: Mapping[str, RoomsForUserType],
         to_token: StreamToken,
-        from_token: Optional[SlidingSyncStreamToken],
+        from_token: SlidingSyncStreamToken | None,
     ) -> SlidingSyncResult.Extensions:
         """Handle extension requests.
 
@@ -106,6 +116,8 @@ class SlidingSyncExtensionHandler:
             actual_room_ids: The actual room IDs in the the Sliding Sync response.
             actual_room_response_map: A map of room ID to room results in the the
                 Sliding Sync response.
+            room_membership_for_user_at_to_token_map: A map of room ID to the membership
+                information for the user in the room at the time of `to_token`.
             to_token: The latest point in the stream to sync up to.
             from_token: The point in the stream to sync from.
         """
@@ -186,7 +198,9 @@ class SlidingSyncExtensionHandler:
             threads_coro = self.get_threads_extension_response(
                 sync_config=sync_config,
                 threads_request=sync_config.extensions.threads,
+                actual_room_ids=actual_room_ids,
                 actual_room_response_map=actual_room_response_map,
+                room_membership_for_user_at_to_token_map=room_membership_for_user_at_to_token_map,
                 to_token=to_token,
                 from_token=from_token,
             )
@@ -221,11 +235,11 @@ class SlidingSyncExtensionHandler:
 
     def find_relevant_room_ids_for_extension(
         self,
-        requested_lists: Optional[StrCollection],
-        requested_room_ids: Optional[StrCollection],
+        requested_lists: StrCollection | None,
+        requested_room_ids: StrCollection | None,
         actual_lists: Mapping[str, SlidingSyncResult.SlidingWindowList],
         actual_room_ids: AbstractSet[str],
-    ) -> Set[str]:
+    ) -> set[str]:
         """
         Handle the reserved `lists`/`rooms` keys for extensions. Extensions should only
         return results for rooms in the Sliding Sync response. This matches up the
@@ -248,7 +262,7 @@ class SlidingSyncExtensionHandler:
 
         # We only want to include account data for rooms that are already in the sliding
         # sync response AND that were requested in the account data request.
-        relevant_room_ids: Set[str] = set()
+        relevant_room_ids: set[str] = set()
 
         # See what rooms from the room subscriptions we should get account data for
         if requested_room_ids is not None:
@@ -265,7 +279,7 @@ class SlidingSyncExtensionHandler:
         if requested_lists is not None:
             for list_key in requested_lists:
                 # Just some typing because we share the variable name in multiple places
-                actual_list: Optional[SlidingSyncResult.SlidingWindowList] = None
+                actual_list: SlidingSyncResult.SlidingWindowList | None = None
 
                 # A wildcard means we process rooms from all lists
                 if list_key == "*":
@@ -296,7 +310,7 @@ class SlidingSyncExtensionHandler:
         sync_config: SlidingSyncConfig,
         to_device_request: SlidingSyncConfig.Extensions.ToDeviceExtension,
         to_token: StreamToken,
-    ) -> Optional[SlidingSyncResult.Extensions.ToDeviceExtension]:
+    ) -> SlidingSyncResult.Extensions.ToDeviceExtension | None:
         """Handle to-device extension (MSC3885)
 
         Args:
@@ -371,8 +385,8 @@ class SlidingSyncExtensionHandler:
         sync_config: SlidingSyncConfig,
         e2ee_request: SlidingSyncConfig.Extensions.E2eeExtension,
         to_token: StreamToken,
-        from_token: Optional[SlidingSyncStreamToken],
-    ) -> Optional[SlidingSyncResult.Extensions.E2eeExtension]:
+        from_token: SlidingSyncStreamToken | None,
+    ) -> SlidingSyncResult.Extensions.E2eeExtension | None:
         """Handle E2EE device extension (MSC3884)
 
         Args:
@@ -388,7 +402,7 @@ class SlidingSyncExtensionHandler:
         if not e2ee_request.enabled:
             return None
 
-        device_list_updates: Optional[DeviceListUpdates] = None
+        device_list_updates: DeviceListUpdates | None = None
         if from_token is not None:
             # TODO: This should take into account the `from_token` and `to_token`
             device_list_updates = await self.device_handler.get_user_ids_changed(
@@ -423,11 +437,11 @@ class SlidingSyncExtensionHandler:
         previous_connection_state: "PerConnectionState",
         new_connection_state: "MutablePerConnectionState",
         actual_lists: Mapping[str, SlidingSyncResult.SlidingWindowList],
-        actual_room_ids: Set[str],
+        actual_room_ids: set[str],
         account_data_request: SlidingSyncConfig.Extensions.AccountDataExtension,
         to_token: StreamToken,
-        from_token: Optional[SlidingSyncStreamToken],
-    ) -> Optional[SlidingSyncResult.Extensions.AccountDataExtension]:
+        from_token: SlidingSyncStreamToken | None,
+    ) -> SlidingSyncResult.Extensions.AccountDataExtension | None:
         """Handle Account Data extension (MSC3959)
 
         Args:
@@ -498,7 +512,7 @@ class SlidingSyncExtensionHandler:
             # down account data previously or not, so we split the relevant
             # rooms up into different collections based on status.
             live_rooms = set()
-            previously_rooms: Dict[str, int] = {}
+            previously_rooms: dict[str, int] = {}
             initial_rooms = set()
 
             for room_id in relevant_room_ids:
@@ -655,12 +669,12 @@ class SlidingSyncExtensionHandler:
         previous_connection_state: "PerConnectionState",
         new_connection_state: "MutablePerConnectionState",
         actual_lists: Mapping[str, SlidingSyncResult.SlidingWindowList],
-        actual_room_ids: Set[str],
+        actual_room_ids: set[str],
         actual_room_response_map: Mapping[str, SlidingSyncResult.RoomResult],
         receipts_request: SlidingSyncConfig.Extensions.ReceiptsExtension,
         to_token: StreamToken,
-        from_token: Optional[SlidingSyncStreamToken],
-    ) -> Optional[SlidingSyncResult.Extensions.ReceiptsExtension]:
+        from_token: SlidingSyncStreamToken | None,
+    ) -> SlidingSyncResult.Extensions.ReceiptsExtension | None:
         """Handle Receipts extension (MSC3960)
 
         Args:
@@ -688,13 +702,13 @@ class SlidingSyncExtensionHandler:
             actual_room_ids=actual_room_ids,
         )
 
-        room_id_to_receipt_map: Dict[str, JsonMapping] = {}
+        room_id_to_receipt_map: dict[str, JsonMapping] = {}
         if len(relevant_room_ids) > 0:
             # We need to handle the different cases depending on if we have sent
             # down receipts previously or not, so we split the relevant rooms
             # up into different collections based on status.
             live_rooms = set()
-            previously_rooms: Dict[str, MultiWriterStreamToken] = {}
+            previously_rooms: dict[str, MultiWriterStreamToken] = {}
             initial_rooms = set()
 
             for room_id in relevant_room_ids:
@@ -859,12 +873,12 @@ class SlidingSyncExtensionHandler:
         self,
         sync_config: SlidingSyncConfig,
         actual_lists: Mapping[str, SlidingSyncResult.SlidingWindowList],
-        actual_room_ids: Set[str],
+        actual_room_ids: set[str],
         actual_room_response_map: Mapping[str, SlidingSyncResult.RoomResult],
         typing_request: SlidingSyncConfig.Extensions.TypingExtension,
         to_token: StreamToken,
-        from_token: Optional[SlidingSyncStreamToken],
-    ) -> Optional[SlidingSyncResult.Extensions.TypingExtension]:
+        from_token: SlidingSyncStreamToken | None,
+    ) -> SlidingSyncResult.Extensions.TypingExtension | None:
         """Handle Typing Notification extension (MSC3961)
 
         Args:
@@ -889,7 +903,7 @@ class SlidingSyncExtensionHandler:
             actual_room_ids=actual_room_ids,
         )
 
-        room_id_to_typing_map: Dict[str, JsonMapping] = {}
+        room_id_to_typing_map: dict[str, JsonMapping] = {}
         if len(relevant_room_ids) > 0:
             # Note: We don't need to take connection tracking into account for typing
             # notifications because they'll get anything still relevant and hasn't timed
@@ -924,8 +938,8 @@ class SlidingSyncExtensionHandler:
         sync_config: SlidingSyncConfig,
         thread_subscriptions_request: SlidingSyncConfig.Extensions.ThreadSubscriptionsExtension,
         to_token: StreamToken,
-        from_token: Optional[SlidingSyncStreamToken],
-    ) -> Optional[SlidingSyncResult.Extensions.ThreadSubscriptionsExtension]:
+        from_token: SlidingSyncStreamToken | None,
+    ) -> SlidingSyncResult.Extensions.ThreadSubscriptionsExtension | None:
         """Handle Thread Subscriptions extension (MSC4308)
 
         Args:
@@ -959,8 +973,8 @@ class SlidingSyncExtensionHandler:
         if len(updates) == 0:
             return None
 
-        subscribed_threads: Dict[str, Dict[str, _ThreadSubscription]] = {}
-        unsubscribed_threads: Dict[str, Dict[str, _ThreadUnsubscription]] = {}
+        subscribed_threads: dict[str, dict[str, _ThreadSubscription]] = {}
+        unsubscribed_threads: dict[str, dict[str, _ThreadUnsubscription]] = {}
         for stream_id, room_id, thread_root_id, subscribed, automatic in updates:
             if subscribed:
                 subscribed_threads.setdefault(room_id, {})[thread_root_id] = (
@@ -988,22 +1002,99 @@ class SlidingSyncExtensionHandler:
             prev_batch=prev_batch,
         )
 
+    def _extract_thread_id_from_event(self, event: EventBase) -> str | None:
+        """Extract thread ID from event if it's a thread reply.
+
+        Args:
+            event: The event to check.
+
+        Returns:
+            The thread ID if the event is a thread reply, None otherwise.
+        """
+        relates_to = event.content.get(EventContentFields.RELATIONS)
+        if isinstance(relates_to, dict):
+            if relates_to.get(MRelatesToFields.REL_TYPE) == RelationTypes.THREAD:
+                return relates_to.get(MRelatesToFields.EVENT_ID)
+        return None
+
+    def _find_threads_in_timeline(
+        self,
+        actual_room_response_map: Mapping[str, SlidingSyncResult.RoomResult],
+    ) -> set[str]:
+        """Find all thread IDs that have events in room timelines.
+
+        Args:
+            actual_room_response_map: A map of room ID to room results.
+
+        Returns:
+            A set of thread IDs (thread root event IDs) that appear in the timeline.
+        """
+        threads_in_timeline: set[str] = set()
+        for room_result in actual_room_response_map.values():
+            if room_result.timeline_events:
+                for event in room_result.timeline_events:
+                    thread_id = self._extract_thread_id_from_event(event)
+                    if thread_id:
+                        threads_in_timeline.add(thread_id)
+        return threads_in_timeline
+
+    def _merge_prev_batch_token(
+        self,
+        current_token: StreamToken | None,
+        new_token: StreamToken | None,
+    ) -> StreamToken | None:
+        """Merge two prev_batch tokens, taking the maximum (latest) for backwards pagination.
+
+        Args:
+            current_token: The current prev_batch token (may be None)
+            new_token: The new prev_batch token to merge (may be None)
+
+        Returns:
+            The merged token (maximum of the two, or None if both are None)
+        """
+        if new_token is None:
+            return current_token
+        if current_token is None:
+            return new_token
+        if new_token.room_key.stream > current_token.room_key.stream:
+            return new_token
+        return current_token
+
+    def _merge_thread_updates(
+        self,
+        target: dict[str, list[ThreadUpdateInfo]],
+        source: dict[str, list[ThreadUpdateInfo]],
+    ) -> None:
+        """Merge thread updates from source into target.
+
+        Args:
+            target: The target dict to merge into (modified in place)
+            source: The source dict to merge from
+        """
+        for thread_id, updates in source.items():
+            target.setdefault(thread_id, []).extend(updates)
+
     async def get_threads_extension_response(
         self,
         sync_config: SlidingSyncConfig,
         threads_request: SlidingSyncConfig.Extensions.ThreadsExtension,
+        actual_room_ids: set[str],
         actual_room_response_map: Mapping[str, SlidingSyncResult.RoomResult],
+        room_membership_for_user_at_to_token_map: Mapping[str, RoomsForUserType],
         to_token: StreamToken,
-        from_token: Optional[SlidingSyncStreamToken],
-    ) -> Optional[SlidingSyncResult.Extensions.ThreadsExtension]:
+        from_token: SlidingSyncStreamToken | None,
+    ) -> SlidingSyncResult.Extensions.ThreadsExtension | None:
         """Handle Threads extension (MSC4360)
 
         Args:
             sync_config: Sync configuration.
             threads_request: The threads extension from the request.
+            actual_room_ids: The actual room IDs in the the Sliding Sync response.
             actual_room_response_map: A map of room ID to room results in the
                 sliding sync response. Used to determine which threads already have
                 events in the room timeline.
+            room_membership_for_user_at_to_token_map: A map of room ID to the membership
+                information for the user in the room at the time of `to_token`.
             to_token: The point in the stream to sync up to.
             from_token: The point in the stream to sync from.
 
@@ -1013,86 +1104,151 @@ class SlidingSyncExtensionHandler:
         if not threads_request.enabled:
             return None
 
-        # Fetch thread updates globally across all joined rooms.
-        # The database layer returns a StreamToken (exclusive) for prev_batch if there
-        # are more results.
-        (
-            all_thread_updates,
-            prev_batch_token,
-        ) = await self.store.get_thread_updates_for_user(
-            user_id=sync_config.user.to_string(),
-            from_token=from_token.stream_token.room_key if from_token else None,
-            to_token=to_token.room_key,
-            limit=threads_request.limit,
-            include_thread_roots=threads_request.include_roots,
-        )
+        # Identify which threads already have events in the room timelines.
+        # If include_roots=False, we'll exclude these threads from the DB query
+        # since the client already sees the thread activity in the timeline.
+        # If include_roots=True, we fetch all threads regardless, because the client
+        # wants the thread root events.
+        threads_to_exclude: set[str] | None = None
+        if not threads_request.include_roots:
+            threads_to_exclude = self._find_threads_in_timeline(
+                actual_room_response_map
+            )
+
+        # Separate rooms into groups based on membership status.
+        # For LEAVE/BAN rooms, we need to bound the to_token to prevent leaking events
+        # that occurred after the user left/was banned.
+        leave_ban_rooms: set[str] = set()
+        other_rooms: set[str] = set()
+
+        for room_id in actual_room_ids:
+            membership_info = room_membership_for_user_at_to_token_map.get(room_id)
+            if membership_info and membership_info.membership in (
+                Membership.LEAVE,
+                Membership.BAN,
+            ):
+                leave_ban_rooms.add(room_id)
+            else:
+                other_rooms.add(room_id)
+
+        # Fetch thread updates, handling LEAVE/BAN rooms separately to avoid data leaks.
+        all_thread_updates: dict[str, list[ThreadUpdateInfo]] = {}
+        prev_batch_token: StreamToken | None = None
+        remaining_limit = threads_request.limit
+
+        # Query for rooms where the user has left or been banned, using their leave/ban
+        # event position as the upper bound to prevent seeing events after they left.
+        if leave_ban_rooms:
+            for room_id in leave_ban_rooms:
+                if remaining_limit <= 0:
+                    # We've already fetched enough updates, but we still need to set
+                    # prev_batch to indicate there are more results.
+                    prev_batch_token = to_token
+                    break
+
+                membership_info = room_membership_for_user_at_to_token_map[room_id]
+                bounded_to_token = membership_info.event_pos.to_room_stream_token()
+
+                (
+                    room_thread_updates,
+                    room_prev_batch,
+                ) = await self.store.get_thread_updates_for_rooms(
+                    room_ids={room_id},
+                    from_token=from_token.stream_token.room_key if from_token else None,
+                    to_token=bounded_to_token,
+                    limit=remaining_limit,
+                    exclude_thread_ids=threads_to_exclude,
+                )
+
+                # Count how many updates we fetched and reduce the remaining limit
+                num_updates = sum(
+                    len(updates) for updates in room_thread_updates.values()
+                )
+                remaining_limit -= num_updates
+
+                self._merge_thread_updates(all_thread_updates, room_thread_updates)
+                prev_batch_token = self._merge_prev_batch_token(
+                    prev_batch_token, room_prev_batch
+                )
+
+        # Query for rooms where the user is joined, invited, or knocking, using the
+        # normal to_token as the upper bound.
+        if other_rooms and remaining_limit > 0:
+            (
+                other_thread_updates,
+                other_prev_batch,
+            ) = await self.store.get_thread_updates_for_rooms(
+                room_ids=other_rooms,
+                from_token=from_token.stream_token.room_key if from_token else None,
+                to_token=to_token.room_key,
+                limit=remaining_limit,
+                exclude_thread_ids=threads_to_exclude,
+            )
+
+            self._merge_thread_updates(all_thread_updates, other_thread_updates)
+            prev_batch_token = self._merge_prev_batch_token(
+                prev_batch_token, other_prev_batch
+            )
 
         if len(all_thread_updates) == 0:
             return None
 
-        # Identify which threads already have events in the room timelines.
-        # If include_roots=False, we'll omit these threads from the extension response
-        # since the client already sees the thread activity in the timeline.
-        # If include_roots=True, we include all threads regardless, because the client
-        # wants the thread root events.
-        threads_in_timeline: Set[Tuple[str, str]] = set()  # (room_id, thread_id)
-        if not threads_request.include_roots:
-            for room_id, room_result in actual_room_response_map.items():
-                if room_result.timeline_events:
-                    for event in room_result.timeline_events:
-                        # Check if this event is part of a thread
-                        relates_to = event.content.get("m.relates_to")
-                        if not isinstance(relates_to, dict):
-                            continue
+        # Filter thread updates for visibility
+        user_id = sync_config.user.to_string()
+        filtered_updates = (
+            await self.relations_handler.process_thread_updates_for_visibility(
+                all_thread_updates, user_id
+            )
+        )
 
-                        rel_type = relates_to.get("rel_type")
+        if not filtered_updates:
+            return None
 
-                        # If this is a thread reply, track the thread
-                        if rel_type == RelationTypes.THREAD:
-                            thread_id = relates_to.get("event_id")
-                            if thread_id:
-                                threads_in_timeline.add((room_id, thread_id))
+        # Note: Updates are already sorted by stream_ordering DESC from the database query,
+        # and filter_events_for_client preserves order, so updates[0] is guaranteed to be
+        # the latest event for each thread.
 
-        # Collect thread root events and get bundled aggregations.
-        # Only fetch bundled aggregations if we have thread root events to attach them to.
-        thread_root_events = [
-            update.thread_root_event
-            for update in all_thread_updates
-            if update.thread_root_event
-        ]
+        # Optionally fetch thread root events and their bundled aggregations
+        thread_root_event_map = {}
         aggregations_map = {}
-        if thread_root_events:
-            aggregations_map = await self.relations_handler.get_bundled_aggregations(
-                thread_root_events,
-                sync_config.user.to_string(),
+        if threads_request.include_roots:
+            (
+                thread_root_event_map,
+                aggregations_map,
+            ) = await self.relations_handler.fetch_thread_roots_and_aggregations(
+                filtered_updates.keys(), user_id
             )
 
-        thread_updates: Dict[str, Dict[str, _ThreadUpdate]] = {}
-        for update in all_thread_updates:
-            # Skip this thread if it already has events in the room timeline
-            # (unless include_roots=True, in which case we always include it)
-            if (update.room_id, update.thread_id) in threads_in_timeline:
-                continue
+        thread_updates: dict[str, dict[str, _ThreadUpdate]] = {}
+        for thread_root, updates in filtered_updates.items():
+            # We only care about the latest update for the thread.
+            # After sorting above, updates[0] is guaranteed to be the latest (highest stream_ordering).
+            latest_update = updates[0]
 
-            # Only look up bundled aggregations if we have a thread root event
-            bundled_aggs = (
-                aggregations_map.get(update.thread_id)
-                if update.thread_root_event
-                else None
-            )
+            # Generate per-thread prev_batch token if this thread has multiple visible updates.
+            # When we hit the global limit, we generate prev_batch tokens for all threads, even if
+            # we only saw 1 update for them. This is to cover the case where we only saw
+            # a single update for a given thread, but the global limit prevents us from
+            # obtaining other updates which would have otherwise been included in the
+            # range.
+            per_thread_prev_batch = None
+            if len(updates) > 1 or prev_batch_token is not None:
+                # Create a token pointing to one position before the latest event's stream position.
+                # This makes it exclusive - /relations with dir=b won't return the latest event again.
+                # Use StreamToken.START as base (all other streams at 0) since only room position matters.
+                per_thread_prev_batch = StreamToken.START.copy_and_replace(
+                    StreamKeyType.ROOM,
+                    RoomStreamToken(stream=latest_update.stream_ordering - 1),
+                )
 
-            thread_updates.setdefault(update.room_id, {})[update.thread_id] = (
+            thread_updates.setdefault(latest_update.room_id, {})[thread_root] = (
                 _ThreadUpdate(
-                    thread_root=update.thread_root_event,
-                    prev_batch=update.prev_batch,
-                    bundled_aggregations=bundled_aggs,
+                    thread_root=thread_root_event_map.get(thread_root),
+                    prev_batch=per_thread_prev_batch,
+                    bundled_aggregations=aggregations_map.get(thread_root),
                 )
             )
 
-        # If after filtering we have no thread updates, return None to omit the extension
-        if not thread_updates:
-            return None
-
         return SlidingSyncResult.Extensions.ThreadsExtension(
             updates=thread_updates,
             prev_batch=prev_batch_token,
diff --git a/synapse/handlers/sliding_sync/room_lists.py b/synapse/handlers/sliding_sync/room_lists.py
index 19116590f7..3d11902236 100644
--- a/synapse/handlers/sliding_sync/room_lists.py
+++ b/synapse/handlers/sliding_sync/room_lists.py
@@ -18,15 +18,9 @@ from itertools import chain
 from typing import (
     TYPE_CHECKING,
     AbstractSet,
-    Dict,
-    List,
     Literal,
     Mapping,
     MutableMapping,
-    Optional,
-    Set,
-    Tuple,
-    Union,
     cast,
 )
 
@@ -85,7 +79,7 @@ logger = logging.getLogger(__name__)
 
 # Helper definition for the types that we might return. We do this to avoid
 # copying data between types (which can be expensive for many rooms).
-RoomsForUserType = Union[RoomsForUserStateReset, RoomsForUser, RoomsForUserSlidingSync]
+RoomsForUserType = RoomsForUserStateReset | RoomsForUser | RoomsForUserSlidingSync
 
 
 @attr.s(auto_attribs=True, slots=True, frozen=True)
@@ -113,7 +107,7 @@ class SlidingSyncInterestedRooms:
     lists: Mapping[str, SlidingSyncResult.SlidingWindowList]
     relevant_room_map: Mapping[str, RoomSyncConfig]
     relevant_rooms_to_send_map: Mapping[str, RoomSyncConfig]
-    all_rooms: Set[str]
+    all_rooms: set[str]
     room_membership_for_user_map: Mapping[str, RoomsForUserType]
 
     newly_joined_rooms: AbstractSet[str]
@@ -188,7 +182,7 @@ class SlidingSyncRoomLists:
         sync_config: SlidingSyncConfig,
         previous_connection_state: "PerConnectionState",
         to_token: StreamToken,
-        from_token: Optional[StreamToken],
+        from_token: StreamToken | None,
     ) -> SlidingSyncInterestedRooms:
         """Fetch the set of rooms that match the request"""
         has_lists = sync_config.lists is not None and len(sync_config.lists) > 0
@@ -225,18 +219,18 @@ class SlidingSyncRoomLists:
         sync_config: SlidingSyncConfig,
         previous_connection_state: "PerConnectionState",
         to_token: StreamToken,
-        from_token: Optional[StreamToken],
+        from_token: StreamToken | None,
     ) -> SlidingSyncInterestedRooms:
         """Implementation of `compute_interested_rooms` using new sliding sync db tables."""
         user_id = sync_config.user.to_string()
 
         # Assemble sliding window lists
-        lists: Dict[str, SlidingSyncResult.SlidingWindowList] = {}
+        lists: dict[str, SlidingSyncResult.SlidingWindowList] = {}
         # Keep track of the rooms that we can display and need to fetch more info about
-        relevant_room_map: Dict[str, RoomSyncConfig] = {}
+        relevant_room_map: dict[str, RoomSyncConfig] = {}
         # The set of room IDs of all rooms that could appear in any list. These
         # include rooms that are outside the list ranges.
-        all_rooms: Set[str] = set()
+        all_rooms: set[str] = set()
 
         # Note: this won't include rooms the user has left themselves. We add back
         # `newly_left` rooms below. This is more efficient than fetching all rooms and
@@ -472,7 +466,7 @@ class SlidingSyncRoomLists:
 
                     all_rooms.update(filtered_sync_room_map)
 
-                    ops: List[SlidingSyncResult.SlidingWindowList.Operation] = []
+                    ops: list[SlidingSyncResult.SlidingWindowList.Operation] = []
 
                     if list_config.ranges:
                         # Optimization: If we are asking for the full range, we don't
@@ -487,7 +481,7 @@ class SlidingSyncRoomLists:
                             and list_config.ranges[0][1]
                             >= len(filtered_sync_room_map) - 1
                         ):
-                            sorted_room_info: List[RoomsForUserType] = list(
+                            sorted_room_info: list[RoomsForUserType] = list(
                                 filtered_sync_room_map.values()
                             )
                         else:
@@ -496,7 +490,7 @@ class SlidingSyncRoomLists:
                                 # Cast is safe because RoomsForUserSlidingSync is part
                                 # of the `RoomsForUserType` union. Why can't it detect this?
                                 cast(
-                                    Dict[str, RoomsForUserType], filtered_sync_room_map
+                                    dict[str, RoomsForUserType], filtered_sync_room_map
                                 ),
                                 to_token,
                                 # We only need to sort the rooms up to the end
@@ -506,7 +500,7 @@ class SlidingSyncRoomLists:
                             )
 
                         for range in list_config.ranges:
-                            room_ids_in_list: List[str] = []
+                            room_ids_in_list: list[str] = []
 
                             # We're going to loop through the sorted list of rooms starting
                             # at the range start index and keep adding rooms until we fill
@@ -624,7 +618,7 @@ class SlidingSyncRoomLists:
         sync_config: SlidingSyncConfig,
         previous_connection_state: "PerConnectionState",
         to_token: StreamToken,
-        from_token: Optional[StreamToken],
+        from_token: StreamToken | None,
     ) -> SlidingSyncInterestedRooms:
         """Fallback code when the database background updates haven't completed yet."""
 
@@ -639,12 +633,12 @@ class SlidingSyncRoomLists:
         dm_room_ids = await self._get_dm_rooms_for_user(sync_config.user.to_string())
 
         # Assemble sliding window lists
-        lists: Dict[str, SlidingSyncResult.SlidingWindowList] = {}
+        lists: dict[str, SlidingSyncResult.SlidingWindowList] = {}
         # Keep track of the rooms that we can display and need to fetch more info about
-        relevant_room_map: Dict[str, RoomSyncConfig] = {}
+        relevant_room_map: dict[str, RoomSyncConfig] = {}
         # The set of room IDs of all rooms that could appear in any list. These
         # include rooms that are outside the list ranges.
-        all_rooms: Set[str] = set()
+        all_rooms: set[str] = set()
 
         if sync_config.lists:
             with start_active_span("assemble_sliding_window_lists"):
@@ -691,10 +685,10 @@ class SlidingSyncRoomLists:
                         filtered_sync_room_map, to_token
                     )
 
-                    ops: List[SlidingSyncResult.SlidingWindowList.Operation] = []
+                    ops: list[SlidingSyncResult.SlidingWindowList.Operation] = []
                     if list_config.ranges:
                         for range in list_config.ranges:
-                            room_ids_in_list: List[str] = []
+                            room_ids_in_list: list[str] = []
 
                             # We're going to loop through the sorted list of rooms starting
                             # at the range start index and keep adding rooms until we fill
@@ -810,15 +804,15 @@ class SlidingSyncRoomLists:
     async def _filter_relevant_rooms_to_send(
         self,
         previous_connection_state: PerConnectionState,
-        from_token: Optional[StreamToken],
-        relevant_room_map: Dict[str, RoomSyncConfig],
-    ) -> Dict[str, RoomSyncConfig]:
+        from_token: StreamToken | None,
+        relevant_room_map: dict[str, RoomSyncConfig],
+    ) -> dict[str, RoomSyncConfig]:
         """Filters the `relevant_room_map` down to those rooms that may have
         updates we need to fetch and return."""
 
         # Filtered subset of `relevant_room_map` for rooms that may have updates
         # (in the event stream)
-        relevant_rooms_to_send_map: Dict[str, RoomSyncConfig] = relevant_room_map
+        relevant_rooms_to_send_map: dict[str, RoomSyncConfig] = relevant_room_map
         if relevant_room_map:
             with start_active_span("filter_relevant_rooms_to_send"):
                 if from_token:
@@ -883,7 +877,7 @@ class SlidingSyncRoomLists:
         user: UserID,
         rooms_for_user: Mapping[str, RoomsForUserType],
         to_token: StreamToken,
-    ) -> Mapping[str, Optional[RoomsForUser]]:
+    ) -> Mapping[str, RoomsForUser | None]:
         """
         Takes the current set of rooms for a user (retrieved after the given
         token), and returns the changes needed to "rewind" it to match the set of
@@ -908,7 +902,7 @@ class SlidingSyncRoomLists:
         #
         # First, we need to get the max stream_ordering of each event persister instance
         # that we queried events from.
-        instance_to_max_stream_ordering_map: Dict[str, int] = {}
+        instance_to_max_stream_ordering_map: dict[str, int] = {}
         for room_for_user in rooms_for_user.values():
             instance_name = room_for_user.event_pos.instance_name
             stream_ordering = room_for_user.event_pos.stream
@@ -966,12 +960,12 @@ class SlidingSyncRoomLists:
 
         # Otherwise we're about to make changes to `rooms_for_user`, so we turn
         # it into a mutable dict.
-        changes: Dict[str, Optional[RoomsForUser]] = {}
+        changes: dict[str, RoomsForUser | None] = {}
 
         # Assemble a list of the first membership event after the `to_token` so we can
         # step backward to the previous membership that would apply to the from/to
         # range.
-        first_membership_change_by_room_id_after_to_token: Dict[
+        first_membership_change_by_room_id_after_to_token: dict[
             str, CurrentStateDeltaMembership
         ] = {}
         for membership_change in current_state_delta_membership_changes_after_to_token:
@@ -1032,8 +1026,8 @@ class SlidingSyncRoomLists:
         self,
         user: UserID,
         to_token: StreamToken,
-        from_token: Optional[StreamToken],
-    ) -> Tuple[Dict[str, RoomsForUserType], AbstractSet[str], AbstractSet[str]]:
+        from_token: StreamToken | None,
+    ) -> tuple[dict[str, RoomsForUserType], AbstractSet[str], AbstractSet[str]]:
         """
         Fetch room IDs that the user has had membership in (the full room list including
         long-lost left rooms that will be filtered, sorted, and sliced).
@@ -1108,7 +1102,7 @@ class SlidingSyncRoomLists:
         # Since we fetched the users room list at some point in time after the
         # tokens, we need to revert/rewind some membership changes to match the point in
         # time of the `to_token`.
-        rooms_for_user: Dict[str, RoomsForUserType] = {
+        rooms_for_user: dict[str, RoomsForUserType] = {
             room.room_id: room for room in room_for_user_list
         }
         changes = await self._get_rewind_changes_to_current_membership_to_token(
@@ -1142,8 +1136,8 @@ class SlidingSyncRoomLists:
         self,
         user_id: str,
         to_token: StreamToken,
-        from_token: Optional[StreamToken],
-    ) -> Tuple[AbstractSet[str], Mapping[str, RoomsForUserStateReset]]:
+        from_token: StreamToken | None,
+    ) -> tuple[AbstractSet[str], Mapping[str, RoomsForUserStateReset]]:
         """Fetch the sets of rooms that the user newly joined or left in the
         given token range.
 
@@ -1163,8 +1157,8 @@ class SlidingSyncRoomLists:
             need to check if a membership still exists in the room.
         """
 
-        newly_joined_room_ids: Set[str] = set()
-        newly_left_room_map: Dict[str, RoomsForUserStateReset] = {}
+        newly_joined_room_ids: set[str] = set()
+        newly_left_room_map: dict[str, RoomsForUserStateReset] = {}
 
         if not from_token:
             return newly_joined_room_ids, newly_left_room_map
@@ -1189,8 +1183,8 @@ class SlidingSyncRoomLists:
         self,
         user_id: str,
         to_token: StreamToken,
-        from_token: Optional[StreamToken],
-    ) -> Tuple[AbstractSet[str], Mapping[str, RoomsForUserStateReset]]:
+        from_token: StreamToken | None,
+    ) -> tuple[AbstractSet[str], Mapping[str, RoomsForUserStateReset]]:
         """Fetch the sets of rooms that the user newly joined or left in the
         given token range.
 
@@ -1209,8 +1203,8 @@ class SlidingSyncRoomLists:
             was state reset out of the room. To actually check for a state reset, you
             need to check if a membership still exists in the room.
         """
-        newly_joined_room_ids: Set[str] = set()
-        newly_left_room_map: Dict[str, RoomsForUserStateReset] = {}
+        newly_joined_room_ids: set[str] = set()
+        newly_left_room_map: dict[str, RoomsForUserStateReset] = {}
 
         # We need to figure out the
         #
@@ -1232,20 +1226,20 @@ class SlidingSyncRoomLists:
         # 1) Assemble a list of the last membership events in some given ranges. Someone
         # could have left and joined multiple times during the given range but we only
         # care about end-result so we grab the last one.
-        last_membership_change_by_room_id_in_from_to_range: Dict[
+        last_membership_change_by_room_id_in_from_to_range: dict[
             str, CurrentStateDeltaMembership
         ] = {}
         # We also want to assemble a list of the first membership events during the token
         # range so we can step backward to the previous membership that would apply to
         # before the token range to see if we have `newly_joined` the room.
-        first_membership_change_by_room_id_in_from_to_range: Dict[
+        first_membership_change_by_room_id_in_from_to_range: dict[
             str, CurrentStateDeltaMembership
         ] = {}
         # Keep track if the room has a non-join event in the token range so we can later
         # tell if it was a `newly_joined` room. If the last membership event in the
         # token range is a join and there is also some non-join in the range, we know
         # they `newly_joined`.
-        has_non_join_event_by_room_id_in_from_to_range: Dict[str, bool] = {}
+        has_non_join_event_by_room_id_in_from_to_range: dict[str, bool] = {}
         for (
             membership_change
         ) in current_state_delta_membership_changes_in_from_to_range:
@@ -1355,9 +1349,9 @@ class SlidingSyncRoomLists:
     async def filter_rooms_relevant_for_sync(
         self,
         user: UserID,
-        room_membership_for_user_map: Dict[str, RoomsForUserType],
+        room_membership_for_user_map: dict[str, RoomsForUserType],
         newly_left_room_ids: AbstractSet[str],
-    ) -> Dict[str, RoomsForUserType]:
+    ) -> dict[str, RoomsForUserType]:
         """
         Filter room IDs that should/can be listed for this user in the sync response (the
         full room list that will be further filtered, sorted, and sliced).
@@ -1402,9 +1396,9 @@ class SlidingSyncRoomLists:
     async def check_room_subscription_allowed_for_user(
         self,
         room_id: str,
-        room_membership_for_user_map: Dict[str, RoomsForUserType],
+        room_membership_for_user_map: dict[str, RoomsForUserType],
         to_token: StreamToken,
-    ) -> Optional[RoomsForUserType]:
+    ) -> RoomsForUserType | None:
         """
         Check whether the user is allowed to see the room based on whether they have
         ever had membership in the room or if the room is `world_readable`.
@@ -1469,8 +1463,8 @@ class SlidingSyncRoomLists:
     async def _bulk_get_stripped_state_for_rooms_from_sync_room_map(
         self,
         room_ids: StrCollection,
-        sync_room_map: Dict[str, RoomsForUserType],
-    ) -> Dict[str, Optional[StateMap[StrippedStateEvent]]]:
+        sync_room_map: dict[str, RoomsForUserType],
+    ) -> dict[str, StateMap[StrippedStateEvent] | None]:
         """
         Fetch stripped state for a list of room IDs. Stripped state is only
         applicable to invite/knock rooms. Other rooms will have `None` as their
@@ -1488,8 +1482,8 @@ class SlidingSyncRoomLists:
             Mapping from room_id to mapping of (type, state_key) to stripped state
             event.
         """
-        room_id_to_stripped_state_map: Dict[
-            str, Optional[StateMap[StrippedStateEvent]]
+        room_id_to_stripped_state_map: dict[
+            str, StateMap[StrippedStateEvent] | None
         ] = {}
 
         # Fetch what we haven't before
@@ -1500,7 +1494,7 @@ class SlidingSyncRoomLists:
         ]
 
         # Gather a list of event IDs we can grab stripped state from
-        invite_or_knock_event_ids: List[str] = []
+        invite_or_knock_event_ids: list[str] = []
         for room_id in room_ids_to_fetch:
             if sync_room_map[room_id].membership in (
                 Membership.INVITE,
@@ -1534,7 +1528,7 @@ class SlidingSyncRoomLists:
                     f"Unexpected membership {membership} (this is a problem with Synapse itself)"
                 )
 
-            stripped_state_map: Optional[MutableStateMap[StrippedStateEvent]] = None
+            stripped_state_map: MutableStateMap[StrippedStateEvent] | None = None
             # Scrutinize unsigned things. `raw_stripped_state_events` should be a list
             # of stripped events
             if raw_stripped_state_events is not None:
@@ -1565,13 +1559,11 @@ class SlidingSyncRoomLists:
             # `content.algorithm` from `EventTypes.RoomEncryption`
             "room_encryption",
         ],
-        room_ids: Set[str],
-        sync_room_map: Dict[str, RoomsForUserType],
+        room_ids: set[str],
+        sync_room_map: dict[str, RoomsForUserType],
         to_token: StreamToken,
-        room_id_to_stripped_state_map: Dict[
-            str, Optional[StateMap[StrippedStateEvent]]
-        ],
-    ) -> Mapping[str, Union[Optional[str], StateSentinel]]:
+        room_id_to_stripped_state_map: dict[str, StateMap[StrippedStateEvent] | None],
+    ) -> Mapping[str, str | None | StateSentinel]:
         """
         Get the given state event content for a list of rooms. First we check the
         current state of the room, then fallback to stripped state if available, then
@@ -1593,7 +1585,7 @@ class SlidingSyncRoomLists:
             the given state event (event_type, ""), otherwise `None`. Rooms unknown to
             this server will return `ROOM_UNKNOWN_SENTINEL`.
         """
-        room_id_to_content: Dict[str, Union[Optional[str], StateSentinel]] = {}
+        room_id_to_content: dict[str, str | None | StateSentinel] = {}
 
         # As a bulk shortcut, use the current state if the server is particpating in the
         # room (meaning we have current state). Ideally, for leave/ban rooms, we would
@@ -1650,7 +1642,7 @@ class SlidingSyncRoomLists:
 
         # Update our `room_id_to_content` map based on the stripped state
         # (applies to invite/knock rooms)
-        rooms_ids_without_stripped_state: Set[str] = set()
+        rooms_ids_without_stripped_state: set[str] = set()
         for room_id in room_ids_without_results:
             stripped_state_map = room_id_to_stripped_state_map.get(
                 room_id, Sentinel.UNSET_SENTINEL
@@ -1730,12 +1722,12 @@ class SlidingSyncRoomLists:
     async def filter_rooms(
         self,
         user: UserID,
-        sync_room_map: Dict[str, RoomsForUserType],
+        sync_room_map: dict[str, RoomsForUserType],
         previous_connection_state: PerConnectionState,
         filters: SlidingSyncConfig.SlidingSyncList.Filters,
         to_token: StreamToken,
         dm_room_ids: AbstractSet[str],
-    ) -> Dict[str, RoomsForUserType]:
+    ) -> dict[str, RoomsForUserType]:
         """
         Filter rooms based on the sync request.
 
@@ -1753,8 +1745,8 @@ class SlidingSyncRoomLists:
         """
         user_id = user.to_string()
 
-        room_id_to_stripped_state_map: Dict[
-            str, Optional[StateMap[StrippedStateEvent]]
+        room_id_to_stripped_state_map: dict[
+            str, StateMap[StrippedStateEvent] | None
         ] = {}
 
         filtered_room_id_set = set(sync_room_map.keys())
@@ -1891,7 +1883,7 @@ class SlidingSyncRoomLists:
             with start_active_span("filters.tags"):
                 # Fetch the user tags for their rooms
                 room_tags = await self.store.get_tags_for_user(user_id)
-                room_id_to_tag_name_set: Dict[str, Set[str]] = {
+                room_id_to_tag_name_set: dict[str, set[str]] = {
                     room_id: set(tags.keys()) for room_id, tags in room_tags.items()
                 }
 
@@ -1947,7 +1939,7 @@ class SlidingSyncRoomLists:
         filters: SlidingSyncConfig.SlidingSyncList.Filters,
         to_token: StreamToken,
         dm_room_ids: AbstractSet[str],
-    ) -> Dict[str, RoomsForUserSlidingSync]:
+    ) -> dict[str, RoomsForUserSlidingSync]:
         """
         Filter rooms based on the sync request.
 
@@ -2059,7 +2051,7 @@ class SlidingSyncRoomLists:
             with start_active_span("filters.tags"):
                 # Fetch the user tags for their rooms
                 room_tags = await self.store.get_tags_for_user(user_id)
-                room_id_to_tag_name_set: Dict[str, Set[str]] = {
+                room_id_to_tag_name_set: dict[str, set[str]] = {
                     room_id: set(tags.keys()) for room_id, tags in room_tags.items()
                 }
 
@@ -2109,10 +2101,10 @@ class SlidingSyncRoomLists:
     @trace
     async def sort_rooms(
         self,
-        sync_room_map: Dict[str, RoomsForUserType],
+        sync_room_map: dict[str, RoomsForUserType],
         to_token: StreamToken,
-        limit: Optional[int] = None,
-    ) -> List[RoomsForUserType]:
+        limit: int | None = None,
+    ) -> list[RoomsForUserType]:
         """
         Sort by `stream_ordering` of the last event that the user should see in the
         room. `stream_ordering` is unique so we get a stable sort.
@@ -2133,11 +2125,11 @@ class SlidingSyncRoomLists:
 
         # Assemble a map of room ID to the `stream_ordering` of the last activity that the
         # user should see in the room (<= `to_token`)
-        last_activity_in_room_map: Dict[str, int] = {}
+        last_activity_in_room_map: dict[str, int] = {}
 
         # Same as above, except for positions that we know are in the event
         # stream cache.
-        cached_positions: Dict[str, int] = {}
+        cached_positions: dict[str, int] = {}
 
         earliest_cache_position = (
             self.store._events_stream_cache.get_earliest_known_position()
diff --git a/synapse/handlers/sliding_sync/store.py b/synapse/handlers/sliding_sync/store.py
index d24fccf76f..7bcd5f27ea 100644
--- a/synapse/handlers/sliding_sync/store.py
+++ b/synapse/handlers/sliding_sync/store.py
@@ -13,7 +13,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING
 
 import attr
 
@@ -66,7 +66,7 @@ class SlidingSyncConnectionStore:
     async def get_and_clear_connection_positions(
         self,
         sync_config: SlidingSyncConfig,
-        from_token: Optional[SlidingSyncStreamToken],
+        from_token: SlidingSyncStreamToken | None,
     ) -> PerConnectionState:
         """Fetch the per-connection state for the token.
 
@@ -93,7 +93,7 @@ class SlidingSyncConnectionStore:
     async def record_new_state(
         self,
         sync_config: SlidingSyncConfig,
-        from_token: Optional[SlidingSyncStreamToken],
+        from_token: SlidingSyncStreamToken | None,
         new_connection_state: MutablePerConnectionState,
     ) -> int:
         """Record updated per-connection state, returning the connection
diff --git a/synapse/handlers/sso.py b/synapse/handlers/sso.py
index eec420cbb1..ebbe7afa84 100644
--- a/synapse/handlers/sso.py
+++ b/synapse/handlers/sso.py
@@ -27,14 +27,10 @@ from typing import (
     Any,
     Awaitable,
     Callable,
-    Dict,
     Iterable,
-    List,
     Mapping,
     NoReturn,
-    Optional,
     Protocol,
-    Set,
 )
 from urllib.parse import urlencode
 
@@ -105,12 +101,12 @@ class SsoIdentityProvider(Protocol):
         """User-facing name for this provider"""
 
     @property
-    def idp_icon(self) -> Optional[str]:
+    def idp_icon(self) -> str | None:
         """Optional MXC URI for user-facing icon"""
         return None
 
     @property
-    def idp_brand(self) -> Optional[str]:
+    def idp_brand(self) -> str | None:
         """Optional branding identifier"""
         return None
 
@@ -118,8 +114,8 @@ class SsoIdentityProvider(Protocol):
     async def handle_redirect_request(
         self,
         request: SynapseRequest,
-        client_redirect_url: Optional[bytes],
-        ui_auth_session_id: Optional[str] = None,
+        client_redirect_url: bytes | None,
+        ui_auth_session_id: str | None = None,
     ) -> str:
         """Handle an incoming request to /login/sso/redirect
 
@@ -144,10 +140,10 @@ class UserAttributes:
     # the localpart of the mxid that the mapper has assigned to the user.
     # if `None`, the mapper has not picked a userid, and the user should be prompted to
     # enter one.
-    localpart: Optional[str]
+    localpart: str | None
     confirm_localpart: bool = False
-    display_name: Optional[str] = None
-    picture: Optional[str] = None
+    display_name: str | None = None
+    picture: str | None = None
     # mypy thinks these are incompatible for some reason.
     emails: StrCollection = attr.Factory(list)
 
@@ -160,19 +156,19 @@ class UsernameMappingSession:
     auth_provider_id: str
 
     # An optional session ID from the IdP.
-    auth_provider_session_id: Optional[str]
+    auth_provider_session_id: str | None
 
     # user ID on the IdP server
     remote_user_id: str
 
     # attributes returned by the ID mapper
-    display_name: Optional[str]
+    display_name: str | None
     emails: StrCollection
-    avatar_url: Optional[str]
+    avatar_url: str | None
 
     # An optional dictionary of extra attributes to be provided to the client in the
     # login response.
-    extra_login_attributes: Optional[JsonDict]
+    extra_login_attributes: JsonDict | None
 
     # where to redirect the client back to
     client_redirect_url: str
@@ -181,11 +177,11 @@ class UsernameMappingSession:
     expiry_time_ms: int
 
     # choices made by the user
-    chosen_localpart: Optional[str] = None
+    chosen_localpart: str | None = None
     use_display_name: bool = True
     use_avatar: bool = True
     emails_to_use: StrCollection = ()
-    terms_accepted_version: Optional[str] = None
+    terms_accepted_version: str | None = None
 
 
 # the HTTP cookie used to track the mapping session id
@@ -224,13 +220,13 @@ class SsoHandler:
         )
 
         # a lock on the mappings
-        self._mapping_lock = Linearizer(name="sso_user_mapping", clock=hs.get_clock())
+        self._mapping_lock = Linearizer(clock=hs.get_clock(), name="sso_user_mapping")
 
         # a map from session id to session data
-        self._username_mapping_sessions: Dict[str, UsernameMappingSession] = {}
+        self._username_mapping_sessions: dict[str, UsernameMappingSession] = {}
 
         # map from idp_id to SsoIdentityProvider
-        self._identity_providers: Dict[str, SsoIdentityProvider] = {}
+        self._identity_providers: dict[str, SsoIdentityProvider] = {}
 
         self._consent_at_registration = hs.config.consent.user_consent_at_registration
 
@@ -281,7 +277,7 @@ class SsoHandler:
         self,
         request: Request,
         error: str,
-        error_description: Optional[str] = None,
+        error_description: str | None = None,
         code: int = 400,
     ) -> None:
         """Renders the error template and responds with it.
@@ -305,7 +301,7 @@ class SsoHandler:
         self,
         request: SynapseRequest,
         client_redirect_url: bytes,
-        idp_id: Optional[str],
+        idp_id: str | None,
     ) -> str:
         """Handle a request to /login/sso/redirect
 
@@ -324,7 +320,7 @@ class SsoHandler:
             )
 
         # if the client chose an IdP, use that
-        idp: Optional[SsoIdentityProvider] = None
+        idp: SsoIdentityProvider | None = None
         if idp_id:
             idp = self._identity_providers.get(idp_id)
             if not idp:
@@ -344,7 +340,7 @@ class SsoHandler:
 
     async def get_sso_user_by_remote_user_id(
         self, auth_provider_id: str, remote_user_id: str
-    ) -> Optional[str]:
+    ) -> str | None:
         """
         Maps the user ID of a remote IdP to a mxid for a previously seen user.
 
@@ -392,9 +388,9 @@ class SsoHandler:
         request: SynapseRequest,
         client_redirect_url: str,
         sso_to_matrix_id_mapper: Callable[[int], Awaitable[UserAttributes]],
-        grandfather_existing_users: Callable[[], Awaitable[Optional[str]]],
-        extra_login_attributes: Optional[JsonDict] = None,
-        auth_provider_session_id: Optional[str] = None,
+        grandfather_existing_users: Callable[[], Awaitable[str | None]],
+        extra_login_attributes: JsonDict | None = None,
+        auth_provider_session_id: str | None = None,
         registration_enabled: bool = True,
     ) -> None:
         """
@@ -585,8 +581,8 @@ class SsoHandler:
 
     def _get_url_for_next_new_user_step(
         self,
-        attributes: Optional[UserAttributes] = None,
-        session: Optional[UsernameMappingSession] = None,
+        attributes: UserAttributes | None = None,
+        session: UsernameMappingSession | None = None,
     ) -> bytes:
         """Returns the URL to redirect to for the next step of new user registration
 
@@ -625,8 +621,8 @@ class SsoHandler:
         attributes: UserAttributes,
         client_redirect_url: str,
         next_step_url: bytes,
-        extra_login_attributes: Optional[JsonDict],
-        auth_provider_session_id: Optional[str],
+        extra_login_attributes: JsonDict | None,
+        auth_provider_session_id: str | None,
     ) -> NoReturn:
         """Creates a UsernameMappingSession and redirects the browser
 
@@ -999,7 +995,7 @@ class SsoHandler:
         session.use_avatar = use_avatar
 
         emails_from_idp = set(session.emails)
-        filtered_emails: Set[str] = set()
+        filtered_emails: set[str] = set()
 
         # we iterate through the list rather than just building a set conjunction, so
         # that we can log attempts to use unknown addresses
@@ -1142,7 +1138,7 @@ class SsoHandler:
     def check_required_attributes(
         self,
         request: SynapseRequest,
-        attributes: Mapping[str, List[Any]],
+        attributes: Mapping[str, list[Any]],
         attribute_requirements: Iterable[SsoAttributeRequirement],
     ) -> bool:
         """
@@ -1178,7 +1174,7 @@ class SsoHandler:
         self,
         auth_provider_id: str,
         auth_provider_session_id: str,
-        expected_user_id: Optional[str] = None,
+        expected_user_id: str | None = None,
     ) -> None:
         """Revoke any devices and in-flight logins tied to a provider session.
 
@@ -1259,7 +1255,7 @@ def get_username_mapping_session_cookie_from_request(request: IRequest) -> str:
 
 
 def _check_attribute_requirement(
-    attributes: Mapping[str, List[Any]], req: SsoAttributeRequirement
+    attributes: Mapping[str, list[Any]], req: SsoAttributeRequirement
 ) -> bool:
     """Check if SSO attributes meet the proper requirements.
 
diff --git a/synapse/handlers/state_deltas.py b/synapse/handlers/state_deltas.py
index 2fbe407a63..db63f0483d 100644
--- a/synapse/handlers/state_deltas.py
+++ b/synapse/handlers/state_deltas.py
@@ -20,7 +20,7 @@
 
 import logging
 from enum import Enum, auto
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING
 
 if TYPE_CHECKING:
     from synapse.server import HomeServer
@@ -40,8 +40,8 @@ class StateDeltasHandler:
 
     async def _get_key_change(
         self,
-        prev_event_id: Optional[str],
-        event_id: Optional[str],
+        prev_event_id: str | None,
+        event_id: str | None,
         key_name: str,
         public_value: str,
     ) -> MatchChange:
diff --git a/synapse/handlers/stats.py b/synapse/handlers/stats.py
index a2602ea818..6d661453ac 100644
--- a/synapse/handlers/stats.py
+++ b/synapse/handlers/stats.py
@@ -25,15 +25,11 @@ from typing import (
     TYPE_CHECKING,
     Any,
     Counter as CounterType,
-    Dict,
     Iterable,
-    Optional,
-    Tuple,
 )
 
 from synapse.api.constants import EventContentFields, EventTypes, Membership
 from synapse.metrics import SERVER_NAME_LABEL, event_processing_positions
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.storage.databases.main.state_deltas import StateDelta
 from synapse.types import JsonDict
 from synapse.util.events import get_plain_text_topic_from_event_content
@@ -65,7 +61,7 @@ class StatsHandler:
         self.stats_enabled = hs.config.stats.stats_enabled
 
         # The current position in the current_state_delta stream
-        self.pos: Optional[int] = None
+        self.pos: int | None = None
 
         # Guard to ensure we only process deltas one at a time
         self._is_processing = False
@@ -75,7 +71,10 @@ class StatsHandler:
 
             # We kick this off so that we don't have to wait for a change before
             # we start populating stats
-            self.clock.call_later(0, self.notify_new_event)
+            self.clock.call_later(
+                0,
+                self.notify_new_event,
+            )
 
     def notify_new_event(self) -> None:
         """Called when there may be more deltas to process"""
@@ -90,7 +89,7 @@ class StatsHandler:
             finally:
                 self._is_processing = False
 
-        run_as_background_process("stats.notify_new_event", self.server_name, process)
+        self.hs.run_as_background_process("stats.notify_new_event", process)
 
     async def _unsafe_process(self) -> None:
         # If self.pos is None then means we haven't fetched it from DB
@@ -155,7 +154,7 @@ class StatsHandler:
 
     async def _handle_deltas(
         self, deltas: Iterable[StateDelta]
-    ) -> Tuple[Dict[str, CounterType[str]], Dict[str, CounterType[str]]]:
+    ) -> tuple[dict[str, CounterType[str]], dict[str, CounterType[str]]]:
         """Called with the state deltas to process
 
         Returns:
@@ -163,10 +162,10 @@ class StatsHandler:
             mapping from room/user ID to changes in the various fields.
         """
 
-        room_to_stats_deltas: Dict[str, CounterType[str]] = {}
-        user_to_stats_deltas: Dict[str, CounterType[str]] = {}
+        room_to_stats_deltas: dict[str, CounterType[str]] = {}
+        user_to_stats_deltas: dict[str, CounterType[str]] = {}
 
-        room_to_state_updates: Dict[str, Dict[str, Any]] = {}
+        room_to_state_updates: dict[str, dict[str, Any]] = {}
 
         for delta in deltas:
             logger.debug(
diff --git a/synapse/handlers/sync.py b/synapse/handlers/sync.py
index c0341c5654..b534e24698 100644
--- a/synapse/handlers/sync.py
+++ b/synapse/handlers/sync.py
@@ -24,14 +24,8 @@ from typing import (
     TYPE_CHECKING,
     AbstractSet,
     Any,
-    Dict,
-    FrozenSet,
-    List,
     Mapping,
-    Optional,
     Sequence,
-    Set,
-    Tuple,
 )
 
 import attr
@@ -113,7 +107,7 @@ LAZY_LOADED_MEMBERS_CACHE_MAX_AGE = 30 * 60 * 1000
 LAZY_LOADED_MEMBERS_CACHE_MAX_SIZE = 100
 
 
-SyncRequestKey = Tuple[Any, ...]
+SyncRequestKey = tuple[Any, ...]
 
 
 @attr.s(slots=True, frozen=True, auto_attribs=True)
@@ -121,7 +115,7 @@ class SyncConfig:
     user: UserID
     filter_collection: FilterCollection
     is_guest: bool
-    device_id: Optional[str]
+    device_id: str | None
     use_state_after: bool
 
 
@@ -132,7 +126,7 @@ class TimelineBatch:
     limited: bool
     # A mapping of event ID to the bundled aggregations for the above events.
     # This is only calculated if limited is true.
-    bundled_aggregations: Optional[Dict[str, BundledAggregations]] = None
+    bundled_aggregations: dict[str, BundledAggregations] | None = None
 
     def __bool__(self) -> bool:
         """Make the result appear empty if there are no updates. This is used
@@ -151,11 +145,11 @@ class JoinedSyncResult:
     room_id: str
     timeline: TimelineBatch
     state: StateMap[EventBase]
-    ephemeral: List[JsonDict]
-    account_data: List[JsonDict]
+    ephemeral: list[JsonDict]
+    account_data: list[JsonDict]
     unread_notifications: JsonDict
     unread_thread_notifications: JsonDict
-    summary: Optional[JsonDict]
+    summary: JsonDict | None
     unread_count: int
 
     def __bool__(self) -> bool:
@@ -174,7 +168,7 @@ class ArchivedSyncResult:
     room_id: str
     timeline: TimelineBatch
     state: StateMap[EventBase]
-    account_data: List[JsonDict]
+    account_data: list[JsonDict]
 
     def __bool__(self) -> bool:
         """Make the result appear empty if there are no updates. This is used
@@ -209,11 +203,11 @@ class _RoomChanges:
     and left room IDs since last sync.
     """
 
-    room_entries: List["RoomSyncResultBuilder"]
-    invited: List[InvitedSyncResult]
-    knocked: List[KnockedSyncResult]
-    newly_joined_rooms: List[str]
-    newly_left_rooms: List[str]
+    room_entries: list["RoomSyncResultBuilder"]
+    invited: list[InvitedSyncResult]
+    knocked: list[KnockedSyncResult]
+    newly_joined_rooms: list[str]
+    newly_left_rooms: list[str]
 
 
 @attr.s(slots=True, frozen=True, auto_attribs=True)
@@ -236,16 +230,16 @@ class SyncResult:
     """
 
     next_batch: StreamToken
-    presence: List[UserPresenceState]
-    account_data: List[JsonDict]
-    joined: List[JoinedSyncResult]
-    invited: List[InvitedSyncResult]
-    knocked: List[KnockedSyncResult]
-    archived: List[ArchivedSyncResult]
-    to_device: List[JsonDict]
+    presence: list[UserPresenceState]
+    account_data: list[JsonDict]
+    joined: list[JoinedSyncResult]
+    invited: list[InvitedSyncResult]
+    knocked: list[KnockedSyncResult]
+    archived: list[ArchivedSyncResult]
+    to_device: list[JsonDict]
     device_lists: DeviceListUpdates
     device_one_time_keys_count: JsonMapping
-    device_unused_fallback_key_types: List[str]
+    device_unused_fallback_key_types: list[str]
 
     def __bool__(self) -> bool:
         """Make the result appear empty if there are no updates. This is used
@@ -267,7 +261,7 @@ class SyncResult:
     def empty(
         next_batch: StreamToken,
         device_one_time_keys_count: JsonMapping,
-        device_unused_fallback_key_types: List[str],
+        device_unused_fallback_key_types: list[str],
     ) -> "SyncResult":
         "Return a new empty result"
         return SyncResult(
@@ -319,10 +313,11 @@ class SyncHandler:
 
         # ExpiringCache((User, Device)) -> LruCache(user_id => event_id)
         self.lazy_loaded_members_cache: ExpiringCache[
-            Tuple[str, Optional[str]], LruCache[str, str]
+            tuple[str, str | None], LruCache[str, str]
         ] = ExpiringCache(
             cache_name="lazy_loaded_members_cache",
             server_name=self.server_name,
+            hs=hs,
             clock=self.clock,
             max_len=0,
             expiry_ms=LAZY_LOADED_MEMBERS_CACHE_MAX_AGE,
@@ -335,7 +330,7 @@ class SyncHandler:
         requester: Requester,
         sync_config: SyncConfig,
         request_key: SyncRequestKey,
-        since_token: Optional[StreamToken] = None,
+        since_token: StreamToken | None = None,
         timeout: int = 0,
         full_state: bool = False,
     ) -> SyncResult:
@@ -376,7 +371,7 @@ class SyncHandler:
     async def _wait_for_sync_for_user(
         self,
         sync_config: SyncConfig,
-        since_token: Optional[StreamToken],
+        since_token: StreamToken | None,
         timeout: int,
         full_state: bool,
         cache_context: ResponseCacheContext[SyncRequestKey],
@@ -418,7 +413,7 @@ class SyncHandler:
                 )
                 device_id = sync_config.device_id
                 one_time_keys_count: JsonMapping = {}
-                unused_fallback_key_types: List[str] = []
+                unused_fallback_key_types: list[str] = []
                 if device_id:
                     user_id = sync_config.user.to_string()
                     # TODO: We should have a way to let clients differentiate between the states of:
@@ -506,7 +501,7 @@ class SyncHandler:
     async def current_sync_for_user(
         self,
         sync_config: SyncConfig,
-        since_token: Optional[StreamToken] = None,
+        since_token: StreamToken | None = None,
         full_state: bool = False,
     ) -> SyncResult:
         """
@@ -541,8 +536,8 @@ class SyncHandler:
         self,
         sync_result_builder: "SyncResultBuilder",
         now_token: StreamToken,
-        since_token: Optional[StreamToken] = None,
-    ) -> Tuple[StreamToken, Dict[str, List[JsonDict]]]:
+        since_token: StreamToken | None = None,
+    ) -> tuple[StreamToken, dict[str, list[JsonDict]]]:
         """Get the ephemeral events for each room the user is in
         Args:
             sync_result_builder
@@ -552,7 +547,7 @@ class SyncHandler:
         Returns:
             A tuple of the now StreamToken, updated to reflect the which typing
             events are included, and a dict mapping from room_id to a list of
-            typing events for that room.
+            ephemeral events for that room.
         """
 
         sync_config = sync_result_builder.sync_config
@@ -577,12 +572,8 @@ class SyncHandler:
             ephemeral_by_room: JsonDict = {}
 
             for event in typing:
-                # we want to exclude the room_id from the event, but modifying the
-                # result returned by the event source is poor form (it might cache
-                # the object)
                 room_id = event["room_id"]
-                event_copy = {k: v for (k, v) in event.items() if k != "room_id"}
-                ephemeral_by_room.setdefault(room_id, []).append(event_copy)
+                ephemeral_by_room.setdefault(room_id, []).append(event)
 
             receipt_key = (
                 since_token.receipt_key
@@ -602,9 +593,7 @@ class SyncHandler:
 
             for event in receipts:
                 room_id = event["room_id"]
-                # exclude room id, as above
-                event_copy = {k: v for (k, v) in event.items() if k != "room_id"}
-                ephemeral_by_room.setdefault(room_id, []).append(event_copy)
+                ephemeral_by_room.setdefault(room_id, []).append(event)
 
         return now_token, ephemeral_by_room
 
@@ -614,8 +603,8 @@ class SyncHandler:
         sync_result_builder: "SyncResultBuilder",
         sync_config: SyncConfig,
         upto_token: StreamToken,
-        since_token: Optional[StreamToken] = None,
-        potential_recents: Optional[List[EventBase]] = None,
+        since_token: StreamToken | None = None,
+        potential_recents: list[EventBase] | None = None,
         newly_joined_room: bool = False,
     ) -> TimelineBatch:
         """Create a timeline batch for the room
@@ -674,7 +663,7 @@ class SyncHandler:
                 # We check if there are any state events, if there are then we pass
                 # all current state events to the filter_events function. This is to
                 # ensure that we always include current state in the timeline
-                current_state_ids: FrozenSet[str] = frozenset()
+                current_state_ids: frozenset[str] = frozenset()
                 if any(e.is_state() for e in recents):
                     # FIXME(faster_joins): We use the partial state here as
                     # we don't want to block `/sync` on finishing a lazy join.
@@ -860,7 +849,7 @@ class SyncHandler:
         batch: TimelineBatch,
         state: MutableStateMap[EventBase],
         now_token: StreamToken,
-    ) -> Optional[JsonDict]:
+    ) -> JsonDict | None:
         """Works out a room summary block for this room, summarising the number
         of joined members in the room, and providing the 'hero' members if the
         room has no name so clients can consistently name rooms.  Also adds
@@ -973,15 +962,14 @@ class SyncHandler:
         return summary
 
     def get_lazy_loaded_members_cache(
-        self, cache_key: Tuple[str, Optional[str]]
+        self, cache_key: tuple[str, str | None]
     ) -> LruCache[str, str]:
-        cache: Optional[LruCache[str, str]] = self.lazy_loaded_members_cache.get(
-            cache_key
-        )
+        cache: LruCache[str, str] | None = self.lazy_loaded_members_cache.get(cache_key)
         if cache is None:
             logger.debug("creating LruCache for %r", cache_key)
             cache = LruCache(
                 max_size=LAZY_LOADED_MEMBERS_CACHE_MAX_SIZE,
+                clock=self.clock,
                 server_name=self.server_name,
             )
             self.lazy_loaded_members_cache[cache_key] = cache
@@ -994,7 +982,7 @@ class SyncHandler:
         room_id: str,
         batch: TimelineBatch,
         sync_config: SyncConfig,
-        since_token: Optional[StreamToken],
+        since_token: StreamToken | None,
         end_token: StreamToken,
         full_state: bool,
         joined: bool,
@@ -1033,11 +1021,11 @@ class SyncHandler:
         ):
             # The memberships needed for events in the timeline.
             # Only calculated when `lazy_load_members` is on.
-            members_to_fetch: Optional[Set[str]] = None
+            members_to_fetch: set[str] | None = None
 
             # A dictionary mapping user IDs to the first event in the timeline sent by
             # them. Only calculated when `lazy_load_members` is on.
-            first_event_by_sender_map: Optional[Dict[str, EventBase]] = None
+            first_event_by_sender_map: dict[str, EventBase] | None = None
 
             # The contribution to the room state from state events in the timeline.
             # Only contains the last event for any given state key.
@@ -1163,7 +1151,7 @@ class SyncHandler:
                     if t[0] == EventTypes.Member:
                         cache.set(t[1], event_id)
 
-        state: Dict[str, EventBase] = {}
+        state: dict[str, EventBase] = {}
         if state_ids:
             state = await self.store.get_events(list(state_ids.values()))
 
@@ -1181,7 +1169,7 @@ class SyncHandler:
         sync_config: SyncConfig,
         batch: TimelineBatch,
         end_token: StreamToken,
-        members_to_fetch: Optional[Set[str]],
+        members_to_fetch: set[str] | None,
         timeline_state: StateMap[str],
         joined: bool,
     ) -> StateMap[str]:
@@ -1331,7 +1319,7 @@ class SyncHandler:
         batch: TimelineBatch,
         since_token: StreamToken,
         end_token: StreamToken,
-        members_to_fetch: Optional[Set[str]],
+        members_to_fetch: set[str] | None,
         timeline_state: StateMap[str],
     ) -> StateMap[str]:
         """Calculate the state events to be included in an incremental sync response.
@@ -1566,7 +1554,7 @@ class SyncHandler:
 
         # Identify memberships missing from `found_state_ids` and pick out the auth
         # events in which to look for them.
-        auth_event_ids: Set[str] = set()
+        auth_event_ids: set[str] = set()
         for member in members_to_fetch:
             if (EventTypes.Member, member) in found_state_ids:
                 continue
@@ -1658,7 +1646,7 @@ class SyncHandler:
     async def generate_sync_result(
         self,
         sync_config: SyncConfig,
-        since_token: Optional[StreamToken] = None,
+        since_token: StreamToken | None = None,
         full_state: bool = False,
     ) -> SyncResult:
         """Generates the response body of a sync result.
@@ -1769,7 +1757,7 @@ class SyncHandler:
         logger.debug("Fetching OTK data")
         device_id = sync_config.device_id
         one_time_keys_count: JsonMapping = {}
-        unused_fallback_key_types: List[str] = []
+        unused_fallback_key_types: list[str] = []
         if device_id:
             # TODO: We should have a way to let clients differentiate between the states of:
             #   * no change in OTK count since the provided since token
@@ -1813,7 +1801,7 @@ class SyncHandler:
     async def get_sync_result_builder(
         self,
         sync_config: SyncConfig,
-        since_token: Optional[StreamToken] = None,
+        since_token: StreamToken | None = None,
         full_state: bool = False,
     ) -> "SyncResultBuilder":
         """
@@ -1859,7 +1847,7 @@ class SyncHandler:
                 self.rooms_to_exclude_globally,
             )
 
-            last_membership_change_by_room_id: Dict[str, EventBase] = {}
+            last_membership_change_by_room_id: dict[str, EventBase] = {}
             for event in membership_change_events:
                 last_membership_change_by_room_id[event.room_id] = event
 
@@ -1918,7 +1906,7 @@ class SyncHandler:
         # - are full-stated
         # - became fully-stated at some point during the sync period
         #   (These rooms will have been omitted during a previous eager sync.)
-        forced_newly_joined_room_ids: Set[str] = set()
+        forced_newly_joined_room_ids: set[str] = set()
         if since_token and not sync_config.filter_collection.lazy_load_members():
             un_partial_stated_rooms = (
                 await self.store.get_un_partial_stated_rooms_between(
@@ -2127,7 +2115,7 @@ class SyncHandler:
 
     async def _generate_sync_entry_for_rooms(
         self, sync_result_builder: "SyncResultBuilder"
-    ) -> Tuple[AbstractSet[str], AbstractSet[str]]:
+    ) -> tuple[AbstractSet[str], AbstractSet[str]]:
         """Generates the rooms portion of the sync response. Populates the
         `sync_result_builder` with the result.
 
@@ -2176,7 +2164,7 @@ class SyncHandler:
             or sync_result_builder.sync_config.filter_collection.blocks_all_room_ephemeral()
         )
         if block_all_room_ephemeral:
-            ephemeral_by_room: Dict[str, List[JsonDict]] = {}
+            ephemeral_by_room: dict[str, list[JsonDict]] = {}
         else:
             now_token, ephemeral_by_room = await self.ephemeral_by_room(
                 sync_result_builder,
@@ -2270,7 +2258,7 @@ class SyncHandler:
     async def _get_room_changes_for_incremental_sync(
         self,
         sync_result_builder: "SyncResultBuilder",
-        ignored_users: FrozenSet[str],
+        ignored_users: frozenset[str],
     ) -> _RoomChanges:
         """Determine the changes in rooms to report to the user.
 
@@ -2301,17 +2289,17 @@ class SyncHandler:
 
         assert since_token
 
-        mem_change_events_by_room_id: Dict[str, List[EventBase]] = {}
+        mem_change_events_by_room_id: dict[str, list[EventBase]] = {}
         for event in membership_change_events:
             mem_change_events_by_room_id.setdefault(event.room_id, []).append(event)
 
-        newly_joined_rooms: List[str] = list(
+        newly_joined_rooms: list[str] = list(
             sync_result_builder.forced_newly_joined_room_ids
         )
-        newly_left_rooms: List[str] = []
-        room_entries: List[RoomSyncResultBuilder] = []
-        invited: List[InvitedSyncResult] = []
-        knocked: List[KnockedSyncResult] = []
+        newly_left_rooms: list[str] = []
+        room_entries: list[RoomSyncResultBuilder] = []
+        invited: list[InvitedSyncResult] = []
+        knocked: list[KnockedSyncResult] = []
         invite_config = await self.store.get_invite_config_for_user(user_id)
         for room_id, events in mem_change_events_by_room_id.items():
             # The body of this loop will add this room to at least one of the five lists
@@ -2448,7 +2436,7 @@ class SyncHandler:
                 # This is all screaming out for a refactor, as the logic here is
                 # subtle and the moving parts numerous.
                 if leave_event.internal_metadata.is_out_of_band_membership():
-                    batch_events: Optional[List[EventBase]] = [leave_event]
+                    batch_events: list[EventBase] | None = [leave_event]
                 else:
                     batch_events = None
 
@@ -2530,7 +2518,7 @@ class SyncHandler:
     async def _get_room_changes_for_initial_sync(
         self,
         sync_result_builder: "SyncResultBuilder",
-        ignored_users: FrozenSet[str],
+        ignored_users: frozenset[str],
     ) -> _RoomChanges:
         """Returns entries for all rooms for the user.
 
@@ -2616,8 +2604,8 @@ class SyncHandler:
         self,
         sync_result_builder: "SyncResultBuilder",
         room_builder: "RoomSyncResultBuilder",
-        ephemeral: List[JsonDict],
-        tags: Optional[Mapping[str, JsonMapping]],
+        ephemeral: list[JsonDict],
+        tags: Mapping[str, JsonMapping] | None,
         account_data: Mapping[str, JsonMapping],
         always_include: bool = False,
     ) -> None:
@@ -2732,9 +2720,17 @@ class SyncHandler:
                 )
             )
 
-            ephemeral = await sync_config.filter_collection.filter_room_ephemeral(
-                ephemeral
-            )
+            ephemeral = [
+                # per spec, ephemeral events (typing notifications and read receipts)
+                # should not have a `room_id` field when sent to clients
+                # refs:
+                # - https://spec.matrix.org/v1.16/client-server-api/#mtyping
+                # - https://spec.matrix.org/v1.16/client-server-api/#mreceipt
+                {k: v for (k, v) in event.items() if k != "room_id"}
+                for event in await sync_config.filter_collection.filter_room_ephemeral(
+                    ephemeral
+                )
+            ]
 
             if not (
                 always_include
@@ -2759,7 +2755,7 @@ class SyncHandler:
                 # An out of band room won't have any state changes.
                 state = {}
 
-            summary: Optional[JsonDict] = {}
+            summary: JsonDict | None = {}
 
             # we include a summary in room responses when we're lazy loading
             # members (as the client otherwise doesn't have enough info to form
@@ -2787,7 +2783,7 @@ class SyncHandler:
                 )
 
             if room_builder.rtype == "joined":
-                unread_notifications: Dict[str, int] = {}
+                unread_notifications: dict[str, int] = {}
                 room_sync = JoinedSyncResult(
                     room_id=room_id,
                     timeline=batch,
@@ -2854,7 +2850,7 @@ class SyncHandler:
                 raise Exception("Unrecognized rtype: %r", room_builder.rtype)
 
 
-def _action_has_highlight(actions: List[JsonDict]) -> bool:
+def _action_has_highlight(actions: list[JsonDict]) -> bool:
     for action in actions:
         try:
             if action.get("set_tweak", None) == "highlight":
@@ -3008,22 +3004,22 @@ class SyncResultBuilder:
 
     sync_config: SyncConfig
     full_state: bool
-    since_token: Optional[StreamToken]
+    since_token: StreamToken | None
     now_token: StreamToken
-    joined_room_ids: FrozenSet[str]
-    excluded_room_ids: FrozenSet[str]
-    forced_newly_joined_room_ids: FrozenSet[str]
-    membership_change_events: List[EventBase]
+    joined_room_ids: frozenset[str]
+    excluded_room_ids: frozenset[str]
+    forced_newly_joined_room_ids: frozenset[str]
+    membership_change_events: list[EventBase]
 
-    presence: List[UserPresenceState] = attr.Factory(list)
-    account_data: List[JsonDict] = attr.Factory(list)
-    joined: List[JoinedSyncResult] = attr.Factory(list)
-    invited: List[InvitedSyncResult] = attr.Factory(list)
-    knocked: List[KnockedSyncResult] = attr.Factory(list)
-    archived: List[ArchivedSyncResult] = attr.Factory(list)
-    to_device: List[JsonDict] = attr.Factory(list)
+    presence: list[UserPresenceState] = attr.Factory(list)
+    account_data: list[JsonDict] = attr.Factory(list)
+    joined: list[JoinedSyncResult] = attr.Factory(list)
+    invited: list[InvitedSyncResult] = attr.Factory(list)
+    knocked: list[KnockedSyncResult] = attr.Factory(list)
+    archived: list[ArchivedSyncResult] = attr.Factory(list)
+    to_device: list[JsonDict] = attr.Factory(list)
 
-    def calculate_user_changes(self) -> Tuple[AbstractSet[str], AbstractSet[str]]:
+    def calculate_user_changes(self) -> tuple[AbstractSet[str], AbstractSet[str]]:
         """Work out which other users have joined or left rooms we are joined to.
 
         This data only is only useful for an incremental sync.
@@ -3101,10 +3097,10 @@ class RoomSyncResultBuilder:
 
     room_id: str
     rtype: str
-    events: Optional[List[EventBase]]
+    events: list[EventBase] | None
     newly_joined: bool
     full_state: bool
-    since_token: Optional[StreamToken]
+    since_token: StreamToken | None
     upto_token: StreamToken
     end_token: StreamToken
     out_of_band: bool = False
diff --git a/synapse/handlers/thread_subscriptions.py b/synapse/handlers/thread_subscriptions.py
index d56c915e0a..539672c7fe 100644
--- a/synapse/handlers/thread_subscriptions.py
+++ b/synapse/handlers/thread_subscriptions.py
@@ -1,6 +1,6 @@
 import logging
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING
 
 from synapse.api.constants import RelationTypes
 from synapse.api.errors import AuthError, Codes, NotFoundError, SynapseError
@@ -29,7 +29,7 @@ class ThreadSubscriptionsHandler:
         user_id: UserID,
         room_id: str,
         thread_root_event_id: str,
-    ) -> Optional[ThreadSubscription]:
+    ) -> ThreadSubscription | None:
         """Get thread subscription settings for a specific thread and user.
         Checks that the thread root is both a real event and also that it is visible
         to the user.
@@ -62,8 +62,8 @@ class ThreadSubscriptionsHandler:
         room_id: str,
         thread_root_event_id: str,
         *,
-        automatic_event_id: Optional[str],
-    ) -> Optional[int]:
+        automatic_event_id: str | None,
+    ) -> int | None:
         """Sets or updates a user's subscription settings for a specific thread root.
 
         Args:
@@ -146,7 +146,7 @@ class ThreadSubscriptionsHandler:
 
     async def unsubscribe_user_from_thread(
         self, user_id: UserID, room_id: str, thread_root_event_id: str
-    ) -> Optional[int]:
+    ) -> int | None:
         """Clears a user's subscription settings for a specific thread root.
 
         Args:
diff --git a/synapse/handlers/typing.py b/synapse/handlers/typing.py
index 6a7b36ea0c..8b577d5d58 100644
--- a/synapse/handlers/typing.py
+++ b/synapse/handlers/typing.py
@@ -20,7 +20,7 @@
 #
 import logging
 import random
-from typing import TYPE_CHECKING, Dict, Iterable, List, Optional, Set, Tuple
+from typing import TYPE_CHECKING, Iterable
 
 import attr
 
@@ -28,7 +28,6 @@ from synapse.api.constants import EduTypes
 from synapse.api.errors import AuthError, ShadowBanError, SynapseError
 from synapse.appservice import ApplicationService
 from synapse.metrics.background_process_metrics import (
-    run_as_background_process,
     wrap_as_background_process,
 )
 from synapse.replication.tcp.streams import TypingStream
@@ -78,11 +77,10 @@ class FollowerTypingHandler:
     """
 
     def __init__(self, hs: "HomeServer"):
+        self.hs = hs  # nb must be called this for @wrap_as_background_process
         self.store = hs.get_datastores().main
         self._storage_controllers = hs.get_storage_controllers()
-        self.server_name = (
-            hs.hostname
-        )  # nb must be called this for @wrap_as_background_process
+        self.server_name = hs.hostname
         self.clock = hs.get_clock()
         self.is_mine_id = hs.is_mine_id
         self.is_mine_server_name = hs.is_mine_server_name
@@ -98,15 +96,15 @@ class FollowerTypingHandler:
             )
 
         # map room IDs to serial numbers
-        self._room_serials: Dict[str, int] = {}
+        self._room_serials: dict[str, int] = {}
         # map room IDs to sets of users currently typing
-        self._room_typing: Dict[str, Set[str]] = {}
+        self._room_typing: dict[str, set[str]] = {}
 
-        self._member_last_federation_poke: Dict[RoomMember, int] = {}
+        self._member_last_federation_poke: dict[RoomMember, int] = {}
         self.wheel_timer: WheelTimer[RoomMember] = WheelTimer(bucket_size=5000)
         self._latest_room_serial = 0
 
-        self._rooms_updated: Set[str] = set()
+        self._rooms_updated: set[str] = set()
 
         self.clock.looping_call(self._handle_timeouts, 5000)
         self.clock.looping_call(self._prune_old_typing, FORGET_TIMEOUT)
@@ -144,9 +142,8 @@ class FollowerTypingHandler:
         if self.federation and self.is_mine_id(member.user_id):
             last_fed_poke = self._member_last_federation_poke.get(member, None)
             if not last_fed_poke or last_fed_poke + FEDERATION_PING_INTERVAL <= now:
-                run_as_background_process(
+                self.hs.run_as_background_process(
                     "typing._push_remote",
-                    self.server_name,
                     self._push_remote,
                     member=member,
                     typing=True,
@@ -198,7 +195,7 @@ class FollowerTypingHandler:
             logger.exception("Error pushing typing notif to remotes")
 
     def process_replication_rows(
-        self, token: int, rows: List[TypingStream.TypingStreamRow]
+        self, token: int, rows: list[TypingStream.TypingStreamRow]
     ) -> None:
         """Should be called whenever we receive updates for typing stream."""
 
@@ -220,9 +217,8 @@ class FollowerTypingHandler:
             self._rooms_updated.add(row.room_id)
 
             if self.federation:
-                run_as_background_process(
+                self.hs.run_as_background_process(
                     "_send_changes_in_typing_to_remotes",
-                    self.server_name,
                     self._send_changes_in_typing_to_remotes,
                     row.room_id,
                     prev_typing,
@@ -230,7 +226,7 @@ class FollowerTypingHandler:
                 )
 
     async def _send_changes_in_typing_to_remotes(
-        self, room_id: str, prev_typing: Set[str], now_typing: Set[str]
+        self, room_id: str, prev_typing: set[str], now_typing: set[str]
     ) -> None:
         """Process a change in typing of a room from replication, sending EDUs
         for any local users.
@@ -284,7 +280,7 @@ class TypingWriterHandler(FollowerTypingHandler):
         hs.get_distributor().observe("user_left_room", self.user_left_room)
 
         # clock time we expect to stop
-        self._member_typing_until: Dict[RoomMember, int] = {}
+        self._member_typing_until: dict[RoomMember, int] = {}
 
         # caches which room_ids changed at which serials
         self._typing_stream_change_cache = StreamChangeCache(
@@ -384,9 +380,8 @@ class TypingWriterHandler(FollowerTypingHandler):
     def _push_update(self, member: RoomMember, typing: bool) -> None:
         if self.hs.is_mine_id(member.user_id):
             # Only send updates for changes to our own users.
-            run_as_background_process(
+            self.hs.run_as_background_process(
                 "typing._push_remote",
-                self.server_name,
                 self._push_remote,
                 member,
                 typing,
@@ -457,7 +452,7 @@ class TypingWriterHandler(FollowerTypingHandler):
 
     async def get_all_typing_updates(
         self, instance_name: str, last_id: int, current_id: int, limit: int
-    ) -> Tuple[List[Tuple[int, list]], int, bool]:
+    ) -> tuple[list[tuple[int, list]], int, bool]:
         """Get updates for typing replication stream.
 
         Args:
@@ -509,7 +504,7 @@ class TypingWriterHandler(FollowerTypingHandler):
         return rows, current_id, limited
 
     def process_replication_rows(
-        self, token: int, rows: List[TypingStream.TypingStreamRow]
+        self, token: int, rows: list[TypingStream.TypingStreamRow]
     ) -> None:
         # The writing process should never get updates from replication.
         raise Exception("Typing writer instance got typing info over replication")
@@ -536,7 +531,7 @@ class TypingNotificationEventSource(EventSource[int, JsonMapping]):
 
     async def get_new_events_as(
         self, from_key: int, service: ApplicationService
-    ) -> Tuple[List[JsonMapping], int]:
+    ) -> tuple[list[JsonMapping], int]:
         """Returns a set of new typing events that an appservice
         may be interested in.
 
@@ -581,9 +576,9 @@ class TypingNotificationEventSource(EventSource[int, JsonMapping]):
         limit: int,
         room_ids: Iterable[str],
         is_guest: bool,
-        explicit_room_id: Optional[str] = None,
-        to_key: Optional[int] = None,
-    ) -> Tuple[List[JsonMapping], int]:
+        explicit_room_id: str | None = None,
+        to_key: int | None = None,
+    ) -> tuple[list[JsonMapping], int]:
         """
         Find typing notifications for given rooms (> `from_token` and <= `to_token`)
         """
diff --git a/synapse/handlers/ui_auth/checkers.py b/synapse/handlers/ui_auth/checkers.py
index f3c295d9f2..a0097dbc96 100644
--- a/synapse/handlers/ui_auth/checkers.py
+++ b/synapse/handlers/ui_auth/checkers.py
@@ -21,7 +21,7 @@
 
 import logging
 from abc import ABC, abstractmethod
-from typing import TYPE_CHECKING, Any, ClassVar, Sequence, Type
+from typing import TYPE_CHECKING, Any, ClassVar, Sequence
 
 from twisted.web.client import PartialDownloadError
 
@@ -136,7 +136,7 @@ class RecaptchaAuthChecker(UserInteractiveAuthChecker):
         except PartialDownloadError as pde:
             # Twisted is silly
             data = pde.response
-            # For mypy's benefit. A general Error.response is Optional[bytes], but
+            # For mypy's benefit. A general Error.response is bytes | None, but
             # a PartialDownloadError.response should be bytes AFAICS.
             assert data is not None
             resp_body = json_decoder.decode(data.decode("utf-8"))
@@ -321,7 +321,7 @@ class RegistrationTokenAuthChecker(UserInteractiveAuthChecker):
             )
 
 
-INTERACTIVE_AUTH_CHECKERS: Sequence[Type[UserInteractiveAuthChecker]] = [
+INTERACTIVE_AUTH_CHECKERS: Sequence[type[UserInteractiveAuthChecker]] = [
     DummyAuthChecker,
     TermsAuthChecker,
     RecaptchaAuthChecker,
diff --git a/synapse/handlers/user_directory.py b/synapse/handlers/user_directory.py
index 130099a239..e5210a3e97 100644
--- a/synapse/handlers/user_directory.py
+++ b/synapse/handlers/user_directory.py
@@ -21,7 +21,7 @@
 
 import logging
 from http import HTTPStatus
-from typing import TYPE_CHECKING, List, Optional, Set, Tuple
+from typing import TYPE_CHECKING
 
 from twisted.internet.interfaces import IDelayedCall
 
@@ -36,7 +36,6 @@ from synapse.api.constants import (
 from synapse.api.errors import Codes, SynapseError
 from synapse.handlers.state_deltas import MatchChange, StateDeltasHandler
 from synapse.metrics import SERVER_NAME_LABEL
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.storage.databases.main.state_deltas import StateDelta
 from synapse.storage.databases.main.user_directory import SearchResult
 from synapse.storage.roommember import ProfileInfo
@@ -117,7 +116,7 @@ class UserDirectoryHandler(StateDeltasHandler):
         self._hs = hs
 
         # The current position in the current_state_delta stream
-        self.pos: Optional[int] = None
+        self.pos: int | None = None
 
         # Guard to ensure we only process deltas one at a time
         self._is_processing = False
@@ -125,23 +124,27 @@ class UserDirectoryHandler(StateDeltasHandler):
         # Guard to ensure we only have one process for refreshing remote profiles
         self._is_refreshing_remote_profiles = False
         # Handle to cancel the `call_later` of `kick_off_remote_profile_refresh_process`
-        self._refresh_remote_profiles_call_later: Optional[IDelayedCall] = None
+        self._refresh_remote_profiles_call_later: IDelayedCall | None = None
 
         # Guard to ensure we only have one process for refreshing remote profiles
         # for the given servers.
         # Set of server names.
-        self._is_refreshing_remote_profiles_for_servers: Set[str] = set()
+        self._is_refreshing_remote_profiles_for_servers: set[str] = set()
 
         if self.update_user_directory:
             self.notifier.add_replication_callback(self.notify_new_event)
 
             # We kick this off so that we don't have to wait for a change before
             # we start populating the user directory
-            self.clock.call_later(0, self.notify_new_event)
+            self.clock.call_later(
+                0,
+                self.notify_new_event,
+            )
 
             # Kick off the profile refresh process on startup
             self._refresh_remote_profiles_call_later = self.clock.call_later(
-                10, self.kick_off_remote_profile_refresh_process
+                10,
+                self.kick_off_remote_profile_refresh_process,
             )
 
     async def search_users(
@@ -193,9 +196,7 @@ class UserDirectoryHandler(StateDeltasHandler):
                 self._is_processing = False
 
         self._is_processing = True
-        run_as_background_process(
-            "user_directory.notify_new_event", self.server_name, process
-        )
+        self._hs.run_as_background_process("user_directory.notify_new_event", process)
 
     async def handle_local_profile_change(
         self, user_id: str, profile: ProfileInfo
@@ -269,7 +270,7 @@ class UserDirectoryHandler(StateDeltasHandler):
 
                 await self.store.update_user_directory_stream_pos(max_pos)
 
-    async def _handle_deltas(self, deltas: List[StateDelta]) -> None:
+    async def _handle_deltas(self, deltas: list[StateDelta]) -> None:
         """Called with the state deltas to process"""
         for delta in deltas:
             logger.debug(
@@ -298,8 +299,8 @@ class UserDirectoryHandler(StateDeltasHandler):
     async def _handle_room_publicity_change(
         self,
         room_id: str,
-        prev_event_id: Optional[str],
-        event_id: Optional[str],
+        prev_event_id: str | None,
+        event_id: str | None,
         typ: str,
     ) -> None:
         """Handle a room having potentially changed from/to world_readable/publicly
@@ -371,8 +372,8 @@ class UserDirectoryHandler(StateDeltasHandler):
     async def _handle_room_membership_event(
         self,
         room_id: str,
-        prev_event_id: Optional[str],
-        event_id: Optional[str],
+        prev_event_id: str | None,
+        event_id: str | None,
         state_key: str,
     ) -> None:
         """Process a single room membershp event.
@@ -465,7 +466,7 @@ class UserDirectoryHandler(StateDeltasHandler):
                     or await self.store.should_include_local_user_in_dir(other)
                 )
             ]
-            updates_to_users_who_share_rooms: Set[Tuple[str, str]] = set()
+            updates_to_users_who_share_rooms: set[tuple[str, str]] = set()
 
             # First, if the joining user is our local user then we need an
             # update for every other user in the room.
@@ -518,7 +519,7 @@ class UserDirectoryHandler(StateDeltasHandler):
         self,
         user_id: str,
         room_id: str,
-        prev_event_id: Optional[str],
+        prev_event_id: str | None,
         event_id: str,
     ) -> None:
         """Check member event changes for any profile changes and update the
@@ -609,8 +610,8 @@ class UserDirectoryHandler(StateDeltasHandler):
                 self._is_refreshing_remote_profiles = False
 
         self._is_refreshing_remote_profiles = True
-        run_as_background_process(
-            "user_directory.refresh_remote_profiles", self.server_name, process
+        self._hs.run_as_background_process(
+            "user_directory.refresh_remote_profiles", process
         )
 
     async def _unsafe_refresh_remote_profiles(self) -> None:
@@ -655,8 +656,9 @@ class UserDirectoryHandler(StateDeltasHandler):
                 if not users:
                     return
                 _, _, next_try_at_ts = users[0]
+                delay = ((next_try_at_ts - self.clock.time_msec()) // 1000) + 2
                 self._refresh_remote_profiles_call_later = self.clock.call_later(
-                    ((next_try_at_ts - self.clock.time_msec()) // 1000) + 2,
+                    delay,
                     self.kick_off_remote_profile_refresh_process,
                 )
 
@@ -692,9 +694,8 @@ class UserDirectoryHandler(StateDeltasHandler):
                 self._is_refreshing_remote_profiles_for_servers.remove(server_name)
 
         self._is_refreshing_remote_profiles_for_servers.add(server_name)
-        run_as_background_process(
+        self._hs.run_as_background_process(
             "user_directory.refresh_remote_profiles_for_remote_server",
-            self.server_name,
             process,
         )
 
diff --git a/synapse/handlers/worker_lock.py b/synapse/handlers/worker_lock.py
index 0b375790dd..3e097d21f2 100644
--- a/synapse/handlers/worker_lock.py
+++ b/synapse/handlers/worker_lock.py
@@ -26,24 +26,19 @@ from typing import (
     TYPE_CHECKING,
     AsyncContextManager,
     Collection,
-    Dict,
-    Optional,
-    Tuple,
-    Type,
-    Union,
 )
 from weakref import WeakSet
 
 import attr
 
 from twisted.internet import defer
-from twisted.internet.interfaces import IReactorTime
 
 from synapse.logging.context import PreserveLoggingContext
 from synapse.logging.opentracing import start_active_span
 from synapse.metrics.background_process_metrics import wrap_as_background_process
 from synapse.storage.databases.main.lock import Lock, LockStore
 from synapse.util.async_helpers import timeout_deferred
+from synapse.util.clock import Clock
 from synapse.util.constants import ONE_MINUTE_SECONDS
 
 if TYPE_CHECKING:
@@ -66,10 +61,8 @@ class WorkerLocksHandler:
     """
 
     def __init__(self, hs: "HomeServer") -> None:
-        self.server_name = (
-            hs.hostname
-        )  # nb must be called this for @wrap_as_background_process
-        self._reactor = hs.get_reactor()
+        self.hs = hs  # nb must be called this for @wrap_as_background_process
+        self._clock = hs.get_clock()
         self._store = hs.get_datastores().main
         self._clock = hs.get_clock()
         self._notifier = hs.get_notifier()
@@ -77,9 +70,7 @@ class WorkerLocksHandler:
 
         # Map from lock name/key to set of `WaitingLock` that are active for
         # that lock.
-        self._locks: Dict[
-            Tuple[str, str], WeakSet[Union[WaitingLock, WaitingMultiLock]]
-        ] = {}
+        self._locks: dict[tuple[str, str], WeakSet[WaitingLock | WaitingMultiLock]] = {}
 
         self._clock.looping_call(self._cleanup_locks, 30_000)
 
@@ -98,7 +89,7 @@ class WorkerLocksHandler:
         """
 
         lock = WaitingLock(
-            reactor=self._reactor,
+            clock=self._clock,
             store=self._store,
             handler=self,
             lock_name=lock_name,
@@ -129,7 +120,7 @@ class WorkerLocksHandler:
         """
 
         lock = WaitingLock(
-            reactor=self._reactor,
+            clock=self._clock,
             store=self._store,
             handler=self,
             lock_name=lock_name,
@@ -143,7 +134,7 @@ class WorkerLocksHandler:
 
     def acquire_multi_read_write_lock(
         self,
-        lock_names: Collection[Tuple[str, str]],
+        lock_names: Collection[tuple[str, str]],
         *,
         write: bool,
     ) -> "WaitingMultiLock":
@@ -160,7 +151,7 @@ class WorkerLocksHandler:
         lock = WaitingMultiLock(
             lock_names=lock_names,
             write=write,
-            reactor=self._reactor,
+            clock=self._clock,
             store=self._store,
             handler=self,
         )
@@ -190,14 +181,18 @@ class WorkerLocksHandler:
             return
 
         def _wake_all_locks(
-            locks: Collection[Union[WaitingLock, WaitingMultiLock]],
+            locks: Collection[WaitingLock | WaitingMultiLock],
         ) -> None:
             for lock in locks:
                 deferred = lock.deferred
                 if not deferred.called:
                     deferred.callback(None)
 
-        self._clock.call_later(0, _wake_all_locks, locks)
+        self._clock.call_later(
+            0,
+            _wake_all_locks,
+            locks,
+        )
 
     @wrap_as_background_process("_cleanup_locks")
     async def _cleanup_locks(self) -> None:
@@ -207,14 +202,14 @@ class WorkerLocksHandler:
 
 @attr.s(auto_attribs=True, eq=False)
 class WaitingLock:
-    reactor: IReactorTime
+    clock: Clock
     store: LockStore
     handler: WorkerLocksHandler
     lock_name: str
     lock_key: str
-    write: Optional[bool]
+    write: bool | None
     deferred: "defer.Deferred[None]" = attr.Factory(defer.Deferred)
-    _inner_lock: Optional[Lock] = None
+    _inner_lock: Lock | None = None
     _retry_interval: float = 0.1
     _lock_span: "opentracing.Scope" = attr.Factory(
         lambda: start_active_span("WaitingLock.lock")
@@ -246,10 +241,11 @@ class WaitingLock:
                     # periodically wake up in case the lock was released but we
                     # weren't notified.
                     with PreserveLoggingContext():
+                        timeout = self._get_next_retry_interval()
                         await timeout_deferred(
                             deferred=self.deferred,
-                            timeout=self._get_next_retry_interval(),
-                            reactor=self.reactor,
+                            timeout=timeout,
+                            clock=self.clock,
                         )
                 except Exception:
                     pass
@@ -258,10 +254,10 @@ class WaitingLock:
 
     async def __aexit__(
         self,
-        exc_type: Optional[Type[BaseException]],
-        exc: Optional[BaseException],
-        tb: Optional[TracebackType],
-    ) -> Optional[bool]:
+        exc_type: type[BaseException] | None,
+        exc: BaseException | None,
+        tb: TracebackType | None,
+    ) -> bool | None:
         assert self._inner_lock
 
         self.handler.notify_lock_released(self.lock_name, self.lock_key)
@@ -286,17 +282,17 @@ class WaitingLock:
 
 @attr.s(auto_attribs=True, eq=False)
 class WaitingMultiLock:
-    lock_names: Collection[Tuple[str, str]]
+    lock_names: Collection[tuple[str, str]]
 
     write: bool
 
-    reactor: IReactorTime
+    clock: Clock
     store: LockStore
     handler: WorkerLocksHandler
 
     deferred: "defer.Deferred[None]" = attr.Factory(defer.Deferred)
 
-    _inner_lock_cm: Optional[AsyncContextManager] = None
+    _inner_lock_cm: AsyncContextManager | None = None
     _retry_interval: float = 0.1
     _lock_span: "opentracing.Scope" = attr.Factory(
         lambda: start_active_span("WaitingLock.lock")
@@ -323,10 +319,11 @@ class WaitingMultiLock:
                     # periodically wake up in case the lock was released but we
                     # weren't notified.
                     with PreserveLoggingContext():
+                        timeout = self._get_next_retry_interval()
                         await timeout_deferred(
                             deferred=self.deferred,
-                            timeout=self._get_next_retry_interval(),
-                            reactor=self.reactor,
+                            timeout=timeout,
+                            clock=self.clock,
                         )
                 except Exception:
                     pass
@@ -337,10 +334,10 @@ class WaitingMultiLock:
 
     async def __aexit__(
         self,
-        exc_type: Optional[Type[BaseException]],
-        exc: Optional[BaseException],
-        tb: Optional[TracebackType],
-    ) -> Optional[bool]:
+        exc_type: type[BaseException] | None,
+        exc: BaseException | None,
+        tb: TracebackType | None,
+    ) -> bool | None:
         assert self._inner_lock_cm
 
         for lock_name, lock_key in self.lock_names:
diff --git a/synapse/http/__init__.py b/synapse/http/__init__.py
index 272bbc05f9..f13271f302 100644
--- a/synapse/http/__init__.py
+++ b/synapse/http/__init__.py
@@ -19,7 +19,6 @@
 #
 #
 import re
-from typing import Union
 
 from twisted.internet import address, task
 from twisted.web.client import FileBodyProducer
@@ -75,7 +74,7 @@ def _get_requested_host(request: IRequest) -> bytes:
         return hostname
 
     # no Host header, use the address/port that the request arrived on
-    host: Union[address.IPv4Address, address.IPv6Address] = request.getHost()
+    host: address.IPv4Address | address.IPv6Address = request.getHost()
 
     hostname = host.host.encode("ascii")
 
diff --git a/synapse/http/additional_resource.py b/synapse/http/additional_resource.py
index 59eae841d5..3661a2aeb7 100644
--- a/synapse/http/additional_resource.py
+++ b/synapse/http/additional_resource.py
@@ -18,7 +18,7 @@
 #
 #
 
-from typing import TYPE_CHECKING, Any, Awaitable, Callable, Optional, Tuple
+from typing import TYPE_CHECKING, Any, Awaitable, Callable
 
 from twisted.web.server import Request
 
@@ -41,7 +41,7 @@ class AdditionalResource(DirectServeJsonResource):
     def __init__(
         self,
         hs: "HomeServer",
-        handler: Callable[[Request], Awaitable[Optional[Tuple[int, Any]]]],
+        handler: Callable[[Request], Awaitable[tuple[int, Any] | None]],
     ):
         """Initialise AdditionalResource
 
@@ -56,7 +56,7 @@ class AdditionalResource(DirectServeJsonResource):
         super().__init__(clock=hs.get_clock())
         self._handler = handler
 
-    async def _async_render(self, request: Request) -> Optional[Tuple[int, Any]]:
+    async def _async_render(self, request: Request) -> tuple[int, Any] | None:
         # Cheekily pass the result straight through, so we don't need to worry
         # if its an awaitable or not.
         return await self._handler(request)
diff --git a/synapse/http/client.py b/synapse/http/client.py
index bbb0efe8b5..9971accccd 100644
--- a/synapse/http/client.py
+++ b/synapse/http/client.py
@@ -27,13 +27,8 @@ from typing import (
     Any,
     BinaryIO,
     Callable,
-    Dict,
-    List,
     Mapping,
-    Optional,
     Protocol,
-    Tuple,
-    Union,
 )
 
 import attr
@@ -54,7 +49,6 @@ from twisted.internet.interfaces import (
     IOpenSSLContextFactory,
     IReactorCore,
     IReactorPluggableNameResolver,
-    IReactorTime,
     IResolutionReceiver,
     ITCPTransport,
 )
@@ -88,6 +82,7 @@ from synapse.logging.opentracing import set_tag, start_active_span, tags
 from synapse.metrics import SERVER_NAME_LABEL
 from synapse.types import ISynapseReactor, StrSequence
 from synapse.util.async_helpers import timeout_deferred
+from synapse.util.clock import Clock
 from synapse.util.json import json_decoder
 
 if TYPE_CHECKING:
@@ -121,7 +116,7 @@ incoming_responses_counter = Counter(
 # the type of the headers map, to be passed to the t.w.h.Headers.
 #
 # The actual type accepted by Twisted is
-#   Mapping[Union[str, bytes], Sequence[Union[str, bytes]] ,
+#   Mapping[str | bytes], Sequence[str | bytes] ,
 # allowing us to mix and match str and bytes freely. However: any str is also a
 # Sequence[str]; passing a header string value which is a
 # standalone str is interpreted as a sequence of 1-codepoint strings. This is a disastrous footgun.
@@ -129,21 +124,21 @@ incoming_responses_counter = Counter(
 #
 # We also simplify the keys to be either all str or all bytes. This helps because
 # Dict[K, V] is invariant in K (and indeed V).
-RawHeaders = Union[Mapping[str, "RawHeaderValue"], Mapping[bytes, "RawHeaderValue"]]
+RawHeaders = Mapping[str, "RawHeaderValue"] | Mapping[bytes, "RawHeaderValue"]
 
 # the value actually has to be a List, but List is invariant so we can't specify that
 # the entries can either be Lists or bytes.
-RawHeaderValue = Union[
-    StrSequence,
-    List[bytes],
-    List[Union[str, bytes]],
-    Tuple[bytes, ...],
-    Tuple[Union[str, bytes], ...],
-]
+RawHeaderValue = (
+    StrSequence
+    | list[bytes]
+    | list[str | bytes]
+    | tuple[bytes, ...]
+    | tuple[str | bytes, ...]
+)
 
 
 def _is_ip_blocked(
-    ip_address: IPAddress, allowlist: Optional[IPSet], blocklist: IPSet
+    ip_address: IPAddress, allowlist: IPSet | None, blocklist: IPSet
 ) -> bool:
     """
     Compares an IP address to allowed and disallowed IP sets.
@@ -165,16 +160,17 @@ def _is_ip_blocked(
 _EPSILON = 0.00000001
 
 
-def _make_scheduler(
-    reactor: IReactorTime,
-) -> Callable[[Callable[[], object]], IDelayedCall]:
+def _make_scheduler(clock: Clock) -> Callable[[Callable[[], object]], IDelayedCall]:
     """Makes a schedular suitable for a Cooperator using the given reactor.
 
     (This is effectively just a copy from `twisted.internet.task`)
     """
 
     def _scheduler(x: Callable[[], object]) -> IDelayedCall:
-        return reactor.callLater(_EPSILON, x)
+        return clock.call_later(
+            _EPSILON,
+            x,
+        )
 
     return _scheduler
 
@@ -188,7 +184,7 @@ class _IPBlockingResolver:
     def __init__(
         self,
         reactor: IReactorPluggableNameResolver,
-        ip_allowlist: Optional[IPSet],
+        ip_allowlist: IPSet | None,
         ip_blocklist: IPSet,
     ):
         """
@@ -204,7 +200,7 @@ class _IPBlockingResolver:
     def resolveHostName(
         self, recv: IResolutionReceiver, hostname: str, portNumber: int = 0
     ) -> IResolutionReceiver:
-        addresses: List[IAddress] = []
+        addresses: list[IAddress] = []
 
         def _callback() -> None:
             has_bad_ip = False
@@ -264,7 +260,7 @@ class BlocklistingReactorWrapper:
     def __init__(
         self,
         reactor: IReactorPluggableNameResolver,
-        ip_allowlist: Optional[IPSet],
+        ip_allowlist: IPSet | None,
         ip_blocklist: IPSet,
     ):
         self._reactor = reactor
@@ -293,7 +289,7 @@ class BlocklistingAgentWrapper(Agent):
         self,
         agent: IAgent,
         ip_blocklist: IPSet,
-        ip_allowlist: Optional[IPSet] = None,
+        ip_allowlist: IPSet | None = None,
     ):
         """
         Args:
@@ -309,13 +305,13 @@ class BlocklistingAgentWrapper(Agent):
         self,
         method: bytes,
         uri: bytes,
-        headers: Optional[Headers] = None,
-        bodyProducer: Optional[IBodyProducer] = None,
+        headers: Headers | None = None,
+        bodyProducer: IBodyProducer | None = None,
     ) -> defer.Deferred:
         h = urllib.parse.urlparse(uri.decode("ascii"))
 
         try:
-            # h.hostname is Optional[str], None raises an AddrFormatError, so
+            # h.hostname is str | None, None raises an AddrFormatError, so
             # this is safe even though IPAddress requires a str.
             ip_address = IPAddress(h.hostname)  # type: ignore[arg-type]
         except AddrFormatError:
@@ -348,7 +344,7 @@ class BaseHttpClient:
     def __init__(
         self,
         hs: "HomeServer",
-        treq_args: Optional[Dict[str, Any]] = None,
+        treq_args: dict[str, Any] | None = None,
     ):
         self.hs = hs
         self.server_name = hs.hostname
@@ -367,14 +363,14 @@ class BaseHttpClient:
 
         # We use this for our body producers to ensure that they use the correct
         # reactor.
-        self._cooperator = Cooperator(scheduler=_make_scheduler(hs.get_reactor()))
+        self._cooperator = Cooperator(scheduler=_make_scheduler(hs.get_clock()))
 
     async def request(
         self,
         method: str,
         uri: str,
-        data: Optional[bytes] = None,
-        headers: Optional[Headers] = None,
+        data: bytes | None = None,
+        headers: Headers | None = None,
     ) -> IResponse:
         """
         Args:
@@ -436,9 +432,9 @@ class BaseHttpClient:
                 # we use our own timeout mechanism rather than treq's as a workaround
                 # for https://twistedmatrix.com/trac/ticket/9534.
                 request_deferred = timeout_deferred(
-                    request_deferred,
-                    60,
-                    self.hs.get_reactor(),
+                    deferred=request_deferred,
+                    timeout=60,
+                    clock=self.hs.get_clock(),
                 )
 
                 # turn timeouts into RequestTimedOutErrors
@@ -478,8 +474,8 @@ class BaseHttpClient:
     async def post_urlencoded_get_json(
         self,
         uri: str,
-        args: Optional[Mapping[str, Union[str, List[str]]]] = None,
-        headers: Optional[RawHeaders] = None,
+        args: Mapping[str, str | list[str]] | None = None,
+        headers: RawHeaders | None = None,
     ) -> Any:
         """
         Args:
@@ -527,7 +523,7 @@ class BaseHttpClient:
             )
 
     async def post_json_get_json(
-        self, uri: str, post_json: Any, headers: Optional[RawHeaders] = None
+        self, uri: str, post_json: Any, headers: RawHeaders | None = None
     ) -> Any:
         """
 
@@ -576,8 +572,8 @@ class BaseHttpClient:
     async def get_json(
         self,
         uri: str,
-        args: Optional[QueryParams] = None,
-        headers: Optional[RawHeaders] = None,
+        args: QueryParams | None = None,
+        headers: RawHeaders | None = None,
     ) -> Any:
         """Gets some json from the given URI.
 
@@ -607,8 +603,8 @@ class BaseHttpClient:
         self,
         uri: str,
         json_body: Any,
-        args: Optional[QueryParams] = None,
-        headers: Optional[RawHeaders] = None,
+        args: QueryParams | None = None,
+        headers: RawHeaders | None = None,
     ) -> Any:
         """Puts some json to the given URI.
 
@@ -658,8 +654,8 @@ class BaseHttpClient:
     async def get_raw(
         self,
         uri: str,
-        args: Optional[QueryParams] = None,
-        headers: Optional[RawHeaders] = None,
+        args: QueryParams | None = None,
+        headers: RawHeaders | None = None,
     ) -> bytes:
         """Gets raw text from the given URI.
 
@@ -703,10 +699,10 @@ class BaseHttpClient:
         self,
         url: str,
         output_stream: BinaryIO,
-        max_size: Optional[int] = None,
-        headers: Optional[RawHeaders] = None,
-        is_allowed_content_type: Optional[Callable[[str], bool]] = None,
-    ) -> Tuple[int, Dict[bytes, List[bytes]], str, int]:
+        max_size: int | None = None,
+        headers: RawHeaders | None = None,
+        is_allowed_content_type: Callable[[str], bool] | None = None,
+    ) -> tuple[int, dict[bytes, list[bytes]], str, int]:
         """GETs a file from a given URL
         Args:
             url: The URL to GET
@@ -763,7 +759,11 @@ class BaseHttpClient:
             d = read_body_with_max_size(response, output_stream, max_size)
 
             # Ensure that the body is not read forever.
-            d = timeout_deferred(d, 30, self.hs.get_reactor())
+            d = timeout_deferred(
+                deferred=d,
+                timeout=30,
+                clock=self.hs.get_clock(),
+            )
 
             length = await make_deferred_yieldable(d)
         except BodyExceededMaxSize:
@@ -810,9 +810,9 @@ class SimpleHttpClient(BaseHttpClient):
     def __init__(
         self,
         hs: "HomeServer",
-        treq_args: Optional[Dict[str, Any]] = None,
-        ip_allowlist: Optional[IPSet] = None,
-        ip_blocklist: Optional[IPSet] = None,
+        treq_args: dict[str, Any] | None = None,
+        ip_allowlist: IPSet | None = None,
+        ip_blocklist: IPSet | None = None,
         use_proxy: bool = False,
     ):
         super().__init__(hs, treq_args=treq_args)
@@ -889,8 +889,8 @@ class ReplicationClient(BaseHttpClient):
         self,
         method: str,
         uri: str,
-        data: Optional[bytes] = None,
-        headers: Optional[Headers] = None,
+        data: bytes | None = None,
+        headers: Headers | None = None,
     ) -> IResponse:
         """
         Make a request, differs from BaseHttpClient.request in that it does not use treq.
@@ -957,9 +957,9 @@ class ReplicationClient(BaseHttpClient):
                 # for https://twistedmatrix.com/trac/ticket/9534.
                 # (Updated url https://github.com/twisted/twisted/issues/9534)
                 request_deferred = timeout_deferred(
-                    request_deferred,
-                    60,
-                    self.hs.get_reactor(),
+                    deferred=request_deferred,
+                    timeout=60,
+                    clock=self.hs.get_clock(),
                 )
 
                 # turn timeouts into RequestTimedOutErrors
@@ -1026,7 +1026,7 @@ class BodyExceededMaxSize(Exception):
 class _DiscardBodyWithMaxSizeProtocol(protocol.Protocol):
     """A protocol which immediately errors upon receiving data."""
 
-    transport: Optional[ITCPTransport] = None
+    transport: ITCPTransport | None = None
 
     def __init__(self, deferred: defer.Deferred):
         self.deferred = deferred
@@ -1056,10 +1056,10 @@ class MultipartResponse:
     """
 
     json: bytes = b"{}"
-    length: Optional[int] = None
-    content_type: Optional[bytes] = None
-    disposition: Optional[bytes] = None
-    url: Optional[bytes] = None
+    length: int | None = None
+    content_type: bytes | None = None
+    disposition: bytes | None = None
+    url: bytes | None = None
 
 
 class _MultipartParserProtocol(protocol.Protocol):
@@ -1067,20 +1067,20 @@ class _MultipartParserProtocol(protocol.Protocol):
     Protocol to read and parse a MSC3916 multipart/mixed response
     """
 
-    transport: Optional[ITCPTransport] = None
+    transport: ITCPTransport | None = None
 
     def __init__(
         self,
         stream: ByteWriteable,
         deferred: defer.Deferred,
         boundary: str,
-        max_length: Optional[int],
+        max_length: int | None,
     ) -> None:
         self.stream = stream
         self.deferred = deferred
         self.boundary = boundary
         self.max_length = max_length
-        self.parser: Optional[MultipartParser] = None
+        self.parser: MultipartParser | None = None
         self.multipart_response = MultipartResponse()
         self.has_redirect = False
         self.in_json = False
@@ -1175,10 +1175,10 @@ class _MultipartParserProtocol(protocol.Protocol):
 class _ReadBodyWithMaxSizeProtocol(protocol.Protocol):
     """A protocol which reads body to a stream, erroring if the body exceeds a maximum size."""
 
-    transport: Optional[ITCPTransport] = None
+    transport: ITCPTransport | None = None
 
     def __init__(
-        self, stream: ByteWriteable, deferred: defer.Deferred, max_size: Optional[int]
+        self, stream: ByteWriteable, deferred: defer.Deferred, max_size: int | None
     ):
         self.stream = stream
         self.deferred = deferred
@@ -1228,7 +1228,7 @@ class _ReadBodyWithMaxSizeProtocol(protocol.Protocol):
 
 
 def read_body_with_max_size(
-    response: IResponse, stream: ByteWriteable, max_size: Optional[int]
+    response: IResponse, stream: ByteWriteable, max_size: int | None
 ) -> "defer.Deferred[int]":
     """
     Read a HTTP response body to a file-object. Optionally enforcing a maximum file size.
@@ -1258,7 +1258,7 @@ def read_body_with_max_size(
 
 
 def read_multipart_response(
-    response: IResponse, stream: ByteWriteable, boundary: str, max_length: Optional[int]
+    response: IResponse, stream: ByteWriteable, boundary: str, max_length: int | None
 ) -> "defer.Deferred[MultipartResponse]":
     """
     Reads a MSC3916 multipart/mixed response and parses it, reading the file part (if it contains one) into
@@ -1283,7 +1283,7 @@ def read_multipart_response(
     return d
 
 
-def encode_query_args(args: Optional[QueryParams]) -> bytes:
+def encode_query_args(args: QueryParams | None) -> bytes:
     """
     Encodes a map of query arguments to bytes which can be appended to a URL.
 
@@ -1321,7 +1321,7 @@ class InsecureInterceptableContextFactory(ssl.ContextFactory):
 
 
 def is_unknown_endpoint(
-    e: HttpResponseException, synapse_error: Optional[SynapseError] = None
+    e: HttpResponseException, synapse_error: SynapseError | None = None
 ) -> bool:
     """
     Returns true if the response was due to an endpoint being unimplemented.
diff --git a/synapse/http/connectproxyclient.py b/synapse/http/connectproxyclient.py
index db803bc75a..094655f91a 100644
--- a/synapse/http/connectproxyclient.py
+++ b/synapse/http/connectproxyclient.py
@@ -22,7 +22,7 @@
 import abc
 import base64
 import logging
-from typing import Optional, Union
+from typing import Union
 
 import attr
 from zope.interface import implementer
@@ -106,7 +106,7 @@ class HTTPConnectProxyEndpoint:
         proxy_endpoint: IStreamClientEndpoint,
         host: bytes,
         port: int,
-        proxy_creds: Optional[ProxyCredentials],
+        proxy_creds: ProxyCredentials | None,
     ):
         self._reactor = reactor
         self._proxy_endpoint = proxy_endpoint
@@ -146,7 +146,7 @@ class HTTPProxiedClientFactory(protocol.ClientFactory):
         dst_host: bytes,
         dst_port: int,
         wrapped_factory: IProtocolFactory,
-        proxy_creds: Optional[ProxyCredentials],
+        proxy_creds: ProxyCredentials | None,
     ):
         self.dst_host = dst_host
         self.dst_port = dst_port
@@ -212,7 +212,7 @@ class HTTPConnectProtocol(protocol.Protocol):
         port: int,
         wrapped_protocol: IProtocol,
         connected_deferred: defer.Deferred,
-        proxy_creds: Optional[ProxyCredentials],
+        proxy_creds: ProxyCredentials | None,
     ):
         self.host = host
         self.port = port
@@ -275,7 +275,7 @@ class HTTPConnectSetupClient(http.HTTPClient):
         self,
         host: bytes,
         port: int,
-        proxy_creds: Optional[ProxyCredentials],
+        proxy_creds: ProxyCredentials | None,
     ):
         self.host = host
         self.port = port
diff --git a/synapse/http/federation/matrix_federation_agent.py b/synapse/http/federation/matrix_federation_agent.py
index 98826c9171..c3ba26fe03 100644
--- a/synapse/http/federation/matrix_federation_agent.py
+++ b/synapse/http/federation/matrix_federation_agent.py
@@ -19,7 +19,7 @@
 #
 import logging
 import urllib.parse
-from typing import Any, Generator, List, Optional
+from typing import Any, Generator
 from urllib.request import (  # type: ignore[attr-defined]
     proxy_bypass_environment,
 )
@@ -67,6 +67,9 @@ class MatrixFederationAgent:
     Args:
         reactor: twisted reactor to use for underlying requests
 
+        clock: Internal `HomeServer` clock used to track delayed and looping calls.
+            Should be obtained from `hs.get_clock()`.
+
         tls_client_options_factory:
             factory to use for fetching client tls options, or none to disable TLS.
 
@@ -97,18 +100,20 @@ class MatrixFederationAgent:
         *,
         server_name: str,
         reactor: ISynapseReactor,
-        tls_client_options_factory: Optional[FederationPolicyForHTTPS],
+        clock: Clock,
+        tls_client_options_factory: FederationPolicyForHTTPS | None,
         user_agent: bytes,
-        ip_allowlist: Optional[IPSet],
+        ip_allowlist: IPSet | None,
         ip_blocklist: IPSet,
-        proxy_config: Optional[ProxyConfig] = None,
-        _srv_resolver: Optional[SrvResolver] = None,
-        _well_known_resolver: Optional[WellKnownResolver] = None,
+        proxy_config: ProxyConfig | None = None,
+        _srv_resolver: SrvResolver | None = None,
+        _well_known_resolver: WellKnownResolver | None = None,
     ):
         """
         Args:
             server_name: Our homeserver name (used to label metrics) (`hs.hostname`).
             reactor
+            clock: Should be the `hs` clock from `hs.get_clock()`
             tls_client_options_factory
             user_agent
             ip_allowlist
@@ -124,7 +129,6 @@ class MatrixFederationAgent:
         # addresses, to prevent DNS rebinding.
         reactor = BlocklistingReactorWrapper(reactor, ip_allowlist, ip_blocklist)
 
-        self._clock = Clock(reactor, server_name=server_name)
         self._pool = HTTPConnectionPool(reactor)
         self._pool.retryAutomatically = False
         self._pool.maxPersistentPerHost = 5
@@ -147,6 +151,7 @@ class MatrixFederationAgent:
             _well_known_resolver = WellKnownResolver(
                 server_name=server_name,
                 reactor=reactor,
+                clock=clock,
                 agent=BlocklistingAgentWrapper(
                     ProxyAgent(
                         reactor=reactor,
@@ -167,8 +172,8 @@ class MatrixFederationAgent:
         self,
         method: bytes,
         uri: bytes,
-        headers: Optional[Headers] = None,
-        bodyProducer: Optional[IBodyProducer] = None,
+        headers: Headers | None = None,
+        bodyProducer: IBodyProducer | None = None,
     ) -> Generator[defer.Deferred, Any, IResponse]:
         """
         Args:
@@ -254,9 +259,9 @@ class MatrixHostnameEndpointFactory:
         *,
         reactor: IReactorCore,
         proxy_reactor: IReactorCore,
-        tls_client_options_factory: Optional[FederationPolicyForHTTPS],
-        srv_resolver: Optional[SrvResolver],
-        proxy_config: Optional[ProxyConfig],
+        tls_client_options_factory: FederationPolicyForHTTPS | None,
+        srv_resolver: SrvResolver | None,
+        proxy_config: ProxyConfig | None,
     ):
         self._reactor = reactor
         self._proxy_reactor = proxy_reactor
@@ -305,9 +310,9 @@ class MatrixHostnameEndpoint:
         *,
         reactor: IReactorCore,
         proxy_reactor: IReactorCore,
-        tls_client_options_factory: Optional[FederationPolicyForHTTPS],
+        tls_client_options_factory: FederationPolicyForHTTPS | None,
         srv_resolver: SrvResolver,
-        proxy_config: Optional[ProxyConfig],
+        proxy_config: ProxyConfig | None,
         parsed_uri: URI,
     ):
         self._reactor = reactor
@@ -408,7 +413,7 @@ class MatrixHostnameEndpoint:
         # to try and if that doesn't work then we'll have an exception.
         raise Exception("Failed to resolve server %r" % (self._parsed_uri.netloc,))
 
-    async def _resolve_server(self) -> List[Server]:
+    async def _resolve_server(self) -> list[Server]:
         """Resolves the server name to a list of hosts and ports to attempt to
         connect to.
         """
diff --git a/synapse/http/federation/srv_resolver.py b/synapse/http/federation/srv_resolver.py
index 639bf309d6..76a51e4873 100644
--- a/synapse/http/federation/srv_resolver.py
+++ b/synapse/http/federation/srv_resolver.py
@@ -22,7 +22,7 @@
 import logging
 import random
 import time
-from typing import Any, Callable, Dict, List
+from typing import Any, Callable
 
 import attr
 
@@ -34,7 +34,7 @@ from synapse.logging.context import make_deferred_yieldable
 
 logger = logging.getLogger(__name__)
 
-SERVER_CACHE: Dict[bytes, List["Server"]] = {}
+SERVER_CACHE: dict[bytes, list["Server"]] = {}
 
 
 @attr.s(auto_attribs=True, slots=True, frozen=True)
@@ -58,11 +58,11 @@ class Server:
     expires: int = 0
 
 
-def _sort_server_list(server_list: List[Server]) -> List[Server]:
+def _sort_server_list(server_list: list[Server]) -> list[Server]:
     """Given a list of SRV records sort them into priority order and shuffle
     each priority with the given weight.
     """
-    priority_map: Dict[int, List[Server]] = {}
+    priority_map: dict[int, list[Server]] = {}
 
     for server in server_list:
         priority_map.setdefault(server.priority, []).append(server)
@@ -116,14 +116,14 @@ class SrvResolver:
     def __init__(
         self,
         dns_client: Any = client,
-        cache: Dict[bytes, List[Server]] = SERVER_CACHE,
+        cache: dict[bytes, list[Server]] = SERVER_CACHE,
         get_time: Callable[[], float] = time.time,
     ):
         self._dns_client = dns_client
         self._cache = cache
         self._get_time = get_time
 
-    async def resolve_service(self, service_name: bytes) -> List[Server]:
+    async def resolve_service(self, service_name: bytes) -> list[Server]:
         """Look up a SRV record
 
         Args:
diff --git a/synapse/http/federation/well_known_resolver.py b/synapse/http/federation/well_known_resolver.py
index 97bba8231a..ec72e178c9 100644
--- a/synapse/http/federation/well_known_resolver.py
+++ b/synapse/http/federation/well_known_resolver.py
@@ -22,7 +22,7 @@ import logging
 import random
 import time
 from io import BytesIO
-from typing import Callable, Dict, Optional, Tuple
+from typing import Callable
 
 import attr
 
@@ -80,7 +80,7 @@ logger = logging.getLogger(__name__)
 
 @attr.s(slots=True, frozen=True, auto_attribs=True)
 class WellKnownLookupResult:
-    delegated_server: Optional[bytes]
+    delegated_server: bytes | None
 
 
 class WellKnownResolver:
@@ -90,15 +90,17 @@ class WellKnownResolver:
         self,
         server_name: str,
         reactor: ISynapseThreadlessReactor,
+        clock: Clock,
         agent: IAgent,
         user_agent: bytes,
-        well_known_cache: Optional[TTLCache[bytes, Optional[bytes]]] = None,
-        had_well_known_cache: Optional[TTLCache[bytes, bool]] = None,
+        well_known_cache: TTLCache[bytes, bytes | None] | None = None,
+        had_well_known_cache: TTLCache[bytes, bool] | None = None,
     ):
         """
         Args:
             server_name: Our homeserver name (used to label metrics) (`hs.hostname`).
             reactor
+            clock: Should be the `hs` clock from `hs.get_clock()`
             agent
             user_agent
             well_known_cache
@@ -107,7 +109,7 @@ class WellKnownResolver:
 
         self.server_name = server_name
         self._reactor = reactor
-        self._clock = Clock(reactor, server_name=server_name)
+        self._clock = clock
 
         if well_known_cache is None:
             well_known_cache = TTLCache(
@@ -154,7 +156,7 @@ class WellKnownResolver:
                 # label metrics)
                 server_name=self.server_name,
             ):
-                result: Optional[bytes]
+                result: bytes | None
                 cache_period: float
 
                 result, cache_period = await self._fetch_well_known(server_name)
@@ -186,7 +188,7 @@ class WellKnownResolver:
 
         return WellKnownLookupResult(delegated_server=result)
 
-    async def _fetch_well_known(self, server_name: bytes) -> Tuple[bytes, float]:
+    async def _fetch_well_known(self, server_name: bytes) -> tuple[bytes, float]:
         """Actually fetch and parse a .well-known, without checking the cache
 
         Args:
@@ -249,7 +251,7 @@ class WellKnownResolver:
 
     async def _make_well_known_request(
         self, server_name: bytes, retry: bool
-    ) -> Tuple[IResponse, bytes]:
+    ) -> tuple[IResponse, bytes]:
         """Make the well known request.
 
         This will retry the request if requested and it fails (with unable
@@ -318,7 +320,7 @@ class WellKnownResolver:
 
 def _cache_period_from_headers(
     headers: Headers, time_now: Callable[[], float] = time.time
-) -> Optional[float]:
+) -> float | None:
     cache_controls = _parse_cache_control(headers)
 
     if b"no-store" in cache_controls:
@@ -346,7 +348,7 @@ def _cache_period_from_headers(
     return None
 
 
-def _parse_cache_control(headers: Headers) -> Dict[bytes, Optional[bytes]]:
+def _parse_cache_control(headers: Headers) -> dict[bytes, bytes | None]:
     cache_controls = {}
     cache_control_headers = headers.getRawHeaders(b"cache-control") or []
     for hdr in cache_control_headers:
diff --git a/synapse/http/matrixfederationclient.py b/synapse/http/matrixfederationclient.py
index c264bae6e5..7090960cfb 100644
--- a/synapse/http/matrixfederationclient.py
+++ b/synapse/http/matrixfederationclient.py
@@ -31,15 +31,10 @@ from typing import (
     Any,
     BinaryIO,
     Callable,
-    Dict,
     Generic,
-    List,
     Literal,
-    Optional,
     TextIO,
-    Tuple,
     TypeVar,
-    Union,
     cast,
     overload,
 )
@@ -90,6 +85,7 @@ from synapse.logging.opentracing import set_tag, start_active_span, tags
 from synapse.metrics import SERVER_NAME_LABEL
 from synapse.types import JsonDict
 from synapse.util.async_helpers import AwakenableSleeper, Linearizer, timeout_deferred
+from synapse.util.clock import Clock
 from synapse.util.json import json_decoder
 from synapse.util.metrics import Measure
 from synapse.util.stringutils import parse_and_validate_server_name
@@ -155,15 +151,15 @@ class MatrixFederationRequest:
     """The remote server to send the HTTP request to.
     """
 
-    json: Optional[JsonDict] = None
+    json: JsonDict | None = None
     """JSON to send in the body.
     """
 
-    json_callback: Optional[Callable[[], JsonDict]] = None
+    json_callback: Callable[[], JsonDict] | None = None
     """A callback to generate the JSON.
     """
 
-    query: Optional[QueryParams] = None
+    query: QueryParams | None = None
     """Query arguments.
     """
 
@@ -206,7 +202,7 @@ class MatrixFederationRequest:
             )
             object.__setattr__(self, "uri", uri)
 
-    def get_json(self) -> Optional[JsonDict]:
+    def get_json(self) -> JsonDict | None:
         if self.json_callback:
             return self.json_callback()
         return self.json
@@ -218,7 +214,7 @@ class _BaseJsonParser(ByteParser[T]):
     CONTENT_TYPE = "application/json"
 
     def __init__(
-        self, validator: Optional[Callable[[Optional[object]], bool]] = None
+        self, validator: Callable[[object | None], bool] | None = None
     ) -> None:
         """
         Args:
@@ -252,7 +248,7 @@ class JsonParser(_BaseJsonParser[JsonDict]):
         return isinstance(v, dict)
 
 
-class LegacyJsonSendParser(_BaseJsonParser[Tuple[int, JsonDict]]):
+class LegacyJsonSendParser(_BaseJsonParser[tuple[int, JsonDict]]):
     """Ensure the legacy responses of /send_join & /send_leave are correct."""
 
     def __init__(self) -> None:
@@ -270,6 +266,7 @@ class LegacyJsonSendParser(_BaseJsonParser[Tuple[int, JsonDict]]):
 
 
 async def _handle_response(
+    clock: Clock,
     reactor: IReactorTime,
     timeout_sec: float,
     request: MatrixFederationRequest,
@@ -299,7 +296,11 @@ async def _handle_response(
         check_content_type_is(response.headers, parser.CONTENT_TYPE)
 
         d = read_body_with_max_size(response, parser, max_response_size)
-        d = timeout_deferred(d, timeout=timeout_sec, reactor=reactor)
+        d = timeout_deferred(
+            deferred=d,
+            timeout=timeout_sec,
+            clock=clock,
+        )
 
         length = await make_deferred_yieldable(d)
 
@@ -387,7 +388,7 @@ class BinaryIOWrapper:
         self.decoder = codecs.getincrementaldecoder(encoding)(errors)
         self.file = file
 
-    def write(self, b: Union[bytes, bytearray]) -> int:
+    def write(self, b: bytes | bytearray) -> int:
         self.file.write(self.decoder.decode(b))
         return len(b)
 
@@ -404,13 +405,14 @@ class MatrixFederationHttpClient:
     def __init__(
         self,
         hs: "HomeServer",
-        tls_client_options_factory: Optional[FederationPolicyForHTTPS],
+        tls_client_options_factory: FederationPolicyForHTTPS | None,
     ):
         self.hs = hs
         self.signing_key = hs.signing_key
         self.server_name = hs.hostname
 
         self.reactor = hs.get_reactor()
+        self.clock = hs.get_clock()
 
         user_agent = hs.version_string
         if hs.config.server.user_agent_suffix:
@@ -424,6 +426,7 @@ class MatrixFederationHttpClient:
             federation_agent: IAgent = MatrixFederationAgent(
                 server_name=self.server_name,
                 reactor=self.reactor,
+                clock=self.clock,
                 tls_client_options_factory=tls_client_options_factory,
                 user_agent=user_agent.encode("ascii"),
                 ip_allowlist=hs.config.server.federation_ip_range_allowlist,
@@ -457,7 +460,6 @@ class MatrixFederationHttpClient:
             ip_blocklist=hs.config.server.federation_ip_range_blocklist,
         )
 
-        self.clock = hs.get_clock()
         self._store = hs.get_datastores().main
         self.version_string_bytes = hs.version_string.encode("ascii")
         self.default_timeout_seconds = hs.config.federation.client_timeout_ms / 1000
@@ -470,9 +472,9 @@ class MatrixFederationHttpClient:
         self.max_long_retries = hs.config.federation.max_long_retries
         self.max_short_retries = hs.config.federation.max_short_retries
 
-        self._cooperator = Cooperator(scheduler=_make_scheduler(self.reactor))
+        self._cooperator = Cooperator(scheduler=_make_scheduler(self.clock))
 
-        self._sleeper = AwakenableSleeper(self.reactor)
+        self._sleeper = AwakenableSleeper(self.clock)
 
         self._simple_http_client = SimpleHttpClient(
             hs,
@@ -484,6 +486,10 @@ class MatrixFederationHttpClient:
         self.remote_download_linearizer = Linearizer(
             name="remote_download_linearizer", max_count=6, clock=self.clock
         )
+        self._is_shutdown = False
+
+    def shutdown(self) -> None:
+        self._is_shutdown = True
 
     def wake_destination(self, destination: str) -> None:
         """Called when the remote server may have come back online."""
@@ -542,7 +548,7 @@ class MatrixFederationHttpClient:
         self,
         request: MatrixFederationRequest,
         retry_on_dns_fail: bool = True,
-        timeout: Optional[int] = None,
+        timeout: int | None = None,
         long_retries: bool = False,
         ignore_backoff: bool = False,
         backoff_on_404: bool = False,
@@ -629,6 +635,7 @@ class MatrixFederationHttpClient:
         limiter = await synapse.util.retryutils.get_retry_limiter(
             destination=request.destination,
             our_server_name=self.server_name,
+            hs=self.hs,
             clock=self.clock,
             store=self._store,
             backoff_on_404=backoff_on_404,
@@ -655,7 +662,7 @@ class MatrixFederationHttpClient:
         )
 
         # Inject the span into the headers
-        headers_dict: Dict[bytes, List[bytes]] = {}
+        headers_dict: dict[bytes, list[bytes]] = {}
         opentracing.inject_header_dict(headers_dict, request.destination)
 
         headers_dict[b"User-Agent"] = [self.version_string_bytes]
@@ -675,7 +682,7 @@ class MatrixFederationHttpClient:
                 (b"", b"", path_bytes, None, query_bytes, b"")
             )
 
-            while True:
+            while not self._is_shutdown:
                 try:
                     json = request.get_json()
                     if json:
@@ -684,7 +691,7 @@ class MatrixFederationHttpClient:
                             destination_bytes, method_bytes, url_to_sign_bytes, json
                         )
                         data = encode_canonical_json(json)
-                        producer: Optional[IBodyProducer] = QuieterFileBodyProducer(
+                        producer: IBodyProducer | None = QuieterFileBodyProducer(
                             BytesIO(data), cooperator=self._cooperator
                         )
                     else:
@@ -733,9 +740,9 @@ class MatrixFederationHttpClient:
                                 bodyProducer=producer,
                             )
                             request_deferred = timeout_deferred(
-                                request_deferred,
+                                deferred=request_deferred,
                                 timeout=_sec_timeout,
-                                reactor=self.reactor,
+                                clock=self.clock,
                             )
 
                             response = await make_deferred_yieldable(request_deferred)
@@ -793,7 +800,9 @@ class MatrixFederationHttpClient:
                         # Update transactions table?
                         d = treq.content(response)
                         d = timeout_deferred(
-                            d, timeout=_sec_timeout, reactor=self.reactor
+                            deferred=d,
+                            timeout=_sec_timeout,
+                            clock=self.clock,
                         )
 
                         try:
@@ -862,6 +871,15 @@ class MatrixFederationHttpClient:
                             delay_seconds,
                         )
 
+                        if self._is_shutdown:
+                            # Immediately fail sending the request instead of starting a
+                            # potentially long sleep after the server has requested
+                            # shutdown.
+                            # This is the code path followed when the
+                            # `federation_transaction_transmission_loop` has been
+                            # cancelled.
+                            raise
+
                         # Sleep for the calculated delay, or wake up immediately
                         # if we get notified that the server is back up.
                         await self._sleeper.sleep(
@@ -885,12 +903,12 @@ class MatrixFederationHttpClient:
 
     def build_auth_headers(
         self,
-        destination: Optional[bytes],
+        destination: bytes | None,
         method: bytes,
         url_bytes: bytes,
-        content: Optional[JsonDict] = None,
-        destination_is: Optional[bytes] = None,
-    ) -> List[bytes]:
+        content: JsonDict | None = None,
+        destination_is: bytes | None = None,
+    ) -> list[bytes]:
         """
         Builds the Authorization headers for a federation request
         Args:
@@ -950,11 +968,11 @@ class MatrixFederationHttpClient:
         self,
         destination: str,
         path: str,
-        args: Optional[QueryParams] = None,
-        data: Optional[JsonDict] = None,
-        json_data_callback: Optional[Callable[[], JsonDict]] = None,
+        args: QueryParams | None = None,
+        data: JsonDict | None = None,
+        json_data_callback: Callable[[], JsonDict] | None = None,
         long_retries: bool = False,
-        timeout: Optional[int] = None,
+        timeout: int | None = None,
         ignore_backoff: bool = False,
         backoff_on_404: bool = False,
         try_trailing_slash_on_400: bool = False,
@@ -967,15 +985,15 @@ class MatrixFederationHttpClient:
         self,
         destination: str,
         path: str,
-        args: Optional[QueryParams] = None,
-        data: Optional[JsonDict] = None,
-        json_data_callback: Optional[Callable[[], JsonDict]] = None,
+        args: QueryParams | None = None,
+        data: JsonDict | None = None,
+        json_data_callback: Callable[[], JsonDict] | None = None,
         long_retries: bool = False,
-        timeout: Optional[int] = None,
+        timeout: int | None = None,
         ignore_backoff: bool = False,
         backoff_on_404: bool = False,
         try_trailing_slash_on_400: bool = False,
-        parser: Optional[ByteParser[T]] = None,
+        parser: ByteParser[T] | None = None,
         backoff_on_all_error_codes: bool = False,
     ) -> T: ...
 
@@ -983,17 +1001,17 @@ class MatrixFederationHttpClient:
         self,
         destination: str,
         path: str,
-        args: Optional[QueryParams] = None,
-        data: Optional[JsonDict] = None,
-        json_data_callback: Optional[Callable[[], JsonDict]] = None,
+        args: QueryParams | None = None,
+        data: JsonDict | None = None,
+        json_data_callback: Callable[[], JsonDict] | None = None,
         long_retries: bool = False,
-        timeout: Optional[int] = None,
+        timeout: int | None = None,
         ignore_backoff: bool = False,
         backoff_on_404: bool = False,
         try_trailing_slash_on_400: bool = False,
-        parser: Optional[ByteParser[T]] = None,
+        parser: ByteParser[T] | None = None,
         backoff_on_all_error_codes: bool = False,
-    ) -> Union[JsonDict, T]:
+    ) -> JsonDict | T:
         """Sends the specified json data using PUT
 
         Args:
@@ -1074,6 +1092,7 @@ class MatrixFederationHttpClient:
             parser = cast(ByteParser[T], JsonParser())
 
         body = await _handle_response(
+            self.clock,
             self.reactor,
             _sec_timeout,
             request,
@@ -1088,11 +1107,11 @@ class MatrixFederationHttpClient:
         self,
         destination: str,
         path: str,
-        data: Optional[JsonDict] = None,
+        data: JsonDict | None = None,
         long_retries: bool = False,
-        timeout: Optional[int] = None,
+        timeout: int | None = None,
         ignore_backoff: bool = False,
-        args: Optional[QueryParams] = None,
+        args: QueryParams | None = None,
     ) -> JsonDict:
         """Sends the specified json data using POST
 
@@ -1152,7 +1171,13 @@ class MatrixFederationHttpClient:
             _sec_timeout = self.default_timeout_seconds
 
         body = await _handle_response(
-            self.reactor, _sec_timeout, request, response, start_ms, parser=JsonParser()
+            self.clock,
+            self.reactor,
+            _sec_timeout,
+            request,
+            response,
+            start_ms,
+            parser=JsonParser(),
         )
         return body
 
@@ -1161,9 +1186,9 @@ class MatrixFederationHttpClient:
         self,
         destination: str,
         path: str,
-        args: Optional[QueryParams] = None,
+        args: QueryParams | None = None,
         retry_on_dns_fail: bool = True,
-        timeout: Optional[int] = None,
+        timeout: int | None = None,
         ignore_backoff: bool = False,
         try_trailing_slash_on_400: bool = False,
         parser: Literal[None] = None,
@@ -1174,9 +1199,9 @@ class MatrixFederationHttpClient:
         self,
         destination: str,
         path: str,
-        args: Optional[QueryParams] = ...,
+        args: QueryParams | None = ...,
         retry_on_dns_fail: bool = ...,
-        timeout: Optional[int] = ...,
+        timeout: int | None = ...,
         ignore_backoff: bool = ...,
         try_trailing_slash_on_400: bool = ...,
         parser: ByteParser[T] = ...,
@@ -1186,13 +1211,13 @@ class MatrixFederationHttpClient:
         self,
         destination: str,
         path: str,
-        args: Optional[QueryParams] = None,
+        args: QueryParams | None = None,
         retry_on_dns_fail: bool = True,
-        timeout: Optional[int] = None,
+        timeout: int | None = None,
         ignore_backoff: bool = False,
         try_trailing_slash_on_400: bool = False,
-        parser: Optional[ByteParser[T]] = None,
-    ) -> Union[JsonDict, T]:
+        parser: ByteParser[T] | None = None,
+    ) -> JsonDict | T:
         """GETs some json from the given host homeserver and path
 
         Args:
@@ -1255,38 +1280,38 @@ class MatrixFederationHttpClient:
         self,
         destination: str,
         path: str,
-        args: Optional[QueryParams] = None,
+        args: QueryParams | None = None,
         retry_on_dns_fail: bool = True,
-        timeout: Optional[int] = None,
+        timeout: int | None = None,
         ignore_backoff: bool = False,
         try_trailing_slash_on_400: bool = False,
         parser: Literal[None] = None,
-    ) -> Tuple[JsonDict, Dict[bytes, List[bytes]]]: ...
+    ) -> tuple[JsonDict, dict[bytes, list[bytes]]]: ...
 
     @overload
     async def get_json_with_headers(
         self,
         destination: str,
         path: str,
-        args: Optional[QueryParams] = ...,
+        args: QueryParams | None = ...,
         retry_on_dns_fail: bool = ...,
-        timeout: Optional[int] = ...,
+        timeout: int | None = ...,
         ignore_backoff: bool = ...,
         try_trailing_slash_on_400: bool = ...,
         parser: ByteParser[T] = ...,
-    ) -> Tuple[T, Dict[bytes, List[bytes]]]: ...
+    ) -> tuple[T, dict[bytes, list[bytes]]]: ...
 
     async def get_json_with_headers(
         self,
         destination: str,
         path: str,
-        args: Optional[QueryParams] = None,
+        args: QueryParams | None = None,
         retry_on_dns_fail: bool = True,
-        timeout: Optional[int] = None,
+        timeout: int | None = None,
         ignore_backoff: bool = False,
         try_trailing_slash_on_400: bool = False,
-        parser: Optional[ByteParser[T]] = None,
-    ) -> Tuple[Union[JsonDict, T], Dict[bytes, List[bytes]]]:
+        parser: ByteParser[T] | None = None,
+    ) -> tuple[JsonDict | T, dict[bytes, list[bytes]]]:
         """GETs some json from the given host homeserver and path
 
         Args:
@@ -1358,6 +1383,7 @@ class MatrixFederationHttpClient:
             parser = cast(ByteParser[T], JsonParser())
 
         body = await _handle_response(
+            self.clock,
             self.reactor,
             _sec_timeout,
             request,
@@ -1373,9 +1399,9 @@ class MatrixFederationHttpClient:
         destination: str,
         path: str,
         long_retries: bool = False,
-        timeout: Optional[int] = None,
+        timeout: int | None = None,
         ignore_backoff: bool = False,
-        args: Optional[QueryParams] = None,
+        args: QueryParams | None = None,
     ) -> JsonDict:
         """Send a DELETE request to the remote expecting some json response
 
@@ -1431,7 +1457,13 @@ class MatrixFederationHttpClient:
             _sec_timeout = self.default_timeout_seconds
 
         body = await _handle_response(
-            self.reactor, _sec_timeout, request, response, start_ms, parser=JsonParser()
+            self.clock,
+            self.reactor,
+            _sec_timeout,
+            request,
+            response,
+            start_ms,
+            parser=JsonParser(),
         )
         return body
 
@@ -1443,11 +1475,11 @@ class MatrixFederationHttpClient:
         download_ratelimiter: Ratelimiter,
         ip_address: str,
         max_size: int,
-        args: Optional[QueryParams] = None,
+        args: QueryParams | None = None,
         retry_on_dns_fail: bool = True,
         ignore_backoff: bool = False,
         follow_redirects: bool = False,
-    ) -> Tuple[int, Dict[bytes, List[bytes]]]:
+    ) -> tuple[int, dict[bytes, list[bytes]]]:
         """GETs a file from a given homeserver
         Args:
             destination: The remote server to send the HTTP request to.
@@ -1605,10 +1637,10 @@ class MatrixFederationHttpClient:
         download_ratelimiter: Ratelimiter,
         ip_address: str,
         max_size: int,
-        args: Optional[QueryParams] = None,
+        args: QueryParams | None = None,
         retry_on_dns_fail: bool = True,
         ignore_backoff: bool = False,
-    ) -> Tuple[int, Dict[bytes, List[bytes]], bytes]:
+    ) -> tuple[int, dict[bytes, list[bytes]], bytes]:
         """GETs a file from a given homeserver over the federation /download endpoint
         Args:
             destination: The remote server to send the HTTP request to.
@@ -1721,6 +1753,7 @@ class MatrixFederationHttpClient:
                     response, output_stream, boundary, expected_size + 1
                 )
                 deferred.addTimeout(self.default_timeout_seconds, self.reactor)
+                multipart_response = await make_deferred_yieldable(deferred)
         except BodyExceededMaxSize:
             msg = "Requested file is too large > %r bytes" % (expected_size,)
             logger.warning(
@@ -1757,7 +1790,6 @@ class MatrixFederationHttpClient:
             )
             raise
 
-        multipart_response = await make_deferred_yieldable(deferred)
         if not multipart_response.url:
             assert multipart_response.length is not None
             length = multipart_response.length
diff --git a/synapse/http/proxy.py b/synapse/http/proxy.py
index 9b044f3b0a..c7f5e39dd8 100644
--- a/synapse/http/proxy.py
+++ b/synapse/http/proxy.py
@@ -22,7 +22,7 @@
 import json
 import logging
 import urllib.parse
-from typing import TYPE_CHECKING, Any, Optional, Set, Tuple, cast
+from typing import TYPE_CHECKING, Any, cast
 
 from twisted.internet import protocol
 from twisted.internet.interfaces import ITCPTransport
@@ -65,8 +65,8 @@ assert all(header.lower() == header for header in HOP_BY_HOP_HEADERS_LOWERCASE)
 
 
 def parse_connection_header_value(
-    connection_header_value: Optional[bytes],
-) -> Set[str]:
+    connection_header_value: bytes | None,
+) -> set[str]:
     """
     Parse the `Connection` header to determine which headers we should not be copied
     over from the remote response.
@@ -86,7 +86,7 @@ def parse_connection_header_value(
         The set of header names that should not be copied over from the remote response.
         The keys are lowercased.
     """
-    extra_headers_to_remove: Set[str] = set()
+    extra_headers_to_remove: set[str] = set()
     if connection_header_value:
         extra_headers_to_remove = {
             connection_option.decode("ascii").strip().lower()
@@ -140,7 +140,7 @@ class ProxyResource(_AsyncResource):
             "Invalid Proxy-Authorization header.", Codes.UNAUTHORIZED
         )
 
-    async def _async_render(self, request: "SynapseRequest") -> Tuple[int, Any]:
+    async def _async_render(self, request: "SynapseRequest") -> tuple[int, Any]:
         uri = urllib.parse.urlparse(request.uri)
         assert uri.scheme == b"matrix-federation"
 
@@ -161,12 +161,12 @@ class ProxyResource(_AsyncResource):
             bodyProducer=QuieterFileBodyProducer(request.content),
         )
         request_deferred = timeout_deferred(
-            request_deferred,
+            deferred=request_deferred,
             # This should be set longer than the timeout in `MatrixFederationHttpClient`
             # so that it has enough time to complete and pass us the data before we give
             # up.
             timeout=90,
-            reactor=self.reactor,
+            clock=self._clock,
         )
 
         response = await make_deferred_yieldable(request_deferred)
@@ -237,7 +237,7 @@ class _ProxyResponseBody(protocol.Protocol):
     request.
     """
 
-    transport: Optional[ITCPTransport] = None
+    transport: ITCPTransport | None = None
 
     def __init__(self, request: "SynapseRequest") -> None:
         self._request = request
diff --git a/synapse/http/proxyagent.py b/synapse/http/proxyagent.py
index ab413990c5..d315ce8475 100644
--- a/synapse/http/proxyagent.py
+++ b/synapse/http/proxyagent.py
@@ -21,7 +21,7 @@
 import logging
 import random
 import re
-from typing import Any, Collection, Dict, List, Optional, Sequence, Tuple, Union, cast
+from typing import Any, Collection, Sequence, cast
 from urllib.parse import urlparse
 from urllib.request import (  # type: ignore[attr-defined]
     proxy_bypass_environment,
@@ -119,14 +119,14 @@ class ProxyAgent(_AgentBase):
         self,
         *,
         reactor: IReactorCore,
-        proxy_reactor: Optional[IReactorCore] = None,
-        contextFactory: Optional[IPolicyForHTTPS] = None,
-        connectTimeout: Optional[float] = None,
-        bindAddress: Optional[bytes] = None,
-        pool: Optional[HTTPConnectionPool] = None,
-        proxy_config: Optional[ProxyConfig] = None,
+        proxy_reactor: IReactorCore | None = None,
+        contextFactory: IPolicyForHTTPS | None = None,
+        connectTimeout: float | None = None,
+        bindAddress: bytes | None = None,
+        pool: HTTPConnectionPool | None = None,
+        proxy_config: ProxyConfig | None = None,
         federation_proxy_locations: Collection[InstanceLocationConfig] = (),
-        federation_proxy_credentials: Optional[ProxyCredentials] = None,
+        federation_proxy_credentials: ProxyCredentials | None = None,
     ):
         contextFactory = contextFactory or BrowserLikePolicyForHTTPS()
 
@@ -139,7 +139,7 @@ class ProxyAgent(_AgentBase):
         else:
             self.proxy_reactor = proxy_reactor
 
-        self._endpoint_kwargs: Dict[str, Any] = {}
+        self._endpoint_kwargs: dict[str, Any] = {}
         if connectTimeout is not None:
             self._endpoint_kwargs["timeout"] = connectTimeout
         if bindAddress is not None:
@@ -175,14 +175,14 @@ class ProxyAgent(_AgentBase):
         self._policy_for_https = contextFactory
         self._reactor = cast(IReactorTime, reactor)
 
-        self._federation_proxy_endpoint: Optional[IStreamClientEndpoint] = None
-        self._federation_proxy_credentials: Optional[ProxyCredentials] = None
+        self._federation_proxy_endpoint: IStreamClientEndpoint | None = None
+        self._federation_proxy_credentials: ProxyCredentials | None = None
         if federation_proxy_locations:
             assert federation_proxy_credentials is not None, (
                 "`federation_proxy_credentials` are required when using `federation_proxy_locations`"
             )
 
-            endpoints: List[IStreamClientEndpoint] = []
+            endpoints: list[IStreamClientEndpoint] = []
             for federation_proxy_location in federation_proxy_locations:
                 endpoint: IStreamClientEndpoint
                 if isinstance(federation_proxy_location, InstanceTcpLocationConfig):
@@ -220,8 +220,8 @@ class ProxyAgent(_AgentBase):
         self,
         method: bytes,
         uri: bytes,
-        headers: Optional[Headers] = None,
-        bodyProducer: Optional[IBodyProducer] = None,
+        headers: Headers | None = None,
+        bodyProducer: IBodyProducer | None = None,
     ) -> "defer.Deferred[IResponse]":
         """
         Issue a request to the server indicated by the given uri.
@@ -363,13 +363,13 @@ class ProxyAgent(_AgentBase):
 
 
 def http_proxy_endpoint(
-    proxy: Optional[bytes],
+    proxy: bytes | None,
     reactor: IReactorCore,
-    tls_options_factory: Optional[IPolicyForHTTPS],
+    tls_options_factory: IPolicyForHTTPS | None,
     timeout: float = 30,
-    bindAddress: Optional[Union[bytes, str, tuple[Union[bytes, str], int]]] = None,
-    attemptDelay: Optional[float] = None,
-) -> Tuple[Optional[IStreamClientEndpoint], Optional[ProxyCredentials]]:
+    bindAddress: bytes | str | tuple[bytes | str, int] | None = None,
+    attemptDelay: float | None = None,
+) -> tuple[IStreamClientEndpoint | None, ProxyCredentials | None]:
     """Parses an http proxy setting and returns an endpoint for the proxy
 
     Args:
@@ -418,7 +418,7 @@ def http_proxy_endpoint(
 
 def parse_proxy(
     proxy: bytes, default_scheme: bytes = b"http", default_port: int = 1080
-) -> Tuple[bytes, bytes, int, Optional[ProxyCredentials]]:
+) -> tuple[bytes, bytes, int, ProxyCredentials | None]:
     """
     Parse a proxy connection string.
 
@@ -487,7 +487,7 @@ class _RandomSampleEndpoints:
         return run_in_background(self._do_connect, protocol_factory)
 
     async def _do_connect(self, protocol_factory: IProtocolFactory) -> IProtocol:
-        failures: List[Failure] = []
+        failures: list[Failure] = []
         for endpoint in random.sample(self._endpoints, k=len(self._endpoints)):
             try:
                 return await endpoint.connect(protocol_factory)
diff --git a/synapse/http/replicationagent.py b/synapse/http/replicationagent.py
index d70575dbd5..708e4c386b 100644
--- a/synapse/http/replicationagent.py
+++ b/synapse/http/replicationagent.py
@@ -20,7 +20,6 @@
 #
 
 import logging
-from typing import Dict, Optional
 
 from zope.interface import implementer
 
@@ -60,7 +59,7 @@ class ReplicationEndpointFactory:
     def __init__(
         self,
         reactor: ISynapseReactor,
-        instance_map: Dict[str, InstanceLocationConfig],
+        instance_map: dict[str, InstanceLocationConfig],
         context_factory: IPolicyForHTTPS,
     ) -> None:
         self.reactor = reactor
@@ -117,11 +116,11 @@ class ReplicationAgent(_AgentBase):
     def __init__(
         self,
         reactor: ISynapseReactor,
-        instance_map: Dict[str, InstanceLocationConfig],
+        instance_map: dict[str, InstanceLocationConfig],
         contextFactory: IPolicyForHTTPS,
-        connectTimeout: Optional[float] = None,
-        bindAddress: Optional[bytes] = None,
-        pool: Optional[HTTPConnectionPool] = None,
+        connectTimeout: float | None = None,
+        bindAddress: bytes | None = None,
+        pool: HTTPConnectionPool | None = None,
     ):
         """
         Create a ReplicationAgent.
@@ -149,8 +148,8 @@ class ReplicationAgent(_AgentBase):
         self,
         method: bytes,
         uri: bytes,
-        headers: Optional[Headers] = None,
-        bodyProducer: Optional[IBodyProducer] = None,
+        headers: Headers | None = None,
+        bodyProducer: IBodyProducer | None = None,
     ) -> "defer.Deferred[IResponse]":
         """
         Issue a request to the server indicated by the given uri.
diff --git a/synapse/http/request_metrics.py b/synapse/http/request_metrics.py
index 83f52edb7c..5cc8a2ebd8 100644
--- a/synapse/http/request_metrics.py
+++ b/synapse/http/request_metrics.py
@@ -22,7 +22,7 @@
 import logging
 import threading
 import traceback
-from typing import Dict, Mapping, Set, Tuple
+from typing import Mapping
 
 from prometheus_client.core import Counter, Histogram
 
@@ -133,13 +133,13 @@ in_flight_requests_db_sched_duration = Counter(
     labelnames=["method", "servlet", SERVER_NAME_LABEL],
 )
 
-_in_flight_requests: Set["RequestMetrics"] = set()
+_in_flight_requests: set["RequestMetrics"] = set()
 
 # Protects the _in_flight_requests set from concurrent access
 _in_flight_requests_lock = threading.Lock()
 
 
-def _get_in_flight_counts() -> Mapping[Tuple[str, ...], int]:
+def _get_in_flight_counts() -> Mapping[tuple[str, ...], int]:
     """Returns a count of all in flight requests by (method, server_name)"""
     # Cast to a list to prevent it changing while the Prometheus
     # thread is collecting metrics
@@ -152,7 +152,7 @@ def _get_in_flight_counts() -> Mapping[Tuple[str, ...], int]:
     # Map from (method, name) -> int, the number of in flight requests of that
     # type. The key type is Tuple[str, str], but we leave the length unspecified
     # for compatability with LaterGauge's annotations.
-    counts: Dict[Tuple[str, ...], int] = {}
+    counts: dict[tuple[str, ...], int] = {}
     for request_metric in request_metrics:
         key = (
             request_metric.method,
diff --git a/synapse/http/server.py b/synapse/http/server.py
index ce9d5630df..5f4e7484fd 100644
--- a/synapse/http/server.py
+++ b/synapse/http/server.py
@@ -33,15 +33,10 @@ from typing import (
     Any,
     Awaitable,
     Callable,
-    Dict,
     Iterable,
     Iterator,
-    List,
-    Optional,
     Pattern,
     Protocol,
-    Tuple,
-    Union,
     cast,
 )
 
@@ -114,7 +109,7 @@ HTTP_STATUS_REQUEST_CANCELLED = 499
 
 
 def return_json_error(
-    f: failure.Failure, request: "SynapseRequest", config: Optional[HomeServerConfig]
+    f: failure.Failure, request: "SynapseRequest", config: HomeServerConfig | None
 ) -> None:
     """Sends a JSON error response to clients."""
 
@@ -176,7 +171,7 @@ def return_json_error(
 def return_html_error(
     f: failure.Failure,
     request: Request,
-    error_template: Union[str, jinja2.Template],
+    error_template: str | jinja2.Template,
 ) -> None:
     """Sends an HTML error page corresponding to the given failure.
 
@@ -267,7 +262,7 @@ def wrap_async_request_handler(
 # it is actually called with a SynapseRequest and a kwargs dict for the params,
 # but I can't figure out how to represent that.
 ServletCallback = Callable[
-    ..., Union[None, Awaitable[None], Tuple[int, Any], Awaitable[Tuple[int, Any]]]
+    ..., None | Awaitable[None] | tuple[int, Any] | Awaitable[tuple[int, Any]]
 ]
 
 
@@ -352,9 +347,7 @@ class _AsyncResource(resource.Resource, metaclass=abc.ABCMeta):
             f = failure.Failure()
             self._send_error_response(f, request)
 
-    async def _async_render(
-        self, request: "SynapseRequest"
-    ) -> Optional[Tuple[int, Any]]:
+    async def _async_render(self, request: "SynapseRequest") -> tuple[int, Any] | None:
         """Delegates to `_async_render_<METHOD>` methods, or returns a 400 if
         no appropriate method exists. Can be overridden in sub classes for
         different routing.
@@ -409,7 +402,7 @@ class DirectServeJsonResource(_AsyncResource):
         canonical_json: bool = False,
         extract_context: bool = False,
         # Clock is optional as this class is exposed to the module API.
-        clock: Optional[Clock] = None,
+        clock: Clock | None = None,
     ):
         """
         Args:
@@ -420,7 +413,14 @@ class DirectServeJsonResource(_AsyncResource):
         """
 
         if clock is None:
-            clock = Clock(
+            # Ideally we wouldn't ignore the linter error here and instead enforce a
+            # required `Clock` be passed into the `__init__` function.
+            # However, this would change the function signature which is currently being
+            # exported to the module api. Since we don't want to break that api, we have
+            # to settle with ignoring the linter error here.
+            # As of the time of writing this, all Synapse internal usages of
+            # `DirectServeJsonResource` pass in the existing homeserver clock instance.
+            clock = Clock(  # type: ignore[multiple-internal-clocks]
                 cast(ISynapseThreadlessReactor, reactor),
                 server_name="synapse_module_running_from_unknown_server",
             )
@@ -484,7 +484,7 @@ class JsonResource(DirectServeJsonResource):
         self.clock = hs.get_clock()
         super().__init__(canonical_json, extract_context, clock=self.clock)
         # Map of path regex -> method -> callback.
-        self._routes: Dict[Pattern[str], Dict[bytes, _PathEntry]] = {}
+        self._routes: dict[Pattern[str], dict[bytes, _PathEntry]] = {}
         self.hs = hs
 
     def register_paths(
@@ -520,7 +520,7 @@ class JsonResource(DirectServeJsonResource):
 
     def _get_handler_for_request(
         self, request: "SynapseRequest"
-    ) -> Tuple[ServletCallback, str, Dict[str, str]]:
+    ) -> tuple[ServletCallback, str, dict[str, str]]:
         """Finds a callback method to handle the given request.
 
         Returns:
@@ -549,7 +549,7 @@ class JsonResource(DirectServeJsonResource):
         # Huh. No one wanted to handle that? Fiiiiiine.
         raise UnrecognizedRequestError(code=404)
 
-    async def _async_render(self, request: "SynapseRequest") -> Tuple[int, Any]:
+    async def _async_render(self, request: "SynapseRequest") -> tuple[int, Any]:
         callback, servlet_classname, group_dict = self._get_handler_for_request(request)
 
         request.is_render_cancellable = is_function_cancellable(callback)
@@ -599,7 +599,7 @@ class DirectServeHtmlResource(_AsyncResource):
         self,
         extract_context: bool = False,
         # Clock is optional as this class is exposed to the module API.
-        clock: Optional[Clock] = None,
+        clock: Clock | None = None,
     ):
         """
         Args:
@@ -608,7 +608,14 @@ class DirectServeHtmlResource(_AsyncResource):
                 Only optional for the Module API.
         """
         if clock is None:
-            clock = Clock(
+            # Ideally we wouldn't ignore the linter error here and instead enforce a
+            # required `Clock` be passed into the `__init__` function.
+            # However, this would change the function signature which is currently being
+            # exported to the module api. Since we don't want to break that api, we have
+            # to settle with ignoring the linter error here.
+            # As of the time of writing this, all Synapse internal usages of
+            # `DirectServeHtmlResource` pass in the existing homeserver clock instance.
+            clock = Clock(  # type: ignore[multiple-internal-clocks]
                 cast(ISynapseThreadlessReactor, reactor),
                 server_name="synapse_module_running_from_unknown_server",
             )
@@ -721,7 +728,7 @@ class _ByteProducer:
         request: Request,
         iterator: Iterator[bytes],
     ):
-        self._request: Optional[Request] = request
+        self._request: Request | None = request
         self._iterator = iterator
         self._paused = False
         self.tracing_scope = start_active_span(
@@ -744,7 +751,7 @@ class _ByteProducer:
             # Start producing if `registerProducer` was successful
             self.resumeProducing()
 
-    def _send_data(self, data: List[bytes]) -> None:
+    def _send_data(self, data: list[bytes]) -> None:
         """
         Send a list of bytes as a chunk of a response.
         """
@@ -820,7 +827,7 @@ def respond_with_json(
     json_object: Any,
     send_cors: bool = False,
     canonical_json: bool = True,
-) -> Optional[int]:
+) -> int | None:
     """Sends encoded JSON in response to the given request.
 
     Args:
@@ -869,7 +876,7 @@ def respond_with_json_bytes(
     code: int,
     json_bytes: bytes,
     send_cors: bool = False,
-) -> Optional[int]:
+) -> int | None:
     """Sends encoded JSON in response to the given request.
 
     Args:
@@ -918,7 +925,7 @@ async def _async_write_json_to_request_in_thread(
     expensive.
     """
 
-    def encode(opentracing_span: "Optional[opentracing.Span]") -> bytes:
+    def encode(opentracing_span: "opentracing.Span | None") -> bytes:
         # it might take a while for the threadpool to schedule us, so we write
         # opentracing logs once we actually get scheduled, so that we can see how
         # much that contributed.
diff --git a/synapse/http/servlet.py b/synapse/http/servlet.py
index 71e809b3f1..c182497f2d 100644
--- a/synapse/http/servlet.py
+++ b/synapse/http/servlet.py
@@ -27,26 +27,17 @@ import urllib.parse as urlparse
 from http import HTTPStatus
 from typing import (
     TYPE_CHECKING,
-    List,
     Literal,
     Mapping,
-    Optional,
     Sequence,
-    Tuple,
-    Type,
     TypeVar,
     overload,
 )
 
+from pydantic import BaseModel, ValidationError
+
 from twisted.web.server import Request
 
-from synapse._pydantic_compat import (
-    BaseModel,
-    ErrorWrapper,
-    MissingError,
-    PydanticValueError,
-    ValidationError,
-)
 from synapse.api.errors import Codes, SynapseError
 from synapse.http import redact_uri
 from synapse.http.server import HttpServer
@@ -88,26 +79,26 @@ def parse_integer(
 
 
 @overload
-def parse_integer(request: Request, name: str, *, negative: bool) -> Optional[int]: ...
+def parse_integer(request: Request, name: str, *, negative: bool) -> int | None: ...
 
 
 @overload
 def parse_integer(
     request: Request,
     name: str,
-    default: Optional[int] = None,
+    default: int | None = None,
     required: bool = False,
     negative: bool = False,
-) -> Optional[int]: ...
+) -> int | None: ...
 
 
 def parse_integer(
     request: Request,
     name: str,
-    default: Optional[int] = None,
+    default: int | None = None,
     required: bool = False,
     negative: bool = False,
-) -> Optional[int]:
+) -> int | None:
     """Parse an integer parameter from the request string
 
     Args:
@@ -144,8 +135,8 @@ def parse_integer_from_args(
 def parse_integer_from_args(
     args: Mapping[bytes, Sequence[bytes]],
     name: str,
-    default: Optional[int] = None,
-) -> Optional[int]: ...
+    default: int | None = None,
+) -> int | None: ...
 
 
 @overload
@@ -161,19 +152,19 @@ def parse_integer_from_args(
 def parse_integer_from_args(
     args: Mapping[bytes, Sequence[bytes]],
     name: str,
-    default: Optional[int] = None,
+    default: int | None = None,
     required: bool = False,
     negative: bool = False,
-) -> Optional[int]: ...
+) -> int | None: ...
 
 
 def parse_integer_from_args(
     args: Mapping[bytes, Sequence[bytes]],
     name: str,
-    default: Optional[int] = None,
+    default: int | None = None,
     required: bool = False,
     negative: bool = False,
-) -> Optional[int]:
+) -> int | None:
     """Parse an integer parameter from the request string
 
     Args:
@@ -225,13 +216,13 @@ def parse_boolean(request: Request, name: str, *, required: Literal[True]) -> bo
 
 @overload
 def parse_boolean(
-    request: Request, name: str, default: Optional[bool] = None, required: bool = False
-) -> Optional[bool]: ...
+    request: Request, name: str, default: bool | None = None, required: bool = False
+) -> bool | None: ...
 
 
 def parse_boolean(
-    request: Request, name: str, default: Optional[bool] = None, required: bool = False
-) -> Optional[bool]:
+    request: Request, name: str, default: bool | None = None, required: bool = False
+) -> bool | None:
     """Parse a boolean parameter from the request query string
 
     Args:
@@ -273,17 +264,17 @@ def parse_boolean_from_args(
 def parse_boolean_from_args(
     args: Mapping[bytes, Sequence[bytes]],
     name: str,
-    default: Optional[bool] = None,
+    default: bool | None = None,
     required: bool = False,
-) -> Optional[bool]: ...
+) -> bool | None: ...
 
 
 def parse_boolean_from_args(
     args: Mapping[bytes, Sequence[bytes]],
     name: str,
-    default: Optional[bool] = None,
+    default: bool | None = None,
     required: bool = False,
-) -> Optional[bool]:
+) -> bool | None:
     """Parse a boolean parameter from the request query string
 
     Args:
@@ -326,8 +317,8 @@ def parse_boolean_from_args(
 def parse_bytes_from_args(
     args: Mapping[bytes, Sequence[bytes]],
     name: str,
-    default: Optional[bytes] = None,
-) -> Optional[bytes]: ...
+    default: bytes | None = None,
+) -> bytes | None: ...
 
 
 @overload
@@ -344,17 +335,17 @@ def parse_bytes_from_args(
 def parse_bytes_from_args(
     args: Mapping[bytes, Sequence[bytes]],
     name: str,
-    default: Optional[bytes] = None,
+    default: bytes | None = None,
     required: bool = False,
-) -> Optional[bytes]: ...
+) -> bytes | None: ...
 
 
 def parse_bytes_from_args(
     args: Mapping[bytes, Sequence[bytes]],
     name: str,
-    default: Optional[bytes] = None,
+    default: bytes | None = None,
     required: bool = False,
-) -> Optional[bytes]:
+) -> bytes | None:
     """
     Parse a string parameter as bytes from the request query string.
 
@@ -388,7 +379,7 @@ def parse_string(
     name: str,
     default: str,
     *,
-    allowed_values: Optional[StrCollection] = None,
+    allowed_values: StrCollection | None = None,
     encoding: str = "ascii",
 ) -> str: ...
 
@@ -399,7 +390,7 @@ def parse_string(
     name: str,
     *,
     required: Literal[True],
-    allowed_values: Optional[StrCollection] = None,
+    allowed_values: StrCollection | None = None,
     encoding: str = "ascii",
 ) -> str: ...
 
@@ -409,21 +400,21 @@ def parse_string(
     request: Request,
     name: str,
     *,
-    default: Optional[str] = None,
+    default: str | None = None,
     required: bool = False,
-    allowed_values: Optional[StrCollection] = None,
+    allowed_values: StrCollection | None = None,
     encoding: str = "ascii",
-) -> Optional[str]: ...
+) -> str | None: ...
 
 
 def parse_string(
     request: Request,
     name: str,
-    default: Optional[str] = None,
+    default: str | None = None,
     required: bool = False,
-    allowed_values: Optional[StrCollection] = None,
+    allowed_values: StrCollection | None = None,
     encoding: str = "ascii",
-) -> Optional[str]:
+) -> str | None:
     """
     Parse a string parameter from the request query string.
 
@@ -463,10 +454,10 @@ def parse_string(
 def parse_json(
     request: Request,
     name: str,
-    default: Optional[dict] = None,
+    default: dict | None = None,
     required: bool = False,
     encoding: str = "ascii",
-) -> Optional[JsonDict]:
+) -> JsonDict | None:
     """
     Parse a JSON parameter from the request query string.
 
@@ -500,10 +491,10 @@ def parse_json(
 def parse_json_from_args(
     args: Mapping[bytes, Sequence[bytes]],
     name: str,
-    default: Optional[dict] = None,
+    default: dict | None = None,
     required: bool = False,
     encoding: str = "ascii",
-) -> Optional[JsonDict]:
+) -> JsonDict | None:
     """
     Parse a JSON parameter from the request query string.
 
@@ -548,7 +539,7 @@ EnumT = TypeVar("EnumT", bound=enum.Enum)
 def parse_enum(
     request: Request,
     name: str,
-    E: Type[EnumT],
+    E: type[EnumT],
     default: EnumT,
 ) -> EnumT: ...
 
@@ -557,7 +548,7 @@ def parse_enum(
 def parse_enum(
     request: Request,
     name: str,
-    E: Type[EnumT],
+    E: type[EnumT],
     *,
     required: Literal[True],
 ) -> EnumT: ...
@@ -566,10 +557,10 @@ def parse_enum(
 def parse_enum(
     request: Request,
     name: str,
-    E: Type[EnumT],
-    default: Optional[EnumT] = None,
+    E: type[EnumT],
+    default: EnumT | None = None,
     required: bool = False,
-) -> Optional[EnumT]:
+) -> EnumT | None:
     """
     Parse an enum parameter from the request query string.
 
@@ -609,7 +600,7 @@ def parse_enum(
 
 def _parse_string_value(
     value: bytes,
-    allowed_values: Optional[StrCollection],
+    allowed_values: StrCollection | None,
     name: str,
     encoding: str,
 ) -> str:
@@ -635,20 +626,20 @@ def parse_strings_from_args(
     args: Mapping[bytes, Sequence[bytes]],
     name: str,
     *,
-    allowed_values: Optional[StrCollection] = None,
+    allowed_values: StrCollection | None = None,
     encoding: str = "ascii",
-) -> Optional[List[str]]: ...
+) -> list[str] | None: ...
 
 
 @overload
 def parse_strings_from_args(
     args: Mapping[bytes, Sequence[bytes]],
     name: str,
-    default: List[str],
+    default: list[str],
     *,
-    allowed_values: Optional[StrCollection] = None,
+    allowed_values: StrCollection | None = None,
     encoding: str = "ascii",
-) -> List[str]: ...
+) -> list[str]: ...
 
 
 @overload
@@ -657,31 +648,31 @@ def parse_strings_from_args(
     name: str,
     *,
     required: Literal[True],
-    allowed_values: Optional[StrCollection] = None,
+    allowed_values: StrCollection | None = None,
     encoding: str = "ascii",
-) -> List[str]: ...
+) -> list[str]: ...
 
 
 @overload
 def parse_strings_from_args(
     args: Mapping[bytes, Sequence[bytes]],
     name: str,
-    default: Optional[List[str]] = None,
+    default: list[str] | None = None,
     *,
     required: bool = False,
-    allowed_values: Optional[StrCollection] = None,
+    allowed_values: StrCollection | None = None,
     encoding: str = "ascii",
-) -> Optional[List[str]]: ...
+) -> list[str] | None: ...
 
 
 def parse_strings_from_args(
     args: Mapping[bytes, Sequence[bytes]],
     name: str,
-    default: Optional[List[str]] = None,
+    default: list[str] | None = None,
     required: bool = False,
-    allowed_values: Optional[StrCollection] = None,
+    allowed_values: StrCollection | None = None,
     encoding: str = "ascii",
-) -> Optional[List[str]]:
+) -> list[str] | None:
     """
     Parse a string parameter from the request query string list.
 
@@ -728,21 +719,21 @@ def parse_strings_from_args(
 def parse_string_from_args(
     args: Mapping[bytes, Sequence[bytes]],
     name: str,
-    default: Optional[str] = None,
+    default: str | None = None,
     *,
-    allowed_values: Optional[StrCollection] = None,
+    allowed_values: StrCollection | None = None,
     encoding: str = "ascii",
-) -> Optional[str]: ...
+) -> str | None: ...
 
 
 @overload
 def parse_string_from_args(
     args: Mapping[bytes, Sequence[bytes]],
     name: str,
-    default: Optional[str] = None,
+    default: str | None = None,
     *,
     required: Literal[True],
-    allowed_values: Optional[StrCollection] = None,
+    allowed_values: StrCollection | None = None,
     encoding: str = "ascii",
 ) -> str: ...
 
@@ -751,21 +742,21 @@ def parse_string_from_args(
 def parse_string_from_args(
     args: Mapping[bytes, Sequence[bytes]],
     name: str,
-    default: Optional[str] = None,
+    default: str | None = None,
     required: bool = False,
-    allowed_values: Optional[StrCollection] = None,
+    allowed_values: StrCollection | None = None,
     encoding: str = "ascii",
-) -> Optional[str]: ...
+) -> str | None: ...
 
 
 def parse_string_from_args(
     args: Mapping[bytes, Sequence[bytes]],
     name: str,
-    default: Optional[str] = None,
+    default: str | None = None,
     required: bool = False,
-    allowed_values: Optional[StrCollection] = None,
+    allowed_values: StrCollection | None = None,
     encoding: str = "ascii",
-) -> Optional[str]:
+) -> str | None:
     """
     Parse the string parameter from the request query string list
     and return the first result.
@@ -820,12 +811,12 @@ def parse_json_value_from_request(
 @overload
 def parse_json_value_from_request(
     request: Request, allow_empty_body: bool = False
-) -> Optional[JsonDict]: ...
+) -> JsonDict | None: ...
 
 
 def parse_json_value_from_request(
     request: Request, allow_empty_body: bool = False
-) -> Optional[JsonDict]:
+) -> JsonDict | None:
     """Parse a JSON value from the body of a twisted HTTP request.
 
     Args:
@@ -892,7 +883,7 @@ def parse_json_object_from_request(
 Model = TypeVar("Model", bound=BaseModel)
 
 
-def validate_json_object(content: JsonDict, model_type: Type[Model]) -> Model:
+def validate_json_object(content: JsonDict, model_type: type[Model]) -> Model:
     """Validate a deserialized JSON object using the given pydantic model.
 
     Raises:
@@ -900,20 +891,20 @@ def validate_json_object(content: JsonDict, model_type: Type[Model]) -> Model:
             if it wasn't a JSON object.
     """
     try:
-        instance = model_type.parse_obj(content)
+        instance = model_type.model_validate(content)
     except ValidationError as e:
+        err_type = e.errors()[0]["type"]
+
         # Choose a matrix error code. The catch-all is BAD_JSON, but we try to find a
         # more specific error if possible (which occasionally helps us to be spec-
         # compliant) This is a bit awkward because the spec's error codes aren't very
         # clear-cut: BAD_JSON arguably overlaps with MISSING_PARAM and INVALID_PARAM.
         errcode = Codes.BAD_JSON
 
-        raw_errors = e.raw_errors
-        if len(raw_errors) == 1 and isinstance(raw_errors[0], ErrorWrapper):
-            raw_error = raw_errors[0].exc
-            if isinstance(raw_error, MissingError):
+        if e.error_count() == 1:
+            if err_type == "missing":
                 errcode = Codes.MISSING_PARAM
-            elif isinstance(raw_error, PydanticValueError):
+            elif err_type == "value_error":
                 errcode = Codes.INVALID_PARAM
 
         raise SynapseError(HTTPStatus.BAD_REQUEST, str(e), errcode=errcode)
@@ -922,7 +913,7 @@ def validate_json_object(content: JsonDict, model_type: Type[Model]) -> Model:
 
 
 def parse_and_validate_json_object_from_request(
-    request: Request, model_type: Type[Model]
+    request: Request, model_type: type[Model]
 ) -> Model:
     """Parse a JSON object from the body of a twisted HTTP request, then deserialise and
     validate using the given pydantic model.
@@ -988,8 +979,8 @@ class ResolveRoomIdMixin:
         self.room_member_handler = hs.get_room_member_handler()
 
     async def resolve_room_id(
-        self, room_identifier: str, remote_room_hosts: Optional[List[str]] = None
-    ) -> Tuple[str, Optional[List[str]]]:
+        self, room_identifier: str, remote_room_hosts: list[str] | None = None
+    ) -> tuple[str, list[str] | None]:
         """
         Resolve a room identifier to a room ID, if necessary.
 
diff --git a/synapse/http/site.py b/synapse/http/site.py
index 2c0c301c03..03d5d048b1 100644
--- a/synapse/http/site.py
+++ b/synapse/http/site.py
@@ -22,7 +22,7 @@ import contextlib
 import logging
 import time
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Any, Generator, Optional, Tuple, Union
+from typing import TYPE_CHECKING, Any, Generator
 
 import attr
 from zope.interface import implementer
@@ -30,6 +30,7 @@ from zope.interface import implementer
 from twisted.internet.address import UNIXAddress
 from twisted.internet.defer import Deferred
 from twisted.internet.interfaces import IAddress
+from twisted.internet.protocol import Protocol
 from twisted.python.failure import Failure
 from twisted.web.http import HTTPChannel
 from twisted.web.resource import IResource, Resource
@@ -87,7 +88,7 @@ class SynapseRequest(Request):
         our_server_name: str,
         *args: Any,
         max_request_body_size: int = 1024,
-        request_id_header: Optional[str] = None,
+        request_id_header: str | None = None,
         **kw: Any,
     ):
         super().__init__(channel, *args, **kw)
@@ -101,18 +102,18 @@ class SynapseRequest(Request):
 
         # The requester, if authenticated. For federation requests this is the
         # server name, for client requests this is the Requester object.
-        self._requester: Optional[Union[Requester, str]] = None
+        self._requester: Requester | str | None = None
 
         # An opentracing span for this request. Will be closed when the request is
         # completely processed.
-        self._opentracing_span: "Optional[opentracing.Span]" = None
+        self._opentracing_span: "opentracing.Span | None" = None
 
         # we can't yet create the logcontext, as we don't know the method.
-        self.logcontext: Optional[LoggingContext] = None
+        self.logcontext: LoggingContext | None = None
 
         # The `Deferred` to cancel if the client disconnects early and
         # `is_render_cancellable` is set. Expected to be set by `Resource.render`.
-        self.render_deferred: Optional["Deferred[None]"] = None
+        self.render_deferred: "Deferred[None]" | None = None
         # A boolean indicating whether `render_deferred` should be cancelled if the
         # client disconnects early. Expected to be set by the coroutine started by
         # `Resource.render`, if rendering is asynchronous.
@@ -126,11 +127,11 @@ class SynapseRequest(Request):
         self._is_processing = False
 
         # the time when the asynchronous request handler completed its processing
-        self._processing_finished_time: Optional[float] = None
+        self._processing_finished_time: float | None = None
 
         # what time we finished sending the response to the client (or the connection
         # dropped)
-        self.finish_time: Optional[float] = None
+        self.finish_time: float | None = None
 
     def __repr__(self) -> str:
         # We overwrite this so that we don't log ``access_token``
@@ -194,11 +195,11 @@ class SynapseRequest(Request):
         super().handleContentChunk(data)
 
     @property
-    def requester(self) -> Optional[Union[Requester, str]]:
+    def requester(self) -> Requester | str | None:
         return self._requester
 
     @requester.setter
-    def requester(self, value: Union[Requester, str]) -> None:
+    def requester(self, value: Requester | str) -> None:
         # Store the requester, and update some properties based on it.
 
         # This should only be called once.
@@ -245,7 +246,7 @@ class SynapseRequest(Request):
         Returns:
             The redacted URI as a string.
         """
-        uri: Union[bytes, str] = self.uri
+        uri: bytes | str = self.uri
         if isinstance(uri, bytes):
             uri = uri.decode("ascii", errors="replace")
         return redact_uri(uri)
@@ -260,12 +261,12 @@ class SynapseRequest(Request):
         Returns:
             The request method as a string.
         """
-        method: Union[bytes, str] = self.method
+        method: bytes | str = self.method
         if isinstance(method, bytes):
             return self.method.decode("ascii")
         return method
 
-    def get_authenticated_entity(self) -> Tuple[Optional[str], Optional[str]]:
+    def get_authenticated_entity(self) -> tuple[str | None, str | None]:
         """
         Get the "authenticated" entity of the request, which might be the user
         performing the action, or a user being puppeted by a server admin.
@@ -402,7 +403,7 @@ class SynapseRequest(Request):
             with PreserveLoggingContext(self.logcontext):
                 self._finished_processing()
 
-    def connectionLost(self, reason: Union[Failure, Exception]) -> None:
+    def connectionLost(self, reason: Failure | Exception) -> None:
         """Called when the client connection is closed before the response is written.
 
         Overrides twisted.web.server.Request.connectionLost to record the finish time and
@@ -594,7 +595,7 @@ class XForwardedForRequest(SynapseRequest):
     """
 
     # the client IP and ssl flag, as extracted from the headers.
-    _forwarded_for: "Optional[_XForwardedForAddress]" = None
+    _forwarded_for: "_XForwardedForAddress | None" = None
     _forwarded_https: bool = False
 
     def requestReceived(self, command: bytes, path: bytes, version: bytes) -> None:
@@ -660,6 +661,70 @@ class _XForwardedForAddress:
     host: str
 
 
+class SynapseProtocol(HTTPChannel):
+    """
+    Synapse-specific twisted http Protocol.
+
+    This is a small wrapper around the twisted HTTPChannel so we can track active
+    connections in order to close any outstanding connections on shutdown.
+    """
+
+    def __init__(
+        self,
+        site: "SynapseSite",
+        our_server_name: str,
+        max_request_body_size: int,
+        request_id_header: str | None,
+        request_class: type,
+    ):
+        super().__init__()
+        self.factory: SynapseSite = site
+        self.site = site
+        self.our_server_name = our_server_name
+        self.max_request_body_size = max_request_body_size
+        self.request_id_header = request_id_header
+        self.request_class = request_class
+
+    def connectionMade(self) -> None:
+        """
+        Called when a connection is made.
+
+        This may be considered the initializer of the protocol, because
+        it is called when the connection is completed.
+
+        Add the connection to the factory's connection list when it's established.
+        """
+        super().connectionMade()
+        self.factory.addConnection(self)
+
+    def connectionLost(self, reason: Failure) -> None:  # type: ignore[override]
+        """
+        Called when the connection is shut down.
+
+        Clear any circular references here, and any external references to this
+        Protocol. The connection has been closed. In our case, we need to remove the
+        connection from the factory's connection list, when it's lost.
+        """
+        super().connectionLost(reason)
+        self.factory.removeConnection(self)
+
+    def requestFactory(self, http_channel: HTTPChannel, queued: bool) -> SynapseRequest:  # type: ignore[override]
+        """
+        A callable used to build `twisted.web.iweb.IRequest` objects.
+
+        Use our own custom SynapseRequest type instead of the regular
+        twisted.web.server.Request.
+        """
+        return self.request_class(
+            self,
+            self.factory,
+            our_server_name=self.our_server_name,
+            max_request_body_size=self.max_request_body_size,
+            queued=queued,
+            request_id_header=self.request_id_header,
+        )
+
+
 class SynapseSite(ProxySite):
     """
     Synapse-specific twisted http Site
@@ -676,6 +741,7 @@ class SynapseSite(ProxySite):
 
     def __init__(
         self,
+        *,
         logger_name: str,
         site_tag: str,
         config: ListenerConfig,
@@ -710,23 +776,44 @@ class SynapseSite(ProxySite):
 
         assert config.http_options is not None
         proxied = config.http_options.x_forwarded
-        request_class = XForwardedForRequest if proxied else SynapseRequest
+        self.request_class = XForwardedForRequest if proxied else SynapseRequest
 
-        request_id_header = config.http_options.request_id_header
+        self.request_id_header = config.http_options.request_id_header
+        self.max_request_body_size = max_request_body_size
 
-        def request_factory(channel: HTTPChannel, queued: bool) -> Request:
-            return request_class(
-                channel,
-                self,
-                our_server_name=self.server_name,
-                max_request_body_size=max_request_body_size,
-                queued=queued,
-                request_id_header=request_id_header,
-            )
-
-        self.requestFactory = request_factory  # type: ignore
         self.access_logger = logging.getLogger(logger_name)
         self.server_version_string = server_version_string.encode("ascii")
+        self.connections: list[Protocol] = []
+
+    def buildProtocol(self, addr: IAddress) -> SynapseProtocol:
+        protocol = SynapseProtocol(
+            self,
+            self.server_name,
+            self.max_request_body_size,
+            self.request_id_header,
+            self.request_class,
+        )
+        return protocol
+
+    def addConnection(self, protocol: Protocol) -> None:
+        self.connections.append(protocol)
+
+    def removeConnection(self, protocol: Protocol) -> None:
+        if protocol in self.connections:
+            self.connections.remove(protocol)
+
+    def stopFactory(self) -> None:
+        super().stopFactory()
+
+        # Shutdown any connections which are still active.
+        # These can be long lived HTTP connections which wouldn't normally be closed
+        # when calling `shutdown` on the respective `Port`.
+        # Closing the connections here is required for us to fully shutdown the
+        # `SynapseHomeServer` in order for it to be garbage collected.
+        for protocol in self.connections[:]:
+            if protocol.transport is not None:
+                protocol.transport.loseConnection()
+        self.connections.clear()
 
     def log(self, request: SynapseRequest) -> None:  # type: ignore[override]
         pass
@@ -734,5 +821,5 @@ class SynapseSite(ProxySite):
 
 @attr.s(auto_attribs=True, frozen=True, slots=True)
 class RequestInfo:
-    user_agent: Optional[str]
+    user_agent: str | None
     ip: str
diff --git a/synapse/http/types.py b/synapse/http/types.py
index dd954b6c20..a04a285397 100644
--- a/synapse/http/types.py
+++ b/synapse/http/types.py
@@ -18,10 +18,10 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Iterable, Mapping, Union
+from typing import Iterable, Mapping
 
 # the type of the query params, to be passed into `urlencode` with `doseq=True`.
-QueryParamValue = Union[str, bytes, Iterable[Union[str, bytes]]]
-QueryParams = Union[Mapping[str, QueryParamValue], Mapping[bytes, QueryParamValue]]
+QueryParamValue = str | bytes | Iterable[str | bytes]
+QueryParams = Mapping[str, QueryParamValue] | Mapping[bytes, QueryParamValue]
 
 __all__ = ["QueryParams"]
diff --git a/synapse/logging/_remote.py b/synapse/logging/_remote.py
index ac34fa6525..e3e0ba4beb 100644
--- a/synapse/logging/_remote.py
+++ b/synapse/logging/_remote.py
@@ -25,7 +25,7 @@ import traceback
 from collections import deque
 from ipaddress import IPv4Address, IPv6Address, ip_address
 from math import floor
-from typing import Callable, Deque, Optional
+from typing import Callable
 
 import attr
 from zope.interface import implementer
@@ -66,7 +66,7 @@ class LogProducer:
     # (connected and registerProducer) which are part of the implementation.
     transport: Connection
     _format: Callable[[logging.LogRecord], str]
-    _buffer: Deque[logging.LogRecord]
+    _buffer: deque[logging.LogRecord]
     _paused: bool = attr.ib(default=False, init=False)
 
     def pauseProducing(self) -> None:
@@ -113,16 +113,16 @@ class RemoteHandler(logging.Handler):
         port: int,
         maximum_buffer: int = 1000,
         level: int = logging.NOTSET,
-        _reactor: Optional[IReactorTime] = None,
+        _reactor: IReactorTime | None = None,
     ):
         super().__init__(level=level)
         self.host = host
         self.port = port
         self.maximum_buffer = maximum_buffer
 
-        self._buffer: Deque[logging.LogRecord] = deque()
-        self._connection_waiter: Optional[Deferred] = None
-        self._producer: Optional[LogProducer] = None
+        self._buffer: deque[logging.LogRecord] = deque()
+        self._connection_waiter: Deferred | None = None
+        self._producer: LogProducer | None = None
 
         # Connect without DNS lookups if it's a direct IP.
         if _reactor is None:
diff --git a/synapse/logging/context.py b/synapse/logging/context.py
index 119d3be7bf..2410d95720 100644
--- a/synapse/logging/context.py
+++ b/synapse/logging/context.py
@@ -33,7 +33,6 @@ See doc/log_contexts.rst for details on how this works.
 import logging
 import threading
 import typing
-import warnings
 from types import TracebackType
 from typing import (
     TYPE_CHECKING,
@@ -41,9 +40,6 @@ from typing import (
     Awaitable,
     Callable,
     Literal,
-    Optional,
-    Tuple,
-    Type,
     TypeVar,
     Union,
     overload,
@@ -55,11 +51,29 @@ from typing_extensions import ParamSpec
 from twisted.internet import defer, threads
 from twisted.python.threadpool import ThreadPool
 
+from synapse.logging.loggers import ExplicitlyConfiguredLogger
+from synapse.util.stringutils import random_string_insecure_fast
+
 if TYPE_CHECKING:
+    from synapse.logging.scopecontextmanager import _LogContextScope
     from synapse.types import ISynapseReactor
 
 logger = logging.getLogger(__name__)
 
+original_logger_class = logging.getLoggerClass()
+logging.setLoggerClass(ExplicitlyConfiguredLogger)
+logcontext_debug_logger = logging.getLogger("synapse.logging.context.debug")
+"""
+A logger for debugging when the logcontext switches.
+
+Because this is very noisy and probably something only developers want to see when
+debugging logcontext problems, we want people to explictly opt-in before seeing anything
+in the logs. Requires explicitly setting `synapse.logging.context.debug` in the logging
+configuration and does not inherit the log level from the parent logger.
+"""
+# Restore the original logger class
+logging.setLoggerClass(original_logger_class)
+
 try:
     import resource
 
@@ -73,7 +87,7 @@ try:
 
     is_thread_resource_usage_supported = True
 
-    def get_thread_resource_usage() -> "Optional[resource.struct_rusage]":
+    def get_thread_resource_usage() -> "resource.struct_rusage | None":
         return resource.getrusage(RUSAGE_THREAD)
 
 except Exception:
@@ -81,7 +95,7 @@ except Exception:
     # won't track resource usage.
     is_thread_resource_usage_supported = False
 
-    def get_thread_resource_usage() -> "Optional[resource.struct_rusage]":
+    def get_thread_resource_usage() -> "resource.struct_rusage | None":
         return None
 
 
@@ -122,7 +136,7 @@ class ContextResourceUsage:
         "evt_db_fetch_count",
     ]
 
-    def __init__(self, copy_from: "Optional[ContextResourceUsage]" = None) -> None:
+    def __init__(self, copy_from: "ContextResourceUsage | None" = None) -> None:
         """Create a new ContextResourceUsage
 
         Args:
@@ -215,8 +229,8 @@ class ContextRequest:
     request_id: str
     ip_address: str
     site_tag: str
-    requester: Optional[str]
-    authenticated_entity: Optional[str]
+    requester: str | None
+    authenticated_entity: str | None
     method: str
     url: str
     protocol: str
@@ -238,7 +252,14 @@ class _Sentinel:
     we should always know which server the logs are coming from.
     """
 
-    __slots__ = ["previous_context", "finished", "server_name", "request", "tag"]
+    __slots__ = [
+        "previous_context",
+        "finished",
+        "scope",
+        "server_name",
+        "request",
+        "tag",
+    ]
 
     def __init__(self) -> None:
         # Minimal set for compatibility with LoggingContext
@@ -246,15 +267,16 @@ class _Sentinel:
         self.finished = False
         self.server_name = "unknown_server_from_sentinel_context"
         self.request = None
+        self.scope = None
         self.tag = None
 
     def __str__(self) -> str:
         return "sentinel"
 
-    def start(self, rusage: "Optional[resource.struct_rusage]") -> None:
+    def start(self, rusage: "resource.struct_rusage | None") -> None:
         pass
 
-    def stop(self, rusage: "Optional[resource.struct_rusage]") -> None:
+    def stop(self, rusage: "resource.struct_rusage | None") -> None:
         pass
 
     def add_database_transaction(self, duration_sec: float) -> None:
@@ -303,6 +325,7 @@ class LoggingContext:
         "finished",
         "request",
         "tag",
+        "scope",
     ]
 
     def __init__(
@@ -310,8 +333,8 @@ class LoggingContext:
         *,
         name: str,
         server_name: str,
-        parent_context: "Optional[LoggingContext]" = None,
-        request: Optional[ContextRequest] = None,
+        parent_context: "LoggingContext | None" = None,
+        request: ContextRequest | None = None,
     ) -> None:
         self.previous_context = current_context()
 
@@ -320,13 +343,14 @@ class LoggingContext:
 
         # The thread resource usage when the logcontext became active. None
         # if the context is not currently active.
-        self.usage_start: Optional[resource.struct_rusage] = None
+        self.usage_start: resource.struct_rusage | None = None
 
         self.name = name
         self.server_name = server_name
         self.main_thread = get_thread_id()
         self.request = None
         self.tag = ""
+        self.scope: "_LogContextScope" | None = None
 
         # keep track of whether we have hit the __exit__ block for this context
         # (suggesting that the the thing that created the context thinks it should
@@ -340,6 +364,9 @@ class LoggingContext:
             # which request this corresponds to
             self.request = self.parent_context.request
 
+            # we also track the current scope:
+            self.scope = self.parent_context.scope
+
         if request is not None:
             # the request param overrides the request from the parent context
             self.request = request
@@ -347,49 +374,9 @@ class LoggingContext:
     def __str__(self) -> str:
         return self.name
 
-    @classmethod
-    def current_context(cls) -> LoggingContextOrSentinel:
-        """Get the current logging context from thread local storage
-
-        This exists for backwards compatibility. ``current_context()`` should be
-        called directly.
-
-        Returns:
-            The current logging context
-        """
-        warnings.warn(
-            "synapse.logging.context.LoggingContext.current_context() is deprecated "
-            "in favor of synapse.logging.context.current_context().",
-            DeprecationWarning,
-            stacklevel=2,
-        )
-        return current_context()
-
-    @classmethod
-    def set_current_context(
-        cls, context: LoggingContextOrSentinel
-    ) -> LoggingContextOrSentinel:
-        """Set the current logging context in thread local storage
-
-        This exists for backwards compatibility. ``set_current_context()`` should be
-        called directly.
-
-        Args:
-            context: The context to activate.
-
-        Returns:
-            The context that was previously active
-        """
-        warnings.warn(
-            "synapse.logging.context.LoggingContext.set_current_context() is deprecated "
-            "in favor of synapse.logging.context.set_current_context().",
-            DeprecationWarning,
-            stacklevel=2,
-        )
-        return set_current_context(context)
-
     def __enter__(self) -> "LoggingContext":
         """Enters this logging context into thread local storage"""
+        logcontext_debug_logger.debug("LoggingContext(%s).__enter__", self.name)
         old_context = set_current_context(self)
         if self.previous_context != old_context:
             logcontext_error(
@@ -403,15 +390,18 @@ class LoggingContext:
 
     def __exit__(
         self,
-        type: Optional[Type[BaseException]],
-        value: Optional[BaseException],
-        traceback: Optional[TracebackType],
+        type: type[BaseException] | None,
+        value: BaseException | None,
+        traceback: TracebackType | None,
     ) -> None:
         """Restore the logging context in thread local storage to the state it
         was before this context was entered.
         Returns:
             None to avoid suppressing any exceptions that were thrown.
         """
+        logcontext_debug_logger.debug(
+            "LoggingContext(%s).__exit__ --> %s", self.name, self.previous_context
+        )
         current = set_current_context(self.previous_context)
         if current is not self:
             if current is SENTINEL_CONTEXT:
@@ -426,7 +416,7 @@ class LoggingContext:
         # recorded against the correct metrics.
         self.finished = True
 
-    def start(self, rusage: "Optional[resource.struct_rusage]") -> None:
+    def start(self, rusage: "resource.struct_rusage | None") -> None:
         """
         Record that this logcontext is currently running.
 
@@ -451,7 +441,7 @@ class LoggingContext:
         else:
             self.usage_start = rusage
 
-    def stop(self, rusage: "Optional[resource.struct_rusage]") -> None:
+    def stop(self, rusage: "resource.struct_rusage | None") -> None:
         """
         Record that this logcontext is no longer running.
 
@@ -505,13 +495,13 @@ class LoggingContext:
 
         return res
 
-    def _get_cputime(self, current: "resource.struct_rusage") -> Tuple[float, float]:
+    def _get_cputime(self, current: "resource.struct_rusage") -> tuple[float, float]:
         """Get the cpu usage time between start() and the given rusage
 
         Args:
             rusage: the current resource usage
 
-        Returns: Tuple[float, float]: seconds in user mode, seconds in system mode
+        Returns: tuple[float, float]: seconds in user mode, seconds in system mode
         """
         assert self.usage_start is not None
 
@@ -613,25 +603,57 @@ class LoggingContextFilter(logging.Filter):
         self._default_request = request
 
     def filter(self, record: logging.LogRecord) -> Literal[True]:
-        """Add each fields from the logging contexts to the record.
+        """
+        Add each field from the logging context to the record.
+
+        Please be mindful of 3rd-party code outside of Synapse (like in the case of
+        Synapse Pro for small hosts) as this is running as a global log record filter.
+        Other code may have set their own attributes on the record and the log record
+        may not be relevant to Synapse at all so we should not mangle it.
+
+        We can have some defaults but we should avoid overwriting existing attributes on
+        any log record unless we actually have a Synapse logcontext (not just the
+        default sentinel logcontext).
+
         Returns:
             True to include the record in the log output.
         """
         context = current_context()
         record.request = self._default_request
-        record.server_name = "unknown_server_from_no_context"
+
+        # Avoid overwriting an existing `server_name` on the record. This is running in
+        # the context of a global log record filter so there may be 3rd-party code that
+        # adds their own `server_name` and we don't want to interfere with that
+        # (clobber).
+        if not hasattr(record, "server_name"):
+            record.server_name = "unknown_server_from_no_logcontext"
 
         # context should never be None, but if it somehow ends up being, then
         # we end up in a death spiral of infinite loops, so let's check, for
         # robustness' sake.
         if context is not None:
-            record.server_name = context.server_name
+
+            def safe_set(attr: str, value: Any) -> None:
+                """
+                Only write the attribute if it hasn't already been set or we actually have
+                a Synapse logcontext (indicating that this log record is relevant to
+                Synapse).
+                """
+                if context is not SENTINEL_CONTEXT or not hasattr(record, attr):
+                    setattr(record, attr, value)
+
+            safe_set("server_name", context.server_name)
+
             # Logging is interested in the request ID. Note that for backwards
             # compatibility this is stored as the "request" on the record.
-            record.request = str(context)
+            safe_set("request", str(context))
 
             # Add some data from the HTTP request.
             request = context.request
+            # The sentinel logcontext has no request so if we get past this point, we
+            # know we have some actual Synapse logcontext and don't need to worry about
+            # using `safe_set`. We'll consider this an optimization since this is a
+            # pretty hot-path.
             if request is None:
                 return True
 
@@ -660,22 +682,35 @@ class PreserveLoggingContext:
     reactor back to the code).
     """
 
-    __slots__ = ["_old_context", "_new_context"]
+    __slots__ = ["_old_context", "_new_context", "_instance_id"]
 
     def __init__(
         self, new_context: LoggingContextOrSentinel = SENTINEL_CONTEXT
     ) -> None:
         self._new_context = new_context
+        self._instance_id = random_string_insecure_fast(5)
 
     def __enter__(self) -> None:
+        logcontext_debug_logger.debug(
+            "PreserveLoggingContext(%s).__enter__ %s --> %s",
+            self._instance_id,
+            current_context(),
+            self._new_context,
+        )
         self._old_context = set_current_context(self._new_context)
 
     def __exit__(
         self,
-        type: Optional[Type[BaseException]],
-        value: Optional[BaseException],
-        traceback: Optional[TracebackType],
+        type: type[BaseException] | None,
+        value: BaseException | None,
+        traceback: TracebackType | None,
     ) -> None:
+        logcontext_debug_logger.debug(
+            "PreserveLoggingContext(%s).__exit %s --> %s",
+            self._instance_id,
+            current_context(),
+            self._old_context,
+        )
         context = set_current_context(self._old_context)
 
         if context != self._new_context:
@@ -787,10 +822,7 @@ def preserve_fn(f: Callable[P, R]) -> Callable[P, "defer.Deferred[R]"]: ...
 
 
 def preserve_fn(
-    f: Union[
-        Callable[P, R],
-        Callable[P, Awaitable[R]],
-    ],
+    f: Callable[P, R] | Callable[P, Awaitable[R]],
 ) -> Callable[P, "defer.Deferred[R]"]:
     """Function decorator which wraps the function with run_in_background"""
 
@@ -816,10 +848,7 @@ def run_in_background(
 
 
 def run_in_background(
-    f: Union[
-        Callable[P, R],
-        Callable[P, Awaitable[R]],
-    ],
+    f: Callable[P, R] | Callable[P, Awaitable[R]],
     *args: P.args,
     **kwargs: P.kwargs,
 ) -> "defer.Deferred[R]":
@@ -855,7 +884,11 @@ def run_in_background(
         Note that the returned Deferred does not follow the synapse logcontext
         rules.
     """
+    instance_id = random_string_insecure_fast(5)
     calling_context = current_context()
+    logcontext_debug_logger.debug(
+        "run_in_background(%s): called with logcontext=%s", instance_id, calling_context
+    )
     try:
         # (kick off the task in the current context)
         res = f(*args, **kwargs)
@@ -888,7 +921,7 @@ def run_in_background(
         # If the function messes with logcontexts, we can assume it follows the Synapse
         # logcontext rules (Rules for functions returning awaitables: "If the awaitable
         # is already complete, the function returns with the same logcontext it started
-        # with."). If it function doesn't touch logcontexts at all, we can also assume
+        # with."). If the function doesn't touch logcontexts at all, we can also assume
         # the logcontext is unchanged.
         #
         # Either way, the function should have maintained the calling logcontext, so we
@@ -897,6 +930,21 @@ def run_in_background(
         # to reset the logcontext to the sentinel logcontext as that would run
         # immediately (remember our goal is to maintain the calling logcontext when we
         # return).
+        if current_context() != calling_context:
+            logcontext_error(
+                "run_in_background(%s): deferred already completed but the function did not maintain the calling logcontext %s (found %s)"
+                % (
+                    instance_id,
+                    calling_context,
+                    current_context(),
+                )
+            )
+        else:
+            logcontext_debug_logger.debug(
+                "run_in_background(%s): deferred already completed (maintained the calling logcontext %s)",
+                instance_id,
+                calling_context,
+            )
         return d
 
     # Since the function we called may follow the Synapse logcontext rules (Rules for
@@ -907,6 +955,11 @@ def run_in_background(
     #
     # Our goal is to have the caller logcontext unchanged after firing off the
     # background task and returning.
+    logcontext_debug_logger.debug(
+        "run_in_background(%s): restoring calling logcontext %s",
+        instance_id,
+        calling_context,
+    )
     set_current_context(calling_context)
 
     # If the function we called is playing nice and following the Synapse logcontext
@@ -922,7 +975,23 @@ def run_in_background(
     # which is supposed to have a single entry and exit point. But
     # by spawning off another deferred, we are effectively
     # adding a new exit point.)
-    d.addBoth(_set_context_cb, SENTINEL_CONTEXT)
+    if logcontext_debug_logger.isEnabledFor(logging.DEBUG):
+
+        def _log_set_context_cb(
+            result: ResultT, context: LoggingContextOrSentinel
+        ) -> ResultT:
+            logcontext_debug_logger.debug(
+                "run_in_background(%s): resetting logcontext to %s",
+                instance_id,
+                context,
+            )
+            set_current_context(context)
+            return result
+
+        d.addBoth(_log_set_context_cb, SENTINEL_CONTEXT)
+    else:
+        d.addBoth(_set_context_cb, SENTINEL_CONTEXT)
+
     return d
 
 
@@ -978,10 +1047,21 @@ def make_deferred_yieldable(deferred: "defer.Deferred[T]") -> "defer.Deferred[T]
     restores the old context once the awaitable completes (execution passes from the
     reactor back to the code).
     """
+    instance_id = random_string_insecure_fast(5)
+    logcontext_debug_logger.debug(
+        "make_deferred_yieldable(%s): called with logcontext=%s",
+        instance_id,
+        current_context(),
+    )
+
     # The deferred has already completed
     if deferred.called and not deferred.paused:
         # it looks like this deferred is ready to run any callbacks we give it
         # immediately. We may as well optimise out the logcontext faffery.
+        logcontext_debug_logger.debug(
+            "make_deferred_yieldable(%s): deferred already completed and the function should have maintained the logcontext",
+            instance_id,
+        )
         return deferred
 
     # Our goal is to have the caller logcontext unchanged after they yield/await the
@@ -993,8 +1073,31 @@ def make_deferred_yieldable(deferred: "defer.Deferred[T]") -> "defer.Deferred[T]
     # does) while the deferred runs in the reactor event loop, we reset the logcontext
     # and add a callback to the deferred to restore it so the caller's logcontext is
     # active when the deferred completes.
-    prev_context = set_current_context(SENTINEL_CONTEXT)
-    deferred.addBoth(_set_context_cb, prev_context)
+
+    logcontext_debug_logger.debug(
+        "make_deferred_yieldable(%s): resetting logcontext to %s",
+        instance_id,
+        SENTINEL_CONTEXT,
+    )
+    calling_context = set_current_context(SENTINEL_CONTEXT)
+
+    if logcontext_debug_logger.isEnabledFor(logging.DEBUG):
+
+        def _log_set_context_cb(
+            result: ResultT, context: LoggingContextOrSentinel
+        ) -> ResultT:
+            logcontext_debug_logger.debug(
+                "make_deferred_yieldable(%s): restoring calling logcontext to %s",
+                instance_id,
+                context,
+            )
+            set_current_context(context)
+            return result
+
+        deferred.addBoth(_log_set_context_cb, calling_context)
+    else:
+        deferred.addBoth(_set_context_cb, calling_context)
+
     return deferred
 
 
diff --git a/synapse/logging/formatter.py b/synapse/logging/formatter.py
index 228e5ed278..70b6d7f6a1 100644
--- a/synapse/logging/formatter.py
+++ b/synapse/logging/formatter.py
@@ -23,7 +23,6 @@ import logging
 import traceback
 from io import StringIO
 from types import TracebackType
-from typing import Optional, Tuple, Type
 
 
 class LogFormatter(logging.Formatter):
@@ -38,10 +37,10 @@ class LogFormatter(logging.Formatter):
 
     def formatException(
         self,
-        ei: Tuple[
-            Optional[Type[BaseException]],
-            Optional[BaseException],
-            Optional[TracebackType],
+        ei: tuple[
+            type[BaseException] | None,
+            BaseException | None,
+            TracebackType | None,
         ],
     ) -> str:
         sio = StringIO()
diff --git a/synapse/logging/handlers.py b/synapse/logging/handlers.py
index b7945aac72..976c7075d4 100644
--- a/synapse/logging/handlers.py
+++ b/synapse/logging/handlers.py
@@ -3,7 +3,7 @@ import time
 from logging import Handler, LogRecord
 from logging.handlers import MemoryHandler
 from threading import Thread
-from typing import Optional, cast
+from typing import cast
 
 from twisted.internet.interfaces import IReactorCore
 
@@ -23,10 +23,10 @@ class PeriodicallyFlushingMemoryHandler(MemoryHandler):
         self,
         capacity: int,
         flushLevel: int = logging.ERROR,
-        target: Optional[Handler] = None,
+        target: Handler | None = None,
         flushOnClose: bool = True,
         period: float = 5.0,
-        reactor: Optional[IReactorCore] = None,
+        reactor: IReactorCore | None = None,
     ) -> None:
         """
         period: the period between automatic flushes
diff --git a/synapse/logging/opentracing.py b/synapse/logging/opentracing.py
index 8d350016ce..6e4e029163 100644
--- a/synapse/logging/opentracing.py
+++ b/synapse/logging/opentracing.py
@@ -183,13 +183,10 @@ from typing import (
     Callable,
     Collection,
     ContextManager,
-    Dict,
     Generator,
     Iterable,
-    List,
     Optional,
     Pattern,
-    Type,
     TypeVar,
     Union,
     cast,
@@ -251,17 +248,18 @@ class _DummyTagNames:
 try:
     import opentracing
     import opentracing.tags
-    from opentracing.scope_managers.contextvars import ContextVarsScopeManager
 
     tags = opentracing.tags
 except ImportError:
     opentracing = None  # type: ignore[assignment]
     tags = _DummyTagNames  # type: ignore[assignment]
-    ContextVarsScopeManager = None  # type: ignore
 try:
     from jaeger_client import Config as JaegerConfig
+
+    from synapse.logging.scopecontextmanager import LogContextScopeManager
 except ImportError:
     JaegerConfig = None  # type: ignore
+    LogContextScopeManager = None  # type: ignore
 
 
 try:
@@ -291,7 +289,7 @@ try:
             except Exception:
                 logger.exception("Failed to report span")
 
-    RustReporter: Optional[Type[_WrappedRustReporter]] = _WrappedRustReporter
+    RustReporter: type[_WrappedRustReporter] | None = _WrappedRustReporter
 except ImportError:
     RustReporter = None
 
@@ -356,7 +354,7 @@ class SynapseBaggage:
 # Block everything by default
 # A regex which matches the server_names to expose traces for.
 # None means 'block everything'.
-_homeserver_whitelist: Optional[Pattern[str]] = None
+_homeserver_whitelist: Pattern[str] | None = None
 
 # Util methods
 
@@ -372,11 +370,11 @@ R = TypeVar("R")
 T = TypeVar("T")
 
 
-def only_if_tracing(func: Callable[P, R]) -> Callable[P, Optional[R]]:
+def only_if_tracing(func: Callable[P, R]) -> Callable[P, R | None]:
     """Executes the function only if we're tracing. Otherwise returns None."""
 
     @wraps(func)
-    def _only_if_tracing_inner(*args: P.args, **kwargs: P.kwargs) -> Optional[R]:
+    def _only_if_tracing_inner(*args: P.args, **kwargs: P.kwargs) -> R | None:
         if opentracing:
             return func(*args, **kwargs)
         else:
@@ -388,18 +386,18 @@ def only_if_tracing(func: Callable[P, R]) -> Callable[P, Optional[R]]:
 @overload
 def ensure_active_span(
     message: str,
-) -> Callable[[Callable[P, R]], Callable[P, Optional[R]]]: ...
+) -> Callable[[Callable[P, R]], Callable[P, R | None]]: ...
 
 
 @overload
 def ensure_active_span(
     message: str, ret: T
-) -> Callable[[Callable[P, R]], Callable[P, Union[T, R]]]: ...
+) -> Callable[[Callable[P, R]], Callable[P, T | R]]: ...
 
 
 def ensure_active_span(
-    message: str, ret: Optional[T] = None
-) -> Callable[[Callable[P, R]], Callable[P, Union[Optional[T], R]]]:
+    message: str, ret: T | None = None
+) -> Callable[[Callable[P, R]], Callable[P, T | None | R]]:
     """Executes the operation only if opentracing is enabled and there is an active span.
     If there is no active span it logs message at the error level.
 
@@ -415,11 +413,11 @@ def ensure_active_span(
 
     def ensure_active_span_inner_1(
         func: Callable[P, R],
-    ) -> Callable[P, Union[Optional[T], R]]:
+    ) -> Callable[P, T | None | R]:
         @wraps(func)
         def ensure_active_span_inner_2(
             *args: P.args, **kwargs: P.kwargs
-        ) -> Union[Optional[T], R]:
+        ) -> T | None | R:
             if not opentracing:
                 return ret
 
@@ -483,7 +481,7 @@ def init_tracer(hs: "HomeServer") -> None:
     config = JaegerConfig(
         config=jaeger_config,
         service_name=f"{hs.config.server.server_name} {instance_name_by_type}",
-        scope_manager=ContextVarsScopeManager(),
+        scope_manager=LogContextScopeManager(),
         metrics_factory=PrometheusMetricsFactory(),
     )
 
@@ -534,10 +532,10 @@ def whitelisted_homeserver(destination: str) -> bool:
 # Could use kwargs but I want these to be explicit
 def start_active_span(
     operation_name: str,
-    child_of: Optional[Union["opentracing.Span", "opentracing.SpanContext"]] = None,
-    references: Optional[List["opentracing.Reference"]] = None,
-    tags: Optional[Dict[str, str]] = None,
-    start_time: Optional[float] = None,
+    child_of: Union["opentracing.Span", "opentracing.SpanContext"] | None = None,
+    references: list["opentracing.Reference"] | None = None,
+    tags: dict[str, str] | None = None,
+    start_time: float | None = None,
     ignore_active_span: bool = False,
     finish_on_close: bool = True,
     *,
@@ -575,9 +573,9 @@ def start_active_span(
 def start_active_span_follows_from(
     operation_name: str,
     contexts: Collection,
-    child_of: Optional[Union["opentracing.Span", "opentracing.SpanContext"]] = None,
-    tags: Optional[Dict[str, str]] = None,
-    start_time: Optional[float] = None,
+    child_of: Union["opentracing.Span", "opentracing.SpanContext"] | None = None,
+    tags: dict[str, str] | None = None,
+    start_time: float | None = None,
     ignore_active_span: bool = False,
     *,
     inherit_force_tracing: bool = False,
@@ -630,11 +628,11 @@ def start_active_span_follows_from(
 
 
 def start_active_span_from_edu(
-    edu_content: Dict[str, Any],
+    edu_content: dict[str, Any],
     operation_name: str,
-    references: Optional[List["opentracing.Reference"]] = None,
-    tags: Optional[Dict[str, str]] = None,
-    start_time: Optional[float] = None,
+    references: list["opentracing.Reference"] | None = None,
+    tags: dict[str, str] | None = None,
+    start_time: float | None = None,
     ignore_active_span: bool = False,
     finish_on_close: bool = True,
 ) -> "opentracing.Scope":
@@ -683,20 +681,32 @@ def start_active_span_from_edu(
 
 # Opentracing setters for tags, logs, etc
 @only_if_tracing
-def active_span() -> Optional["opentracing.Span"]:
-    """Get the currently active span, if any"""
-    return opentracing.tracer.active_span
+def active_span(
+    *,
+    tracer: Optional["opentracing.Tracer"] = None,
+) -> Optional["opentracing.Span"]:
+    """
+    Get the currently active span, if any
+
+    Args:
+        tracer: override the opentracing tracer. By default the global tracer is used.
+    """
+    if tracer is None:
+        # use the global tracer by default
+        tracer = opentracing.tracer
+
+    return tracer.active_span
 
 
 @ensure_active_span("set a tag")
-def set_tag(key: str, value: Union[str, bool, int, float]) -> None:
+def set_tag(key: str, value: str | bool | int | float) -> None:
     """Sets a tag on the active span"""
     assert opentracing.tracer.active_span is not None
     opentracing.tracer.active_span.set_tag(key, value)
 
 
 @ensure_active_span("log")
-def log_kv(key_values: Dict[str, Any], timestamp: Optional[float] = None) -> None:
+def log_kv(key_values: dict[str, Any], timestamp: float | None = None) -> None:
     """Log to the active span"""
     assert opentracing.tracer.active_span is not None
     opentracing.tracer.active_span.log_kv(key_values, timestamp)
@@ -747,8 +757,8 @@ def is_context_forced_tracing(
 
 @ensure_active_span("inject the span into a header dict")
 def inject_header_dict(
-    headers: Dict[bytes, List[bytes]],
-    destination: Optional[str] = None,
+    headers: dict[bytes, list[bytes]],
+    destination: str | None = None,
     check_destination: bool = True,
 ) -> None:
     """
@@ -779,7 +789,7 @@ def inject_header_dict(
 
     span = opentracing.tracer.active_span
 
-    carrier: Dict[str, str] = {}
+    carrier: dict[str, str] = {}
     assert span is not None
     opentracing.tracer.inject(span.context, opentracing.Format.HTTP_HEADERS, carrier)
 
@@ -807,16 +817,16 @@ def inject_response_headers(response_headers: Headers) -> None:
 
 
 @ensure_active_span("inject the span into a header dict")
-def inject_request_headers(headers: Dict[str, str]) -> None:
+def inject_request_headers(headers: dict[str, str]) -> None:
     span = opentracing.tracer.active_span
     assert span is not None
     opentracing.tracer.inject(span.context, opentracing.Format.HTTP_HEADERS, headers)
 
 
 @ensure_active_span(
-    "get the active span context as a dict", ret=cast(Dict[str, str], {})
+    "get the active span context as a dict", ret=cast(dict[str, str], {})
 )
-def get_active_span_text_map(destination: Optional[str] = None) -> Dict[str, str]:
+def get_active_span_text_map(destination: str | None = None) -> dict[str, str]:
     """
     Gets a span context as a dict. This can be used instead of manually
     injecting a span into an empty carrier.
@@ -831,7 +841,7 @@ def get_active_span_text_map(destination: Optional[str] = None) -> Dict[str, str
     if destination and not whitelisted_homeserver(destination):
         return {}
 
-    carrier: Dict[str, str] = {}
+    carrier: dict[str, str] = {}
     assert opentracing.tracer.active_span is not None
     opentracing.tracer.inject(
         opentracing.tracer.active_span.context, opentracing.Format.TEXT_MAP, carrier
@@ -846,7 +856,7 @@ def active_span_context_as_string() -> str:
     Returns:
         The active span context encoded as a string.
     """
-    carrier: Dict[str, str] = {}
+    carrier: dict[str, str] = {}
     if opentracing:
         assert opentracing.tracer.active_span is not None
         opentracing.tracer.inject(
@@ -855,7 +865,7 @@ def active_span_context_as_string() -> str:
     return json_encoder.encode(carrier)
 
 
-def span_context_from_request(request: Request) -> "Optional[opentracing.SpanContext]":
+def span_context_from_request(request: Request) -> "opentracing.SpanContext | None":
     """Extract an opentracing context from the headers on an HTTP request
 
     This is useful when we have received an HTTP request from another part of our
@@ -875,12 +885,12 @@ def span_context_from_string(carrier: str) -> Optional["opentracing.SpanContext"
     Returns:
         The active span context decoded from a string.
     """
-    payload: Dict[str, str] = json_decoder.decode(carrier)
+    payload: dict[str, str] = json_decoder.decode(carrier)
     return opentracing.tracer.extract(opentracing.Format.TEXT_MAP, payload)
 
 
 @only_if_tracing
-def extract_text_map(carrier: Dict[str, str]) -> Optional["opentracing.SpanContext"]:
+def extract_text_map(carrier: dict[str, str]) -> Optional["opentracing.SpanContext"]:
     """
     Wrapper method for opentracing's tracer.extract for TEXT_MAP.
     Args:
@@ -1109,7 +1119,7 @@ def trace_servlet(
             # with JsonResource).
             scope.span.set_operation_name(request.request_metrics.name)
 
-            # Mypy seems to think that start_context.tag below can be Optional[str], but
+            # Mypy seems to think that start_context.tag below can be str | None, but
             # that doesn't appear to be correct and works in practice.
 
             request_tags[SynapseTags.REQUEST_TAG] = (
diff --git a/synapse/logging/scopecontextmanager.py b/synapse/logging/scopecontextmanager.py
new file mode 100644
index 0000000000..f3ec07eecf
--- /dev/null
+++ b/synapse/logging/scopecontextmanager.py
@@ -0,0 +1,160 @@
+#
+# This file is licensed under the Affero General Public License (AGPL) version 3.
+#
+# Copyright 2019 The Matrix.org Foundation C.I.C.
+# Copyright (C) 2023 New Vector, Ltd
+#
+# This program is free software: you can redistribute it and/or modify
+# it under the terms of the GNU Affero General Public License as
+# published by the Free Software Foundation, either version 3 of the
+# License, or (at your option) any later version.
+#
+# See the GNU Affero General Public License for more details:
+# <https://www.gnu.org/licenses/agpl-3.0.html>.
+#
+# Originally licensed under the Apache License, Version 2.0:
+# <http://www.apache.org/licenses/LICENSE-2.0>.
+#
+# [This file includes modifications made by New Vector Limited]
+#
+#
+
+import logging
+
+from opentracing import Scope, ScopeManager, Span
+
+from synapse.logging.context import (
+    LoggingContext,
+    current_context,
+    nested_logging_context,
+)
+
+logger = logging.getLogger(__name__)
+
+
+class LogContextScopeManager(ScopeManager):
+    """
+    The LogContextScopeManager tracks the active scope in opentracing
+    by using the log contexts which are native to synapse. This is so
+    that the basic opentracing api can be used across twisted defereds.
+
+    It would be nice just to use opentracing's ContextVarsScopeManager,
+    but currently that doesn't work due to https://twistedmatrix.com/trac/ticket/10301.
+    """
+
+    def __init__(self) -> None:
+        pass
+
+    @property
+    def active(self) -> Scope | None:
+        """
+        Returns the currently active Scope which can be used to access the
+        currently active Scope.span.
+        If there is a non-null Scope, its wrapped Span
+        becomes an implicit parent of any newly-created Span at
+        Tracer.start_active_span() time.
+
+        Return:
+            The Scope that is active, or None if not available.
+        """
+        ctx = current_context()
+        return ctx.scope
+
+    def activate(self, span: Span, finish_on_close: bool) -> Scope:
+        """
+        Makes a Span active.
+        Args
+            span: the span that should become active.
+            finish_on_close: whether Span should be automatically finished when
+                Scope.close() is called.
+
+        Returns:
+            Scope to control the end of the active period for
+            *span*. It is a programming error to neglect to call
+            Scope.close() on the returned instance.
+        """
+
+        ctx = current_context()
+
+        if not ctx:
+            logger.error("Tried to activate scope outside of loggingcontext")
+            return Scope(None, span)  # type: ignore[arg-type]
+
+        if ctx.scope is not None:
+            # start a new logging context as a child of the existing one.
+            # Doing so -- rather than updating the existing logcontext -- means that
+            # creating several concurrent spans under the same logcontext works
+            # correctly.
+            ctx = nested_logging_context("")
+            enter_logcontext = True
+        else:
+            # if there is no span currently associated with the current logcontext, we
+            # just store the scope in it.
+            #
+            # This feels a bit dubious, but it does hack around a problem where a
+            # span outlasts its parent logcontext (which would otherwise lead to
+            # "Re-starting finished log context" errors).
+            enter_logcontext = False
+
+        scope = _LogContextScope(self, span, ctx, enter_logcontext, finish_on_close)
+        ctx.scope = scope
+        if enter_logcontext:
+            ctx.__enter__()
+
+        return scope
+
+
+class _LogContextScope(Scope):
+    """
+    A custom opentracing scope, associated with a LogContext
+
+      * When the scope is closed, the logcontext's active scope is reset to None.
+        and - if enter_logcontext was set - the logcontext is finished too.
+    """
+
+    def __init__(
+        self,
+        manager: LogContextScopeManager,
+        span: Span,
+        logcontext: LoggingContext,
+        enter_logcontext: bool,
+        finish_on_close: bool,
+    ):
+        """
+        Args:
+            manager:
+                the manager that is responsible for this scope.
+            span:
+                the opentracing span which this scope represents the local
+                lifetime for.
+            logcontext:
+                the log context to which this scope is attached.
+            enter_logcontext:
+                if True the log context will be exited when the scope is finished
+            finish_on_close:
+                if True finish the span when the scope is closed
+        """
+        super().__init__(manager, span)
+        self.logcontext = logcontext
+        self._finish_on_close = finish_on_close
+        self._enter_logcontext = enter_logcontext
+
+    def __str__(self) -> str:
+        return f"Scope<{self.span}>"
+
+    def close(self) -> None:
+        active_scope = self.manager.active
+        if active_scope is not self:
+            logger.error(
+                "Closing scope %s which is not the currently-active one %s",
+                self,
+                active_scope,
+            )
+
+        if self._finish_on_close:
+            self.span.finish()
+
+        self.logcontext.scope = None
+
+        if self._enter_logcontext:
+            self.logcontext.__exit__(None, None, None)
diff --git a/synapse/media/_base.py b/synapse/media/_base.py
index 15b28074fd..e0313d2893 100644
--- a/synapse/media/_base.py
+++ b/synapse/media/_base.py
@@ -29,12 +29,7 @@ from typing import (
     TYPE_CHECKING,
     Awaitable,
     BinaryIO,
-    Dict,
     Generator,
-    List,
-    Optional,
-    Tuple,
-    Type,
 )
 
 import attr
@@ -137,8 +132,8 @@ async def respond_with_file(
     request: SynapseRequest,
     media_type: str,
     file_path: str,
-    file_size: Optional[int] = None,
-    upload_name: Optional[str] = None,
+    file_size: int | None = None,
+    upload_name: str | None = None,
 ) -> None:
     logger.debug("Responding with %r", file_path)
 
@@ -160,8 +155,8 @@ async def respond_with_file(
 def add_file_headers(
     request: Request,
     media_type: str,
-    file_size: Optional[int],
-    upload_name: Optional[str],
+    file_size: int | None,
+    upload_name: str | None,
 ) -> None:
     """Adds the correct response headers in preparation for responding with the
     media.
@@ -305,10 +300,10 @@ def _can_encode_filename_as_token(x: str) -> bool:
 async def respond_with_multipart_responder(
     clock: Clock,
     request: SynapseRequest,
-    responder: "Optional[Responder]",
+    responder: "Responder | None",
     media_type: str,
-    media_length: Optional[int],
-    upload_name: Optional[str],
+    media_length: int | None,
+    upload_name: str | None,
 ) -> None:
     """
     Responds to requests originating from the federation media `/download` endpoint by
@@ -396,10 +391,10 @@ async def respond_with_multipart_responder(
 
 async def respond_with_responder(
     request: SynapseRequest,
-    responder: "Optional[Responder]",
+    responder: "Responder | None",
     media_type: str,
-    file_size: Optional[int],
-    upload_name: Optional[str] = None,
+    file_size: int | None,
+    upload_name: str | None = None,
 ) -> None:
     """Responds to the request with given responder. If responder is None then
     returns 404.
@@ -505,9 +500,9 @@ class Responder(ABC):
 
     def __exit__(  # noqa: B027
         self,
-        exc_type: Optional[Type[BaseException]],
-        exc_val: Optional[BaseException],
-        exc_tb: Optional[TracebackType],
+        exc_type: type[BaseException] | None,
+        exc_val: BaseException | None,
+        exc_tb: TracebackType | None,
     ) -> None:
         pass
 
@@ -530,47 +525,47 @@ class FileInfo:
     """Details about a requested/uploaded file."""
 
     # The server name where the media originated from, or None if local.
-    server_name: Optional[str]
+    server_name: str | None
     # The local ID of the file. For local files this is the same as the media_id
     file_id: str
     # If the file is for the url preview cache
     url_cache: bool = False
     # Whether the file is a thumbnail or not.
-    thumbnail: Optional[ThumbnailInfo] = None
+    thumbnail: ThumbnailInfo | None = None
 
     # The below properties exist to maintain compatibility with third-party modules.
     @property
-    def thumbnail_width(self) -> Optional[int]:
+    def thumbnail_width(self) -> int | None:
         if not self.thumbnail:
             return None
         return self.thumbnail.width
 
     @property
-    def thumbnail_height(self) -> Optional[int]:
+    def thumbnail_height(self) -> int | None:
         if not self.thumbnail:
             return None
         return self.thumbnail.height
 
     @property
-    def thumbnail_method(self) -> Optional[str]:
+    def thumbnail_method(self) -> str | None:
         if not self.thumbnail:
             return None
         return self.thumbnail.method
 
     @property
-    def thumbnail_type(self) -> Optional[str]:
+    def thumbnail_type(self) -> str | None:
         if not self.thumbnail:
             return None
         return self.thumbnail.type
 
     @property
-    def thumbnail_length(self) -> Optional[int]:
+    def thumbnail_length(self) -> int | None:
         if not self.thumbnail:
             return None
         return self.thumbnail.length
 
 
-def get_filename_from_headers(headers: Dict[bytes, List[bytes]]) -> Optional[str]:
+def get_filename_from_headers(headers: dict[bytes, list[bytes]]) -> str | None:
     """
     Get the filename of the downloaded file by inspecting the
     Content-Disposition HTTP header.
@@ -618,7 +613,7 @@ def get_filename_from_headers(headers: Dict[bytes, List[bytes]]) -> Optional[str
     return upload_name
 
 
-def _parse_header(line: bytes) -> Tuple[bytes, Dict[bytes, bytes]]:
+def _parse_header(line: bytes) -> tuple[bytes, dict[bytes, bytes]]:
     """Parse a Content-type like header.
 
     Cargo-culted from `cgi`, but works on bytes rather than strings.
@@ -704,15 +699,16 @@ class ThreadedFileSender:
 
     def __init__(self, hs: "HomeServer") -> None:
         self.reactor = hs.get_reactor()
+        self.clock = hs.get_clock()
         self.thread_pool = hs.get_media_sender_thread_pool()
 
-        self.file: Optional[BinaryIO] = None
+        self.file: BinaryIO | None = None
         self.deferred: "Deferred[None]" = Deferred()
-        self.consumer: Optional[interfaces.IConsumer] = None
+        self.consumer: interfaces.IConsumer | None = None
 
         # Signals if the thread should keep reading/sending data. Set means
         # continue, clear means pause.
-        self.wakeup_event = DeferredEvent(self.reactor)
+        self.wakeup_event = DeferredEvent(self.clock)
 
         # Signals if the thread should terminate, e.g. because the consumer has
         # gone away.
diff --git a/synapse/media/filepath.py b/synapse/media/filepath.py
index 3d7863e2fb..df637f3be3 100644
--- a/synapse/media/filepath.py
+++ b/synapse/media/filepath.py
@@ -24,7 +24,7 @@ import functools
 import os
 import re
 import string
-from typing import Any, Callable, List, TypeVar, Union, cast
+from typing import Any, Callable, TypeVar, cast
 
 NEW_FORMAT_ID_RE = re.compile(r"^\d\d\d\d-\d\d-\d\d")
 
@@ -46,7 +46,7 @@ def _wrap_in_base_path(func: F) -> F:
 
 
 GetPathMethod = TypeVar(
-    "GetPathMethod", bound=Union[Callable[..., str], Callable[..., List[str]]]
+    "GetPathMethod", bound=Callable[..., str] | Callable[..., list[str]]
 )
 
 
@@ -73,7 +73,7 @@ def _wrap_with_jail_check(relative: bool) -> Callable[[GetPathMethod], GetPathMe
         @functools.wraps(func)
         def _wrapped(
             self: "MediaFilePaths", *args: Any, **kwargs: Any
-        ) -> Union[str, List[str]]:
+        ) -> str | list[str]:
             path_or_paths = func(self, *args, **kwargs)
 
             if isinstance(path_or_paths, list):
@@ -303,7 +303,7 @@ class MediaFilePaths:
     url_cache_filepath = _wrap_in_base_path(url_cache_filepath_rel)
 
     @_wrap_with_jail_check(relative=False)
-    def url_cache_filepath_dirs_to_delete(self, media_id: str) -> List[str]:
+    def url_cache_filepath_dirs_to_delete(self, media_id: str) -> list[str]:
         "The dirs to try and remove if we delete the media_id file"
         if NEW_FORMAT_ID_RE.match(media_id):
             return [
@@ -376,7 +376,7 @@ class MediaFilePaths:
     )
 
     @_wrap_with_jail_check(relative=False)
-    def url_cache_thumbnail_dirs_to_delete(self, media_id: str) -> List[str]:
+    def url_cache_thumbnail_dirs_to_delete(self, media_id: str) -> list[str]:
         "The dirs to try and remove if we delete the media_id thumbnails"
         # Media id is of the form <DATE><RANDOM_STRING>
         # E.g.: 2017-09-28-fsdRDt24DS234dsf
diff --git a/synapse/media/media_repository.py b/synapse/media/media_repository.py
index 436d9b7e35..7b4408b2bc 100644
--- a/synapse/media/media_repository.py
+++ b/synapse/media/media_repository.py
@@ -24,7 +24,7 @@ import logging
 import os
 import shutil
 from io import BytesIO
-from typing import IO, TYPE_CHECKING, Dict, List, Optional, Set, Tuple
+from typing import IO, TYPE_CHECKING
 
 import attr
 from matrix_common.types.mxc_uri import MXCUri
@@ -67,7 +67,6 @@ from synapse.media.media_storage import (
 from synapse.media.storage_provider import StorageProviderWrapper
 from synapse.media.thumbnailer import Thumbnailer, ThumbnailError
 from synapse.media.url_previewer import UrlPreviewer
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.storage.databases.main.media_repository import LocalMedia, RemoteMedia
 from synapse.types import UserID
 from synapse.util.async_helpers import Linearizer
@@ -110,8 +109,8 @@ class MediaRepository:
 
         self.remote_media_linearizer = Linearizer(name="media_remote", clock=self.clock)
 
-        self.recently_accessed_remotes: Set[Tuple[str, str]] = set()
-        self.recently_accessed_locals: Set[str] = set()
+        self.recently_accessed_remotes: set[tuple[str, str]] = set()
+        self.recently_accessed_locals: set[str] = set()
 
         self.federation_domain_whitelist = (
             hs.config.federation.federation_domain_whitelist
@@ -171,7 +170,7 @@ class MediaRepository:
             )
 
         if hs.config.media.url_preview_enabled:
-            self.url_previewer: Optional[UrlPreviewer] = UrlPreviewer(
+            self.url_previewer: UrlPreviewer | None = UrlPreviewer(
                 hs, self, self.media_storage
             )
         else:
@@ -187,16 +186,14 @@ class MediaRepository:
         self.media_repository_callbacks = hs.get_module_api_callbacks().media_repository
 
     def _start_update_recently_accessed(self) -> Deferred:
-        return run_as_background_process(
+        return self.hs.run_as_background_process(
             "update_recently_accessed_media",
-            self.server_name,
             self._update_recently_accessed,
         )
 
     def _start_apply_media_retention_rules(self) -> Deferred:
-        return run_as_background_process(
+        return self.hs.run_as_background_process(
             "apply_media_retention_rules",
-            self.server_name,
             self._apply_media_retention_rules,
         )
 
@@ -211,7 +208,7 @@ class MediaRepository:
             local_media, remote_media, self.clock.time_msec()
         )
 
-    def mark_recently_accessed(self, server_name: Optional[str], media_id: str) -> None:
+    def mark_recently_accessed(self, server_name: str | None, media_id: str) -> None:
         """Mark the given media as recently accessed.
 
         Args:
@@ -224,7 +221,7 @@ class MediaRepository:
             self.recently_accessed_locals.add(media_id)
 
     @trace
-    async def create_media_id(self, auth_user: UserID) -> Tuple[str, int]:
+    async def create_media_id(self, auth_user: UserID) -> tuple[str, int]:
         """Create and store a media ID for a local user and return the MXC URI and its
         expiration.
 
@@ -245,7 +242,7 @@ class MediaRepository:
         return f"mxc://{self.server_name}/{media_id}", now + self.unused_expiration_time
 
     @trace
-    async def reached_pending_media_limit(self, auth_user: UserID) -> Tuple[bool, int]:
+    async def reached_pending_media_limit(self, auth_user: UserID) -> tuple[bool, int]:
         """Check if the user is over the limit for pending media uploads.
 
         Args:
@@ -301,11 +298,11 @@ class MediaRepository:
     async def create_or_update_content(
         self,
         media_type: str,
-        upload_name: Optional[str],
+        upload_name: str | None,
         content: IO,
         content_length: int,
         auth_user: UserID,
-        media_id: Optional[str] = None,
+        media_id: str | None = None,
     ) -> MXCUri:
         """Create or update the content of the given media ID.
 
@@ -357,7 +354,7 @@ class MediaRepository:
 
         # This is the total size of media uploaded by the user in the last
         # `time_period_ms` milliseconds, or None if we haven't checked yet.
-        uploaded_media_size: Optional[int] = None
+        uploaded_media_size: int | None = None
 
         for limit in media_upload_limits:
             # We only need to check the amount of media uploaded by the user in
@@ -425,7 +422,7 @@ class MediaRepository:
 
     async def get_cached_remote_media_info(
         self, origin: str, media_id: str
-    ) -> Optional[RemoteMedia]:
+    ) -> RemoteMedia | None:
         """
         Get cached remote media info for a given origin/media ID combo. If the requested
         media is not found locally, it will not be requested over federation and the
@@ -442,7 +439,7 @@ class MediaRepository:
 
     async def get_local_media_info(
         self, request: SynapseRequest, media_id: str, max_timeout_ms: int
-    ) -> Optional[LocalMedia]:
+    ) -> LocalMedia | None:
         """Gets the info dictionary for given local media ID. If the media has
         not been uploaded yet, this function will wait up to ``max_timeout_ms``
         milliseconds for the media to be uploaded.
@@ -498,7 +495,7 @@ class MediaRepository:
         self,
         request: SynapseRequest,
         media_id: str,
-        name: Optional[str],
+        name: str | None,
         max_timeout_ms: int,
         allow_authenticated: bool = True,
         federation: bool = False,
@@ -558,7 +555,7 @@ class MediaRepository:
         request: SynapseRequest,
         server_name: str,
         media_id: str,
-        name: Optional[str],
+        name: str | None,
         max_timeout_ms: int,
         ip_address: str,
         use_federation_endpoint: bool,
@@ -699,7 +696,7 @@ class MediaRepository:
         ip_address: str,
         use_federation_endpoint: bool,
         allow_authenticated: bool,
-    ) -> Tuple[Optional[Responder], RemoteMedia]:
+    ) -> tuple[Responder | None, RemoteMedia]:
         """Looks for media in local cache, if not there then attempt to
         download from remote server.
 
@@ -1055,7 +1052,7 @@ class MediaRepository:
 
     def _get_thumbnail_requirements(
         self, media_type: str
-    ) -> Tuple[ThumbnailRequirement, ...]:
+    ) -> tuple[ThumbnailRequirement, ...]:
         scpos = media_type.find(";")
         if scpos > 0:
             media_type = media_type[:scpos]
@@ -1068,7 +1065,7 @@ class MediaRepository:
         t_height: int,
         t_method: str,
         t_type: str,
-    ) -> Optional[BytesIO]:
+    ) -> BytesIO | None:
         m_width = thumbnailer.width
         m_height = thumbnailer.height
 
@@ -1102,7 +1099,7 @@ class MediaRepository:
         t_method: str,
         t_type: str,
         url_cache: bool,
-    ) -> Optional[Tuple[str, FileInfo]]:
+    ) -> tuple[str, FileInfo] | None:
         input_path = await self.media_storage.ensure_media_is_in_local_cache(
             FileInfo(None, media_id, url_cache=url_cache)
         )
@@ -1178,7 +1175,7 @@ class MediaRepository:
         t_height: int,
         t_method: str,
         t_type: str,
-    ) -> Optional[str]:
+    ) -> str | None:
         input_path = await self.media_storage.ensure_media_is_in_local_cache(
             FileInfo(server_name, file_id)
         )
@@ -1250,12 +1247,12 @@ class MediaRepository:
     @trace
     async def _generate_thumbnails(
         self,
-        server_name: Optional[str],
+        server_name: str | None,
         media_id: str,
         file_id: str,
         media_type: str,
         url_cache: bool = False,
-    ) -> Optional[dict]:
+    ) -> dict | None:
         """Generate and store thumbnails for an image.
 
         Args:
@@ -1311,7 +1308,7 @@ class MediaRepository:
 
             # We deduplicate the thumbnail sizes by ignoring the cropped versions if
             # they have the same dimensions of a scaled one.
-            thumbnails: Dict[Tuple[int, int, str], str] = {}
+            thumbnails: dict[tuple[int, int, str], str] = {}
             for requirement in requirements:
                 if requirement.method == "crop":
                     thumbnails.setdefault(
@@ -1464,7 +1461,7 @@ class MediaRepository:
                 delete_protected_media=False,
             )
 
-    async def delete_old_remote_media(self, before_ts: int) -> Dict[str, int]:
+    async def delete_old_remote_media(self, before_ts: int) -> dict[str, int]:
         old_media = await self.store.get_remote_media_ids(
             before_ts, include_quarantined_media=False
         )
@@ -1500,8 +1497,8 @@ class MediaRepository:
         return {"deleted": deleted}
 
     async def delete_local_media_ids(
-        self, media_ids: List[str]
-    ) -> Tuple[List[str], int]:
+        self, media_ids: list[str]
+    ) -> tuple[list[str], int]:
         """
         Delete the given local or remote media ID from this server
 
@@ -1519,7 +1516,7 @@ class MediaRepository:
         keep_profiles: bool = True,
         delete_quarantined_media: bool = False,
         delete_protected_media: bool = False,
-    ) -> Tuple[List[str], int]:
+    ) -> tuple[list[str], int]:
         """
         Delete local or remote media from this server by size and timestamp. Removes
         media files, any thumbnails and cached URLs.
@@ -1546,8 +1543,8 @@ class MediaRepository:
         return await self._remove_local_media_from_disk(old_media)
 
     async def _remove_local_media_from_disk(
-        self, media_ids: List[str]
-    ) -> Tuple[List[str], int]:
+        self, media_ids: list[str]
+    ) -> tuple[list[str], int]:
         """
         Delete local or remote media from this server. Removes media files,
         any thumbnails and cached URLs.
diff --git a/synapse/media/media_storage.py b/synapse/media/media_storage.py
index 99d002a8df..bc12212c46 100644
--- a/synapse/media/media_storage.py
+++ b/synapse/media/media_storage.py
@@ -34,12 +34,7 @@ from typing import (
     AsyncIterator,
     BinaryIO,
     Callable,
-    List,
-    Optional,
     Sequence,
-    Tuple,
-    Type,
-    Union,
     cast,
 )
 from uuid import uuid4
@@ -82,7 +77,7 @@ class SHA256TransparentIOWriter:
         self._hash = hashlib.sha256()
         self._source = source
 
-    def write(self, buffer: Union[bytes, bytearray]) -> int:
+    def write(self, buffer: bytes | bytearray) -> int:
         """Wrapper for source.write()
 
         Args:
@@ -205,7 +200,7 @@ class MediaStorage:
     @contextlib.asynccontextmanager
     async def store_into_file(
         self, file_info: FileInfo
-    ) -> AsyncIterator[Tuple[BinaryIO, str]]:
+    ) -> AsyncIterator[tuple[BinaryIO, str]]:
         """Async Context manager used to get a file like object to write into, as
         described by file_info.
 
@@ -263,7 +258,7 @@ class MediaStorage:
 
             raise e from None
 
-    async def fetch_media(self, file_info: FileInfo) -> Optional[Responder]:
+    async def fetch_media(self, file_info: FileInfo) -> Responder | None:
         """Attempts to fetch media described by file_info from the local cache
         and configured storage providers.
 
@@ -423,9 +418,9 @@ class FileResponder(Responder):
 
     def __exit__(
         self,
-        exc_type: Optional[Type[BaseException]],
-        exc_val: Optional[BaseException],
-        exc_tb: Optional[TracebackType],
+        exc_type: type[BaseException] | None,
+        exc_val: BaseException | None,
+        exc_tb: TracebackType | None,
     ) -> None:
         self.open_file.close()
 
@@ -479,7 +474,7 @@ class MultipartFileConsumer:
         file_content_type: str,
         json_object: JsonDict,
         disposition: str,
-        content_length: Optional[int],
+        content_length: int | None,
     ) -> None:
         self.clock = clock
         self.wrapped_consumer = wrapped_consumer
@@ -491,8 +486,8 @@ class MultipartFileConsumer:
 
         # The producer that registered with us, and if it's a push or pull
         # producer.
-        self.producer: Optional["interfaces.IProducer"] = None
-        self.streaming: Optional[bool] = None
+        self.producer: "interfaces.IProducer" | None = None
+        self.streaming: bool | None = None
 
         # Whether the wrapped consumer has asked us to pause.
         self.paused = False
@@ -621,7 +616,7 @@ class MultipartFileConsumer:
             # repeatedly calling  `resumeProducing` in a loop.
             run_in_background(self._resumeProducingRepeatedly)
 
-    def content_length(self) -> Optional[int]:
+    def content_length(self) -> int | None:
         """
         Calculate the content length of the multipart response
         in bytes.
@@ -674,7 +669,7 @@ class Header:
         self,
         name: bytes,
         value: Any,
-        params: Optional[List[Tuple[Any, Any]]] = None,
+        params: list[tuple[Any, Any]] | None = None,
     ):
         self.name = name
         self.value = value
@@ -696,7 +691,7 @@ class Header:
             return h.read()
 
 
-def escape(value: Union[str, bytes]) -> str:
+def escape(value: str | bytes) -> str:
     """
     This function prevents header values from corrupting the request,
     a newline in the file name parameter makes form-data request unreadable
diff --git a/synapse/media/oembed.py b/synapse/media/oembed.py
index 45b481f229..7e44072130 100644
--- a/synapse/media/oembed.py
+++ b/synapse/media/oembed.py
@@ -21,7 +21,7 @@
 import html
 import logging
 import urllib.parse
-from typing import TYPE_CHECKING, List, Optional, cast
+from typing import TYPE_CHECKING, cast
 
 import attr
 
@@ -42,12 +42,12 @@ class OEmbedResult:
     # The Open Graph result (converted from the oEmbed result).
     open_graph_result: JsonDict
     # The author_name of the oEmbed result
-    author_name: Optional[str]
+    author_name: str | None
     # Number of milliseconds to cache the content, according to the oEmbed response.
     #
     # This will be None if no cache-age is provided in the oEmbed response (or
     # if the oEmbed response cannot be turned into an Open Graph response).
-    cache_age: Optional[int]
+    cache_age: int | None
 
 
 class OEmbedProvider:
@@ -80,7 +80,7 @@ class OEmbedProvider:
             for pattern in oembed_endpoint.url_patterns:
                 self._oembed_patterns[pattern] = api_endpoint
 
-    def get_oembed_url(self, url: str) -> Optional[str]:
+    def get_oembed_url(self, url: str) -> str | None:
         """
         Check whether the URL should be downloaded as oEmbed content instead.
 
@@ -105,7 +105,7 @@ class OEmbedProvider:
         # No match.
         return None
 
-    def autodiscover_from_html(self, tree: "etree._Element") -> Optional[str]:
+    def autodiscover_from_html(self, tree: "etree._Element") -> str | None:
         """
         Search an HTML document for oEmbed autodiscovery information.
 
@@ -118,7 +118,7 @@ class OEmbedProvider:
         # Search for link elements with the proper rel and type attributes.
         # Cast: the type returned by xpath depends on the xpath expression: mypy can't deduce this.
         for tag in cast(
-            List["etree._Element"],
+            list["etree._Element"],
             tree.xpath("//link[@rel='alternate'][@type='application/json+oembed']"),
         ):
             if "href" in tag.attrib:
@@ -127,7 +127,7 @@ class OEmbedProvider:
         # Some providers (e.g. Flickr) use alternative instead of alternate.
         # Cast: the type returned by xpath depends on the xpath expression: mypy can't deduce this.
         for tag in cast(
-            List["etree._Element"],
+            list["etree._Element"],
             tree.xpath("//link[@rel='alternative'][@type='application/json+oembed']"),
         ):
             if "href" in tag.attrib:
@@ -223,10 +223,10 @@ class OEmbedProvider:
         return OEmbedResult(open_graph_response, author_name, cache_age)
 
 
-def _fetch_urls(tree: "etree._Element", tag_name: str) -> List[str]:
+def _fetch_urls(tree: "etree._Element", tag_name: str) -> list[str]:
     results = []
     # Cast: the type returned by xpath depends on the xpath expression: mypy can't deduce this.
-    for tag in cast(List["etree._Element"], tree.xpath("//*/" + tag_name)):
+    for tag in cast(list["etree._Element"], tree.xpath("//*/" + tag_name)):
         if "src" in tag.attrib:
             results.append(cast(str, tag.attrib["src"]))
     return results
diff --git a/synapse/media/preview_html.py b/synapse/media/preview_html.py
index 38ae126a23..22ad581f82 100644
--- a/synapse/media/preview_html.py
+++ b/synapse/media/preview_html.py
@@ -24,13 +24,9 @@ import re
 from typing import (
     TYPE_CHECKING,
     Callable,
-    Dict,
     Generator,
     Iterable,
-    List,
     Optional,
-    Set,
-    Union,
     cast,
 )
 
@@ -51,7 +47,7 @@ _content_type_match = re.compile(r'.*; *charset="?(.*?)"?(;|$)', flags=re.I)
 ARIA_ROLES_TO_IGNORE = {"directory", "menu", "menubar", "toolbar"}
 
 
-def _normalise_encoding(encoding: str) -> Optional[str]:
+def _normalise_encoding(encoding: str) -> str | None:
     """Use the Python codec's name as the normalised entry."""
     try:
         return codecs.lookup(encoding).name
@@ -59,9 +55,7 @@ def _normalise_encoding(encoding: str) -> Optional[str]:
         return None
 
 
-def _get_html_media_encodings(
-    body: bytes, content_type: Optional[str]
-) -> Iterable[str]:
+def _get_html_media_encodings(body: bytes, content_type: str | None) -> Iterable[str]:
     """
     Get potential encoding of the body based on the (presumably) HTML body or the content-type header.
 
@@ -83,7 +77,7 @@ def _get_html_media_encodings(
         The character encoding of the body, as a string.
     """
     # There's no point in returning an encoding more than once.
-    attempted_encodings: Set[str] = set()
+    attempted_encodings: set[str] = set()
 
     # Limit searches to the first 1kb, since it ought to be at the top.
     body_start = body[:1024]
@@ -122,7 +116,7 @@ def _get_html_media_encodings(
 
 
 def decode_body(
-    body: bytes, uri: str, content_type: Optional[str] = None
+    body: bytes, uri: str, content_type: str | None = None
 ) -> Optional["etree._Element"]:
     """
     This uses lxml to parse the HTML document.
@@ -189,8 +183,8 @@ def _get_meta_tags(
     tree: "etree._Element",
     property: str,
     prefix: str,
-    property_mapper: Optional[Callable[[str], Optional[str]]] = None,
-) -> Dict[str, Optional[str]]:
+    property_mapper: Callable[[str], str | None] | None = None,
+) -> dict[str, str | None]:
     """
     Search for meta tags prefixed with a particular string.
 
@@ -205,12 +199,12 @@ def _get_meta_tags(
     Returns:
         A map of tag name to value.
     """
-    # This actually returns Dict[str, str], but the caller sets this as a variable
-    # which is Dict[str, Optional[str]].
-    results: Dict[str, Optional[str]] = {}
+    # This actually returns dict[str, str], but the caller sets this as a variable
+    # which is dict[str, str | None].
+    results: dict[str, str | None] = {}
     # Cast: the type returned by xpath depends on the xpath expression: mypy can't deduce this.
     for tag in cast(
-        List["etree._Element"],
+        list["etree._Element"],
         tree.xpath(
             f"//*/meta[starts-with(@{property}, '{prefix}:')][@content][not(@content='')]"
         ),
@@ -236,7 +230,7 @@ def _get_meta_tags(
     return results
 
 
-def _map_twitter_to_open_graph(key: str) -> Optional[str]:
+def _map_twitter_to_open_graph(key: str) -> str | None:
     """
     Map a Twitter card property to the analogous Open Graph property.
 
@@ -256,7 +250,7 @@ def _map_twitter_to_open_graph(key: str) -> Optional[str]:
     return "og" + key[7:]
 
 
-def parse_html_to_open_graph(tree: "etree._Element") -> Dict[str, Optional[str]]:
+def parse_html_to_open_graph(tree: "etree._Element") -> dict[str, str | None]:
     """
     Parse the HTML document into an Open Graph response.
 
@@ -315,7 +309,7 @@ def parse_html_to_open_graph(tree: "etree._Element") -> Dict[str, Optional[str]]
         # Attempt to find a title from the title tag, or the biggest header on the page.
         # Cast: the type returned by xpath depends on the xpath expression: mypy can't deduce this.
         title = cast(
-            List["etree._ElementUnicodeResult"],
+            list["etree._ElementUnicodeResult"],
             tree.xpath("((//title)[1] | (//h1)[1] | (//h2)[1] | (//h3)[1])/text()"),
         )
         if title:
@@ -326,7 +320,7 @@ def parse_html_to_open_graph(tree: "etree._Element") -> Dict[str, Optional[str]]
     if "og:image" not in og:
         # Cast: the type returned by xpath depends on the xpath expression: mypy can't deduce this.
         meta_image = cast(
-            List["etree._ElementUnicodeResult"],
+            list["etree._ElementUnicodeResult"],
             tree.xpath(
                 "//*/meta[translate(@itemprop, 'IMAGE', 'image')='image'][not(@content='')]/@content[1]"
             ),
@@ -340,7 +334,7 @@ def parse_html_to_open_graph(tree: "etree._Element") -> Dict[str, Optional[str]]
             #
             # TODO: consider inlined CSS styles as well as width & height attribs
             images = cast(
-                List["etree._Element"],
+                list["etree._Element"],
                 tree.xpath("//img[@src][number(@width)>10][number(@height)>10]"),
             )
             images = sorted(
@@ -352,7 +346,7 @@ def parse_html_to_open_graph(tree: "etree._Element") -> Dict[str, Optional[str]]
             # If no images were found, try to find *any* images.
             if not images:
                 # Cast: the type returned by xpath depends on the xpath expression: mypy can't deduce this.
-                images = cast(List["etree._Element"], tree.xpath("//img[@src][1]"))
+                images = cast(list["etree._Element"], tree.xpath("//img[@src][1]"))
             if images:
                 og["og:image"] = cast(str, images[0].attrib["src"])
 
@@ -360,7 +354,7 @@ def parse_html_to_open_graph(tree: "etree._Element") -> Dict[str, Optional[str]]
             else:
                 # Cast: the type returned by xpath depends on the xpath expression: mypy can't deduce this.
                 favicons = cast(
-                    List["etree._ElementUnicodeResult"],
+                    list["etree._ElementUnicodeResult"],
                     tree.xpath("//link[@href][contains(@rel, 'icon')]/@href[1]"),
                 )
                 if favicons:
@@ -370,7 +364,7 @@ def parse_html_to_open_graph(tree: "etree._Element") -> Dict[str, Optional[str]]
         # Check the first meta description tag for content.
         # Cast: the type returned by xpath depends on the xpath expression: mypy can't deduce this.
         meta_description = cast(
-            List["etree._ElementUnicodeResult"],
+            list["etree._ElementUnicodeResult"],
             tree.xpath(
                 "//*/meta[translate(@name, 'DESCRIPTION', 'description')='description'][not(@content='')]/@content[1]"
             ),
@@ -390,7 +384,7 @@ def parse_html_to_open_graph(tree: "etree._Element") -> Dict[str, Optional[str]]
     return og
 
 
-def parse_html_description(tree: "etree._Element") -> Optional[str]:
+def parse_html_description(tree: "etree._Element") -> str | None:
     """
     Calculate a text description based on an HTML document.
 
@@ -443,7 +437,7 @@ def parse_html_description(tree: "etree._Element") -> Optional[str]:
 
 def _iterate_over_text(
     tree: Optional["etree._Element"],
-    tags_to_ignore: Set[object],
+    tags_to_ignore: set[object],
     stack_limit: int = 1024,
 ) -> Generator[str, None, None]:
     """Iterate over the tree returning text nodes in a depth first fashion,
@@ -463,7 +457,7 @@ def _iterate_over_text(
 
     # This is a stack whose items are elements to iterate over *or* strings
     # to be returned.
-    elements: List[Union[str, "etree._Element"]] = [tree]
+    elements: list[str | "etree._Element"] = [tree]
     while elements:
         el = elements.pop()
 
@@ -499,7 +493,7 @@ def _iterate_over_text(
 
 def summarize_paragraphs(
     text_nodes: Iterable[str], min_size: int = 200, max_size: int = 500
-) -> Optional[str]:
+) -> str | None:
     """
     Try to get a summary respecting first paragraph and then word boundaries.
 
diff --git a/synapse/media/storage_provider.py b/synapse/media/storage_provider.py
index 300952025a..a87ffa0892 100644
--- a/synapse/media/storage_provider.py
+++ b/synapse/media/storage_provider.py
@@ -23,7 +23,7 @@ import abc
 import logging
 import os
 import shutil
-from typing import TYPE_CHECKING, Callable, Optional
+from typing import TYPE_CHECKING, Callable
 
 from synapse.config._base import Config
 from synapse.logging.context import defer_to_thread, run_in_background
@@ -55,7 +55,7 @@ class StorageProvider(metaclass=abc.ABCMeta):
         """
 
     @abc.abstractmethod
-    async def fetch(self, path: str, file_info: FileInfo) -> Optional[Responder]:
+    async def fetch(self, path: str, file_info: FileInfo) -> Responder | None:
         """Attempt to fetch the file described by file_info and stream it
         into writer.
 
@@ -124,7 +124,7 @@ class StorageProviderWrapper(StorageProvider):
             run_in_background(store)
 
     @trace_with_opname("StorageProviderWrapper.fetch")
-    async def fetch(self, path: str, file_info: FileInfo) -> Optional[Responder]:
+    async def fetch(self, path: str, file_info: FileInfo) -> Responder | None:
         if file_info.url_cache:
             # Files in the URL preview cache definitely aren't stored here,
             # so avoid any potentially slow I/O or network access.
@@ -173,7 +173,7 @@ class FileStorageProviderBackend(StorageProvider):
             )
 
     @trace_with_opname("FileStorageProviderBackend.fetch")
-    async def fetch(self, path: str, file_info: FileInfo) -> Optional[Responder]:
+    async def fetch(self, path: str, file_info: FileInfo) -> Responder | None:
         """See StorageProvider.fetch"""
 
         backup_fname = os.path.join(self.base_directory, path)
diff --git a/synapse/media/thumbnailer.py b/synapse/media/thumbnailer.py
index 5d9afda322..fd65131c63 100644
--- a/synapse/media/thumbnailer.py
+++ b/synapse/media/thumbnailer.py
@@ -22,7 +22,7 @@
 import logging
 from io import BytesIO
 from types import TracebackType
-from typing import TYPE_CHECKING, List, Optional, Tuple, Type
+from typing import TYPE_CHECKING
 
 from PIL import Image
 
@@ -97,16 +97,7 @@ class Thumbnailer:
         self.transpose_method = None
         try:
             # We don't use ImageOps.exif_transpose since it crashes with big EXIF
-            #
-            # Ignore safety: Pillow seems to acknowledge that this method is
-            # "private, experimental, but generally widely used". Pillow 6
-            # includes a public getexif() method (no underscore) that we might
-            # consider using instead when we can bump that dependency.
-            #
-            # At the time of writing, Debian buster (currently oldstable)
-            # provides version 5.4.1. It's expected to EOL in mid-2022, see
-            # https://wiki.debian.org/DebianReleases#Production_Releases
-            image_exif = self.image._getexif()  # type: ignore
+            image_exif = self.image.getexif()
             if image_exif is not None:
                 image_orientation = image_exif.get(EXIF_ORIENTATION_TAG)
                 assert type(image_orientation) is int  # noqa: E721
@@ -116,7 +107,7 @@ class Thumbnailer:
             logger.info("Error parsing image EXIF information: %s", e)
 
     @trace
-    def transpose(self) -> Tuple[int, int]:
+    def transpose(self) -> tuple[int, int]:
         """Transpose the image using its EXIF Orientation tag
 
         Returns:
@@ -134,7 +125,7 @@ class Thumbnailer:
             self.image.info["exif"] = None
         return self.image.size
 
-    def aspect(self, max_width: int, max_height: int) -> Tuple[int, int]:
+    def aspect(self, max_width: int, max_height: int) -> tuple[int, int]:
         """Calculate the largest size that preserves aspect ratio which
         fits within the given rectangle::
 
@@ -246,9 +237,9 @@ class Thumbnailer:
 
     def __exit__(
         self,
-        type: Optional[Type[BaseException]],
-        value: Optional[BaseException],
-        traceback: Optional[TracebackType],
+        type: type[BaseException] | None,
+        value: BaseException | None,
+        traceback: TracebackType | None,
     ) -> None:
         self.close()
 
@@ -553,13 +544,13 @@ class ThumbnailProvider:
         desired_height: int,
         desired_method: str,
         desired_type: str,
-        thumbnail_infos: List[ThumbnailInfo],
+        thumbnail_infos: list[ThumbnailInfo],
         media_id: str,
         file_id: str,
         url_cache: bool,
         for_federation: bool,
-        media_info: Optional[LocalMedia] = None,
-        server_name: Optional[str] = None,
+        media_info: LocalMedia | None = None,
+        server_name: str | None = None,
     ) -> None:
         """
         Respond to a request with an appropriate thumbnail from the previously generated thumbnails.
@@ -719,11 +710,11 @@ class ThumbnailProvider:
         desired_height: int,
         desired_method: str,
         desired_type: str,
-        thumbnail_infos: List[ThumbnailInfo],
+        thumbnail_infos: list[ThumbnailInfo],
         file_id: str,
         url_cache: bool,
-        server_name: Optional[str],
-    ) -> Optional[FileInfo]:
+        server_name: str | None,
+    ) -> FileInfo | None:
         """
         Choose an appropriate thumbnail from the previously generated thumbnails.
 
@@ -750,12 +741,12 @@ class ThumbnailProvider:
 
         if desired_method == "crop":
             # Thumbnails that match equal or larger sizes of desired width/height.
-            crop_info_list: List[
-                Tuple[int, int, int, bool, Optional[int], ThumbnailInfo]
+            crop_info_list: list[
+                tuple[int, int, int, bool, int | None, ThumbnailInfo]
             ] = []
             # Other thumbnails.
-            crop_info_list2: List[
-                Tuple[int, int, int, bool, Optional[int], ThumbnailInfo]
+            crop_info_list2: list[
+                tuple[int, int, int, bool, int | None, ThumbnailInfo]
             ] = []
             for info in thumbnail_infos:
                 # Skip thumbnails generated with different methods.
@@ -801,9 +792,9 @@ class ThumbnailProvider:
                 thumbnail_info = min(crop_info_list2, key=lambda t: t[:-1])[-1]
         elif desired_method == "scale":
             # Thumbnails that match equal or larger sizes of desired width/height.
-            info_list: List[Tuple[int, bool, int, ThumbnailInfo]] = []
+            info_list: list[tuple[int, bool, int, ThumbnailInfo]] = []
             # Other thumbnails.
-            info_list2: List[Tuple[int, bool, int, ThumbnailInfo]] = []
+            info_list2: list[tuple[int, bool, int, ThumbnailInfo]] = []
 
             for info in thumbnail_infos:
                 # Skip thumbnails generated with different methods.
diff --git a/synapse/media/url_previewer.py b/synapse/media/url_previewer.py
index 81204913f7..bbd8017b13 100644
--- a/synapse/media/url_previewer.py
+++ b/synapse/media/url_previewer.py
@@ -28,7 +28,7 @@ import re
 import shutil
 import sys
 import traceback
-from typing import TYPE_CHECKING, BinaryIO, Iterable, Optional, Tuple
+from typing import TYPE_CHECKING, BinaryIO, Iterable
 from urllib.parse import urljoin, urlparse, urlsplit
 from urllib.request import urlopen
 
@@ -44,7 +44,6 @@ from synapse.media._base import FileInfo, get_filename_from_headers
 from synapse.media.media_storage import MediaStorage, SHA256TransparentIOWriter
 from synapse.media.oembed import OEmbedProvider
 from synapse.media.preview_html import decode_body, parse_html_to_open_graph
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.types import JsonDict, UserID
 from synapse.util.async_helpers import ObservableDeferred
 from synapse.util.caches.expiringcache import ExpiringCache
@@ -71,9 +70,9 @@ class DownloadResult:
     uri: str
     response_code: int
     media_type: str
-    download_name: Optional[str]
+    download_name: str | None
     expires: int
-    etag: Optional[str]
+    etag: str | None
 
 
 @attr.s(slots=True, frozen=True, auto_attribs=True)
@@ -88,7 +87,7 @@ class MediaInfo:
     media_length: int
     # The media filename, according to the server. This is parsed from the
     # returned headers, if possible.
-    download_name: Optional[str]
+    download_name: str | None
     # The time of the preview.
     created_ts_ms: int
     # Information from the media storage provider about where the file is stored
@@ -102,7 +101,7 @@ class MediaInfo:
     # The timestamp (in milliseconds) of when this preview expires.
     expires: int
     # The ETag header of the response.
-    etag: Optional[str]
+    etag: str | None
 
 
 class UrlPreviewer:
@@ -167,6 +166,7 @@ class UrlPreviewer:
         media_storage: MediaStorage,
     ):
         self.clock = hs.get_clock()
+        self.hs = hs
         self.filepaths = media_repo.filepaths
         self.max_spider_size = hs.config.media.max_spider_size
         self.server_name = hs.hostname
@@ -201,15 +201,14 @@ class UrlPreviewer:
         self._cache: ExpiringCache[str, ObservableDeferred] = ExpiringCache(
             cache_name="url_previews",
             server_name=self.server_name,
+            hs=self.hs,
             clock=self.clock,
             # don't spider URLs more often than once an hour
             expiry_ms=ONE_HOUR,
         )
 
         if self._worker_run_media_background_jobs:
-            self._cleaner_loop = self.clock.looping_call(
-                self._start_expire_url_cache_data, 10 * 1000
-            )
+            self.clock.looping_call(self._start_expire_url_cache_data, 10 * 1000)
 
     async def preview(self, url: str, user: UserID, ts: int) -> bytes:
         # the in-memory cache:
@@ -269,7 +268,7 @@ class UrlPreviewer:
 
         # The number of milliseconds that the response should be considered valid.
         expiration_ms = media_info.expires
-        author_name: Optional[str] = None
+        author_name: str | None = None
 
         if _is_media(media_info.media_type):
             file_id = media_info.filesystem_id
@@ -706,7 +705,7 @@ class UrlPreviewer:
 
     async def _handle_oembed_response(
         self, url: str, media_info: MediaInfo, expiration_ms: int
-    ) -> Tuple[JsonDict, Optional[str], int]:
+    ) -> tuple[JsonDict, str | None, int]:
         """
         Parse the downloaded oEmbed info.
 
@@ -739,8 +738,8 @@ class UrlPreviewer:
         return open_graph_result, oembed_response.author_name, expiration_ms
 
     def _start_expire_url_cache_data(self) -> Deferred:
-        return run_as_background_process(
-            "expire_url_cache_data", self.server_name, self._expire_url_cache_data
+        return self.hs.run_as_background_process(
+            "expire_url_cache_data", self._expire_url_cache_data
         )
 
     async def _expire_url_cache_data(self) -> None:
diff --git a/synapse/metrics/__init__.py b/synapse/metrics/__init__.py
index 2ffb14070b..cf7b2f1da0 100644
--- a/synapse/metrics/__init__.py
+++ b/synapse/metrics/__init__.py
@@ -28,17 +28,11 @@ import threading
 from importlib import metadata
 from typing import (
     Callable,
-    Dict,
     Generic,
     Iterable,
     Mapping,
-    Optional,
     Sequence,
-    Set,
-    Tuple,
-    Type,
     TypeVar,
-    Union,
     cast,
 )
 
@@ -160,12 +154,10 @@ class LaterGauge(Collector):
 
     name: str
     desc: str
-    labelnames: Optional[StrSequence] = attr.ib(hash=False)
-    _instance_id_to_hook_map: Dict[
-        Optional[str],  # instance_id
-        Callable[
-            [], Union[Mapping[Tuple[str, ...], Union[int, float]], Union[int, float]]
-        ],
+    labelnames: StrSequence | None = attr.ib(hash=False)
+    _instance_id_to_hook_map: dict[
+        str | None,  # instance_id
+        Callable[[], Mapping[tuple[str, ...], int | float] | int | float],
     ] = attr.ib(factory=dict, hash=False)
     """
     Map from homeserver instance_id to a callback. Each callback should either return a
@@ -204,10 +196,8 @@ class LaterGauge(Collector):
     def register_hook(
         self,
         *,
-        homeserver_instance_id: Optional[str],
-        hook: Callable[
-            [], Union[Mapping[Tuple[str, ...], Union[int, float]], Union[int, float]]
-        ],
+        homeserver_instance_id: str | None,
+        hook: Callable[[], Mapping[tuple[str, ...], int | float] | int | float],
     ) -> None:
         """
         Register a callback/hook that will be called to generate a metric samples for
@@ -260,7 +250,7 @@ class LaterGauge(Collector):
         all_later_gauges_to_clean_up_on_shutdown[self.name] = self
 
 
-all_later_gauges_to_clean_up_on_shutdown: Dict[str, LaterGauge] = {}
+all_later_gauges_to_clean_up_on_shutdown: dict[str, LaterGauge] = {}
 """
 Track all `LaterGauge` instances so we can remove any associated hooks during homeserver
 shutdown.
@@ -302,15 +292,15 @@ class InFlightGauge(Generic[MetricsEntry], Collector):
 
         # Create a class which have the sub_metrics values as attributes, which
         # default to 0 on initialization. Used to pass to registered callbacks.
-        self._metrics_class: Type[MetricsEntry] = attr.make_class(
+        self._metrics_class: type[MetricsEntry] = attr.make_class(
             "_MetricsEntry",
             attrs={x: attr.ib(default=0) for x in sub_metrics},
             slots=True,
         )
 
         # Counts number of in flight blocks for a given set of label values
-        self._registrations: Dict[
-            Tuple[str, ...], Set[Callable[[MetricsEntry], None]]
+        self._registrations: dict[
+            tuple[str, ...], set[Callable[[MetricsEntry], None]]
         ] = {}
 
         # Protects access to _registrations
@@ -320,7 +310,7 @@ class InFlightGauge(Generic[MetricsEntry], Collector):
 
     def register(
         self,
-        key: Tuple[str, ...],
+        key: tuple[str, ...],
         callback: Callable[[MetricsEntry], None],
     ) -> None:
         """Registers that we've entered a new block with labels `key`.
@@ -349,7 +339,7 @@ class InFlightGauge(Generic[MetricsEntry], Collector):
 
     def unregister(
         self,
-        key: Tuple[str, ...],
+        key: tuple[str, ...],
         callback: Callable[[MetricsEntry], None],
     ) -> None:
         """
@@ -424,7 +414,7 @@ class GaugeHistogramMetricFamilyWithLabels(GaugeHistogramMetricFamily):
         name: str,
         documentation: str,
         gsum_value: float,
-        buckets: Optional[Sequence[Tuple[str, float]]] = None,
+        buckets: Sequence[tuple[str, float]] | None = None,
         labelnames: StrSequence = (),
         labelvalues: StrSequence = (),
         unit: str = "",
@@ -475,7 +465,7 @@ class GaugeBucketCollector(Collector):
         *,
         name: str,
         documentation: str,
-        labelnames: Optional[StrSequence],
+        labelnames: StrSequence | None,
         buckets: Iterable[float],
         registry: CollectorRegistry = REGISTRY,
     ):
@@ -501,7 +491,7 @@ class GaugeBucketCollector(Collector):
 
         # We initially set this to None. We won't report metrics until
         # this has been initialised after a successful data update
-        self._metric: Optional[GaugeHistogramMetricFamilyWithLabels] = None
+        self._metric: GaugeHistogramMetricFamilyWithLabels | None = None
 
         registry.register(self)
 
diff --git a/synapse/metrics/_gc.py b/synapse/metrics/_gc.py
index e7783b05e6..1da871f18f 100644
--- a/synapse/metrics/_gc.py
+++ b/synapse/metrics/_gc.py
@@ -138,7 +138,9 @@ def install_gc_manager() -> None:
                 gc_time.labels(i).observe(end - start)
                 gc_unreachable.labels(i).set(unreachable)
 
-    gc_task = task.LoopingCall(_maybe_gc)
+    # We can ignore the lint here since this looping call does not hold a `HomeServer`
+    # reference so can be cleaned up by other means on shutdown.
+    gc_task = task.LoopingCall(_maybe_gc)  # type: ignore[prefer-synapse-clock-looping-call]
     gc_task.start(0.1)
 
 
diff --git a/synapse/metrics/background_process_metrics.py b/synapse/metrics/background_process_metrics.py
index 93345b0e9d..8ff2803455 100644
--- a/synapse/metrics/background_process_metrics.py
+++ b/synapse/metrics/background_process_metrics.py
@@ -29,15 +29,11 @@ from typing import (
     Awaitable,
     Callable,
     ContextManager,
-    Dict,
     Generator,
     Iterable,
     Optional,
     Protocol,
-    Set,
-    Type,
     TypeVar,
-    Union,
 )
 
 from prometheus_client import Metric
@@ -66,6 +62,13 @@ if TYPE_CHECKING:
     # Old versions don't have `LiteralString`
     from typing_extensions import LiteralString
 
+    from synapse.server import HomeServer
+
+    try:
+        import opentracing
+    except ImportError:
+        opentracing = None  # type: ignore[assignment]
+
 
 logger = logging.getLogger(__name__)
 
@@ -127,7 +130,7 @@ _background_process_db_sched_duration = Counter(
 # map from description to a counter, so that we can name our logcontexts
 # incrementally. (It actually duplicates _background_process_start_count, but
 # it's much simpler to do so than to try to combine them.)
-_background_process_counts: Dict[str, int] = {}
+_background_process_counts: dict[str, int] = {}
 
 # Set of all running background processes that became active active since the
 # last time metrics were scraped (i.e. background processes that performed some
@@ -137,7 +140,7 @@ _background_process_counts: Dict[str, int] = {}
 # background processes stacking up behind a lock or linearizer, where we then
 # only need to iterate over and update metrics for the process that have
 # actually been active and can ignore the idle ones.
-_background_processes_active_since_last_scrape: "Set[_BackgroundProcess]" = set()
+_background_processes_active_since_last_scrape: "set[_BackgroundProcess]" = set()
 
 # A lock that covers the above set and dict
 _bg_metrics_lock = threading.Lock()
@@ -184,7 +187,7 @@ class _BackgroundProcess:
         self.desc = desc
         self.server_name = server_name
         self._context = ctx
-        self._reported_stats: Optional[ContextResourceUsage] = None
+        self._reported_stats: ContextResourceUsage | None = None
 
     def update_metrics(self) -> None:
         """Updates the metrics with values from this process."""
@@ -220,11 +223,12 @@ R = TypeVar("R")
 def run_as_background_process(
     desc: "LiteralString",
     server_name: str,
-    func: Callable[..., Awaitable[Optional[R]]],
+    func: Callable[..., Awaitable[R | None]],
     *args: Any,
     bg_start_span: bool = True,
+    test_only_tracer: Optional["opentracing.Tracer"] = None,
     **kwargs: Any,
-) -> "defer.Deferred[Optional[R]]":
+) -> "defer.Deferred[R | None]":
     """Run the given function in its own logcontext, with resource metrics
 
     This should be used to wrap processes which are fired off to run in the
@@ -248,6 +252,8 @@ def run_as_background_process(
         bg_start_span: Whether to start an opentracing span. Defaults to True.
             Should only be disabled for processes that will not log to or tag
             a span.
+        test_only_tracer: Set the OpenTracing tracer to use. This is only useful for
+            tests.
         args: positional args for func
         kwargs: keyword args for func
 
@@ -257,7 +263,13 @@ def run_as_background_process(
         rules.
     """
 
-    async def run() -> Optional[R]:
+    # Since we track the tracing scope in the `LoggingContext`, before we move to the
+    # sentinel logcontext (or a new `LoggingContext`), grab the currently active
+    # tracing span (if any) so that we can create a cross-link to the background process
+    # trace.
+    original_active_tracing_span = active_span(tracer=test_only_tracer)
+
+    async def run() -> R | None:
         with _bg_metrics_lock:
             count = _background_process_counts.get(desc, 0)
             _background_process_counts[desc] = count + 1
@@ -274,8 +286,6 @@ def run_as_background_process(
         ) as logging_context:
             try:
                 if bg_start_span:
-                    original_active_tracing_span = active_span()
-
                     # If there is already an active span (e.g. because this background
                     # process was started as part of handling a request for example),
                     # because this is a long-running background task that may serve a
@@ -306,6 +316,7 @@ def run_as_background_process(
                             # Create a root span for the background process (disconnected
                             # from other spans)
                             ignore_active_span=True,
+                            tracer=test_only_tracer,
                         )
 
                         # Also add a span in the original request trace that cross-links
@@ -322,8 +333,11 @@ def run_as_background_process(
                             f"start_bgproc.{desc}",
                             child_of=original_active_tracing_span,
                             ignore_active_span=True,
-                            # Points to the background process span.
+                            # Create the `FOLLOWS_FROM` reference to the background
+                            # process span so there is a loose coupling between the two
+                            # traces and it's easy to jump between.
                             contexts=[root_tracing_scope.span.context],
+                            tracer=test_only_tracer,
                         ):
                             pass
 
@@ -339,6 +353,7 @@ def run_as_background_process(
                             # span so there is a loose coupling between the two
                             # traces and it's easy to jump between.
                             contexts=[original_active_tracing_span.context],
+                            tracer=test_only_tracer,
                         )
 
                         # For easy usage down below, we create a context manager that
@@ -357,6 +372,7 @@ def run_as_background_process(
                         tracing_scope = start_active_span(
                             f"bgproc.{desc}",
                             tags={SynapseTags.REQUEST_ID: str(logging_context)},
+                            tracer=test_only_tracer,
                         )
                 else:
                     tracing_scope = nullcontext()
@@ -397,19 +413,19 @@ def run_as_background_process(
 P = ParamSpec("P")
 
 
-class HasServerName(Protocol):
-    server_name: str
+class HasHomeServer(Protocol):
+    hs: "HomeServer"
     """
-    The homeserver name that this cache is associated with (used to label the metric)
-    (`hs.hostname`).
+    The homeserver that this cache is associated with (used to label the metric and
+    track backgroun processes for clean shutdown).
     """
 
 
 def wrap_as_background_process(
     desc: "LiteralString",
 ) -> Callable[
-    [Callable[P, Awaitable[Optional[R]]]],
-    Callable[P, "defer.Deferred[Optional[R]]"],
+    [Callable[P, Awaitable[R | None]]],
+    Callable[P, "defer.Deferred[R | None]"],
 ]:
     """Decorator that wraps an asynchronous function `func`, returning a synchronous
     decorated function. Calling the decorated version runs `func` as a background
@@ -431,27 +447,22 @@ def wrap_as_background_process(
     """
 
     def wrapper(
-        func: Callable[Concatenate[HasServerName, P], Awaitable[Optional[R]]],
-    ) -> Callable[P, "defer.Deferred[Optional[R]]"]:
+        func: Callable[Concatenate[HasHomeServer, P], Awaitable[R | None]],
+    ) -> Callable[P, "defer.Deferred[R | None]"]:
         @wraps(func)
         def wrapped_func(
-            self: HasServerName, *args: P.args, **kwargs: P.kwargs
-        ) -> "defer.Deferred[Optional[R]]":
-            assert self.server_name is not None, (
-                "The `server_name` attribute must be set on the object where `@wrap_as_background_process` decorator is used."
+            self: HasHomeServer, *args: P.args, **kwargs: P.kwargs
+        ) -> "defer.Deferred[R | None]":
+            assert self.hs is not None, (
+                "The `hs` attribute must be set on the object where `@wrap_as_background_process` decorator is used."
             )
 
-            return run_as_background_process(
+            return self.hs.run_as_background_process(
                 desc,
-                self.server_name,
                 func,
                 self,
                 *args,
-                # type-ignore: mypy is confusing kwargs with the bg_start_span kwarg.
-                #     Argument 4 to "run_as_background_process" has incompatible type
-                #     "**P.kwargs"; expected "bool"
-                # See https://github.com/python/mypy/issues/8862
-                **kwargs,  # type: ignore[arg-type]
+                **kwargs,
             )
 
         # There are some shenanigans here, because we're decorating a method but
@@ -475,7 +486,7 @@ class BackgroundProcessLoggingContext(LoggingContext):
         *,
         name: str,
         server_name: str,
-        instance_id: Optional[Union[int, str]] = None,
+        instance_id: int | str | None = None,
     ):
         """
 
@@ -491,11 +502,11 @@ class BackgroundProcessLoggingContext(LoggingContext):
         if instance_id is None:
             instance_id = id(self)
         super().__init__(name="%s-%s" % (name, instance_id), server_name=server_name)
-        self._proc: Optional[_BackgroundProcess] = _BackgroundProcess(
+        self._proc: _BackgroundProcess | None = _BackgroundProcess(
             desc=name, server_name=server_name, ctx=self
         )
 
-    def start(self, rusage: "Optional[resource.struct_rusage]") -> None:
+    def start(self, rusage: "resource.struct_rusage | None") -> None:
         """Log context has started running (again)."""
 
         super().start(rusage)
@@ -516,9 +527,9 @@ class BackgroundProcessLoggingContext(LoggingContext):
 
     def __exit__(
         self,
-        type: Optional[Type[BaseException]],
-        value: Optional[BaseException],
-        traceback: Optional[TracebackType],
+        type: type[BaseException] | None,
+        value: BaseException | None,
+        traceback: TracebackType | None,
     ) -> None:
         """Log context has finished."""
 
diff --git a/synapse/metrics/common_usage_metrics.py b/synapse/metrics/common_usage_metrics.py
index cd1c3c8649..3f38412fa7 100644
--- a/synapse/metrics/common_usage_metrics.py
+++ b/synapse/metrics/common_usage_metrics.py
@@ -23,7 +23,6 @@ from typing import TYPE_CHECKING
 import attr
 
 from synapse.metrics import SERVER_NAME_LABEL
-from synapse.metrics.background_process_metrics import run_as_background_process
 
 if TYPE_CHECKING:
     from synapse.server import HomeServer
@@ -52,6 +51,7 @@ class CommonUsageMetricsManager:
         self.server_name = hs.hostname
         self._store = hs.get_datastores().main
         self._clock = hs.get_clock()
+        self._hs = hs
 
     async def get_metrics(self) -> CommonUsageMetrics:
         """Get the CommonUsageMetrics object. If no collection has happened yet, do it
@@ -62,18 +62,16 @@ class CommonUsageMetricsManager:
         """
         return await self._collect()
 
-    async def setup(self) -> None:
+    def setup(self) -> None:
         """Keep the gauges for common usage metrics up to date."""
-        run_as_background_process(
+        self._hs.run_as_background_process(
             desc="common_usage_metrics_update_gauges",
-            server_name=self.server_name,
             func=self._update_gauges,
         )
         self._clock.looping_call(
-            run_as_background_process,
+            self._hs.run_as_background_process,
             5 * 60 * 1000,
             desc="common_usage_metrics_update_gauges",
-            server_name=self.server_name,
             func=self._update_gauges,
         )
 
diff --git a/synapse/metrics/jemalloc.py b/synapse/metrics/jemalloc.py
index fb8adbe060..03cecec3ca 100644
--- a/synapse/metrics/jemalloc.py
+++ b/synapse/metrics/jemalloc.py
@@ -23,7 +23,7 @@ import ctypes
 import logging
 import os
 import re
-from typing import Iterable, Literal, Optional, overload
+from typing import Iterable, Literal, overload
 
 import attr
 from prometheus_client import REGISTRY, Metric
@@ -40,17 +40,17 @@ class JemallocStats:
 
     @overload
     def _mallctl(
-        self, name: str, read: Literal[True] = True, write: Optional[int] = None
+        self, name: str, read: Literal[True] = True, write: int | None = None
     ) -> int: ...
 
     @overload
     def _mallctl(
-        self, name: str, read: Literal[False], write: Optional[int] = None
+        self, name: str, read: Literal[False], write: int | None = None
     ) -> None: ...
 
     def _mallctl(
-        self, name: str, read: bool = True, write: Optional[int] = None
-    ) -> Optional[int]:
+        self, name: str, read: bool = True, write: int | None = None
+    ) -> int | None:
         """Wrapper around `mallctl` for reading and writing integers to
         jemalloc.
 
@@ -131,10 +131,10 @@ class JemallocStats:
         return self._mallctl(f"stats.{name}")
 
 
-_JEMALLOC_STATS: Optional[JemallocStats] = None
+_JEMALLOC_STATS: JemallocStats | None = None
 
 
-def get_jemalloc_stats() -> Optional[JemallocStats]:
+def get_jemalloc_stats() -> JemallocStats | None:
     """Returns an interface to jemalloc, if it is being used.
 
     Note that this will always return None until `setup_jemalloc_stats` has been
diff --git a/synapse/module_api/__init__.py b/synapse/module_api/__init__.py
index 7a419145e0..6a2d152e3f 100644
--- a/synapse/module_api/__init__.py
+++ b/synapse/module_api/__init__.py
@@ -26,15 +26,10 @@ from typing import (
     Awaitable,
     Callable,
     Collection,
-    Dict,
     Generator,
     Iterable,
-    List,
     Mapping,
-    Optional,
-    Tuple,
     TypeVar,
-    Union,
 )
 
 import attr
@@ -43,6 +38,7 @@ from typing_extensions import Concatenate, ParamSpec
 
 from twisted.internet import defer
 from twisted.internet.interfaces import IDelayedCall
+from twisted.python.threadpool import ThreadPool
 from twisted.web.resource import Resource
 
 from synapse.api import errors
@@ -79,6 +75,7 @@ from synapse.http.servlet import parse_json_object_from_request
 from synapse.http.site import SynapseRequest
 from synapse.logging.context import (
     defer_to_thread,
+    defer_to_threadpool,
     make_deferred_yieldable,
     run_in_background,
 )
@@ -228,11 +225,11 @@ class UserIpAndAgent:
 
 def run_as_background_process(
     desc: "LiteralString",
-    func: Callable[..., Awaitable[Optional[T]]],
+    func: Callable[..., Awaitable[T | None]],
     *args: Any,
     bg_start_span: bool = True,
     **kwargs: Any,
-) -> "defer.Deferred[Optional[T]]":
+) -> "defer.Deferred[T | None]":
     """
     XXX: Deprecated: use `ModuleApi.run_as_background_process` instead.
 
@@ -275,7 +272,15 @@ def run_as_background_process(
     # function instead.
     stub_server_name = "synapse_module_running_from_unknown_server"
 
-    return _run_as_background_process(
+    # Ignore the linter error here. Since this is leveraging the
+    # `run_as_background_process` function directly and we don't want to break the
+    # module api, we need to keep the function signature the same. This means we don't
+    # have access to the running `HomeServer` and cannot track this background process
+    # for cleanup during shutdown.
+    # This is not an issue during runtime and is only potentially problematic if the
+    # application cares about being able to garbage collect `HomeServer` instances
+    # during runtime.
+    return _run_as_background_process(  # type: ignore[untracked-background-process]
         desc,
         stub_server_name,
         func,
@@ -288,8 +293,8 @@ def run_as_background_process(
 def cached(
     *,
     max_entries: int = 1000,
-    num_args: Optional[int] = None,
-    uncached_args: Optional[Collection[str]] = None,
+    num_args: int | None = None,
+    uncached_args: Collection[str] | None = None,
 ) -> Callable[[F], CachedFunction[F]]:
     """Returns a decorator that applies a memoizing cache around the function. This
     decorator behaves similarly to functools.lru_cache.
@@ -331,7 +336,7 @@ class ModuleApi:
 
         # TODO: Fix this type hint once the types for the data stores have been ironed
         #       out.
-        self._store: Union[DataStore, "GenericWorkerStore"] = hs.get_datastores().main
+        self._store: DataStore | "GenericWorkerStore" = hs.get_datastores().main
         self._storage_controllers = hs.get_storage_controllers()
         self._auth = hs.get_auth()
         self._auth_handler = auth_handler
@@ -380,26 +385,20 @@ class ModuleApi:
     def register_spam_checker_callbacks(
         self,
         *,
-        check_event_for_spam: Optional[CHECK_EVENT_FOR_SPAM_CALLBACK] = None,
-        should_drop_federated_event: Optional[
-            SHOULD_DROP_FEDERATED_EVENT_CALLBACK
-        ] = None,
-        user_may_join_room: Optional[USER_MAY_JOIN_ROOM_CALLBACK] = None,
-        user_may_invite: Optional[USER_MAY_INVITE_CALLBACK] = None,
-        federated_user_may_invite: Optional[FEDERATED_USER_MAY_INVITE_CALLBACK] = None,
-        user_may_send_3pid_invite: Optional[USER_MAY_SEND_3PID_INVITE_CALLBACK] = None,
-        user_may_create_room: Optional[USER_MAY_CREATE_ROOM_CALLBACK] = None,
-        user_may_create_room_alias: Optional[
-            USER_MAY_CREATE_ROOM_ALIAS_CALLBACK
-        ] = None,
-        user_may_publish_room: Optional[USER_MAY_PUBLISH_ROOM_CALLBACK] = None,
-        user_may_send_state_event: Optional[USER_MAY_SEND_STATE_EVENT_CALLBACK] = None,
-        check_username_for_spam: Optional[CHECK_USERNAME_FOR_SPAM_CALLBACK] = None,
-        check_registration_for_spam: Optional[
-            CHECK_REGISTRATION_FOR_SPAM_CALLBACK
-        ] = None,
-        check_media_file_for_spam: Optional[CHECK_MEDIA_FILE_FOR_SPAM_CALLBACK] = None,
-        check_login_for_spam: Optional[CHECK_LOGIN_FOR_SPAM_CALLBACK] = None,
+        check_event_for_spam: CHECK_EVENT_FOR_SPAM_CALLBACK | None = None,
+        should_drop_federated_event: SHOULD_DROP_FEDERATED_EVENT_CALLBACK | None = None,
+        user_may_join_room: USER_MAY_JOIN_ROOM_CALLBACK | None = None,
+        user_may_invite: USER_MAY_INVITE_CALLBACK | None = None,
+        federated_user_may_invite: FEDERATED_USER_MAY_INVITE_CALLBACK | None = None,
+        user_may_send_3pid_invite: USER_MAY_SEND_3PID_INVITE_CALLBACK | None = None,
+        user_may_create_room: USER_MAY_CREATE_ROOM_CALLBACK | None = None,
+        user_may_create_room_alias: USER_MAY_CREATE_ROOM_ALIAS_CALLBACK | None = None,
+        user_may_publish_room: USER_MAY_PUBLISH_ROOM_CALLBACK | None = None,
+        user_may_send_state_event: USER_MAY_SEND_STATE_EVENT_CALLBACK | None = None,
+        check_username_for_spam: CHECK_USERNAME_FOR_SPAM_CALLBACK | None = None,
+        check_registration_for_spam: CHECK_REGISTRATION_FOR_SPAM_CALLBACK | None = None,
+        check_media_file_for_spam: CHECK_MEDIA_FILE_FOR_SPAM_CALLBACK | None = None,
+        check_login_for_spam: CHECK_LOGIN_FOR_SPAM_CALLBACK | None = None,
     ) -> None:
         """Registers callbacks for spam checking capabilities.
 
@@ -425,12 +424,12 @@ class ModuleApi:
     def register_account_validity_callbacks(
         self,
         *,
-        is_user_expired: Optional[IS_USER_EXPIRED_CALLBACK] = None,
-        on_user_registration: Optional[ON_USER_REGISTRATION_CALLBACK] = None,
-        on_user_login: Optional[ON_USER_LOGIN_CALLBACK] = None,
-        on_legacy_send_mail: Optional[ON_LEGACY_SEND_MAIL_CALLBACK] = None,
-        on_legacy_renew: Optional[ON_LEGACY_RENEW_CALLBACK] = None,
-        on_legacy_admin_request: Optional[ON_LEGACY_ADMIN_REQUEST] = None,
+        is_user_expired: IS_USER_EXPIRED_CALLBACK | None = None,
+        on_user_registration: ON_USER_REGISTRATION_CALLBACK | None = None,
+        on_user_login: ON_USER_LOGIN_CALLBACK | None = None,
+        on_legacy_send_mail: ON_LEGACY_SEND_MAIL_CALLBACK | None = None,
+        on_legacy_renew: ON_LEGACY_RENEW_CALLBACK | None = None,
+        on_legacy_admin_request: ON_LEGACY_ADMIN_REQUEST | None = None,
     ) -> None:
         """Registers callbacks for account validity capabilities.
 
@@ -448,9 +447,8 @@ class ModuleApi:
     def register_ratelimit_callbacks(
         self,
         *,
-        get_ratelimit_override_for_user: Optional[
-            GET_RATELIMIT_OVERRIDE_FOR_USER_CALLBACK
-        ] = None,
+        get_ratelimit_override_for_user: GET_RATELIMIT_OVERRIDE_FOR_USER_CALLBACK
+        | None = None,
     ) -> None:
         """Registers callbacks for ratelimit capabilities.
         Added in Synapse v1.132.0.
@@ -462,16 +460,13 @@ class ModuleApi:
     def register_media_repository_callbacks(
         self,
         *,
-        get_media_config_for_user: Optional[GET_MEDIA_CONFIG_FOR_USER_CALLBACK] = None,
-        is_user_allowed_to_upload_media_of_size: Optional[
-            IS_USER_ALLOWED_TO_UPLOAD_MEDIA_OF_SIZE_CALLBACK
-        ] = None,
-        get_media_upload_limits_for_user: Optional[
-            GET_MEDIA_UPLOAD_LIMITS_FOR_USER_CALLBACK
-        ] = None,
-        on_media_upload_limit_exceeded: Optional[
-            ON_MEDIA_UPLOAD_LIMIT_EXCEEDED_CALLBACK
-        ] = None,
+        get_media_config_for_user: GET_MEDIA_CONFIG_FOR_USER_CALLBACK | None = None,
+        is_user_allowed_to_upload_media_of_size: IS_USER_ALLOWED_TO_UPLOAD_MEDIA_OF_SIZE_CALLBACK
+        | None = None,
+        get_media_upload_limits_for_user: GET_MEDIA_UPLOAD_LIMITS_FOR_USER_CALLBACK
+        | None = None,
+        on_media_upload_limit_exceeded: ON_MEDIA_UPLOAD_LIMIT_EXCEEDED_CALLBACK
+        | None = None,
     ) -> None:
         """Registers callbacks for media repository capabilities.
         Added in Synapse v1.132.0.
@@ -486,28 +481,23 @@ class ModuleApi:
     def register_third_party_rules_callbacks(
         self,
         *,
-        check_event_allowed: Optional[CHECK_EVENT_ALLOWED_CALLBACK] = None,
-        on_create_room: Optional[ON_CREATE_ROOM_CALLBACK] = None,
-        check_threepid_can_be_invited: Optional[
-            CHECK_THREEPID_CAN_BE_INVITED_CALLBACK
-        ] = None,
-        check_visibility_can_be_modified: Optional[
-            CHECK_VISIBILITY_CAN_BE_MODIFIED_CALLBACK
-        ] = None,
-        on_new_event: Optional[ON_NEW_EVENT_CALLBACK] = None,
-        check_can_shutdown_room: Optional[CHECK_CAN_SHUTDOWN_ROOM_CALLBACK] = None,
-        check_can_deactivate_user: Optional[CHECK_CAN_DEACTIVATE_USER_CALLBACK] = None,
-        on_profile_update: Optional[ON_PROFILE_UPDATE_CALLBACK] = None,
-        on_user_deactivation_status_changed: Optional[
-            ON_USER_DEACTIVATION_STATUS_CHANGED_CALLBACK
-        ] = None,
-        on_threepid_bind: Optional[ON_THREEPID_BIND_CALLBACK] = None,
-        on_add_user_third_party_identifier: Optional[
-            ON_ADD_USER_THIRD_PARTY_IDENTIFIER_CALLBACK
-        ] = None,
-        on_remove_user_third_party_identifier: Optional[
-            ON_REMOVE_USER_THIRD_PARTY_IDENTIFIER_CALLBACK
-        ] = None,
+        check_event_allowed: CHECK_EVENT_ALLOWED_CALLBACK | None = None,
+        on_create_room: ON_CREATE_ROOM_CALLBACK | None = None,
+        check_threepid_can_be_invited: CHECK_THREEPID_CAN_BE_INVITED_CALLBACK
+        | None = None,
+        check_visibility_can_be_modified: CHECK_VISIBILITY_CAN_BE_MODIFIED_CALLBACK
+        | None = None,
+        on_new_event: ON_NEW_EVENT_CALLBACK | None = None,
+        check_can_shutdown_room: CHECK_CAN_SHUTDOWN_ROOM_CALLBACK | None = None,
+        check_can_deactivate_user: CHECK_CAN_DEACTIVATE_USER_CALLBACK | None = None,
+        on_profile_update: ON_PROFILE_UPDATE_CALLBACK | None = None,
+        on_user_deactivation_status_changed: ON_USER_DEACTIVATION_STATUS_CHANGED_CALLBACK
+        | None = None,
+        on_threepid_bind: ON_THREEPID_BIND_CALLBACK | None = None,
+        on_add_user_third_party_identifier: ON_ADD_USER_THIRD_PARTY_IDENTIFIER_CALLBACK
+        | None = None,
+        on_remove_user_third_party_identifier: ON_REMOVE_USER_THIRD_PARTY_IDENTIFIER_CALLBACK
+        | None = None,
     ) -> None:
         """Registers callbacks for third party event rules capabilities.
 
@@ -531,8 +521,8 @@ class ModuleApi:
     def register_presence_router_callbacks(
         self,
         *,
-        get_users_for_states: Optional[GET_USERS_FOR_STATES_CALLBACK] = None,
-        get_interested_users: Optional[GET_INTERESTED_USERS_CALLBACK] = None,
+        get_users_for_states: GET_USERS_FOR_STATES_CALLBACK | None = None,
+        get_interested_users: GET_INTERESTED_USERS_CALLBACK | None = None,
     ) -> None:
         """Registers callbacks for presence router capabilities.
 
@@ -546,18 +536,15 @@ class ModuleApi:
     def register_password_auth_provider_callbacks(
         self,
         *,
-        check_3pid_auth: Optional[CHECK_3PID_AUTH_CALLBACK] = None,
-        on_logged_out: Optional[ON_LOGGED_OUT_CALLBACK] = None,
-        auth_checkers: Optional[
-            Dict[Tuple[str, Tuple[str, ...]], CHECK_AUTH_CALLBACK]
-        ] = None,
-        is_3pid_allowed: Optional[IS_3PID_ALLOWED_CALLBACK] = None,
-        get_username_for_registration: Optional[
-            GET_USERNAME_FOR_REGISTRATION_CALLBACK
-        ] = None,
-        get_displayname_for_registration: Optional[
-            GET_DISPLAYNAME_FOR_REGISTRATION_CALLBACK
-        ] = None,
+        check_3pid_auth: CHECK_3PID_AUTH_CALLBACK | None = None,
+        on_logged_out: ON_LOGGED_OUT_CALLBACK | None = None,
+        auth_checkers: dict[tuple[str, tuple[str, ...]], CHECK_AUTH_CALLBACK]
+        | None = None,
+        is_3pid_allowed: IS_3PID_ALLOWED_CALLBACK | None = None,
+        get_username_for_registration: GET_USERNAME_FOR_REGISTRATION_CALLBACK
+        | None = None,
+        get_displayname_for_registration: GET_DISPLAYNAME_FOR_REGISTRATION_CALLBACK
+        | None = None,
     ) -> None:
         """Registers callbacks for password auth provider capabilities.
 
@@ -581,8 +568,8 @@ class ModuleApi:
         self,
         *,
         on_update: ON_UPDATE_CALLBACK,
-        default_batch_size: Optional[DEFAULT_BATCH_SIZE_CALLBACK] = None,
-        min_batch_size: Optional[MIN_BATCH_SIZE_CALLBACK] = None,
+        default_batch_size: DEFAULT_BATCH_SIZE_CALLBACK | None = None,
+        min_batch_size: MIN_BATCH_SIZE_CALLBACK | None = None,
     ) -> None:
         """Registers background update controller callbacks.
 
@@ -599,7 +586,7 @@ class ModuleApi:
     def register_account_data_callbacks(
         self,
         *,
-        on_account_data_updated: Optional[ON_ACCOUNT_DATA_UPDATED_CALLBACK] = None,
+        on_account_data_updated: ON_ACCOUNT_DATA_UPDATED_CALLBACK | None = None,
     ) -> None:
         """Registers account data callbacks.
 
@@ -628,9 +615,8 @@ class ModuleApi:
     def register_add_extra_fields_to_unsigned_client_event_callbacks(
         self,
         *,
-        add_field_to_unsigned_callback: Optional[
-            ADD_EXTRA_FIELDS_TO_UNSIGNED_CLIENT_EVENT_CALLBACK
-        ] = None,
+        add_field_to_unsigned_callback: ADD_EXTRA_FIELDS_TO_UNSIGNED_CLIENT_EVENT_CALLBACK
+        | None = None,
     ) -> None:
         """Registers a callback that can be used to add fields to the unsigned
         section of events.
@@ -701,7 +687,7 @@ class ModuleApi:
         return self._server_name
 
     @property
-    def worker_name(self) -> Optional[str]:
+    def worker_name(self) -> str | None:
         """The name of the worker this specific instance is running as per the
         "worker_name" configuration setting, or None if it's the main process.
 
@@ -710,7 +696,7 @@ class ModuleApi:
         return self._hs.config.worker.worker_name
 
     @property
-    def worker_app(self) -> Optional[str]:
+    def worker_app(self) -> str | None:
         """The name of the worker app this specific instance is running as per the
         "worker_app" configuration setting, or None if it's the main process.
 
@@ -718,7 +704,7 @@ class ModuleApi:
         """
         return self._hs.config.worker.worker_app
 
-    async def get_userinfo_by_id(self, user_id: str) -> Optional[UserInfo]:
+    async def get_userinfo_by_id(self, user_id: str) -> UserInfo | None:
         """Get user info by user_id
 
         Added in Synapse v1.41.0.
@@ -819,7 +805,7 @@ class ModuleApi:
         user_id = UserID.from_string(f"@{localpart}:{server_name}")
         return await self._store.get_profileinfo(user_id)
 
-    async def get_threepids_for_user(self, user_id: str) -> List[Dict[str, str]]:
+    async def get_threepids_for_user(self, user_id: str) -> list[dict[str, str]]:
         """Look up the threepids (email addresses and phone numbers) associated with the
         given Matrix user ID.
 
@@ -836,7 +822,7 @@ class ModuleApi:
         """
         return [attr.asdict(t) for t in await self._store.user_get_threepids(user_id)]
 
-    def check_user_exists(self, user_id: str) -> "defer.Deferred[Optional[str]]":
+    def check_user_exists(self, user_id: str) -> "defer.Deferred[str | None]":
         """Check if user exists.
 
         Added in Synapse v0.25.0.
@@ -854,9 +840,9 @@ class ModuleApi:
     def register(
         self,
         localpart: str,
-        displayname: Optional[str] = None,
-        emails: Optional[List[str]] = None,
-    ) -> Generator["defer.Deferred[Any]", Any, Tuple[str, str]]:
+        displayname: str | None = None,
+        emails: list[str] | None = None,
+    ) -> Generator["defer.Deferred[Any]", Any, tuple[str, str]]:
         """Registers a new user with given localpart and optional displayname, emails.
 
         Also returns an access token for the new user.
@@ -885,8 +871,8 @@ class ModuleApi:
     def register_user(
         self,
         localpart: str,
-        displayname: Optional[str] = None,
-        emails: Optional[List[str]] = None,
+        displayname: str | None = None,
+        emails: list[str] | None = None,
         admin: bool = False,
     ) -> "defer.Deferred[str]":
         """Registers a new user with given localpart and optional displayname, emails.
@@ -919,9 +905,9 @@ class ModuleApi:
     def register_device(
         self,
         user_id: str,
-        device_id: Optional[str] = None,
-        initial_display_name: Optional[str] = None,
-    ) -> "defer.Deferred[Tuple[str, str, Optional[int], Optional[str]]]":
+        device_id: str | None = None,
+        initial_display_name: str | None = None,
+    ) -> "defer.Deferred[tuple[str, str, int | None, str | None]]":
         """Register a device for a user and generate an access token.
 
         Added in Synapse v1.2.0.
@@ -971,8 +957,8 @@ class ModuleApi:
         self,
         user_id: str,
         duration_in_ms: int = (2 * 60 * 1000),
-        auth_provider_id: Optional[str] = None,
-        auth_provider_session_id: Optional[str] = None,
+        auth_provider_id: str | None = None,
+        auth_provider_session_id: str | None = None,
     ) -> str:
         """Create a login token suitable for m.login.token authentication
 
@@ -1075,7 +1061,7 @@ class ModuleApi:
         )
 
     async def invalidate_cache(
-        self, cached_func: CachedFunction, keys: Tuple[Any, ...]
+        self, cached_func: CachedFunction, keys: tuple[Any, ...]
     ) -> None:
         """Invalidate a cache entry of a cached function across workers. The cached function
         needs to be registered on all workers first with `register_cached_function`.
@@ -1128,7 +1114,7 @@ class ModuleApi:
 
     @defer.inlineCallbacks
     def get_state_events_in_room(
-        self, room_id: str, types: Iterable[Tuple[str, Optional[str]]]
+        self, room_id: str, types: Iterable[tuple[str, str | None]]
     ) -> Generator[defer.Deferred, Any, Iterable[EventBase]]:
         """Gets current state events for the given room.
 
@@ -1159,8 +1145,8 @@ class ModuleApi:
         target: str,
         room_id: str,
         new_membership: str,
-        content: Optional[JsonDict] = None,
-        remote_room_hosts: Optional[List[str]] = None,
+        content: JsonDict | None = None,
+        remote_room_hosts: list[str] | None = None,
     ) -> EventBase:
         """Updates the membership of a user to the given value.
 
@@ -1336,7 +1322,7 @@ class ModuleApi:
             )
 
     async def set_presence_for_users(
-        self, users: Mapping[str, Tuple[str, Optional[str]]]
+        self, users: Mapping[str, tuple[str, str | None]]
     ) -> None:
         """
         Update the internal presence state of users.
@@ -1371,7 +1357,7 @@ class ModuleApi:
         f: Callable,
         msec: float,
         *args: object,
-        desc: Optional[str] = None,
+        desc: str | None = None,
         run_on_all_instances: bool = False,
         **kwargs: object,
     ) -> None:
@@ -1402,7 +1388,7 @@ class ModuleApi:
 
         if self._hs.config.worker.run_background_tasks or run_on_all_instances:
             self._clock.looping_call(
-                self.run_as_background_process,
+                self._hs.run_as_background_process,
                 msec,
                 desc,
                 lambda: maybe_awaitable(f(*args, **kwargs)),
@@ -1430,7 +1416,7 @@ class ModuleApi:
         msec: float,
         f: Callable,
         *args: object,
-        desc: Optional[str] = None,
+        desc: str | None = None,
         **kwargs: object,
     ) -> IDelayedCall:
         """Wraps a function as a background process and calls it in a given number of milliseconds.
@@ -1460,7 +1446,7 @@ class ModuleApi:
         return self._clock.call_later(
             # convert ms to seconds as needed by call_later.
             msec * 0.001,
-            self.run_as_background_process,
+            self._hs.run_as_background_process,
             desc,
             lambda: maybe_awaitable(f(*args, **kwargs)),
         )
@@ -1476,11 +1462,11 @@ class ModuleApi:
     async def send_http_push_notification(
         self,
         user_id: str,
-        device_id: Optional[str],
+        device_id: str | None,
         content: JsonDict,
-        tweaks: Optional[JsonMapping] = None,
-        default_payload: Optional[JsonMapping] = None,
-    ) -> Dict[str, bool]:
+        tweaks: JsonMapping | None = None,
+        default_payload: JsonMapping | None = None,
+    ) -> dict[str, bool]:
         """Send an HTTP push notification that is forwarded to the registered push gateway
         for the specified user/device.
 
@@ -1544,9 +1530,9 @@ class ModuleApi:
 
     def read_templates(
         self,
-        filenames: List[str],
-        custom_template_directory: Optional[str] = None,
-    ) -> List[jinja2.Template]:
+        filenames: list[str],
+        custom_template_directory: str | None = None,
+    ) -> list[jinja2.Template]:
         """Read and load the content of the template files at the given location.
         By default, Synapse will look for these templates in its configured template
         directory, but another directory to search in can be provided.
@@ -1566,7 +1552,7 @@ class ModuleApi:
             (td for td in (self.custom_template_dir, custom_template_directory) if td),
         )
 
-    def is_mine(self, id: Union[str, DomainSpecificString]) -> bool:
+    def is_mine(self, id: str | DomainSpecificString) -> bool:
         """
         Checks whether an ID (user id, room, ...) comes from this homeserver.
 
@@ -1585,7 +1571,7 @@ class ModuleApi:
 
     async def get_user_ip_and_agents(
         self, user_id: str, since_ts: int = 0
-    ) -> List[UserIpAndAgent]:
+    ) -> list[UserIpAndAgent]:
         """
         Return the list of user IPs and agents for a user.
 
@@ -1628,7 +1614,7 @@ class ModuleApi:
     async def get_room_state(
         self,
         room_id: str,
-        event_filter: Optional[Iterable[Tuple[str, Optional[str]]]] = None,
+        event_filter: Iterable[tuple[str, str | None]] | None = None,
     ) -> StateMap[EventBase]:
         """Returns the current state of the given room.
 
@@ -1670,11 +1656,11 @@ class ModuleApi:
     def run_as_background_process(
         self,
         desc: "LiteralString",
-        func: Callable[..., Awaitable[Optional[T]]],
+        func: Callable[..., Awaitable[T | None]],
         *args: Any,
         bg_start_span: bool = True,
         **kwargs: Any,
-    ) -> "defer.Deferred[Optional[T]]":
+    ) -> "defer.Deferred[T | None]":
         """Run the given function in its own logcontext, with resource metrics
 
         This should be used to wrap processes which are fired off to run in the
@@ -1701,8 +1687,8 @@ class ModuleApi:
             Note that the returned Deferred does not follow the synapse logcontext
             rules.
         """
-        return _run_as_background_process(
-            desc, self.server_name, func, *args, bg_start_span=bg_start_span, **kwargs
+        return self._hs.run_as_background_process(
+            desc, func, *args, bg_start_span=bg_start_span, **kwargs
         )
 
     async def defer_to_thread(
@@ -1725,6 +1711,33 @@ class ModuleApi:
         """
         return await defer_to_thread(self._hs.get_reactor(), f, *args, **kwargs)
 
+    async def defer_to_threadpool(
+        self,
+        threadpool: ThreadPool,
+        f: Callable[P, T],
+        *args: P.args,
+        **kwargs: P.kwargs,
+    ) -> T:
+        """Runs the given function in a separate thread from the given thread pool.
+
+        Allows specifying a custom thread pool instead of using the default Synapse
+        one. To use the default Synapse threadpool, use `defer_to_thread` instead.
+
+        Added in Synapse v1.140.0.
+
+        Args:
+            threadpool: The thread pool to use.
+            f: The function to run.
+            args: The function's arguments.
+            kwargs: The function's keyword arguments.
+
+        Returns:
+            The return value of the function once ran in a thread.
+        """
+        return await defer_to_threadpool(
+            self._hs.get_reactor(), threadpool, f, *args, **kwargs
+        )
+
     async def check_username(self, username: str) -> None:
         """Checks if the provided username uses the grammar defined in the Matrix
         specification, and is already being used by an existing user.
@@ -1765,9 +1778,7 @@ class ModuleApi:
         """
         await self._store.add_user_bound_threepid(user_id, medium, address, id_server)
 
-    def check_push_rule_actions(
-        self, actions: List[Union[str, Dict[str, str]]]
-    ) -> None:
+    def check_push_rule_actions(self, actions: list[str | dict[str, str]]) -> None:
         """Checks if the given push rule actions are valid according to the Matrix
         specification.
 
@@ -1790,7 +1801,7 @@ class ModuleApi:
         scope: str,
         kind: str,
         rule_id: str,
-        actions: List[Union[str, Dict[str, str]]],
+        actions: list[str | dict[str, str]],
     ) -> None:
         """Changes the actions of an existing push rule for the given user.
 
@@ -1828,8 +1839,8 @@ class ModuleApi:
         )
 
     async def get_monthly_active_users_by_service(
-        self, start_timestamp: Optional[int] = None, end_timestamp: Optional[int] = None
-    ) -> List[Tuple[str, str]]:
+        self, start_timestamp: int | None = None, end_timestamp: int | None = None
+    ) -> list[tuple[str, str]]:
         """Generates list of monthly active users and their services.
         Please see corresponding storage docstring for more details.
 
@@ -1849,7 +1860,7 @@ class ModuleApi:
             start_timestamp, end_timestamp
         )
 
-    async def get_canonical_room_alias(self, room_id: RoomID) -> Optional[RoomAlias]:
+    async def get_canonical_room_alias(self, room_id: RoomID) -> RoomAlias | None:
         """
         Retrieve the given room's current canonical alias.
 
@@ -1875,7 +1886,7 @@ class ModuleApi:
             return RoomAlias.from_string(room_alias_str)
         return None
 
-    async def lookup_room_alias(self, room_alias: str) -> Tuple[str, List[str]]:
+    async def lookup_room_alias(self, room_alias: str) -> tuple[str, list[str]]:
         """
         Get the room ID associated with a room alias.
 
@@ -1904,8 +1915,8 @@ class ModuleApi:
         user_id: str,
         config: JsonDict,
         ratelimit: bool = True,
-        creator_join_profile: Optional[JsonDict] = None,
-    ) -> Tuple[str, Optional[str]]:
+        creator_join_profile: JsonDict | None = None,
+    ) -> tuple[str, str | None]:
         """Creates a new room.
 
         Added in Synapse v1.65.0.
@@ -2075,7 +2086,7 @@ class AccountDataManager:
                 f"{user_id} is not local to this homeserver; can't access account data for remote users."
             )
 
-    async def get_global(self, user_id: str, data_type: str) -> Optional[JsonMapping]:
+    async def get_global(self, user_id: str, data_type: str) -> JsonMapping | None:
         """
         Gets some global account data, of a specified type, for the specified user.
 
diff --git a/synapse/module_api/callbacks/account_validity_callbacks.py b/synapse/module_api/callbacks/account_validity_callbacks.py
index a989249280..892e9c8ecb 100644
--- a/synapse/module_api/callbacks/account_validity_callbacks.py
+++ b/synapse/module_api/callbacks/account_validity_callbacks.py
@@ -20,43 +20,43 @@
 #
 
 import logging
-from typing import Awaitable, Callable, List, Optional, Tuple
+from typing import Awaitable, Callable
 
 from twisted.web.http import Request
 
 logger = logging.getLogger(__name__)
 
 # Types for callbacks to be registered via the module api
-IS_USER_EXPIRED_CALLBACK = Callable[[str], Awaitable[Optional[bool]]]
+IS_USER_EXPIRED_CALLBACK = Callable[[str], Awaitable[bool | None]]
 ON_USER_REGISTRATION_CALLBACK = Callable[[str], Awaitable]
-ON_USER_LOGIN_CALLBACK = Callable[[str, Optional[str], Optional[str]], Awaitable]
+ON_USER_LOGIN_CALLBACK = Callable[[str, str | None, str | None], Awaitable]
 # Temporary hooks to allow for a transition from `/_matrix/client` endpoints
 # to `/_synapse/client/account_validity`. See `register_callbacks` below.
 ON_LEGACY_SEND_MAIL_CALLBACK = Callable[[str], Awaitable]
-ON_LEGACY_RENEW_CALLBACK = Callable[[str], Awaitable[Tuple[bool, bool, int]]]
+ON_LEGACY_RENEW_CALLBACK = Callable[[str], Awaitable[tuple[bool, bool, int]]]
 ON_LEGACY_ADMIN_REQUEST = Callable[[Request], Awaitable]
 
 
 class AccountValidityModuleApiCallbacks:
     def __init__(self) -> None:
-        self.is_user_expired_callbacks: List[IS_USER_EXPIRED_CALLBACK] = []
-        self.on_user_registration_callbacks: List[ON_USER_REGISTRATION_CALLBACK] = []
-        self.on_user_login_callbacks: List[ON_USER_LOGIN_CALLBACK] = []
-        self.on_legacy_send_mail_callback: Optional[ON_LEGACY_SEND_MAIL_CALLBACK] = None
-        self.on_legacy_renew_callback: Optional[ON_LEGACY_RENEW_CALLBACK] = None
+        self.is_user_expired_callbacks: list[IS_USER_EXPIRED_CALLBACK] = []
+        self.on_user_registration_callbacks: list[ON_USER_REGISTRATION_CALLBACK] = []
+        self.on_user_login_callbacks: list[ON_USER_LOGIN_CALLBACK] = []
+        self.on_legacy_send_mail_callback: ON_LEGACY_SEND_MAIL_CALLBACK | None = None
+        self.on_legacy_renew_callback: ON_LEGACY_RENEW_CALLBACK | None = None
 
         # The legacy admin requests callback isn't a protected attribute because we need
         # to access it from the admin servlet, which is outside of this handler.
-        self.on_legacy_admin_request_callback: Optional[ON_LEGACY_ADMIN_REQUEST] = None
+        self.on_legacy_admin_request_callback: ON_LEGACY_ADMIN_REQUEST | None = None
 
     def register_callbacks(
         self,
-        is_user_expired: Optional[IS_USER_EXPIRED_CALLBACK] = None,
-        on_user_registration: Optional[ON_USER_REGISTRATION_CALLBACK] = None,
-        on_user_login: Optional[ON_USER_LOGIN_CALLBACK] = None,
-        on_legacy_send_mail: Optional[ON_LEGACY_SEND_MAIL_CALLBACK] = None,
-        on_legacy_renew: Optional[ON_LEGACY_RENEW_CALLBACK] = None,
-        on_legacy_admin_request: Optional[ON_LEGACY_ADMIN_REQUEST] = None,
+        is_user_expired: IS_USER_EXPIRED_CALLBACK | None = None,
+        on_user_registration: ON_USER_REGISTRATION_CALLBACK | None = None,
+        on_user_login: ON_USER_LOGIN_CALLBACK | None = None,
+        on_legacy_send_mail: ON_LEGACY_SEND_MAIL_CALLBACK | None = None,
+        on_legacy_renew: ON_LEGACY_RENEW_CALLBACK | None = None,
+        on_legacy_admin_request: ON_LEGACY_ADMIN_REQUEST | None = None,
     ) -> None:
         """Register callbacks from module for each hook."""
         if is_user_expired is not None:
diff --git a/synapse/module_api/callbacks/media_repository_callbacks.py b/synapse/module_api/callbacks/media_repository_callbacks.py
index 7d3aed9d66..f1e6ea4c38 100644
--- a/synapse/module_api/callbacks/media_repository_callbacks.py
+++ b/synapse/module_api/callbacks/media_repository_callbacks.py
@@ -13,7 +13,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Awaitable, Callable, List, Optional
+from typing import TYPE_CHECKING, Awaitable, Callable
 
 from synapse.config.repository import MediaUploadLimit
 from synapse.types import JsonDict
@@ -25,12 +25,12 @@ if TYPE_CHECKING:
 
 logger = logging.getLogger(__name__)
 
-GET_MEDIA_CONFIG_FOR_USER_CALLBACK = Callable[[str], Awaitable[Optional[JsonDict]]]
+GET_MEDIA_CONFIG_FOR_USER_CALLBACK = Callable[[str], Awaitable[JsonDict | None]]
 
 IS_USER_ALLOWED_TO_UPLOAD_MEDIA_OF_SIZE_CALLBACK = Callable[[str, int], Awaitable[bool]]
 
 GET_MEDIA_UPLOAD_LIMITS_FOR_USER_CALLBACK = Callable[
-    [str], Awaitable[Optional[List[MediaUploadLimit]]]
+    [str], Awaitable[list[MediaUploadLimit] | None]
 ]
 
 ON_MEDIA_UPLOAD_LIMIT_EXCEEDED_CALLBACK = Callable[
@@ -42,31 +42,28 @@ class MediaRepositoryModuleApiCallbacks:
     def __init__(self, hs: "HomeServer") -> None:
         self.server_name = hs.hostname
         self.clock = hs.get_clock()
-        self._get_media_config_for_user_callbacks: List[
+        self._get_media_config_for_user_callbacks: list[
             GET_MEDIA_CONFIG_FOR_USER_CALLBACK
         ] = []
-        self._is_user_allowed_to_upload_media_of_size_callbacks: List[
+        self._is_user_allowed_to_upload_media_of_size_callbacks: list[
             IS_USER_ALLOWED_TO_UPLOAD_MEDIA_OF_SIZE_CALLBACK
         ] = []
-        self._get_media_upload_limits_for_user_callbacks: List[
+        self._get_media_upload_limits_for_user_callbacks: list[
             GET_MEDIA_UPLOAD_LIMITS_FOR_USER_CALLBACK
         ] = []
-        self._on_media_upload_limit_exceeded_callbacks: List[
+        self._on_media_upload_limit_exceeded_callbacks: list[
             ON_MEDIA_UPLOAD_LIMIT_EXCEEDED_CALLBACK
         ] = []
 
     def register_callbacks(
         self,
-        get_media_config_for_user: Optional[GET_MEDIA_CONFIG_FOR_USER_CALLBACK] = None,
-        is_user_allowed_to_upload_media_of_size: Optional[
-            IS_USER_ALLOWED_TO_UPLOAD_MEDIA_OF_SIZE_CALLBACK
-        ] = None,
-        get_media_upload_limits_for_user: Optional[
-            GET_MEDIA_UPLOAD_LIMITS_FOR_USER_CALLBACK
-        ] = None,
-        on_media_upload_limit_exceeded: Optional[
-            ON_MEDIA_UPLOAD_LIMIT_EXCEEDED_CALLBACK
-        ] = None,
+        get_media_config_for_user: GET_MEDIA_CONFIG_FOR_USER_CALLBACK | None = None,
+        is_user_allowed_to_upload_media_of_size: IS_USER_ALLOWED_TO_UPLOAD_MEDIA_OF_SIZE_CALLBACK
+        | None = None,
+        get_media_upload_limits_for_user: GET_MEDIA_UPLOAD_LIMITS_FOR_USER_CALLBACK
+        | None = None,
+        on_media_upload_limit_exceeded: ON_MEDIA_UPLOAD_LIMIT_EXCEEDED_CALLBACK
+        | None = None,
     ) -> None:
         """Register callbacks from module for each hook."""
         if get_media_config_for_user is not None:
@@ -87,14 +84,14 @@ class MediaRepositoryModuleApiCallbacks:
                 on_media_upload_limit_exceeded
             )
 
-    async def get_media_config_for_user(self, user_id: str) -> Optional[JsonDict]:
+    async def get_media_config_for_user(self, user_id: str) -> JsonDict | None:
         for callback in self._get_media_config_for_user_callbacks:
             with Measure(
                 self.clock,
                 name=f"{callback.__module__}.{callback.__qualname__}",
                 server_name=self.server_name,
             ):
-                res: Optional[JsonDict] = await delay_cancellation(callback(user_id))
+                res: JsonDict | None = await delay_cancellation(callback(user_id))
             if res:
                 return res
 
@@ -117,7 +114,7 @@ class MediaRepositoryModuleApiCallbacks:
 
     async def get_media_upload_limits_for_user(
         self, user_id: str
-    ) -> Optional[List[MediaUploadLimit]]:
+    ) -> list[MediaUploadLimit] | None:
         """
         Get the first non-None list of MediaUploadLimits for the user from the registered callbacks.
         If a list is returned it will be sorted in descending order of duration.
@@ -128,7 +125,7 @@ class MediaRepositoryModuleApiCallbacks:
                 name=f"{callback.__module__}.{callback.__qualname__}",
                 server_name=self.server_name,
             ):
-                res: Optional[List[MediaUploadLimit]] = await delay_cancellation(
+                res: list[MediaUploadLimit] | None = await delay_cancellation(
                     callback(user_id)
                 )
             if res is not None:  # to allow [] to be returned meaning no limit
diff --git a/synapse/module_api/callbacks/ratelimit_callbacks.py b/synapse/module_api/callbacks/ratelimit_callbacks.py
index a580ea7d7c..0f4080dcd6 100644
--- a/synapse/module_api/callbacks/ratelimit_callbacks.py
+++ b/synapse/module_api/callbacks/ratelimit_callbacks.py
@@ -13,7 +13,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Awaitable, Callable, List, Optional
+from typing import TYPE_CHECKING, Awaitable, Callable
 
 import attr
 
@@ -37,7 +37,7 @@ class RatelimitOverride:
 
 
 GET_RATELIMIT_OVERRIDE_FOR_USER_CALLBACK = Callable[
-    [str, str], Awaitable[Optional[RatelimitOverride]]
+    [str, str], Awaitable[RatelimitOverride | None]
 ]
 
 
@@ -45,15 +45,14 @@ class RatelimitModuleApiCallbacks:
     def __init__(self, hs: "HomeServer") -> None:
         self.server_name = hs.hostname
         self.clock = hs.get_clock()
-        self._get_ratelimit_override_for_user_callbacks: List[
+        self._get_ratelimit_override_for_user_callbacks: list[
             GET_RATELIMIT_OVERRIDE_FOR_USER_CALLBACK
         ] = []
 
     def register_callbacks(
         self,
-        get_ratelimit_override_for_user: Optional[
-            GET_RATELIMIT_OVERRIDE_FOR_USER_CALLBACK
-        ] = None,
+        get_ratelimit_override_for_user: GET_RATELIMIT_OVERRIDE_FOR_USER_CALLBACK
+        | None = None,
     ) -> None:
         """Register callbacks from module for each hook."""
         if get_ratelimit_override_for_user is not None:
@@ -63,14 +62,14 @@ class RatelimitModuleApiCallbacks:
 
     async def get_ratelimit_override_for_user(
         self, user_id: str, limiter_name: str
-    ) -> Optional[RatelimitOverride]:
+    ) -> RatelimitOverride | None:
         for callback in self._get_ratelimit_override_for_user_callbacks:
             with Measure(
                 self.clock,
                 name=f"{callback.__module__}.{callback.__qualname__}",
                 server_name=self.server_name,
             ):
-                res: Optional[RatelimitOverride] = await delay_cancellation(
+                res: RatelimitOverride | None = await delay_cancellation(
                     callback(user_id, limiter_name)
                 )
             if res:
diff --git a/synapse/module_api/callbacks/spamchecker_callbacks.py b/synapse/module_api/callbacks/spamchecker_callbacks.py
index 428e733979..8b34f7ef6c 100644
--- a/synapse/module_api/callbacks/spamchecker_callbacks.py
+++ b/synapse/module_api/callbacks/spamchecker_callbacks.py
@@ -29,11 +29,7 @@ from typing import (
     Awaitable,
     Callable,
     Collection,
-    List,
     Literal,
-    Optional,
-    Tuple,
-    Union,
     cast,
 )
 
@@ -55,210 +51,96 @@ logger = logging.getLogger(__name__)
 
 CHECK_EVENT_FOR_SPAM_CALLBACK = Callable[
     ["synapse.events.EventBase"],
-    Awaitable[
-        Union[
-            str,
-            Codes,
-            # Highly experimental, not officially part of the spamchecker API, may
-            # disappear without warning depending on the results of ongoing
-            # experiments.
-            # Use this to return additional information as part of an error.
-            Tuple[Codes, JsonDict],
-            # Deprecated
-            bool,
-        ]
-    ],
+    Awaitable[str | Codes | tuple[Codes, JsonDict] | bool],
 ]
 SHOULD_DROP_FEDERATED_EVENT_CALLBACK = Callable[
     ["synapse.events.EventBase"],
-    Awaitable[Union[bool, str]],
+    Awaitable[bool | str],
 ]
 USER_MAY_JOIN_ROOM_CALLBACK = Callable[
     [str, str, bool],
-    Awaitable[
-        Union[
-            Literal["NOT_SPAM"],
-            Codes,
-            # Highly experimental, not officially part of the spamchecker API, may
-            # disappear without warning depending on the results of ongoing
-            # experiments.
-            # Use this to return additional information as part of an error.
-            Tuple[Codes, JsonDict],
-            # Deprecated
-            bool,
-        ]
-    ],
+    Awaitable[Literal["NOT_SPAM"] | Codes | tuple[Codes, JsonDict] | bool],
 ]
 USER_MAY_INVITE_CALLBACK = Callable[
     [str, str, str],
-    Awaitable[
-        Union[
-            Literal["NOT_SPAM"],
-            Codes,
-            # Highly experimental, not officially part of the spamchecker API, may
-            # disappear without warning depending on the results of ongoing
-            # experiments.
-            # Use this to return additional information as part of an error.
-            Tuple[Codes, JsonDict],
-            # Deprecated
-            bool,
-        ]
-    ],
+    Awaitable[Literal["NOT_SPAM"] | Codes | tuple[Codes, JsonDict] | bool],
 ]
 FEDERATED_USER_MAY_INVITE_CALLBACK = Callable[
     ["synapse.events.EventBase"],
-    Awaitable[
-        Union[
-            Literal["NOT_SPAM"],
-            Codes,
-            # Highly experimental, not officially part of the spamchecker API, may
-            # disappear without warning depending on the results of ongoing
-            # experiments.
-            # Use this to return additional information as part of an error.
-            Tuple[Codes, JsonDict],
-            # Deprecated
-            bool,
-        ]
-    ],
+    Awaitable[Literal["NOT_SPAM"] | Codes | tuple[Codes, JsonDict] | bool],
 ]
 USER_MAY_SEND_3PID_INVITE_CALLBACK = Callable[
     [str, str, str, str],
-    Awaitable[
-        Union[
-            Literal["NOT_SPAM"],
-            Codes,
-            # Highly experimental, not officially part of the spamchecker API, may
-            # disappear without warning depending on the results of ongoing
-            # experiments.
-            # Use this to return additional information as part of an error.
-            Tuple[Codes, JsonDict],
-            # Deprecated
-            bool,
-        ]
-    ],
+    Awaitable[Literal["NOT_SPAM"] | Codes | tuple[Codes, JsonDict] | bool],
 ]
-USER_MAY_CREATE_ROOM_CALLBACK_RETURN_VALUE = Union[
-    Literal["NOT_SPAM"],
-    Codes,
+USER_MAY_CREATE_ROOM_CALLBACK_RETURN_VALUE = (
+    Literal["NOT_SPAM"]
+    | Codes
+    |
     # Highly experimental, not officially part of the spamchecker API, may
     # disappear without warning depending on the results of ongoing
     # experiments.
     # Use this to return additional information as part of an error.
-    Tuple[Codes, JsonDict],
+    tuple[Codes, JsonDict]
+    |
     # Deprecated
-    bool,
-]
-USER_MAY_CREATE_ROOM_CALLBACK = Union[
+    bool
+)
+USER_MAY_CREATE_ROOM_CALLBACK = (
     Callable[
         [str, JsonDict],
         Awaitable[USER_MAY_CREATE_ROOM_CALLBACK_RETURN_VALUE],
-    ],
-    Callable[  # Single argument variant for backwards compatibility
+    ]
+    | Callable[  # Single argument variant for backwards compatibility
         [str], Awaitable[USER_MAY_CREATE_ROOM_CALLBACK_RETURN_VALUE]
-    ],
-]
+    ]
+)
 USER_MAY_CREATE_ROOM_ALIAS_CALLBACK = Callable[
     [str, RoomAlias],
-    Awaitable[
-        Union[
-            Literal["NOT_SPAM"],
-            Codes,
-            # Highly experimental, not officially part of the spamchecker API, may
-            # disappear without warning depending on the results of ongoing
-            # experiments.
-            # Use this to return additional information as part of an error.
-            Tuple[Codes, JsonDict],
-            # Deprecated
-            bool,
-        ]
-    ],
+    Awaitable[Literal["NOT_SPAM"] | Codes | tuple[Codes, JsonDict] | bool],
 ]
 USER_MAY_PUBLISH_ROOM_CALLBACK = Callable[
     [str, str],
-    Awaitable[
-        Union[
-            Literal["NOT_SPAM"],
-            Codes,
-            # Highly experimental, not officially part of the spamchecker API, may
-            # disappear without warning depending on the results of ongoing
-            # experiments.
-            # Use this to return additional information as part of an error.
-            Tuple[Codes, JsonDict],
-            # Deprecated
-            bool,
-        ]
-    ],
+    Awaitable[Literal["NOT_SPAM"] | Codes | tuple[Codes, JsonDict] | bool],
 ]
 USER_MAY_SEND_STATE_EVENT_CALLBACK = Callable[
     [str, str, str, str, JsonDict],
-    Awaitable[
-        Union[
-            Literal["NOT_SPAM"],
-            Codes,
-            # Highly experimental, not officially part of the spamchecker API, may
-            # disappear without warning depending on the results of ongoing
-            # experiments.
-            # Use this to return additional information as part of an error.
-            Tuple[Codes, JsonDict],
-        ]
-    ],
-]
-CHECK_USERNAME_FOR_SPAM_CALLBACK = Union[
-    Callable[[UserProfile], Awaitable[bool]],
-    Callable[[UserProfile, str], Awaitable[bool]],
+    Awaitable[Literal["NOT_SPAM"] | Codes | tuple[Codes, JsonDict]],
 ]
+CHECK_USERNAME_FOR_SPAM_CALLBACK = (
+    Callable[[UserProfile], Awaitable[bool]]
+    | Callable[[UserProfile, str], Awaitable[bool]]
+)
 LEGACY_CHECK_REGISTRATION_FOR_SPAM_CALLBACK = Callable[
     [
-        Optional[dict],
-        Optional[str],
-        Collection[Tuple[str, str]],
+        dict | None,
+        str | None,
+        Collection[tuple[str, str]],
     ],
     Awaitable[RegistrationBehaviour],
 ]
 CHECK_REGISTRATION_FOR_SPAM_CALLBACK = Callable[
     [
-        Optional[dict],
-        Optional[str],
-        Collection[Tuple[str, str]],
-        Optional[str],
+        dict | None,
+        str | None,
+        Collection[tuple[str, str]],
+        str | None,
     ],
     Awaitable[RegistrationBehaviour],
 ]
 CHECK_MEDIA_FILE_FOR_SPAM_CALLBACK = Callable[
     [ReadableFileWrapper, FileInfo],
-    Awaitable[
-        Union[
-            Literal["NOT_SPAM"],
-            Codes,
-            # Highly experimental, not officially part of the spamchecker API, may
-            # disappear without warning depending on the results of ongoing
-            # experiments.
-            # Use this to return additional information as part of an error.
-            Tuple[Codes, JsonDict],
-            # Deprecated
-            bool,
-        ]
-    ],
+    Awaitable[Literal["NOT_SPAM"] | Codes | tuple[Codes, JsonDict] | bool],
 ]
 CHECK_LOGIN_FOR_SPAM_CALLBACK = Callable[
     [
         str,
-        Optional[str],
-        Optional[str],
-        Collection[Tuple[Optional[str], str]],
-        Optional[str],
-    ],
-    Awaitable[
-        Union[
-            Literal["NOT_SPAM"],
-            Codes,
-            # Highly experimental, not officially part of the spamchecker API, may
-            # disappear without warning depending on the results of ongoing
-            # experiments.
-            # Use this to return additional information as part of an error.
-            Tuple[Codes, JsonDict],
-        ]
+        str | None,
+        str | None,
+        Collection[tuple[str | None, str]],
+        str | None,
     ],
+    Awaitable[Literal["NOT_SPAM"] | Codes | tuple[Codes, JsonDict]],
 ]
 
 
@@ -266,7 +148,7 @@ def load_legacy_spam_checkers(hs: "synapse.server.HomeServer") -> None:
     """Wrapper that loads spam checkers configured using the old configuration, and
     registers the spam checker hooks they implement.
     """
-    spam_checkers: List[Any] = []
+    spam_checkers: list[Any] = []
     api = hs.get_module_api()
     for module, config in hs.config.spamchecker.spam_checkers:
         # Older spam checkers don't accept the `api` argument, so we
@@ -294,7 +176,7 @@ def load_legacy_spam_checkers(hs: "synapse.server.HomeServer") -> None:
     for spam_checker in spam_checkers:
         # Methods on legacy spam checkers might not be async, so we wrap them around a
         # wrapper that will call maybe_awaitable on the result.
-        def async_wrapper(f: Optional[Callable]) -> Optional[Callable[..., Awaitable]]:
+        def async_wrapper(f: Callable | None) -> Callable[..., Awaitable] | None:
             # f might be None if the callback isn't implemented by the module. In this
             # case we don't want to register a callback at all so we return None.
             if f is None:
@@ -310,11 +192,11 @@ def load_legacy_spam_checkers(hs: "synapse.server.HomeServer") -> None:
                     # that gives it only 3 arguments and drops the auth_provider_id on
                     # the floor.
                     def wrapper(
-                        email_threepid: Optional[dict],
-                        username: Optional[str],
-                        request_info: Collection[Tuple[str, str]],
-                        auth_provider_id: Optional[str],
-                    ) -> Union[Awaitable[RegistrationBehaviour], RegistrationBehaviour]:
+                        email_threepid: dict | None,
+                        username: str | None,
+                        request_info: Collection[tuple[str, str]],
+                        auth_provider_id: str | None,
+                    ) -> Awaitable[RegistrationBehaviour] | RegistrationBehaviour:
                         # Assertion required because mypy can't prove we won't
                         # change `f` back to `None`. See
                         # https://mypy.readthedocs.io/en/latest/common_issues.html#narrowing-and-inner-functions
@@ -359,59 +241,53 @@ class SpamCheckerModuleApiCallbacks:
         self.server_name = hs.hostname
         self.clock = hs.get_clock()
 
-        self._check_event_for_spam_callbacks: List[CHECK_EVENT_FOR_SPAM_CALLBACK] = []
-        self._should_drop_federated_event_callbacks: List[
+        self._check_event_for_spam_callbacks: list[CHECK_EVENT_FOR_SPAM_CALLBACK] = []
+        self._should_drop_federated_event_callbacks: list[
             SHOULD_DROP_FEDERATED_EVENT_CALLBACK
         ] = []
-        self._user_may_join_room_callbacks: List[USER_MAY_JOIN_ROOM_CALLBACK] = []
-        self._user_may_invite_callbacks: List[USER_MAY_INVITE_CALLBACK] = []
-        self._federated_user_may_invite_callbacks: List[
+        self._user_may_join_room_callbacks: list[USER_MAY_JOIN_ROOM_CALLBACK] = []
+        self._user_may_invite_callbacks: list[USER_MAY_INVITE_CALLBACK] = []
+        self._federated_user_may_invite_callbacks: list[
             FEDERATED_USER_MAY_INVITE_CALLBACK
         ] = []
-        self._user_may_send_3pid_invite_callbacks: List[
+        self._user_may_send_3pid_invite_callbacks: list[
             USER_MAY_SEND_3PID_INVITE_CALLBACK
         ] = []
-        self._user_may_create_room_callbacks: List[USER_MAY_CREATE_ROOM_CALLBACK] = []
-        self._user_may_send_state_event_callbacks: List[
+        self._user_may_create_room_callbacks: list[USER_MAY_CREATE_ROOM_CALLBACK] = []
+        self._user_may_send_state_event_callbacks: list[
             USER_MAY_SEND_STATE_EVENT_CALLBACK
         ] = []
-        self._user_may_create_room_alias_callbacks: List[
+        self._user_may_create_room_alias_callbacks: list[
             USER_MAY_CREATE_ROOM_ALIAS_CALLBACK
         ] = []
-        self._user_may_publish_room_callbacks: List[USER_MAY_PUBLISH_ROOM_CALLBACK] = []
-        self._check_username_for_spam_callbacks: List[
+        self._user_may_publish_room_callbacks: list[USER_MAY_PUBLISH_ROOM_CALLBACK] = []
+        self._check_username_for_spam_callbacks: list[
             CHECK_USERNAME_FOR_SPAM_CALLBACK
         ] = []
-        self._check_registration_for_spam_callbacks: List[
+        self._check_registration_for_spam_callbacks: list[
             CHECK_REGISTRATION_FOR_SPAM_CALLBACK
         ] = []
-        self._check_media_file_for_spam_callbacks: List[
+        self._check_media_file_for_spam_callbacks: list[
             CHECK_MEDIA_FILE_FOR_SPAM_CALLBACK
         ] = []
-        self._check_login_for_spam_callbacks: List[CHECK_LOGIN_FOR_SPAM_CALLBACK] = []
+        self._check_login_for_spam_callbacks: list[CHECK_LOGIN_FOR_SPAM_CALLBACK] = []
 
     def register_callbacks(
         self,
-        check_event_for_spam: Optional[CHECK_EVENT_FOR_SPAM_CALLBACK] = None,
-        should_drop_federated_event: Optional[
-            SHOULD_DROP_FEDERATED_EVENT_CALLBACK
-        ] = None,
-        user_may_join_room: Optional[USER_MAY_JOIN_ROOM_CALLBACK] = None,
-        user_may_invite: Optional[USER_MAY_INVITE_CALLBACK] = None,
-        federated_user_may_invite: Optional[FEDERATED_USER_MAY_INVITE_CALLBACK] = None,
-        user_may_send_3pid_invite: Optional[USER_MAY_SEND_3PID_INVITE_CALLBACK] = None,
-        user_may_create_room: Optional[USER_MAY_CREATE_ROOM_CALLBACK] = None,
-        user_may_create_room_alias: Optional[
-            USER_MAY_CREATE_ROOM_ALIAS_CALLBACK
-        ] = None,
-        user_may_publish_room: Optional[USER_MAY_PUBLISH_ROOM_CALLBACK] = None,
-        check_username_for_spam: Optional[CHECK_USERNAME_FOR_SPAM_CALLBACK] = None,
-        check_registration_for_spam: Optional[
-            CHECK_REGISTRATION_FOR_SPAM_CALLBACK
-        ] = None,
-        check_media_file_for_spam: Optional[CHECK_MEDIA_FILE_FOR_SPAM_CALLBACK] = None,
-        check_login_for_spam: Optional[CHECK_LOGIN_FOR_SPAM_CALLBACK] = None,
-        user_may_send_state_event: Optional[USER_MAY_SEND_STATE_EVENT_CALLBACK] = None,
+        check_event_for_spam: CHECK_EVENT_FOR_SPAM_CALLBACK | None = None,
+        should_drop_federated_event: SHOULD_DROP_FEDERATED_EVENT_CALLBACK | None = None,
+        user_may_join_room: USER_MAY_JOIN_ROOM_CALLBACK | None = None,
+        user_may_invite: USER_MAY_INVITE_CALLBACK | None = None,
+        federated_user_may_invite: FEDERATED_USER_MAY_INVITE_CALLBACK | None = None,
+        user_may_send_3pid_invite: USER_MAY_SEND_3PID_INVITE_CALLBACK | None = None,
+        user_may_create_room: USER_MAY_CREATE_ROOM_CALLBACK | None = None,
+        user_may_create_room_alias: USER_MAY_CREATE_ROOM_ALIAS_CALLBACK | None = None,
+        user_may_publish_room: USER_MAY_PUBLISH_ROOM_CALLBACK | None = None,
+        check_username_for_spam: CHECK_USERNAME_FOR_SPAM_CALLBACK | None = None,
+        check_registration_for_spam: CHECK_REGISTRATION_FOR_SPAM_CALLBACK | None = None,
+        check_media_file_for_spam: CHECK_MEDIA_FILE_FOR_SPAM_CALLBACK | None = None,
+        check_login_for_spam: CHECK_LOGIN_FOR_SPAM_CALLBACK | None = None,
+        user_may_send_state_event: USER_MAY_SEND_STATE_EVENT_CALLBACK | None = None,
     ) -> None:
         """Register callbacks from module for each hook."""
         if check_event_for_spam is not None:
@@ -471,7 +347,7 @@ class SpamCheckerModuleApiCallbacks:
     @trace
     async def check_event_for_spam(
         self, event: "synapse.events.EventBase"
-    ) -> Union[Tuple[Codes, JsonDict], str]:
+    ) -> tuple[Codes, JsonDict] | str:
         """Checks if a given event is considered "spammy" by this server.
 
         If the server considers an event spammy, then it will be rejected if
@@ -534,7 +410,7 @@ class SpamCheckerModuleApiCallbacks:
 
     async def should_drop_federated_event(
         self, event: "synapse.events.EventBase"
-    ) -> Union[bool, str]:
+    ) -> bool | str:
         """Checks if a given federated event is considered "spammy" by this
         server.
 
@@ -553,7 +429,7 @@ class SpamCheckerModuleApiCallbacks:
                 name=f"{callback.__module__}.{callback.__qualname__}",
                 server_name=self.server_name,
             ):
-                res: Union[bool, str] = await delay_cancellation(callback(event))
+                res: bool | str = await delay_cancellation(callback(event))
             if res:
                 return res
 
@@ -561,7 +437,7 @@ class SpamCheckerModuleApiCallbacks:
 
     async def user_may_join_room(
         self, user_id: str, room_id: str, is_invited: bool
-    ) -> Union[Tuple[Codes, JsonDict], Literal["NOT_SPAM"]]:
+    ) -> tuple[Codes, JsonDict] | Literal["NOT_SPAM"]:
         """Checks if a given users is allowed to join a room.
         Not called when a user creates a room.
 
@@ -605,7 +481,7 @@ class SpamCheckerModuleApiCallbacks:
 
     async def user_may_invite(
         self, inviter_userid: str, invitee_userid: str, room_id: str
-    ) -> Union[Tuple[Codes, dict], Literal["NOT_SPAM"]]:
+    ) -> tuple[Codes, dict] | Literal["NOT_SPAM"]:
         """Checks if a given user may send an invite
 
         Args:
@@ -650,7 +526,7 @@ class SpamCheckerModuleApiCallbacks:
 
     async def federated_user_may_invite(
         self, event: "synapse.events.EventBase"
-    ) -> Union[Tuple[Codes, dict], Literal["NOT_SPAM"]]:
+    ) -> tuple[Codes, dict] | Literal["NOT_SPAM"]:
         """Checks if a given user may send an invite
 
         Args:
@@ -691,7 +567,7 @@ class SpamCheckerModuleApiCallbacks:
 
     async def user_may_send_3pid_invite(
         self, inviter_userid: str, medium: str, address: str, room_id: str
-    ) -> Union[Tuple[Codes, dict], Literal["NOT_SPAM"]]:
+    ) -> tuple[Codes, dict] | Literal["NOT_SPAM"]:
         """Checks if a given user may invite a given threepid into the room
 
         Note that if the threepid is already associated with a Matrix user ID, Synapse
@@ -739,7 +615,7 @@ class SpamCheckerModuleApiCallbacks:
 
     async def user_may_create_room(
         self, userid: str, room_config: JsonDict
-    ) -> Union[Tuple[Codes, dict], Literal["NOT_SPAM"]]:
+    ) -> tuple[Codes, dict] | Literal["NOT_SPAM"]:
         """Checks if a given user may create a room
 
         Args:
@@ -805,7 +681,7 @@ class SpamCheckerModuleApiCallbacks:
         event_type: str,
         state_key: str,
         content: JsonDict,
-    ) -> Union[Tuple[Codes, dict], Literal["NOT_SPAM"]]:
+    ) -> tuple[Codes, dict] | Literal["NOT_SPAM"]:
         """Checks if a given user may create a room with a given visibility
         Args:
             user_id: The ID of the user attempting to create a room
@@ -838,7 +714,7 @@ class SpamCheckerModuleApiCallbacks:
 
     async def user_may_create_room_alias(
         self, userid: str, room_alias: RoomAlias
-    ) -> Union[Tuple[Codes, dict], Literal["NOT_SPAM"]]:
+    ) -> tuple[Codes, dict] | Literal["NOT_SPAM"]:
         """Checks if a given user may create a room alias
 
         Args:
@@ -876,7 +752,7 @@ class SpamCheckerModuleApiCallbacks:
 
     async def user_may_publish_room(
         self, userid: str, room_id: str
-    ) -> Union[Tuple[Codes, dict], Literal["NOT_SPAM"]]:
+    ) -> tuple[Codes, dict] | Literal["NOT_SPAM"]:
         """Checks if a given user may publish a room to the directory
 
         Args:
@@ -962,10 +838,10 @@ class SpamCheckerModuleApiCallbacks:
 
     async def check_registration_for_spam(
         self,
-        email_threepid: Optional[dict],
-        username: Optional[str],
-        request_info: Collection[Tuple[str, str]],
-        auth_provider_id: Optional[str] = None,
+        email_threepid: dict | None,
+        username: str | None,
+        request_info: Collection[tuple[str, str]],
+        auth_provider_id: str | None = None,
     ) -> RegistrationBehaviour:
         """Checks if we should allow the given registration request.
 
@@ -1000,7 +876,7 @@ class SpamCheckerModuleApiCallbacks:
     @trace
     async def check_media_file_for_spam(
         self, file_wrapper: ReadableFileWrapper, file_info: FileInfo
-    ) -> Union[Tuple[Codes, dict], Literal["NOT_SPAM"]]:
+    ) -> tuple[Codes, dict] | Literal["NOT_SPAM"]:
         """Checks if a piece of newly uploaded media should be blocked.
 
         This will be called for local uploads, downloads of remote media, each
@@ -1013,7 +889,7 @@ class SpamCheckerModuleApiCallbacks:
 
             async def check_media_file_for_spam(
                 self, file: ReadableFileWrapper, file_info: FileInfo
-            ) -> Union[Codes, Literal["NOT_SPAM"]]:
+            ) -> Codes | Literal["NOT_SPAM"]:
                 buffer = BytesIO()
                 await file.write_chunks_to(buffer.write)
 
@@ -1060,11 +936,11 @@ class SpamCheckerModuleApiCallbacks:
     async def check_login_for_spam(
         self,
         user_id: str,
-        device_id: Optional[str],
-        initial_display_name: Optional[str],
-        request_info: Collection[Tuple[Optional[str], str]],
-        auth_provider_id: Optional[str] = None,
-    ) -> Union[Tuple[Codes, dict], Literal["NOT_SPAM"]]:
+        device_id: str | None,
+        initial_display_name: str | None,
+        request_info: Collection[tuple[str | None, str]],
+        auth_provider_id: str | None = None,
+    ) -> tuple[Codes, dict] | Literal["NOT_SPAM"]:
         """Checks if we should allow the given registration request.
 
         Args:
diff --git a/synapse/module_api/callbacks/third_party_event_rules_callbacks.py b/synapse/module_api/callbacks/third_party_event_rules_callbacks.py
index 9f7a04372d..65f5a6b183 100644
--- a/synapse/module_api/callbacks/third_party_event_rules_callbacks.py
+++ b/synapse/module_api/callbacks/third_party_event_rules_callbacks.py
@@ -19,7 +19,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, Any, Awaitable, Callable, List, Optional, Tuple
+from typing import TYPE_CHECKING, Any, Awaitable, Callable
 
 from twisted.internet.defer import CancelledError
 
@@ -37,7 +37,7 @@ logger = logging.getLogger(__name__)
 
 
 CHECK_EVENT_ALLOWED_CALLBACK = Callable[
-    [EventBase, StateMap[EventBase]], Awaitable[Tuple[bool, Optional[dict]]]
+    [EventBase, StateMap[EventBase]], Awaitable[tuple[bool, dict | None]]
 ]
 ON_CREATE_ROOM_CALLBACK = Callable[[Requester, dict, bool], Awaitable]
 CHECK_THREEPID_CAN_BE_INVITED_CALLBACK = Callable[
@@ -47,7 +47,7 @@ CHECK_VISIBILITY_CAN_BE_MODIFIED_CALLBACK = Callable[
     [str, StateMap[EventBase], str], Awaitable[bool]
 ]
 ON_NEW_EVENT_CALLBACK = Callable[[EventBase, StateMap[EventBase]], Awaitable]
-CHECK_CAN_SHUTDOWN_ROOM_CALLBACK = Callable[[Optional[str], str], Awaitable[bool]]
+CHECK_CAN_SHUTDOWN_ROOM_CALLBACK = Callable[[str | None, str], Awaitable[bool]]
 CHECK_CAN_DEACTIVATE_USER_CALLBACK = Callable[[str, bool], Awaitable[bool]]
 ON_PROFILE_UPDATE_CALLBACK = Callable[[str, ProfileInfo, bool, bool], Awaitable]
 ON_USER_DEACTIVATION_STATUS_CHANGED_CALLBACK = Callable[[str, bool, bool], Awaitable]
@@ -77,7 +77,7 @@ def load_legacy_third_party_event_rules(hs: "HomeServer") -> None:
         "check_visibility_can_be_modified",
     }
 
-    def async_wrapper(f: Optional[Callable]) -> Optional[Callable[..., Awaitable]]:
+    def async_wrapper(f: Callable | None) -> Callable[..., Awaitable] | None:
         # f might be None if the callback isn't implemented by the module. In this
         # case we don't want to register a callback at all so we return None.
         if f is None:
@@ -93,7 +93,7 @@ def load_legacy_third_party_event_rules(hs: "HomeServer") -> None:
             async def wrap_check_event_allowed(
                 event: EventBase,
                 state_events: StateMap[EventBase],
-            ) -> Tuple[bool, Optional[dict]]:
+            ) -> tuple[bool, dict | None]:
                 # Assertion required because mypy can't prove we won't change
                 # `f` back to `None`. See
                 # https://mypy.readthedocs.io/en/latest/common_issues.html#narrowing-and-inner-functions
@@ -159,57 +159,52 @@ class ThirdPartyEventRulesModuleApiCallbacks:
         self.store = hs.get_datastores().main
         self._storage_controllers = hs.get_storage_controllers()
 
-        self._check_event_allowed_callbacks: List[CHECK_EVENT_ALLOWED_CALLBACK] = []
-        self._on_create_room_callbacks: List[ON_CREATE_ROOM_CALLBACK] = []
-        self._check_threepid_can_be_invited_callbacks: List[
+        self._check_event_allowed_callbacks: list[CHECK_EVENT_ALLOWED_CALLBACK] = []
+        self._on_create_room_callbacks: list[ON_CREATE_ROOM_CALLBACK] = []
+        self._check_threepid_can_be_invited_callbacks: list[
             CHECK_THREEPID_CAN_BE_INVITED_CALLBACK
         ] = []
-        self._check_visibility_can_be_modified_callbacks: List[
+        self._check_visibility_can_be_modified_callbacks: list[
             CHECK_VISIBILITY_CAN_BE_MODIFIED_CALLBACK
         ] = []
-        self._on_new_event_callbacks: List[ON_NEW_EVENT_CALLBACK] = []
-        self._check_can_shutdown_room_callbacks: List[
+        self._on_new_event_callbacks: list[ON_NEW_EVENT_CALLBACK] = []
+        self._check_can_shutdown_room_callbacks: list[
             CHECK_CAN_SHUTDOWN_ROOM_CALLBACK
         ] = []
-        self._check_can_deactivate_user_callbacks: List[
+        self._check_can_deactivate_user_callbacks: list[
             CHECK_CAN_DEACTIVATE_USER_CALLBACK
         ] = []
-        self._on_profile_update_callbacks: List[ON_PROFILE_UPDATE_CALLBACK] = []
-        self._on_user_deactivation_status_changed_callbacks: List[
+        self._on_profile_update_callbacks: list[ON_PROFILE_UPDATE_CALLBACK] = []
+        self._on_user_deactivation_status_changed_callbacks: list[
             ON_USER_DEACTIVATION_STATUS_CHANGED_CALLBACK
         ] = []
-        self._on_threepid_bind_callbacks: List[ON_THREEPID_BIND_CALLBACK] = []
-        self._on_add_user_third_party_identifier_callbacks: List[
+        self._on_threepid_bind_callbacks: list[ON_THREEPID_BIND_CALLBACK] = []
+        self._on_add_user_third_party_identifier_callbacks: list[
             ON_ADD_USER_THIRD_PARTY_IDENTIFIER_CALLBACK
         ] = []
-        self._on_remove_user_third_party_identifier_callbacks: List[
+        self._on_remove_user_third_party_identifier_callbacks: list[
             ON_REMOVE_USER_THIRD_PARTY_IDENTIFIER_CALLBACK
         ] = []
 
     def register_third_party_rules_callbacks(
         self,
-        check_event_allowed: Optional[CHECK_EVENT_ALLOWED_CALLBACK] = None,
-        on_create_room: Optional[ON_CREATE_ROOM_CALLBACK] = None,
-        check_threepid_can_be_invited: Optional[
-            CHECK_THREEPID_CAN_BE_INVITED_CALLBACK
-        ] = None,
-        check_visibility_can_be_modified: Optional[
-            CHECK_VISIBILITY_CAN_BE_MODIFIED_CALLBACK
-        ] = None,
-        on_new_event: Optional[ON_NEW_EVENT_CALLBACK] = None,
-        check_can_shutdown_room: Optional[CHECK_CAN_SHUTDOWN_ROOM_CALLBACK] = None,
-        check_can_deactivate_user: Optional[CHECK_CAN_DEACTIVATE_USER_CALLBACK] = None,
-        on_profile_update: Optional[ON_PROFILE_UPDATE_CALLBACK] = None,
-        on_user_deactivation_status_changed: Optional[
-            ON_USER_DEACTIVATION_STATUS_CHANGED_CALLBACK
-        ] = None,
-        on_threepid_bind: Optional[ON_THREEPID_BIND_CALLBACK] = None,
-        on_add_user_third_party_identifier: Optional[
-            ON_ADD_USER_THIRD_PARTY_IDENTIFIER_CALLBACK
-        ] = None,
-        on_remove_user_third_party_identifier: Optional[
-            ON_REMOVE_USER_THIRD_PARTY_IDENTIFIER_CALLBACK
-        ] = None,
+        check_event_allowed: CHECK_EVENT_ALLOWED_CALLBACK | None = None,
+        on_create_room: ON_CREATE_ROOM_CALLBACK | None = None,
+        check_threepid_can_be_invited: CHECK_THREEPID_CAN_BE_INVITED_CALLBACK
+        | None = None,
+        check_visibility_can_be_modified: CHECK_VISIBILITY_CAN_BE_MODIFIED_CALLBACK
+        | None = None,
+        on_new_event: ON_NEW_EVENT_CALLBACK | None = None,
+        check_can_shutdown_room: CHECK_CAN_SHUTDOWN_ROOM_CALLBACK | None = None,
+        check_can_deactivate_user: CHECK_CAN_DEACTIVATE_USER_CALLBACK | None = None,
+        on_profile_update: ON_PROFILE_UPDATE_CALLBACK | None = None,
+        on_user_deactivation_status_changed: ON_USER_DEACTIVATION_STATUS_CHANGED_CALLBACK
+        | None = None,
+        on_threepid_bind: ON_THREEPID_BIND_CALLBACK | None = None,
+        on_add_user_third_party_identifier: ON_ADD_USER_THIRD_PARTY_IDENTIFIER_CALLBACK
+        | None = None,
+        on_remove_user_third_party_identifier: ON_REMOVE_USER_THIRD_PARTY_IDENTIFIER_CALLBACK
+        | None = None,
     ) -> None:
         """Register callbacks from modules for each hook."""
         if check_event_allowed is not None:
@@ -261,7 +256,7 @@ class ThirdPartyEventRulesModuleApiCallbacks:
         self,
         event: EventBase,
         context: UnpersistedEventContextBase,
-    ) -> Tuple[bool, Optional[dict]]:
+    ) -> tuple[bool, dict | None]:
         """Check if a provided event should be allowed in the given context.
 
         The module can return:
@@ -443,9 +438,7 @@ class ThirdPartyEventRulesModuleApiCallbacks:
                     "Failed to run module API callback %s: %s", callback, e
                 )
 
-    async def check_can_shutdown_room(
-        self, user_id: Optional[str], room_id: str
-    ) -> bool:
+    async def check_can_shutdown_room(self, user_id: str | None, room_id: str) -> bool:
         """Intercept requests to shutdown a room. If `False` is returned, the
          room must not be shut down.
 
diff --git a/synapse/notifier.py b/synapse/notifier.py
index e684df4866..260a2c0d87 100644
--- a/synapse/notifier.py
+++ b/synapse/notifier.py
@@ -25,16 +25,10 @@ from typing import (
     Awaitable,
     Callable,
     Collection,
-    Dict,
     Iterable,
-    List,
     Literal,
     Mapping,
-    Optional,
-    Set,
-    Tuple,
     TypeVar,
-    Union,
     overload,
 )
 
@@ -148,7 +142,7 @@ class _NotifierUserStream:
         self.last_notified_ms = time_now_ms
 
         # Set of listeners that we need to wake up when there has been a change.
-        self.listeners: Set[Deferred[StreamToken]] = set()
+        self.listeners: set[Deferred[StreamToken]] = set()
 
     def update_and_fetch_deferreds(
         self,
@@ -215,7 +209,7 @@ class _NotifierUserStream:
 
 @attr.s(slots=True, frozen=True, auto_attribs=True)
 class EventStreamResult:
-    events: List[Union[JsonDict, EventBase]]
+    events: list[JsonDict | EventBase]
     start_token: StreamToken
     end_token: StreamToken
 
@@ -230,8 +224,8 @@ class _PendingRoomEventEntry:
 
     room_id: str
     type: str
-    state_key: Optional[str]
-    membership: Optional[str]
+    state_key: str | None
+    membership: str | None
 
 
 class Notifier:
@@ -244,25 +238,25 @@ class Notifier:
     UNUSED_STREAM_EXPIRY_MS = 10 * 60 * 1000
 
     def __init__(self, hs: "HomeServer"):
-        self.user_to_user_stream: Dict[str, _NotifierUserStream] = {}
-        self.room_to_user_streams: Dict[str, Set[_NotifierUserStream]] = {}
+        self.user_to_user_stream: dict[str, _NotifierUserStream] = {}
+        self.room_to_user_streams: dict[str, set[_NotifierUserStream]] = {}
 
         self.hs = hs
         self.server_name = hs.hostname
         self._storage_controllers = hs.get_storage_controllers()
         self.event_sources = hs.get_event_sources()
         self.store = hs.get_datastores().main
-        self.pending_new_room_events: List[_PendingRoomEventEntry] = []
+        self.pending_new_room_events: list[_PendingRoomEventEntry] = []
 
         self._replication_notifier = hs.get_replication_notifier()
-        self._new_join_in_room_callbacks: List[Callable[[str, str], None]] = []
+        self._new_join_in_room_callbacks: list[Callable[[str, str], None]] = []
 
         self._federation_client = hs.get_federation_http_client()
 
         self._third_party_rules = hs.get_module_api_callbacks().third_party_event_rules
 
         # List of callbacks to be notified when a lock is released
-        self._lock_released_callback: List[Callable[[str, str, str], None]] = []
+        self._lock_released_callback: list[Callable[[str, str, str], None]] = []
 
         self.reactor = hs.get_reactor()
         self.clock = hs.get_clock()
@@ -283,10 +277,10 @@ class Notifier:
         # when rendering the metrics page, which is likely once per minute at
         # most when scraping it.
         #
-        # Ideally, we'd use `Mapping[Tuple[str], int]` here but mypy doesn't like it.
+        # Ideally, we'd use `Mapping[tuple[str], int]` here but mypy doesn't like it.
         # This is close enough and better than a type ignore.
-        def count_listeners() -> Mapping[Tuple[str, ...], int]:
-            all_user_streams: Set[_NotifierUserStream] = set()
+        def count_listeners() -> Mapping[tuple[str, ...], int]:
+            all_user_streams: set[_NotifierUserStream] = set()
 
             for streams in list(self.room_to_user_streams.values()):
                 all_user_streams |= streams
@@ -338,9 +332,9 @@ class Notifier:
 
     async def on_new_room_events(
         self,
-        events_and_pos: List[Tuple[EventBase, PersistedEventPosition]],
+        events_and_pos: list[tuple[EventBase, PersistedEventPosition]],
         max_room_stream_token: RoomStreamToken,
-        extra_users: Optional[Collection[UserID]] = None,
+        extra_users: Collection[UserID] | None = None,
     ) -> None:
         """Creates a _PendingRoomEventEntry for each of the listed events and calls
         notify_new_room_events with the results."""
@@ -373,7 +367,7 @@ class Notifier:
         time_now_ms = self.clock.time_msec()
         current_token = self.event_sources.get_current_token()
 
-        listeners: List["Deferred[StreamToken]"] = []
+        listeners: list["Deferred[StreamToken]"] = []
         for user_stream in user_streams:
             try:
                 listeners.extend(
@@ -397,7 +391,7 @@ class Notifier:
 
     async def notify_new_room_events(
         self,
-        event_entries: List[Tuple[_PendingRoomEventEntry, str]],
+        event_entries: list[tuple[_PendingRoomEventEntry, str]],
         max_room_stream_token: RoomStreamToken,
     ) -> None:
         """Used by handlers to inform the notifier something has happened
@@ -425,11 +419,11 @@ class Notifier:
     def create_pending_room_event_entry(
         self,
         event_pos: PersistedEventPosition,
-        extra_users: Optional[Collection[UserID]],
+        extra_users: Collection[UserID] | None,
         room_id: str,
         event_type: str,
-        state_key: Optional[str],
-        membership: Optional[str],
+        state_key: str | None,
+        membership: str | None,
     ) -> _PendingRoomEventEntry:
         """Creates and returns a _PendingRoomEventEntry"""
         return _PendingRoomEventEntry(
@@ -453,8 +447,8 @@ class Notifier:
         pending = self.pending_new_room_events
         self.pending_new_room_events = []
 
-        users: Set[UserID] = set()
-        rooms: Set[str] = set()
+        users: set[UserID] = set()
+        rooms: set[str] = set()
 
         for entry in pending:
             if entry.event_pos.persisted_after(max_room_stream_token):
@@ -508,8 +502,8 @@ class Notifier:
         self,
         stream_key: Literal[StreamKeyType.ROOM],
         new_token: RoomStreamToken,
-        users: Optional[Collection[Union[str, UserID]]] = None,
-        rooms: Optional[StrCollection] = None,
+        users: Collection[str | UserID] | None = None,
+        rooms: StrCollection | None = None,
     ) -> None: ...
 
     @overload
@@ -517,8 +511,8 @@ class Notifier:
         self,
         stream_key: Literal[StreamKeyType.RECEIPT],
         new_token: MultiWriterStreamToken,
-        users: Optional[Collection[Union[str, UserID]]] = None,
-        rooms: Optional[StrCollection] = None,
+        users: Collection[str | UserID] | None = None,
+        rooms: StrCollection | None = None,
     ) -> None: ...
 
     @overload
@@ -535,16 +529,16 @@ class Notifier:
             StreamKeyType.THREAD_SUBSCRIPTIONS,
         ],
         new_token: int,
-        users: Optional[Collection[Union[str, UserID]]] = None,
-        rooms: Optional[StrCollection] = None,
+        users: Collection[str | UserID] | None = None,
+        rooms: StrCollection | None = None,
     ) -> None: ...
 
     def on_new_event(
         self,
         stream_key: StreamKeyType,
-        new_token: Union[int, RoomStreamToken, MultiWriterStreamToken],
-        users: Optional[Collection[Union[str, UserID]]] = None,
-        rooms: Optional[StrCollection] = None,
+        new_token: int | RoomStreamToken | MultiWriterStreamToken,
+        users: Collection[str | UserID] | None = None,
+        rooms: StrCollection | None = None,
     ) -> None:
         """Used to inform listeners that something has happened event wise.
 
@@ -560,7 +554,7 @@ class Notifier:
         users = users or []
         rooms = rooms or []
 
-        user_streams: Set[_NotifierUserStream] = set()
+        user_streams: set[_NotifierUserStream] = set()
 
         log_kv(
             {
@@ -593,7 +587,7 @@ class Notifier:
 
             time_now_ms = self.clock.time_msec()
             current_token = self.event_sources.get_current_token()
-            listeners: List["Deferred[StreamToken]"] = []
+            listeners: list["Deferred[StreamToken]"] = []
             for user_stream in user_streams:
                 try:
                     listeners.extend(
@@ -640,7 +634,7 @@ class Notifier:
         user_id: str,
         timeout: int,
         callback: Callable[[StreamToken, StreamToken], Awaitable[T]],
-        room_ids: Optional[StrCollection] = None,
+        room_ids: StrCollection | None = None,
         from_token: StreamToken = StreamToken.START,
     ) -> T:
         """Wait until the callback returns a non empty response or the
@@ -676,9 +670,16 @@ class Notifier:
                         # is a new token.
                         listener = user_stream.new_listener(prev_token)
                         listener = timeout_deferred(
-                            listener,
-                            (end_time - now) / 1000.0,
-                            self.hs.get_reactor(),
+                            deferred=listener,
+                            timeout=(end_time - now) / 1000.0,
+                            # We don't track these calls since they are constantly being
+                            # overridden by new calls to /sync and they don't hold the
+                            # `HomeServer` in memory on shutdown. It is safe to let them
+                            # timeout of their own accord after shutting down since it
+                            # won't delay shutdown and there won't be any adverse
+                            # behaviour.
+                            cancel_on_shutdown=False,
+                            clock=self.hs.get_clock(),
                         )
 
                         log_kv(
@@ -734,7 +735,7 @@ class Notifier:
         pagination_config: PaginationConfig,
         timeout: int,
         is_guest: bool = False,
-        explicit_room_id: Optional[str] = None,
+        explicit_room_id: str | None = None,
     ) -> EventStreamResult:
         """For the given user and rooms, return any new events for them. If
         there are no new events wait for up to `timeout` milliseconds for any
@@ -764,7 +765,7 @@ class Notifier:
             # The events fetched from each source are a JsonDict, EventBase, or
             # UserPresenceState, but see below for UserPresenceState being
             # converted to JsonDict.
-            events: List[Union[JsonDict, EventBase]] = []
+            events: list[JsonDict | EventBase] = []
             end_token = from_token
 
             for keyname, source in self.event_sources.sources.get_sources():
@@ -863,8 +864,8 @@ class Notifier:
             await self.clock.sleep(0.5)
 
     async def _get_room_ids(
-        self, user: UserID, explicit_room_id: Optional[str]
-    ) -> Tuple[StrCollection, bool]:
+        self, user: UserID, explicit_room_id: str | None
+    ) -> tuple[StrCollection, bool]:
         joined_room_ids = await self.store.get_rooms_for_user(user.to_string())
         if explicit_room_id:
             if explicit_room_id in joined_room_ids:
@@ -953,7 +954,7 @@ class ReplicationNotifier:
     This is separate from the notifier to avoid circular dependencies.
     """
 
-    _replication_callbacks: List[Callable[[], None]] = attr.Factory(list)
+    _replication_callbacks: list[Callable[[], None]] = attr.Factory(list)
 
     def add_replication_callback(self, cb: Callable[[], None]) -> None:
         """Add a callback that will be called when some new data is available.
diff --git a/synapse/push/__init__.py b/synapse/push/__init__.py
index 7bc99bd785..58c58fbdbf 100644
--- a/synapse/push/__init__.py
+++ b/synapse/push/__init__.py
@@ -94,7 +94,7 @@ The Pusher instance also calls out to various utilities for generating payloads
 """
 
 import abc
-from typing import TYPE_CHECKING, Any, Dict, Optional
+from typing import TYPE_CHECKING, Any
 
 import attr
 
@@ -108,7 +108,7 @@ if TYPE_CHECKING:
 class PusherConfig:
     """Parameters necessary to configure a pusher."""
 
-    id: Optional[int]
+    id: int | None
     user_name: str
 
     profile_tag: str
@@ -118,20 +118,20 @@ class PusherConfig:
     device_display_name: str
     pushkey: str
     ts: int
-    lang: Optional[str]
-    data: Optional[JsonDict]
+    lang: str | None
+    data: JsonDict | None
     last_stream_ordering: int
-    last_success: Optional[int]
-    failing_since: Optional[int]
+    last_success: int | None
+    failing_since: int | None
     enabled: bool
-    device_id: Optional[str]
+    device_id: str | None
 
     # XXX(quenting): The access_token is not persisted anymore for new pushers, but we
     # keep it when reading from the database, so that we don't get stale pushers
     # while the "set_device_id_for_pushers" background update is running.
-    access_token: Optional[int]
+    access_token: int | None
 
-    def as_dict(self) -> Dict[str, Any]:
+    def as_dict(self) -> dict[str, Any]:
         """Information that can be retrieved about a pusher after creation."""
         return {
             "app_display_name": self.app_display_name,
diff --git a/synapse/push/bulk_push_rule_evaluator.py b/synapse/push/bulk_push_rule_evaluator.py
index ea9169aef0..7cf89200a8 100644
--- a/synapse/push/bulk_push_rule_evaluator.py
+++ b/synapse/push/bulk_push_rule_evaluator.py
@@ -24,14 +24,8 @@ from typing import (
     TYPE_CHECKING,
     Any,
     Collection,
-    Dict,
-    FrozenSet,
-    List,
     Mapping,
-    Optional,
     Sequence,
-    Tuple,
-    Union,
     cast,
 )
 
@@ -237,7 +231,7 @@ class BulkPushRuleEvaluator:
         event: EventBase,
         context: EventContext,
         event_id_to_event: Mapping[str, EventBase],
-    ) -> Tuple[dict, Optional[int]]:
+    ) -> tuple[dict, int | None]:
         """
         Given an event and an event context, get the power level event relevant to the event
         and the power level of the sender of the event.
@@ -309,13 +303,13 @@ class BulkPushRuleEvaluator:
 
     async def _related_events(
         self, event: EventBase
-    ) -> Dict[str, Dict[str, JsonValue]]:
+    ) -> dict[str, dict[str, JsonValue]]:
         """Fetches the related events for 'event'. Sets the im.vector.is_falling_back key if the event is from a fallback relation
 
         Returns:
             Mapping of relation type to flattened events.
         """
-        related_events: Dict[str, Dict[str, JsonValue]] = {}
+        related_events: dict[str, dict[str, JsonValue]] = {}
         if self._related_event_match_enabled:
             related_event_id = event.content.get("m.relates_to", {}).get("event_id")
             relation_type = event.content.get("m.relates_to", {}).get("rel_type")
@@ -352,7 +346,7 @@ class BulkPushRuleEvaluator:
         return related_events
 
     async def action_for_events_by_user(
-        self, events_and_context: List[EventPersistencePair]
+        self, events_and_context: list[EventPersistencePair]
     ) -> None:
         """Given a list of events and their associated contexts, evaluate the push rules
         for each event, check if the message should increment the unread count, and
@@ -394,7 +388,7 @@ class BulkPushRuleEvaluator:
             count_as_unread = _should_count_as_unread(event, context)
 
         rules_by_user = await self._get_rules_for_event(event)
-        actions_by_user: Dict[str, Collection[Union[Mapping, str]]] = {}
+        actions_by_user: dict[str, Collection[Mapping | str]] = {}
 
         # Gather a bunch of info in parallel.
         #
@@ -409,7 +403,7 @@ class BulkPushRuleEvaluator:
             profiles,
         ) = await make_deferred_yieldable(
             cast(
-                "Deferred[Tuple[int, Tuple[dict, Optional[int]], Dict[str, Dict[str, JsonValue]], Mapping[str, ProfileInfo]]]",
+                "Deferred[tuple[int, tuple[dict, int | None], dict[str, dict[str, JsonValue]], Mapping[str, ProfileInfo]]]",
                 gather_results(
                     (
                         run_in_background(  # type: ignore[call-overload]
@@ -481,7 +475,7 @@ class BulkPushRuleEvaluator:
             self.hs.config.experimental.msc4306_enabled,
         )
 
-        msc4306_thread_subscribers: Optional[FrozenSet[str]] = None
+        msc4306_thread_subscribers: frozenset[str] | None = None
         if self.hs.config.experimental.msc4306_enabled and thread_id != MAIN_TIMELINE:
             # pull out, in batch, all local subscribers to this thread
             # (in the common case, they will all be getting processed for push
@@ -514,7 +508,7 @@ class BulkPushRuleEvaluator:
                 # current user, it'll be added to the dict later.
                 actions_by_user[uid] = []
 
-            msc4306_thread_subscription_state: Optional[bool] = None
+            msc4306_thread_subscription_state: bool | None = None
             if msc4306_thread_subscribers is not None:
                 msc4306_thread_subscription_state = uid in msc4306_thread_subscribers
 
@@ -556,10 +550,10 @@ class BulkPushRuleEvaluator:
         )
 
 
-MemberMap = Dict[str, Optional[EventIdMembership]]
-Rule = Dict[str, dict]
-RulesByUser = Dict[str, List[Rule]]
-StateGroup = Union[object, int]
+MemberMap = dict[str, EventIdMembership | None]
+Rule = dict[str, dict]
+RulesByUser = dict[str, list[Rule]]
+StateGroup = object | int
 
 
 def _is_simple_value(value: Any) -> bool:
@@ -571,10 +565,10 @@ def _is_simple_value(value: Any) -> bool:
 
 
 def _flatten_dict(
-    d: Union[EventBase, Mapping[str, Any]],
-    prefix: Optional[List[str]] = None,
-    result: Optional[Dict[str, JsonValue]] = None,
-) -> Dict[str, JsonValue]:
+    d: EventBase | Mapping[str, Any],
+    prefix: list[str] | None = None,
+    result: dict[str, JsonValue] | None = None,
+) -> dict[str, JsonValue]:
     """
     Given a JSON dictionary (or event) which might contain sub dictionaries,
     flatten it into a single layer dictionary by combining the keys & sub-keys.
diff --git a/synapse/push/clientformat.py b/synapse/push/clientformat.py
index 4f647491f1..db082e295d 100644
--- a/synapse/push/clientformat.py
+++ b/synapse/push/clientformat.py
@@ -20,7 +20,7 @@
 #
 
 import copy
-from typing import Any, Dict, List, Optional
+from typing import Any
 
 from synapse.push.rulekinds import PRIORITY_CLASS_INVERSE_MAP, PRIORITY_CLASS_MAP
 from synapse.synapse_rust.push import FilteredPushRules, PushRule
@@ -29,11 +29,11 @@ from synapse.types import UserID
 
 def format_push_rules_for_user(
     user: UserID, ruleslist: FilteredPushRules
-) -> Dict[str, Dict[str, List[Dict[str, Any]]]]:
+) -> dict[str, dict[str, list[dict[str, Any]]]]:
     """Converts a list of rawrules and a enabled map into nested dictionaries
     to match the Matrix client-server format for push rules"""
 
-    rules: Dict[str, Dict[str, List[Dict[str, Any]]]] = {"global": {}}
+    rules: dict[str, dict[str, list[dict[str, Any]]]] = {"global": {}}
 
     rules["global"] = _add_empty_priority_class_arrays(rules["global"])
 
@@ -70,7 +70,7 @@ def format_push_rules_for_user(
     return rules
 
 
-def _convert_type_to_value(rule_or_cond: Dict[str, Any], user: UserID) -> None:
+def _convert_type_to_value(rule_or_cond: dict[str, Any], user: UserID) -> None:
     for type_key in ("pattern", "value"):
         type_value = rule_or_cond.pop(f"{type_key}_type", None)
         if type_value == "user_id":
@@ -79,14 +79,14 @@ def _convert_type_to_value(rule_or_cond: Dict[str, Any], user: UserID) -> None:
             rule_or_cond[type_key] = user.localpart
 
 
-def _add_empty_priority_class_arrays(d: Dict[str, list]) -> Dict[str, list]:
+def _add_empty_priority_class_arrays(d: dict[str, list]) -> dict[str, list]:
     for pc in PRIORITY_CLASS_MAP.keys():
         d[pc] = []
     return d
 
 
-def _rule_to_template(rule: PushRule) -> Optional[Dict[str, Any]]:
-    templaterule: Dict[str, Any]
+def _rule_to_template(rule: PushRule) -> dict[str, Any] | None:
+    templaterule: dict[str, Any]
 
     unscoped_rule_id = _rule_id_from_namespaced(rule.rule_id)
 
diff --git a/synapse/push/emailpusher.py b/synapse/push/emailpusher.py
index 09ca14584a..36dc9bf6fc 100644
--- a/synapse/push/emailpusher.py
+++ b/synapse/push/emailpusher.py
@@ -20,12 +20,11 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Dict, List, Optional
+from typing import TYPE_CHECKING
 
 from twisted.internet.error import AlreadyCalled, AlreadyCancelled
 from twisted.internet.interfaces import IDelayedCall
 
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.push import Pusher, PusherConfig, PusherConfigException, ThrottleParams
 from synapse.push.mailer import Mailer
 from synapse.push.push_types import EmailReason
@@ -71,8 +70,8 @@ class EmailPusher(Pusher):
         self.server_name = hs.hostname
         self.store = self.hs.get_datastores().main
         self.email = pusher_config.pushkey
-        self.timed_call: Optional[IDelayedCall] = None
-        self.throttle_params: Dict[str, ThrottleParams] = {}
+        self.timed_call: IDelayedCall | None = None
+        self.throttle_params: dict[str, ThrottleParams] = {}
         self._inited = False
 
         self._is_processing = False
@@ -118,7 +117,7 @@ class EmailPusher(Pusher):
         if self._is_processing:
             return
 
-        run_as_background_process("emailpush.process", self.server_name, self._process)
+        self.hs.run_as_background_process("emailpush.process", self._process)
 
     def _pause_processing(self) -> None:
         """Used by tests to temporarily pause processing of events.
@@ -175,7 +174,7 @@ class EmailPusher(Pusher):
             )
         )
 
-        soonest_due_at: Optional[int] = None
+        soonest_due_at: int | None = None
 
         if not unprocessed:
             await self.save_last_stream_ordering_and_success(self.max_stream_ordering)
@@ -228,8 +227,10 @@ class EmailPusher(Pusher):
                     self.timed_call = None
 
         if soonest_due_at is not None:
-            self.timed_call = self.hs.get_reactor().callLater(
-                self.seconds_until(soonest_due_at), self.on_timer
+            delay = self.seconds_until(soonest_due_at)
+            self.timed_call = self.hs.get_clock().call_later(
+                delay,
+                self.on_timer,
             )
 
     async def save_last_stream_ordering_and_success(
@@ -323,7 +324,7 @@ class EmailPusher(Pusher):
         )
 
     async def send_notification(
-        self, push_actions: List[EmailPushAction], reason: EmailReason
+        self, push_actions: list[EmailPushAction], reason: EmailReason
     ) -> None:
         logger.info("Sending notif email for user %r", self.user_id)
 
diff --git a/synapse/push/httppusher.py b/synapse/push/httppusher.py
index 5946a6e972..edcabf0c29 100644
--- a/synapse/push/httppusher.py
+++ b/synapse/push/httppusher.py
@@ -21,7 +21,7 @@
 import logging
 import random
 import urllib.parse
-from typing import TYPE_CHECKING, Dict, List, Optional, Union
+from typing import TYPE_CHECKING
 
 from prometheus_client import Counter
 
@@ -32,7 +32,6 @@ from synapse.api.constants import EventTypes
 from synapse.events import EventBase
 from synapse.logging import opentracing
 from synapse.metrics import SERVER_NAME_LABEL
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.push import Pusher, PusherConfig, PusherConfigException
 from synapse.storage.databases.main.event_push_actions import HttpPushAction
 from synapse.types import JsonDict, JsonMapping
@@ -69,7 +68,7 @@ http_badges_failed_counter = Counter(
 )
 
 
-def tweaks_for_actions(actions: List[Union[str, Dict]]) -> JsonMapping:
+def tweaks_for_actions(actions: list[str | dict]) -> JsonMapping:
     """
     Converts a list of actions into a `tweaks` dict (which can then be passed to
         the push gateway).
@@ -120,7 +119,7 @@ class HttpPusher(Pusher):
         self.data = pusher_config.data
         self.backoff_delay = HttpPusher.INITIAL_BACKOFF_SEC
         self.failing_since = pusher_config.failing_since
-        self.timed_call: Optional[IDelayedCall] = None
+        self.timed_call: IDelayedCall | None = None
         self._is_processing = False
         self._group_unread_count_by_room = (
             hs.config.push.push_group_unread_count_by_room
@@ -164,7 +163,7 @@ class HttpPusher(Pusher):
         self.data_minus_url = {}
         self.data_minus_url.update(self.data)
         del self.data_minus_url["url"]
-        self.badge_count_last_call: Optional[int] = None
+        self.badge_count_last_call: int | None = None
 
     def on_started(self, should_check_for_notifs: bool) -> None:
         """Called when this pusher has been started.
@@ -182,8 +181,8 @@ class HttpPusher(Pusher):
 
         # We could check the receipts are actually m.read receipts here,
         # but currently that's the only type of receipt anyway...
-        run_as_background_process(
-            "http_pusher.on_new_receipts", self.server_name, self._update_badge
+        self.hs.run_as_background_process(
+            "http_pusher.on_new_receipts", self._update_badge
         )
 
     async def _update_badge(self) -> None:
@@ -219,7 +218,7 @@ class HttpPusher(Pusher):
         if self.failing_since and self.timed_call and self.timed_call.active():
             return
 
-        run_as_background_process("httppush.process", self.server_name, self._process)
+        self.hs.run_as_background_process("httppush.process", self._process)
 
     async def _process(self) -> None:
         # we should never get here if we are already processing
@@ -336,8 +335,9 @@ class HttpPusher(Pusher):
                     )
                 else:
                     logger.info("Push failed: delaying for %ds", self.backoff_delay)
-                    self.timed_call = self.hs.get_reactor().callLater(
-                        self.backoff_delay, self.on_timer
+                    self.timed_call = self.hs.get_clock().call_later(
+                        self.backoff_delay,
+                        self.on_timer,
                     )
                     self.backoff_delay = min(
                         self.backoff_delay * 2, self.MAX_BACKOFF_SEC
@@ -394,9 +394,9 @@ class HttpPusher(Pusher):
     async def dispatch_push(
         self,
         content: JsonDict,
-        tweaks: Optional[JsonMapping] = None,
-        default_payload: Optional[JsonMapping] = None,
-    ) -> Union[bool, List[str]]:
+        tweaks: JsonMapping | None = None,
+        default_payload: JsonMapping | None = None,
+    ) -> bool | list[str]:
         """Send a notification to the registered push gateway, with `content` being
         the content of the `notification` top property specified in the spec.
         Note that the `devices` property will be added with device-specific
@@ -453,7 +453,7 @@ class HttpPusher(Pusher):
         event: EventBase,
         tweaks: JsonMapping,
         badge: int,
-    ) -> Union[bool, List[str]]:
+    ) -> bool | list[str]:
         """Send a notification to the registered push gateway by building it
         from an event.
 
diff --git a/synapse/push/mailer.py b/synapse/push/mailer.py
index d76cc8237b..6492207403 100644
--- a/synapse/push/mailer.py
+++ b/synapse/push/mailer.py
@@ -21,7 +21,7 @@
 
 import logging
 import urllib.parse
-from typing import TYPE_CHECKING, Dict, Iterable, List, Optional, TypeVar
+from typing import TYPE_CHECKING, Iterable, TypeVar
 
 import bleach
 import jinja2
@@ -287,7 +287,7 @@ class Mailer:
 
         notif_events = await self.store.get_events([pa.event_id for pa in push_actions])
 
-        notifs_by_room: Dict[str, List[EmailPushAction]] = {}
+        notifs_by_room: dict[str, list[EmailPushAction]] = {}
         for pa in push_actions:
             notifs_by_room.setdefault(pa.room_id, []).append(pa)
 
@@ -317,7 +317,7 @@ class Mailer:
         # actually sort our so-called rooms_in_order list, most recent room first
         rooms_in_order.sort(key=lambda r: -(notifs_by_room[r][-1].received_ts or 0))
 
-        rooms: List[RoomVars] = []
+        rooms: list[RoomVars] = []
 
         for r in rooms_in_order:
             roomvars = await self._get_room_vars(
@@ -372,7 +372,7 @@ class Mailer:
         email_address: str,
         subject: str,
         extra_template_vars: TemplateVars,
-        unsubscribe_link: Optional[str] = None,
+        unsubscribe_link: str | None = None,
     ) -> None:
         """Send an email with the given information and template text"""
         template_vars: TemplateVars = {
@@ -417,7 +417,7 @@ class Mailer:
         room_id: str,
         user_id: str,
         notifs: Iterable[EmailPushAction],
-        notif_events: Dict[str, EventBase],
+        notif_events: dict[str, EventBase],
         room_state_ids: StateMap[str],
     ) -> RoomVars:
         """
@@ -486,7 +486,7 @@ class Mailer:
     async def _get_room_avatar(
         self,
         room_state_ids: StateMap[str],
-    ) -> Optional[str]:
+    ) -> str | None:
         """
         Retrieve the avatar url for this room---if it exists.
 
@@ -553,7 +553,7 @@ class Mailer:
 
     async def _get_message_vars(
         self, notif: EmailPushAction, event: EventBase, room_state_ids: StateMap[str]
-    ) -> Optional[MessageVars]:
+    ) -> MessageVars | None:
         """
         Generate the variables for a single event, if possible.
 
@@ -573,7 +573,7 @@ class Mailer:
         type_state_key = ("m.room.member", event.sender)
         sender_state_event_id = room_state_ids.get(type_state_key)
         if sender_state_event_id:
-            sender_state_event: Optional[EventBase] = await self.store.get_event(
+            sender_state_event: EventBase | None = await self.store.get_event(
                 sender_state_event_id
             )
         else:
@@ -585,9 +585,7 @@ class Mailer:
 
         if sender_state_event:
             sender_name = name_from_member_event(sender_state_event)
-            sender_avatar_url: Optional[str] = sender_state_event.content.get(
-                "avatar_url"
-            )
+            sender_avatar_url: str | None = sender_state_event.content.get("avatar_url")
         else:
             # No state could be found, fallback to the MXID.
             sender_name = event.sender
@@ -665,9 +663,9 @@ class Mailer:
     async def _make_summary_text_single_room(
         self,
         room_id: str,
-        notifs: List[EmailPushAction],
+        notifs: list[EmailPushAction],
         room_state_ids: StateMap[str],
-        notif_events: Dict[str, EventBase],
+        notif_events: dict[str, EventBase],
         user_id: str,
     ) -> str:
         """
@@ -781,9 +779,9 @@ class Mailer:
 
     async def _make_summary_text(
         self,
-        notifs_by_room: Dict[str, List[EmailPushAction]],
-        room_state_ids: Dict[str, StateMap[str]],
-        notif_events: Dict[str, EventBase],
+        notifs_by_room: dict[str, list[EmailPushAction]],
+        room_state_ids: dict[str, StateMap[str]],
+        notif_events: dict[str, EventBase],
         reason: EmailReason,
     ) -> str:
         """
@@ -814,9 +812,9 @@ class Mailer:
     async def _make_summary_text_from_member_events(
         self,
         room_id: str,
-        notifs: List[EmailPushAction],
+        notifs: list[EmailPushAction],
         room_state_ids: StateMap[str],
-        notif_events: Dict[str, EventBase],
+        notif_events: dict[str, EventBase],
     ) -> str:
         """
         Make a summary text for the email when only a single room has notifications.
@@ -995,7 +993,7 @@ def safe_text(raw_text: str) -> Markup:
     )
 
 
-def deduped_ordered_list(it: Iterable[T]) -> List[T]:
+def deduped_ordered_list(it: Iterable[T]) -> list[T]:
     seen = set()
     ret = []
     for item in it:
diff --git a/synapse/push/presentable_names.py b/synapse/push/presentable_names.py
index 1faa57e9f5..d8000dd607 100644
--- a/synapse/push/presentable_names.py
+++ b/synapse/push/presentable_names.py
@@ -21,7 +21,7 @@
 
 import logging
 import re
-from typing import TYPE_CHECKING, Dict, Iterable, Optional
+from typing import TYPE_CHECKING, Iterable
 
 from synapse.api.constants import EventTypes, Membership
 from synapse.events import EventBase
@@ -45,7 +45,7 @@ async def calculate_room_name(
     user_id: str,
     fallback_to_members: bool = True,
     fallback_to_single_member: bool = True,
-) -> Optional[str]:
+) -> str | None:
     """
     Works out a user-facing name for the given room as per Matrix
     spec recommendations.
@@ -205,8 +205,8 @@ def name_from_member_event(member_event: EventBase) -> str:
     return member_event.state_key
 
 
-def _state_as_two_level_dict(state: StateMap[str]) -> Dict[str, Dict[str, str]]:
-    ret: Dict[str, Dict[str, str]] = {}
+def _state_as_two_level_dict(state: StateMap[str]) -> dict[str, dict[str, str]]:
+    ret: dict[str, dict[str, str]] = {}
     for k, v in state.items():
         ret.setdefault(k[0], {})[k[1]] = v
     return ret
diff --git a/synapse/push/push_tools.py b/synapse/push/push_tools.py
index 3f3e4a9234..8e2ff2bcb4 100644
--- a/synapse/push/push_tools.py
+++ b/synapse/push/push_tools.py
@@ -18,7 +18,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Dict
 
 from synapse.api.constants import EventTypes, Membership
 from synapse.events import EventBase
@@ -56,8 +55,8 @@ async def get_badge_count(store: DataStore, user_id: str, group_by_room: bool) -
 
 async def get_context_for_event(
     storage: StorageControllers, ev: EventBase, user_id: str
-) -> Dict[str, str]:
-    ctx: Dict[str, str] = {}
+) -> dict[str, str]:
+    ctx: dict[str, str] = {}
 
     if ev.internal_metadata.outlier:
         # We don't have state for outliers, so we can't compute the context
diff --git a/synapse/push/push_types.py b/synapse/push/push_types.py
index 57fa926a46..7553b4bf10 100644
--- a/synapse/push/push_types.py
+++ b/synapse/push/push_types.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import List, Optional, TypedDict
+from typing import TypedDict
 
 
 class EmailReason(TypedDict, total=False):
@@ -40,7 +40,7 @@ class EmailReason(TypedDict, total=False):
 
     room_id: str
     now: int
-    room_name: Optional[str]
+    room_name: str | None
     received_at: int
     delay_before_mail_ms: int
     last_sent_ts: int
@@ -71,9 +71,9 @@ class MessageVars(TypedDict, total=False):
     id: str
     ts: int
     sender_name: str
-    sender_avatar_url: Optional[str]
+    sender_avatar_url: str | None
     sender_hash: int
-    msgtype: Optional[str]
+    msgtype: str | None
     body_text_html: str
     body_text_plain: str
     image_url: str
@@ -90,8 +90,8 @@ class NotifVars(TypedDict):
     """
 
     link: str
-    ts: Optional[int]
-    messages: List[MessageVars]
+    ts: int | None
+    messages: list[MessageVars]
 
 
 class RoomVars(TypedDict):
@@ -107,12 +107,12 @@ class RoomVars(TypedDict):
     avator_url: url to the room's avator
     """
 
-    title: Optional[str]
+    title: str | None
     hash: int
     invite: bool
-    notifs: List[NotifVars]
+    notifs: list[NotifVars]
     link: str
-    avatar_url: Optional[str]
+    avatar_url: str | None
 
 
 class TemplateVars(TypedDict, total=False):
@@ -137,5 +137,5 @@ class TemplateVars(TypedDict, total=False):
     user_display_name: str
     unsubscribe_link: str
     summary_text: str
-    rooms: List[RoomVars]
+    rooms: list[RoomVars]
     reason: EmailReason
diff --git a/synapse/push/pusher.py b/synapse/push/pusher.py
index 9a5dd7a9d4..948465cad1 100644
--- a/synapse/push/pusher.py
+++ b/synapse/push/pusher.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Callable, Dict, Optional
+from typing import TYPE_CHECKING, Callable
 
 from synapse.push import Pusher, PusherConfig
 from synapse.push.emailpusher import EmailPusher
@@ -38,13 +38,13 @@ class PusherFactory:
         self.hs = hs
         self.config = hs.config
 
-        self.pusher_types: Dict[str, Callable[[HomeServer, PusherConfig], Pusher]] = {
+        self.pusher_types: dict[str, Callable[[HomeServer, PusherConfig], Pusher]] = {
             "http": HttpPusher
         }
 
         logger.info("email enable notifs: %r", hs.config.email.email_enable_notifs)
         if hs.config.email.email_enable_notifs:
-            self.mailers: Dict[str, Mailer] = {}
+            self.mailers: dict[str, Mailer] = {}
 
             self._notif_template_html = hs.config.email.email_notif_template_html
             self._notif_template_text = hs.config.email.email_notif_template_text
@@ -53,7 +53,7 @@ class PusherFactory:
 
             logger.info("defined email pusher type")
 
-    def create_pusher(self, pusher_config: PusherConfig) -> Optional[Pusher]:
+    def create_pusher(self, pusher_config: PusherConfig) -> Pusher | None:
         kind = pusher_config.kind
         f = self.pusher_types.get(kind, None)
         if not f:
diff --git a/synapse/push/pusherpool.py b/synapse/push/pusherpool.py
index d1f79ec999..7b5b06db83 100644
--- a/synapse/push/pusherpool.py
+++ b/synapse/push/pusherpool.py
@@ -20,14 +20,13 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Dict, Iterable, Optional
+from typing import TYPE_CHECKING, Iterable
 
 from prometheus_client import Gauge
 
 from synapse.api.errors import Codes, SynapseError
 from synapse.metrics import SERVER_NAME_LABEL
 from synapse.metrics.background_process_metrics import (
-    run_as_background_process,
     wrap_as_background_process,
 )
 from synapse.push import Pusher, PusherConfig, PusherConfigException
@@ -70,10 +69,8 @@ class PusherPool:
     """
 
     def __init__(self, hs: "HomeServer"):
-        self.hs = hs
-        self.server_name = (
-            hs.hostname
-        )  # nb must be called this for @wrap_as_background_process
+        self.hs = hs  # nb must be called this for @wrap_as_background_process
+        self.server_name = hs.hostname
         self.pusher_factory = PusherFactory(hs)
         self.store = self.hs.get_datastores().main
         self.clock = self.hs.get_clock()
@@ -103,7 +100,7 @@ class PusherPool:
         self._last_room_stream_id_seen = self.store.get_room_max_stream_ordering()
 
         # map from user id to app_id:pushkey to pusher
-        self.pushers: Dict[str, Dict[str, Pusher]] = {}
+        self.pushers: dict[str, dict[str, Pusher]] = {}
 
         self._account_validity_handler = hs.get_account_validity_handler()
 
@@ -112,9 +109,7 @@ class PusherPool:
         if not self._should_start_pushers:
             logger.info("Not starting pushers because they are disabled in the config")
             return
-        run_as_background_process(
-            "start_pushers", self.server_name, self._start_pushers
-        )
+        self.hs.run_as_background_process("start_pushers", self._start_pushers)
 
     async def add_or_update_pusher(
         self,
@@ -124,12 +119,12 @@ class PusherPool:
         app_display_name: str,
         device_display_name: str,
         pushkey: str,
-        lang: Optional[str],
+        lang: str | None,
         data: JsonDict,
         profile_tag: str = "",
         enabled: bool = True,
-        device_id: Optional[str] = None,
-    ) -> Optional[Pusher]:
+        device_id: str | None = None,
+    ) -> Pusher | None:
         """Creates a new pusher and adds it to the pool
 
         Returns:
@@ -335,7 +330,7 @@ class PusherPool:
 
     async def _get_pusher_config_for_user_by_app_id_and_pushkey(
         self, user_id: str, app_id: str, pushkey: str
-    ) -> Optional[PusherConfig]:
+    ) -> PusherConfig | None:
         resultlist = await self.store.get_pushers_by_app_id_and_pushkey(app_id, pushkey)
 
         pusher_config = None
@@ -347,7 +342,7 @@ class PusherPool:
 
     async def process_pusher_change_by_id(
         self, app_id: str, pushkey: str, user_id: str
-    ) -> Optional[Pusher]:
+    ) -> Pusher | None:
         """Look up the details for the given pusher, and either start it if its
         "enabled" flag is True, or try to stop it otherwise.
 
@@ -386,7 +381,7 @@ class PusherPool:
 
         logger.info("Started pushers")
 
-    async def _start_pusher(self, pusher_config: PusherConfig) -> Optional[Pusher]:
+    async def _start_pusher(self, pusher_config: PusherConfig) -> Pusher | None:
         """Start the given pusher
 
         Args:
diff --git a/synapse/replication/http/_base.py b/synapse/replication/http/_base.py
index 0850a99e0c..d76b40cf39 100644
--- a/synapse/replication/http/_base.py
+++ b/synapse/replication/http/_base.py
@@ -23,7 +23,7 @@ import logging
 import re
 import urllib.parse
 from inspect import signature
-from typing import TYPE_CHECKING, Any, Awaitable, Callable, ClassVar, Dict, List, Tuple
+from typing import TYPE_CHECKING, Any, Awaitable, Callable, ClassVar
 
 from prometheus_client import Counter, Gauge
 
@@ -112,7 +112,7 @@ class ReplicationEndpoint(metaclass=abc.ABCMeta):
     """
 
     NAME: str = abc.abstractproperty()  # type: ignore
-    PATH_ARGS: Tuple[str, ...] = abc.abstractproperty()  # type: ignore
+    PATH_ARGS: tuple[str, ...] = abc.abstractproperty()  # type: ignore
     METHOD = "POST"
     CACHE = True
     RETRY_ON_TIMEOUT = True
@@ -187,7 +187,7 @@ class ReplicationEndpoint(metaclass=abc.ABCMeta):
     @abc.abstractmethod
     async def _handle_request(
         self, request: Request, content: JsonDict, **kwargs: Any
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         """Handle incoming request.
 
         This is called with the request object and PATH_ARGS.
@@ -292,7 +292,7 @@ class ReplicationEndpoint(metaclass=abc.ABCMeta):
                     "/".join(url_args),
                 )
 
-                headers: Dict[bytes, List[bytes]] = {}
+                headers: dict[bytes, list[bytes]] = {}
                 # Add an authorization header, if configured.
                 if replication_secret:
                     headers[b"Authorization"] = [b"Bearer " + replication_secret]
@@ -403,7 +403,7 @@ class ReplicationEndpoint(metaclass=abc.ABCMeta):
 
     async def _check_auth_and_handle(
         self, request: SynapseRequest, **kwargs: Any
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         """Called on new incoming requests when caching is enabled. Checks
         if there is a cached response for the request and returns that,
         otherwise calls `_handle_request` and caches its response.
diff --git a/synapse/replication/http/account_data.py b/synapse/replication/http/account_data.py
index b6eac153ba..560973b916 100644
--- a/synapse/replication/http/account_data.py
+++ b/synapse/replication/http/account_data.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from twisted.web.server import Request
 
@@ -68,7 +68,7 @@ class ReplicationAddUserAccountDataRestServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, user_id: str, account_data_type: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         max_stream_id = await self.handler.add_account_data_for_user(
             user_id, account_data_type, content["content"]
         )
@@ -106,7 +106,7 @@ class ReplicationRemoveUserAccountDataRestServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, user_id: str, account_data_type: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         max_stream_id = await self.handler.remove_account_data_for_user(
             user_id, account_data_type
         )
@@ -153,7 +153,7 @@ class ReplicationAddRoomAccountDataRestServlet(ReplicationEndpoint):
         user_id: str,
         room_id: str,
         account_data_type: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         max_stream_id = await self.handler.add_account_data_to_room(
             user_id, room_id, account_data_type, content["content"]
         )
@@ -196,7 +196,7 @@ class ReplicationRemoveRoomAccountDataRestServlet(ReplicationEndpoint):
         user_id: str,
         room_id: str,
         account_data_type: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         max_stream_id = await self.handler.remove_account_data_for_room(
             user_id, room_id, account_data_type
         )
@@ -238,7 +238,7 @@ class ReplicationAddTagRestServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, user_id: str, room_id: str, tag: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         max_stream_id = await self.handler.add_tag_to_room(
             user_id, room_id, tag, content["content"]
         )
@@ -276,7 +276,7 @@ class ReplicationRemoveTagRestServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, user_id: str, room_id: str, tag: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         max_stream_id = await self.handler.remove_tag_from_room(
             user_id,
             room_id,
diff --git a/synapse/replication/http/deactivate_account.py b/synapse/replication/http/deactivate_account.py
index 89658350a5..82df1e1322 100644
--- a/synapse/replication/http/deactivate_account.py
+++ b/synapse/replication/http/deactivate_account.py
@@ -19,7 +19,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from twisted.web.server import Request
 
@@ -69,7 +69,7 @@ class ReplicationNotifyAccountDeactivatedServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         by_admin = content["by_admin"]
         await self.deactivate_account_handler.notify_account_deactivated(
             user_id, by_admin=by_admin
diff --git a/synapse/replication/http/delayed_events.py b/synapse/replication/http/delayed_events.py
index 229022070c..26eaf68dae 100644
--- a/synapse/replication/http/delayed_events.py
+++ b/synapse/replication/http/delayed_events.py
@@ -13,7 +13,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Dict, Optional, Tuple
+from typing import TYPE_CHECKING
 
 from twisted.web.server import Request
 
@@ -52,7 +52,7 @@ class ReplicationAddedDelayedEventRestServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict
-    ) -> Tuple[int, Dict[str, Optional[JsonMapping]]]:
+    ) -> tuple[int, dict[str, JsonMapping | None]]:
         self.handler.on_added(int(content["next_send_ts"]))
 
         return 200, {}
diff --git a/synapse/replication/http/devices.py b/synapse/replication/http/devices.py
index 94981e22eb..7a11537f9e 100644
--- a/synapse/replication/http/devices.py
+++ b/synapse/replication/http/devices.py
@@ -19,7 +19,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Dict, List, Optional, Tuple
+from typing import TYPE_CHECKING
 
 from twisted.web.server import Request
 
@@ -59,13 +59,13 @@ class ReplicationNotifyDeviceUpdateRestServlet(ReplicationEndpoint):
 
     @staticmethod
     async def _serialize_payload(  # type: ignore[override]
-        user_id: str, device_ids: List[str]
+        user_id: str, device_ids: list[str]
     ) -> JsonDict:
         return {"device_ids": device_ids}
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         device_ids = content["device_ids"]
 
         span = active_span()
@@ -102,12 +102,12 @@ class ReplicationNotifyUserSignatureUpdateRestServlet(ReplicationEndpoint):
         self.clock = hs.get_clock()
 
     @staticmethod
-    async def _serialize_payload(from_user_id: str, user_ids: List[str]) -> JsonDict:  # type: ignore[override]
+    async def _serialize_payload(from_user_id: str, user_ids: list[str]) -> JsonDict:  # type: ignore[override]
         return {"user_ids": user_ids}
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, from_user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         user_ids = content["user_ids"]
 
         span = active_span()
@@ -165,13 +165,13 @@ class ReplicationMultiUserDevicesResyncRestServlet(ReplicationEndpoint):
         self.clock = hs.get_clock()
 
     @staticmethod
-    async def _serialize_payload(user_ids: List[str]) -> JsonDict:  # type: ignore[override]
+    async def _serialize_payload(user_ids: list[str]) -> JsonDict:  # type: ignore[override]
         return {"user_ids": user_ids}
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict
-    ) -> Tuple[int, Dict[str, Optional[JsonMapping]]]:
-        user_ids: List[str] = content["user_ids"]
+    ) -> tuple[int, dict[str, JsonMapping | None]]:
+        user_ids: list[str] = content["user_ids"]
 
         logger.info("Resync for %r", user_ids)
         span = active_span()
@@ -210,7 +210,7 @@ class ReplicationHandleNewDeviceUpdateRestServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await self.device_handler.handle_new_device_update()
         return 200, {}
 
@@ -241,7 +241,7 @@ class ReplicationDeviceHandleRoomUnPartialStated(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await self.device_handler.handle_room_un_partial_stated(room_id)
         return 200, {}
 
diff --git a/synapse/replication/http/federation.py b/synapse/replication/http/federation.py
index 1e302ef59f..448a1f8a71 100644
--- a/synapse/replication/http/federation.py
+++ b/synapse/replication/http/federation.py
@@ -19,7 +19,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, List, Tuple
+from typing import TYPE_CHECKING
 
 from twisted.web.server import Request
 
@@ -86,7 +86,7 @@ class ReplicationFederationSendEventsRestServlet(ReplicationEndpoint):
     async def _serialize_payload(  # type: ignore[override]
         store: "DataStore",
         room_id: str,
-        event_and_contexts: List[EventPersistencePair],
+        event_and_contexts: list[EventPersistencePair],
         backfilled: bool,
     ) -> JsonDict:
         """
@@ -122,7 +122,7 @@ class ReplicationFederationSendEventsRestServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         with Measure(
             self.clock, name="repl_fed_send_events_parse", server_name=self.server_name
         ):
@@ -194,7 +194,7 @@ class ReplicationFederationSendEduRestServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, edu_type: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         origin = content["origin"]
         edu_content = content["content"]
 
@@ -243,7 +243,7 @@ class ReplicationGetQueryRestServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, query_type: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         args = content["args"]
         args["origin"] = content["origin"]
 
@@ -285,7 +285,7 @@ class ReplicationCleanRoomRestServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await self.store.clean_room_for_join(room_id)
 
         return 200, {}
@@ -320,7 +320,7 @@ class ReplicationStoreRoomOnOutlierMembershipRestServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         room_version = KNOWN_ROOM_VERSIONS[content["room_version"]]
         await self.store.maybe_store_room_on_outlier_membership(room_id, room_version)
         return 200, {}
diff --git a/synapse/replication/http/login.py b/synapse/replication/http/login.py
index 8b5b7f755a..fc21c20ca2 100644
--- a/synapse/replication/http/login.py
+++ b/synapse/replication/http/login.py
@@ -19,7 +19,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Optional, Tuple, cast
+from typing import TYPE_CHECKING, cast
 
 from twisted.web.server import Request
 
@@ -50,13 +50,13 @@ class RegisterDeviceReplicationServlet(ReplicationEndpoint):
     @staticmethod
     async def _serialize_payload(  # type: ignore[override]
         user_id: str,
-        device_id: Optional[str],
-        initial_display_name: Optional[str],
+        device_id: str | None,
+        initial_display_name: str | None,
         is_guest: bool,
         is_appservice_ghost: bool,
         should_issue_refresh_token: bool,
-        auth_provider_id: Optional[str],
-        auth_provider_session_id: Optional[str],
+        auth_provider_id: str | None,
+        auth_provider_session_id: str | None,
     ) -> JsonDict:
         """
         Args:
@@ -79,7 +79,7 @@ class RegisterDeviceReplicationServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         device_id = content["device_id"]
         initial_display_name = content["initial_display_name"]
         is_guest = content["is_guest"]
diff --git a/synapse/replication/http/membership.py b/synapse/replication/http/membership.py
index fc66039b2f..8a6c971720 100644
--- a/synapse/replication/http/membership.py
+++ b/synapse/replication/http/membership.py
@@ -18,7 +18,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, List, Optional, Tuple
+from typing import TYPE_CHECKING
 
 from twisted.web.server import Request
 
@@ -63,7 +63,7 @@ class ReplicationRemoteJoinRestServlet(ReplicationEndpoint):
         requester: Requester,
         room_id: str,
         user_id: str,
-        remote_room_hosts: List[str],
+        remote_room_hosts: list[str],
         content: JsonDict,
     ) -> JsonDict:
         """
@@ -85,7 +85,7 @@ class ReplicationRemoteJoinRestServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: SynapseRequest, content: JsonDict, room_id: str, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         remote_room_hosts = content["remote_room_hosts"]
         event_content = content["content"]
 
@@ -130,7 +130,7 @@ class ReplicationRemoteKnockRestServlet(ReplicationEndpoint):
         requester: Requester,
         room_id: str,
         user_id: str,
-        remote_room_hosts: List[str],
+        remote_room_hosts: list[str],
         content: JsonDict,
     ) -> JsonDict:
         """
@@ -149,7 +149,7 @@ class ReplicationRemoteKnockRestServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: SynapseRequest, content: JsonDict, room_id: str, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         remote_room_hosts = content["remote_room_hosts"]
         event_content = content["content"]
 
@@ -192,7 +192,7 @@ class ReplicationRemoteRejectInviteRestServlet(ReplicationEndpoint):
     @staticmethod
     async def _serialize_payload(  # type: ignore[override]
         invite_event_id: str,
-        txn_id: Optional[str],
+        txn_id: str | None,
         requester: Requester,
         content: JsonDict,
     ) -> JsonDict:
@@ -215,7 +215,7 @@ class ReplicationRemoteRejectInviteRestServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: SynapseRequest, content: JsonDict, invite_event_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         txn_id = content["txn_id"]
         event_content = content["content"]
 
@@ -260,7 +260,7 @@ class ReplicationRemoteRescindKnockRestServlet(ReplicationEndpoint):
     @staticmethod
     async def _serialize_payload(  # type: ignore[override]
         knock_event_id: str,
-        txn_id: Optional[str],
+        txn_id: str | None,
         requester: Requester,
         content: JsonDict,
     ) -> JsonDict:
@@ -279,7 +279,7 @@ class ReplicationRemoteRescindKnockRestServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: SynapseRequest, content: JsonDict, knock_event_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         txn_id = content["txn_id"]
         event_content = content["content"]
 
@@ -343,7 +343,7 @@ class ReplicationUserJoinedLeftRoomRestServlet(ReplicationEndpoint):
         room_id: str,
         user_id: str,
         change: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         logger.info("user membership change: %s in %s", user_id, room_id)
 
         user = UserID.from_string(user_id)
diff --git a/synapse/replication/http/presence.py b/synapse/replication/http/presence.py
index 8a3f3b0e67..960f0485ff 100644
--- a/synapse/replication/http/presence.py
+++ b/synapse/replication/http/presence.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Optional, Tuple
+from typing import TYPE_CHECKING
 
 from twisted.web.server import Request
 
@@ -58,12 +58,12 @@ class ReplicationBumpPresenceActiveTime(ReplicationEndpoint):
         self._presence_handler = hs.get_presence_handler()
 
     @staticmethod
-    async def _serialize_payload(user_id: str, device_id: Optional[str]) -> JsonDict:  # type: ignore[override]
+    async def _serialize_payload(user_id: str, device_id: str | None) -> JsonDict:  # type: ignore[override]
         return {"device_id": device_id}
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await self._presence_handler.bump_presence_active_time(
             UserID.from_string(user_id), content.get("device_id")
         )
@@ -102,7 +102,7 @@ class ReplicationPresenceSetState(ReplicationEndpoint):
     @staticmethod
     async def _serialize_payload(  # type: ignore[override]
         user_id: str,
-        device_id: Optional[str],
+        device_id: str | None,
         state: JsonDict,
         force_notify: bool = False,
         is_sync: bool = False,
@@ -116,7 +116,7 @@ class ReplicationPresenceSetState(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await self._presence_handler.set_state(
             UserID.from_string(user_id),
             content.get("device_id"),
diff --git a/synapse/replication/http/push.py b/synapse/replication/http/push.py
index 6e20a208b6..905414b5ee 100644
--- a/synapse/replication/http/push.py
+++ b/synapse/replication/http/push.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from twisted.web.server import Request
 
@@ -68,7 +68,7 @@ class ReplicationRemovePusherRestServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         app_id = content["app_id"]
         pushkey = content["pushkey"]
 
@@ -110,7 +110,7 @@ class ReplicationCopyPusherRestServlet(ReplicationEndpoint):
         user_id: str,
         old_room_id: str,
         new_room_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await self._store.copy_push_rules_from_room_to_room_for_user(
             old_room_id, new_room_id, user_id
         )
@@ -144,7 +144,7 @@ class ReplicationDeleteAllPushersForUserRestServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await self._store.delete_all_pushers_for_user(user_id)
 
         return 200, {}
diff --git a/synapse/replication/http/register.py b/synapse/replication/http/register.py
index 27d3504c3c..bd83b38c96 100644
--- a/synapse/replication/http/register.py
+++ b/synapse/replication/http/register.py
@@ -19,7 +19,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Optional, Tuple
+from typing import TYPE_CHECKING
 
 from twisted.web.server import Request
 
@@ -59,14 +59,14 @@ class ReplicationRegisterServlet(ReplicationEndpoint):
     @staticmethod
     async def _serialize_payload(  # type: ignore[override]
         user_id: str,
-        password_hash: Optional[str],
+        password_hash: str | None,
         was_guest: bool,
         make_guest: bool,
-        appservice_id: Optional[str],
-        create_profile_with_displayname: Optional[str],
+        appservice_id: str | None,
+        create_profile_with_displayname: str | None,
         admin: bool,
-        user_type: Optional[str],
-        address: Optional[str],
+        user_type: str | None,
+        address: str | None,
         shadow_banned: bool,
         approved: bool,
     ) -> JsonDict:
@@ -104,7 +104,7 @@ class ReplicationRegisterServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await self.registration_handler.check_registration_ratelimit(content["address"])
 
         # Always default admin users to approved (since it means they were created by
@@ -143,7 +143,7 @@ class ReplicationPostRegisterActionsServlet(ReplicationEndpoint):
 
     @staticmethod
     async def _serialize_payload(  # type: ignore[override]
-        user_id: str, auth_result: JsonDict, access_token: Optional[str]
+        user_id: str, auth_result: JsonDict, access_token: str | None
     ) -> JsonDict:
         """
         Args:
@@ -156,7 +156,7 @@ class ReplicationPostRegisterActionsServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         auth_result = content["auth_result"]
         access_token = content["access_token"]
 
diff --git a/synapse/replication/http/send_events.py b/synapse/replication/http/send_events.py
index 6b1a5a9956..b020a0fe7c 100644
--- a/synapse/replication/http/send_events.py
+++ b/synapse/replication/http/send_events.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, List, Tuple
+from typing import TYPE_CHECKING
 
 from twisted.web.server import Request
 
@@ -85,11 +85,11 @@ class ReplicationSendEventsRestServlet(ReplicationEndpoint):
 
     @staticmethod
     async def _serialize_payload(  # type: ignore[override]
-        events_and_context: List[EventPersistencePair],
+        events_and_context: list[EventPersistencePair],
         store: "DataStore",
         requester: Requester,
         ratelimit: bool,
-        extra_users: List[UserID],
+        extra_users: list[UserID],
     ) -> JsonDict:
         """
         Args:
@@ -122,7 +122,7 @@ class ReplicationSendEventsRestServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, payload: JsonDict
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         with Measure(
             self.clock, name="repl_send_events_parse", server_name=self.server_name
         ):
diff --git a/synapse/replication/http/state.py b/synapse/replication/http/state.py
index 3ec4ca5de3..823d330041 100644
--- a/synapse/replication/http/state.py
+++ b/synapse/replication/http/state.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from twisted.web.server import Request
 
@@ -65,7 +65,7 @@ class ReplicationUpdateCurrentStateRestServlet(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         writer_instance = self._events_shard_config.get_instance(room_id)
         if writer_instance != self._instance_name:
             raise SynapseError(
diff --git a/synapse/replication/http/streams.py b/synapse/replication/http/streams.py
index 61f70d5790..42e78c976f 100644
--- a/synapse/replication/http/streams.py
+++ b/synapse/replication/http/streams.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from twisted.web.server import Request
 
@@ -79,7 +79,7 @@ class ReplicationGetStreamUpdates(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict, stream_name: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         stream = self.streams.get(stream_name)
         if stream is None:
             raise SynapseError(400, "Unknown stream")
diff --git a/synapse/replication/tcp/client.py b/synapse/replication/tcp/client.py
index d96f5541f1..297feb0049 100644
--- a/synapse/replication/tcp/client.py
+++ b/synapse/replication/tcp/client.py
@@ -21,7 +21,7 @@
 """A replication client for use by synapse workers."""
 
 import logging
-from typing import TYPE_CHECKING, Dict, Iterable, Optional, Set, Tuple
+from typing import TYPE_CHECKING, Iterable
 
 from sortedcontainers import SortedList
 
@@ -32,7 +32,6 @@ from synapse.api.constants import EventTypes, Membership, ReceiptTypes
 from synapse.federation import send_queue
 from synapse.federation.sender import FederationSender
 from synapse.logging.context import PreserveLoggingContext, make_deferred_yieldable
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.replication.tcp.streams import (
     AccountDataStream,
     DeviceListsStream,
@@ -90,14 +89,14 @@ class ReplicationDataHandler:
         self._pusher_pool = hs.get_pusherpool()
         self._presence_handler = hs.get_presence_handler()
 
-        self.send_handler: Optional[FederationSenderHandler] = None
+        self.send_handler: FederationSenderHandler | None = None
         if hs.should_send_federation():
             self.send_handler = FederationSenderHandler(hs)
 
         # Map from stream and instance to list of deferreds waiting for the stream to
         # arrive at a particular position. The lists are sorted by stream position.
-        self._streams_to_waiters: Dict[
-            Tuple[str, str], SortedList[Tuple[int, Deferred]]
+        self._streams_to_waiters: dict[
+            tuple[str, str], SortedList[tuple[int, Deferred]]
         ] = {}
 
     async def on_rdata(
@@ -114,7 +113,7 @@ class ReplicationDataHandler:
             token: stream token for this batch of rows
             rows: a list of Stream.ROW_TYPE objects as returned by Stream.parse_row.
         """
-        all_room_ids: Set[str] = set()
+        all_room_ids: set[str] = set()
         if stream_name == DeviceListsStream.NAME:
             if any(not row.is_signature and not row.hosts_calculated for row in rows):
                 # This only uses the minimum stream position on the device lists
@@ -201,7 +200,7 @@ class ReplicationDataHandler:
                 if row.data.rejected:
                     continue
 
-                extra_users: Tuple[UserID, ...] = ()
+                extra_users: tuple[UserID, ...] = ()
                 if row.data.type == EventTypes.Member and row.data.state_key:
                     extra_users = (UserID.from_string(row.data.state_key),)
 
@@ -344,7 +343,9 @@ class ReplicationDataHandler:
         # to wedge here forever.
         deferred: "Deferred[None]" = Deferred()
         deferred = timeout_deferred(
-            deferred, _WAIT_FOR_REPLICATION_TIMEOUT_SECONDS, self._reactor
+            deferred=deferred,
+            timeout=_WAIT_FOR_REPLICATION_TIMEOUT_SECONDS,
+            clock=self._clock,
         )
 
         waiting_list = self._streams_to_waiters.setdefault(
@@ -434,7 +435,7 @@ class FederationSenderHandler:
 
         # Stores the latest position in the federation stream we've gotten up
         # to. This is always set before we use it.
-        self.federation_position: Optional[int] = None
+        self.federation_position: int | None = None
 
         self._fed_position_linearizer = Linearizer(
             name="_fed_position_linearizer", clock=hs.get_clock()
@@ -513,8 +514,8 @@ class FederationSenderHandler:
             # no need to queue up another task.
             return
 
-        run_as_background_process(
-            "_save_and_send_ack", self.server_name, self._save_and_send_ack
+        self._hs.run_as_background_process(
+            "_save_and_send_ack", self._save_and_send_ack
         )
 
     async def _save_and_send_ack(self) -> None:
diff --git a/synapse/replication/tcp/commands.py b/synapse/replication/tcp/commands.py
index 8eec68c3dd..79194f7275 100644
--- a/synapse/replication/tcp/commands.py
+++ b/synapse/replication/tcp/commands.py
@@ -26,7 +26,7 @@ allowed to be sent by which side.
 
 import abc
 import logging
-from typing import List, Optional, Tuple, Type, TypeVar
+from typing import TypeVar
 
 from synapse.replication.tcp.streams._base import StreamRow
 from synapse.util.json import json_decoder, json_encoder
@@ -49,7 +49,7 @@ class Command(metaclass=abc.ABCMeta):
 
     @classmethod
     @abc.abstractmethod
-    def from_line(cls: Type[T], line: str) -> T:
+    def from_line(cls: type[T], line: str) -> T:
         """Deserialises a line from the wire into this command. `line` does not
         include the command.
         """
@@ -88,7 +88,7 @@ class _SimpleCommand(Command):
         self.data = data
 
     @classmethod
-    def from_line(cls: Type[SC], line: str) -> SC:
+    def from_line(cls: type[SC], line: str) -> SC:
         return cls(line)
 
     def to_line(self) -> str:
@@ -137,7 +137,7 @@ class RdataCommand(Command):
     NAME = "RDATA"
 
     def __init__(
-        self, stream_name: str, instance_name: str, token: Optional[int], row: StreamRow
+        self, stream_name: str, instance_name: str, token: int | None, row: StreamRow
     ):
         self.stream_name = stream_name
         self.instance_name = instance_name
@@ -145,7 +145,7 @@ class RdataCommand(Command):
         self.row = row
 
     @classmethod
-    def from_line(cls: Type["RdataCommand"], line: str) -> "RdataCommand":
+    def from_line(cls: type["RdataCommand"], line: str) -> "RdataCommand":
         stream_name, instance_name, token, row_json = line.split(" ", 3)
         return cls(
             stream_name,
@@ -204,7 +204,7 @@ class PositionCommand(Command):
         self.new_token = new_token
 
     @classmethod
-    def from_line(cls: Type["PositionCommand"], line: str) -> "PositionCommand":
+    def from_line(cls: type["PositionCommand"], line: str) -> "PositionCommand":
         stream_name, instance_name, prev_token, new_token = line.split(" ", 3)
         return cls(stream_name, instance_name, int(prev_token), int(new_token))
 
@@ -249,7 +249,7 @@ class ReplicateCommand(Command):
         REPLICATE
     """
 
-    __slots__: List[str] = []
+    __slots__: list[str] = []
 
     NAME = "REPLICATE"
 
@@ -257,7 +257,7 @@ class ReplicateCommand(Command):
         pass
 
     @classmethod
-    def from_line(cls: Type[T], line: str) -> T:
+    def from_line(cls: type[T], line: str) -> T:
         return cls()
 
     def to_line(self) -> str:
@@ -288,7 +288,7 @@ class UserSyncCommand(Command):
         self,
         instance_id: str,
         user_id: str,
-        device_id: Optional[str],
+        device_id: str | None,
         is_syncing: bool,
         last_sync_ms: int,
     ):
@@ -299,8 +299,8 @@ class UserSyncCommand(Command):
         self.last_sync_ms = last_sync_ms
 
     @classmethod
-    def from_line(cls: Type["UserSyncCommand"], line: str) -> "UserSyncCommand":
-        device_id: Optional[str]
+    def from_line(cls: type["UserSyncCommand"], line: str) -> "UserSyncCommand":
+        device_id: str | None
         instance_id, user_id, device_id, state, last_sync_ms = line.split(" ", 4)
 
         if device_id == "None":
@@ -343,7 +343,7 @@ class ClearUserSyncsCommand(Command):
 
     @classmethod
     def from_line(
-        cls: Type["ClearUserSyncsCommand"], line: str
+        cls: type["ClearUserSyncsCommand"], line: str
     ) -> "ClearUserSyncsCommand":
         return cls(line)
 
@@ -373,7 +373,7 @@ class FederationAckCommand(Command):
 
     @classmethod
     def from_line(
-        cls: Type["FederationAckCommand"], line: str
+        cls: type["FederationAckCommand"], line: str
     ) -> "FederationAckCommand":
         instance_name, token = line.split(" ")
         return cls(instance_name, int(token))
@@ -407,7 +407,7 @@ class UserIpCommand(Command):
         access_token: str,
         ip: str,
         user_agent: str,
-        device_id: Optional[str],
+        device_id: str | None,
         last_seen: int,
     ):
         self.user_id = user_id
@@ -418,7 +418,7 @@ class UserIpCommand(Command):
         self.last_seen = last_seen
 
     @classmethod
-    def from_line(cls: Type["UserIpCommand"], line: str) -> "UserIpCommand":
+    def from_line(cls: type["UserIpCommand"], line: str) -> "UserIpCommand":
         user_id, jsn = line.split(" ", 1)
 
         access_token, ip, user_agent, device_id, last_seen = json_decoder.decode(jsn)
@@ -485,7 +485,7 @@ class LockReleasedCommand(Command):
         self.lock_key = lock_key
 
     @classmethod
-    def from_line(cls: Type["LockReleasedCommand"], line: str) -> "LockReleasedCommand":
+    def from_line(cls: type["LockReleasedCommand"], line: str) -> "LockReleasedCommand":
         instance_name, lock_name, lock_key = json_decoder.decode(line)
 
         return cls(instance_name, lock_name, lock_key)
@@ -505,7 +505,7 @@ class NewActiveTaskCommand(_SimpleCommand):
     NAME = "NEW_ACTIVE_TASK"
 
 
-_COMMANDS: Tuple[Type[Command], ...] = (
+_COMMANDS: tuple[type[Command], ...] = (
     ServerCommand,
     RdataCommand,
     PositionCommand,
diff --git a/synapse/replication/tcp/external_cache.py b/synapse/replication/tcp/external_cache.py
index bcdd55d2e6..ca959a7aae 100644
--- a/synapse/replication/tcp/external_cache.py
+++ b/synapse/replication/tcp/external_cache.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Any, Optional
+from typing import TYPE_CHECKING, Any
 
 from prometheus_client import Counter, Histogram
 
@@ -73,7 +73,7 @@ class ExternalCache:
         self.server_name = hs.hostname
 
         if hs.config.redis.redis_enabled:
-            self._redis_connection: Optional["ConnectionHandler"] = (
+            self._redis_connection: "ConnectionHandler" | None = (
                 hs.get_outbound_redis_connection()
             )
         else:
@@ -121,7 +121,7 @@ class ExternalCache:
                     )
                 )
 
-    async def get(self, cache_name: str, key: str) -> Optional[Any]:
+    async def get(self, cache_name: str, key: str) -> Any | None:
         """Look up a key/value in the named cache."""
 
         if self._redis_connection is None:
diff --git a/synapse/replication/tcp/handler.py b/synapse/replication/tcp/handler.py
index dd7e38dd78..05370045e6 100644
--- a/synapse/replication/tcp/handler.py
+++ b/synapse/replication/tcp/handler.py
@@ -24,16 +24,9 @@ from typing import (
     TYPE_CHECKING,
     Any,
     Awaitable,
-    Deque,
-    Dict,
     Iterable,
     Iterator,
-    List,
-    Optional,
-    Set,
-    Tuple,
     TypeVar,
-    Union,
 )
 
 from prometheus_client import Counter
@@ -41,7 +34,6 @@ from prometheus_client import Counter
 from twisted.internet.protocol import ReconnectingClientFactory
 
 from synapse.metrics import SERVER_NAME_LABEL, LaterGauge
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.replication.tcp.commands import (
     ClearUserSyncsCommand,
     Command,
@@ -76,6 +68,7 @@ from synapse.replication.tcp.streams._base import (
     DeviceListsStream,
     ThreadSubscriptionsStream,
 )
+from synapse.util.background_queue import BackgroundQueue
 
 if TYPE_CHECKING:
     from synapse.server import HomeServer
@@ -120,9 +113,7 @@ tcp_command_queue_gauge = LaterGauge(
 
 
 # the type of the entries in _command_queues_by_stream
-_StreamCommandQueue = Deque[
-    Tuple[Union[RdataCommand, PositionCommand], IReplicationConnection]
-]
+_StreamCommandQueueItem = tuple[RdataCommand | PositionCommand, IReplicationConnection]
 
 
 class ReplicationCommandHandler:
@@ -132,6 +123,7 @@ class ReplicationCommandHandler:
 
     def __init__(self, hs: "HomeServer"):
         self.server_name = hs.hostname
+        self.hs = hs
         self._replication_data_handler = hs.get_replication_data_handler()
         self._presence_handler = hs.get_presence_handler()
         self._store = hs.get_datastores().main
@@ -141,18 +133,18 @@ class ReplicationCommandHandler:
         self._instance_name = hs.get_instance_name()
 
         # Additional Redis channel suffixes to subscribe to.
-        self._channels_to_subscribe_to: List[str] = []
+        self._channels_to_subscribe_to: list[str] = []
 
         self._is_presence_writer = (
             hs.get_instance_name() in hs.config.worker.writers.presence
         )
 
-        self._streams: Dict[str, Stream] = {
+        self._streams: dict[str, Stream] = {
             stream.NAME: stream(hs) for stream in STREAMS_MAP.values()
         }
 
         # List of streams that this instance is the source of
-        self._streams_to_replicate: List[Stream] = []
+        self._streams_to_replicate: list[Stream] = []
 
         for stream in self._streams.values():
             if hs.config.redis.redis_enabled and stream.NAME == CachesStream.NAME:
@@ -246,14 +238,14 @@ class ReplicationCommandHandler:
 
         # Map of stream name to batched updates. See RdataCommand for info on
         # how batching works.
-        self._pending_batches: Dict[str, List[Any]] = {}
+        self._pending_batches: dict[str, list[Any]] = {}
 
         # The factory used to create connections.
-        self._factory: Optional[ReconnectingClientFactory] = None
+        self._factory: ReconnectingClientFactory | None = None
 
         # The currently connected connections. (The list of places we need to send
         # outgoing replication commands to.)
-        self._connections: List[IReplicationConnection] = []
+        self._connections: list[IReplicationConnection] = []
 
         tcp_resource_total_connections_gauge.register_hook(
             homeserver_instance_id=hs.get_instance_id(),
@@ -264,17 +256,22 @@ class ReplicationCommandHandler:
         # them in order in a separate background process.
 
         # the streams which are currently being processed by _unsafe_process_queue
-        self._processing_streams: Set[str] = set()
+        self._processing_streams: set[str] = set()
 
         # for each stream, a queue of commands that are awaiting processing, and the
         # connection that they arrived on.
         self._command_queues_by_stream = {
-            stream_name: _StreamCommandQueue() for stream_name in self._streams
+            stream_name: BackgroundQueue[_StreamCommandQueueItem](
+                hs,
+                "process-replication-data",
+                self._unsafe_process_item,
+            )
+            for stream_name in self._streams
         }
 
         # For each connection, the incoming stream names that have received a POSITION
         # from that connection.
-        self._streams_by_connection: Dict[IReplicationConnection, Set[str]] = {}
+        self._streams_by_connection: dict[IReplicationConnection, set[str]] = {}
 
         tcp_command_queue_gauge.register_hook(
             homeserver_instance_id=hs.get_instance_id(),
@@ -340,7 +337,7 @@ class ReplicationCommandHandler:
             self._channels_to_subscribe_to.append(channel_name)
 
     def _add_command_to_stream_queue(
-        self, conn: IReplicationConnection, cmd: Union[RdataCommand, PositionCommand]
+        self, conn: IReplicationConnection, cmd: RdataCommand | PositionCommand
     ) -> None:
         """Queue the given received command for processing
 
@@ -353,43 +350,21 @@ class ReplicationCommandHandler:
             logger.error("Got %s for unknown stream: %s", cmd.NAME, stream_name)
             return
 
-        queue.append((cmd, conn))
+        queue.add((cmd, conn))
 
-        # if we're already processing this stream, there's nothing more to do:
-        # the new entry on the queue will get picked up in due course
-        if stream_name in self._processing_streams:
-            return
+    async def _unsafe_process_item(self, item: _StreamCommandQueueItem) -> None:
+        """Process a single command from the stream queue.
 
-        # fire off a background process to start processing the queue.
-        run_as_background_process(
-            "process-replication-data",
-            self.server_name,
-            self._unsafe_process_queue,
-            stream_name,
-        )
-
-    async def _unsafe_process_queue(self, stream_name: str) -> None:
-        """Processes the command queue for the given stream, until it is empty
-
-        Does not check if there is already a thread processing the queue, hence "unsafe"
+        This should only be called one at a time per stream, and is called from
+        the stream's BackgroundQueue.
         """
-        assert stream_name not in self._processing_streams
-
-        self._processing_streams.add(stream_name)
-        try:
-            queue = self._command_queues_by_stream.get(stream_name)
-            while queue:
-                cmd, conn = queue.popleft()
-                try:
-                    await self._process_command(cmd, conn, stream_name)
-                except Exception:
-                    logger.exception("Failed to handle command %s", cmd)
-        finally:
-            self._processing_streams.discard(stream_name)
+        cmd, conn = item
+        stream_name = cmd.stream_name
+        await self._process_command(cmd, conn, stream_name)
 
     async def _process_command(
         self,
-        cmd: Union[PositionCommand, RdataCommand],
+        cmd: PositionCommand | RdataCommand,
         conn: IReplicationConnection,
         stream_name: str,
     ) -> None:
@@ -451,11 +426,11 @@ class ReplicationCommandHandler:
                 bindAddress=None,
             )
 
-    def get_streams(self) -> Dict[str, Stream]:
+    def get_streams(self) -> dict[str, Stream]:
         """Get a map from stream name to all streams."""
         return self._streams
 
-    def get_streams_to_replicate(self) -> List[Stream]:
+    def get_streams_to_replicate(self) -> list[Stream]:
         """Get a list of streams that this instances replicates."""
         return self._streams_to_replicate
 
@@ -480,7 +455,7 @@ class ReplicationCommandHandler:
 
     def on_USER_SYNC(
         self, conn: IReplicationConnection, cmd: UserSyncCommand
-    ) -> Optional[Awaitable[None]]:
+    ) -> Awaitable[None] | None:
         user_sync_counter.labels(**{SERVER_NAME_LABEL: self.server_name}).inc()
 
         if self._is_presence_writer:
@@ -496,7 +471,7 @@ class ReplicationCommandHandler:
 
     def on_CLEAR_USER_SYNC(
         self, conn: IReplicationConnection, cmd: ClearUserSyncsCommand
-    ) -> Optional[Awaitable[None]]:
+    ) -> Awaitable[None] | None:
         if self._is_presence_writer:
             return self._presence_handler.update_external_syncs_clear(cmd.instance_id)
         else:
@@ -512,7 +487,7 @@ class ReplicationCommandHandler:
 
     def on_USER_IP(
         self, conn: IReplicationConnection, cmd: UserIpCommand
-    ) -> Optional[Awaitable[None]]:
+    ) -> Awaitable[None] | None:
         user_ip_cache_counter.labels(**{SERVER_NAME_LABEL: self.server_name}).inc()
 
         if self._is_master or self._should_insert_client_ips:
@@ -854,7 +829,7 @@ class ReplicationCommandHandler:
         self,
         instance_id: str,
         user_id: str,
-        device_id: Optional[str],
+        device_id: str | None,
         is_syncing: bool,
         last_sync_ms: int,
     ) -> None:
@@ -869,7 +844,7 @@ class ReplicationCommandHandler:
         access_token: str,
         ip: str,
         user_agent: str,
-        device_id: Optional[str],
+        device_id: str | None,
         last_seen: int,
     ) -> None:
         """Tell the master that the user made a request."""
@@ -879,7 +854,7 @@ class ReplicationCommandHandler:
     def send_remote_server_up(self, server: str) -> None:
         self.send_command(RemoteServerUpCommand(server))
 
-    def stream_update(self, stream_name: str, token: Optional[int], data: Any) -> None:
+    def stream_update(self, stream_name: str, token: int | None, data: Any) -> None:
         """Called when a new update is available to stream to Redis subscribers.
 
         We need to check if the client is interested in the stream or not
@@ -903,8 +878,8 @@ UpdateRow = TypeVar("UpdateRow")
 
 
 def _batch_updates(
-    updates: Iterable[Tuple[UpdateToken, UpdateRow]],
-) -> Iterator[Tuple[UpdateToken, List[UpdateRow]]]:
+    updates: Iterable[tuple[UpdateToken, UpdateRow]],
+) -> Iterator[tuple[UpdateToken, list[UpdateRow]]]:
     """Collect stream updates with the same token together
 
     Given a series of updates returned by Stream.get_updates_since(), collects
diff --git a/synapse/replication/tcp/protocol.py b/synapse/replication/tcp/protocol.py
index 25a7868cd7..3068e60af0 100644
--- a/synapse/replication/tcp/protocol.py
+++ b/synapse/replication/tcp/protocol.py
@@ -28,7 +28,7 @@ import fcntl
 import logging
 import struct
 from inspect import isawaitable
-from typing import TYPE_CHECKING, Any, Collection, List, Optional
+from typing import TYPE_CHECKING, Any, Collection
 
 from prometheus_client import Counter
 from zope.interface import Interface, implementer
@@ -42,7 +42,6 @@ from synapse.logging.context import PreserveLoggingContext
 from synapse.metrics import SERVER_NAME_LABEL, LaterGauge
 from synapse.metrics.background_process_metrics import (
     BackgroundProcessLoggingContext,
-    run_as_background_process,
 )
 from synapse.replication.tcp.commands import (
     VALID_CLIENT_COMMANDS,
@@ -83,7 +82,7 @@ tcp_outbound_commands_counter = Counter(
 
 # A list of all connected protocols. This allows us to send metrics about the
 # connections.
-connected_connections: "List[BaseReplicationStreamProtocol]" = []
+connected_connections: "list[BaseReplicationStreamProtocol]" = []
 
 
 logger = logging.getLogger(__name__)
@@ -140,16 +139,21 @@ class BaseReplicationStreamProtocol(LineOnlyReceiver):
     max_line_buffer = 10000
 
     def __init__(
-        self, server_name: str, clock: Clock, handler: "ReplicationCommandHandler"
+        self,
+        hs: "HomeServer",
+        server_name: str,
+        clock: Clock,
+        handler: "ReplicationCommandHandler",
     ):
         self.server_name = server_name
+        self.hs = hs
         self.clock = clock
         self.command_handler = handler
 
         self.last_received_command = self.clock.time_msec()
         self.last_sent_command = 0
         # When we requested the connection be closed
-        self.time_we_closed: Optional[int] = None
+        self.time_we_closed: int | None = None
 
         self.received_ping = False  # Have we received a ping from the other side
 
@@ -159,10 +163,10 @@ class BaseReplicationStreamProtocol(LineOnlyReceiver):
         self.conn_id = random_string(5)  # To dedupe in case of name clashes.
 
         # List of pending commands to send once we've established the connection
-        self.pending_commands: List[Command] = []
+        self.pending_commands: list[Command] = []
 
         # The LoopingCall for sending pings.
-        self._send_ping_loop: Optional[task.LoopingCall] = None
+        self._send_ping_loop: task.LoopingCall | None = None
 
         # a logcontext which we use for processing incoming commands. We declare it as a
         # background process so that the CPU stats get reported to prometheus.
@@ -290,9 +294,8 @@ class BaseReplicationStreamProtocol(LineOnlyReceiver):
             # if so.
 
             if isawaitable(res):
-                run_as_background_process(
+                self.hs.run_as_background_process(
                     "replication-" + cmd.get_logcontext_id(),
-                    self.server_name,
                     lambda: res,
                 )
 
@@ -470,9 +473,13 @@ class ServerReplicationStreamProtocol(BaseReplicationStreamProtocol):
     VALID_OUTBOUND_COMMANDS = VALID_SERVER_COMMANDS
 
     def __init__(
-        self, server_name: str, clock: Clock, handler: "ReplicationCommandHandler"
+        self,
+        hs: "HomeServer",
+        server_name: str,
+        clock: Clock,
+        handler: "ReplicationCommandHandler",
     ):
-        super().__init__(server_name, clock, handler)
+        super().__init__(hs, server_name, clock, handler)
 
         self.server_name = server_name
 
@@ -497,7 +504,7 @@ class ClientReplicationStreamProtocol(BaseReplicationStreamProtocol):
         clock: Clock,
         command_handler: "ReplicationCommandHandler",
     ):
-        super().__init__(server_name, clock, command_handler)
+        super().__init__(hs, server_name, clock, command_handler)
 
         self.client_name = client_name
         self.server_name = server_name
diff --git a/synapse/replication/tcp/redis.py b/synapse/replication/tcp/redis.py
index 0b1be033b1..27d43e6fba 100644
--- a/synapse/replication/tcp/redis.py
+++ b/synapse/replication/tcp/redis.py
@@ -21,7 +21,7 @@
 
 import logging
 from inspect import isawaitable
-from typing import TYPE_CHECKING, Any, Generic, List, Optional, Type, TypeVar, cast
+from typing import TYPE_CHECKING, Any, Generic, TypeVar, cast
 
 import attr
 from txredisapi import (
@@ -40,7 +40,6 @@ from synapse.logging.context import PreserveLoggingContext, make_deferred_yielda
 from synapse.metrics import SERVER_NAME_LABEL
 from synapse.metrics.background_process_metrics import (
     BackgroundProcessLoggingContext,
-    run_as_background_process,
     wrap_as_background_process,
 )
 from synapse.replication.tcp.commands import (
@@ -73,10 +72,10 @@ class ConstantProperty(Generic[T, V]):
 
     constant: V = attr.ib()
 
-    def __get__(self, obj: Optional[T], objtype: Optional[Type[T]] = None) -> V:
+    def __get__(self, obj: T | None, objtype: type[T] | None = None) -> V:
         return self.constant
 
-    def __set__(self, obj: Optional[T], value: V) -> None:
+    def __set__(self, obj: T | None, value: V) -> None:
         pass
 
 
@@ -109,9 +108,10 @@ class RedisSubscriber(SubscriberProtocol):
     """
 
     server_name: str
+    hs: "HomeServer"
     synapse_handler: "ReplicationCommandHandler"
     synapse_stream_prefix: str
-    synapse_channel_names: List[str]
+    synapse_channel_names: list[str]
     synapse_outbound_redis_connection: ConnectionHandler
 
     def __init__(self, *args: Any, **kwargs: Any):
@@ -119,7 +119,7 @@ class RedisSubscriber(SubscriberProtocol):
 
         # a logcontext which we use for processing incoming commands. We declare it as a
         # background process so that the CPU stats get reported to prometheus.
-        self._logging_context: Optional[BackgroundProcessLoggingContext] = None
+        self._logging_context: BackgroundProcessLoggingContext | None = None
 
     def _get_logging_context(self) -> BackgroundProcessLoggingContext:
         """
@@ -146,9 +146,7 @@ class RedisSubscriber(SubscriberProtocol):
     def connectionMade(self) -> None:
         logger.info("Connected to redis")
         super().connectionMade()
-        run_as_background_process(
-            "subscribe-replication", self.server_name, self._send_subscribe
-        )
+        self.hs.run_as_background_process("subscribe-replication", self._send_subscribe)
 
     async def _send_subscribe(self) -> None:
         # it's important to make sure that we only send the REPLICATE command once we
@@ -223,8 +221,8 @@ class RedisSubscriber(SubscriberProtocol):
         # if so.
 
         if isawaitable(res):
-            run_as_background_process(
-                "replication-" + cmd.get_logcontext_id(), self.server_name, lambda: res
+            self.hs.run_as_background_process(
+                "replication-" + cmd.get_logcontext_id(), lambda: res
             )
 
     def connectionLost(self, reason: Failure) -> None:  # type: ignore[override]
@@ -245,9 +243,8 @@ class RedisSubscriber(SubscriberProtocol):
         Args:
             cmd: The command to send
         """
-        run_as_background_process(
+        self.hs.run_as_background_process(
             "send-cmd",
-            self.server_name,
             self._async_send_command,
             cmd,
             # We originally started tracing background processes to avoid `There was no
@@ -296,14 +293,14 @@ class SynapseRedisFactory(RedisFactory):
         self,
         hs: "HomeServer",
         uuid: str,
-        dbid: Optional[int],
+        dbid: int | None,
         poolsize: int,
         isLazy: bool = False,
-        handler: Type = ConnectionHandler,
+        handler: type = ConnectionHandler,
         charset: str = "utf-8",
-        password: Optional[str] = None,
+        password: str | None = None,
         replyTimeout: int = 30,
-        convertNumbers: Optional[int] = True,
+        convertNumbers: int | None = True,
     ):
         super().__init__(
             uuid=uuid,
@@ -317,9 +314,8 @@ class SynapseRedisFactory(RedisFactory):
             convertNumbers=convertNumbers,
         )
 
-        self.server_name = (
-            hs.hostname
-        )  # nb must be called this for @wrap_as_background_process
+        self.hs = hs  # nb must be called this for @wrap_as_background_process
+        self.server_name = hs.hostname
 
         hs.get_clock().looping_call(self._send_ping, 30 * 1000)
 
@@ -385,7 +381,7 @@ class RedisDirectTcpReplicationClientFactory(SynapseRedisFactory):
         self,
         hs: "HomeServer",
         outbound_redis_connection: ConnectionHandler,
-        channel_names: List[str],
+        channel_names: list[str],
     ):
         super().__init__(
             hs,
@@ -397,6 +393,7 @@ class RedisDirectTcpReplicationClientFactory(SynapseRedisFactory):
         )
 
         self.server_name = hs.hostname
+        self.hs = hs
         self.synapse_handler = hs.get_replication_command_handler()
         self.synapse_stream_prefix = hs.hostname
         self.synapse_channel_names = channel_names
@@ -412,6 +409,7 @@ class RedisDirectTcpReplicationClientFactory(SynapseRedisFactory):
         # the base method does some other things than just instantiating the
         # protocol.
         p.server_name = self.server_name
+        p.hs = self.hs
         p.synapse_handler = self.synapse_handler
         p.synapse_outbound_redis_connection = self.synapse_outbound_redis_connection
         p.synapse_stream_prefix = self.synapse_stream_prefix
@@ -424,9 +422,9 @@ def lazyConnection(
     hs: "HomeServer",
     host: str = "localhost",
     port: int = 6379,
-    dbid: Optional[int] = None,
+    dbid: int | None = None,
     reconnect: bool = True,
-    password: Optional[str] = None,
+    password: str | None = None,
     replyTimeout: int = 30,
 ) -> ConnectionHandler:
     """Creates a connection to Redis that is lazily set up and reconnects if the
@@ -473,9 +471,9 @@ def lazyConnection(
 def lazyUnixConnection(
     hs: "HomeServer",
     path: str = "/tmp/redis.sock",
-    dbid: Optional[int] = None,
+    dbid: int | None = None,
     reconnect: bool = True,
-    password: Optional[str] = None,
+    password: str | None = None,
     replyTimeout: int = 30,
 ) -> ConnectionHandler:
     """Creates a connection to Redis that is lazily set up and reconnects if the
diff --git a/synapse/replication/tcp/resource.py b/synapse/replication/tcp/resource.py
index d800cfe6f6..134d8d921f 100644
--- a/synapse/replication/tcp/resource.py
+++ b/synapse/replication/tcp/resource.py
@@ -22,7 +22,7 @@
 
 import logging
 import random
-from typing import TYPE_CHECKING, List, Optional, Tuple
+from typing import TYPE_CHECKING
 
 from prometheus_client import Counter
 
@@ -30,7 +30,6 @@ from twisted.internet.interfaces import IAddress
 from twisted.internet.protocol import ServerFactory
 
 from synapse.metrics import SERVER_NAME_LABEL
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.replication.tcp.commands import PositionCommand
 from synapse.replication.tcp.protocol import ServerReplicationStreamProtocol
 from synapse.replication.tcp.streams import EventsStream
@@ -55,6 +54,7 @@ class ReplicationStreamProtocolFactory(ServerFactory):
     def __init__(self, hs: "HomeServer"):
         self.command_handler = hs.get_replication_command_handler()
         self.clock = hs.get_clock()
+        self.hs = hs
         self.server_name = hs.config.server.server_name
 
         # If we've created a `ReplicationStreamProtocolFactory` then we're
@@ -69,7 +69,7 @@ class ReplicationStreamProtocolFactory(ServerFactory):
 
     def buildProtocol(self, addr: IAddress) -> ServerReplicationStreamProtocol:
         return ServerReplicationStreamProtocol(
-            self.server_name, self.clock, self.command_handler
+            self.hs, self.server_name, self.clock, self.command_handler
         )
 
 
@@ -82,6 +82,7 @@ class ReplicationStreamer:
 
     def __init__(self, hs: "HomeServer"):
         self.server_name = hs.hostname
+        self.hs = hs
         self.store = hs.get_datastores().main
         self.clock = hs.get_clock()
         self.notifier = hs.get_notifier()
@@ -147,8 +148,8 @@ class ReplicationStreamer:
             logger.debug("Notifier poke loop already running")
             return
 
-        run_as_background_process(
-            "replication_notifier", self.server_name, self._run_notifier_loop
+        self.hs.run_as_background_process(
+            "replication_notifier", self._run_notifier_loop
         )
 
     async def _run_notifier_loop(self) -> None:
@@ -319,8 +320,8 @@ class ReplicationStreamer:
 
 
 def _batch_updates(
-    updates: List[Tuple[Token, StreamRow]],
-) -> List[Tuple[Optional[Token], StreamRow]]:
+    updates: list[tuple[Token, StreamRow]],
+) -> list[tuple[Token | None, StreamRow]]:
     """Takes a list of updates of form [(token, row)] and sets the token to
     None for all rows where the next row has the same token. This is used to
     implement batching.
@@ -336,7 +337,7 @@ def _batch_updates(
     if not updates:
         return []
 
-    new_updates: List[Tuple[Optional[Token], StreamRow]] = []
+    new_updates: list[tuple[Token | None, StreamRow]] = []
     for i, update in enumerate(updates[:-1]):
         if update[0] == updates[i + 1][0]:
             new_updates.append((None, update[1]))
diff --git a/synapse/replication/tcp/streams/__init__.py b/synapse/replication/tcp/streams/__init__.py
index 25c15e5d48..87ac0a5ae1 100644
--- a/synapse/replication/tcp/streams/__init__.py
+++ b/synapse/replication/tcp/streams/__init__.py
@@ -77,6 +77,7 @@ STREAMS_MAP = {
 __all__ = [
     "STREAMS_MAP",
     "Stream",
+    "EventsStream",
     "BackfillStream",
     "PresenceStream",
     "PresenceFederationStream",
@@ -87,6 +88,7 @@ __all__ = [
     "CachesStream",
     "DeviceListsStream",
     "ToDeviceStream",
+    "FederationStream",
     "AccountDataStream",
     "ThreadSubscriptionsStream",
     "UnPartialStatedRoomStream",
diff --git a/synapse/replication/tcp/streams/_base.py b/synapse/replication/tcp/streams/_base.py
index ec7e935d6a..4fb2aac202 100644
--- a/synapse/replication/tcp/streams/_base.py
+++ b/synapse/replication/tcp/streams/_base.py
@@ -26,9 +26,6 @@ from typing import (
     Any,
     Awaitable,
     Callable,
-    List,
-    Optional,
-    Tuple,
     TypeVar,
 )
 
@@ -56,7 +53,7 @@ Token = int
 # parsing with Stream.parse_row (which turns it into a `ROW_TYPE`). Normally it's
 # just a row from a database query, though this is dependent on the stream in question.
 #
-StreamRow = TypeVar("StreamRow", bound=Tuple)
+StreamRow = TypeVar("StreamRow", bound=tuple)
 
 # The type returned by the update_function of a stream, as well as get_updates(),
 # get_updates_since, etc.
@@ -66,7 +63,7 @@ StreamRow = TypeVar("StreamRow", bound=Tuple)
 #   * `new_last_token` is the new position in stream.
 #   * `limited` is whether there are more updates to fetch.
 #
-StreamUpdateResult = Tuple[List[Tuple[Token, StreamRow]], Token, bool]
+StreamUpdateResult = tuple[list[tuple[Token, StreamRow]], Token, bool]
 
 # The type of an update_function for a stream
 #
@@ -287,9 +284,9 @@ class BackfillStream(Stream):
         event_id: str
         room_id: str
         type: str
-        state_key: Optional[str]
-        redacts: Optional[str]
-        relates_to: Optional[str]
+        state_key: str | None
+        redacts: str | None
+        relates_to: str | None
 
     NAME = "backfill"
     ROW_TYPE = BackfillStreamRow
@@ -400,7 +397,7 @@ class TypingStream(Stream):
         room_id: str
 
         # All the users that are 'typing' right now in the specified room.
-        user_ids: List[str]
+        user_ids: list[str]
 
     NAME = "typing"
     ROW_TYPE = TypingStreamRow
@@ -410,7 +407,7 @@ class TypingStream(Stream):
             # On the writer, query the typing handler
             typing_writer_handler = hs.get_typing_writer_handler()
             update_function: Callable[
-                [str, int, int, int], Awaitable[Tuple[List[Tuple[int, Any]], int, bool]]
+                [str, int, int, int], Awaitable[tuple[list[tuple[int, Any]], int, bool]]
             ] = typing_writer_handler.get_all_typing_updates
             self.current_token_function = typing_writer_handler.get_current_token
         else:
@@ -437,7 +434,7 @@ class ReceiptsStream(_StreamFromIdGen):
         receipt_type: str
         user_id: str
         event_id: str
-        thread_id: Optional[str]
+        thread_id: str | None
         data: dict
 
     NAME = "receipts"
@@ -512,7 +509,7 @@ class CachesStream(Stream):
         """
 
         cache_func: str
-        keys: Optional[List[Any]]
+        keys: list[Any] | None
         invalidation_ts: int
 
     NAME = "caches"
@@ -641,7 +638,7 @@ class AccountDataStream(_StreamFromIdGen):
     @attr.s(slots=True, frozen=True, auto_attribs=True)
     class AccountDataStreamRow:
         user_id: str
-        room_id: Optional[str]
+        room_id: str | None
         data_type: str
 
     NAME = "account_data"
diff --git a/synapse/replication/tcp/streams/events.py b/synapse/replication/tcp/streams/events.py
index 05b55fb033..ca9f6f12da 100644
--- a/synapse/replication/tcp/streams/events.py
+++ b/synapse/replication/tcp/streams/events.py
@@ -20,7 +20,7 @@
 #
 import heapq
 from collections import defaultdict
-from typing import TYPE_CHECKING, Iterable, Optional, Tuple, Type, TypeVar, cast
+from typing import TYPE_CHECKING, Iterable, TypeVar, cast
 
 import attr
 
@@ -93,7 +93,7 @@ class BaseEventsStreamRow:
     TypeId: str
 
     @classmethod
-    def from_data(cls: Type[T], data: Iterable[Optional[str]]) -> T:
+    def from_data(cls: type[T], data: Iterable[str | None]) -> T:
         """Parse the data from the replication stream into a row.
 
         By default we just call the constructor with the data list as arguments
@@ -111,10 +111,10 @@ class EventsStreamEventRow(BaseEventsStreamRow):
     event_id: str
     room_id: str
     type: str
-    state_key: Optional[str]
-    redacts: Optional[str]
-    relates_to: Optional[str]
-    membership: Optional[str]
+    state_key: str | None
+    redacts: str | None
+    relates_to: str | None
+    membership: str | None
     rejected: bool
     outlier: bool
 
@@ -126,7 +126,7 @@ class EventsStreamCurrentStateRow(BaseEventsStreamRow):
     room_id: str
     type: str
     state_key: str
-    event_id: Optional[str]
+    event_id: str | None
 
 
 @attr.s(slots=True, frozen=True, auto_attribs=True)
@@ -136,7 +136,7 @@ class EventsStreamAllStateRow(BaseEventsStreamRow):
     room_id: str
 
 
-_EventRows: Tuple[Type[BaseEventsStreamRow], ...] = (
+_EventRows: tuple[type[BaseEventsStreamRow], ...] = (
     EventsStreamEventRow,
     EventsStreamCurrentStateRow,
     EventsStreamAllStateRow,
@@ -237,7 +237,7 @@ class EventsStream(_StreamFromIdGen):
         # distinguish the row type). At the same time, we can limit the event_rows
         # to the max stream_id from state_rows.
 
-        event_updates: Iterable[Tuple[int, Tuple]] = (
+        event_updates: Iterable[tuple[int, tuple]] = (
             (stream_id, (EventsStreamEventRow.TypeId, rest))
             for (stream_id, *rest) in event_rows
             if stream_id <= upper_limit
@@ -254,20 +254,20 @@ class EventsStream(_StreamFromIdGen):
             for room_id, stream_ids in state_updates_by_room.items()
             if len(stream_ids) >= _MAX_STATE_UPDATES_PER_ROOM
         ]
-        state_all_updates: Iterable[Tuple[int, Tuple]] = (
+        state_all_updates: Iterable[tuple[int, tuple]] = (
             (max_stream_id, (EventsStreamAllStateRow.TypeId, (room_id,)))
             for (max_stream_id, room_id) in state_all_rows
         )
 
         # Any remaining state updates are sent individually.
         state_all_rooms = {room_id for _, room_id in state_all_rows}
-        state_updates: Iterable[Tuple[int, Tuple]] = (
+        state_updates: Iterable[tuple[int, tuple]] = (
             (stream_id, (EventsStreamCurrentStateRow.TypeId, rest))
             for (stream_id, *rest) in state_rows
             if rest[0] not in state_all_rooms
         )
 
-        ex_outliers_updates: Iterable[Tuple[int, Tuple]] = (
+        ex_outliers_updates: Iterable[tuple[int, tuple]] = (
             (stream_id, (EventsStreamEventRow.TypeId, rest))
             for (stream_id, *rest) in ex_outliers_rows
         )
@@ -282,6 +282,6 @@ class EventsStream(_StreamFromIdGen):
 
     @classmethod
     def parse_row(cls, row: StreamRow) -> "EventsStreamRow":
-        (typ, data) = cast(Tuple[str, Iterable[Optional[str]]], row)
+        (typ, data) = cast(tuple[str, Iterable[str | None]], row)
         event_stream_row_data = TypeToRow[typ].from_data(data)
         return EventsStreamRow(typ, event_stream_row_data)
diff --git a/synapse/replication/tcp/streams/federation.py b/synapse/replication/tcp/streams/federation.py
index 1c2ffe86b7..c99e720381 100644
--- a/synapse/replication/tcp/streams/federation.py
+++ b/synapse/replication/tcp/streams/federation.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import TYPE_CHECKING, Any, Awaitable, Callable, List, Tuple
+from typing import TYPE_CHECKING, Any, Awaitable, Callable
 
 import attr
 
@@ -58,7 +58,7 @@ class FederationStream(Stream):
                 federation_sender.get_current_token
             )
             update_function: Callable[
-                [str, int, int, int], Awaitable[Tuple[List[Tuple[int, Any]], int, bool]]
+                [str, int, int, int], Awaitable[tuple[list[tuple[int, Any]], int, bool]]
             ] = federation_sender.get_replication_rows
 
         elif hs.should_send_federation():
@@ -88,5 +88,5 @@ class FederationStream(Stream):
     @staticmethod
     async def _stub_update_function(
         instance_name: str, from_token: int, upto_token: int, limit: int
-    ) -> Tuple[list, int, bool]:
+    ) -> tuple[list, int, bool]:
         return [], upto_token, False
diff --git a/synapse/rest/__init__.py b/synapse/rest/__init__.py
index a24ca09846..fe66494d82 100644
--- a/synapse/rest/__init__.py
+++ b/synapse/rest/__init__.py
@@ -19,7 +19,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, Callable, Dict, Iterable, List, Optional, Tuple
+from typing import TYPE_CHECKING, Callable, Iterable
 
 from synapse.http.server import HttpServer, JsonResource
 from synapse.rest import admin
@@ -42,6 +42,7 @@ from synapse.rest.client import (
     login,
     login_token_request,
     logout,
+    matrixrtc,
     mutual_rooms,
     notifications,
     openid,
@@ -77,7 +78,7 @@ if TYPE_CHECKING:
 
 RegisterServletsFunc = Callable[["HomeServer", HttpServer], None]
 
-CLIENT_SERVLET_FUNCTIONS: Tuple[RegisterServletsFunc, ...] = (
+CLIENT_SERVLET_FUNCTIONS: tuple[RegisterServletsFunc, ...] = (
     versions.register_servlets,
     initial_sync.register_servlets,
     room.register_deprecated_servlets,
@@ -89,6 +90,7 @@ CLIENT_SERVLET_FUNCTIONS: Tuple[RegisterServletsFunc, ...] = (
     presence.register_servlets,
     directory.register_servlets,
     voip.register_servlets,
+    matrixrtc.register_servlets,
     pusher.register_servlets,
     push_rule.register_servlets,
     logout.register_servlets,
@@ -126,7 +128,7 @@ CLIENT_SERVLET_FUNCTIONS: Tuple[RegisterServletsFunc, ...] = (
     thread_subscriptions.register_servlets,
 )
 
-SERVLET_GROUPS: Dict[str, Iterable[RegisterServletsFunc]] = {
+SERVLET_GROUPS: dict[str, Iterable[RegisterServletsFunc]] = {
     "client": CLIENT_SERVLET_FUNCTIONS,
 }
 
@@ -141,7 +143,7 @@ class ClientRestResource(JsonResource):
        * etc
     """
 
-    def __init__(self, hs: "HomeServer", servlet_groups: Optional[List[str]] = None):
+    def __init__(self, hs: "HomeServer", servlet_groups: list[str] | None = None):
         JsonResource.__init__(self, hs, canonical_json=False)
         if hs.config.media.can_load_media_repo:
             # This import is here to prevent a circular import failure
@@ -154,7 +156,7 @@ class ClientRestResource(JsonResource):
     def register_servlets(
         client_resource: HttpServer,
         hs: "HomeServer",
-        servlet_groups: Optional[Iterable[str]] = None,
+        servlet_groups: Iterable[str] | None = None,
     ) -> None:
         # Some servlets are only registered on the main process (and not worker
         # processes).
diff --git a/synapse/rest/admin/__init__.py b/synapse/rest/admin/__init__.py
index d9a6e99c5d..e34ebb17e6 100644
--- a/synapse/rest/admin/__init__.py
+++ b/synapse/rest/admin/__init__.py
@@ -35,7 +35,7 @@
 
 import logging
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Optional, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.errors import Codes, NotFoundError, SynapseError
 from synapse.handlers.pagination import PURGE_HISTORY_ACTION_NAME
@@ -57,6 +57,9 @@ from synapse.rest.admin.event_reports import (
     EventReportDetailRestServlet,
     EventReportsRestServlet,
 )
+from synapse.rest.admin.events import (
+    EventRestServlet,
+)
 from synapse.rest.admin.experimental_features import ExperimentalFeaturesRestServlet
 from synapse.rest.admin.federation import (
     DestinationMembershipRestServlet,
@@ -71,6 +74,7 @@ from synapse.rest.admin.registration_tokens import (
     RegistrationTokenRestServlet,
 )
 from synapse.rest.admin.rooms import (
+    AdminRoomHierarchy,
     BlockRoomRestServlet,
     DeleteRoomStatusByDeleteIdRestServlet,
     DeleteRoomStatusByRoomIdRestServlet,
@@ -134,7 +138,7 @@ class VersionServlet(RestServlet):
     def __init__(self, hs: "HomeServer"):
         self.res = {"server_version": SYNAPSE_VERSION}
 
-    def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         return HTTPStatus.OK, self.res
 
 
@@ -149,8 +153,8 @@ class PurgeHistoryRestServlet(RestServlet):
         self.auth = hs.get_auth()
 
     async def on_POST(
-        self, request: SynapseRequest, room_id: str, event_id: Optional[str]
-    ) -> Tuple[int, JsonDict]:
+        self, request: SynapseRequest, room_id: str, event_id: str | None
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         body = parse_json_object_from_request(request, allow_empty_body=True)
@@ -169,7 +173,7 @@ class PurgeHistoryRestServlet(RestServlet):
             if event.room_id != room_id:
                 raise SynapseError(HTTPStatus.BAD_REQUEST, "Event is for wrong room.")
 
-            # RoomStreamToken expects [int] not Optional[int]
+            # RoomStreamToken expects [int] not [int | None]
             assert event.internal_metadata.stream_ordering is not None
             room_token = RoomStreamToken(
                 topological=event.depth, stream=event.internal_metadata.stream_ordering
@@ -234,7 +238,7 @@ class PurgeHistoryStatusRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, purge_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         purge_task = await self.pagination_handler.get_delete_task(purge_id)
@@ -339,6 +343,8 @@ def register_servlets(hs: "HomeServer", http_server: HttpServer) -> None:
     ExperimentalFeaturesRestServlet(hs).register(http_server)
     SuspendAccountRestServlet(hs).register(http_server)
     ScheduledTasksRestServlet(hs).register(http_server)
+    AdminRoomHierarchy(hs).register(http_server)
+    EventRestServlet(hs).register(http_server)
 
 
 def register_servlets_for_client_rest_resource(
diff --git a/synapse/rest/admin/background_updates.py b/synapse/rest/admin/background_updates.py
index 6fba616d3a..96190c416d 100644
--- a/synapse/rest/admin/background_updates.py
+++ b/synapse/rest/admin/background_updates.py
@@ -20,7 +20,7 @@
 #
 import logging
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.errors import SynapseError
 from synapse.http.servlet import (
@@ -47,7 +47,7 @@ class BackgroundUpdateEnabledRestServlet(RestServlet):
         self._auth = hs.get_auth()
         self._data_stores = hs.get_datastores()
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
 
         # We need to check that all configured databases have updates enabled.
@@ -56,7 +56,7 @@ class BackgroundUpdateEnabledRestServlet(RestServlet):
 
         return HTTPStatus.OK, {"enabled": enabled}
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
 
         body = parse_json_object_from_request(request)
@@ -88,7 +88,7 @@ class BackgroundUpdateRestServlet(RestServlet):
         self._auth = hs.get_auth()
         self._data_stores = hs.get_datastores()
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
 
         # We need to check that all configured databases have updates enabled.
@@ -121,7 +121,7 @@ class BackgroundUpdateStartJobRestServlet(RestServlet):
         self._auth = hs.get_auth()
         self._store = hs.get_datastores().main
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
 
         body = parse_json_object_from_request(request)
diff --git a/synapse/rest/admin/devices.py b/synapse/rest/admin/devices.py
index c488bce58e..c8e9242ce8 100644
--- a/synapse/rest/admin/devices.py
+++ b/synapse/rest/admin/devices.py
@@ -20,7 +20,7 @@
 #
 import logging
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.errors import NotFoundError, SynapseError
 from synapse.http.servlet import (
@@ -56,7 +56,7 @@ class DeviceRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, user_id: str, device_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         target_user = UserID.from_string(user_id)
@@ -76,7 +76,7 @@ class DeviceRestServlet(RestServlet):
 
     async def on_DELETE(
         self, request: SynapseRequest, user_id: str, device_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         target_user = UserID.from_string(user_id)
@@ -92,7 +92,7 @@ class DeviceRestServlet(RestServlet):
 
     async def on_PUT(
         self, request: SynapseRequest, user_id: str, device_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         target_user = UserID.from_string(user_id)
@@ -128,7 +128,7 @@ class DevicesRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         target_user = UserID.from_string(user_id)
@@ -157,7 +157,7 @@ class DevicesRestServlet(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         """Creates a new device for the user."""
         await assert_requester_is_admin(self.auth, request)
 
@@ -201,7 +201,7 @@ class DeleteDevicesRestServlet(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         target_user = UserID.from_string(user_id)
diff --git a/synapse/rest/admin/event_reports.py b/synapse/rest/admin/event_reports.py
index ff1abc0697..5e8f85de7e 100644
--- a/synapse/rest/admin/event_reports.py
+++ b/synapse/rest/admin/event_reports.py
@@ -21,7 +21,7 @@
 
 import logging
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.constants import Direction
 from synapse.api.errors import Codes, NotFoundError, SynapseError
@@ -65,7 +65,7 @@ class EventReportsRestServlet(RestServlet):
         self._auth = hs.get_auth()
         self._store = hs.get_datastores().main
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
 
         start = parse_integer(request, "from", default=0)
@@ -123,7 +123,7 @@ class EventReportDetailRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, report_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
 
         message = (
@@ -149,7 +149,7 @@ class EventReportDetailRestServlet(RestServlet):
 
     async def on_DELETE(
         self, request: SynapseRequest, report_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
 
         message = (
diff --git a/synapse/rest/admin/events.py b/synapse/rest/admin/events.py
new file mode 100644
index 0000000000..1c39d5caf3
--- /dev/null
+++ b/synapse/rest/admin/events.py
@@ -0,0 +1,69 @@
+from http import HTTPStatus
+from typing import TYPE_CHECKING
+
+from synapse.api.errors import NotFoundError
+from synapse.events.utils import (
+    SerializeEventConfig,
+    format_event_raw,
+    serialize_event,
+)
+from synapse.http.servlet import RestServlet
+from synapse.http.site import SynapseRequest
+from synapse.rest.admin import admin_patterns
+from synapse.rest.admin._base import assert_user_is_admin
+from synapse.storage.databases.main.events_worker import EventRedactBehaviour
+from synapse.types import JsonDict
+
+if TYPE_CHECKING:
+    from synapse.server import HomeServer
+
+
+class EventRestServlet(RestServlet):
+    """
+    Get an event that is known to the homeserver.
+    The requester must have administrator access in Synapse.
+
+    GET /_synapse/admin/v1/fetch_event/<event_id>
+    returns:
+        200 OK with event json if the event is known to the homeserver. Otherwise raises
+        a NotFound error.
+
+    Args:
+        event_id: the id of the requested event.
+    Returns:
+        JSON blob of the event
+    """
+
+    PATTERNS = admin_patterns("/fetch_event/(?P<event_id>[^/]*)$")
+
+    def __init__(self, hs: "HomeServer"):
+        self._auth = hs.get_auth()
+        self._store = hs.get_datastores().main
+        self._clock = hs.get_clock()
+
+    async def on_GET(
+        self, request: SynapseRequest, event_id: str
+    ) -> tuple[int, JsonDict]:
+        requester = await self._auth.get_user_by_req(request)
+        await assert_user_is_admin(self._auth, requester)
+
+        event = await self._store.get_event(
+            event_id,
+            EventRedactBehaviour.as_is,
+            allow_none=True,
+        )
+
+        if event is None:
+            raise NotFoundError("Event not found")
+
+        config = SerializeEventConfig(
+            as_client_event=False,
+            event_format=format_event_raw,
+            requester=requester,
+            only_event_fields=None,
+            include_stripped_room_state=True,
+            include_admin_metadata=True,
+        )
+        res = {"event": serialize_event(event, self._clock.time_msec(), config=config)}
+
+        return HTTPStatus.OK, res
diff --git a/synapse/rest/admin/experimental_features.py b/synapse/rest/admin/experimental_features.py
index 3d3015cef7..abdb937793 100644
--- a/synapse/rest/admin/experimental_features.py
+++ b/synapse/rest/admin/experimental_features.py
@@ -22,7 +22,7 @@
 
 from enum import Enum
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Dict, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.errors import SynapseError
 from synapse.http.servlet import RestServlet, parse_json_object_from_request
@@ -74,7 +74,7 @@ class ExperimentalFeaturesRestServlet(RestServlet):
         self,
         request: SynapseRequest,
         user_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         """
         List which features are enabled for a given user
         """
@@ -99,7 +99,7 @@ class ExperimentalFeaturesRestServlet(RestServlet):
 
     async def on_PUT(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[HTTPStatus, Dict]:
+    ) -> tuple[HTTPStatus, dict]:
         """
         Enable or disable the provided features for the requester
         """
diff --git a/synapse/rest/admin/federation.py b/synapse/rest/admin/federation.py
index d85a04b825..e958ef9747 100644
--- a/synapse/rest/admin/federation.py
+++ b/synapse/rest/admin/federation.py
@@ -20,7 +20,7 @@
 #
 import logging
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.constants import Direction
 from synapse.api.errors import NotFoundError, SynapseError
@@ -58,7 +58,7 @@ class ListDestinationsRestServlet(RestServlet):
         self._auth = hs.get_auth()
         self._store = hs.get_datastores().main
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
 
         start = parse_integer(request, "from", default=0)
@@ -115,7 +115,7 @@ class DestinationRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, destination: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
 
         if not await self._store.is_destination_known(destination):
@@ -175,7 +175,7 @@ class DestinationMembershipRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, destination: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
 
         if not await self._store.is_destination_known(destination):
@@ -224,7 +224,7 @@ class DestinationResetConnectionRestServlet(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, destination: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
 
         if not await self._store.is_destination_known(destination):
diff --git a/synapse/rest/admin/media.py b/synapse/rest/admin/media.py
index 8732c0bf9d..d5346fe0d5 100644
--- a/synapse/rest/admin/media.py
+++ b/synapse/rest/admin/media.py
@@ -20,7 +20,7 @@
 #
 import logging
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Optional, Tuple
+from typing import TYPE_CHECKING
 
 import attr
 
@@ -67,7 +67,7 @@ class QueryMediaById(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, server_name: str, media_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         await assert_user_is_admin(self.auth, requester)
 
@@ -134,7 +134,7 @@ class QuarantineMediaInRoom(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         await assert_user_is_admin(self.auth, requester)
 
@@ -161,7 +161,7 @@ class QuarantineMediaByUser(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         await assert_user_is_admin(self.auth, requester)
 
@@ -190,7 +190,7 @@ class QuarantineMediaByID(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, server_name: str, media_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         await assert_user_is_admin(self.auth, requester)
 
@@ -219,7 +219,7 @@ class UnquarantineMediaByID(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, server_name: str, media_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         logger.info("Remove from quarantine media by ID: %s/%s", server_name, media_id)
@@ -241,7 +241,7 @@ class ProtectMediaByID(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, media_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         logger.info("Protecting local media by ID: %s", media_id)
@@ -263,7 +263,7 @@ class UnprotectMediaByID(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, media_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         logger.info("Unprotecting local media by ID: %s", media_id)
@@ -285,7 +285,7 @@ class ListMediaInRoom(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         local_mxcs, remote_mxcs = await self.store.get_media_mxcs_in_room(room_id)
@@ -300,7 +300,7 @@ class PurgeMediaCacheRestServlet(RestServlet):
         self.media_repository = hs.get_media_repository()
         self.auth = hs.get_auth()
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         before_ts = parse_integer(request, "before_ts", required=True)
@@ -338,7 +338,7 @@ class DeleteMediaByID(RestServlet):
 
     async def on_DELETE(
         self, request: SynapseRequest, server_name: str, media_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         if not self._is_mine_server_name(server_name):
@@ -374,8 +374,8 @@ class DeleteMediaByDateSize(RestServlet):
         self.media_repository = hs.get_media_repository()
 
     async def on_POST(
-        self, request: SynapseRequest, server_name: Optional[str] = None
-    ) -> Tuple[int, JsonDict]:
+        self, request: SynapseRequest, server_name: str | None = None
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         before_ts = parse_integer(request, "before_ts", required=True)
@@ -433,7 +433,7 @@ class UserMediaRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         # This will always be set by the time Twisted calls us.
         assert request.args is not None
 
@@ -477,7 +477,7 @@ class UserMediaRestServlet(RestServlet):
 
     async def on_DELETE(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         # This will always be set by the time Twisted calls us.
         assert request.args is not None
 
diff --git a/synapse/rest/admin/registration_tokens.py b/synapse/rest/admin/registration_tokens.py
index bec2331590..ea266403a0 100644
--- a/synapse/rest/admin/registration_tokens.py
+++ b/synapse/rest/admin/registration_tokens.py
@@ -22,7 +22,7 @@
 import logging
 import string
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.errors import Codes, NotFoundError, SynapseError
 from synapse.http.servlet import (
@@ -80,7 +80,7 @@ class ListRegistrationTokensRestServlet(RestServlet):
         self.auth = hs.get_auth()
         self.store = hs.get_datastores().main
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
         valid = parse_boolean(request, "valid")
         token_list = await self.store.get_registration_tokens(valid)
@@ -133,7 +133,7 @@ class NewRegistrationTokenRestServlet(RestServlet):
         self.allowed_chars = string.ascii_letters + string.digits + "._~-"
         self.allowed_chars_set = set(self.allowed_chars)
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
         body = parse_json_object_from_request(request)
 
@@ -282,7 +282,7 @@ class RegistrationTokenRestServlet(RestServlet):
         self.auth = hs.get_auth()
         self.store = hs.get_datastores().main
 
-    async def on_GET(self, request: SynapseRequest, token: str) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest, token: str) -> tuple[int, JsonDict]:
         """Retrieve a registration token."""
         await assert_requester_is_admin(self.auth, request)
         token_info = await self.store.get_one_registration_token(token)
@@ -293,7 +293,7 @@ class RegistrationTokenRestServlet(RestServlet):
 
         return HTTPStatus.OK, token_info
 
-    async def on_PUT(self, request: SynapseRequest, token: str) -> Tuple[int, JsonDict]:
+    async def on_PUT(self, request: SynapseRequest, token: str) -> tuple[int, JsonDict]:
         """Update a registration token."""
         await assert_requester_is_admin(self.auth, request)
         body = parse_json_object_from_request(request)
@@ -348,7 +348,7 @@ class RegistrationTokenRestServlet(RestServlet):
 
     async def on_DELETE(
         self, request: SynapseRequest, token: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         """Delete a registration token."""
         await assert_requester_is_admin(self.auth, request)
 
diff --git a/synapse/rest/admin/rooms.py b/synapse/rest/admin/rooms.py
index 5bed89c2c4..cf24bc628a 100644
--- a/synapse/rest/admin/rooms.py
+++ b/synapse/rest/admin/rooms.py
@@ -20,7 +20,7 @@
 #
 import logging
 from http import HTTPStatus
-from typing import TYPE_CHECKING, List, Optional, Tuple, cast
+from typing import TYPE_CHECKING, cast
 
 import attr
 from immutabledict import immutabledict
@@ -63,6 +63,50 @@ if TYPE_CHECKING:
 logger = logging.getLogger(__name__)
 
 
+class AdminRoomHierarchy(RestServlet):
+    """
+    Given a room, returns room details on that room and any space children of
+    the provided room. Does not reach out over federation to fetch information about
+    any remote rooms which the server is not currently participating in
+    """
+
+    PATTERNS = admin_patterns("/rooms/(?P<room_id>[^/]*)/hierarchy$")
+
+    def __init__(self, hs: "HomeServer"):
+        self._auth = hs.get_auth()
+        self._room_summary_handler = hs.get_room_summary_handler()
+        self._store = hs.get_datastores().main
+        self._storage_controllers = hs.get_storage_controllers()
+
+    async def on_GET(
+        self, request: SynapseRequest, room_id: str
+    ) -> tuple[int, JsonDict]:
+        requester = await self._auth.get_user_by_req(request)
+        await assert_user_is_admin(self._auth, requester)
+
+        max_depth = parse_integer(request, "max_depth")
+        limit = parse_integer(request, "limit")
+
+        room_entry_summary = await self._room_summary_handler.get_room_hierarchy(
+            requester,
+            room_id,
+            # We omit details about remote rooms because we only care
+            # about managing rooms local to the homeserver. This
+            # also immensely helps with the response time of the
+            # endpoint since we don't need to reach out over federation.
+            # There is a trade-off as this will leave holes where
+            # information about public/peekable remote rooms the
+            # server is not participating in will be omitted.
+            omit_remote_room_hierarchy=True,
+            admin_skip_room_visibility_check=True,
+            max_depth=max_depth,
+            limit=limit,
+            from_token=parse_string(request, "from"),
+        )
+
+        return HTTPStatus.OK, room_entry_summary
+
+
 class RoomRestV2Servlet(RestServlet):
     """Delete a room from server asynchronously with a background task.
 
@@ -88,7 +132,7 @@ class RoomRestV2Servlet(RestServlet):
 
     async def on_DELETE(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self._auth.get_user_by_req(request)
         await assert_user_is_admin(self._auth, requester)
 
@@ -167,7 +211,7 @@ class DeleteRoomStatusByRoomIdRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
 
         if not RoomID.is_valid(room_id):
@@ -198,7 +242,7 @@ class DeleteRoomStatusByDeleteIdRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, delete_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
 
         delete_task = await self._pagination_handler.get_delete_task(delete_id)
@@ -224,7 +268,7 @@ class ListRoomRestServlet(RestServlet):
         self.auth = hs.get_auth()
         self.admin_handler = hs.get_admin_handler()
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         # Extract query parameters
@@ -319,7 +363,7 @@ class RoomRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         ret = await self.store.get_room_with_stats(room_id)
@@ -337,7 +381,7 @@ class RoomRestServlet(RestServlet):
 
     async def on_DELETE(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         return await self._delete_room(
             request,
             room_id,
@@ -353,7 +397,7 @@ class RoomRestServlet(RestServlet):
         auth: "Auth",
         room_shutdown_handler: "RoomShutdownHandler",
         pagination_handler: "PaginationHandler",
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await auth.get_user_by_req(request)
         await assert_user_is_admin(auth, requester)
 
@@ -429,7 +473,7 @@ class RoomMembersRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         room = await self.store.get_room(room_id)
@@ -458,7 +502,7 @@ class RoomStateRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         room = await self.store.get_room(room_id)
@@ -498,7 +542,7 @@ class JoinRoomAliasServlet(ResolveRoomIdMixin, RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, room_identifier: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         # This will always be set by the time Twisted calls us.
         assert request.args is not None
 
@@ -521,7 +565,7 @@ class JoinRoomAliasServlet(ResolveRoomIdMixin, RestServlet):
 
         # Get the room ID from the identifier.
         try:
-            remote_room_hosts: Optional[List[str]] = [
+            remote_room_hosts: list[str] | None = [
                 x.decode("ascii") for x in request.args[b"server_name"]
             ]
         except Exception:
@@ -591,7 +635,7 @@ class MakeRoomAdminRestServlet(ResolveRoomIdMixin, RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, room_identifier: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         await assert_user_is_admin(self.auth, requester)
         content = parse_json_object_from_request(request, allow_empty_body=True)
@@ -756,7 +800,7 @@ class ForwardExtremitiesRestServlet(ResolveRoomIdMixin, RestServlet):
 
     async def on_DELETE(
         self, request: SynapseRequest, room_identifier: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         room_id, _ = await self.resolve_room_id(room_identifier)
@@ -766,7 +810,7 @@ class ForwardExtremitiesRestServlet(ResolveRoomIdMixin, RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, room_identifier: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         room_id, _ = await self.resolve_room_id(room_identifier)
@@ -805,7 +849,7 @@ class RoomEventContextServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, room_id: str, event_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=False)
         await assert_user_is_admin(self.auth, requester)
 
@@ -871,7 +915,7 @@ class BlockRoomRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
 
         if not RoomID.is_valid(room_id):
@@ -891,7 +935,7 @@ class BlockRoomRestServlet(RestServlet):
 
     async def on_PUT(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self._auth.get_user_by_req(request)
         await assert_user_is_admin(self._auth, requester)
 
@@ -935,7 +979,7 @@ class RoomMessagesRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self._auth.get_user_by_req(request)
         await assert_user_is_admin(self._auth, requester)
 
@@ -997,7 +1041,7 @@ class RoomTimestampToEventRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self._auth.get_user_by_req(request)
         await assert_user_is_admin(self._auth, requester)
 
diff --git a/synapse/rest/admin/scheduled_tasks.py b/synapse/rest/admin/scheduled_tasks.py
index 2ae13021b9..41c402b424 100644
--- a/synapse/rest/admin/scheduled_tasks.py
+++ b/synapse/rest/admin/scheduled_tasks.py
@@ -13,7 +13,7 @@
 #
 #
 #
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.http.servlet import RestServlet, parse_integer, parse_string
 from synapse.http.site import SynapseRequest
@@ -35,7 +35,7 @@ class ScheduledTasksRestServlet(RestServlet):
         self._auth = hs.get_auth()
         self._store = hs.get_datastores().main
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
 
         # extract query params
diff --git a/synapse/rest/admin/server_notice_servlet.py b/synapse/rest/admin/server_notice_servlet.py
index f3150e88d7..50d2f35b18 100644
--- a/synapse/rest/admin/server_notice_servlet.py
+++ b/synapse/rest/admin/server_notice_servlet.py
@@ -18,7 +18,7 @@
 #
 #
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Optional, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.constants import EventTypes
 from synapse.api.errors import NotFoundError, SynapseError
@@ -80,8 +80,8 @@ class SendServerNoticeServlet(RestServlet):
         self,
         request: SynapseRequest,
         requester: Requester,
-        txn_id: Optional[str],
-    ) -> Tuple[int, JsonDict]:
+        txn_id: str | None,
+    ) -> tuple[int, JsonDict]:
         await assert_user_is_admin(self.auth, requester)
         body = parse_json_object_from_request(request)
         assert_params_in_dict(body, ("user_id", "content"))
@@ -118,13 +118,13 @@ class SendServerNoticeServlet(RestServlet):
     async def on_POST(
         self,
         request: SynapseRequest,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         return await self._do(request, requester, None)
 
     async def on_PUT(
         self, request: SynapseRequest, txn_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         set_tag("txn_id", txn_id)
         return await self.txns.fetch_or_execute_request(
diff --git a/synapse/rest/admin/statistics.py b/synapse/rest/admin/statistics.py
index 0adc5b7005..3de1d4e9bd 100644
--- a/synapse/rest/admin/statistics.py
+++ b/synapse/rest/admin/statistics.py
@@ -21,7 +21,7 @@
 
 import logging
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.constants import Direction
 from synapse.api.errors import Codes, SynapseError
@@ -48,7 +48,7 @@ class UserMediaStatisticsRestServlet(RestServlet):
         self.auth = hs.get_auth()
         self.store = hs.get_datastores().main
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         order_by = parse_string(
@@ -119,7 +119,7 @@ class LargestRoomsStatistics(RestServlet):
         self.auth = hs.get_auth()
         self.stats_controller = hs.get_storage_controllers().stats
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         room_sizes = await self.stats_controller.get_room_db_size_estimate()
diff --git a/synapse/rest/admin/username_available.py b/synapse/rest/admin/username_available.py
index 2d642f7d6b..fb0cee42da 100644
--- a/synapse/rest/admin/username_available.py
+++ b/synapse/rest/admin/username_available.py
@@ -20,7 +20,7 @@
 #
 import logging
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.http.servlet import RestServlet, parse_string
 from synapse.http.site import SynapseRequest
@@ -50,7 +50,7 @@ class UsernameAvailableRestServlet(RestServlet):
         self.auth = hs.get_auth()
         self.registration_handler = hs.get_registration_handler()
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         username = parse_string(request, "username", required=True)
diff --git a/synapse/rest/admin/users.py b/synapse/rest/admin/users.py
index 25a38dc4ac..42e9f8043d 100644
--- a/synapse/rest/admin/users.py
+++ b/synapse/rest/admin/users.py
@@ -23,11 +23,11 @@ import hmac
 import logging
 import secrets
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Dict, List, Optional, Tuple, Union
+from typing import TYPE_CHECKING
 
 import attr
+from pydantic import StrictBool, StrictInt, StrictStr
 
-from synapse._pydantic_compat import StrictBool, StrictInt, StrictStr
 from synapse.api.constants import Direction
 from synapse.api.errors import Codes, NotFoundError, SynapseError
 from synapse.http.servlet import (
@@ -113,7 +113,7 @@ class UsersRestServletV2(RestServlet):
             hs.config.mas.enabled or hs.config.experimental.msc3861.enabled
         )
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         start = parse_integer(request, "from", default=0)
@@ -163,8 +163,8 @@ class UsersRestServletV2(RestServlet):
 
         direction = parse_enum(request, "dir", Direction, default=Direction.FORWARDS)
 
-        # twisted.web.server.Request.args is incorrectly defined as Optional[Any]
-        args: Dict[bytes, List[bytes]] = request.args  # type: ignore
+        # twisted.web.server.Request.args is incorrectly defined as Any | None
+        args: dict[bytes, list[bytes]] = request.args  # type: ignore
         not_user_types = parse_strings_from_args(args, "not_user_type")
 
         users, total = await self.store.get_users_paginate(
@@ -195,7 +195,7 @@ class UsersRestServletV2(RestServlet):
 
         return HTTPStatus.OK, ret
 
-    def _parse_parameter_deactivated(self, request: SynapseRequest) -> Optional[bool]:
+    def _parse_parameter_deactivated(self, request: SynapseRequest) -> bool | None:
         """
         Return None (no filtering) if `deactivated` is `true`, otherwise return `False`
         (exclude deactivated users from the results).
@@ -206,9 +206,7 @@ class UsersRestServletV2(RestServlet):
 class UsersRestServletV3(UsersRestServletV2):
     PATTERNS = admin_patterns("/users$", "v3")
 
-    def _parse_parameter_deactivated(
-        self, request: SynapseRequest
-    ) -> Union[bool, None]:
+    def _parse_parameter_deactivated(self, request: SynapseRequest) -> bool | None:
         return parse_boolean(request, "deactivated")
 
 
@@ -256,7 +254,7 @@ class UserRestServletV2(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonMapping]:
+    ) -> tuple[int, JsonMapping]:
         await assert_requester_is_admin(self.auth, request)
 
         target_user = UserID.from_string(user_id)
@@ -271,7 +269,7 @@ class UserRestServletV2(RestServlet):
 
     async def on_PUT(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonMapping]:
+    ) -> tuple[int, JsonMapping]:
         requester = await self.auth.get_user_by_req(request)
         await assert_user_is_admin(self.auth, requester)
 
@@ -340,7 +338,7 @@ class UserRestServletV2(RestServlet):
                 HTTPStatus.BAD_REQUEST, "An user can't be deactivated and locked"
             )
 
-        approved: Optional[bool] = None
+        approved: bool | None = None
         if "approved" in body and self._msc3866_enabled:
             approved = body["approved"]
             if not isinstance(approved, bool):
@@ -349,14 +347,14 @@ class UserRestServletV2(RestServlet):
                     "'approved' parameter is not of type boolean",
                 )
 
-        # convert List[Dict[str, str]] into List[Tuple[str, str]]
+        # convert list[dict[str, str]] into list[tuple[str, str]]
         if external_ids is not None:
             new_external_ids = [
                 (external_id["auth_provider"], external_id["external_id"])
                 for external_id in external_ids
             ]
 
-        # convert List[Dict[str, str]] into Set[Tuple[str, str]]
+        # convert list[dict[str, str]] into set[tuple[str, str]]
         if threepids is not None:
             new_threepids = {
                 (threepid["medium"], threepid["address"]) for threepid in threepids
@@ -545,7 +543,7 @@ class UserRegisterServlet(RestServlet):
     def __init__(self, hs: "HomeServer"):
         self.auth_handler = hs.get_auth_handler()
         self.reactor = hs.get_reactor()
-        self.nonces: Dict[str, int] = {}
+        self.nonces: dict[str, int] = {}
         self.hs = hs
         self._all_user_types = hs.config.user_types.all_user_types
 
@@ -559,7 +557,7 @@ class UserRegisterServlet(RestServlet):
             if now - v > self.NONCE_TIMEOUT:
                 del self.nonces[k]
 
-    def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         """
         Generate a new nonce.
         """
@@ -569,7 +567,7 @@ class UserRegisterServlet(RestServlet):
         self.nonces[nonce] = int(self.reactor.seconds())
         return HTTPStatus.OK, {"nonce": nonce}
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         self._clear_old_nonces()
 
         if not self.hs.config.registration.registration_shared_secret:
@@ -730,7 +728,7 @@ class WhoisRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonMapping]:
+    ) -> tuple[int, JsonMapping]:
         target_user = UserID.from_string(user_id)
         requester = await self.auth.get_user_by_req(request)
 
@@ -756,7 +754,7 @@ class DeactivateAccountRestServlet(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, target_user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         await assert_user_is_admin(self.auth, requester)
 
@@ -801,7 +799,7 @@ class SuspendAccountRestServlet(RestServlet):
 
     async def on_PUT(
         self, request: SynapseRequest, target_user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         await assert_user_is_admin(self.auth, requester)
 
@@ -828,7 +826,7 @@ class AccountValidityRenewServlet(RestServlet):
         )
         self.auth = hs.get_auth()
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         if self.account_validity_module_callbacks.on_legacy_admin_request_callback:
@@ -878,7 +876,7 @@ class ResetPasswordRestServlet(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, target_user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         """Post request to allow an administrator reset password for a user.
         This needs user to have administrator access in Synapse.
         """
@@ -920,7 +918,7 @@ class SearchUsersRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, target_user_id: str
-    ) -> Tuple[int, Optional[List[JsonDict]]]:
+    ) -> tuple[int, list[JsonDict] | None]:
         """Get request to search user table for specific users according to
         search term.
         This needs user to have a administrator access in Synapse.
@@ -989,7 +987,7 @@ class UserAdminServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         target_user = UserID.from_string(user_id)
@@ -1006,7 +1004,7 @@ class UserAdminServlet(RestServlet):
 
     async def on_PUT(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         await assert_user_is_admin(self.auth, requester)
         auth_user = requester.user
@@ -1047,7 +1045,7 @@ class UserMembershipRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         room_ids = await self.store.get_rooms_for_user(user_id)
@@ -1079,7 +1077,7 @@ class PushersRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         if not self.is_mine(UserID.from_string(user_id)):
@@ -1122,7 +1120,7 @@ class UserTokenRestServlet(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         await assert_user_is_admin(self.auth, requester)
         auth_user = requester.user
@@ -1190,7 +1188,7 @@ class ShadowBanRestServlet(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         if not self.is_mine_id(user_id):
@@ -1204,7 +1202,7 @@ class ShadowBanRestServlet(RestServlet):
 
     async def on_DELETE(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         if not self.is_mine_id(user_id):
@@ -1242,7 +1240,7 @@ class RateLimitRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         if not self.is_mine_id(user_id):
@@ -1273,7 +1271,7 @@ class RateLimitRestServlet(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         if not self.is_mine_id(user_id):
@@ -1321,7 +1319,7 @@ class RateLimitRestServlet(RestServlet):
 
     async def on_DELETE(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self.auth, request)
 
         if not self.is_mine_id(user_id):
@@ -1349,7 +1347,7 @@ class AccountDataRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
 
         if not self._is_mine_id(user_id):
@@ -1390,7 +1388,7 @@ class UserReplaceMasterCrossSigningKeyRestServlet(RestServlet):
         self,
         request: SynapseRequest,
         user_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
 
         if user_id is None:
@@ -1424,7 +1422,7 @@ class UserByExternalId(RestServlet):
         request: SynapseRequest,
         provider: str,
         external_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
 
         user_id = await self._store.get_user_by_external_id(provider, external_id)
@@ -1449,7 +1447,7 @@ class UserByThreePid(RestServlet):
         request: SynapseRequest,
         medium: str,
         address: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
 
         user_id = await self._store.get_user_id_by_threepid(medium, address)
@@ -1475,14 +1473,14 @@ class RedactUser(RestServlet):
         self.admin_handler = hs.get_admin_handler()
 
     class PostBody(RequestBodyModel):
-        rooms: List[StrictStr]
-        reason: Optional[StrictStr]
-        limit: Optional[StrictInt]
-        use_admin: Optional[StrictBool]
+        rooms: list[StrictStr]
+        reason: StrictStr | None = None
+        limit: StrictInt | None = None
+        use_admin: StrictBool | None = None
 
     async def on_POST(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self._auth.get_user_by_req(request)
         await assert_user_is_admin(self._auth, requester)
 
@@ -1531,7 +1529,7 @@ class RedactUserStatus(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, redact_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
 
         task = await self.admin_handler.get_redact_task(redact_id)
@@ -1574,7 +1572,7 @@ class UserInvitesCount(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
         from_ts = parse_integer(request, "from_ts", required=True)
 
@@ -1599,7 +1597,7 @@ class UserJoinedRoomCount(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await assert_requester_is_admin(self._auth, request)
         from_ts = parse_integer(request, "from_ts", required=True)
 
diff --git a/synapse/rest/client/_base.py b/synapse/rest/client/_base.py
index 6cf37869d8..fad7234718 100644
--- a/synapse/rest/client/_base.py
+++ b/synapse/rest/client/_base.py
@@ -23,7 +23,7 @@
 
 import logging
 import re
-from typing import Any, Awaitable, Callable, Iterable, Pattern, Tuple, TypeVar, cast
+from typing import Any, Awaitable, Callable, Iterable, Pattern, TypeVar, cast
 
 from synapse.api.errors import InteractiveAuthIncompleteError
 from synapse.api.urls import CLIENT_API_PREFIX
@@ -86,7 +86,7 @@ def set_timeline_upper_limit(filter_json: JsonDict, filter_timeline_limit: int)
         )
 
 
-C = TypeVar("C", bound=Callable[..., Awaitable[Tuple[int, JsonDict]]])
+C = TypeVar("C", bound=Callable[..., Awaitable[tuple[int, JsonDict]]])
 
 
 def interactive_auth_handler(orig: C) -> C:
@@ -104,7 +104,7 @@ def interactive_auth_handler(orig: C) -> C:
         await self.auth_handler.check_auth
     """
 
-    async def wrapped(*args: Any, **kwargs: Any) -> Tuple[int, JsonDict]:
+    async def wrapped(*args: Any, **kwargs: Any) -> tuple[int, JsonDict]:
         try:
             return await orig(*args, **kwargs)
         except InteractiveAuthIncompleteError as e:
diff --git a/synapse/rest/client/account.py b/synapse/rest/client/account.py
index d9f0c169e8..b052052be0 100644
--- a/synapse/rest/client/account.py
+++ b/synapse/rest/client/account.py
@@ -21,14 +21,15 @@
 #
 import logging
 import random
-from typing import TYPE_CHECKING, List, Literal, Optional, Tuple
+from typing import TYPE_CHECKING, Literal
 from urllib.parse import urlparse
 
 import attr
+from pydantic import StrictBool, StrictStr, StringConstraints
+from typing_extensions import Annotated
 
 from twisted.web.server import Request
 
-from synapse._pydantic_compat import StrictBool, StrictStr, constr
 from synapse.api.constants import LoginType
 from synapse.api.errors import (
     Codes,
@@ -89,7 +90,7 @@ class EmailPasswordRequestTokenRestServlet(RestServlet):
                 template_text=self.config.email.email_password_reset_template_text,
             )
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         if not self.config.email.can_verify_email:
             logger.warning(
                 "User password resets have been disabled due to lack of email config"
@@ -160,16 +161,14 @@ class PasswordRestServlet(RestServlet):
         self._set_password_handler = hs.get_set_password_handler()
 
     class PostBody(RequestBodyModel):
-        auth: Optional[AuthenticationData] = None
+        auth: AuthenticationData | None = None
         logout_devices: StrictBool = True
-        if TYPE_CHECKING:
-            # workaround for https://github.com/samuelcolvin/pydantic/issues/156
-            new_password: Optional[StrictStr] = None
-        else:
-            new_password: Optional[constr(max_length=512, strict=True)] = None
+        new_password: (
+            Annotated[str, StringConstraints(max_length=512, strict=True)] | None
+        ) = None
 
     @interactive_auth_handler
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         body = parse_and_validate_json_object_from_request(request, self.PostBody)
 
         # we do basic sanity checks here because the auth layer will store these
@@ -260,7 +259,7 @@ class PasswordRestServlet(RestServlet):
         # If we have a password in this request, prefer it. Otherwise, use the
         # password hash from an earlier request.
         if new_password:
-            password_hash: Optional[str] = await self.auth_handler.hash(new_password)
+            password_hash: str | None = await self.auth_handler.hash(new_password)
         elif session_id is not None:
             password_hash = existing_session_password_hash
         else:
@@ -290,13 +289,13 @@ class DeactivateAccountRestServlet(RestServlet):
         self._deactivate_account_handler = hs.get_deactivate_account_handler()
 
     class PostBody(RequestBodyModel):
-        auth: Optional[AuthenticationData] = None
-        id_server: Optional[StrictStr] = None
+        auth: AuthenticationData | None = None
+        id_server: StrictStr | None = None
         # Not specced, see https://github.com/matrix-org/matrix-spec/issues/297
         erase: StrictBool = False
 
     @interactive_auth_handler
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         body = parse_and_validate_json_object_from_request(request, self.PostBody)
 
         requester = await self.auth.get_user_by_req(request)
@@ -341,7 +340,7 @@ class EmailThreepidRequestTokenRestServlet(RestServlet):
                 template_text=self.config.email.email_add_threepid_template_text,
             )
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         if not self.hs.config.registration.enable_3pid_changes:
             raise SynapseError(
                 400, "3PID changes are disabled on this server", Codes.FORBIDDEN
@@ -418,7 +417,7 @@ class MsisdnThreepidRequestTokenRestServlet(RestServlet):
         self.store = self.hs.get_datastores().main
         self.identity_handler = hs.get_identity_handler()
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         body = parse_and_validate_json_object_from_request(
             request, MsisdnRequestTokenBody
         )
@@ -567,7 +566,7 @@ class AddThreepidMsisdnSubmitTokenServlet(RestServlet):
         self.store = hs.get_datastores().main
         self.identity_handler = hs.get_identity_handler()
 
-    async def on_POST(self, request: Request) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: Request) -> tuple[int, JsonDict]:
         if not self.config.registration.account_threepid_delegate_msisdn:
             raise SynapseError(
                 400,
@@ -601,7 +600,7 @@ class ThreepidRestServlet(RestServlet):
         self.auth_handler = hs.get_auth_handler()
         self.datastore = self.hs.get_datastores().main
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
 
         threepids = await self.datastore.user_get_threepids(requester.user.to_string())
@@ -612,7 +611,7 @@ class ThreepidRestServlet(RestServlet):
     # the endpoint is deprecated. (If you really want to, you could do this by reusing
     # ThreePidBindRestServelet.PostBody with an `alias_generator` to handle
     # `threePidCreds` versus `three_pid_creds`.
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         if self.hs.config.mas.enabled or self.hs.config.experimental.msc3861.enabled:
             raise NotFoundError(errcode=Codes.UNRECOGNIZED)
 
@@ -664,12 +663,12 @@ class ThreepidAddRestServlet(RestServlet):
         self.auth_handler = hs.get_auth_handler()
 
     class PostBody(RequestBodyModel):
-        auth: Optional[AuthenticationData] = None
+        auth: AuthenticationData | None = None
         client_secret: ClientSecretStr
         sid: StrictStr
 
     @interactive_auth_handler
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         if not self.hs.config.registration.enable_3pid_changes:
             raise SynapseError(
                 400, "3PID changes are disabled on this server", Codes.FORBIDDEN
@@ -718,7 +717,7 @@ class ThreepidBindRestServlet(RestServlet):
         id_server: StrictStr
         sid: StrictStr
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         body = parse_and_validate_json_object_from_request(request, self.PostBody)
 
         requester = await self.auth.get_user_by_req(request)
@@ -743,10 +742,10 @@ class ThreepidUnbindRestServlet(RestServlet):
 
     class PostBody(RequestBodyModel):
         address: StrictStr
-        id_server: Optional[StrictStr] = None
+        id_server: StrictStr | None = None
         medium: Literal["email", "msisdn"]
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         """Unbind the given 3pid from a specific identity server, or identity servers that are
         known to have this 3pid bound
         """
@@ -772,10 +771,10 @@ class ThreepidDeleteRestServlet(RestServlet):
 
     class PostBody(RequestBodyModel):
         address: StrictStr
-        id_server: Optional[StrictStr] = None
+        id_server: StrictStr | None = None
         medium: Literal["email", "msisdn"]
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         if not self.hs.config.registration.enable_3pid_changes:
             raise SynapseError(
                 400, "3PID changes are disabled on this server", Codes.FORBIDDEN
@@ -859,7 +858,7 @@ class WhoamiRestServlet(RestServlet):
         super().__init__()
         self.auth = hs.get_auth()
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
 
         response = {
@@ -889,9 +888,9 @@ class AccountStatusRestServlet(RestServlet):
     class PostBody(RequestBodyModel):
         # TODO: we could validate that each user id is an mxid here, and/or parse it
         #       as a UserID
-        user_ids: List[StrictStr]
+        user_ids: list[StrictStr]
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await self._auth.get_user_by_req(request)
 
         body = parse_and_validate_json_object_from_request(request, self.PostBody)
diff --git a/synapse/rest/client/account_data.py b/synapse/rest/client/account_data.py
index 734c9e992f..b18232fc56 100644
--- a/synapse/rest/client/account_data.py
+++ b/synapse/rest/client/account_data.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Optional, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.constants import AccountDataTypes, ReceiptTypes
 from synapse.api.errors import AuthError, Codes, NotFoundError, SynapseError
@@ -75,7 +75,7 @@ class AccountDataServlet(RestServlet):
 
     async def on_PUT(
         self, request: SynapseRequest, user_id: str, account_data_type: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         if user_id != requester.user.to_string():
             raise AuthError(403, "Cannot add account data for other users.")
@@ -101,16 +101,16 @@ class AccountDataServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, user_id: str, account_data_type: str
-    ) -> Tuple[int, JsonMapping]:
+    ) -> tuple[int, JsonMapping]:
         requester = await self.auth.get_user_by_req(request)
         if user_id != requester.user.to_string():
             raise AuthError(403, "Cannot get account data for other users.")
 
         # Push rules are stored in a separate table and must be queried separately.
         if account_data_type == AccountDataTypes.PUSH_RULES:
-            account_data: Optional[
-                JsonMapping
-            ] = await self._push_rules_handler.push_rules_for_user(requester.user)
+            account_data: (
+                JsonMapping | None
+            ) = await self._push_rules_handler.push_rules_for_user(requester.user)
         else:
             account_data = await self.store.get_global_account_data_by_type_for_user(
                 user_id, account_data_type
@@ -152,7 +152,7 @@ class UnstableAccountDataServlet(RestServlet):
         request: SynapseRequest,
         user_id: str,
         account_data_type: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         if user_id != requester.user.to_string():
             raise AuthError(403, "Cannot delete account data for other users.")
@@ -191,7 +191,7 @@ class RoomAccountDataServlet(RestServlet):
         user_id: str,
         room_id: str,
         account_data_type: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         if user_id != requester.user.to_string():
             raise AuthError(403, "Cannot add account data for other users.")
@@ -230,7 +230,7 @@ class RoomAccountDataServlet(RestServlet):
         user_id: str,
         room_id: str,
         account_data_type: str,
-    ) -> Tuple[int, JsonMapping]:
+    ) -> tuple[int, JsonMapping]:
         requester = await self.auth.get_user_by_req(request)
         if user_id != requester.user.to_string():
             raise AuthError(403, "Cannot get account data for other users.")
@@ -244,7 +244,7 @@ class RoomAccountDataServlet(RestServlet):
 
         # Room-specific push rules are not currently supported.
         if account_data_type == AccountDataTypes.PUSH_RULES:
-            account_data: Optional[JsonMapping] = {}
+            account_data: JsonMapping | None = {}
         else:
             account_data = await self.store.get_account_data_for_room_and_type(
                 user_id, room_id, account_data_type
@@ -288,7 +288,7 @@ class UnstableRoomAccountDataServlet(RestServlet):
         user_id: str,
         room_id: str,
         account_data_type: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         if user_id != requester.user.to_string():
             raise AuthError(403, "Cannot delete account data for other users.")
diff --git a/synapse/rest/client/account_validity.py b/synapse/rest/client/account_validity.py
index ec7836b647..1c60539054 100644
--- a/synapse/rest/client/account_validity.py
+++ b/synapse/rest/client/account_validity.py
@@ -19,7 +19,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from twisted.web.server import Request
 
@@ -90,7 +90,7 @@ class AccountValiditySendMailServlet(RestServlet):
             hs.config.account_validity.account_validity_renew_by_email_enabled
         )
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_expired=True)
         user_id = requester.user.to_string()
         await self.account_activity_handler.send_renewal_email_to_user(user_id)
diff --git a/synapse/rest/client/appservice_ping.py b/synapse/rest/client/appservice_ping.py
index 1f9662a95a..7e2ac15783 100644
--- a/synapse/rest/client/appservice_ping.py
+++ b/synapse/rest/client/appservice_ping.py
@@ -22,7 +22,7 @@
 import logging
 import time
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Any, Dict, Tuple
+from typing import TYPE_CHECKING, Any
 
 from synapse.api.errors import (
     CodeMessageException,
@@ -58,7 +58,7 @@ class AppservicePingRestServlet(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, appservice_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
 
         if not requester.app_service:
@@ -97,7 +97,7 @@ class AppservicePingRestServlet(RestServlet):
                 Codes.AS_PING_CONNECTION_TIMEOUT,
             )
         except CodeMessageException as e:
-            additional_fields: Dict[str, Any] = {"status": e.code}
+            additional_fields: dict[str, Any] = {"status": e.code}
             if isinstance(e, HttpResponseException):
                 try:
                     additional_fields["body"] = e.response.decode("utf-8")
diff --git a/synapse/rest/client/auth_metadata.py b/synapse/rest/client/auth_metadata.py
index 4b5d997478..702f550906 100644
--- a/synapse/rest/client/auth_metadata.py
+++ b/synapse/rest/client/auth_metadata.py
@@ -13,7 +13,7 @@
 # limitations under the License.
 import logging
 import typing
-from typing import Tuple, cast
+from typing import cast
 
 from synapse.api.auth.mas import MasDelegatedAuth
 from synapse.api.errors import Codes, SynapseError
@@ -48,7 +48,7 @@ class AuthIssuerServlet(RestServlet):
         self._config = hs.config
         self._auth = hs.get_auth()
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         if self._config.mas.enabled:
             assert isinstance(self._auth, MasDelegatedAuth)
             return 200, {"issuer": await self._auth.issuer()}
@@ -93,7 +93,7 @@ class AuthMetadataServlet(RestServlet):
         self._config = hs.config
         self._auth = hs.get_auth()
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         if self._config.mas.enabled:
             assert isinstance(self._auth, MasDelegatedAuth)
             return 200, await self._auth.auth_metadata()
diff --git a/synapse/rest/client/capabilities.py b/synapse/rest/client/capabilities.py
index a279db1cc5..baff999ab0 100644
--- a/synapse/rest/client/capabilities.py
+++ b/synapse/rest/client/capabilities.py
@@ -19,7 +19,7 @@
 #
 import logging
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.room_versions import KNOWN_ROOM_VERSIONS, MSC3244_CAPABILITIES
 from synapse.http.server import HttpServer
@@ -48,7 +48,7 @@ class CapabilitiesRestServlet(RestServlet):
         self.auth = hs.get_auth()
         self.auth_handler = hs.get_auth_handler()
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await self.auth.get_user_by_req(request, allow_guest=True)
         change_password = self.auth_handler.can_change_password()
 
diff --git a/synapse/rest/client/delayed_events.py b/synapse/rest/client/delayed_events.py
index 2dd5a60b2b..80abacbc9d 100644
--- a/synapse/rest/client/delayed_events.py
+++ b/synapse/rest/client/delayed_events.py
@@ -17,7 +17,7 @@
 import logging
 from enum import Enum
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.errors import Codes, SynapseError
 from synapse.http.server import HttpServer
@@ -52,7 +52,7 @@ class UpdateDelayedEventServlet(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, delay_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
 
         body = parse_json_object_from_request(request)
@@ -95,7 +95,7 @@ class DelayedEventsServlet(RestServlet):
         self.auth = hs.get_auth()
         self.delayed_events_handler = hs.get_delayed_events_handler()
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         # TODO: Support Pagination stream API ("from" query parameter)
         delayed_events = await self.delayed_events_handler.get_all_for_user(requester)
diff --git a/synapse/rest/client/devices.py b/synapse/rest/client/devices.py
index 0777abde7f..636e4b6031 100644
--- a/synapse/rest/client/devices.py
+++ b/synapse/rest/client/devices.py
@@ -22,9 +22,10 @@
 
 import logging
 from http import HTTPStatus
-from typing import TYPE_CHECKING, List, Optional, Tuple
+from typing import TYPE_CHECKING
+
+from pydantic import ConfigDict, StrictStr
 
-from synapse._pydantic_compat import Extra, StrictStr
 from synapse.api import errors
 from synapse.api.errors import NotFoundError, SynapseError, UnrecognizedRequestError
 from synapse.http.server import HttpServer
@@ -56,7 +57,7 @@ class DevicesRestServlet(RestServlet):
         self.device_handler = hs.get_device_handler()
         self._msc3852_enabled = hs.config.experimental.msc3852_enabled
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
         devices = await self.device_handler.get_devices_by_user(
             requester.user.to_string()
@@ -94,11 +95,11 @@ class DeleteDevicesRestServlet(RestServlet):
         self.auth_handler = hs.get_auth_handler()
 
     class PostBody(RequestBodyModel):
-        auth: Optional[AuthenticationData]
-        devices: List[StrictStr]
+        auth: AuthenticationData | None = None
+        devices: list[StrictStr]
 
     @interactive_auth_handler
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
 
         try:
@@ -108,11 +109,11 @@ class DeleteDevicesRestServlet(RestServlet):
                 # TODO: Can/should we remove this fallback now?
                 # deal with older clients which didn't pass a JSON dict
                 # the same as those that pass an empty dict
-                body = self.PostBody.parse_obj({})
+                body = self.PostBody.model_validate({})
             else:
                 raise e
 
-        if requester.app_service and requester.app_service.msc4190_device_management:
+        if requester.app_service:
             # MSC4190 can skip UIA for this endpoint
             pass
         else:
@@ -150,7 +151,7 @@ class DeviceRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, device_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
         device = await self.device_handler.get_device(
             requester.user.to_string(), device_id
@@ -172,12 +173,12 @@ class DeviceRestServlet(RestServlet):
         return 200, device
 
     class DeleteBody(RequestBodyModel):
-        auth: Optional[AuthenticationData]
+        auth: AuthenticationData | None = None
 
     @interactive_auth_handler
     async def on_DELETE(
         self, request: SynapseRequest, device_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
 
         try:
@@ -188,11 +189,11 @@ class DeviceRestServlet(RestServlet):
                 # TODO: can/should we remove this fallback now?
                 # deal with older clients which didn't pass a JSON dict
                 # the same as those that pass an empty dict
-                body = self.DeleteBody.parse_obj({})
+                body = self.DeleteBody.model_validate({})
             else:
                 raise
 
-        if requester.app_service and requester.app_service.msc4190_device_management:
+        if requester.app_service:
             # MSC4190 allows appservices to delete devices through this endpoint without UIA
             # It's also allowed with MSC3861 enabled
             pass
@@ -217,17 +218,17 @@ class DeviceRestServlet(RestServlet):
         return 200, {}
 
     class PutBody(RequestBodyModel):
-        display_name: Optional[StrictStr]
+        display_name: StrictStr | None = None
 
     async def on_PUT(
         self, request: SynapseRequest, device_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
 
         body = parse_and_validate_json_object_from_request(request, self.PutBody)
 
         # MSC4190 allows appservices to create devices through this endpoint
-        if requester.app_service and requester.app_service.msc4190_device_management:
+        if requester.app_service:
             created = await self.device_handler.upsert_device(
                 user_id=requester.user.to_string(),
                 device_id=device_id,
@@ -247,8 +248,7 @@ class DehydratedDeviceDataModel(RequestBodyModel):
     Expects other freeform fields. Use .dict() to access them.
     """
 
-    class Config:
-        extra = Extra.allow
+    model_config = ConfigDict(extra="allow")
 
     algorithm: StrictStr
 
@@ -302,7 +302,7 @@ class DehydratedDeviceServlet(RestServlet):
         handler = hs.get_device_handler()
         self.device_handler = handler
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         dehydrated_device = await self.device_handler.get_dehydrated_device(
             requester.user.to_string()
@@ -316,9 +316,9 @@ class DehydratedDeviceServlet(RestServlet):
 
     class PutBody(RequestBodyModel):
         device_data: DehydratedDeviceDataModel
-        initial_device_display_name: Optional[StrictStr]
+        initial_device_display_name: StrictStr | None = None
 
-    async def on_PUT(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_PUT(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         submission = parse_and_validate_json_object_from_request(request, self.PutBody)
         requester = await self.auth.get_user_by_req(request)
 
@@ -364,7 +364,7 @@ class ClaimDehydratedDeviceServlet(RestServlet):
     class PostBody(RequestBodyModel):
         device_id: StrictStr
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
 
         submission = parse_and_validate_json_object_from_request(request, self.PostBody)
@@ -391,11 +391,11 @@ class DehydratedDeviceEventsServlet(RestServlet):
         self.store = hs.get_datastores().main
 
     class PostBody(RequestBodyModel):
-        next_batch: Optional[StrictStr]
+        next_batch: StrictStr | None = None
 
     async def on_POST(
         self, request: SynapseRequest, device_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
 
         next_batch = parse_and_validate_json_object_from_request(
@@ -501,7 +501,7 @@ class DehydratedDeviceV2Servlet(RestServlet):
         self.e2e_keys_handler = hs.get_e2e_keys_handler()
         self.device_handler = handler
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
 
         dehydrated_device = await self.device_handler.get_dehydrated_device(
@@ -515,7 +515,7 @@ class DehydratedDeviceV2Servlet(RestServlet):
         else:
             raise errors.NotFoundError("No dehydrated device available")
 
-    async def on_DELETE(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_DELETE(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
 
         dehydrated_device = await self.device_handler.get_dehydrated_device(
@@ -538,12 +538,10 @@ class DehydratedDeviceV2Servlet(RestServlet):
     class PutBody(RequestBodyModel):
         device_data: DehydratedDeviceDataModel
         device_id: StrictStr
-        initial_device_display_name: Optional[StrictStr]
+        initial_device_display_name: StrictStr | None
+        model_config = ConfigDict(extra="allow")
 
-        class Config:
-            extra = Extra.allow
-
-    async def on_PUT(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_PUT(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         submission = parse_and_validate_json_object_from_request(request, self.PutBody)
         requester = await self.auth.get_user_by_req(request)
         user_id = requester.user.to_string()
diff --git a/synapse/rest/client/directory.py b/synapse/rest/client/directory.py
index 479f489623..0b334f9b0b 100644
--- a/synapse/rest/client/directory.py
+++ b/synapse/rest/client/directory.py
@@ -20,11 +20,12 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, List, Literal, Optional, Tuple
+from typing import TYPE_CHECKING, Literal
+
+from pydantic import StrictStr
 
 from twisted.web.server import Request
 
-from synapse._pydantic_compat import StrictStr
 from synapse.api.errors import AuthError, Codes, NotFoundError, SynapseError
 from synapse.http.server import HttpServer
 from synapse.http.servlet import (
@@ -59,7 +60,7 @@ class ClientDirectoryServer(RestServlet):
         self.directory_handler = hs.get_directory_handler()
         self.auth = hs.get_auth()
 
-    async def on_GET(self, request: Request, room_alias: str) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: Request, room_alias: str) -> tuple[int, JsonDict]:
         if not RoomAlias.is_valid(room_alias):
             raise SynapseError(400, "Room alias invalid", errcode=Codes.INVALID_PARAM)
         room_alias_obj = RoomAlias.from_string(room_alias)
@@ -72,11 +73,11 @@ class ClientDirectoryServer(RestServlet):
         # TODO: get Pydantic to validate that this is a valid room id?
         room_id: StrictStr
         # `servers` is unspecced
-        servers: Optional[List[StrictStr]] = None
+        servers: list[StrictStr] | None = None
 
     async def on_PUT(
         self, request: SynapseRequest, room_alias: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         if not RoomAlias.is_valid(room_alias):
             raise SynapseError(400, "Room alias invalid", errcode=Codes.INVALID_PARAM)
         room_alias_obj = RoomAlias.from_string(room_alias)
@@ -103,7 +104,7 @@ class ClientDirectoryServer(RestServlet):
 
     async def on_DELETE(
         self, request: SynapseRequest, room_alias: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         if not RoomAlias.is_valid(room_alias):
             raise SynapseError(400, "Room alias invalid", errcode=Codes.INVALID_PARAM)
         room_alias_obj = RoomAlias.from_string(room_alias)
@@ -141,7 +142,7 @@ class ClientDirectoryListServer(RestServlet):
         self.directory_handler = hs.get_directory_handler()
         self.auth = hs.get_auth()
 
-    async def on_GET(self, request: Request, room_id: str) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: Request, room_id: str) -> tuple[int, JsonDict]:
         room = await self.store.get_room(room_id)
         if room is None:
             raise NotFoundError("Unknown room")
@@ -153,7 +154,7 @@ class ClientDirectoryListServer(RestServlet):
 
     async def on_PUT(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
 
         content = parse_and_validate_json_object_from_request(request, self.PutBody)
@@ -181,13 +182,13 @@ class ClientAppserviceDirectoryListServer(RestServlet):
 
     async def on_PUT(
         self, request: SynapseRequest, network_id: str, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         content = parse_and_validate_json_object_from_request(request, self.PutBody)
         return await self._edit(request, network_id, room_id, content.visibility)
 
     async def on_DELETE(
         self, request: SynapseRequest, network_id: str, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         return await self._edit(request, network_id, room_id, "private")
 
     async def _edit(
@@ -196,7 +197,7 @@ class ClientAppserviceDirectoryListServer(RestServlet):
         network_id: str,
         room_id: str,
         visibility: Literal["public", "private"],
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         if not requester.app_service:
             raise AuthError(
diff --git a/synapse/rest/client/events.py b/synapse/rest/client/events.py
index ad23cc76ce..de73c96fd0 100644
--- a/synapse/rest/client/events.py
+++ b/synapse/rest/client/events.py
@@ -22,7 +22,7 @@
 """This module contains REST servlets to do with event streaming, /events."""
 
 import logging
-from typing import TYPE_CHECKING, Dict, List, Tuple, Union
+from typing import TYPE_CHECKING
 
 from synapse.api.errors import SynapseError
 from synapse.events.utils import SerializeEventConfig
@@ -51,9 +51,9 @@ class EventStreamRestServlet(RestServlet):
         self.auth = hs.get_auth()
         self.store = hs.get_datastores().main
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
-        args: Dict[bytes, List[bytes]] = request.args  # type: ignore
+        args: dict[bytes, list[bytes]] = request.args  # type: ignore
         if requester.is_guest:
             if b"room_id" not in args:
                 raise SynapseError(400, "Guest users must specify room_id param")
@@ -96,7 +96,7 @@ class EventRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, event_id: str
-    ) -> Tuple[int, Union[str, JsonDict]]:
+    ) -> tuple[int, str | JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         event = await self.event_handler.get_event(requester.user, None, event_id)
 
diff --git a/synapse/rest/client/filter.py b/synapse/rest/client/filter.py
index f1e881975f..cfe82e1473 100644
--- a/synapse/rest/client/filter.py
+++ b/synapse/rest/client/filter.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.errors import AuthError, NotFoundError, StoreError, SynapseError
 from synapse.http.server import HttpServer
@@ -48,7 +48,7 @@ class GetFilterRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, user_id: str, filter_id: str
-    ) -> Tuple[int, JsonMapping]:
+    ) -> tuple[int, JsonMapping]:
         target_user = UserID.from_string(user_id)
         requester = await self.auth.get_user_by_req(request)
 
@@ -87,7 +87,7 @@ class CreateFilterRestServlet(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         target_user = UserID.from_string(user_id)
         requester = await self.auth.get_user_by_req(request)
 
diff --git a/synapse/rest/client/initial_sync.py b/synapse/rest/client/initial_sync.py
index a2c50f5d58..c20e007c5b 100644
--- a/synapse/rest/client/initial_sync.py
+++ b/synapse/rest/client/initial_sync.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import TYPE_CHECKING, Dict, List, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.http.server import HttpServer
 from synapse.http.servlet import RestServlet, parse_boolean
@@ -43,9 +43,9 @@ class InitialSyncRestServlet(RestServlet):
         self.auth = hs.get_auth()
         self.store = hs.get_datastores().main
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
-        args: Dict[bytes, List[bytes]] = request.args  # type: ignore
+        args: dict[bytes, list[bytes]] = request.args  # type: ignore
         as_client_event = b"raw" not in args
         pagination_config = await PaginationConfig.from_request(
             self.store, request, default_limit=10
diff --git a/synapse/rest/client/keys.py b/synapse/rest/client/keys.py
index 6cf480952e..5f488674b4 100644
--- a/synapse/rest/client/keys.py
+++ b/synapse/rest/client/keys.py
@@ -23,10 +23,14 @@
 import logging
 import re
 from collections import Counter
-from typing import TYPE_CHECKING, Any, Dict, Optional, Tuple
+from http import HTTPStatus
+from typing import TYPE_CHECKING, Any, Mapping
+
+from pydantic import StrictBool, StrictStr, field_validator
 
 from synapse.api.auth.mas import MasDelegatedAuth
 from synapse.api.errors import (
+    Codes,
     InteractiveAuthIncompleteError,
     InvalidAPICallError,
     SynapseError,
@@ -37,11 +41,13 @@ from synapse.http.servlet import (
     parse_integer,
     parse_json_object_from_request,
     parse_string,
+    validate_json_object,
 )
 from synapse.http.site import SynapseRequest
 from synapse.logging.opentracing import log_kv, set_tag
 from synapse.rest.client._base import client_patterns, interactive_auth_handler
 from synapse.types import JsonDict, StreamToken
+from synapse.types.rest import RequestBodyModel
 from synapse.util.cancellation import cancellable
 
 if TYPE_CHECKING:
@@ -59,7 +65,6 @@ class KeyUploadServlet(RestServlet):
         "device_keys": {
             "user_id": "<user_id>",
             "device_id": "<device_id>",
-            "valid_until_ts": <millisecond_timestamp>,
             "algorithms": [
                 "m.olm.curve25519-aes-sha2",
             ]
@@ -111,12 +116,125 @@ class KeyUploadServlet(RestServlet):
         self._clock = hs.get_clock()
         self._store = hs.get_datastores().main
 
+    class KeyUploadRequestBody(RequestBodyModel):
+        """
+        The body of a `POST /_matrix/client/v3/keys/upload` request.
+
+        Based on https://spec.matrix.org/v1.16/client-server-api/#post_matrixclientv3keysupload.
+        """
+
+        class DeviceKeys(RequestBodyModel):
+            algorithms: list[StrictStr]
+            """The encryption algorithms supported by this device."""
+
+            device_id: StrictStr
+            """The ID of the device these keys belong to. Must match the device ID used when logging in."""
+
+            keys: Mapping[StrictStr, StrictStr]
+            """
+            Public identity keys. The names of the properties should be in the
+            format `<algorithm>:<device_id>`. The keys themselves should be encoded as
+            specified by the key algorithm.
+            """
+
+            signatures: Mapping[StrictStr, Mapping[StrictStr, StrictStr]]
+            """Signatures for the device key object. A map from user ID, to a map from "<algorithm>:<device_id>" to the signature."""
+
+            user_id: StrictStr
+            """The ID of the user the device belongs to. Must match the user ID used when logging in."""
+
+        class KeyObject(RequestBodyModel):
+            key: StrictStr
+            """The key, encoded using unpadded base64."""
+
+            fallback: StrictBool | None = False
+            """Whether this is a fallback key. Only used when handling fallback keys."""
+
+            signatures: Mapping[StrictStr, Mapping[StrictStr, StrictStr]]
+            """Signature for the device. Mapped from user ID to another map of key signing identifier to the signature itself.
+
+            See the following for more detail: https://spec.matrix.org/v1.16/appendices/#signing-details
+            """
+
+        device_keys: DeviceKeys | None = None
+        """Identity keys for the device. May be absent if no new identity keys are required."""
+
+        fallback_keys: Mapping[StrictStr, StrictStr | KeyObject] | None = None
+        """
+        The public key which should be used if the device's one-time keys are
+        exhausted. The fallback key is not deleted once used, but should be
+        replaced when additional one-time keys are being uploaded. The server
+        will notify the client of the fallback key being used through `/sync`.
+
+        There can only be at most one key per algorithm uploaded, and the server
+        will only persist one key per algorithm.
+
+        When uploading a signed key, an additional fallback: true key should be
+        included to denote that the key is a fallback key.
+
+        May be absent if a new fallback key is not required.
+        """
+
+        @field_validator("fallback_keys", mode="before")
+        @classmethod
+        def validate_fallback_keys(cls, v: Any) -> Any:
+            if v is None:
+                return v
+            if not isinstance(v, dict):
+                raise TypeError("fallback_keys must be a mapping")
+
+            for k in v.keys():
+                if not len(k.split(":")) == 2:
+                    raise SynapseError(
+                        code=HTTPStatus.BAD_REQUEST,
+                        errcode=Codes.BAD_JSON,
+                        msg=f"Invalid fallback_keys key {k!r}. "
+                        'Expected "<algorithm>:<device_id>".',
+                    )
+            return v
+
+        one_time_keys: Mapping[StrictStr, StrictStr | KeyObject] | None = None
+        """
+        One-time public keys for "pre-key" messages. The names of the properties
+        should be in the format `<algorithm>:<key_id>`.
+
+        The format of the key is determined by the key algorithm, see:
+        https://spec.matrix.org/v1.16/client-server-api/#key-algorithms.
+        """
+
+        @field_validator("one_time_keys", mode="before")
+        @classmethod
+        def validate_one_time_keys(cls, v: Any) -> Any:
+            if v is None:
+                return v
+            if not isinstance(v, dict):
+                raise TypeError("one_time_keys must be a mapping")
+
+            for k, _ in v.items():
+                if not len(k.split(":")) == 2:
+                    raise SynapseError(
+                        code=HTTPStatus.BAD_REQUEST,
+                        errcode=Codes.BAD_JSON,
+                        msg=f"Invalid one_time_keys key {k!r}. "
+                        'Expected "<algorithm>:<device_id>".',
+                    )
+            return v
+
     async def on_POST(
-        self, request: SynapseRequest, device_id: Optional[str]
-    ) -> Tuple[int, JsonDict]:
+        self, request: SynapseRequest, device_id: str | None
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
         user_id = requester.user.to_string()
+
+        # Parse the request body. Validate separately, as the handler expects a
+        # plain dict, rather than any parsed object.
+        #
+        # Note: It would be nice to work with a parsed object, but the handler
+        # needs to encode portions of the request body as canonical JSON before
+        # storing the result in the DB. There's little point in converted to a
+        # parsed object and then back to a dict.
         body = parse_json_object_from_request(request)
+        validate_json_object(body, self.KeyUploadRequestBody)
 
         if device_id is not None:
             # Providing the device_id should only be done for setting keys
@@ -149,8 +267,31 @@ class KeyUploadServlet(RestServlet):
                 400, "To upload keys, you must pass device_id when authenticating"
             )
 
+        if "device_keys" in body and isinstance(body["device_keys"], dict):
+            # Validate the provided `user_id` and `device_id` fields in
+            # `device_keys` match that of the requesting user. We can't do
+            # this directly in the pydantic model as we don't have access
+            # to the requester yet.
+            #
+            # TODO: We could use ValidationInfo when we switch to Pydantic v2.
+            # https://docs.pydantic.dev/latest/concepts/validators/#validation-info
+            if body["device_keys"].get("user_id") != user_id:
+                raise SynapseError(
+                    code=HTTPStatus.BAD_REQUEST,
+                    errcode=Codes.BAD_JSON,
+                    msg="Provided `user_id` in `device_keys` does not match that of the authenticated user",
+                )
+            if body["device_keys"].get("device_id") != device_id:
+                raise SynapseError(
+                    code=HTTPStatus.BAD_REQUEST,
+                    errcode=Codes.BAD_JSON,
+                    msg="Provided `device_id` in `device_keys` does not match that of the authenticated user device",
+                )
+
         result = await self.e2e_keys_handler.upload_keys_for_user(
-            user_id=user_id, device_id=device_id, keys=body
+            user_id=user_id,
+            device_id=device_id,
+            keys=body,
         )
 
         return 200, result
@@ -199,7 +340,7 @@ class KeyQueryServlet(RestServlet):
         self.e2e_keys_handler = hs.get_e2e_keys_handler()
 
     @cancellable
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
         user_id = requester.user.to_string()
         device_id = requester.device_id
@@ -244,7 +385,7 @@ class KeyChangesServlet(RestServlet):
         self.store = hs.get_datastores().main
 
     @cancellable
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
 
         from_token_string = parse_string(request, "from", required=True)
@@ -298,13 +439,13 @@ class OneTimeKeyServlet(RestServlet):
         self.auth = hs.get_auth()
         self.e2e_keys_handler = hs.get_e2e_keys_handler()
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
         timeout = parse_integer(request, "timeout", 10 * 1000)
         body = parse_json_object_from_request(request)
 
         # Generate a count for each algorithm, which is hard-coded to 1.
-        query: Dict[str, Dict[str, Dict[str, int]]] = {}
+        query: dict[str, dict[str, dict[str, int]]] = {}
         for user_id, one_time_keys in body.get("one_time_keys", {}).items():
             for device_id, algorithm in one_time_keys.items():
                 query.setdefault(user_id, {})[device_id] = {algorithm: 1}
@@ -346,13 +487,13 @@ class UnstableOneTimeKeyServlet(RestServlet):
         self.auth = hs.get_auth()
         self.e2e_keys_handler = hs.get_e2e_keys_handler()
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
         timeout = parse_integer(request, "timeout", 10 * 1000)
         body = parse_json_object_from_request(request)
 
         # Generate a count for each algorithm.
-        query: Dict[str, Dict[str, Dict[str, int]]] = {}
+        query: dict[str, dict[str, dict[str, int]]] = {}
         for user_id, one_time_keys in body.get("one_time_keys", {}).items():
             for device_id, algorithms in one_time_keys.items():
                 query.setdefault(user_id, {})[device_id] = Counter(algorithms)
@@ -382,7 +523,7 @@ class SigningKeyUploadServlet(RestServlet):
         self.auth_handler = hs.get_auth_handler()
 
     @interactive_auth_handler
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         user_id = requester.user.to_string()
         body = parse_json_object_from_request(request)
@@ -399,15 +540,11 @@ class SigningKeyUploadServlet(RestServlet):
         if not keys_are_different:
             return 200, {}
 
-        # MSC4190 can skip UIA for replacing cross-signing keys as well.
-        is_appservice_with_msc4190 = (
-            requester.app_service and requester.app_service.msc4190_device_management
-        )
-
         # The keys are different; is x-signing set up? If no, then this is first-time
         # setup, and that is allowed without UIA, per MSC3967.
         # If yes, then we need to authenticate the change.
-        if is_cross_signing_setup and not is_appservice_with_msc4190:
+        # MSC4190 can skip UIA for replacing cross-signing keys as well.
+        if is_cross_signing_setup and not requester.app_service:
             # With MSC3861, UIA is not possible. Instead, the auth service has to
             # explicitly mark the master key as replaceable.
             if self.hs.config.mas.enabled:
@@ -519,7 +656,7 @@ class SignaturesUploadServlet(RestServlet):
         self.auth = hs.get_auth()
         self.e2e_keys_handler = hs.get_e2e_keys_handler()
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
         user_id = requester.user.to_string()
         body = parse_json_object_from_request(request)
diff --git a/synapse/rest/client/knock.py b/synapse/rest/client/knock.py
index d7a17e1b35..cd3afda11e 100644
--- a/synapse/rest/client/knock.py
+++ b/synapse/rest/client/knock.py
@@ -20,7 +20,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, Dict, List, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.constants import Membership
 from synapse.api.errors import SynapseError
@@ -58,7 +58,7 @@ class KnockRoomAliasServlet(RestServlet):
         self,
         request: SynapseRequest,
         room_identifier: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
 
         content = parse_json_object_from_request(request)
@@ -69,8 +69,8 @@ class KnockRoomAliasServlet(RestServlet):
         if RoomID.is_valid(room_identifier):
             room_id = room_identifier
 
-            # twisted.web.server.Request.args is incorrectly defined as Optional[Any]
-            args: Dict[bytes, List[bytes]] = request.args  # type: ignore
+            # twisted.web.server.Request.args is incorrectly defined as Any | None
+            args: dict[bytes, list[bytes]] = request.args  # type: ignore
             # Prefer via over server_name (deprecated with MSC4156)
             remote_room_hosts = parse_strings_from_args(args, "via", required=False)
             if remote_room_hosts is None:
diff --git a/synapse/rest/client/login.py b/synapse/rest/client/login.py
index 921232a3ea..fe3cb9aa3d 100644
--- a/synapse/rest/client/login.py
+++ b/synapse/rest/client/login.py
@@ -26,12 +26,7 @@ from typing import (
     Any,
     Awaitable,
     Callable,
-    Dict,
-    List,
-    Optional,
-    Tuple,
     TypedDict,
-    Union,
 )
 
 from synapse.api.constants import ApprovalNoticeMedium
@@ -70,12 +65,12 @@ logger = logging.getLogger(__name__)
 
 class LoginResponse(TypedDict, total=False):
     user_id: str
-    access_token: Optional[str]
+    access_token: str | None
     home_server: str
-    expires_in_ms: Optional[int]
-    refresh_token: Optional[str]
-    device_id: Optional[str]
-    well_known: Optional[Dict[str, Any]]
+    expires_in_ms: int | None
+    refresh_token: str | None
+    device_id: str | None
+    well_known: dict[str, Any] | None
 
 
 class LoginRestServlet(RestServlet):
@@ -142,8 +137,8 @@ class LoginRestServlet(RestServlet):
         # counters are initialised for the auth_provider_ids.
         _load_sso_handlers(hs)
 
-    def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
-        flows: List[JsonDict] = []
+    def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
+        flows: list[JsonDict] = []
         if self.jwt_enabled:
             flows.append({"type": LoginRestServlet.JWT_TYPE})
 
@@ -178,7 +173,7 @@ class LoginRestServlet(RestServlet):
         # fall back to the fallback API if they don't understand one of the
         # login flow types returned.
         if support_login_token_flow:
-            tokenTypeFlow: Dict[str, Any] = {"type": LoginRestServlet.TOKEN_TYPE}
+            tokenTypeFlow: dict[str, Any] = {"type": LoginRestServlet.TOKEN_TYPE}
             # If the login token flow is enabled advertise the get_login_token flag.
             if self._get_login_token_enabled:
                 tokenTypeFlow["get_login_token"] = True
@@ -190,7 +185,7 @@ class LoginRestServlet(RestServlet):
 
         return 200, {"flows": flows}
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, LoginResponse]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, LoginResponse]:
         login_submission = parse_json_object_from_request(request)
 
         # Check to see if the client requested a refresh token.
@@ -370,13 +365,13 @@ class LoginRestServlet(RestServlet):
         self,
         user_id: str,
         login_submission: JsonDict,
-        callback: Optional[Callable[[LoginResponse], Awaitable[None]]] = None,
+        callback: Callable[[LoginResponse], Awaitable[None]] | None = None,
         create_non_existent_users: bool = False,
-        default_display_name: Optional[str] = None,
+        default_display_name: str | None = None,
         ratelimit: bool = True,
-        auth_provider_id: Optional[str] = None,
+        auth_provider_id: str | None = None,
         should_issue_refresh_token: bool = False,
-        auth_provider_session_id: Optional[str] = None,
+        auth_provider_session_id: str | None = None,
         should_check_deactivated_or_locked: bool = True,
         *,
         request_info: RequestInfo,
@@ -602,7 +597,7 @@ class RefreshTokenServlet(RestServlet):
         )
         self.refresh_token_lifetime = hs.config.registration.refresh_token_lifetime
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         refresh_submission = parse_json_object_from_request(request)
 
         assert_params_in_dict(refresh_submission, ["refresh_token"])
@@ -626,7 +621,7 @@ class RefreshTokenServlet(RestServlet):
             token, access_valid_until_ms, refresh_valid_until_ms
         )
 
-        response: Dict[str, Union[str, int]] = {
+        response: dict[str, str | int] = {
             "access_token": access_token,
             "refresh_token": refresh_token,
         }
@@ -655,9 +650,7 @@ class SsoRedirectServlet(RestServlet):
         self._sso_handler = hs.get_sso_handler()
         self._public_baseurl = hs.config.server.public_baseurl
 
-    async def on_GET(
-        self, request: SynapseRequest, idp_id: Optional[str] = None
-    ) -> None:
+    async def on_GET(self, request: SynapseRequest, idp_id: str | None = None) -> None:
         if not self._public_baseurl:
             raise SynapseError(400, "SSO requires a valid public_baseurl")
 
@@ -684,7 +677,7 @@ class SsoRedirectServlet(RestServlet):
             finish_request(request)
             return
 
-        args: Dict[bytes, List[bytes]] = request.args  # type: ignore
+        args: dict[bytes, list[bytes]] = request.args  # type: ignore
         client_redirect_url = parse_bytes_from_args(args, "redirectUrl", required=True)
         sso_url = await self._sso_handler.handle_redirect_request(
             request,
diff --git a/synapse/rest/client/login_token_request.py b/synapse/rest/client/login_token_request.py
index a053db8e55..f455e9c0b7 100644
--- a/synapse/rest/client/login_token_request.py
+++ b/synapse/rest/client/login_token_request.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.ratelimiting import Ratelimiter
 from synapse.config.ratelimiting import RatelimitSettings
@@ -89,7 +89,7 @@ class LoginTokenRequestServlet(RestServlet):
         )
 
     @interactive_auth_handler
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         body = parse_json_object_from_request(request)
 
diff --git a/synapse/rest/client/logout.py b/synapse/rest/client/logout.py
index 39c62b9e26..d804552a4a 100644
--- a/synapse/rest/client/logout.py
+++ b/synapse/rest/client/logout.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.http.server import HttpServer
 from synapse.http.servlet import RestServlet
@@ -43,7 +43,7 @@ class LogoutRestServlet(RestServlet):
         self._auth_handler = hs.get_auth_handler()
         self._device_handler = hs.get_device_handler()
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(
             request, allow_expired=True, allow_locked=True
         )
@@ -70,7 +70,7 @@ class LogoutAllRestServlet(RestServlet):
         self._auth_handler = hs.get_auth_handler()
         self._device_handler = hs.get_device_handler()
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(
             request, allow_expired=True, allow_locked=True
         )
diff --git a/synapse/rest/client/matrixrtc.py b/synapse/rest/client/matrixrtc.py
new file mode 100644
index 0000000000..22f8498f2f
--- /dev/null
+++ b/synapse/rest/client/matrixrtc.py
@@ -0,0 +1,52 @@
+#
+# This file is licensed under the Affero General Public License (AGPL) version 3.
+#
+# Copyright (C) 2025 New Vector, Ltd
+#
+# This program is free software: you can redistribute it and/or modify
+# it under the terms of the GNU Affero General Public License as
+# published by the Free Software Foundation, either version 3 of the
+# License, or (at your option) any later version.
+#
+# See the GNU Affero General Public License for more details:
+# <https://www.gnu.org/licenses/agpl-3.0.html>.
+#
+# [This file includes modifications made by New Vector Limited]
+#
+#
+
+from typing import TYPE_CHECKING
+
+from synapse.http.server import HttpServer
+from synapse.http.servlet import RestServlet
+from synapse.http.site import SynapseRequest
+from synapse.rest.client._base import client_patterns
+from synapse.types import JsonDict
+
+if TYPE_CHECKING:
+    from synapse.server import HomeServer
+
+
+class MatrixRTCRestServlet(RestServlet):
+    PATTERNS = client_patterns(r"/org\.matrix\.msc4143/rtc/transports$", releases=())
+    CATEGORY = "Client API requests"
+
+    def __init__(self, hs: "HomeServer"):
+        super().__init__()
+        self._hs = hs
+        self._auth = hs.get_auth()
+        self._transports = hs.config.matrix_rtc.transports
+
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
+        # Require authentication for this endpoint.
+        await self._auth.get_user_by_req(request)
+
+        if self._transports:
+            return 200, {"rtc_transports": self._transports}
+
+        return 200, {}
+
+
+def register_servlets(hs: "HomeServer", http_server: HttpServer) -> None:
+    if hs.config.experimental.msc4143_enabled:
+        MatrixRTCRestServlet(hs).register(http_server)
diff --git a/synapse/rest/client/media.py b/synapse/rest/client/media.py
index 4c044ae900..f145b03af4 100644
--- a/synapse/rest/client/media.py
+++ b/synapse/rest/client/media.py
@@ -22,7 +22,6 @@
 
 import logging
 import re
-from typing import Optional
 
 from synapse.http.server import (
     HttpServer,
@@ -231,7 +230,7 @@ class DownloadResource(RestServlet):
         request: SynapseRequest,
         server_name: str,
         media_id: str,
-        file_name: Optional[str] = None,
+        file_name: str | None = None,
     ) -> None:
         # Validate the server name, raising if invalid
         parse_and_validate_server_name(server_name)
diff --git a/synapse/rest/client/mutual_rooms.py b/synapse/rest/client/mutual_rooms.py
index abb1fab0a3..bda6ed1f70 100644
--- a/synapse/rest/client/mutual_rooms.py
+++ b/synapse/rest/client/mutual_rooms.py
@@ -20,7 +20,7 @@
 #
 import logging
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Dict, List, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.errors import Codes, SynapseError
 from synapse.http.server import HttpServer
@@ -51,9 +51,9 @@ class UserMutualRoomsServlet(RestServlet):
         self.auth = hs.get_auth()
         self.store = hs.get_datastores().main
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
-        # twisted.web.server.Request.args is incorrectly defined as Optional[Any]
-        args: Dict[bytes, List[bytes]] = request.args  # type: ignore
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
+        # twisted.web.server.Request.args is incorrectly defined as Any | None
+        args: dict[bytes, list[bytes]] = request.args  # type: ignore
 
         user_ids = parse_strings_from_args(args, "user_id", required=True)
 
diff --git a/synapse/rest/client/notifications.py b/synapse/rest/client/notifications.py
index 168ce50d3f..2420e9fffb 100644
--- a/synapse/rest/client/notifications.py
+++ b/synapse/rest/client/notifications.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.constants import ReceiptTypes
 from synapse.events.utils import (
@@ -53,7 +53,7 @@ class NotificationsServlet(RestServlet):
         self.clock = hs.get_clock()
         self._event_serializer = hs.get_event_client_serializer()
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         user_id = requester.user.to_string()
 
diff --git a/synapse/rest/client/openid.py b/synapse/rest/client/openid.py
index a2c2faa199..e624a48ce7 100644
--- a/synapse/rest/client/openid.py
+++ b/synapse/rest/client/openid.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.errors import AuthError
 from synapse.http.server import HttpServer
@@ -80,7 +80,7 @@ class IdTokenServlet(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         if user_id != requester.user.to_string():
             raise AuthError(403, "Cannot request tokens for other users.")
diff --git a/synapse/rest/client/password_policy.py b/synapse/rest/client/password_policy.py
index 7ec6dd3443..314c409fc2 100644
--- a/synapse/rest/client/password_policy.py
+++ b/synapse/rest/client/password_policy.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from twisted.web.server import Request
 
@@ -46,7 +46,7 @@ class PasswordPolicyServlet(RestServlet):
         self.policy = hs.config.auth.password_policy
         self.enabled = hs.config.auth.password_policy_enabled
 
-    def on_GET(self, request: Request) -> Tuple[int, JsonDict]:
+    def on_GET(self, request: Request) -> tuple[int, JsonDict]:
         if not self.enabled or not self.policy:
             return 200, {}
 
diff --git a/synapse/rest/client/presence.py b/synapse/rest/client/presence.py
index 104d54cd89..de3ffdaa0b 100644
--- a/synapse/rest/client/presence.py
+++ b/synapse/rest/client/presence.py
@@ -22,7 +22,7 @@
 """This module contains REST servlets to do with presence: /presence/<paths>"""
 
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.errors import AuthError, Codes, LimitExceededError, SynapseError
 from synapse.api.ratelimiting import Ratelimiter
@@ -60,7 +60,7 @@ class PresenceStatusRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         user = UserID.from_string(user_id)
 
@@ -84,7 +84,7 @@ class PresenceStatusRestServlet(RestServlet):
 
     async def on_PUT(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         user = UserID.from_string(user_id)
 
diff --git a/synapse/rest/client/profile.py b/synapse/rest/client/profile.py
index 8bc532c811..7f3128cb61 100644
--- a/synapse/rest/client/profile.py
+++ b/synapse/rest/client/profile.py
@@ -23,7 +23,7 @@
 
 import re
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.constants import ProfileFields
 from synapse.api.errors import Codes, SynapseError
@@ -69,7 +69,7 @@ class ProfileRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester_user = None
 
         if self.hs.config.server.require_auth_for_profile_requests:
@@ -118,7 +118,7 @@ class ProfileFieldRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, user_id: str, field_name: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester_user = None
 
         if self.hs.config.server.require_auth_for_profile_requests:
@@ -156,7 +156,7 @@ class ProfileFieldRestServlet(RestServlet):
 
     async def on_PUT(
         self, request: SynapseRequest, user_id: str, field_name: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         if not UserID.is_valid(user_id):
             raise SynapseError(
                 HTTPStatus.BAD_REQUEST, "Invalid user id", Codes.INVALID_PARAM
@@ -221,7 +221,7 @@ class ProfileFieldRestServlet(RestServlet):
 
     async def on_DELETE(
         self, request: SynapseRequest, user_id: str, field_name: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         if not UserID.is_valid(user_id):
             raise SynapseError(
                 HTTPStatus.BAD_REQUEST, "Invalid user id", Codes.INVALID_PARAM
diff --git a/synapse/rest/client/push_rule.py b/synapse/rest/client/push_rule.py
index c1939a9b57..39b0cde47b 100644
--- a/synapse/rest/client/push_rule.py
+++ b/synapse/rest/client/push_rule.py
@@ -20,7 +20,7 @@
 #
 
 from http import HTTPStatus
-from typing import TYPE_CHECKING, List, Tuple, Union
+from typing import TYPE_CHECKING
 
 from synapse.api.errors import (
     Codes,
@@ -67,7 +67,7 @@ class PushRuleRestServlet(RestServlet):
         self._push_rules_handler = hs.get_push_rules_handler()
         self._push_rule_linearizer = Linearizer(name="push_rules", clock=hs.get_clock())
 
-    async def on_PUT(self, request: SynapseRequest, path: str) -> Tuple[int, JsonDict]:
+    async def on_PUT(self, request: SynapseRequest, path: str) -> tuple[int, JsonDict]:
         if not self._is_push_worker:
             raise Exception("Cannot handle PUT /push_rules on worker")
 
@@ -79,7 +79,7 @@ class PushRuleRestServlet(RestServlet):
 
     async def handle_put(
         self, request: SynapseRequest, path: str, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         spec = _rule_spec_from_path(path.split("/"))
         try:
             priority_class = _priority_class_from_spec(spec)
@@ -140,7 +140,7 @@ class PushRuleRestServlet(RestServlet):
 
     async def on_DELETE(
         self, request: SynapseRequest, path: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         if not self._is_push_worker:
             raise Exception("Cannot handle DELETE /push_rules on worker")
 
@@ -155,7 +155,7 @@ class PushRuleRestServlet(RestServlet):
         request: SynapseRequest,
         path: str,
         user_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         spec = _rule_spec_from_path(path.split("/"))
 
         namespaced_rule_id = f"global/{spec.template}/{spec.rule_id}"
@@ -170,7 +170,7 @@ class PushRuleRestServlet(RestServlet):
             else:
                 raise
 
-    async def on_GET(self, request: SynapseRequest, path: str) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest, path: str) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         requester.user.to_string()
 
@@ -196,7 +196,7 @@ class PushRuleRestServlet(RestServlet):
             raise UnrecognizedRequestError()
 
 
-def _rule_spec_from_path(path: List[str]) -> RuleSpec:
+def _rule_spec_from_path(path: list[str]) -> RuleSpec:
     """Turn a sequence of path components into a rule spec
 
     Args:
@@ -240,7 +240,7 @@ def _rule_spec_from_path(path: List[str]) -> RuleSpec:
 
 def _rule_tuple_from_request_object(
     rule_template: str, rule_id: str, req_obj: JsonDict
-) -> Tuple[List[JsonDict], List[Union[str, JsonDict]]]:
+) -> tuple[list[JsonDict], list[str | JsonDict]]:
     if rule_template == "postcontent":
         # postcontent is from MSC4306, which says that clients
         # cannot create their own postcontent rules right now.
@@ -279,7 +279,7 @@ def _rule_tuple_from_request_object(
     return conditions, actions
 
 
-def _filter_ruleset_with_path(ruleset: JsonDict, path: List[str]) -> JsonDict:
+def _filter_ruleset_with_path(ruleset: JsonDict, path: list[str]) -> JsonDict:
     if path == []:
         raise UnrecognizedRequestError(
             PushRuleRestServlet.SLIGHTLY_PEDANTIC_TRAILING_SLASH_ERROR
diff --git a/synapse/rest/client/pusher.py b/synapse/rest/client/pusher.py
index a455f95a26..66d7fec07e 100644
--- a/synapse/rest/client/pusher.py
+++ b/synapse/rest/client/pusher.py
@@ -21,7 +21,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.errors import Codes, SynapseError
 from synapse.http.server import HttpServer
@@ -52,7 +52,7 @@ class PushersRestServlet(RestServlet):
         self.auth = hs.get_auth()
         self._store = hs.get_datastores().main
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         user_id = requester.user.to_string()
 
@@ -85,7 +85,7 @@ class PushersSetRestServlet(RestServlet):
         self.pusher_pool = self.hs.get_pusherpool()
         self._store = hs.get_datastores().main
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         user_id = requester.user.to_string()
 
diff --git a/synapse/rest/client/read_marker.py b/synapse/rest/client/read_marker.py
index d3d3c7c41d..874e7487bf 100644
--- a/synapse/rest/client/read_marker.py
+++ b/synapse/rest/client/read_marker.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.constants import ReceiptTypes
 from synapse.http.server import HttpServer
@@ -56,7 +56,7 @@ class ReadMarkerRestServlet(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
 
         await self.presence_handler.bump_presence_active_time(
diff --git a/synapse/rest/client/receipts.py b/synapse/rest/client/receipts.py
index 4bf93f485c..d3a43537bb 100644
--- a/synapse/rest/client/receipts.py
+++ b/synapse/rest/client/receipts.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.constants import MAIN_TIMELINE, ReceiptTypes
 from synapse.api.errors import Codes, SynapseError
@@ -59,7 +59,7 @@ class ReceiptRestServlet(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, room_id: str, receipt_type: str, event_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
 
         if not RoomID.is_valid(room_id) or not event_id.startswith(EventID.SIGIL):
diff --git a/synapse/rest/client/register.py b/synapse/rest/client/register.py
index b42006e4ce..9503446b92 100644
--- a/synapse/rest/client/register.py
+++ b/synapse/rest/client/register.py
@@ -21,7 +21,7 @@
 #
 import logging
 import random
-from typing import TYPE_CHECKING, List, Optional, Tuple
+from typing import TYPE_CHECKING
 
 from twisted.web.server import Request
 
@@ -100,7 +100,7 @@ class EmailRegisterRequestTokenRestServlet(RestServlet):
                 template_text=self.config.email.email_already_in_use_template_text,
             )
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         if not self.hs.config.email.can_verify_email:
             logger.warning(
                 "Email registration has been disabled due to lack of email config"
@@ -183,7 +183,7 @@ class MsisdnRegisterRequestTokenRestServlet(RestServlet):
         self.server_name = hs.hostname
         self.identity_handler = hs.get_identity_handler()
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         body = parse_json_object_from_request(request)
 
         assert_params_in_dict(
@@ -352,7 +352,7 @@ class UsernameAvailabilityRestServlet(RestServlet):
             hs.config.registration.inhibit_user_in_use_error
         )
 
-    async def on_GET(self, request: Request) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: Request) -> tuple[int, JsonDict]:
         if not self.hs.config.registration.enable_registration:
             raise SynapseError(
                 403, "Registration has been disabled", errcode=Codes.FORBIDDEN
@@ -402,7 +402,7 @@ class RegistrationTokenValidityRestServlet(RestServlet):
             cfg=hs.config.ratelimiting.rc_registration_token_validity,
         )
 
-    async def on_GET(self, request: Request) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: Request) -> tuple[int, JsonDict]:
         await self.ratelimiter.ratelimit(None, (request.getClientAddress().host,))
 
         if not self.hs.config.registration.enable_registration:
@@ -453,7 +453,7 @@ class RegisterRestServlet(RestServlet):
         )
 
     @interactive_auth_handler
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         body = parse_json_object_from_request(request)
 
         client_addr = request.getClientAddress().host
@@ -852,8 +852,8 @@ class RegisterRestServlet(RestServlet):
         return result
 
     async def _do_guest_registration(
-        self, params: JsonDict, address: Optional[str] = None
-    ) -> Tuple[int, JsonDict]:
+        self, params: JsonDict, address: str | None = None
+    ) -> tuple[int, JsonDict]:
         if not self.hs.config.registration.allow_guest_access:
             raise SynapseError(403, "Guest access is disabled")
         user_id = await self.registration_handler.register_user(
@@ -913,7 +913,7 @@ class RegisterAppServiceOnlyRestServlet(RestServlet):
         self.ratelimiter = hs.get_registration_ratelimiter()
 
     @interactive_auth_handler
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         body = parse_json_object_from_request(request)
 
         client_addr = request.getClientAddress().host
@@ -970,7 +970,7 @@ class RegisterAppServiceOnlyRestServlet(RestServlet):
 
 def _calculate_registration_flows(
     config: HomeServerConfig, auth_handler: AuthHandler
-) -> List[List[str]]:
+) -> list[list[str]]:
     """Get a suitable flows list for registration
 
     Args:
diff --git a/synapse/rest/client/relations.py b/synapse/rest/client/relations.py
index 788f87602f..c0d7abcfd1 100644
--- a/synapse/rest/client/relations.py
+++ b/synapse/rest/client/relations.py
@@ -20,7 +20,7 @@
 
 import logging
 import re
-from typing import TYPE_CHECKING, Dict, Optional, Sequence, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.constants import Direction
 from synapse.api.errors import SynapseError
@@ -35,7 +35,8 @@ from synapse.streams.config import (
     PaginationConfig,
     extract_stream_token_from_pagination_token,
 )
-from synapse.types import JsonDict, RoomStreamToken, StreamToken
+from synapse.types import JsonDict, RoomStreamToken, StreamKeyType, StreamToken
+from synapse.types.rest.client import ThreadUpdatesBody
 
 if TYPE_CHECKING:
     from synapse.server import HomeServer
@@ -66,9 +67,9 @@ class RelationPaginationServlet(RestServlet):
         request: SynapseRequest,
         room_id: str,
         parent_id: str,
-        relation_type: Optional[str] = None,
-        event_type: Optional[str] = None,
-    ) -> Tuple[int, JsonDict]:
+        relation_type: str | None = None,
+        event_type: str | None = None,
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
 
         pagination_config = await PaginationConfig.from_request(
@@ -110,7 +111,7 @@ class ThreadsServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
 
         limit = parse_integer(request, "limit", default=5)
@@ -158,14 +159,17 @@ class ThreadUpdatesServlet(RestServlet):
         self.store = hs.get_datastores().main
         self.relations_handler = hs.get_relations_handler()
         self.event_serializer = hs.get_event_client_serializer()
+        self._storage_controllers = hs.get_storage_controllers()
+        # TODO: Get sliding sync handler for filter_rooms logic
+        # self.sliding_sync_handler = hs.get_sliding_sync_handler()
 
     async def _serialize_thread_updates(
         self,
-        thread_updates: Sequence[ThreadUpdateInfo],
-        bundled_aggregations: Dict[str, BundledAggregations],
+        thread_updates: list[ThreadUpdateInfo],
+        bundled_aggregations: dict[str, BundledAggregations],
         time_now: int,
         serialize_options: SerializeEventConfig,
-    ) -> Dict[str, Dict[str, JsonDict]]:
+    ) -> dict[str, dict[str, JsonDict]]:
         """
         Serialize thread updates into the response format.
 
@@ -178,7 +182,7 @@ class ThreadUpdatesServlet(RestServlet):
         Returns:
             Nested dict mapping room_id -> thread_root_id -> thread update dict
         """
-        chunk: Dict[str, Dict[str, JsonDict]] = {}
+        chunk: dict[str, dict[str, JsonDict]] = {}
 
         for update in thread_updates:
             room_id = update.room_id
@@ -215,10 +219,13 @@ class ThreadUpdatesServlet(RestServlet):
 
         return chunk
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
 
-        # Parse parameters
+        # Parse request body
+        body = ThreadUpdatesBody.model_validate_json(request.content.read())
+
+        # Parse query parameters
         dir_str = parse_string(request, "dir", default="b")
         if dir_str != "b":
             raise SynapseError(
@@ -234,8 +241,8 @@ class ThreadUpdatesServlet(RestServlet):
         to_token_str = parse_string(request, "to")
 
         # Parse pagination tokens
-        from_token: Optional[RoomStreamToken] = None
-        to_token: Optional[RoomStreamToken] = None
+        from_token: RoomStreamToken | None = None
+        to_token: RoomStreamToken | None = None
 
         if from_token_str:
             try:
@@ -261,58 +268,108 @@ class ThreadUpdatesServlet(RestServlet):
             except Exception:
                 raise SynapseError(400, "'to' parameter is invalid")
 
+        # Get the list of rooms to fetch thread updates for
+        # Start with all joined rooms, then apply filters if provided
+        user_id = requester.user.to_string()
+        room_ids = await self.store.get_rooms_for_user(user_id)
+
+        if body.filters is not None:
+            # TODO: Apply filters using sliding sync room filter logic
+            # For now, if filters are provided, we need to call the sliding sync
+            # filter_rooms method to get the applicable room IDs
+            raise SynapseError(501, "Room filters not yet implemented")
+
         # Fetch thread updates from storage
         # For backward pagination:
         # - 'from' (upper bound, exclusive) maps to 'to_token' (inclusive with <=)
         #   Since next_batch is (last_returned - 1), <= excludes the last returned item
         # - 'to' (lower bound, exclusive) maps to 'from_token' (exclusive with >)
-        thread_updates, next_token = await self.store.get_thread_updates_for_user(
-            user_id=requester.user.to_string(),
+        (
+            all_thread_updates,
+            prev_batch_token,
+        ) = await self.store.get_thread_updates_for_rooms(
+            room_ids=room_ids,
             from_token=to_token,
             to_token=from_token,
             limit=limit,
-            include_thread_roots=True,
         )
 
-        # Serialize response
-        chunk: Dict[str, Dict[str, JsonDict]] = {}
+        if len(all_thread_updates) == 0:
+            return 200, {"chunk": {}}
 
-        if thread_updates:
-            # Get bundled aggregations for all thread roots
-            thread_root_events = [
-                update.thread_root_event
-                for update in thread_updates
-                if update.thread_root_event is not None
-            ]
+        # Filter thread updates for visibility
+        filtered_updates = (
+            await self.relations_handler.process_thread_updates_for_visibility(
+                all_thread_updates, user_id
+            )
+        )
 
-            bundled_aggregations = {}
-            if thread_root_events:
-                bundled_aggregations = (
-                    await self.relations_handler.get_bundled_aggregations(
-                        thread_root_events, requester.user.to_string()
-                    )
+        if not filtered_updates:
+            return 200, {"chunk": {}}
+
+        # Fetch thread root events and their bundled aggregations
+        (
+            thread_root_event_map,
+            aggregations_map,
+        ) = await self.relations_handler.fetch_thread_roots_and_aggregations(
+            filtered_updates.keys(), user_id
+        )
+
+        # Build response with per-thread data
+        # Updates are already sorted by stream_ordering DESC from the database query,
+        # and filter_events_for_client preserves order, so updates[0] is guaranteed to be
+        # the latest event for each thread.
+        time_now = self.clock.time_msec()
+        serialize_options = SerializeEventConfig(requester=requester)
+        chunk: dict[str, dict[str, JsonDict]] = {}
+
+        for thread_root_id, updates in filtered_updates.items():
+            # We only care about the latest update for the thread
+            latest_update = updates[0]
+            room_id = latest_update.room_id
+
+            if room_id not in chunk:
+                chunk[room_id] = {}
+
+            update_dict: JsonDict = {}
+
+            # Add thread root if present
+            thread_root_event = thread_root_event_map.get(thread_root_id)
+            if thread_root_event is not None:
+                bundle_aggs_map = (
+                    {thread_root_id: aggregations_map[thread_root_id]}
+                    if thread_root_id in aggregations_map
+                    else None
+                )
+                serialized_events = await self.event_serializer.serialize_events(
+                    [thread_root_event],
+                    time_now,
+                    config=serialize_options,
+                    bundle_aggregations=bundle_aggs_map,
+                )
+                if serialized_events:
+                    update_dict["thread_root"] = serialized_events[0]
+
+            # Add per-thread prev_batch if this thread has multiple visible updates
+            if len(updates) > 1:
+                # Create a token pointing to one position before the latest event's stream position.
+                # This makes it exclusive - /relations with dir=b won't return the latest event again.
+                per_thread_prev_batch = StreamToken.START.copy_and_replace(
+                    StreamKeyType.ROOM,
+                    RoomStreamToken(stream=latest_update.stream_ordering - 1),
+                )
+                update_dict["prev_batch"] = await per_thread_prev_batch.to_string(
+                    self.store
                 )
 
-            # Set up serialization
-            time_now = self.clock.time_msec()
-            serialize_options = SerializeEventConfig(
-                requester=requester,
-            )
-
-            # Serialize all thread updates
-            chunk = await self._serialize_thread_updates(
-                thread_updates=thread_updates,
-                bundled_aggregations=bundled_aggregations,
-                time_now=time_now,
-                serialize_options=serialize_options,
-            )
+            chunk[room_id][thread_root_id] = update_dict
 
         # Build response
         response: JsonDict = {"chunk": chunk}
 
         # Add next_batch token for pagination
-        if next_token is not None:
-            response["next_batch"] = await next_token.to_string(self.store)
+        if prev_batch_token is not None:
+            response["next_batch"] = await prev_batch_token.to_string(self.store)
 
         return 200, response
 
diff --git a/synapse/rest/client/rendezvous.py b/synapse/rest/client/rendezvous.py
index a1808847f0..08a449eefc 100644
--- a/synapse/rest/client/rendezvous.py
+++ b/synapse/rest/client/rendezvous.py
@@ -21,7 +21,7 @@
 
 import logging
 from http.client import TEMPORARY_REDIRECT
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING
 
 from synapse.http.server import HttpServer, respond_with_redirect
 from synapse.http.servlet import RestServlet
@@ -41,7 +41,7 @@ class MSC4108DelegationRendezvousServlet(RestServlet):
 
     def __init__(self, hs: "HomeServer"):
         super().__init__()
-        redirection_target: Optional[str] = (
+        redirection_target: str | None = (
             hs.config.experimental.msc4108_delegation_endpoint
         )
         assert redirection_target is not None, (
diff --git a/synapse/rest/client/reporting.py b/synapse/rest/client/reporting.py
index 81faf38a7f..0c594b9f3f 100644
--- a/synapse/rest/client/reporting.py
+++ b/synapse/rest/client/reporting.py
@@ -21,9 +21,10 @@
 
 import logging
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
+
+from pydantic import StrictStr
 
-from synapse._pydantic_compat import StrictStr
 from synapse.api.errors import AuthError, Codes, NotFoundError, SynapseError
 from synapse.http.server import HttpServer
 from synapse.http.servlet import (
@@ -57,7 +58,7 @@ class ReportEventRestServlet(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, room_id: str, event_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         user_id = requester.user.to_string()
 
@@ -138,7 +139,7 @@ class ReportRoomRestServlet(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         user_id = requester.user.to_string()
 
@@ -191,7 +192,7 @@ class ReportUserRestServlet(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, target_user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         body = parse_and_validate_json_object_from_request(request, self.PostBody)
 
diff --git a/synapse/rest/client/room.py b/synapse/rest/client/room.py
index 64deae7650..81a6bd57fc 100644
--- a/synapse/rest/client/room.py
+++ b/synapse/rest/client/room.py
@@ -25,7 +25,7 @@ import logging
 import re
 from enum import Enum
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Awaitable, Dict, List, Optional, Tuple
+from typing import TYPE_CHECKING, Awaitable
 from urllib import parse as urlparse
 
 from prometheus_client.core import Histogram
@@ -66,7 +66,6 @@ from synapse.http.site import SynapseRequest
 from synapse.logging.context import make_deferred_yieldable, run_in_background
 from synapse.logging.opentracing import set_tag
 from synapse.metrics import SERVER_NAME_LABEL
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.rest.client._base import client_patterns
 from synapse.rest.client.transactions import HttpTransactionCache
 from synapse.state import CREATE_KEY, POWER_KEY
@@ -167,20 +166,20 @@ class RoomCreateRestServlet(TransactionRestServlet):
 
     async def on_PUT(
         self, request: SynapseRequest, txn_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         set_tag("txn_id", txn_id)
         return await self.txns.fetch_or_execute_request(
             request, requester, self._do, request, requester
         )
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         return await self._do(request, requester)
 
     async def _do(
         self, request: SynapseRequest, requester: Requester
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         room_id, _, _ = await self._room_creation_handler.create_room(
             requester, self.get_room_config(request)
         )
@@ -245,18 +244,18 @@ class RoomStateEventRestServlet(RestServlet):
     @cancellable
     def on_GET_no_state_key(
         self, request: SynapseRequest, room_id: str, event_type: str
-    ) -> Awaitable[Tuple[int, JsonDict]]:
+    ) -> Awaitable[tuple[int, JsonDict]]:
         return self.on_GET(request, room_id, event_type, "")
 
     def on_PUT_no_state_key(
         self, request: SynapseRequest, room_id: str, event_type: str
-    ) -> Awaitable[Tuple[int, JsonDict]]:
+    ) -> Awaitable[tuple[int, JsonDict]]:
         return self.on_PUT(request, room_id, event_type, "")
 
     @cancellable
     async def on_GET(
         self, request: SynapseRequest, room_id: str, event_type: str, state_key: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
         format = parse_string(
             request, "format", default="content", allowed_values=["content", "event"]
@@ -295,8 +294,8 @@ class RoomStateEventRestServlet(RestServlet):
         room_id: str,
         event_type: str,
         state_key: str,
-        txn_id: Optional[str] = None,
-    ) -> Tuple[int, JsonDict]:
+        txn_id: str | None = None,
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
 
         if txn_id:
@@ -408,8 +407,8 @@ class RoomSendEventRestServlet(TransactionRestServlet):
         requester: Requester,
         room_id: str,
         event_type: str,
-        txn_id: Optional[str],
-    ) -> Tuple[int, JsonDict]:
+        txn_id: str | None,
+    ) -> tuple[int, JsonDict]:
         content = parse_json_object_from_request(request)
 
         origin_server_ts = None
@@ -461,13 +460,13 @@ class RoomSendEventRestServlet(TransactionRestServlet):
         request: SynapseRequest,
         room_id: str,
         event_type: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
         return await self._do(request, requester, room_id, event_type, None)
 
     async def on_PUT(
         self, request: SynapseRequest, room_id: str, event_type: str, txn_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
         set_tag("txn_id", txn_id)
 
@@ -485,8 +484,8 @@ class RoomSendEventRestServlet(TransactionRestServlet):
 
 def _parse_request_delay(
     request: SynapseRequest,
-    max_delay: Optional[int],
-) -> Optional[int]:
+    max_delay: int | None,
+) -> int | None:
     """Parses from the request string the delay parameter for
         delayed event requests, and checks it for correctness.
 
@@ -545,12 +544,12 @@ class JoinRoomAliasServlet(ResolveRoomIdMixin, TransactionRestServlet):
         request: SynapseRequest,
         requester: Requester,
         room_identifier: str,
-        txn_id: Optional[str],
-    ) -> Tuple[int, JsonDict]:
+        txn_id: str | None,
+    ) -> tuple[int, JsonDict]:
         content = parse_json_object_from_request(request, allow_empty_body=True)
 
-        # twisted.web.server.Request.args is incorrectly defined as Optional[Any]
-        args: Dict[bytes, List[bytes]] = request.args  # type: ignore
+        # twisted.web.server.Request.args is incorrectly defined as Any | None
+        args: dict[bytes, list[bytes]] = request.args  # type: ignore
         # Prefer via over server_name (deprecated with MSC4156)
         remote_room_hosts = parse_strings_from_args(args, "via", required=False)
         if remote_room_hosts is None:
@@ -579,13 +578,13 @@ class JoinRoomAliasServlet(ResolveRoomIdMixin, TransactionRestServlet):
         self,
         request: SynapseRequest,
         room_identifier: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
         return await self._do(request, requester, room_identifier, None)
 
     async def on_PUT(
         self, request: SynapseRequest, room_identifier: str, txn_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
         set_tag("txn_id", txn_id)
 
@@ -604,7 +603,7 @@ class PublicRoomListRestServlet(RestServlet):
         self.hs = hs
         self.auth = hs.get_auth()
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         server = parse_string(request, "server")
 
         try:
@@ -624,7 +623,7 @@ class PublicRoomListRestServlet(RestServlet):
             if server:
                 raise e
 
-        limit: Optional[int] = parse_integer(request, "limit", 0)
+        limit: int | None = parse_integer(request, "limit", 0)
         since_token = parse_string(request, "since")
 
         if limit == 0:
@@ -653,13 +652,13 @@ class PublicRoomListRestServlet(RestServlet):
 
         return 200, data
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await self.auth.get_user_by_req(request, allow_guest=True)
 
         server = parse_string(request, "server")
         content = parse_json_object_from_request(request)
 
-        limit: Optional[int] = int(content.get("limit", 100))
+        limit: int | None = int(content.get("limit", 100))
         since_token = content.get("since", None)
         search_filter = content.get("filter", None)
 
@@ -727,7 +726,7 @@ class RoomMemberListRestServlet(RestServlet):
     @cancellable
     async def on_GET(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         # TODO support Pagination stream API (limit/tokens)
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
         handler = self.message_handler
@@ -781,7 +780,7 @@ class JoinedRoomMemberListRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
 
         users_with_profile = await self.message_handler.get_joined_members(
@@ -810,7 +809,7 @@ class RoomMessageListRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         processing_start_time = self.clock.time_msec()
         # Fire off and hope that we get a result by the end.
         #
@@ -871,7 +870,7 @@ class RoomStateRestServlet(RestServlet):
     @cancellable
     async def on_GET(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, List[JsonDict]]:
+    ) -> tuple[int, list[JsonDict]]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
         # Get all the current state for this room
         events = await self.message_handler.get_state_events(
@@ -894,7 +893,7 @@ class RoomInitialSyncRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
         pagination_config = await PaginationConfig.from_request(
             self.store, request, default_limit=10
@@ -926,7 +925,7 @@ class RoomEventServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, room_id: str, event_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
 
         include_unredacted_content = self.msc2815_enabled and (
@@ -1014,7 +1013,7 @@ class RoomEventContextServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, room_id: str, event_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
 
         limit = parse_integer(request, "limit", default=10)
@@ -1073,20 +1072,20 @@ class RoomForgetRestServlet(TransactionRestServlet):
         PATTERNS = "/rooms/(?P<room_id>[^/]*)/forget"
         register_txn_path(self, PATTERNS, http_server)
 
-    async def _do(self, requester: Requester, room_id: str) -> Tuple[int, JsonDict]:
+    async def _do(self, requester: Requester, room_id: str) -> tuple[int, JsonDict]:
         await self.room_member_handler.forget(user=requester.user, room_id=room_id)
 
         return 200, {}
 
     async def on_POST(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=False)
         return await self._do(requester, room_id)
 
     async def on_PUT(
         self, request: SynapseRequest, room_id: str, txn_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=False)
         set_tag("txn_id", txn_id)
 
@@ -1119,8 +1118,8 @@ class RoomMembershipRestServlet(TransactionRestServlet):
         requester: Requester,
         room_id: str,
         membership_action: str,
-        txn_id: Optional[str],
-    ) -> Tuple[int, JsonDict]:
+        txn_id: str | None,
+    ) -> tuple[int, JsonDict]:
         if requester.is_guest and membership_action not in {
             Membership.JOIN,
             Membership.LEAVE,
@@ -1197,13 +1196,13 @@ class RoomMembershipRestServlet(TransactionRestServlet):
         request: SynapseRequest,
         room_id: str,
         membership_action: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
         return await self._do(request, requester, room_id, membership_action, None)
 
     async def on_PUT(
         self, request: SynapseRequest, room_id: str, membership_action: str, txn_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
         set_tag("txn_id", txn_id)
 
@@ -1225,6 +1224,7 @@ class RoomRedactEventRestServlet(TransactionRestServlet):
     def __init__(self, hs: "HomeServer"):
         super().__init__(hs)
         self.server_name = hs.hostname
+        self.hs = hs
         self.event_creation_handler = hs.get_event_creation_handler()
         self.auth = hs.get_auth()
         self._store = hs.get_datastores().main
@@ -1241,8 +1241,8 @@ class RoomRedactEventRestServlet(TransactionRestServlet):
         requester: Requester,
         room_id: str,
         event_id: str,
-        txn_id: Optional[str],
-    ) -> Tuple[int, JsonDict]:
+        txn_id: str | None,
+    ) -> tuple[int, JsonDict]:
         content = parse_json_object_from_request(request)
 
         requester_suspended = await self._store.get_user_suspended_status(
@@ -1307,9 +1307,8 @@ class RoomRedactEventRestServlet(TransactionRestServlet):
                 )
 
                 if with_relations:
-                    run_as_background_process(
+                    self.hs.run_as_background_process(
                         "redact_related_events",
-                        self.server_name,
                         self._relation_handler.redact_events_related_to,
                         requester=requester,
                         event_id=event_id,
@@ -1329,13 +1328,13 @@ class RoomRedactEventRestServlet(TransactionRestServlet):
         request: SynapseRequest,
         room_id: str,
         event_id: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         return await self._do(request, requester, room_id, event_id, None)
 
     async def on_PUT(
         self, request: SynapseRequest, room_id: str, event_id: str, txn_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         set_tag("txn_id", txn_id)
 
@@ -1364,7 +1363,7 @@ class RoomTypingRestServlet(RestServlet):
 
     async def on_PUT(
         self, request: SynapseRequest, room_id: str, user_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
 
         if not self._is_typing_writer:
@@ -1420,7 +1419,7 @@ class RoomAliasListServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
 
         alias_list = await self.directory_handler.get_aliases_for_room(
@@ -1439,7 +1438,7 @@ class SearchRestServlet(RestServlet):
         self.search_handler = hs.get_search_handler()
         self.auth = hs.get_auth()
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
 
         content = parse_json_object_from_request(request)
@@ -1459,7 +1458,7 @@ class JoinedRoomsRestServlet(RestServlet):
         self.store = hs.get_datastores().main
         self.auth = hs.get_auth()
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
 
         room_ids = await self.store.get_rooms_for_user(requester.user.to_string())
@@ -1534,7 +1533,7 @@ class TimestampLookupRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self._auth.get_user_by_req(request)
         await self._auth.check_user_in_room_or_world_readable(room_id, requester)
 
@@ -1567,16 +1566,16 @@ class RoomHierarchyRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self._auth.get_user_by_req(request, allow_guest=True)
 
         max_depth = parse_integer(request, "max_depth")
         limit = parse_integer(request, "limit")
 
-        # twisted.web.server.Request.args is incorrectly defined as Optional[Any]
+        # twisted.web.server.Request.args is incorrectly defined as Any | None
         remote_room_hosts = None
         if self.msc4235_enabled:
-            args: Dict[bytes, List[bytes]] = request.args  # type: ignore
+            args: dict[bytes, list[bytes]] = request.args  # type: ignore
             via_param = parse_strings_from_args(
                 args, "org.matrix.msc4235.via", required=False
             )
@@ -1615,16 +1614,16 @@ class RoomSummaryRestServlet(ResolveRoomIdMixin, RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, room_identifier: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         try:
             requester = await self._auth.get_user_by_req(request, allow_guest=True)
-            requester_user_id: Optional[str] = requester.user.to_string()
+            requester_user_id: str | None = requester.user.to_string()
         except MissingClientTokenError:
             # auth is optional
             requester_user_id = None
 
-        # twisted.web.server.Request.args is incorrectly defined as Optional[Any]
-        args: Dict[bytes, List[bytes]] = request.args  # type: ignore
+        # twisted.web.server.Request.args is incorrectly defined as Any | None
+        args: dict[bytes, list[bytes]] = request.args  # type: ignore
         remote_room_hosts = parse_strings_from_args(args, "via", required=False)
         room_id, remote_room_hosts = await self.resolve_room_id(
             room_identifier,
diff --git a/synapse/rest/client/room_keys.py b/synapse/rest/client/room_keys.py
index 7be08ecb60..b7f7c68d8f 100644
--- a/synapse/rest/client/room_keys.py
+++ b/synapse/rest/client/room_keys.py
@@ -19,7 +19,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Optional, Tuple, cast
+from typing import TYPE_CHECKING, cast
 
 from synapse.api.errors import Codes, NotFoundError, SynapseError
 from synapse.http.server import HttpServer
@@ -51,8 +51,8 @@ class RoomKeysServlet(RestServlet):
         self.e2e_room_keys_handler = hs.get_e2e_room_keys_handler()
 
     async def on_PUT(
-        self, request: SynapseRequest, room_id: Optional[str], session_id: Optional[str]
-    ) -> Tuple[int, JsonDict]:
+        self, request: SynapseRequest, room_id: str | None, session_id: str | None
+    ) -> tuple[int, JsonDict]:
         """
         Uploads one or more encrypted E2E room keys for backup purposes.
         room_id: the ID of the room the keys are for (optional)
@@ -146,8 +146,8 @@ class RoomKeysServlet(RestServlet):
         return 200, ret
 
     async def on_GET(
-        self, request: SynapseRequest, room_id: Optional[str], session_id: Optional[str]
-    ) -> Tuple[int, JsonDict]:
+        self, request: SynapseRequest, room_id: str | None, session_id: str | None
+    ) -> tuple[int, JsonDict]:
         """
         Retrieves one or more encrypted E2E room keys for backup purposes.
         Symmetric with the PUT version of the API.
@@ -233,8 +233,8 @@ class RoomKeysServlet(RestServlet):
         return 200, room_keys
 
     async def on_DELETE(
-        self, request: SynapseRequest, room_id: Optional[str], session_id: Optional[str]
-    ) -> Tuple[int, JsonDict]:
+        self, request: SynapseRequest, room_id: str | None, session_id: str | None
+    ) -> tuple[int, JsonDict]:
         """
         Deletes one or more encrypted E2E room keys for a user for backup purposes.
 
@@ -267,7 +267,7 @@ class RoomKeysNewVersionServlet(RestServlet):
         self.auth = hs.get_auth()
         self.e2e_room_keys_handler = hs.get_e2e_room_keys_handler()
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         """
         Retrieve the version information about the most current backup version (if any)
 
@@ -293,7 +293,7 @@ class RoomKeysNewVersionServlet(RestServlet):
                 raise SynapseError(404, "No backup found", Codes.NOT_FOUND)
         return 200, info
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         """
         Create a new backup version for this user's room_keys with the given
         info.  The version is allocated by the server and returned to the user
@@ -345,7 +345,7 @@ class RoomKeysVersionServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, version: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         """
         Retrieve the version information about a given version of the user's
         room_keys backup.
@@ -374,7 +374,7 @@ class RoomKeysVersionServlet(RestServlet):
 
     async def on_DELETE(
         self, request: SynapseRequest, version: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         """
         Delete the information about a given version of the user's
         room_keys backup. Doesn't delete the actual room data.
@@ -391,7 +391,7 @@ class RoomKeysVersionServlet(RestServlet):
 
     async def on_PUT(
         self, request: SynapseRequest, version: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         """
         Update the information about a given version of the user's room_keys backup.
 
diff --git a/synapse/rest/client/room_upgrade_rest_servlet.py b/synapse/rest/client/room_upgrade_rest_servlet.py
index a9717781b0..1c87b86ecb 100644
--- a/synapse/rest/client/room_upgrade_rest_servlet.py
+++ b/synapse/rest/client/room_upgrade_rest_servlet.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.errors import Codes, ShadowBanError, SynapseError
 from synapse.api.room_versions import KNOWN_ROOM_VERSIONS
@@ -73,7 +73,7 @@ class RoomUpgradeRestServlet(RestServlet):
 
     async def on_POST(
         self, request: SynapseRequest, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self._auth.get_user_by_req(request)
 
         content = parse_json_object_from_request(request)
diff --git a/synapse/rest/client/sendtodevice.py b/synapse/rest/client/sendtodevice.py
index 2a67514560..597cb1fecc 100644
--- a/synapse/rest/client/sendtodevice.py
+++ b/synapse/rest/client/sendtodevice.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.http import servlet
 from synapse.http.server import HttpServer
@@ -53,7 +53,7 @@ class SendToDeviceRestServlet(servlet.RestServlet):
 
     async def on_PUT(
         self, request: SynapseRequest, message_type: str, txn_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request, allow_guest=True)
         set_tag("txn_id", txn_id)
         return await self.txns.fetch_or_execute_request(
@@ -70,7 +70,7 @@ class SendToDeviceRestServlet(servlet.RestServlet):
         request: SynapseRequest,
         requester: Requester,
         message_type: str,
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         content = parse_json_object_from_request(request)
         assert_params_in_dict(content, ("messages",))
 
diff --git a/synapse/rest/client/sync.py b/synapse/rest/client/sync.py
index 0ddd82d877..b02ac8e4e1 100644
--- a/synapse/rest/client/sync.py
+++ b/synapse/rest/client/sync.py
@@ -21,7 +21,7 @@
 import itertools
 import logging
 from collections import defaultdict
-from typing import TYPE_CHECKING, Any, Dict, List, Mapping, Optional, Tuple, Union
+from typing import TYPE_CHECKING, Any, Mapping
 
 import attr
 
@@ -128,6 +128,7 @@ class SyncRestServlet(RestServlet):
 
         self._json_filter_cache: LruCache[str, bool] = LruCache(
             max_size=1000,
+            clock=self.clock,
             cache_name="sync_valid_filter",
             server_name=self.server_name,
         )
@@ -139,7 +140,7 @@ class SyncRestServlet(RestServlet):
             cfg=hs.config.ratelimiting.rc_presence_per_user,
         )
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         # This will always be set by the time Twisted calls us.
         assert request.args is not None
 
@@ -190,7 +191,7 @@ class SyncRestServlet(RestServlet):
         # in the response cache once the set of ignored users has changed.
         # (We filter out ignored users from timeline events, so our sync response
         # is invalid once the set of ignored users changes.)
-        last_ignore_accdata_streampos: Optional[int] = None
+        last_ignore_accdata_streampos: int | None = None
         if not since:
             # No `since`, so this is an initial sync.
             last_ignore_accdata_streampos = await self.store.get_latest_stream_id_for_global_account_data_by_type_for_user(
@@ -365,9 +366,6 @@ class SyncRestServlet(RestServlet):
 
         # https://github.com/matrix-org/matrix-doc/blob/54255851f642f84a4f1aaf7bc063eebe3d76752b/proposals/2732-olm-fallback-keys.md
         # states that this field should always be included, as long as the server supports the feature.
-        response["org.matrix.msc2732.device_unused_fallback_key_types"] = (
-            sync_result.device_unused_fallback_key_types
-        )
         response["device_unused_fallback_key_types"] = (
             sync_result.device_unused_fallback_key_types
         )
@@ -384,7 +382,7 @@ class SyncRestServlet(RestServlet):
         return response
 
     @staticmethod
-    def encode_presence(events: List[UserPresenceState], time_now: int) -> JsonDict:
+    def encode_presence(events: list[UserPresenceState], time_now: int) -> JsonDict:
         return {
             "events": [
                 {
@@ -402,7 +400,7 @@ class SyncRestServlet(RestServlet):
     async def encode_joined(
         self,
         sync_config: SyncConfig,
-        rooms: List[JoinedSyncResult],
+        rooms: list[JoinedSyncResult],
         time_now: int,
         serialize_options: SerializeEventConfig,
     ) -> JsonDict:
@@ -432,7 +430,7 @@ class SyncRestServlet(RestServlet):
     @trace_with_opname("sync.encode_invited")
     async def encode_invited(
         self,
-        rooms: List[InvitedSyncResult],
+        rooms: list[InvitedSyncResult],
         time_now: int,
         serialize_options: SerializeEventConfig,
     ) -> JsonDict:
@@ -468,10 +466,10 @@ class SyncRestServlet(RestServlet):
     @trace_with_opname("sync.encode_knocked")
     async def encode_knocked(
         self,
-        rooms: List[KnockedSyncResult],
+        rooms: list[KnockedSyncResult],
         time_now: int,
         serialize_options: SerializeEventConfig,
-    ) -> Dict[str, Dict[str, Any]]:
+    ) -> dict[str, dict[str, Any]]:
         """
         Encode the rooms we've knocked on in a sync result.
 
@@ -521,7 +519,7 @@ class SyncRestServlet(RestServlet):
     async def encode_archived(
         self,
         sync_config: SyncConfig,
-        rooms: List[ArchivedSyncResult],
+        rooms: list[ArchivedSyncResult],
         time_now: int,
         serialize_options: SerializeEventConfig,
     ) -> JsonDict:
@@ -551,7 +549,7 @@ class SyncRestServlet(RestServlet):
     async def encode_room(
         self,
         sync_config: SyncConfig,
-        room: Union[JoinedSyncResult, ArchivedSyncResult],
+        room: JoinedSyncResult | ArchivedSyncResult,
         time_now: int,
         joined: bool,
         serialize_options: SerializeEventConfig,
@@ -773,7 +771,7 @@ class SlidingSyncRestServlet(RestServlet):
         self.sliding_sync_handler = hs.get_sliding_sync_handler()
         self.event_serializer = hs.get_event_client_serializer()
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req_experimental_feature(
             request, allow_guest=True, feature=ExperimentalFeature.MSC3575
         )
@@ -909,7 +907,7 @@ class SlidingSyncRestServlet(RestServlet):
     async def encode_rooms(
         self,
         requester: Requester,
-        rooms: Dict[str, SlidingSyncResult.RoomResult],
+        rooms: dict[str, SlidingSyncResult.RoomResult],
         time_now: int,
     ) -> JsonDict:
         serialize_options = SerializeEventConfig(
@@ -917,7 +915,7 @@ class SlidingSyncRestServlet(RestServlet):
             requester=requester,
         )
 
-        serialized_rooms: Dict[str, JsonDict] = {}
+        serialized_rooms: dict[str, JsonDict] = {}
         for room_id, room_result in rooms.items():
             serialized_rooms[room_id] = {
                 "notification_count": room_result.notification_count,
diff --git a/synapse/rest/client/tags.py b/synapse/rest/client/tags.py
index fb59efb11f..5699ff35c7 100644
--- a/synapse/rest/client/tags.py
+++ b/synapse/rest/client/tags.py
@@ -21,7 +21,7 @@
 
 import logging
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.errors import AuthError, Codes, SynapseError
 from synapse.http.server import HttpServer
@@ -56,7 +56,7 @@ class TagListServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, user_id: str, room_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         if user_id != requester.user.to_string():
             raise AuthError(403, "Cannot get tags for other users.")
@@ -85,7 +85,7 @@ class TagServlet(RestServlet):
 
     async def on_PUT(
         self, request: SynapseRequest, user_id: str, room_id: str, tag: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         if user_id != requester.user.to_string():
             raise AuthError(403, "Cannot add tags for other users.")
@@ -114,7 +114,7 @@ class TagServlet(RestServlet):
 
     async def on_DELETE(
         self, request: SynapseRequest, user_id: str, room_id: str, tag: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
         if user_id != requester.user.to_string():
             raise AuthError(403, "Cannot add tags for other users.")
diff --git a/synapse/rest/client/thirdparty.py b/synapse/rest/client/thirdparty.py
index f972591ebf..c17335eb48 100644
--- a/synapse/rest/client/thirdparty.py
+++ b/synapse/rest/client/thirdparty.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Dict, List, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.constants import ThirdPartyEntityKind
 from synapse.http.server import HttpServer
@@ -45,7 +45,7 @@ class ThirdPartyProtocolsServlet(RestServlet):
         self.auth = hs.get_auth()
         self.appservice_handler = hs.get_application_service_handler()
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await self.auth.get_user_by_req(request, allow_guest=True)
 
         protocols = await self.appservice_handler.get_3pe_protocols()
@@ -63,7 +63,7 @@ class ThirdPartyProtocolServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, protocol: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await self.auth.get_user_by_req(request, allow_guest=True)
 
         protocols = await self.appservice_handler.get_3pe_protocols(
@@ -86,10 +86,10 @@ class ThirdPartyUserServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, protocol: str
-    ) -> Tuple[int, List[JsonDict]]:
+    ) -> tuple[int, list[JsonDict]]:
         await self.auth.get_user_by_req(request, allow_guest=True)
 
-        fields: Dict[bytes, List[bytes]] = request.args  # type: ignore[assignment]
+        fields: dict[bytes, list[bytes]] = request.args  # type: ignore[assignment]
         fields.pop(b"access_token", None)
 
         results = await self.appservice_handler.query_3pe(
@@ -110,10 +110,10 @@ class ThirdPartyLocationServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, protocol: str
-    ) -> Tuple[int, List[JsonDict]]:
+    ) -> tuple[int, list[JsonDict]]:
         await self.auth.get_user_by_req(request, allow_guest=True)
 
-        fields: Dict[bytes, List[bytes]] = request.args  # type: ignore[assignment]
+        fields: dict[bytes, list[bytes]] = request.args  # type: ignore[assignment]
         fields.pop(b"access_token", None)
 
         results = await self.appservice_handler.query_3pe(
diff --git a/synapse/rest/client/thread_subscriptions.py b/synapse/rest/client/thread_subscriptions.py
index 039aba1721..60676a4032 100644
--- a/synapse/rest/client/thread_subscriptions.py
+++ b/synapse/rest/client/thread_subscriptions.py
@@ -1,5 +1,5 @@
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Dict, Optional, Tuple
+from typing import TYPE_CHECKING
 
 import attr
 from typing_extensions import TypeAlias
@@ -50,7 +50,7 @@ class ThreadSubscriptionsRestServlet(RestServlet):
         self.handler = hs.get_thread_subscriptions_handler()
 
     class PutBody(RequestBodyModel):
-        automatic: Optional[AnyEventId]
+        automatic: AnyEventId | None = None
         """
         If supplied, the event ID of an event giving rise to this automatic subscription.
 
@@ -59,7 +59,7 @@ class ThreadSubscriptionsRestServlet(RestServlet):
 
     async def on_GET(
         self, request: SynapseRequest, room_id: str, thread_root_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         RoomID.from_string(room_id)
         if not thread_root_id.startswith("$"):
             raise SynapseError(
@@ -80,7 +80,7 @@ class ThreadSubscriptionsRestServlet(RestServlet):
 
     async def on_PUT(
         self, request: SynapseRequest, room_id: str, thread_root_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         RoomID.from_string(room_id)
         if not thread_root_id.startswith("$"):
             raise SynapseError(
@@ -101,7 +101,7 @@ class ThreadSubscriptionsRestServlet(RestServlet):
 
     async def on_DELETE(
         self, request: SynapseRequest, room_id: str, thread_root_id: str
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         RoomID.from_string(room_id)
         if not thread_root_id.startswith("$"):
             raise SynapseError(
@@ -134,7 +134,7 @@ class ThreadSubscriptionsPaginationRestServlet(RestServlet):
         self.is_mine = hs.is_mine
         self.store = hs.get_datastores().main
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(request)
 
         limit = min(
@@ -204,8 +204,8 @@ class ThreadSubscriptionsPaginationRestServlet(RestServlet):
             )
         )
 
-        subscribed_threads: Dict[str, Dict[str, JsonDict]] = {}
-        unsubscribed_threads: Dict[str, Dict[str, JsonDict]] = {}
+        subscribed_threads: dict[str, dict[str, JsonDict]] = {}
+        unsubscribed_threads: dict[str, dict[str, JsonDict]] = {}
         for stream_id, room_id, thread_root_id, subscribed, automatic in subscriptions:
             if subscribed:
                 subscribed_threads.setdefault(room_id, {})[thread_root_id] = (
diff --git a/synapse/rest/client/transactions.py b/synapse/rest/client/transactions.py
index 1a57996aec..4b3656a597 100644
--- a/synapse/rest/client/transactions.py
+++ b/synapse/rest/client/transactions.py
@@ -23,7 +23,7 @@
 to ensure idempotency when performing PUTs using the REST API."""
 
 import logging
-from typing import TYPE_CHECKING, Awaitable, Callable, Dict, Hashable, Tuple
+from typing import TYPE_CHECKING, Awaitable, Callable, Hashable
 
 from typing_extensions import ParamSpec
 
@@ -51,12 +51,12 @@ class HttpTransactionCache:
         self.hs = hs
         self.clock = self.hs.get_clock()
         # $txn_key: (ObservableDeferred<(res_code, res_json_body)>, timestamp)
-        self.transactions: Dict[
-            Hashable, Tuple[ObservableDeferred[Tuple[int, JsonDict]], int]
+        self.transactions: dict[
+            Hashable, tuple[ObservableDeferred[tuple[int, JsonDict]], int]
         ] = {}
         # Try to clean entries every 30 mins. This means entries will exist
         # for at *LEAST* 30 mins, and at *MOST* 60 mins.
-        self.cleaner = self.clock.looping_call(self._cleanup, CLEANUP_PERIOD_MS)
+        self.clock.looping_call(self._cleanup, CLEANUP_PERIOD_MS)
 
     def _get_transaction_key(self, request: IRequest, requester: Requester) -> Hashable:
         """A helper function which returns a transaction key that can be used
@@ -103,10 +103,10 @@ class HttpTransactionCache:
         self,
         request: IRequest,
         requester: Requester,
-        fn: Callable[P, Awaitable[Tuple[int, JsonDict]]],
+        fn: Callable[P, Awaitable[tuple[int, JsonDict]]],
         *args: P.args,
         **kwargs: P.kwargs,
-    ) -> "Deferred[Tuple[int, JsonDict]]":
+    ) -> "Deferred[tuple[int, JsonDict]]":
         """Fetches the response for this transaction, or executes the given function
         to produce a response for this transaction.
 
diff --git a/synapse/rest/client/user_directory.py b/synapse/rest/client/user_directory.py
index 94fcb11c0c..0f561c2e61 100644
--- a/synapse/rest/client/user_directory.py
+++ b/synapse/rest/client/user_directory.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.errors import SynapseError
 from synapse.http.server import HttpServer
@@ -46,7 +46,7 @@ class UserDirectorySearchRestServlet(RestServlet):
         self.auth = hs.get_auth()
         self.user_directory_handler = hs.get_user_directory_handler()
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonMapping]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonMapping]:
         """Searches for users in directory
 
         Returns:
diff --git a/synapse/rest/client/versions.py b/synapse/rest/client/versions.py
index 20395430d7..dee2cdb637 100644
--- a/synapse/rest/client/versions.py
+++ b/synapse/rest/client/versions.py
@@ -23,7 +23,7 @@
 
 import logging
 import re
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.constants import RoomCreationPreset
 from synapse.http.server import HttpServer
@@ -62,7 +62,7 @@ class VersionsRestServlet(RestServlet):
             in self.config.room.encryption_enabled_by_default_for_room_presets
         )
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         msc3881_enabled = self.config.experimental.msc3881_enabled
         msc3575_enabled = self.config.experimental.msc3575_enabled
 
diff --git a/synapse/rest/client/voip.py b/synapse/rest/client/voip.py
index fbed3a3bae..581829a790 100644
--- a/synapse/rest/client/voip.py
+++ b/synapse/rest/client/voip.py
@@ -22,7 +22,7 @@
 import base64
 import hashlib
 import hmac
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.http.server import HttpServer
 from synapse.http.servlet import RestServlet
@@ -43,7 +43,7 @@ class VoipRestServlet(RestServlet):
         self.hs = hs
         self.auth = hs.get_auth()
 
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         requester = await self.auth.get_user_by_req(
             request, self.hs.config.voip.turn_allow_guests
         )
diff --git a/synapse/rest/consent/consent_resource.py b/synapse/rest/consent/consent_resource.py
index 3961f82894..a1d2364bed 100644
--- a/synapse/rest/consent/consent_resource.py
+++ b/synapse/rest/consent/consent_resource.py
@@ -23,7 +23,7 @@ import logging
 from hashlib import sha256
 from http import HTTPStatus
 from os import path
-from typing import TYPE_CHECKING, Any, Dict, List
+from typing import TYPE_CHECKING, Any
 
 import jinja2
 from jinja2 import TemplateNotFound
@@ -121,7 +121,7 @@ class ConsentResource(DirectServeHtmlResource):
         has_consented = False
         public_version = username == ""
         if not public_version:
-            args: Dict[bytes, List[bytes]] = request.args  # type: ignore
+            args: dict[bytes, list[bytes]] = request.args  # type: ignore
             userhmac_bytes = parse_bytes_from_args(args, "h", required=True)
 
             self._check_hash(username, userhmac_bytes)
@@ -154,7 +154,7 @@ class ConsentResource(DirectServeHtmlResource):
     async def _async_render_POST(self, request: Request) -> None:
         version = parse_string(request, "v", required=True)
         username = parse_string(request, "u", required=True)
-        args: Dict[bytes, List[bytes]] = request.args  # type: ignore
+        args: dict[bytes, list[bytes]] = request.args  # type: ignore
         userhmac = parse_bytes_from_args(args, "h", required=True)
 
         self._check_hash(username, userhmac)
diff --git a/synapse/rest/key/v2/local_key_resource.py b/synapse/rest/key/v2/local_key_resource.py
index 608da25a6c..41e49ac384 100644
--- a/synapse/rest/key/v2/local_key_resource.py
+++ b/synapse/rest/key/v2/local_key_resource.py
@@ -21,7 +21,7 @@
 
 import logging
 import re
-from typing import TYPE_CHECKING, Optional, Tuple
+from typing import TYPE_CHECKING
 
 from signedjson.sign import sign_json
 from unpaddedbase64 import encode_base64
@@ -107,8 +107,8 @@ class LocalKey(RestServlet):
         return json_object
 
     def on_GET(
-        self, request: Request, key_id: Optional[str] = None
-    ) -> Tuple[int, JsonDict]:
+        self, request: Request, key_id: str | None = None
+    ) -> tuple[int, JsonDict]:
         # Matrix 1.6 drops support for passing the key_id, this is incompatible
         # with earlier versions and is allowed in order to support both.
         # A warning is issued to help determine when it is safe to drop this.
diff --git a/synapse/rest/key/v2/remote_key_resource.py b/synapse/rest/key/v2/remote_key_resource.py
index 94c679b9e7..c3dc69889b 100644
--- a/synapse/rest/key/v2/remote_key_resource.py
+++ b/synapse/rest/key/v2/remote_key_resource.py
@@ -21,13 +21,13 @@
 
 import logging
 import re
-from typing import TYPE_CHECKING, Dict, Mapping, Optional, Set, Tuple
+from typing import TYPE_CHECKING, Mapping
 
+from pydantic import ConfigDict, StrictInt, StrictStr
 from signedjson.sign import sign_json
 
 from twisted.web.server import Request
 
-from synapse._pydantic_compat import Extra, StrictInt, StrictStr
 from synapse.crypto.keyring import ServerKeyFetcher
 from synapse.http.server import HttpServer
 from synapse.http.servlet import (
@@ -48,10 +48,9 @@ logger = logging.getLogger(__name__)
 
 
 class _KeyQueryCriteriaDataModel(RequestBodyModel):
-    class Config:
-        extra = Extra.allow
+    model_config = ConfigDict(extra="allow")
 
-    minimum_valid_until_ts: Optional[StrictInt]
+    minimum_valid_until_ts: StrictInt | None
 
 
 class RemoteKey(RestServlet):
@@ -113,7 +112,7 @@ class RemoteKey(RestServlet):
     CATEGORY = "Federation requests"
 
     class PostBody(RequestBodyModel):
-        server_keys: Dict[StrictStr, Dict[StrictStr, _KeyQueryCriteriaDataModel]]
+        server_keys: dict[StrictStr, dict[StrictStr, _KeyQueryCriteriaDataModel]]
 
     def __init__(self, hs: "HomeServer"):
         self.fetcher = ServerKeyFetcher(hs)
@@ -143,8 +142,8 @@ class RemoteKey(RestServlet):
         )
 
     async def on_GET(
-        self, request: Request, server: str, key_id: Optional[str] = None
-    ) -> Tuple[int, JsonDict]:
+        self, request: Request, server: str, key_id: str | None = None
+    ) -> tuple[int, JsonDict]:
         if server and key_id:
             # Matrix 1.6 drops support for passing the key_id, this is incompatible
             # with earlier versions and is allowed in order to support both.
@@ -168,7 +167,7 @@ class RemoteKey(RestServlet):
 
         return 200, await self.query_keys(query, query_remote_on_cache_miss=True)
 
-    async def on_POST(self, request: Request) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: Request) -> tuple[int, JsonDict]:
         content = parse_and_validate_json_object_from_request(request, self.PostBody)
 
         query = content.server_keys
@@ -177,16 +176,16 @@ class RemoteKey(RestServlet):
 
     async def query_keys(
         self,
-        query: Dict[str, Dict[str, _KeyQueryCriteriaDataModel]],
+        query: dict[str, dict[str, _KeyQueryCriteriaDataModel]],
         query_remote_on_cache_miss: bool = False,
     ) -> JsonDict:
         logger.info("Handling query for keys %r", query)
 
-        server_keys: Dict[Tuple[str, str], Optional[FetchKeyResultForRemote]] = {}
+        server_keys: dict[tuple[str, str], FetchKeyResultForRemote | None] = {}
         for server_name, key_ids in query.items():
             if key_ids:
                 results: Mapping[
-                    str, Optional[FetchKeyResultForRemote]
+                    str, FetchKeyResultForRemote | None
                 ] = await self.store.get_server_keys_json_for_remote(
                     server_name, key_ids
                 )
@@ -199,13 +198,13 @@ class RemoteKey(RestServlet):
                 ((server_name, key_id), res) for key_id, res in results.items()
             )
 
-        json_results: Set[bytes] = set()
+        json_results: set[bytes] = set()
 
         time_now_ms = self.clock.time_msec()
 
         # Map server_name->key_id->int. Note that the value of the int is unused.
         # XXX: why don't we just use a set?
-        cache_misses: Dict[str, Dict[str, int]] = {}
+        cache_misses: dict[str, dict[str, int]] = {}
         for (server_name, key_id), key_result in server_keys.items():
             if not query[server_name]:
                 # all keys were requested. Just return what we have without worrying
diff --git a/synapse/rest/media/download_resource.py b/synapse/rest/media/download_resource.py
index 3c3f703667..f4569cfc7e 100644
--- a/synapse/rest/media/download_resource.py
+++ b/synapse/rest/media/download_resource.py
@@ -21,7 +21,7 @@
 #
 import logging
 import re
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING
 
 from synapse.http.server import set_corp_headers, set_cors_headers
 from synapse.http.servlet import RestServlet, parse_boolean, parse_integer
@@ -57,7 +57,7 @@ class DownloadResource(RestServlet):
         request: SynapseRequest,
         server_name: str,
         media_id: str,
-        file_name: Optional[str] = None,
+        file_name: str | None = None,
     ) -> None:
         # Validate the server name, raising if invalid
         parse_and_validate_server_name(server_name)
diff --git a/synapse/rest/media/upload_resource.py b/synapse/rest/media/upload_resource.py
index 74d8280582..56bc727cf8 100644
--- a/synapse/rest/media/upload_resource.py
+++ b/synapse/rest/media/upload_resource.py
@@ -22,7 +22,7 @@
 
 import logging
 import re
-from typing import IO, TYPE_CHECKING, Dict, List, Optional, Tuple
+from typing import IO, TYPE_CHECKING
 
 from synapse.api.errors import Codes, SynapseError
 from synapse.http.server import respond_with_json
@@ -56,7 +56,7 @@ class BaseUploadServlet(RestServlet):
 
     async def _get_file_metadata(
         self, request: SynapseRequest, user_id: str
-    ) -> Tuple[int, Optional[str], str]:
+    ) -> tuple[int, str | None, str]:
         raw_content_length = request.getHeader("Content-Length")
         if raw_content_length is None:
             raise SynapseError(msg="Request must specify a Content-Length", code=400)
@@ -78,11 +78,11 @@ class BaseUploadServlet(RestServlet):
                 code=413,
                 errcode=Codes.TOO_LARGE,
             )
-        args: Dict[bytes, List[bytes]] = request.args  # type: ignore
+        args: dict[bytes, list[bytes]] = request.args  # type: ignore
         upload_name_bytes = parse_bytes_from_args(args, "filename")
         if upload_name_bytes:
             try:
-                upload_name: Optional[str] = upload_name_bytes.decode("utf8")
+                upload_name: str | None = upload_name_bytes.decode("utf8")
             except UnicodeDecodeError:
                 raise SynapseError(
                     msg="Invalid UTF-8 filename parameter: %r" % (upload_name_bytes,),
diff --git a/synapse/rest/synapse/client/federation_whitelist.py b/synapse/rest/synapse/client/federation_whitelist.py
index f59daf8428..0382fef1e2 100644
--- a/synapse/rest/synapse/client/federation_whitelist.py
+++ b/synapse/rest/synapse/client/federation_whitelist.py
@@ -13,7 +13,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.http.server import DirectServeJsonResource
 from synapse.http.site import SynapseRequest
@@ -50,7 +50,7 @@ class FederationWhitelistResource(DirectServeJsonResource):
 
         self._auth = hs.get_auth()
 
-    async def _async_render_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def _async_render_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await self._auth.get_user_by_req(request)
 
         whitelist = []
diff --git a/synapse/rest/synapse/client/jwks.py b/synapse/rest/synapse/client/jwks.py
index e9a7c24e3b..15ff6f47c1 100644
--- a/synapse/rest/synapse/client/jwks.py
+++ b/synapse/rest/synapse/client/jwks.py
@@ -19,7 +19,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.http.server import DirectServeJsonResource
 from synapse.http.site import SynapseRequest
@@ -73,5 +73,5 @@ class JwksResource(DirectServeJsonResource):
             "keys": keys,
         }
 
-    async def _async_render_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def _async_render_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         return 200, self.res
diff --git a/synapse/rest/synapse/client/password_reset.py b/synapse/rest/synapse/client/password_reset.py
index 377578ef8a..1ccdf23da8 100644
--- a/synapse/rest/synapse/client/password_reset.py
+++ b/synapse/rest/synapse/client/password_reset.py
@@ -19,7 +19,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, Tuple
+from typing import TYPE_CHECKING
 
 from twisted.web.server import Request
 
@@ -65,7 +65,7 @@ class PasswordResetSubmitTokenResource(DirectServeHtmlResource):
         # This resource should only be mounted if email validation is enabled
         assert hs.config.email.can_verify_email
 
-    async def _async_render_GET(self, request: Request) -> Tuple[int, bytes]:
+    async def _async_render_GET(self, request: Request) -> tuple[int, bytes]:
         sid = parse_string(request, "sid", required=True)
         token = parse_string(request, "token", required=True)
         client_secret = parse_string(request, "client_secret", required=True)
@@ -83,7 +83,7 @@ class PasswordResetSubmitTokenResource(DirectServeHtmlResource):
             self._confirmation_email_template.render(**template_vars).encode("utf-8"),
         )
 
-    async def _async_render_POST(self, request: Request) -> Tuple[int, bytes]:
+    async def _async_render_POST(self, request: Request) -> tuple[int, bytes]:
         sid = parse_string(request, "sid", required=True)
         token = parse_string(request, "token", required=True)
         client_secret = parse_string(request, "client_secret", required=True)
diff --git a/synapse/rest/synapse/client/pick_username.py b/synapse/rest/synapse/client/pick_username.py
index 1727bb63b7..867ea1866d 100644
--- a/synapse/rest/synapse/client/pick_username.py
+++ b/synapse/rest/synapse/client/pick_username.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Generator, List, Tuple
+from typing import TYPE_CHECKING, Generator
 
 from twisted.web.resource import Resource
 from twisted.web.server import Request
@@ -65,7 +65,7 @@ class AvailabilityCheckResource(DirectServeJsonResource):
         super().__init__(clock=hs.get_clock())
         self._sso_handler = hs.get_sso_handler()
 
-    async def _async_render_GET(self, request: Request) -> Tuple[int, JsonDict]:
+    async def _async_render_GET(self, request: Request) -> tuple[int, JsonDict]:
         localpart = parse_string(request, "username", required=True)
 
         session_id = get_username_mapping_session_cookie_from_request(request)
@@ -138,7 +138,7 @@ class AccountDetailsResource(DirectServeHtmlResource):
             use_avatar = parse_boolean(request, "use_avatar", default=False)
 
             try:
-                emails_to_use: List[str] = [
+                emails_to_use: list[str] = [
                     val.decode("utf-8") for val in request.args.get(b"use_email", [])
                 ]
             except ValueError:
diff --git a/synapse/rest/synapse/client/rendezvous.py b/synapse/rest/synapse/client/rendezvous.py
index 5278c35572..24c10dee82 100644
--- a/synapse/rest/synapse/client/rendezvous.py
+++ b/synapse/rest/synapse/client/rendezvous.py
@@ -14,7 +14,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, List
+from typing import TYPE_CHECKING
 
 from synapse.api.errors import UnrecognizedRequestError
 from synapse.http.server import DirectServeJsonResource
@@ -34,7 +34,7 @@ class MSC4108RendezvousSessionResource(DirectServeJsonResource):
         self._handler = hs.get_rendezvous_handler()
 
     async def _async_render_GET(self, request: SynapseRequest) -> None:
-        postpath: List[bytes] = request.postpath  # type: ignore
+        postpath: list[bytes] = request.postpath  # type: ignore
         if len(postpath) != 1:
             raise UnrecognizedRequestError()
         session_id = postpath[0].decode("ascii")
@@ -42,7 +42,7 @@ class MSC4108RendezvousSessionResource(DirectServeJsonResource):
         self._handler.handle_get(request, session_id)
 
     def _async_render_PUT(self, request: SynapseRequest) -> None:
-        postpath: List[bytes] = request.postpath  # type: ignore
+        postpath: list[bytes] = request.postpath  # type: ignore
         if len(postpath) != 1:
             raise UnrecognizedRequestError()
         session_id = postpath[0].decode("ascii")
@@ -50,7 +50,7 @@ class MSC4108RendezvousSessionResource(DirectServeJsonResource):
         self._handler.handle_put(request, session_id)
 
     def _async_render_DELETE(self, request: SynapseRequest) -> None:
-        postpath: List[bytes] = request.postpath  # type: ignore
+        postpath: list[bytes] = request.postpath  # type: ignore
         if len(postpath) != 1:
             raise UnrecognizedRequestError()
         session_id = postpath[0].decode("ascii")
diff --git a/synapse/rest/synapse/mas/devices.py b/synapse/rest/synapse/mas/devices.py
index 6cc1153590..9d94a67675 100644
--- a/synapse/rest/synapse/mas/devices.py
+++ b/synapse/rest/synapse/mas/devices.py
@@ -15,9 +15,10 @@
 
 import logging
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Optional, Tuple
+from typing import TYPE_CHECKING
+
+from pydantic import StrictStr
 
-from synapse._pydantic_compat import StrictStr
 from synapse.api.errors import NotFoundError
 from synapse.http.servlet import parse_and_validate_json_object_from_request
 from synapse.types import JsonDict, UserID
@@ -52,11 +53,11 @@ class MasUpsertDeviceResource(MasBaseResource):
     class PostBody(RequestBodyModel):
         localpart: StrictStr
         device_id: StrictStr
-        display_name: Optional[StrictStr]
+        display_name: StrictStr | None = None
 
     async def _async_render_POST(
         self, request: "SynapseRequest"
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         self.assert_request_is_from_mas(request)
 
         body = parse_and_validate_json_object_from_request(request, self.PostBody)
@@ -97,7 +98,7 @@ class MasDeleteDeviceResource(MasBaseResource):
 
     async def _async_render_POST(
         self, request: "SynapseRequest"
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         self.assert_request_is_from_mas(request)
 
         body = parse_and_validate_json_object_from_request(request, self.PostBody)
@@ -138,7 +139,7 @@ class MasUpdateDeviceDisplayNameResource(MasBaseResource):
 
     async def _async_render_POST(
         self, request: "SynapseRequest"
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         self.assert_request_is_from_mas(request)
 
         body = parse_and_validate_json_object_from_request(request, self.PostBody)
@@ -176,11 +177,11 @@ class MasSyncDevicesResource(MasBaseResource):
 
     class PostBody(RequestBodyModel):
         localpart: StrictStr
-        devices: set[StrictStr]
+        devices: list[str]
 
     async def _async_render_POST(
         self, request: "SynapseRequest"
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         self.assert_request_is_from_mas(request)
 
         body = parse_and_validate_json_object_from_request(request, self.PostBody)
diff --git a/synapse/rest/synapse/mas/users.py b/synapse/rest/synapse/mas/users.py
index 09aa13bebb..55c7337555 100644
--- a/synapse/rest/synapse/mas/users.py
+++ b/synapse/rest/synapse/mas/users.py
@@ -15,9 +15,10 @@
 
 import logging
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Any, Optional, Tuple, TypedDict
+from typing import TYPE_CHECKING, Any, TypedDict
+
+from pydantic import StrictBool, StrictStr, model_validator
 
-from synapse._pydantic_compat import StrictBool, StrictStr, root_validator
 from synapse.api.errors import NotFoundError, SynapseError
 from synapse.http.servlet import (
     parse_and_validate_json_object_from_request,
@@ -51,20 +52,20 @@ class MasQueryUserResource(MasBaseResource):
 
     class Response(TypedDict):
         user_id: str
-        display_name: Optional[str]
-        avatar_url: Optional[str]
+        display_name: str | None
+        avatar_url: str | None
         is_suspended: bool
         is_deactivated: bool
 
     async def _async_render_GET(
         self, request: "SynapseRequest"
-    ) -> Tuple[int, Response]:
+    ) -> tuple[int, Response]:
         self.assert_request_is_from_mas(request)
 
         localpart = parse_string(request, "localpart", required=True)
         user_id = UserID(localpart, self.hostname)
 
-        user: Optional[UserInfo] = await self.store.get_user_by_id(user_id=str(user_id))
+        user: UserInfo | None = await self.store.get_user_by_id(user_id=str(user_id))
         if user is None:
             raise NotFoundError("User not found")
 
@@ -103,15 +104,16 @@ class MasProvisionUserResource(MasBaseResource):
         localpart: StrictStr
 
         unset_displayname: StrictBool = False
-        set_displayname: Optional[StrictStr] = None
+        set_displayname: StrictStr | None = None
 
         unset_avatar_url: StrictBool = False
-        set_avatar_url: Optional[StrictStr] = None
+        set_avatar_url: StrictStr | None = None
 
         unset_emails: StrictBool = False
-        set_emails: Optional[list[StrictStr]] = None
+        set_emails: list[StrictStr] | None = None
 
-        @root_validator(pre=True)
+        @model_validator(mode="before")
+        @classmethod
         def validate_exclusive(cls, values: Any) -> Any:
             if "unset_displayname" in values and "set_displayname" in values:
                 raise ValueError(
@@ -128,7 +130,7 @@ class MasProvisionUserResource(MasBaseResource):
 
     async def _async_render_POST(
         self, request: "SynapseRequest"
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         self.assert_request_is_from_mas(request)
 
         body = parse_and_validate_json_object_from_request(request, self.PostBody)
@@ -163,7 +165,7 @@ class MasProvisionUserResource(MasBaseResource):
                     by_admin=True,
                 )
 
-            new_email_list: Optional[set[str]] = None
+            new_email_list: set[str] | None = None
             if body.unset_emails:
                 new_email_list = set()
             elif body.set_emails is not None:
@@ -239,7 +241,7 @@ class MasIsLocalpartAvailableResource(MasBaseResource):
 
     async def _async_render_GET(
         self, request: "SynapseRequest"
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         self.assert_request_is_from_mas(request)
         localpart = parse_string(request, "localpart")
         if localpart is None:
@@ -272,7 +274,7 @@ class MasDeleteUserResource(MasBaseResource):
 
     async def _async_render_POST(
         self, request: "SynapseRequest"
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         self.assert_request_is_from_mas(request)
 
         body = parse_and_validate_json_object_from_request(request, self.PostBody)
@@ -312,7 +314,7 @@ class MasReactivateUserResource(MasBaseResource):
 
     async def _async_render_POST(
         self, request: "SynapseRequest"
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         self.assert_request_is_from_mas(request)
 
         body = parse_and_validate_json_object_from_request(request, self.PostBody)
@@ -350,7 +352,7 @@ class MasSetDisplayNameResource(MasBaseResource):
 
     async def _async_render_POST(
         self, request: "SynapseRequest"
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         self.assert_request_is_from_mas(request)
 
         body = parse_and_validate_json_object_from_request(request, self.PostBody)
@@ -394,7 +396,7 @@ class MasUnsetDisplayNameResource(MasBaseResource):
 
     async def _async_render_POST(
         self, request: "SynapseRequest"
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         self.assert_request_is_from_mas(request)
 
         body = parse_and_validate_json_object_from_request(request, self.PostBody)
@@ -440,7 +442,7 @@ class MasAllowCrossSigningResetResource(MasBaseResource):
 
     async def _async_render_POST(
         self, request: "SynapseRequest"
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         self.assert_request_is_from_mas(request)
 
         body = parse_and_validate_json_object_from_request(request, self.PostBody)
diff --git a/synapse/rest/well_known.py b/synapse/rest/well_known.py
index ae8c6a8fc0..801d474ecc 100644
--- a/synapse/rest/well_known.py
+++ b/synapse/rest/well_known.py
@@ -18,7 +18,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, Optional, Tuple
+from typing import TYPE_CHECKING
 
 from twisted.web.resource import Resource
 from twisted.web.server import Request
@@ -42,7 +42,7 @@ class WellKnownBuilder:
         self._config = hs.config
         self._auth = hs.get_auth()
 
-    async def get_well_known(self) -> Optional[JsonDict]:
+    async def get_well_known(self) -> JsonDict | None:
         if not self._config.server.serve_client_wellknown:
             return None
 
@@ -97,7 +97,7 @@ class ClientWellKnownResource(DirectServeJsonResource):
         super().__init__(clock=hs.get_clock())
         self._well_known_builder = WellKnownBuilder(hs)
 
-    async def _async_render_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def _async_render_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         r = await self._well_known_builder.get_well_known()
         if not r:
             raise NotFoundError(".well-known not available")
diff --git a/synapse/server.py b/synapse/server.py
index edcab19d72..de0a2b098c 100644
--- a/synapse/server.py
+++ b/synapse/server.py
@@ -28,10 +28,22 @@
 import abc
 import functools
 import logging
-from typing import TYPE_CHECKING, Callable, Dict, List, Optional, Type, TypeVar, cast
+from threading import Thread
+from typing import (
+    TYPE_CHECKING,
+    Any,
+    Awaitable,
+    Callable,
+    TypeVar,
+    cast,
+)
+from wsgiref.simple_server import WSGIServer
 
+from attr import dataclass
 from typing_extensions import TypeAlias
 
+from twisted.internet import defer
+from twisted.internet.base import _SystemEventID
 from twisted.internet.interfaces import IOpenSSLContextFactory
 from twisted.internet.tcp import Port
 from twisted.python.threadpool import ThreadPool
@@ -44,6 +56,8 @@ from synapse.api.auth.mas import MasDelegatedAuth
 from synapse.api.auth_blocking import AuthBlocking
 from synapse.api.filtering import Filtering
 from synapse.api.ratelimiting import Ratelimiter, RequestRatelimiter
+from synapse.app._base import unregister_sighups
+from synapse.app.phone_stats_home import start_phone_stats_home
 from synapse.appservice.api import ApplicationServiceApi
 from synapse.appservice.scheduler import ApplicationServiceScheduler
 from synapse.config.homeserver import HomeServerConfig
@@ -128,11 +142,13 @@ from synapse.http.client import (
     SimpleHttpClient,
 )
 from synapse.http.matrixfederationclient import MatrixFederationHttpClient
+from synapse.logging.context import PreserveLoggingContext
 from synapse.media.media_repository import MediaRepository
 from synapse.metrics import (
     all_later_gauges_to_clean_up_on_shutdown,
     register_threadpool,
 )
+from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.metrics.common_usage_metrics import CommonUsageMetricsManager
 from synapse.module_api import ModuleApi
 from synapse.module_api.callbacks import ModuleApiCallbacks
@@ -156,6 +172,8 @@ from synapse.storage.controllers import StorageControllers
 from synapse.streams.events import EventSources
 from synapse.synapse_rust.rendezvous import RendezvousHandler
 from synapse.types import DomainSpecificString, ISynapseReactor
+from synapse.util import SYNAPSE_VERSION
+from synapse.util.caches import CACHE_METRIC_REGISTRY
 from synapse.util.clock import Clock
 from synapse.util.distributor import Distributor
 from synapse.util.macaroons import MacaroonGenerator
@@ -166,7 +184,9 @@ from synapse.util.task_scheduler import TaskScheduler
 logger = logging.getLogger(__name__)
 
 if TYPE_CHECKING:
+    # Old Python versions don't have `LiteralString`
     from txredisapi import ConnectionHandler
+    from typing_extensions import LiteralString
 
     from synapse.handlers.jwt import JwtHandler
     from synapse.handlers.oidc import OidcHandler
@@ -196,6 +216,7 @@ if TYPE_CHECKING:
 
 T: TypeAlias = object
 F = TypeVar("F", bound=Callable[["HomeServer"], T])
+R = TypeVar("R")
 
 
 def cache_in_self(builder: F) -> F:
@@ -219,7 +240,8 @@ def cache_in_self(builder: F) -> F:
     @functools.wraps(builder)
     def _get(self: "HomeServer") -> T:
         try:
-            return getattr(self, depname)
+            dep = getattr(self, depname)
+            return dep
         except AttributeError:
             pass
 
@@ -239,6 +261,22 @@ def cache_in_self(builder: F) -> F:
     return cast(F, _get)
 
 
+@dataclass
+class ShutdownInfo:
+    """Information for callable functions called at time of shutdown.
+
+    Attributes:
+        func: the object to call before shutdown.
+        trigger_id: an ID returned when registering this event trigger.
+        args: the arguments to call the function with.
+        kwargs: the keyword arguments to call the function with.
+    """
+
+    func: Callable[..., Any]
+    trigger_id: _SystemEventID
+    kwargs: dict[str, object]
+
+
 class HomeServer(metaclass=abc.ABCMeta):
     """A basic homeserver object without lazy component builders.
 
@@ -271,7 +309,7 @@ class HomeServer(metaclass=abc.ABCMeta):
 
     @property
     @abc.abstractmethod
-    def DATASTORE_CLASS(self) -> Type["SQLBaseStore"]:
+    def DATASTORE_CLASS(self) -> type["SQLBaseStore"]:
         # This is overridden in derived application classes
         # (such as synapse.app.homeserver.SynapseHomeServer) and gives the class to be
         # instantiated during setup() for future return by get_datastores()
@@ -281,14 +319,14 @@ class HomeServer(metaclass=abc.ABCMeta):
         self,
         hostname: str,
         config: HomeServerConfig,
-        reactor: Optional[ISynapseReactor] = None,
-        version_string: str = "Synapse",
+        reactor: ISynapseReactor | None = None,
     ):
         """
         Args:
             hostname : The hostname for the server.
             config: The full config for the homeserver.
         """
+
         if not reactor:
             from twisted.internet import reactor as _reactor
 
@@ -299,21 +337,228 @@ class HomeServer(metaclass=abc.ABCMeta):
         # the key we use to sign events and requests
         self.signing_key = config.key.signing_key[0]
         self.config = config
-        self._listening_services: List[Port] = []
-        self.start_time: Optional[int] = None
+        self._listening_services: list[Port] = []
+        self._metrics_listeners: list[tuple[WSGIServer, Thread]] = []
+        self.start_time: int | None = None
 
         self._instance_id = random_string(5)
         self._instance_name = config.worker.instance_name
 
-        self.version_string = version_string
+        self.version_string = f"Synapse/{SYNAPSE_VERSION}"
 
-        self.datastores: Optional[Databases] = None
+        self.datastores: Databases | None = None
 
-        self._module_web_resources: Dict[str, Resource] = {}
+        self._module_web_resources: dict[str, Resource] = {}
         self._module_web_resources_consumed = False
 
         # This attribute is set by the free function `refresh_certificate`.
-        self.tls_server_context_factory: Optional[IOpenSSLContextFactory] = None
+        self.tls_server_context_factory: IOpenSSLContextFactory | None = None
+
+        self._is_shutdown = False
+        self._async_shutdown_handlers: list[ShutdownInfo] = []
+        self._sync_shutdown_handlers: list[ShutdownInfo] = []
+        self._background_processes: set[defer.Deferred[Any | None]] = set()
+
+    def run_as_background_process(
+        self,
+        desc: "LiteralString",
+        func: Callable[..., Awaitable[R | None]],
+        *args: Any,
+        **kwargs: Any,
+    ) -> "defer.Deferred[R | None]":
+        """Run the given function in its own logcontext, with resource metrics
+
+        This should be used to wrap processes which are fired off to run in the
+        background, instead of being associated with a particular request.
+
+        It returns a Deferred which completes when the function completes, but it doesn't
+        follow the synapse logcontext rules, which makes it appropriate for passing to
+        clock.looping_call and friends (or for firing-and-forgetting in the middle of a
+        normal synapse async function).
+
+        Because the returned Deferred does not follow the synapse logcontext rules, awaiting
+        the result of this function will result in the log context being cleared (bad). In
+        order to properly await the result of this function and maintain the current log
+        context, use `make_deferred_yieldable`.
+
+        Args:
+            desc: a description for this background process type
+            server_name: The homeserver name that this background process is being run for
+                (this should be `hs.hostname`).
+            func: a function, which may return a Deferred or a coroutine
+            bg_start_span: Whether to start an opentracing span. Defaults to True.
+                Should only be disabled for processes that will not log to or tag
+                a span.
+            args: positional args for func
+            kwargs: keyword args for func
+
+        Returns:
+            Deferred which returns the result of func, or `None` if func raises.
+            Note that the returned Deferred does not follow the synapse logcontext
+            rules.
+        """
+        if self._is_shutdown:
+            raise Exception(
+                f"Cannot start background process. HomeServer has been shutdown {len(self._background_processes)} {len(self.get_clock()._looping_calls)} {len(self.get_clock()._call_id_to_delayed_call)}"
+            )
+
+        # Ignore linter error as this is the one location this should be called.
+        deferred = run_as_background_process(desc, self.hostname, func, *args, **kwargs)  # type: ignore[untracked-background-process]
+        self._background_processes.add(deferred)
+
+        def on_done(res: R) -> R:
+            try:
+                self._background_processes.remove(deferred)
+            except KeyError:
+                # If the background process isn't being tracked anymore we can just move on.
+                pass
+            return res
+
+        deferred.addBoth(on_done)
+        return deferred
+
+    async def shutdown(self) -> None:
+        """
+        Cleanly stops all aspects of the HomeServer and removes any references that
+        have been handed out in order to allow the HomeServer object to be garbage
+        collected.
+
+        You must ensure the HomeServer object to not be frozen in the garbage collector
+        in order for it to be cleaned up. By default, Synapse freezes the HomeServer
+        object in the garbage collector.
+        """
+
+        self._is_shutdown = True
+
+        logger.info(
+            "Received shutdown request for %s (%s).",
+            self.hostname,
+            self.get_instance_id(),
+        )
+
+        # Unregister sighups first. If a shutdown was requested we shouldn't be responding
+        # to things like config changes. So it would be best to stop listening to these first.
+        unregister_sighups(self._instance_id)
+
+        # TODO: It would be desireable to be able to report an error if the HomeServer
+        # object is frozen in the garbage collector as that would prevent it from being
+        # collected after being shutdown.
+        # In theory the following should work, but it doesn't seem to make a difference
+        # when I test it locally.
+        #
+        # if gc.is_tracked(self):
+        #    logger.error("HomeServer object is tracked by garbage collection so cannot be fully cleaned up")
+
+        for listener in self._listening_services:
+            # During unit tests, an incomplete `twisted.pair.testing._FakePort` is used
+            # for listeners so check listener type here to ensure shutdown procedure is
+            # only applied to actual `Port` instances.
+            if type(listener) is Port:
+                port_shutdown = listener.stopListening()
+                if port_shutdown is not None:
+                    await port_shutdown
+        self._listening_services.clear()
+
+        for server, thread in self._metrics_listeners:
+            server.shutdown()
+            thread.join()
+        self._metrics_listeners.clear()
+
+        # TODO: Cleanup replication pieces
+
+        self.get_keyring().shutdown()
+
+        # Cleanup metrics associated with the homeserver
+        for later_gauge in all_later_gauges_to_clean_up_on_shutdown.values():
+            later_gauge.unregister_hooks_for_homeserver_instance_id(
+                self.get_instance_id()
+            )
+
+        CACHE_METRIC_REGISTRY.unregister_hooks_for_homeserver(
+            self.config.server.server_name
+        )
+
+        for db in self.get_datastores().databases:
+            db.stop_background_updates()
+
+        if self.should_send_federation():
+            try:
+                self.get_federation_sender().shutdown()
+            except Exception:
+                pass
+
+        for shutdown_handler in self._async_shutdown_handlers:
+            try:
+                self.get_reactor().removeSystemEventTrigger(shutdown_handler.trigger_id)
+                defer.ensureDeferred(shutdown_handler.func(**shutdown_handler.kwargs))
+            except Exception as e:
+                logger.error("Error calling shutdown async handler: %s", e)
+        self._async_shutdown_handlers.clear()
+
+        for shutdown_handler in self._sync_shutdown_handlers:
+            try:
+                self.get_reactor().removeSystemEventTrigger(shutdown_handler.trigger_id)
+                shutdown_handler.func(**shutdown_handler.kwargs)
+            except Exception as e:
+                logger.error("Error calling shutdown sync handler: %s", e)
+        self._sync_shutdown_handlers.clear()
+
+        self.get_clock().shutdown()
+
+        for background_process in list(self._background_processes):
+            try:
+                with PreserveLoggingContext():
+                    background_process.cancel()
+            except Exception:
+                pass
+        self._background_processes.clear()
+
+        for db in self.get_datastores().databases:
+            db._db_pool.close()
+
+    def register_async_shutdown_handler(
+        self,
+        *,
+        phase: str,
+        eventType: str,
+        shutdown_func: Callable[..., Any],
+        **kwargs: object,
+    ) -> None:
+        """
+        Register a system event trigger with the HomeServer so it can be cleanly
+        removed when the HomeServer is shutdown.
+        """
+        id = self.get_clock().add_system_event_trigger(
+            phase,
+            eventType,
+            shutdown_func,
+            **kwargs,
+        )
+        self._async_shutdown_handlers.append(
+            ShutdownInfo(func=shutdown_func, trigger_id=id, kwargs=kwargs)
+        )
+
+    def register_sync_shutdown_handler(
+        self,
+        *,
+        phase: str,
+        eventType: str,
+        shutdown_func: Callable[..., Any],
+        **kwargs: object,
+    ) -> None:
+        """
+        Register a system event trigger with the HomeServer so it can be cleanly
+        removed when the HomeServer is shutdown.
+        """
+        id = self.get_clock().add_system_event_trigger(
+            phase,
+            eventType,
+            shutdown_func,
+            **kwargs,
+        )
+        self._sync_shutdown_handlers.append(
+            ShutdownInfo(func=shutdown_func, trigger_id=id, kwargs=kwargs)
+        )
 
     def register_module_web_resource(self, path: str, resource: Resource) -> None:
         """Allows a module to register a web resource to be served at the given path.
@@ -366,36 +611,19 @@ class HomeServer(metaclass=abc.ABCMeta):
         self.datastores = Databases(self.DATASTORE_CLASS, self)
         logger.info("Finished setting up.")
 
-    def __del__(self) -> None:
-        """
-        Called when an the homeserver is garbage collected.
-
-        Make sure we actually do some clean-up, rather than leak data.
-        """
-        self.cleanup()
-
-    def cleanup(self) -> None:
-        """
-        WIP: Clean-up any references to the homeserver and stop any running related
-        processes, timers, loops, replication stream, etc.
-
-        This should be called wherever you care about the HomeServer being completely
-        garbage collected like in tests. It's not necessary to call if you plan to just
-        shut down the whole Python process anyway.
-
-        Can be called multiple times.
-        """
-        logger.info("Received cleanup request for %s.", self.hostname)
-
-        # TODO: Stop background processes, timers, loops, replication stream, etc.
-
-        # Cleanup metrics associated with the homeserver
-        for later_gauge in all_later_gauges_to_clean_up_on_shutdown.values():
-            later_gauge.unregister_hooks_for_homeserver_instance_id(
-                self.get_instance_id()
-            )
-
-        logger.info("Cleanup complete for %s.", self.hostname)
+    # def __del__(self) -> None:
+    #    """
+    #    Called when an the homeserver is garbage collected.
+    #
+    #    Make sure we actually do some clean-up, rather than leak data.
+    #    """
+    #
+    #    # NOTE: This is a chicken and egg problem.
+    #    # __del__ will never be called since the HomeServer cannot be garbage collected
+    #    # until the shutdown function has been called. So it makes no sense to call
+    #    # shutdown inside of __del__, even though that is a logical place to assume it
+    #    # should be called.
+    #    self.shutdown()
 
     def start_listening(self) -> None:  # noqa: B027 (no-op by design)
         """Start the HTTP, manhole, metrics, etc listeners
@@ -413,6 +641,8 @@ class HomeServer(metaclass=abc.ABCMeta):
         for i in self.REQUIRED_ON_BACKGROUND_TASK_STARTUP:
             getattr(self, "get_" + i + "_handler")()
         self.get_task_scheduler()
+        self.get_common_usage_metrics_manager().setup()
+        start_phone_stats_home(self)
 
     def get_reactor(self) -> ISynapseReactor:
         """
@@ -442,7 +672,8 @@ class HomeServer(metaclass=abc.ABCMeta):
 
     @cache_in_self
     def get_clock(self) -> Clock:
-        return Clock(self._reactor, server_name=self.hostname)
+        # Ignore the linter error since this is the one place the `Clock` should be created.
+        return Clock(self._reactor, server_name=self.hostname)  # type: ignore[multiple-internal-clocks]
 
     def get_datastores(self) -> Databases:
         if not self.datastores:
@@ -452,7 +683,7 @@ class HomeServer(metaclass=abc.ABCMeta):
 
     @cache_in_self
     def get_distributor(self) -> Distributor:
-        return Distributor(server_name=self.hostname)
+        return Distributor(hs=self)
 
     @cache_in_self
     def get_registration_ratelimiter(self) -> Ratelimiter:
@@ -874,7 +1105,7 @@ class HomeServer(metaclass=abc.ABCMeta):
         return ReplicationDataHandler(self)
 
     @cache_in_self
-    def get_replication_streams(self) -> Dict[str, Stream]:
+    def get_replication_streams(self) -> dict[str, Stream]:
         return {stream.NAME: stream(self) for stream in STREAMS_MAP.values()}
 
     @cache_in_self
@@ -1007,8 +1238,10 @@ class HomeServer(metaclass=abc.ABCMeta):
         )
 
         media_threadpool.start()
-        self.get_clock().add_system_event_trigger(
-            "during", "shutdown", media_threadpool.stop
+        self.register_sync_shutdown_handler(
+            phase="during",
+            eventType="shutdown",
+            shutdown_func=media_threadpool.stop,
         )
 
         # Register the threadpool with our metrics.
diff --git a/synapse/server_notices/consent_server_notices.py b/synapse/server_notices/consent_server_notices.py
index d937a3034e..99b362f5ff 100644
--- a/synapse/server_notices/consent_server_notices.py
+++ b/synapse/server_notices/consent_server_notices.py
@@ -18,7 +18,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, Any, Set
+from typing import TYPE_CHECKING, Any
 
 from synapse.api.errors import SynapseError
 from synapse.api.urls import ConsentURIBuilder
@@ -40,7 +40,7 @@ class ConsentServerNotices:
         self._server_notices_manager = hs.get_server_notices_manager()
         self._store = hs.get_datastores().main
 
-        self._users_in_progress: Set[str] = set()
+        self._users_in_progress: set[str] = set()
 
         self._current_consent_version = hs.config.consent.user_consent_version
         self._server_notice_content = (
diff --git a/synapse/server_notices/resource_limits_server_notices.py b/synapse/server_notices/resource_limits_server_notices.py
index e88e8c9b45..493b8cb62b 100644
--- a/synapse/server_notices/resource_limits_server_notices.py
+++ b/synapse/server_notices/resource_limits_server_notices.py
@@ -18,7 +18,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, List, Tuple
+from typing import TYPE_CHECKING
 
 from synapse.api.constants import (
     EventTypes,
@@ -127,7 +127,7 @@ class ResourceLimitsServerNotices:
             logger.error("Error sending resource limits server notice: %s", e)
 
     async def _remove_limit_block_notification(
-        self, user_id: str, ref_events: List[str]
+        self, user_id: str, ref_events: list[str]
     ) -> None:
         """Utility method to remove limit block notifications from the server
         notices room.
@@ -170,7 +170,7 @@ class ResourceLimitsServerNotices:
             user_id, content, EventTypes.Pinned, ""
         )
 
-    async def _is_room_currently_blocked(self, room_id: str) -> Tuple[bool, List[str]]:
+    async def _is_room_currently_blocked(self, room_id: str) -> tuple[bool, list[str]]:
         """
         Determines if the room is currently blocked
 
@@ -198,7 +198,7 @@ class ResourceLimitsServerNotices:
             # The user has yet to join the server notices room
             pass
 
-        referenced_events: List[str] = []
+        referenced_events: list[str] = []
         if pinned_state_event is not None:
             referenced_events = list(pinned_state_event.content.get("pinned", []))
 
diff --git a/synapse/server_notices/server_notices_manager.py b/synapse/server_notices/server_notices_manager.py
index 19f86b5a56..b4e512618e 100644
--- a/synapse/server_notices/server_notices_manager.py
+++ b/synapse/server_notices/server_notices_manager.py
@@ -18,7 +18,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING
 
 from synapse.api.constants import EventTypes, Membership, RoomCreationPreset
 from synapse.events import EventBase
@@ -36,6 +36,7 @@ SERVER_NOTICE_ROOM_TAG = "m.server_notice"
 class ServerNoticesManager:
     def __init__(self, hs: "HomeServer"):
         self.server_name = hs.hostname  # nb must be called this for @cached
+        self.clock = hs.get_clock()  # nb must be called this for @cached
         self._store = hs.get_datastores().main
         self._config = hs.config
         self._account_data_handler = hs.get_account_data_handler()
@@ -58,8 +59,8 @@ class ServerNoticesManager:
         user_id: str,
         event_content: dict,
         type: str = EventTypes.Message,
-        state_key: Optional[str] = None,
-        txn_id: Optional[str] = None,
+        state_key: str | None = None,
+        txn_id: str | None = None,
     ) -> EventBase:
         """Send a notice to the given user
 
@@ -98,7 +99,7 @@ class ServerNoticesManager:
         return event
 
     @cached()
-    async def maybe_get_notice_room_for_user(self, user_id: str) -> Optional[str]:
+    async def maybe_get_notice_room_for_user(self, user_id: str) -> str | None:
         """Try to look up the server notice room for this user if it exists.
 
         Does not create one if none can be found.
@@ -293,8 +294,8 @@ class ServerNoticesManager:
         self,
         requester: Requester,
         room_id: str,
-        display_name: Optional[str],
-        avatar_url: Optional[str],
+        display_name: str | None,
+        avatar_url: str | None,
     ) -> None:
         """
         Updates the notice user's profile if it's different from what is in the room.
@@ -340,7 +341,7 @@ class ServerNoticesManager:
         room_id: str,
         info_event_type: str,
         info_content_key: str,
-        info_value: Optional[str],
+        info_value: str | None,
     ) -> None:
         """
         Updates a specific notice room's info if it's different from what is set.
diff --git a/synapse/server_notices/server_notices_sender.py b/synapse/server_notices/server_notices_sender.py
index bc62d6ac6c..fd4f36f5c8 100644
--- a/synapse/server_notices/server_notices_sender.py
+++ b/synapse/server_notices/server_notices_sender.py
@@ -17,7 +17,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import TYPE_CHECKING, Iterable, Union
+from typing import TYPE_CHECKING, Iterable
 
 from synapse.server_notices.consent_server_notices import ConsentServerNotices
 from synapse.server_notices.resource_limits_server_notices import (
@@ -39,7 +39,7 @@ class ServerNoticesSender(WorkerServerNoticesSender):
     def __init__(self, hs: "HomeServer"):
         super().__init__(hs)
         self._server_notices: Iterable[
-            Union[ConsentServerNotices, ResourceLimitsServerNotices]
+            ConsentServerNotices | ResourceLimitsServerNotices
         ] = (
             ConsentServerNotices(hs),
             ResourceLimitsServerNotices(hs),
diff --git a/synapse/state/__init__.py b/synapse/state/__init__.py
index dd8d7135ba..9fc49be4b1 100644
--- a/synapse/state/__init__.py
+++ b/synapse/state/__init__.py
@@ -26,15 +26,9 @@ from typing import (
     Any,
     Awaitable,
     Callable,
-    DefaultDict,
-    Dict,
-    FrozenSet,
-    List,
     Mapping,
     Optional,
     Sequence,
-    Set,
-    Tuple,
 )
 
 import attr
@@ -102,10 +96,10 @@ class _StateCacheEntry:
 
     def __init__(
         self,
-        state: Optional[StateMap[str]],
-        state_group: Optional[int],
-        prev_group: Optional[int] = None,
-        delta_ids: Optional[StateMap[str]] = None,
+        state: StateMap[str] | None,
+        state_group: int | None,
+        prev_group: int | None = None,
+        delta_ids: StateMap[str] | None = None,
     ):
         if state is None and state_group is None and prev_group is None:
             raise Exception("One of state, state_group or prev_group must be not None")
@@ -117,7 +111,7 @@ class _StateCacheEntry:
         #
         # This can be None if we have a `state_group` (as then we can fetch the
         # state from the DB.)
-        self._state: Optional[StateMap[str]] = (
+        self._state: StateMap[str] | None = (
             immutabledict(state) if state is not None else None
         )
 
@@ -126,7 +120,7 @@ class _StateCacheEntry:
         self.state_group = state_group
 
         self.prev_group = prev_group
-        self.delta_ids: Optional[StateMap[str]] = (
+        self.delta_ids: StateMap[str] | None = (
             immutabledict(delta_ids) if delta_ids is not None else None
         )
 
@@ -212,7 +206,7 @@ class StateHandler:
         self,
         room_id: str,
         event_ids: StrCollection,
-        state_filter: Optional[StateFilter] = None,
+        state_filter: StateFilter | None = None,
         await_full_state: bool = True,
     ) -> StateMap[str]:
         """Fetch the state after each of the given event IDs. Resolve them and return.
@@ -246,7 +240,7 @@ class StateHandler:
 
     async def get_current_user_ids_in_room(
         self, room_id: str, latest_event_ids: StrCollection
-    ) -> Set[str]:
+    ) -> set[str]:
         """
         Get the users IDs who are currently in a room.
 
@@ -271,7 +265,7 @@ class StateHandler:
 
     async def get_hosts_in_room_at_events(
         self, room_id: str, event_ids: StrCollection
-    ) -> FrozenSet[str]:
+    ) -> frozenset[str]:
         """Get the hosts that were in a room at the given event ids
 
         Args:
@@ -289,9 +283,9 @@ class StateHandler:
     async def calculate_context_info(
         self,
         event: EventBase,
-        state_ids_before_event: Optional[StateMap[str]] = None,
-        partial_state: Optional[bool] = None,
-        state_group_before_event: Optional[int] = None,
+        state_ids_before_event: StateMap[str] | None = None,
+        partial_state: bool | None = None,
+        state_group_before_event: int | None = None,
     ) -> UnpersistedEventContextBase:
         """
         Calulates the contents of an unpersisted event context, other than the current
@@ -462,8 +456,8 @@ class StateHandler:
     async def compute_event_context(
         self,
         event: EventBase,
-        state_ids_before_event: Optional[StateMap[str]] = None,
-        partial_state: Optional[bool] = None,
+        state_ids_before_event: StateMap[str] | None = None,
+        partial_state: bool | None = None,
     ) -> EventContext:
         """Build an EventContext structure for a non-outlier event.
 
@@ -647,10 +641,11 @@ class StateResolutionHandler:
         )
 
         # dict of set of event_ids -> _StateCacheEntry.
-        self._state_cache: ExpiringCache[FrozenSet[int], _StateCacheEntry] = (
+        self._state_cache: ExpiringCache[frozenset[int], _StateCacheEntry] = (
             ExpiringCache(
                 cache_name="state_cache",
                 server_name=self.server_name,
+                hs=hs,
                 clock=self.clock,
                 max_len=100000,
                 expiry_ms=EVICTION_TIMEOUT_SECONDS * 1000,
@@ -664,7 +659,7 @@ class StateResolutionHandler:
         #
 
         # tracks the amount of work done on state res per room
-        self._state_res_metrics: DefaultDict[str, _StateResMetrics] = defaultdict(
+        self._state_res_metrics: defaultdict[str, _StateResMetrics] = defaultdict(
             _StateResMetrics
         )
 
@@ -675,7 +670,7 @@ class StateResolutionHandler:
         room_id: str,
         room_version: str,
         state_groups_ids: Mapping[int, StateMap[str]],
-        event_map: Optional[Dict[str, EventBase]],
+        event_map: dict[str, EventBase] | None,
         state_res_store: "StateResolutionStore",
     ) -> _StateCacheEntry:
         """Resolves conflicts between a set of state groups
@@ -775,7 +770,7 @@ class StateResolutionHandler:
         room_id: str,
         room_version: str,
         state_sets: Sequence[StateMap[str]],
-        event_map: Optional[Dict[str, EventBase]],
+        event_map: dict[str, EventBase] | None,
         state_res_store: "StateResolutionStore",
     ) -> StateMap[str]:
         """
@@ -883,7 +878,7 @@ class StateResolutionHandler:
         items = self._state_res_metrics.items()
 
         # log the N biggest rooms
-        biggest: List[Tuple[str, _StateResMetrics]] = heapq.nlargest(
+        biggest: list[tuple[str, _StateResMetrics]] = heapq.nlargest(
             n_to_log, items, key=lambda i: extract_key(i[1])
         )
         metrics_logger.debug(
@@ -939,7 +934,7 @@ def _make_state_cache_entry(
 
     # failing that, look for the closest match.
     prev_group = None
-    delta_ids: Optional[StateMap[str]] = None
+    delta_ids: StateMap[str] | None = None
 
     for old_group, old_state in state_groups_ids.items():
         if old_state.keys() - new_state.keys():
@@ -974,7 +969,7 @@ class StateResolutionStore:
 
     def get_events(
         self, event_ids: StrCollection, allow_rejected: bool = False
-    ) -> Awaitable[Dict[str, EventBase]]:
+    ) -> Awaitable[dict[str, EventBase]]:
         """Get events from the database
 
         Args:
@@ -995,9 +990,9 @@ class StateResolutionStore:
     def get_auth_chain_difference(
         self,
         room_id: str,
-        state_sets: List[Set[str]],
-        conflicted_state: Optional[Set[str]],
-        additional_backwards_reachable_conflicted_events: Optional[Set[str]],
+        state_sets: list[set[str]],
+        conflicted_state: set[str] | None,
+        additional_backwards_reachable_conflicted_events: set[str] | None,
     ) -> Awaitable[StateDifference]:
         """ "Given sets of state events figure out the auth chain difference (as
         per state res v2 algorithm).
diff --git a/synapse/state/v1.py b/synapse/state/v1.py
index a2e9eb0a42..0b4514d322 100644
--- a/synapse/state/v1.py
+++ b/synapse/state/v1.py
@@ -23,13 +23,8 @@ import logging
 from typing import (
     Awaitable,
     Callable,
-    Dict,
     Iterable,
-    List,
-    Optional,
     Sequence,
-    Set,
-    Tuple,
 )
 
 from synapse import event_auth
@@ -49,8 +44,8 @@ async def resolve_events_with_store(
     room_id: str,
     room_version: RoomVersion,
     state_sets: Sequence[StateMap[str]],
-    event_map: Optional[Dict[str, EventBase]],
-    state_map_factory: Callable[[StrCollection], Awaitable[Dict[str, EventBase]]],
+    event_map: dict[str, EventBase] | None,
+    state_map_factory: Callable[[StrCollection], Awaitable[dict[str, EventBase]]],
 ) -> StateMap[str]:
     """
     Args:
@@ -145,7 +140,7 @@ async def resolve_events_with_store(
 
 def _seperate(
     state_sets: Iterable[StateMap[str]],
-) -> Tuple[MutableStateMap[str], MutableStateMap[Set[str]]]:
+) -> tuple[MutableStateMap[str], MutableStateMap[set[str]]]:
     """Takes the state_sets and figures out which keys are conflicted and
     which aren't. i.e., which have multiple different event_ids associated
     with them in different state sets.
@@ -166,7 +161,7 @@ def _seperate(
     """
     state_set_iterator = iter(state_sets)
     unconflicted_state = dict(next(state_set_iterator))
-    conflicted_state: MutableStateMap[Set[str]] = {}
+    conflicted_state: MutableStateMap[set[str]] = {}
 
     for state_set in state_set_iterator:
         for key, value in state_set.items():
@@ -196,8 +191,8 @@ def _seperate(
 def _create_auth_events_from_maps(
     room_version: RoomVersion,
     unconflicted_state: StateMap[str],
-    conflicted_state: StateMap[Set[str]],
-    state_map: Dict[str, EventBase],
+    conflicted_state: StateMap[set[str]],
+    state_map: dict[str, EventBase],
 ) -> StateMap[str]:
     """
 
@@ -228,9 +223,9 @@ def _create_auth_events_from_maps(
 def _resolve_with_state(
     room_version: RoomVersion,
     unconflicted_state_ids: MutableStateMap[str],
-    conflicted_state_ids: StateMap[Set[str]],
+    conflicted_state_ids: StateMap[set[str]],
     auth_event_ids: StateMap[str],
-    state_map: Dict[str, EventBase],
+    state_map: dict[str, EventBase],
 ) -> MutableStateMap[str]:
     conflicted_state = {}
     for key, event_ids in conflicted_state_ids.items():
@@ -263,7 +258,7 @@ def _resolve_with_state(
 
 def _resolve_state_events(
     room_version: RoomVersion,
-    conflicted_state: StateMap[List[EventBase]],
+    conflicted_state: StateMap[list[EventBase]],
     auth_events: MutableStateMap[EventBase],
 ) -> StateMap[EventBase]:
     """This is where we actually decide which of the conflicted state to
@@ -312,7 +307,7 @@ def _resolve_state_events(
 
 
 def _resolve_auth_events(
-    room_version: RoomVersion, events: List[EventBase], auth_events: StateMap[EventBase]
+    room_version: RoomVersion, events: list[EventBase], auth_events: StateMap[EventBase]
 ) -> EventBase:
     reverse = list(reversed(_ordered_events(events)))
 
@@ -347,7 +342,7 @@ def _resolve_auth_events(
 
 
 def _resolve_normal_events(
-    events: List[EventBase], auth_events: StateMap[EventBase]
+    events: list[EventBase], auth_events: StateMap[EventBase]
 ) -> EventBase:
     for event in _ordered_events(events):
         try:
@@ -365,8 +360,8 @@ def _resolve_normal_events(
     return event
 
 
-def _ordered_events(events: Iterable[EventBase]) -> List[EventBase]:
-    def key_func(e: EventBase) -> Tuple[int, str]:
+def _ordered_events(events: Iterable[EventBase]) -> list[EventBase]:
+    def key_func(e: EventBase) -> tuple[int, str]:
         # we have to use utf-8 rather than ascii here because it turns out we allow
         # people to send us events with non-ascii event IDs :/
         return -int(e.depth), hashlib.sha1(e.event_id.encode("utf-8")).hexdigest()
diff --git a/synapse/state/v2.py b/synapse/state/v2.py
index 8bf6706434..c410c3a7ec 100644
--- a/synapse/state/v2.py
+++ b/synapse/state/v2.py
@@ -25,16 +25,11 @@ from typing import (
     Any,
     Awaitable,
     Callable,
-    Dict,
     Generator,
     Iterable,
-    List,
     Literal,
-    Optional,
     Protocol,
     Sequence,
-    Set,
-    Tuple,
     overload,
 )
 
@@ -61,14 +56,14 @@ class StateResolutionStore(Protocol):
     # TestStateResolutionStore in tests.
     def get_events(
         self, event_ids: StrCollection, allow_rejected: bool = False
-    ) -> Awaitable[Dict[str, EventBase]]: ...
+    ) -> Awaitable[dict[str, EventBase]]: ...
 
     def get_auth_chain_difference(
         self,
         room_id: str,
-        state_sets: List[Set[str]],
-        conflicted_state: Optional[Set[str]],
-        additional_backwards_reachable_conflicted_events: Optional[set[str]],
+        state_sets: list[set[str]],
+        conflicted_state: set[str] | None,
+        additional_backwards_reachable_conflicted_events: set[str] | None,
     ) -> Awaitable[StateDifference]: ...
 
 
@@ -88,7 +83,7 @@ async def resolve_events_with_store(
     room_id: str,
     room_version: RoomVersion,
     state_sets: Sequence[StateMap[str]],
-    event_map: Optional[Dict[str, EventBase]],
+    event_map: dict[str, EventBase] | None,
     state_res_store: StateResolutionStore,
 ) -> StateMap[str]:
     """Resolves the state using the v2 state resolution algorithm
@@ -128,7 +123,7 @@ async def resolve_events_with_store(
     logger.debug("%d conflicted state entries", len(conflicted_state))
     logger.debug("Calculating auth chain difference")
 
-    conflicted_set: Optional[Set[str]] = None
+    conflicted_set: set[str] | None = None
     if room_version.state_res == StateResolutionVersions.V2_1:
         # calculate the conflicted subgraph
         conflicted_set = set(itertools.chain.from_iterable(conflicted_state.values()))
@@ -242,7 +237,7 @@ async def resolve_events_with_store(
 async def _get_power_level_for_sender(
     room_id: str,
     event_id: str,
-    event_map: Dict[str, EventBase],
+    event_map: dict[str, EventBase],
     state_res_store: StateResolutionStore,
 ) -> int:
     """Return the power level of the sender of the given event according to
@@ -315,10 +310,10 @@ async def _get_power_level_for_sender(
 async def _get_auth_chain_difference(
     room_id: str,
     state_sets: Sequence[StateMap[str]],
-    unpersisted_events: Dict[str, EventBase],
+    unpersisted_events: dict[str, EventBase],
     state_res_store: StateResolutionStore,
-    conflicted_state: Optional[Set[str]],
-) -> Set[str]:
+    conflicted_state: set[str] | None,
+) -> set[str]:
     """Compare the auth chains of each state set and return the set of events
     that only appear in some, but not all of the auth chains.
 
@@ -356,10 +351,10 @@ async def _get_auth_chain_difference(
     # event IDs if they appear in the `unpersisted_events`. This is the intersection of
     # the event's auth chain with the events in `unpersisted_events` *plus* their
     # auth event IDs.
-    events_to_auth_chain: Dict[str, Set[str]] = {}
+    events_to_auth_chain: dict[str, set[str]] = {}
     # remember the forward links when doing the graph traversal, we'll need it for v2.1 checks
     # This is a map from an event to the set of events that contain it as an auth event.
-    event_to_next_event: Dict[str, Set[str]] = {}
+    event_to_next_event: dict[str, set[str]] = {}
     for event in unpersisted_events.values():
         chain = {event.event_id}
         events_to_auth_chain[event.event_id] = chain
@@ -379,8 +374,8 @@ async def _get_auth_chain_difference(
     #
     # Note: If there are no `unpersisted_events` (which is the common case), we can do a
     # much simpler calculation.
-    additional_backwards_reachable_conflicted_events: Set[str] = set()
-    unpersisted_conflicted_events: Set[str] = set()
+    additional_backwards_reachable_conflicted_events: set[str] = set()
+    unpersisted_conflicted_events: set[str] = set()
     if unpersisted_events:
         # The list of state sets to pass to the store, where each state set is a set
         # of the event ids making up the state. This is similar to `state_sets`,
@@ -388,17 +383,17 @@ async def _get_auth_chain_difference(
         # ((type, state_key)->event_id) mappings; and (b) we have stripped out
         # unpersisted events and replaced them with the persisted events in
         # their auth chain.
-        state_sets_ids: List[Set[str]] = []
+        state_sets_ids: list[set[str]] = []
 
         # For each state set, the unpersisted event IDs reachable (by their auth
         # chain) from the events in that set.
-        unpersisted_set_ids: List[Set[str]] = []
+        unpersisted_set_ids: list[set[str]] = []
 
         for state_set in state_sets:
-            set_ids: Set[str] = set()
+            set_ids: set[str] = set()
             state_sets_ids.append(set_ids)
 
-            unpersisted_ids: Set[str] = set()
+            unpersisted_ids: set[str] = set()
             unpersisted_set_ids.append(unpersisted_ids)
 
             for event_id in state_set.values():
@@ -479,7 +474,7 @@ async def _get_auth_chain_difference(
         # but NOT the backwards conflicted set. This mirrors what the DB layer does but in reverse:
         # we supplied events which are backwards reachable to the DB and now the DB is providing
         # forwards reachable events from the DB.
-        forwards_conflicted_set: Set[str] = set()
+        forwards_conflicted_set: set[str] = set()
         # we include unpersisted conflicted events here to process exclusive unpersisted subgraphs
         search_queue = subgraph_frontier.union(unpersisted_conflicted_events)
         while search_queue:
@@ -490,7 +485,7 @@ async def _get_auth_chain_difference(
 
         # we've already calculated the backwards form as this is the auth chain for each
         # unpersisted conflicted event.
-        backwards_conflicted_set: Set[str] = set()
+        backwards_conflicted_set: set[str] = set()
         for uce in unpersisted_conflicted_events:
             backwards_conflicted_set.update(events_to_auth_chain.get(uce, []))
 
@@ -526,7 +521,7 @@ async def _get_auth_chain_difference(
 
 def _seperate(
     state_sets: Iterable[StateMap[str]],
-) -> Tuple[StateMap[str], StateMap[Set[str]]]:
+) -> tuple[StateMap[str], StateMap[set[str]]]:
     """Return the unconflicted and conflicted state. This is different than in
     the original algorithm, as this defines a key to be conflicted if one of
     the state sets doesn't have that key.
@@ -550,7 +545,7 @@ def _seperate(
             conflicted_state[key] = event_ids
 
     # mypy doesn't understand that discarding None above means that conflicted
-    # state is StateMap[Set[str]], not StateMap[Set[Optional[Str]]].
+    # state is StateMap[set[str]], not StateMap[set[str | None]].
     return unconflicted_state, conflicted_state  # type: ignore[return-value]
 
 
@@ -579,12 +574,12 @@ def _is_power_event(event: EventBase) -> bool:
 
 
 async def _add_event_and_auth_chain_to_graph(
-    graph: Dict[str, Set[str]],
+    graph: dict[str, set[str]],
     room_id: str,
     event_id: str,
-    event_map: Dict[str, EventBase],
+    event_map: dict[str, EventBase],
     state_res_store: StateResolutionStore,
-    full_conflicted_set: Set[str],
+    full_conflicted_set: set[str],
 ) -> None:
     """Helper function for _reverse_topological_power_sort that add the event
     and its auth chain (that is in the auth diff) to the graph
@@ -616,10 +611,10 @@ async def _reverse_topological_power_sort(
     clock: Clock,
     room_id: str,
     event_ids: Iterable[str],
-    event_map: Dict[str, EventBase],
+    event_map: dict[str, EventBase],
     state_res_store: StateResolutionStore,
-    full_conflicted_set: Set[str],
-) -> List[str]:
+    full_conflicted_set: set[str],
+) -> list[str]:
     """Returns a list of the event_ids sorted by reverse topological ordering,
     and then by power level and origin_server_ts
 
@@ -635,7 +630,7 @@ async def _reverse_topological_power_sort(
         The sorted list
     """
 
-    graph: Dict[str, Set[str]] = {}
+    graph: dict[str, set[str]] = {}
     for idx, event_id in enumerate(event_ids, start=1):
         await _add_event_and_auth_chain_to_graph(
             graph, room_id, event_id, event_map, state_res_store, full_conflicted_set
@@ -658,7 +653,7 @@ async def _reverse_topological_power_sort(
         if idx % _AWAIT_AFTER_ITERATIONS == 0:
             await clock.sleep(0)
 
-    def _get_power_order(event_id: str) -> Tuple[int, int, str]:
+    def _get_power_order(event_id: str) -> tuple[int, int, str]:
         ev = event_map[event_id]
         pl = event_to_pl[event_id]
 
@@ -675,9 +670,9 @@ async def _iterative_auth_checks(
     clock: Clock,
     room_id: str,
     room_version: RoomVersion,
-    event_ids: List[str],
+    event_ids: list[str],
     base_state: StateMap[str],
-    event_map: Dict[str, EventBase],
+    event_map: dict[str, EventBase],
     state_res_store: StateResolutionStore,
 ) -> MutableStateMap[str]:
     """Sequentially apply auth checks to each event in given list, updating the
@@ -758,11 +753,11 @@ async def _iterative_auth_checks(
 async def _mainline_sort(
     clock: Clock,
     room_id: str,
-    event_ids: List[str],
-    resolved_power_event_id: Optional[str],
-    event_map: Dict[str, EventBase],
+    event_ids: list[str],
+    resolved_power_event_id: str | None,
+    event_map: dict[str, EventBase],
     state_res_store: StateResolutionStore,
-) -> List[str]:
+) -> list[str]:
     """Returns a sorted list of event_ids sorted by mainline ordering based on
     the given event resolved_power_event_id
 
@@ -829,8 +824,8 @@ async def _mainline_sort(
 async def _get_mainline_depth_for_event(
     clock: Clock,
     event: EventBase,
-    mainline_map: Dict[str, int],
-    event_map: Dict[str, EventBase],
+    mainline_map: dict[str, int],
+    event_map: dict[str, EventBase],
     state_res_store: StateResolutionStore,
 ) -> int:
     """Get the mainline depths for the given event based on the mainline map
@@ -846,7 +841,7 @@ async def _get_mainline_depth_for_event(
     """
 
     room_id = event.room_id
-    tmp_event: Optional[EventBase] = event
+    tmp_event: EventBase | None = event
 
     # We do an iterative search, replacing `event with the power level in its
     # auth events (if any)
@@ -880,7 +875,7 @@ async def _get_mainline_depth_for_event(
 async def _get_event(
     room_id: str,
     event_id: str,
-    event_map: Dict[str, EventBase],
+    event_map: dict[str, EventBase],
     state_res_store: StateResolutionStore,
     allow_none: Literal[False] = False,
 ) -> EventBase: ...
@@ -890,19 +885,19 @@ async def _get_event(
 async def _get_event(
     room_id: str,
     event_id: str,
-    event_map: Dict[str, EventBase],
+    event_map: dict[str, EventBase],
     state_res_store: StateResolutionStore,
     allow_none: Literal[True],
-) -> Optional[EventBase]: ...
+) -> EventBase | None: ...
 
 
 async def _get_event(
     room_id: str,
     event_id: str,
-    event_map: Dict[str, EventBase],
+    event_map: dict[str, EventBase],
     state_res_store: StateResolutionStore,
     allow_none: bool = False,
-) -> Optional[EventBase]:
+) -> EventBase | None:
     """Helper function to look up event in event_map, falling back to looking
     it up in the store
 
@@ -936,7 +931,7 @@ async def _get_event(
 
 
 def lexicographical_topological_sort(
-    graph: Dict[str, Set[str]], key: Callable[[str], Any]
+    graph: dict[str, set[str]], key: Callable[[str], Any]
 ) -> Generator[str, None, None]:
     """Performs a lexicographic reverse topological sort on the graph.
 
@@ -960,7 +955,7 @@ def lexicographical_topological_sort(
     # outgoing edges, c.f.
     # https://en.wikipedia.org/wiki/Topological_sorting#Kahn's_algorithm
     outdegree_map = graph
-    reverse_graph: Dict[str, Set[str]] = {}
+    reverse_graph: dict[str, set[str]] = {}
 
     # Lists of nodes with zero out degree. Is actually a tuple of
     # `(key(node), node)` so that sorting does the right thing
diff --git a/synapse/storage/_base.py b/synapse/storage/_base.py
index f214f55897..8eeea20967 100644
--- a/synapse/storage/_base.py
+++ b/synapse/storage/_base.py
@@ -21,7 +21,7 @@
 #
 import logging
 from abc import ABCMeta
-from typing import TYPE_CHECKING, Any, Collection, Dict, Iterable, Optional, Union
+from typing import TYPE_CHECKING, Any, Collection, Iterable
 
 from synapse.storage.database import (
     DatabasePool,
@@ -56,11 +56,11 @@ class SQLBaseStore(metaclass=ABCMeta):
     ):
         self.hs = hs
         self.server_name = hs.hostname  # nb must be called this for @cached
-        self._clock = hs.get_clock()
+        self.clock = hs.get_clock()  # nb must be called this for @cached
         self.database_engine = database.engine
         self.db_pool = database
 
-        self.external_cached_functions: Dict[str, CachedFunction] = {}
+        self.external_cached_functions: dict[str, CachedFunction] = {}
 
     def process_replication_rows(  # noqa: B027 (no-op by design)
         self,
@@ -176,7 +176,7 @@ class SQLBaseStore(metaclass=ABCMeta):
         )
 
     def _attempt_to_invalidate_cache(
-        self, cache_name: str, key: Optional[Collection[Any]]
+        self, cache_name: str, key: Collection[Any] | None
     ) -> bool:
         """Attempts to invalidate the cache of the given name, ignoring if the
         cache doesn't exist. Mainly used for invalidating caches on workers,
@@ -218,7 +218,7 @@ class SQLBaseStore(metaclass=ABCMeta):
         self.external_cached_functions[cache_name] = func
 
 
-def db_to_json(db_content: Union[memoryview, bytes, bytearray, str]) -> Any:
+def db_to_json(db_content: memoryview | bytes | bytearray | str) -> Any:
     """
     Take some data from a database row and return a JSON-decoded object.
 
diff --git a/synapse/storage/admin_client_config.py b/synapse/storage/admin_client_config.py
index 07acddc660..b56e21edfa 100644
--- a/synapse/storage/admin_client_config.py
+++ b/synapse/storage/admin_client_config.py
@@ -1,5 +1,4 @@
 import logging
-from typing import Optional
 
 from synapse.types import JsonMapping
 
@@ -9,7 +8,7 @@ logger = logging.getLogger(__name__)
 class AdminClientConfig:
     """Class to track various Synapse-specific admin-only client-impacting config options."""
 
-    def __init__(self, account_data: Optional[JsonMapping]):
+    def __init__(self, account_data: JsonMapping | None):
         # Allow soft-failed events to be returned down `/sync` and other
         # client APIs. `io.element.synapse.soft_failed: true` is added to the
         # `unsigned` portion of the event to inform clients that the event
diff --git a/synapse/storage/background_updates.py b/synapse/storage/background_updates.py
index 9aa9e51aeb..c71bcdb7fb 100644
--- a/synapse/storage/background_updates.py
+++ b/synapse/storage/background_updates.py
@@ -28,20 +28,14 @@ from typing import (
     AsyncContextManager,
     Awaitable,
     Callable,
-    Dict,
     Iterable,
-    List,
-    Optional,
     Sequence,
-    Tuple,
-    Type,
     cast,
 )
 
 import attr
+from pydantic import BaseModel
 
-from synapse._pydantic_compat import BaseModel
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.storage.engines import PostgresEngine
 from synapse.storage.types import Connection, Cursor
 from synapse.types import JsonDict, StrCollection
@@ -97,7 +91,7 @@ class ForeignKeyConstraint(Constraint):
     """
 
     referenced_table: str
-    columns: Sequence[Tuple[str, str]]
+    columns: Sequence[tuple[str, str]]
     deferred: bool
 
     def make_check_clause(self, table: str) -> str:
@@ -174,9 +168,9 @@ class _BackgroundUpdateContextManager:
 
     async def __aexit__(
         self,
-        exc_type: Optional[Type[BaseException]],
-        exc: Optional[BaseException],
-        tb: Optional[TracebackType],
+        exc_type: type[BaseException] | None,
+        exc: BaseException | None,
+        tb: TracebackType | None,
     ) -> None:
         pass
 
@@ -201,7 +195,7 @@ class BackgroundUpdatePerformance:
         self.avg_item_count += 0.1 * (item_count - self.avg_item_count)
         self.avg_duration_ms += 0.1 * (duration_ms - self.avg_duration_ms)
 
-    def average_items_per_ms(self) -> Optional[float]:
+    def average_items_per_ms(self) -> float | None:
         """An estimate of how long it takes to do a single update.
         Returns:
             A duration in ms as a float
@@ -217,7 +211,7 @@ class BackgroundUpdatePerformance:
             # changes in how long the update process takes.
             return float(self.avg_item_count) / float(self.avg_duration_ms)
 
-    def total_items_per_ms(self) -> Optional[float]:
+    def total_items_per_ms(self) -> float | None:
         """An estimate of how long it takes to do a single update.
         Returns:
             A duration in ms as a float
@@ -255,14 +249,14 @@ class BackgroundUpdater:
         self._database_name = database.name()
 
         # if a background update is currently running, its name.
-        self._current_background_update: Optional[str] = None
+        self._current_background_update: str | None = None
 
-        self._on_update_callback: Optional[ON_UPDATE_CALLBACK] = None
-        self._default_batch_size_callback: Optional[DEFAULT_BATCH_SIZE_CALLBACK] = None
-        self._min_batch_size_callback: Optional[MIN_BATCH_SIZE_CALLBACK] = None
+        self._on_update_callback: ON_UPDATE_CALLBACK | None = None
+        self._default_batch_size_callback: DEFAULT_BATCH_SIZE_CALLBACK | None = None
+        self._min_batch_size_callback: MIN_BATCH_SIZE_CALLBACK | None = None
 
-        self._background_update_performance: Dict[str, BackgroundUpdatePerformance] = {}
-        self._background_update_handlers: Dict[str, _BackgroundUpdateHandler] = {}
+        self._background_update_performance: dict[str, BackgroundUpdatePerformance] = {}
+        self._background_update_handlers: dict[str, _BackgroundUpdateHandler] = {}
         # TODO: all these bool flags make me feel icky---can we combine into a status
         # enum?
         self._all_done = False
@@ -285,6 +279,13 @@ class BackgroundUpdater:
         self.sleep_duration_ms = hs.config.background_updates.sleep_duration_ms
         self.sleep_enabled = hs.config.background_updates.sleep_enabled
 
+    def shutdown(self) -> None:
+        """
+        Stop any further background updates from happening.
+        """
+        self.enabled = False
+        self._background_update_handlers.clear()
+
     def get_status(self) -> UpdaterStatus:
         """An integer summarising the updater status. Used as a metric."""
         if self._aborted:
@@ -302,8 +303,8 @@ class BackgroundUpdater:
     def register_update_controller_callbacks(
         self,
         on_update: ON_UPDATE_CALLBACK,
-        default_batch_size: Optional[DEFAULT_BATCH_SIZE_CALLBACK] = None,
-        min_batch_size: Optional[DEFAULT_BATCH_SIZE_CALLBACK] = None,
+        default_batch_size: DEFAULT_BATCH_SIZE_CALLBACK | None = None,
+        min_batch_size: DEFAULT_BATCH_SIZE_CALLBACK | None = None,
     ) -> None:
         """Register callbacks from a module for each hook."""
         if self._on_update_callback is not None:
@@ -378,7 +379,7 @@ class BackgroundUpdater:
 
         return self.minimum_background_batch_size
 
-    def get_current_update(self) -> Optional[BackgroundUpdatePerformance]:
+    def get_current_update(self) -> BackgroundUpdatePerformance | None:
         """Returns the current background update, if any."""
 
         update_name = self._current_background_update
@@ -396,9 +397,8 @@ class BackgroundUpdater:
             # if we start a new background update, not all updates are done.
             self._all_done = False
             sleep = self.sleep_enabled
-            run_as_background_process(
+            self.hs.run_as_background_process(
                 "background_updates",
-                self.server_name,
                 self.run_background_updates,
                 sleep,
             )
@@ -525,14 +525,14 @@ class BackgroundUpdater:
             True if we have finished running all the background updates, otherwise False
         """
 
-        def get_background_updates_txn(txn: Cursor) -> List[Tuple[str, Optional[str]]]:
+        def get_background_updates_txn(txn: Cursor) -> list[tuple[str, str | None]]:
             txn.execute(
                 """
                 SELECT update_name, depends_on FROM background_updates
                 ORDER BY ordering, update_name
                 """
             )
-            return cast(List[Tuple[str, Optional[str]]], txn.fetchall())
+            return cast(list[tuple[str, str | None]], txn.fetchall())
 
         if not self._current_background_update:
             all_pending_updates = await self.db_pool.runInteraction(
@@ -668,10 +668,10 @@ class BackgroundUpdater:
         index_name: str,
         table: str,
         columns: Iterable[str],
-        where_clause: Optional[str] = None,
+        where_clause: str | None = None,
         unique: bool = False,
         psql_only: bool = False,
-        replaces_index: Optional[str] = None,
+        replaces_index: str | None = None,
     ) -> None:
         """Helper for store classes to do a background index addition
 
@@ -762,10 +762,10 @@ class BackgroundUpdater:
         index_name: str,
         table: str,
         columns: Iterable[str],
-        where_clause: Optional[str] = None,
+        where_clause: str | None = None,
         unique: bool = False,
         psql_only: bool = False,
-        replaces_index: Optional[str] = None,
+        replaces_index: str | None = None,
     ) -> None:
         """Add an index in the background.
 
@@ -861,7 +861,7 @@ class BackgroundUpdater:
                 c.execute(sql)
 
         if isinstance(self.db_pool.engine, engines.PostgresEngine):
-            runner: Optional[Callable[[LoggingDatabaseConnection], None]] = (
+            runner: Callable[[LoggingDatabaseConnection], None] | None = (
                 create_index_psql
             )
         elif psql_only:
@@ -953,14 +953,14 @@ class BackgroundUpdater:
         #      match the constraint.
         #   3. We try re-validating the constraint.
 
-        parsed_progress = ValidateConstraintProgress.parse_obj(progress)
+        parsed_progress = ValidateConstraintProgress.model_validate(progress)
 
         if parsed_progress.state == ValidateConstraintProgress.State.check:
             return_columns = ", ".join(unique_columns)
             order_columns = ", ".join(unique_columns)
 
             where_clause = ""
-            args: List[Any] = []
+            args: list[Any] = []
             if parsed_progress.lower_bound:
                 where_clause = f"""WHERE ({order_columns}) > ({", ".join("?" for _ in unique_columns)})"""
                 args.extend(parsed_progress.lower_bound)
diff --git a/synapse/storage/controllers/persist_events.py b/synapse/storage/controllers/persist_events.py
index 120934af57..2948227807 100644
--- a/synapse/storage/controllers/persist_events.py
+++ b/synapse/storage/controllers/persist_events.py
@@ -31,17 +31,10 @@ from typing import (
     Callable,
     ClassVar,
     Collection,
-    Deque,
-    Dict,
     Generator,
     Generic,
     Iterable,
-    List,
-    Optional,
-    Set,
-    Tuple,
     TypeVar,
-    Union,
 )
 
 import attr
@@ -62,7 +55,6 @@ from synapse.logging.opentracing import (
     trace,
 )
 from synapse.metrics import SERVER_NAME_LABEL
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.storage.controllers.state import StateStorageController
 from synapse.storage.databases import Databases
 from synapse.storage.databases.main.events import DeltaState
@@ -144,7 +136,7 @@ class _PersistEventsTask:
 
     name: ClassVar[str] = "persist_event_batch"  # used for opentracing
 
-    events_and_contexts: List[EventPersistencePair]
+    events_and_contexts: list[EventPersistencePair]
     backfilled: bool
 
     def try_merge(self, task: "_EventPersistQueueTask") -> bool:
@@ -170,7 +162,7 @@ class _UpdateCurrentStateTask:
         return isinstance(task, _UpdateCurrentStateTask)
 
 
-_EventPersistQueueTask = Union[_PersistEventsTask, _UpdateCurrentStateTask]
+_EventPersistQueueTask = _PersistEventsTask | _UpdateCurrentStateTask
 _PersistResult = TypeVar("_PersistResult")
 
 
@@ -179,7 +171,7 @@ class _EventPersistQueueItem(Generic[_PersistResult]):
     task: _EventPersistQueueTask
     deferred: ObservableDeferred[_PersistResult]
 
-    parent_opentracing_span_contexts: List = attr.ib(factory=list)
+    parent_opentracing_span_contexts: list = attr.ib(factory=list)
     """A list of opentracing spans waiting for this batch"""
 
     opentracing_span_context: Any = None
@@ -195,6 +187,7 @@ class _EventPeristenceQueue(Generic[_PersistResult]):
 
     def __init__(
         self,
+        hs: "HomeServer",
         server_name: str,
         per_item_callback: Callable[
             [str, _EventPersistQueueTask],
@@ -207,8 +200,9 @@ class _EventPeristenceQueue(Generic[_PersistResult]):
         and its result will be returned via the Deferreds returned from add_to_queue.
         """
         self.server_name = server_name
-        self._event_persist_queues: Dict[str, Deque[_EventPersistQueueItem]] = {}
-        self._currently_persisting_rooms: Set[str] = set()
+        self.hs = hs
+        self._event_persist_queues: dict[str, deque[_EventPersistQueueItem]] = {}
+        self._currently_persisting_rooms: set[str] = set()
         self._per_item_callback = per_item_callback
 
     async def add_to_queue(
@@ -311,7 +305,7 @@ class _EventPeristenceQueue(Generic[_PersistResult]):
                 self._currently_persisting_rooms.discard(room_id)
 
         # set handle_queue_loop off in the background
-        run_as_background_process("persist_events", self.server_name, handle_queue_loop)
+        self.hs.run_as_background_process("persist_events", handle_queue_loop)
 
     def _get_drainining_queue(
         self, room_id: str
@@ -354,7 +348,7 @@ class EventsPersistenceStorageController:
         self._instance_name = hs.get_instance_name()
         self.is_mine_id = hs.is_mine_id
         self._event_persist_queue = _EventPeristenceQueue(
-            self.server_name, self._process_event_persist_queue_task
+            hs, self.server_name, self._process_event_persist_queue_task
         )
         self._state_resolution_handler = hs.get_state_resolution_handler()
         self._state_controller = state_controller
@@ -364,7 +358,7 @@ class EventsPersistenceStorageController:
         self,
         room_id: str,
         task: _EventPersistQueueTask,
-    ) -> Dict[str, str]:
+    ) -> dict[str, str]:
         """Callback for the _event_persist_queue
 
         Returns:
@@ -393,7 +387,7 @@ class EventsPersistenceStorageController:
         self,
         events_and_contexts: Iterable[EventPersistencePair],
         backfilled: bool = False,
-    ) -> Tuple[List[EventBase], RoomStreamToken]:
+    ) -> tuple[list[EventBase], RoomStreamToken]:
         """
         Write events to the database
         Args:
@@ -413,8 +407,8 @@ class EventsPersistenceStorageController:
             PartialStateConflictError: if attempting to persist a partial state event in
                 a room that has been un-partial stated.
         """
-        event_ids: List[str] = []
-        partitioned: Dict[str, List[EventPersistencePair]] = {}
+        event_ids: list[str] = []
+        partitioned: dict[str, list[EventPersistencePair]] = {}
         for event, ctx in events_and_contexts:
             partitioned.setdefault(event.room_id, []).append((event, ctx))
             event_ids.append(event.event_id)
@@ -430,8 +424,8 @@ class EventsPersistenceStorageController:
         set_tag(SynapseTags.FUNC_ARG_PREFIX + "backfilled", str(backfilled))
 
         async def enqueue(
-            item: Tuple[str, List[EventPersistencePair]],
-        ) -> Dict[str, str]:
+            item: tuple[str, list[EventPersistencePair]],
+        ) -> dict[str, str]:
             room_id, evs_ctxs = item
             return await self._event_persist_queue.add_to_queue(
                 room_id,
@@ -446,7 +440,7 @@ class EventsPersistenceStorageController:
         #
         # Since we use `yieldable_gather_results` we need to merge the returned list
         # of dicts into one.
-        replaced_events: Dict[str, str] = {}
+        replaced_events: dict[str, str] = {}
         for d in ret_vals:
             replaced_events.update(d)
 
@@ -468,7 +462,7 @@ class EventsPersistenceStorageController:
     @trace
     async def persist_event(
         self, event: EventBase, context: EventContext, backfilled: bool = False
-    ) -> Tuple[EventBase, PersistedEventPosition, RoomStreamToken]:
+    ) -> tuple[EventBase, PersistedEventPosition, RoomStreamToken]:
         """
         Returns:
             The event, stream ordering of `event`, and the stream ordering of the
@@ -572,7 +566,7 @@ class EventsPersistenceStorageController:
 
     async def _persist_event_batch(
         self, room_id: str, task: _PersistEventsTask
-    ) -> Dict[str, str]:
+    ) -> dict[str, str]:
         """Callback for the _event_persist_queue
 
         Calculates the change to current state and forward extremities, and
@@ -591,7 +585,7 @@ class EventsPersistenceStorageController:
         events_and_contexts = task.events_and_contexts
         backfilled = task.backfilled
 
-        replaced_events: Dict[str, str] = {}
+        replaced_events: dict[str, str] = {}
         if not events_and_contexts:
             return replaced_events
 
@@ -677,8 +671,8 @@ class EventsPersistenceStorageController:
         return replaced_events
 
     async def _calculate_new_forward_extremities_and_state_delta(
-        self, room_id: str, ev_ctx_rm: List[EventPersistencePair]
-    ) -> Tuple[Optional[Set[str]], Optional[DeltaState]]:
+        self, room_id: str, ev_ctx_rm: list[EventPersistencePair]
+    ) -> tuple[set[str] | None, DeltaState | None]:
         """Calculates the new forward extremities and state delta for a room
         given events to persist.
 
@@ -802,9 +796,9 @@ class EventsPersistenceStorageController:
     async def _calculate_new_extremities(
         self,
         room_id: str,
-        event_contexts: List[EventPersistencePair],
+        event_contexts: list[EventPersistencePair],
         latest_event_ids: AbstractSet[str],
-    ) -> Set[str]:
+    ) -> set[str]:
         """Calculates the new forward extremities for a room given events to
         persist.
 
@@ -862,10 +856,10 @@ class EventsPersistenceStorageController:
     async def _get_new_state_after_events(
         self,
         room_id: str,
-        events_context: List[EventPersistencePair],
+        events_context: list[EventPersistencePair],
         old_latest_event_ids: AbstractSet[str],
-        new_latest_event_ids: Set[str],
-    ) -> Tuple[Optional[StateMap[str]], Optional[StateMap[str]], Set[str]]:
+        new_latest_event_ids: set[str],
+    ) -> tuple[StateMap[str] | None, StateMap[str] | None, set[str]]:
         """Calculate the current state dict after adding some new events to
         a room
 
@@ -1036,11 +1030,11 @@ class EventsPersistenceStorageController:
     async def _prune_extremities(
         self,
         room_id: str,
-        new_latest_event_ids: Set[str],
+        new_latest_event_ids: set[str],
         resolved_state_group: int,
-        event_id_to_state_group: Dict[str, int],
-        events_context: List[EventPersistencePair],
-    ) -> Set[str]:
+        event_id_to_state_group: dict[str, int],
+        events_context: list[EventPersistencePair],
+    ) -> set[str]:
         """See if we can prune any of the extremities after calculating the
         resolved state.
         """
@@ -1107,7 +1101,7 @@ class EventsPersistenceStorageController:
             # as a first cut.
             events_to_check: Collection[EventBase] = [event]
             while events_to_check:
-                new_events: Set[str] = set()
+                new_events: set[str] = set()
                 for event_to_check in events_to_check:
                     if self.is_mine_id(event_to_check.sender):
                         if event_to_check.type != EventTypes.Dummy:
@@ -1176,7 +1170,7 @@ class EventsPersistenceStorageController:
     async def _is_server_still_joined(
         self,
         room_id: str,
-        ev_ctx_rm: List[EventPersistencePair],
+        ev_ctx_rm: list[EventPersistencePair],
         delta: DeltaState,
     ) -> bool:
         """Check if the server will still be joined after the given events have
diff --git a/synapse/storage/controllers/purge_events.py b/synapse/storage/controllers/purge_events.py
index 14b37ac543..4ca3f8f4e1 100644
--- a/synapse/storage/controllers/purge_events.py
+++ b/synapse/storage/controllers/purge_events.py
@@ -25,8 +25,6 @@ from typing import (
     TYPE_CHECKING,
     Collection,
     Mapping,
-    Optional,
-    Set,
 )
 
 from synapse.logging.context import nested_logging_context
@@ -46,9 +44,8 @@ class PurgeEventsStorageController:
     """High level interface for purging rooms and event history."""
 
     def __init__(self, hs: "HomeServer", stores: Databases):
-        self.server_name = (
-            hs.hostname
-        )  # nb must be called this for @wrap_as_background_process
+        self.hs = hs  # nb must be called this for @wrap_as_background_process
+        self.server_name = hs.hostname
         self.stores = stores
 
         if hs.config.worker.run_background_tasks:
@@ -100,7 +97,7 @@ class PurgeEventsStorageController:
     async def _find_unreferenced_groups(
         self,
         state_groups: Collection[int],
-    ) -> Set[int]:
+    ) -> set[int]:
         """Used when purging history to figure out which state groups can be
         deleted.
 
@@ -317,7 +314,7 @@ class PurgeEventsStorageController:
         self,
         last_checked_state_group: int,
         batch_size: int,
-    ) -> tuple[Set[int], int, bool]:
+    ) -> tuple[set[int], int, bool]:
         """Used when deleting unreferenced state groups in the background to figure out
         which state groups can be deleted.
         To avoid increased DB usage due to de-deltaing state groups, this returns only
@@ -447,7 +444,7 @@ class PurgeEventsStorageController:
 
         # Remove state groups from deletion_candidates which are directly referenced or share a
         # future edge with a referenced state group within this batch.
-        def filter_reference_chains(group: Optional[int]) -> None:
+        def filter_reference_chains(group: int | None) -> None:
             while group is not None:
                 deletion_candidates.discard(group)
                 group = state_group_edges.get(group)
diff --git a/synapse/storage/controllers/state.py b/synapse/storage/controllers/state.py
index 66f3289d86..9c5e837ab0 100644
--- a/synapse/storage/controllers/state.py
+++ b/synapse/storage/controllers/state.py
@@ -25,14 +25,8 @@ from typing import (
     AbstractSet,
     Callable,
     Collection,
-    Dict,
-    FrozenSet,
     Iterable,
-    List,
     Mapping,
-    Optional,
-    Tuple,
-    Union,
 )
 
 from synapse.api.constants import EventTypes, Membership
@@ -69,8 +63,8 @@ class StateStorageController:
 
     def __init__(self, hs: "HomeServer", stores: "Databases"):
         self.server_name = hs.hostname  # nb must be called this for @cached
+        self.clock = hs.get_clock()
         self._is_mine_id = hs.is_mine_id
-        self._clock = hs.get_clock()
         self.stores = stores
         self._partial_state_events_tracker = PartialStateEventsTracker(stores.main)
         self._partial_state_room_tracker = PartialCurrentStateTracker(stores.main)
@@ -78,7 +72,7 @@ class StateStorageController:
         # Used by `_get_joined_hosts` to ensure only one thing mutates the cache
         # at a time. Keyed by room_id.
         self._joined_host_linearizer = Linearizer(
-            name="_JoinedHostsCache", clock=self._clock
+            name="_JoinedHostsCache", clock=self.clock
         )
 
     def notify_event_un_partial_stated(self, event_id: str) -> None:
@@ -95,7 +89,7 @@ class StateStorageController:
     @tag_args
     async def get_state_group_delta(
         self, state_group: int
-    ) -> Tuple[Optional[int], Optional[StateMap[str]]]:
+    ) -> tuple[int | None, StateMap[str] | None]:
         """Given a state group try to return a previous group and a delta between
         the old and the new.
 
@@ -114,7 +108,7 @@ class StateStorageController:
     @tag_args
     async def get_state_groups_ids(
         self, _room_id: str, event_ids: Collection[str], await_full_state: bool = True
-    ) -> Dict[int, MutableStateMap[str]]:
+    ) -> dict[int, MutableStateMap[str]]:
         """Get the event IDs of all the state for the state groups for the given events
 
         Args:
@@ -145,7 +139,7 @@ class StateStorageController:
     @trace
     @tag_args
     async def get_state_ids_for_group(
-        self, state_group: int, state_filter: Optional[StateFilter] = None
+        self, state_group: int, state_filter: StateFilter | None = None
     ) -> StateMap[str]:
         """Get the event IDs of all the state in the given state group
 
@@ -164,7 +158,7 @@ class StateStorageController:
     @tag_args
     async def get_state_groups(
         self, room_id: str, event_ids: Collection[str]
-    ) -> Dict[int, List[EventBase]]:
+    ) -> dict[int, list[EventBase]]:
         """Get the state groups for the given list of event_ids
 
         Args:
@@ -200,8 +194,8 @@ class StateStorageController:
     @trace
     @tag_args
     async def _get_state_groups_from_groups(
-        self, groups: List[int], state_filter: StateFilter
-    ) -> Dict[int, StateMap[str]]:
+        self, groups: list[int], state_filter: StateFilter
+    ) -> dict[int, StateMap[str]]:
         """Returns the state groups for a given set of groups, filtering on
         types of state events.
 
@@ -221,8 +215,8 @@ class StateStorageController:
     @trace
     @tag_args
     async def get_state_for_events(
-        self, event_ids: Collection[str], state_filter: Optional[StateFilter] = None
-    ) -> Dict[str, StateMap[EventBase]]:
+        self, event_ids: Collection[str], state_filter: StateFilter | None = None
+    ) -> dict[str, StateMap[EventBase]]:
         """Given a list of event_ids and type tuples, return a list of state
         dicts for each event.
 
@@ -275,9 +269,9 @@ class StateStorageController:
     async def get_state_ids_for_events(
         self,
         event_ids: Collection[str],
-        state_filter: Optional[StateFilter] = None,
+        state_filter: StateFilter | None = None,
         await_full_state: bool = True,
-    ) -> Dict[str, StateMap[str]]:
+    ) -> dict[str, StateMap[str]]:
         """
         Get the room states after each of a list of events.
 
@@ -326,7 +320,7 @@ class StateStorageController:
     @trace
     @tag_args
     async def get_state_for_event(
-        self, event_id: str, state_filter: Optional[StateFilter] = None
+        self, event_id: str, state_filter: StateFilter | None = None
     ) -> StateMap[EventBase]:
         """
         Get the state dict corresponding to a particular event
@@ -353,7 +347,7 @@ class StateStorageController:
     async def get_state_ids_for_event(
         self,
         event_id: str,
-        state_filter: Optional[StateFilter] = None,
+        state_filter: StateFilter | None = None,
         await_full_state: bool = True,
     ) -> StateMap[str]:
         """
@@ -386,7 +380,7 @@ class StateStorageController:
     async def get_state_after_event(
         self,
         event_id: str,
-        state_filter: Optional[StateFilter] = None,
+        state_filter: StateFilter | None = None,
         await_full_state: bool = True,
     ) -> StateMap[str]:
         """
@@ -427,7 +421,7 @@ class StateStorageController:
         self,
         room_id: str,
         stream_position: StreamToken,
-        state_filter: Optional[StateFilter] = None,
+        state_filter: StateFilter | None = None,
         await_full_state: bool = True,
     ) -> StateMap[str]:
         """Get the room state at a particular stream position
@@ -483,7 +477,7 @@ class StateStorageController:
         self,
         room_id: str,
         stream_position: StreamToken,
-        state_filter: Optional[StateFilter] = None,
+        state_filter: StateFilter | None = None,
         await_full_state: bool = True,
     ) -> StateMap[EventBase]:
         """Same as `get_state_ids_at` but also fetches the events"""
@@ -504,8 +498,8 @@ class StateStorageController:
     @trace
     @tag_args
     async def get_state_for_groups(
-        self, groups: Iterable[int], state_filter: Optional[StateFilter] = None
-    ) -> Dict[int, MutableStateMap[str]]:
+        self, groups: Iterable[int], state_filter: StateFilter | None = None
+    ) -> dict[int, MutableStateMap[str]]:
         """Gets the state at each of a list of state groups, optionally
         filtering by type/state_key
 
@@ -550,9 +544,9 @@ class StateStorageController:
         self,
         event_id: str,
         room_id: str,
-        prev_group: Optional[int],
-        delta_ids: Optional[StateMap[str]],
-        current_state_ids: Optional[StateMap[str]],
+        prev_group: int | None,
+        delta_ids: StateMap[str] | None,
+        current_state_ids: StateMap[str] | None,
     ) -> int:
         """Store a new set of state, returning a newly assigned state group.
 
@@ -579,9 +573,9 @@ class StateStorageController:
     async def get_current_state_ids(
         self,
         room_id: str,
-        state_filter: Optional[StateFilter] = None,
+        state_filter: StateFilter | None = None,
         await_full_state: bool = True,
-        on_invalidate: Optional[Callable[[], None]] = None,
+        on_invalidate: Callable[[], None] | None = None,
     ) -> StateMap[str]:
         """Get the current state event ids for a room based on the
         current_state_events table.
@@ -618,7 +612,7 @@ class StateStorageController:
 
     @trace
     @tag_args
-    async def get_canonical_alias_for_room(self, room_id: str) -> Optional[str]:
+    async def get_canonical_alias_for_room(self, room_id: str) -> str | None:
         """Get canonical alias for room, if any
 
         Args:
@@ -643,9 +637,7 @@ class StateStorageController:
         return event.content.get("alias")
 
     @cached()
-    async def get_server_acl_for_room(
-        self, room_id: str
-    ) -> Optional[ServerAclEvaluator]:
+    async def get_server_acl_for_room(self, room_id: str) -> ServerAclEvaluator | None:
         """Get the server ACL evaluator for room, if any
 
         This does up-front parsing of the content to ignore bad data and pre-compile
@@ -671,7 +663,7 @@ class StateStorageController:
     @tag_args
     async def get_current_state_deltas(
         self, prev_stream_id: int, max_stream_id: int
-    ) -> Tuple[int, List[StateDelta]]:
+    ) -> tuple[int, list[StateDelta]]:
         """Fetch a list of room state changes since the given stream id
 
         Args:
@@ -699,7 +691,7 @@ class StateStorageController:
     async def get_current_state(
         self,
         room_id: str,
-        state_filter: Optional[StateFilter] = None,
+        state_filter: StateFilter | None = None,
         await_full_state: bool = True,
     ) -> StateMap[EventBase]:
         """Same as `get_current_state_ids` but also fetches the events"""
@@ -721,7 +713,7 @@ class StateStorageController:
     @tag_args
     async def get_current_state_event(
         self, room_id: str, event_type: str, state_key: str
-    ) -> Optional[EventBase]:
+    ) -> EventBase | None:
         """Get the current state event for the given type/state_key."""
 
         key = (event_type, state_key)
@@ -745,7 +737,7 @@ class StateStorageController:
 
     @trace
     @tag_args
-    async def get_current_hosts_in_room_ordered(self, room_id: str) -> Tuple[str, ...]:
+    async def get_current_hosts_in_room_ordered(self, room_id: str) -> tuple[str, ...]:
         """Get current hosts in room based on current state.
 
         Blocks until we have full state for the given room. This only happens for rooms
@@ -807,8 +799,8 @@ class StateStorageController:
 
     async def get_joined_hosts(
         self, room_id: str, state_entry: "_StateCacheEntry"
-    ) -> FrozenSet[str]:
-        state_group: Union[object, int] = state_entry.state_group
+    ) -> frozenset[str]:
+        state_group: object | int = state_entry.state_group
         if not state_group:
             # If state_group is None it means it has yet to be assigned a
             # state group, i.e. we need to make sure that calls with a state_group
@@ -817,9 +809,7 @@ class StateStorageController:
             state_group = object()
 
         assert state_group is not None
-        with Measure(
-            self._clock, name="get_joined_hosts", server_name=self.server_name
-        ):
+        with Measure(self.clock, name="get_joined_hosts", server_name=self.server_name):
             return await self._get_joined_hosts(
                 room_id, state_group, state_entry=state_entry
             )
@@ -828,9 +818,9 @@ class StateStorageController:
     async def _get_joined_hosts(
         self,
         room_id: str,
-        state_group: Union[object, int],
+        state_group: object | int,
         state_entry: "_StateCacheEntry",
-    ) -> FrozenSet[str]:
+    ) -> frozenset[str]:
         # We don't use `state_group`, it's there so that we can cache based on
         # it. However, its important that its never None, since two
         # current_state's with a state_group of None are likely to be different.
diff --git a/synapse/storage/controllers/stats.py b/synapse/storage/controllers/stats.py
index 9445a86240..18e27e0878 100644
--- a/synapse/storage/controllers/stats.py
+++ b/synapse/storage/controllers/stats.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Collection, Counter, List, Tuple
+from typing import TYPE_CHECKING, Collection, Counter
 
 from synapse.api.errors import SynapseError
 from synapse.storage.database import LoggingTransaction
@@ -39,7 +39,7 @@ class StatsController:
     def __init__(self, hs: "HomeServer", stores: Databases):
         self.stores = stores
 
-    async def get_room_db_size_estimate(self) -> List[Tuple[str, int]]:
+    async def get_room_db_size_estimate(self) -> list[tuple[str, int]]:
         """Get an estimate of the largest rooms and how much database space they
         use, in bytes.
 
diff --git a/synapse/storage/database.py b/synapse/storage/database.py
index 249a0a933c..3d351e8aea 100644
--- a/synapse/storage/database.py
+++ b/synapse/storage/database.py
@@ -31,16 +31,11 @@ from typing import (
     Awaitable,
     Callable,
     Collection,
-    Dict,
     Iterable,
     Iterator,
-    List,
     Literal,
     Mapping,
-    Optional,
     Sequence,
-    Tuple,
-    Type,
     TypeVar,
     cast,
     overload,
@@ -62,7 +57,6 @@ from synapse.logging.context import (
     make_deferred_yieldable,
 )
 from synapse.metrics import SERVER_NAME_LABEL, register_threadpool
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.storage.background_updates import BackgroundUpdater
 from synapse.storage.engines import BaseDatabaseEngine, PostgresEngine, Sqlite3Engine
 from synapse.storage.types import Connection, Cursor, SQLQueryParameters
@@ -218,10 +212,10 @@ class LoggingDatabaseConnection:
     def cursor(
         self,
         *,
-        txn_name: Optional[str] = None,
-        after_callbacks: Optional[List["_CallbackListEntry"]] = None,
-        async_after_callbacks: Optional[List["_AsyncCallbackListEntry"]] = None,
-        exception_callbacks: Optional[List["_CallbackListEntry"]] = None,
+        txn_name: str | None = None,
+        after_callbacks: list["_CallbackListEntry"] | None = None,
+        async_after_callbacks: list["_AsyncCallbackListEntry"] | None = None,
+        exception_callbacks: list["_CallbackListEntry"] | None = None,
     ) -> "LoggingTransaction":
         if not txn_name:
             txn_name = self.default_txn_name
@@ -251,10 +245,10 @@ class LoggingDatabaseConnection:
 
     def __exit__(
         self,
-        exc_type: Optional[Type[BaseException]],
-        exc_value: Optional[BaseException],
-        traceback: Optional[types.TracebackType],
-    ) -> Optional[bool]:
+        exc_type: type[BaseException] | None,
+        exc_value: BaseException | None,
+        traceback: types.TracebackType | None,
+    ) -> bool | None:
         return self.conn.__exit__(exc_type, exc_value, traceback)
 
     # Proxy through any unknown lookups to the DB conn class.
@@ -263,9 +257,9 @@ class LoggingDatabaseConnection:
 
 
 # The type of entry which goes on our after_callbacks and exception_callbacks lists.
-_CallbackListEntry = Tuple[Callable[..., object], Tuple[object, ...], Dict[str, object]]
-_AsyncCallbackListEntry = Tuple[
-    Callable[..., Awaitable], Tuple[object, ...], Dict[str, object]
+_CallbackListEntry = tuple[Callable[..., object], tuple[object, ...], dict[str, object]]
+_AsyncCallbackListEntry = tuple[
+    Callable[..., Awaitable], tuple[object, ...], dict[str, object]
 ]
 
 P = ParamSpec("P")
@@ -312,9 +306,9 @@ class LoggingTransaction:
         name: str,
         server_name: str,
         database_engine: BaseDatabaseEngine,
-        after_callbacks: Optional[List[_CallbackListEntry]] = None,
-        async_after_callbacks: Optional[List[_AsyncCallbackListEntry]] = None,
-        exception_callbacks: Optional[List[_CallbackListEntry]] = None,
+        after_callbacks: list[_CallbackListEntry] | None = None,
+        async_after_callbacks: list[_AsyncCallbackListEntry] | None = None,
+        exception_callbacks: list[_CallbackListEntry] | None = None,
     ):
         self.txn = txn
         self.name = name
@@ -384,16 +378,16 @@ class LoggingTransaction:
         assert self.exception_callbacks is not None
         self.exception_callbacks.append((callback, args, kwargs))
 
-    def fetchone(self) -> Optional[Tuple]:
+    def fetchone(self) -> tuple | None:
         return self.txn.fetchone()
 
-    def fetchmany(self, size: Optional[int] = None) -> List[Tuple]:
+    def fetchmany(self, size: int | None = None) -> list[tuple]:
         return self.txn.fetchmany(size=size)
 
-    def fetchall(self) -> List[Tuple]:
+    def fetchall(self) -> list[tuple]:
         return self.txn.fetchall()
 
-    def __iter__(self) -> Iterator[Tuple]:
+    def __iter__(self) -> Iterator[tuple]:
         return self.txn.__iter__()
 
     @property
@@ -403,7 +397,7 @@ class LoggingTransaction:
     @property
     def description(
         self,
-    ) -> Optional[Sequence[Any]]:
+    ) -> Sequence[Any] | None:
         return self.txn.description
 
     def execute_batch(self, sql: str, args: Iterable[Iterable[Any]]) -> None:
@@ -434,9 +428,9 @@ class LoggingTransaction:
         self,
         sql: str,
         values: Iterable[Iterable[Any]],
-        template: Optional[str] = None,
+        template: str | None = None,
         fetch: bool = True,
-    ) -> List[Tuple]:
+    ) -> list[tuple]:
         """Corresponds to psycopg2.extras.execute_values. Only available when
         using postgres.
 
@@ -541,17 +535,17 @@ class LoggingTransaction:
 
     def __exit__(
         self,
-        exc_type: Optional[Type[BaseException]],
-        exc_value: Optional[BaseException],
-        traceback: Optional[types.TracebackType],
+        exc_type: type[BaseException] | None,
+        exc_value: BaseException | None,
+        traceback: types.TracebackType | None,
     ) -> None:
         self.close()
 
 
 class PerformanceCounters:
     def __init__(self) -> None:
-        self.current_counters: Dict[str, Tuple[int, float]] = {}
-        self.previous_counters: Dict[str, Tuple[int, float]] = {}
+        self.current_counters: dict[str, tuple[int, float]] = {}
+        self.previous_counters: dict[str, tuple[int, float]] = {}
 
     def update(self, key: str, duration_secs: float) -> None:
         count, cum_time = self.current_counters.get(key, (0, 0.0))
@@ -617,7 +611,7 @@ class DatabasePool:
         self._previous_loop_ts = 0.0
 
         # Transaction counter: key is the twisted thread id, value is the current count
-        self._txn_counters: Dict[int, int] = defaultdict(int)
+        self._txn_counters: dict[int, int] = defaultdict(int)
 
         # TODO(paul): These can eventually be removed once the metrics code
         #   is running in mainline, and we have some nice monitoring frontends
@@ -638,12 +632,17 @@ class DatabasePool:
         # background updates of tables that aren't safe to update.
         self._clock.call_later(
             0.0,
-            run_as_background_process,
+            self.hs.run_as_background_process,
             "upsert_safety_check",
-            self.server_name,
             self._check_safe_to_upsert,
         )
 
+    def stop_background_updates(self) -> None:
+        """
+        Stops the database from running any further background updates.
+        """
+        self.updates.shutdown()
+
     def name(self) -> str:
         "Return the name of this database"
         return self._database_config.name
@@ -662,7 +661,7 @@ class DatabasePool:
         If the background updates have not completed, wait 15 sec and check again.
         """
         updates = cast(
-            List[Tuple[str]],
+            list[tuple[str]],
             await self.simple_select_list(
                 "background_updates",
                 keyvalues=None,
@@ -681,9 +680,8 @@ class DatabasePool:
         if background_update_names:
             self._clock.call_later(
                 15.0,
-                run_as_background_process,
+                self.hs.run_as_background_process,
                 "upsert_safety_check",
-                self.server_name,
                 self._check_safe_to_upsert,
             )
 
@@ -714,9 +712,9 @@ class DatabasePool:
         self,
         conn: LoggingDatabaseConnection,
         desc: str,
-        after_callbacks: List[_CallbackListEntry],
-        async_after_callbacks: List[_AsyncCallbackListEntry],
-        exception_callbacks: List[_CallbackListEntry],
+        after_callbacks: list[_CallbackListEntry],
+        async_after_callbacks: list[_AsyncCallbackListEntry],
+        exception_callbacks: list[_CallbackListEntry],
         func: Callable[Concatenate[LoggingTransaction, P], R],
         *args: P.args,
         **kwargs: P.kwargs,
@@ -921,7 +919,7 @@ class DatabasePool:
         func: Callable[..., R],
         *args: Any,
         db_autocommit: bool = False,
-        isolation_level: Optional[int] = None,
+        isolation_level: int | None = None,
         **kwargs: Any,
     ) -> R:
         """Starts a transaction on the database and runs a given function
@@ -953,9 +951,9 @@ class DatabasePool:
         """
 
         async def _runInteraction() -> R:
-            after_callbacks: List[_CallbackListEntry] = []
-            async_after_callbacks: List[_AsyncCallbackListEntry] = []
-            exception_callbacks: List[_CallbackListEntry] = []
+            after_callbacks: list[_CallbackListEntry] = []
+            async_after_callbacks: list[_AsyncCallbackListEntry] = []
+            exception_callbacks: list[_CallbackListEntry] = []
 
             if not current_context():
                 logger.warning("Starting db txn '%s' from sentinel context", desc)
@@ -1003,7 +1001,7 @@ class DatabasePool:
         func: Callable[Concatenate[LoggingDatabaseConnection, P], R],
         *args: Any,
         db_autocommit: bool = False,
-        isolation_level: Optional[int] = None,
+        isolation_level: int | None = None,
         **kwargs: Any,
     ) -> R:
         """Wraps the .runWithConnection() method on the underlying db_pool.
@@ -1102,7 +1100,7 @@ class DatabasePool:
             self._db_pool.runWithConnection(inner_func, *args, **kwargs)
         )
 
-    async def execute(self, desc: str, query: str, *args: Any) -> List[Tuple[Any, ...]]:
+    async def execute(self, desc: str, query: str, *args: Any) -> list[tuple[Any, ...]]:
         """Runs a single query for a result set.
 
         Args:
@@ -1113,7 +1111,7 @@ class DatabasePool:
             The result of decoder(results)
         """
 
-        def interaction(txn: LoggingTransaction) -> List[Tuple[Any, ...]]:
+        def interaction(txn: LoggingTransaction) -> list[tuple[Any, ...]]:
             txn.execute(query, args)
             return txn.fetchall()
 
@@ -1125,7 +1123,7 @@ class DatabasePool:
     async def simple_insert(
         self,
         table: str,
-        values: Dict[str, Any],
+        values: dict[str, Any],
         desc: str = "simple_insert",
     ) -> None:
         """Executes an INSERT query on the named table.
@@ -1139,7 +1137,7 @@ class DatabasePool:
 
     @staticmethod
     def simple_insert_txn(
-        txn: LoggingTransaction, table: str, values: Dict[str, Any]
+        txn: LoggingTransaction, table: str, values: dict[str, Any]
     ) -> None:
         keys, vals = zip(*values.items())
 
@@ -1155,43 +1153,24 @@ class DatabasePool:
     def simple_insert_returning_txn(
         txn: LoggingTransaction,
         table: str,
-        values: Dict[str, Any],
+        values: dict[str, Any],
         returning: StrCollection,
-    ) -> Tuple[Any, ...]:
+    ) -> tuple[Any, ...]:
         """Executes a `INSERT INTO... RETURNING...` statement (or equivalent for
         SQLite versions that don't support it).
         """
 
-        if txn.database_engine.supports_returning:
-            sql = "INSERT INTO %s (%s) VALUES(%s) RETURNING %s" % (
-                table,
-                ", ".join(k for k in values.keys()),
-                ", ".join("?" for _ in values.keys()),
-                ", ".join(k for k in returning),
-            )
+        sql = "INSERT INTO %s (%s) VALUES(%s) RETURNING %s" % (
+            table,
+            ", ".join(k for k in values.keys()),
+            ", ".join("?" for _ in values.keys()),
+            ", ".join(k for k in returning),
+        )
 
-            txn.execute(sql, list(values.values()))
-            row = txn.fetchone()
-            assert row is not None
-            return row
-        else:
-            # For old versions of SQLite we do a standard insert and then can
-            # use `last_insert_rowid` to get at the row we just inserted
-            DatabasePool.simple_insert_txn(
-                txn,
-                table=table,
-                values=values,
-            )
-            txn.execute("SELECT last_insert_rowid()")
-            row = txn.fetchone()
-            assert row is not None
-            (rowid,) = row
-
-            row = DatabasePool.simple_select_one_txn(
-                txn, table=table, keyvalues={"rowid": rowid}, retcols=returning
-            )
-            assert row is not None
-            return row
+        txn.execute(sql, list(values.values()))
+        row = txn.fetchone()
+        assert row is not None
+        return row
 
     async def simple_insert_many(
         self,
@@ -1258,10 +1237,10 @@ class DatabasePool:
     async def simple_upsert(
         self,
         table: str,
-        keyvalues: Dict[str, Any],
-        values: Dict[str, Any],
-        insertion_values: Optional[Dict[str, Any]] = None,
-        where_clause: Optional[str] = None,
+        keyvalues: dict[str, Any],
+        values: dict[str, Any],
+        insertion_values: dict[str, Any] | None = None,
+        where_clause: str | None = None,
         desc: str = "simple_upsert",
     ) -> bool:
         """Insert a row with values + insertion_values; on conflict, update with values.
@@ -1354,8 +1333,8 @@ class DatabasePool:
         table: str,
         keyvalues: Mapping[str, Any],
         values: Mapping[str, Any],
-        insertion_values: Optional[Mapping[str, Any]] = None,
-        where_clause: Optional[str] = None,
+        insertion_values: Mapping[str, Any] | None = None,
+        where_clause: str | None = None,
     ) -> bool:
         """
         Pick the UPSERT method which works best on the platform. Either the
@@ -1399,8 +1378,8 @@ class DatabasePool:
         table: str,
         keyvalues: Mapping[str, Any],
         values: Mapping[str, Any],
-        insertion_values: Optional[Mapping[str, Any]] = None,
-        where_clause: Optional[str] = None,
+        insertion_values: Mapping[str, Any] | None = None,
+        where_clause: str | None = None,
         lock: bool = True,
     ) -> bool:
         """
@@ -1460,7 +1439,7 @@ class DatabasePool:
                 return True
 
         # We didn't find any existing rows, so insert a new one
-        allvalues: Dict[str, Any] = {}
+        allvalues: dict[str, Any] = {}
         allvalues.update(keyvalues)
         allvalues.update(values)
         allvalues.update(insertion_values)
@@ -1480,8 +1459,8 @@ class DatabasePool:
         table: str,
         keyvalues: Mapping[str, Any],
         values: Mapping[str, Any],
-        insertion_values: Optional[Mapping[str, Any]] = None,
-        where_clause: Optional[str] = None,
+        insertion_values: Mapping[str, Any] | None = None,
+        where_clause: str | None = None,
     ) -> bool:
         """
         Use the native UPSERT functionality in PostgreSQL.
@@ -1497,7 +1476,7 @@ class DatabasePool:
             Returns True if a row was inserted or updated (i.e. if `values` is
             not empty then this always returns True)
         """
-        allvalues: Dict[str, Any] = {}
+        allvalues: dict[str, Any] = {}
         allvalues.update(keyvalues)
         allvalues.update(insertion_values or {})
 
@@ -1691,7 +1670,7 @@ class DatabasePool:
             value_values: A list of each row's value column values.
                 Ignored if value_names is empty.
         """
-        allnames: List[str] = []
+        allnames: list[str] = []
         allnames.extend(key_names)
         allnames.extend(value_names)
 
@@ -1734,30 +1713,30 @@ class DatabasePool:
     async def simple_select_one(
         self,
         table: str,
-        keyvalues: Dict[str, Any],
+        keyvalues: dict[str, Any],
         retcols: Collection[str],
         allow_none: Literal[False] = False,
         desc: str = "simple_select_one",
-    ) -> Tuple[Any, ...]: ...
+    ) -> tuple[Any, ...]: ...
 
     @overload
     async def simple_select_one(
         self,
         table: str,
-        keyvalues: Dict[str, Any],
+        keyvalues: dict[str, Any],
         retcols: Collection[str],
         allow_none: Literal[True] = True,
         desc: str = "simple_select_one",
-    ) -> Optional[Tuple[Any, ...]]: ...
+    ) -> tuple[Any, ...] | None: ...
 
     async def simple_select_one(
         self,
         table: str,
-        keyvalues: Dict[str, Any],
+        keyvalues: dict[str, Any],
         retcols: Collection[str],
         allow_none: bool = False,
         desc: str = "simple_select_one",
-    ) -> Optional[Tuple[Any, ...]]:
+    ) -> tuple[Any, ...] | None:
         """Executes a SELECT query on the named table, which is expected to
         return a single row, returning multiple columns from it.
 
@@ -1783,7 +1762,7 @@ class DatabasePool:
     async def simple_select_one_onecol(
         self,
         table: str,
-        keyvalues: Dict[str, Any],
+        keyvalues: dict[str, Any],
         retcol: str,
         allow_none: Literal[False] = False,
         desc: str = "simple_select_one_onecol",
@@ -1793,20 +1772,20 @@ class DatabasePool:
     async def simple_select_one_onecol(
         self,
         table: str,
-        keyvalues: Dict[str, Any],
+        keyvalues: dict[str, Any],
         retcol: str,
         allow_none: Literal[True] = True,
         desc: str = "simple_select_one_onecol",
-    ) -> Optional[Any]: ...
+    ) -> Any | None: ...
 
     async def simple_select_one_onecol(
         self,
         table: str,
-        keyvalues: Dict[str, Any],
+        keyvalues: dict[str, Any],
         retcol: str,
         allow_none: bool = False,
         desc: str = "simple_select_one_onecol",
-    ) -> Optional[Any]:
+    ) -> Any | None:
         """Executes a SELECT query on the named table, which is expected to
         return a single row, returning a single column from it.
 
@@ -1834,7 +1813,7 @@ class DatabasePool:
         cls,
         txn: LoggingTransaction,
         table: str,
-        keyvalues: Dict[str, Any],
+        keyvalues: dict[str, Any],
         retcol: str,
         allow_none: Literal[False] = False,
     ) -> Any: ...
@@ -1845,20 +1824,20 @@ class DatabasePool:
         cls,
         txn: LoggingTransaction,
         table: str,
-        keyvalues: Dict[str, Any],
+        keyvalues: dict[str, Any],
         retcol: str,
         allow_none: Literal[True] = True,
-    ) -> Optional[Any]: ...
+    ) -> Any | None: ...
 
     @classmethod
     def simple_select_one_onecol_txn(
         cls,
         txn: LoggingTransaction,
         table: str,
-        keyvalues: Dict[str, Any],
+        keyvalues: dict[str, Any],
         retcol: str,
         allow_none: bool = False,
-    ) -> Optional[Any]:
+    ) -> Any | None:
         ret = cls.simple_select_onecol_txn(
             txn, table=table, keyvalues=keyvalues, retcol=retcol
         )
@@ -1875,9 +1854,9 @@ class DatabasePool:
     def simple_select_onecol_txn(
         txn: LoggingTransaction,
         table: str,
-        keyvalues: Dict[str, Any],
+        keyvalues: dict[str, Any],
         retcol: str,
-    ) -> List[Any]:
+    ) -> list[Any]:
         sql = ("SELECT %(retcol)s FROM %(table)s") % {"retcol": retcol, "table": table}
 
         if keyvalues:
@@ -1891,10 +1870,10 @@ class DatabasePool:
     async def simple_select_onecol(
         self,
         table: str,
-        keyvalues: Optional[Dict[str, Any]],
+        keyvalues: dict[str, Any] | None,
         retcol: str,
         desc: str = "simple_select_onecol",
-    ) -> List[Any]:
+    ) -> list[Any]:
         """Executes a SELECT query on the named table, which returns a list
         comprising of the values of the named column from the selected rows.
 
@@ -1919,10 +1898,10 @@ class DatabasePool:
     async def simple_select_list(
         self,
         table: str,
-        keyvalues: Optional[Dict[str, Any]],
+        keyvalues: dict[str, Any] | None,
         retcols: Collection[str],
         desc: str = "simple_select_list",
-    ) -> List[Tuple[Any, ...]]:
+    ) -> list[tuple[Any, ...]]:
         """Executes a SELECT query on the named table, which may return zero or
         more rows, returning the result as a list of tuples.
 
@@ -1951,9 +1930,9 @@ class DatabasePool:
         cls,
         txn: LoggingTransaction,
         table: str,
-        keyvalues: Optional[Dict[str, Any]],
+        keyvalues: dict[str, Any] | None,
         retcols: Iterable[str],
-    ) -> List[Tuple[Any, ...]]:
+    ) -> list[tuple[Any, ...]]:
         """Executes a SELECT query on the named table, which may return zero or
         more rows, returning the result as a list of tuples.
 
@@ -1987,10 +1966,10 @@ class DatabasePool:
         column: str,
         iterable: Iterable[Any],
         retcols: Collection[str],
-        keyvalues: Optional[Dict[str, Any]] = None,
+        keyvalues: dict[str, Any] | None = None,
         desc: str = "simple_select_many_batch",
         batch_size: int = 100,
-    ) -> List[Tuple[Any, ...]]:
+    ) -> list[tuple[Any, ...]]:
         """Executes a SELECT query on the named table, which may return zero or
         more rows.
 
@@ -2010,7 +1989,7 @@ class DatabasePool:
         """
         keyvalues = keyvalues or {}
 
-        results: List[Tuple[Any, ...]] = []
+        results: list[tuple[Any, ...]] = []
 
         for chunk in batch_iter(iterable, batch_size):
             rows = await self.runInteraction(
@@ -2035,9 +2014,9 @@ class DatabasePool:
         table: str,
         column: str,
         iterable: Collection[Any],
-        keyvalues: Dict[str, Any],
+        keyvalues: dict[str, Any],
         retcols: Iterable[str],
-    ) -> List[Tuple[Any, ...]]:
+    ) -> list[tuple[Any, ...]]:
         """Executes a SELECT query on the named table, which may return zero or
         more rows.
 
@@ -2077,8 +2056,8 @@ class DatabasePool:
     async def simple_update(
         self,
         table: str,
-        keyvalues: Dict[str, Any],
-        updatevalues: Dict[str, Any],
+        keyvalues: dict[str, Any],
+        updatevalues: dict[str, Any],
         desc: str,
     ) -> int:
         """
@@ -2214,8 +2193,8 @@ class DatabasePool:
     async def simple_update_one(
         self,
         table: str,
-        keyvalues: Dict[str, Any],
-        updatevalues: Dict[str, Any],
+        keyvalues: dict[str, Any],
+        updatevalues: dict[str, Any],
         desc: str = "simple_update_one",
     ) -> None:
         """Executes an UPDATE query on the named table, setting new values for
@@ -2241,8 +2220,8 @@ class DatabasePool:
         cls,
         txn: LoggingTransaction,
         table: str,
-        keyvalues: Dict[str, Any],
-        updatevalues: Dict[str, Any],
+        keyvalues: dict[str, Any],
+        updatevalues: dict[str, Any],
     ) -> None:
         rowcount = cls.simple_update_txn(txn, table, keyvalues, updatevalues)
 
@@ -2256,29 +2235,29 @@ class DatabasePool:
     def simple_select_one_txn(
         txn: LoggingTransaction,
         table: str,
-        keyvalues: Dict[str, Any],
+        keyvalues: dict[str, Any],
         retcols: Collection[str],
         allow_none: Literal[False] = False,
-    ) -> Tuple[Any, ...]: ...
+    ) -> tuple[Any, ...]: ...
 
     @overload
     @staticmethod
     def simple_select_one_txn(
         txn: LoggingTransaction,
         table: str,
-        keyvalues: Dict[str, Any],
+        keyvalues: dict[str, Any],
         retcols: Collection[str],
         allow_none: Literal[True] = True,
-    ) -> Optional[Tuple[Any, ...]]: ...
+    ) -> tuple[Any, ...] | None: ...
 
     @staticmethod
     def simple_select_one_txn(
         txn: LoggingTransaction,
         table: str,
-        keyvalues: Dict[str, Any],
+        keyvalues: dict[str, Any],
         retcols: Collection[str],
         allow_none: bool = False,
-    ) -> Optional[Tuple[Any, ...]]:
+    ) -> tuple[Any, ...] | None:
         select_sql = "SELECT %s FROM %s" % (", ".join(retcols), table)
 
         if keyvalues:
@@ -2299,7 +2278,7 @@ class DatabasePool:
         return row
 
     async def simple_delete_one(
-        self, table: str, keyvalues: Dict[str, Any], desc: str = "simple_delete_one"
+        self, table: str, keyvalues: dict[str, Any], desc: str = "simple_delete_one"
     ) -> None:
         """Executes a DELETE query on the named table, expecting to delete a
         single row.
@@ -2319,7 +2298,7 @@ class DatabasePool:
 
     @staticmethod
     def simple_delete_one_txn(
-        txn: LoggingTransaction, table: str, keyvalues: Dict[str, Any]
+        txn: LoggingTransaction, table: str, keyvalues: dict[str, Any]
     ) -> None:
         """Executes a DELETE query on the named table, expecting to delete a
         single row.
@@ -2340,7 +2319,7 @@ class DatabasePool:
             raise StoreError(500, "More than one row matched (%s)" % (table,))
 
     async def simple_delete(
-        self, table: str, keyvalues: Dict[str, Any], desc: str
+        self, table: str, keyvalues: dict[str, Any], desc: str
     ) -> int:
         """Executes a DELETE query on the named table.
 
@@ -2360,7 +2339,7 @@ class DatabasePool:
 
     @staticmethod
     def simple_delete_txn(
-        txn: LoggingTransaction, table: str, keyvalues: Dict[str, Any]
+        txn: LoggingTransaction, table: str, keyvalues: dict[str, Any]
     ) -> int:
         """Executes a DELETE query on the named table.
 
@@ -2386,7 +2365,7 @@ class DatabasePool:
         table: str,
         column: str,
         iterable: Collection[Any],
-        keyvalues: Dict[str, Any],
+        keyvalues: dict[str, Any],
         desc: str,
     ) -> int:
         """Executes a DELETE query on the named table.
@@ -2420,7 +2399,7 @@ class DatabasePool:
         table: str,
         column: str,
         values: Collection[Any],
-        keyvalues: Dict[str, Any],
+        keyvalues: dict[str, Any],
     ) -> int:
         """Executes a DELETE query on the named table.
 
@@ -2500,7 +2479,7 @@ class DatabasePool:
         stream_column: str,
         max_value: int,
         limit: int = 100000,
-    ) -> Tuple[Dict[Any, int], int]:
+    ) -> tuple[dict[Any, int], int]:
         """Gets roughly the last N changes in the given stream table as a
         map from entity to the stream ID of the most recent change.
 
@@ -2525,7 +2504,7 @@ class DatabasePool:
 
         # The rows come out in reverse stream ID order, so we want to keep the
         # stream ID of the first row for each entity.
-        cache: Dict[Any, int] = {}
+        cache: dict[Any, int] = {}
         for row in txn:
             cache.setdefault(row[0], int(row[1]))
 
@@ -2549,11 +2528,11 @@ class DatabasePool:
         start: int,
         limit: int,
         retcols: Iterable[str],
-        filters: Optional[Dict[str, Any]] = None,
-        keyvalues: Optional[Dict[str, Any]] = None,
-        exclude_keyvalues: Optional[Dict[str, Any]] = None,
+        filters: dict[str, Any] | None = None,
+        keyvalues: dict[str, Any] | None = None,
+        exclude_keyvalues: dict[str, Any] | None = None,
         order_direction: str = "ASC",
-    ) -> List[Tuple[Any, ...]]:
+    ) -> list[tuple[Any, ...]]:
         """
         Executes a SELECT query on the named table with start and limit,
         of row numbers, which may return zero or number of rows from start to limit,
@@ -2588,7 +2567,7 @@ class DatabasePool:
             raise ValueError("order_direction must be one of 'ASC' or 'DESC'.")
 
         where_clause = "WHERE " if filters or keyvalues or exclude_keyvalues else ""
-        arg_list: List[Any] = []
+        arg_list: list[Any] = []
         if filters:
             where_clause += " AND ".join("%s LIKE ?" % (k,) for k in filters)
             arg_list += list(filters.values())
@@ -2618,7 +2597,7 @@ def make_in_list_sql_clause(
     iterable: Collection[Any],
     *,
     negative: bool = False,
-) -> Tuple[str, list]:
+) -> tuple[str, list]:
     """Returns an SQL clause that checks the given column is in the iterable.
 
     On SQLite this expands to `column IN (?, ?, ...)`, whereas on Postgres
@@ -2658,24 +2637,24 @@ def make_in_list_sql_clause(
 @overload
 def make_tuple_in_list_sql_clause(
     database_engine: BaseDatabaseEngine,
-    columns: Tuple[str, str],
-    iterable: Collection[Tuple[Any, Any]],
-) -> Tuple[str, list]: ...
+    columns: tuple[str, str],
+    iterable: Collection[tuple[Any, Any]],
+) -> tuple[str, list]: ...
 
 
 @overload
 def make_tuple_in_list_sql_clause(
     database_engine: BaseDatabaseEngine,
-    columns: Tuple[str, str, str],
-    iterable: Collection[Tuple[Any, Any, Any]],
-) -> Tuple[str, list]: ...
+    columns: tuple[str, str, str],
+    iterable: Collection[tuple[Any, Any, Any]],
+) -> tuple[str, list]: ...
 
 
 def make_tuple_in_list_sql_clause(
     database_engine: BaseDatabaseEngine,
-    columns: Tuple[str, ...],
-    iterable: Collection[Tuple[Any, ...]],
-) -> Tuple[str, list]:
+    columns: tuple[str, ...],
+    iterable: Collection[tuple[Any, ...]],
+) -> tuple[str, list]:
     """Returns an SQL clause that checks the given tuple of columns is in the iterable.
 
     Args:
@@ -2723,7 +2702,7 @@ def make_tuple_in_list_sql_clause(
 KV = TypeVar("KV")
 
 
-def make_tuple_comparison_clause(keys: List[Tuple[str, KV]]) -> Tuple[str, List[KV]]:
+def make_tuple_comparison_clause(keys: list[tuple[str, KV]]) -> tuple[str, list[KV]]:
     """Returns a tuple comparison SQL clause
 
     Builds a SQL clause that looks like "(a, b) > (?, ?)"
diff --git a/synapse/storage/databases/__init__.py b/synapse/storage/databases/__init__.py
index a4aba96686..b44b84b913 100644
--- a/synapse/storage/databases/__init__.py
+++ b/synapse/storage/databases/__init__.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Generic, List, Optional, Type, TypeVar
+from typing import TYPE_CHECKING, Generic, TypeVar
 
 from synapse.metrics import SERVER_NAME_LABEL, LaterGauge
 from synapse.storage._base import SQLBaseStore
@@ -61,21 +61,21 @@ class Databases(Generic[DataStoreT]):
         state_deletion
     """
 
-    databases: List[DatabasePool]
+    databases: list[DatabasePool]
     main: "DataStore"  # FIXME: https://github.com/matrix-org/synapse/issues/11165: actually an instance of `main_store_class`
     state: StateGroupDataStore
-    persist_events: Optional[PersistEventsStore]
+    persist_events: PersistEventsStore | None
     state_deletion: StateDeletionDataStore
 
-    def __init__(self, main_store_class: Type[DataStoreT], hs: "HomeServer"):
+    def __init__(self, main_store_class: type[DataStoreT], hs: "HomeServer"):
         # Note we pass in the main store class here as workers use a different main
         # store.
 
         self.databases = []
-        main: Optional[DataStoreT] = None
-        state: Optional[StateGroupDataStore] = None
-        state_deletion: Optional[StateDeletionDataStore] = None
-        persist_events: Optional[PersistEventsStore] = None
+        main: DataStoreT | None = None
+        state: StateGroupDataStore | None = None
+        state_deletion: StateDeletionDataStore | None = None
+        persist_events: PersistEventsStore | None = None
 
         server_name = hs.hostname
 
diff --git a/synapse/storage/databases/main/__init__.py b/synapse/storage/databases/main/__init__.py
index 83b480adaf..12593094f1 100644
--- a/synapse/storage/databases/main/__init__.py
+++ b/synapse/storage/databases/main/__init__.py
@@ -20,7 +20,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, List, Optional, Tuple, Union, cast
+from typing import TYPE_CHECKING, cast
 
 import attr
 
@@ -99,14 +99,14 @@ class UserPaginateResponse:
     """This is very similar to UserInfo, but not quite the same."""
 
     name: str
-    user_type: Optional[str]
+    user_type: str | None
     is_guest: bool
     admin: bool
     deactivated: bool
     shadow_banned: bool
-    displayname: Optional[str]
-    avatar_url: Optional[str]
-    creation_ts: Optional[int]
+    displayname: str | None
+    avatar_url: str | None
+    creation_ts: int | None
     approved: bool
     erased: bool
     last_seen_ts: int
@@ -180,17 +180,17 @@ class DataStore(
         self,
         start: int,
         limit: int,
-        user_id: Optional[str] = None,
-        name: Optional[str] = None,
+        user_id: str | None = None,
+        name: str | None = None,
         guests: bool = True,
-        deactivated: Optional[bool] = None,
-        admins: Optional[bool] = None,
+        deactivated: bool | None = None,
+        admins: bool | None = None,
         order_by: str = UserSortOrder.NAME.value,
         direction: Direction = Direction.FORWARDS,
         approved: bool = True,
-        not_user_types: Optional[List[str]] = None,
+        not_user_types: list[str] | None = None,
         locked: bool = False,
-    ) -> Tuple[List[UserPaginateResponse], int]:
+    ) -> tuple[list[UserPaginateResponse], int]:
         """Function to retrieve a paginated list of users from
         users list. This will return a json list of users and the
         total number of users matching the filter criteria.
@@ -216,7 +216,7 @@ class DataStore(
 
         def get_users_paginate_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[List[UserPaginateResponse], int]:
+        ) -> tuple[list[UserPaginateResponse], int]:
             filters = []
             args: list = []
 
@@ -311,7 +311,7 @@ class DataStore(
                 """
             sql = "SELECT COUNT(*) as total_users " + sql_base
             txn.execute(sql, args)
-            count = cast(Tuple[int], txn.fetchone())[0]
+            count = cast(tuple[int], txn.fetchone())[0]
 
             sql = f"""
                 SELECT name, user_type, is_guest, admin, deactivated, shadow_banned,
@@ -351,9 +351,7 @@ class DataStore(
 
     async def search_users(
         self, term: str
-    ) -> List[
-        Tuple[str, Optional[str], Union[int, bool], Union[int, bool], Optional[str]]
-    ]:
+    ) -> list[tuple[str, str | None, int | bool, int | bool, str | None]]:
         """Function to search users list for one or more users with
         the matched term.
 
@@ -366,9 +364,7 @@ class DataStore(
 
         def search_users(
             txn: LoggingTransaction,
-        ) -> List[
-            Tuple[str, Optional[str], Union[int, bool], Union[int, bool], Optional[str]]
-        ]:
+        ) -> list[tuple[str, str | None, int | bool, int | bool, str | None]]:
             search_term = "%%" + term + "%%"
 
             sql = """
@@ -379,13 +375,13 @@ class DataStore(
             txn.execute(sql, (search_term,))
 
             return cast(
-                List[
-                    Tuple[
+                list[
+                    tuple[
                         str,
-                        Optional[str],
-                        Union[int, bool],
-                        Union[int, bool],
-                        Optional[str],
+                        str | None,
+                        int | bool,
+                        int | bool,
+                        str | None,
                     ]
                 ],
                 txn.fetchall(),
diff --git a/synapse/storage/databases/main/account_data.py b/synapse/storage/databases/main/account_data.py
index 16876e5461..15728cf618 100644
--- a/synapse/storage/databases/main/account_data.py
+++ b/synapse/storage/databases/main/account_data.py
@@ -23,13 +23,8 @@ import logging
 from typing import (
     TYPE_CHECKING,
     Any,
-    Dict,
-    FrozenSet,
     Iterable,
-    List,
     Mapping,
-    Optional,
-    Tuple,
     cast,
 )
 
@@ -140,7 +135,7 @@ class AccountDataWorkerStore(PushRulesWorkerStore, CacheInvalidationWorkerStore)
 
         def get_global_account_data_for_user(
             txn: LoggingTransaction,
-        ) -> Dict[str, JsonDict]:
+        ) -> dict[str, JsonDict]:
             # The 'content != '{}' condition below prevents us from using
             # `simple_select_list_txn` here, as it doesn't support conditions
             # other than 'equals'.
@@ -185,7 +180,7 @@ class AccountDataWorkerStore(PushRulesWorkerStore, CacheInvalidationWorkerStore)
 
         def get_room_account_data_for_user_txn(
             txn: LoggingTransaction,
-        ) -> Dict[str, Dict[str, JsonMapping]]:
+        ) -> dict[str, dict[str, JsonMapping]]:
             # The 'content != '{}' condition below prevents us from using
             # `simple_select_list_txn` here, as it doesn't support conditions
             # other than 'equals'.
@@ -202,7 +197,7 @@ class AccountDataWorkerStore(PushRulesWorkerStore, CacheInvalidationWorkerStore)
 
             txn.execute(sql, (user_id,))
 
-            by_room: Dict[str, Dict[str, JsonMapping]] = {}
+            by_room: dict[str, dict[str, JsonMapping]] = {}
             for room_id, account_data_type, content in txn:
                 room_data = by_room.setdefault(room_id, {})
 
@@ -217,7 +212,7 @@ class AccountDataWorkerStore(PushRulesWorkerStore, CacheInvalidationWorkerStore)
     @cached(num_args=2, max_entries=5000, tree=True)
     async def get_global_account_data_by_type_for_user(
         self, user_id: str, data_type: str
-    ) -> Optional[JsonMapping]:
+    ) -> JsonMapping | None:
         """
         Returns:
             The account data.
@@ -237,7 +232,7 @@ class AccountDataWorkerStore(PushRulesWorkerStore, CacheInvalidationWorkerStore)
 
     async def get_latest_stream_id_for_global_account_data_by_type_for_user(
         self, user_id: str, data_type: str
-    ) -> Optional[int]:
+    ) -> int | None:
         """
         Returns:
             The stream ID of the account data,
@@ -246,7 +241,7 @@ class AccountDataWorkerStore(PushRulesWorkerStore, CacheInvalidationWorkerStore)
 
         def get_latest_stream_id_for_global_account_data_by_type_for_user_txn(
             txn: LoggingTransaction,
-        ) -> Optional[int]:
+        ) -> int | None:
             sql = """
                 SELECT stream_id FROM account_data
                 WHERE user_id = ? AND account_data_type = ?
@@ -281,9 +276,9 @@ class AccountDataWorkerStore(PushRulesWorkerStore, CacheInvalidationWorkerStore)
 
         def get_account_data_for_room_txn(
             txn: LoggingTransaction,
-        ) -> Dict[str, JsonMapping]:
+        ) -> dict[str, JsonMapping]:
             rows = cast(
-                List[Tuple[str, str]],
+                list[tuple[str, str]],
                 self.db_pool.simple_select_list_txn(
                     txn,
                     table="room_account_data",
@@ -304,7 +299,7 @@ class AccountDataWorkerStore(PushRulesWorkerStore, CacheInvalidationWorkerStore)
     @cached(num_args=3, max_entries=5000, tree=True)
     async def get_account_data_for_room_and_type(
         self, user_id: str, room_id: str, account_data_type: str
-    ) -> Optional[JsonMapping]:
+    ) -> JsonMapping | None:
         """Get the client account_data of given type for a user for a room.
 
         Args:
@@ -317,7 +312,7 @@ class AccountDataWorkerStore(PushRulesWorkerStore, CacheInvalidationWorkerStore)
 
         def get_account_data_for_room_and_type_txn(
             txn: LoggingTransaction,
-        ) -> Optional[JsonDict]:
+        ) -> JsonDict | None:
             content_json = self.db_pool.simple_select_one_onecol_txn(
                 txn,
                 table="room_account_data",
@@ -338,7 +333,7 @@ class AccountDataWorkerStore(PushRulesWorkerStore, CacheInvalidationWorkerStore)
 
     async def get_updated_global_account_data(
         self, last_id: int, current_id: int, limit: int
-    ) -> List[Tuple[int, str, str]]:
+    ) -> list[tuple[int, str, str]]:
         """Get the global account_data that has changed, for the account_data stream
 
         Args:
@@ -355,14 +350,14 @@ class AccountDataWorkerStore(PushRulesWorkerStore, CacheInvalidationWorkerStore)
 
         def get_updated_global_account_data_txn(
             txn: LoggingTransaction,
-        ) -> List[Tuple[int, str, str]]:
+        ) -> list[tuple[int, str, str]]:
             sql = (
                 "SELECT stream_id, user_id, account_data_type"
                 " FROM account_data WHERE ? < stream_id AND stream_id <= ?"
                 " ORDER BY stream_id ASC LIMIT ?"
             )
             txn.execute(sql, (last_id, current_id, limit))
-            return cast(List[Tuple[int, str, str]], txn.fetchall())
+            return cast(list[tuple[int, str, str]], txn.fetchall())
 
         return await self.db_pool.runInteraction(
             "get_updated_global_account_data", get_updated_global_account_data_txn
@@ -370,7 +365,7 @@ class AccountDataWorkerStore(PushRulesWorkerStore, CacheInvalidationWorkerStore)
 
     async def get_updated_room_account_data(
         self, last_id: int, current_id: int, limit: int
-    ) -> List[Tuple[int, str, str, str]]:
+    ) -> list[tuple[int, str, str, str]]:
         """Get the global account_data that has changed, for the account_data stream
 
         Args:
@@ -387,14 +382,14 @@ class AccountDataWorkerStore(PushRulesWorkerStore, CacheInvalidationWorkerStore)
 
         def get_updated_room_account_data_txn(
             txn: LoggingTransaction,
-        ) -> List[Tuple[int, str, str, str]]:
+        ) -> list[tuple[int, str, str, str]]:
             sql = (
                 "SELECT stream_id, user_id, room_id, account_data_type"
                 " FROM room_account_data WHERE ? < stream_id AND stream_id <= ?"
                 " ORDER BY stream_id ASC LIMIT ?"
             )
             txn.execute(sql, (last_id, current_id, limit))
-            return cast(List[Tuple[int, str, str, str]], txn.fetchall())
+            return cast(list[tuple[int, str, str, str]], txn.fetchall())
 
         return await self.db_pool.runInteraction(
             "get_updated_room_account_data", get_updated_room_account_data_txn
@@ -402,7 +397,7 @@ class AccountDataWorkerStore(PushRulesWorkerStore, CacheInvalidationWorkerStore)
 
     async def get_updated_global_account_data_for_user(
         self, user_id: str, stream_id: int
-    ) -> Dict[str, JsonMapping]:
+    ) -> dict[str, JsonMapping]:
         """Get all the global account_data that's changed for a user.
 
         Args:
@@ -415,7 +410,7 @@ class AccountDataWorkerStore(PushRulesWorkerStore, CacheInvalidationWorkerStore)
 
         def get_updated_global_account_data_for_user(
             txn: LoggingTransaction,
-        ) -> Dict[str, JsonMapping]:
+        ) -> dict[str, JsonMapping]:
             sql = """
                 SELECT account_data_type, content FROM account_data
                 WHERE user_id = ? AND stream_id > ?
@@ -437,7 +432,7 @@ class AccountDataWorkerStore(PushRulesWorkerStore, CacheInvalidationWorkerStore)
 
     async def get_updated_room_account_data_for_user(
         self, user_id: str, stream_id: int
-    ) -> Dict[str, Dict[str, JsonMapping]]:
+    ) -> dict[str, dict[str, JsonMapping]]:
         """Get all the room account_data that's changed for a user.
 
         Args:
@@ -450,14 +445,14 @@ class AccountDataWorkerStore(PushRulesWorkerStore, CacheInvalidationWorkerStore)
 
         def get_updated_room_account_data_for_user_txn(
             txn: LoggingTransaction,
-        ) -> Dict[str, Dict[str, JsonMapping]]:
+        ) -> dict[str, dict[str, JsonMapping]]:
             sql = """
                 SELECT room_id, account_data_type, content FROM room_account_data
                 WHERE user_id = ? AND stream_id > ?
             """
             txn.execute(sql, (user_id, stream_id))
 
-            account_data_by_room: Dict[str, Dict[str, JsonMapping]] = {}
+            account_data_by_room: dict[str, dict[str, JsonMapping]] = {}
             for row in txn:
                 room_account_data = account_data_by_room.setdefault(row[0], {})
                 room_account_data[row[1]] = db_to_json(row[2])
@@ -484,7 +479,7 @@ class AccountDataWorkerStore(PushRulesWorkerStore, CacheInvalidationWorkerStore)
         room_id: str,
         from_stream_id: int,
         to_stream_id: int,
-    ) -> Dict[str, JsonMapping]:
+    ) -> dict[str, JsonMapping]:
         """Get the room account_data that's changed for a user in a room.
 
         (> `from_stream_id` and <= `to_stream_id`)
@@ -501,14 +496,14 @@ class AccountDataWorkerStore(PushRulesWorkerStore, CacheInvalidationWorkerStore)
 
         def get_updated_room_account_data_for_user_for_room_txn(
             txn: LoggingTransaction,
-        ) -> Dict[str, JsonMapping]:
+        ) -> dict[str, JsonMapping]:
             sql = """
                 SELECT account_data_type, content FROM room_account_data
                 WHERE user_id = ? AND room_id = ? AND stream_id > ? AND stream_id <= ?
             """
             txn.execute(sql, (user_id, room_id, from_stream_id, to_stream_id))
 
-            room_account_data: Dict[str, JsonMapping] = {}
+            room_account_data: dict[str, JsonMapping] = {}
             for row in txn:
                 room_account_data[row[0]] = db_to_json(row[1])
 
@@ -526,7 +521,7 @@ class AccountDataWorkerStore(PushRulesWorkerStore, CacheInvalidationWorkerStore)
         )
 
     @cached(max_entries=5000, iterable=True)
-    async def ignored_by(self, user_id: str) -> FrozenSet[str]:
+    async def ignored_by(self, user_id: str) -> frozenset[str]:
         """
         Get users which ignore the given user.
 
@@ -546,7 +541,7 @@ class AccountDataWorkerStore(PushRulesWorkerStore, CacheInvalidationWorkerStore)
         )
 
     @cached(max_entries=5000, iterable=True)
-    async def ignored_users(self, user_id: str) -> FrozenSet[str]:
+    async def ignored_users(self, user_id: str) -> frozenset[str]:
         """
         Get users which the given user ignores.
 
diff --git a/synapse/storage/databases/main/appservice.py b/synapse/storage/databases/main/appservice.py
index 97dbbb1493..6c2bf90b37 100644
--- a/synapse/storage/databases/main/appservice.py
+++ b/synapse/storage/databases/main/appservice.py
@@ -20,7 +20,7 @@
 #
 import logging
 import re
-from typing import TYPE_CHECKING, List, Optional, Pattern, Sequence, Tuple, cast
+from typing import TYPE_CHECKING, Pattern, Sequence, cast
 
 from synapse.appservice import (
     ApplicationService,
@@ -52,8 +52,8 @@ logger = logging.getLogger(__name__)
 
 
 def _make_exclusive_regex(
-    services_cache: List[ApplicationService],
-) -> Optional[Pattern]:
+    services_cache: list[ApplicationService],
+) -> Pattern | None:
     # We precompile a regex constructed from all the regexes that the AS's
     # have registered for exclusive users.
     exclusive_user_regexes = [
@@ -63,7 +63,7 @@ def _make_exclusive_regex(
     ]
     if exclusive_user_regexes:
         exclusive_user_regex = "|".join("(" + r + ")" for r in exclusive_user_regexes)
-        exclusive_user_pattern: Optional[Pattern] = re.compile(exclusive_user_regex)
+        exclusive_user_pattern: Pattern | None = re.compile(exclusive_user_regex)
     else:
         # We handle this case specially otherwise the constructed regex
         # will always match
@@ -93,7 +93,7 @@ class ApplicationServiceWorkerStore(RoomMemberWorkerStore):
             txn.execute(
                 "SELECT COALESCE(max(txn_id), 0) FROM application_services_txns"
             )
-            return cast(Tuple[int], txn.fetchone())[0]
+            return cast(tuple[int], txn.fetchone())[0]
 
         self._as_txn_seq_gen = build_sequence_generator(
             db_conn,
@@ -106,7 +106,7 @@ class ApplicationServiceWorkerStore(RoomMemberWorkerStore):
 
         super().__init__(database, db_conn, hs)
 
-    def get_app_services(self) -> List[ApplicationService]:
+    def get_app_services(self) -> list[ApplicationService]:
         return self.services_cache
 
     def get_if_app_services_interested_in_user(self, user_id: str) -> bool:
@@ -116,7 +116,7 @@ class ApplicationServiceWorkerStore(RoomMemberWorkerStore):
         else:
             return False
 
-    def get_app_service_by_user_id(self, user_id: str) -> Optional[ApplicationService]:
+    def get_app_service_by_user_id(self, user_id: str) -> ApplicationService | None:
         """Retrieve an application service from their user ID.
 
         All application services have associated with them a particular user ID.
@@ -134,7 +134,7 @@ class ApplicationServiceWorkerStore(RoomMemberWorkerStore):
                 return service
         return None
 
-    def get_app_service_by_token(self, token: str) -> Optional[ApplicationService]:
+    def get_app_service_by_token(self, token: str) -> ApplicationService | None:
         """Get the application service with the given appservice token.
 
         Args:
@@ -147,7 +147,7 @@ class ApplicationServiceWorkerStore(RoomMemberWorkerStore):
                 return service
         return None
 
-    def get_app_service_by_id(self, as_id: str) -> Optional[ApplicationService]:
+    def get_app_service_by_id(self, as_id: str) -> ApplicationService | None:
         """Get the application service with the given appservice ID.
 
         Args:
@@ -199,7 +199,7 @@ class ApplicationServiceTransactionWorkerStore(
 ):
     async def get_appservices_by_state(
         self, state: ApplicationServiceState
-    ) -> List[ApplicationService]:
+    ) -> list[ApplicationService]:
         """Get a list of application services based on their state.
 
         Args:
@@ -208,7 +208,7 @@ class ApplicationServiceTransactionWorkerStore(
             A list of ApplicationServices, which may be empty.
         """
         results = cast(
-            List[Tuple[str]],
+            list[tuple[str]],
             await self.db_pool.simple_select_list(
                 table="application_services_state",
                 keyvalues={"state": state.value},
@@ -227,7 +227,7 @@ class ApplicationServiceTransactionWorkerStore(
 
     async def get_appservice_state(
         self, service: ApplicationService
-    ) -> Optional[ApplicationServiceState]:
+    ) -> ApplicationServiceState | None:
         """Get the application service state.
 
         Args:
@@ -273,8 +273,8 @@ class ApplicationServiceTransactionWorkerStore(
         self,
         service: ApplicationService,
         events: Sequence[EventBase],
-        ephemeral: List[JsonMapping],
-        to_device_messages: List[JsonMapping],
+        ephemeral: list[JsonMapping],
+        to_device_messages: list[JsonMapping],
         one_time_keys_count: TransactionOneTimeKeysCount,
         unused_fallback_keys: TransactionUnusedFallbackKeys,
         device_list_summary: DeviceListUpdates,
@@ -347,7 +347,7 @@ class ApplicationServiceTransactionWorkerStore(
 
     async def get_oldest_unsent_txn(
         self, service: ApplicationService
-    ) -> Optional[AppServiceTransaction]:
+    ) -> AppServiceTransaction | None:
         """Get the oldest transaction which has not been sent for this service.
 
         Args:
@@ -358,7 +358,7 @@ class ApplicationServiceTransactionWorkerStore(
 
         def _get_oldest_unsent_txn(
             txn: LoggingTransaction,
-        ) -> Optional[Tuple[int, str]]:
+        ) -> tuple[int, str] | None:
             # Monotonically increasing txn ids, so just select the smallest
             # one in the txns table (we delete them when they are sent)
             txn.execute(
@@ -366,7 +366,7 @@ class ApplicationServiceTransactionWorkerStore(
                 " ORDER BY txn_id ASC LIMIT 1",
                 (service.id,),
             )
-            return cast(Optional[Tuple[int, str]], txn.fetchone())
+            return cast(tuple[int, str] | None, txn.fetchone())
 
         entry = await self.db_pool.runInteraction(
             "get_oldest_unsent_appservice_txn", _get_oldest_unsent_txn
@@ -447,7 +447,7 @@ class ApplicationServiceTransactionWorkerStore(
         )
 
     async def set_appservice_stream_type_pos(
-        self, service: ApplicationService, stream_type: str, pos: Optional[int]
+        self, service: ApplicationService, stream_type: str, pos: int | None
     ) -> None:
         if stream_type not in ("read_receipt", "presence", "to_device", "device_list"):
             raise ValueError(
diff --git a/synapse/storage/databases/main/cache.py b/synapse/storage/databases/main/cache.py
index cad26fefa4..b7b9b42461 100644
--- a/synapse/storage/databases/main/cache.py
+++ b/synapse/storage/databases/main/cache.py
@@ -23,7 +23,7 @@
 import itertools
 import json
 import logging
-from typing import TYPE_CHECKING, Any, Collection, Iterable, List, Optional, Tuple
+from typing import TYPE_CHECKING, Any, Collection, Iterable
 
 from synapse.api.constants import EventTypes
 from synapse.config._base import Config
@@ -104,7 +104,7 @@ class CacheInvalidationWorkerStore(SQLBaseStore):
             psql_only=True,  # The table is only on postgres DBs.
         )
 
-        self._cache_id_gen: Optional[MultiWriterIdGenerator]
+        self._cache_id_gen: MultiWriterIdGenerator | None
         if isinstance(self.database_engine, PostgresEngine):
             # We set the `writers` to an empty list here as we don't care about
             # missing updates over restarts, as we'll not have anything in our
@@ -145,7 +145,7 @@ class CacheInvalidationWorkerStore(SQLBaseStore):
 
     async def get_all_updated_caches(
         self, instance_name: str, last_id: int, current_id: int, limit: int
-    ) -> Tuple[List[Tuple[int, tuple]], int, bool]:
+    ) -> tuple[list[tuple[int, tuple]], int, bool]:
         """Get updates for caches replication stream.
 
         Args:
@@ -172,7 +172,7 @@ class CacheInvalidationWorkerStore(SQLBaseStore):
 
         def get_all_updated_caches_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[List[Tuple[int, tuple]], int, bool]:
+        ) -> tuple[list[tuple[int, tuple]], int, bool]:
             # We purposefully don't bound by the current token, as we want to
             # send across cache invalidations as quickly as possible. Cache
             # invalidations are idempotent, so duplicates are fine.
@@ -381,9 +381,9 @@ class CacheInvalidationWorkerStore(SQLBaseStore):
         event_id: str,
         room_id: str,
         etype: str,
-        state_key: Optional[str],
-        redacts: Optional[str],
-        relates_to: Optional[str],
+        state_key: str | None,
+        redacts: str | None,
+        relates_to: str | None,
         backfilled: bool,
     ) -> None:
         # This is needed to avoid a circular import.
@@ -597,7 +597,7 @@ class CacheInvalidationWorkerStore(SQLBaseStore):
         self._invalidate_state_caches_all(room_id)
 
     async def invalidate_cache_and_stream(
-        self, cache_name: str, keys: Tuple[Any, ...]
+        self, cache_name: str, keys: tuple[Any, ...]
     ) -> None:
         """Invalidates the cache and adds it to the cache stream so other workers
         will know to invalidate their caches.
@@ -620,7 +620,7 @@ class CacheInvalidationWorkerStore(SQLBaseStore):
         self,
         txn: LoggingTransaction,
         cache_func: CachedFunction,
-        keys: Tuple[Any, ...],
+        keys: tuple[Any, ...],
     ) -> None:
         """Invalidates the cache and adds it to the cache stream so other workers
         will know to invalidate their caches.
@@ -636,7 +636,7 @@ class CacheInvalidationWorkerStore(SQLBaseStore):
         self,
         txn: LoggingTransaction,
         cache_func: CachedFunction,
-        key_tuples: Collection[Tuple[Any, ...]],
+        key_tuples: Collection[tuple[Any, ...]],
     ) -> None:
         """A bulk version of _invalidate_cache_and_stream.
 
@@ -699,7 +699,7 @@ class CacheInvalidationWorkerStore(SQLBaseStore):
             )
 
     async def send_invalidation_to_replication(
-        self, cache_name: str, keys: Optional[Collection[Any]]
+        self, cache_name: str, keys: Collection[Any] | None
     ) -> None:
         await self.db_pool.runInteraction(
             "send_invalidation_to_replication",
@@ -709,7 +709,7 @@ class CacheInvalidationWorkerStore(SQLBaseStore):
         )
 
     def _send_invalidation_to_replication(
-        self, txn: LoggingTransaction, cache_name: str, keys: Optional[Iterable[Any]]
+        self, txn: LoggingTransaction, cache_name: str, keys: Iterable[Any] | None
     ) -> None:
         """Notifies replication that given cache has been invalidated.
 
@@ -751,7 +751,7 @@ class CacheInvalidationWorkerStore(SQLBaseStore):
                     "instance_name": self._instance_name,
                     "cache_func": cache_name,
                     "keys": keys,
-                    "invalidation_ts": self._clock.time_msec(),
+                    "invalidation_ts": self.clock.time_msec(),
                 },
             )
 
@@ -759,7 +759,7 @@ class CacheInvalidationWorkerStore(SQLBaseStore):
         self,
         txn: LoggingTransaction,
         cache_name: str,
-        key_tuples: Collection[Tuple[Any, ...]],
+        key_tuples: Collection[tuple[Any, ...]],
     ) -> None:
         """Announce the invalidation of multiple (but not all) cache entries.
 
@@ -778,7 +778,7 @@ class CacheInvalidationWorkerStore(SQLBaseStore):
             assert self._cache_id_gen is not None
 
             stream_ids = self._cache_id_gen.get_next_mult_txn(txn, len(key_tuples))
-            ts = self._clock.time_msec()
+            ts = self.clock.time_msec()
             txn.call_after(self.hs.get_notifier().on_new_replication_data)
             self.db_pool.simple_insert_many_txn(
                 txn,
@@ -830,7 +830,8 @@ class CacheInvalidationWorkerStore(SQLBaseStore):
             next_interval = REGULAR_CLEANUP_INTERVAL_MS
 
         self.hs.get_clock().call_later(
-            next_interval / 1000, self._clean_up_cache_invalidation_wrapper
+            next_interval / 1000,
+            self._clean_up_cache_invalidation_wrapper,
         )
 
     async def _clean_up_batch_of_old_cache_invalidations(
diff --git a/synapse/storage/databases/main/censor_events.py b/synapse/storage/databases/main/censor_events.py
index 3f9f482add..5d667a5345 100644
--- a/synapse/storage/databases/main/censor_events.py
+++ b/synapse/storage/databases/main/censor_events.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING
 
 from synapse.events.utils import prune_event_dict
 from synapse.metrics.background_process_metrics import wrap_as_background_process
@@ -77,7 +77,7 @@ class CensorEventsStore(EventsWorkerStore, CacheInvalidationWorkerStore, SQLBase
             return
 
         before_ts = (
-            self._clock.time_msec() - self.hs.config.server.redaction_retention_period
+            self.clock.time_msec() - self.hs.config.server.redaction_retention_period
         )
 
         # We fetch all redactions that:
@@ -121,7 +121,7 @@ class CensorEventsStore(EventsWorkerStore, CacheInvalidationWorkerStore, SQLBase
                 and original_event.internal_metadata.is_redacted()
             ):
                 # Redaction was allowed
-                pruned_json: Optional[str] = json_encoder.encode(
+                pruned_json: str | None = json_encoder.encode(
                     prune_event_dict(
                         original_event.room_version, original_event.get_dict()
                     )
diff --git a/synapse/storage/databases/main/client_ips.py b/synapse/storage/databases/main/client_ips.py
index c7a330cc83..4948d0c286 100644
--- a/synapse/storage/databases/main/client_ips.py
+++ b/synapse/storage/databases/main/client_ips.py
@@ -22,13 +22,8 @@
 import logging
 from typing import (
     TYPE_CHECKING,
-    Dict,
-    List,
     Mapping,
-    Optional,
-    Tuple,
     TypedDict,
-    Union,
     cast,
 )
 
@@ -67,9 +62,9 @@ class DeviceLastConnectionInfo:
     user_id: str
     device_id: str
 
-    ip: Optional[str]
-    user_agent: Optional[str]
-    last_seen: Optional[int]
+    ip: str | None
+    user_agent: str | None
+    last_seen: int | None
 
 
 class LastConnectionInfo(TypedDict):
@@ -179,7 +174,7 @@ class ClientIpBackgroundUpdateStore(SQLBaseStore):
         # Fetch the start of the batch
         begin_last_seen: int = progress.get("last_seen", 0)
 
-        def get_last_seen(txn: LoggingTransaction) -> Optional[int]:
+        def get_last_seen(txn: LoggingTransaction) -> int | None:
             txn.execute(
                 """
                 SELECT last_seen FROM user_ips
@@ -190,7 +185,7 @@ class ClientIpBackgroundUpdateStore(SQLBaseStore):
                 """,
                 (begin_last_seen, batch_size),
             )
-            row = cast(Optional[Tuple[int]], txn.fetchone())
+            row = cast(tuple[int] | None, txn.fetchone())
             if row:
                 return row[0]
             else:
@@ -222,7 +217,7 @@ class ClientIpBackgroundUpdateStore(SQLBaseStore):
 
             # Define the search space, which requires handling the last batch in
             # a different way
-            args: Tuple[int, ...]
+            args: tuple[int, ...]
             if last:
                 clause = "? <= last_seen"
                 args = (begin_last_seen,)
@@ -251,7 +246,7 @@ class ClientIpBackgroundUpdateStore(SQLBaseStore):
                 args,
             )
             res = cast(
-                List[Tuple[str, str, str, Optional[str], str, int, int]], txn.fetchall()
+                list[tuple[str, str, str, str | None, str, int, int]], txn.fetchall()
             )
 
             # We've got some duplicates
@@ -361,7 +356,7 @@ class ClientIpBackgroundUpdateStore(SQLBaseStore):
             #      we'll just end up updating the same device row multiple
             #      times, which is fine.
 
-            where_args: List[Union[str, int]]
+            where_args: list[str | int]
             where_clause, where_args = make_tuple_comparison_clause(
                 [("user_id", last_user_id), ("device_id", last_device_id)],
             )
@@ -383,7 +378,7 @@ class ClientIpBackgroundUpdateStore(SQLBaseStore):
             """ % {"where_clause": where_clause}
             txn.execute(sql, where_args + [batch_size])
 
-            rows = cast(List[Tuple[int, str, str, str, str]], txn.fetchall())
+            rows = cast(list[tuple[int, str, str, str, str]], txn.fetchall())
             if not rows:
                 return 0
 
@@ -434,29 +429,30 @@ class ClientIpWorkerStore(ClientIpBackgroundUpdateStore, MonthlyActiveUsersWorke
         self.user_ips_max_age = hs.config.server.user_ips_max_age
 
         # (user_id, access_token, ip,) -> last_seen
-        self.client_ip_last_seen = LruCache[Tuple[str, str, str], int](
+        self.client_ip_last_seen = LruCache[tuple[str, str, str], int](
             cache_name="client_ip_last_seen",
             server_name=self.server_name,
             max_size=50000,
+            clock=hs.get_clock(),
         )
 
         if hs.config.worker.run_background_tasks and self.user_ips_max_age:
-            self._clock.looping_call(self._prune_old_user_ips, 5 * 1000)
+            self.clock.looping_call(self._prune_old_user_ips, 5 * 1000)
 
         if self._update_on_this_worker:
             # This is the designated worker that can write to the client IP
             # tables.
 
             # (user_id, access_token, ip,) -> (user_agent, device_id, last_seen)
-            self._batch_row_update: Dict[
-                Tuple[str, str, str], Tuple[str, Optional[str], int]
+            self._batch_row_update: dict[
+                tuple[str, str, str], tuple[str, str | None, int]
             ] = {}
 
-            self._client_ip_looper = self._clock.looping_call(
-                self._update_client_ips_batch, 5 * 1000
-            )
-            self.hs.get_clock().add_system_event_trigger(
-                "before", "shutdown", self._update_client_ips_batch
+            self.clock.looping_call(self._update_client_ips_batch, 5 * 1000)
+            hs.register_async_shutdown_handler(
+                phase="before",
+                eventType="shutdown",
+                shutdown_func=self._update_client_ips_batch,
             )
 
     @wrap_as_background_process("prune_old_user_ips")
@@ -492,7 +488,7 @@ class ClientIpWorkerStore(ClientIpBackgroundUpdateStore, MonthlyActiveUsersWorke
             )
         """
 
-        timestamp = self._clock.time_msec() - self.user_ips_max_age
+        timestamp = self.clock.time_msec() - self.user_ips_max_age
 
         def _prune_old_user_ips_txn(txn: LoggingTransaction) -> None:
             txn.execute(sql, (timestamp,))
@@ -502,8 +498,8 @@ class ClientIpWorkerStore(ClientIpBackgroundUpdateStore, MonthlyActiveUsersWorke
         )
 
     async def _get_last_client_ip_by_device_from_database(
-        self, user_id: str, device_id: Optional[str]
-    ) -> Dict[Tuple[str, str], DeviceLastConnectionInfo]:
+        self, user_id: str, device_id: str | None
+    ) -> dict[tuple[str, str], DeviceLastConnectionInfo]:
         """For each device_id listed, give the user_ip it was last seen on.
 
         The result might be slightly out of date as client IPs are inserted in batches.
@@ -521,7 +517,7 @@ class ClientIpWorkerStore(ClientIpBackgroundUpdateStore, MonthlyActiveUsersWorke
             keyvalues["device_id"] = device_id
 
         res = cast(
-            List[Tuple[str, Optional[str], Optional[str], str, Optional[int]]],
+            list[tuple[str, str | None, str | None, str, int | None]],
             await self.db_pool.simple_select_list(
                 table="devices",
                 keyvalues=keyvalues,
@@ -542,7 +538,7 @@ class ClientIpWorkerStore(ClientIpBackgroundUpdateStore, MonthlyActiveUsersWorke
 
     async def _get_user_ip_and_agents_from_database(
         self, user: UserID, since_ts: int = 0
-    ) -> List[LastConnectionInfo]:
+    ) -> list[LastConnectionInfo]:
         """Fetch the IPs and user agents for a user since the given timestamp.
 
         The result might be slightly out of date as client IPs are inserted in batches.
@@ -566,7 +562,7 @@ class ClientIpWorkerStore(ClientIpBackgroundUpdateStore, MonthlyActiveUsersWorke
         """
         user_id = user.to_string()
 
-        def get_recent(txn: LoggingTransaction) -> List[Tuple[str, str, str, int]]:
+        def get_recent(txn: LoggingTransaction) -> list[tuple[str, str, str, int]]:
             txn.execute(
                 """
                 SELECT access_token, ip, user_agent, last_seen FROM user_ips
@@ -576,7 +572,7 @@ class ClientIpWorkerStore(ClientIpBackgroundUpdateStore, MonthlyActiveUsersWorke
                 """,
                 (since_ts, user_id),
             )
-            return cast(List[Tuple[str, str, str, int]], txn.fetchall())
+            return cast(list[tuple[str, str, str, int]], txn.fetchall())
 
         rows = await self.db_pool.runInteraction(
             desc="get_user_ip_and_agents", func=get_recent
@@ -598,8 +594,8 @@ class ClientIpWorkerStore(ClientIpBackgroundUpdateStore, MonthlyActiveUsersWorke
         access_token: str,
         ip: str,
         user_agent: str,
-        device_id: Optional[str],
-        now: Optional[int] = None,
+        device_id: str | None,
+        now: int | None = None,
     ) -> None:
         """Record that `user_id` used `access_token` from this `ip` address.
 
@@ -628,7 +624,7 @@ class ClientIpWorkerStore(ClientIpBackgroundUpdateStore, MonthlyActiveUsersWorke
             return
 
         if not now:
-            now = int(self._clock.time_msec())
+            now = int(self.clock.time_msec())
         key = (user_id, access_token, ip)
 
         try:
@@ -672,7 +668,7 @@ class ClientIpWorkerStore(ClientIpBackgroundUpdateStore, MonthlyActiveUsersWorke
     def _update_client_ips_batch_txn(
         self,
         txn: LoggingTransaction,
-        to_update: Mapping[Tuple[str, str, str], Tuple[str, Optional[str], int]],
+        to_update: Mapping[tuple[str, str, str], tuple[str, str | None, int]],
     ) -> None:
         assert self._update_on_this_worker, (
             "This worker is not designated to update client IPs"
@@ -717,8 +713,8 @@ class ClientIpWorkerStore(ClientIpBackgroundUpdateStore, MonthlyActiveUsersWorke
             )
 
     async def get_last_client_ip_by_device(
-        self, user_id: str, device_id: Optional[str]
-    ) -> Dict[Tuple[str, str], DeviceLastConnectionInfo]:
+        self, user_id: str, device_id: str | None
+    ) -> dict[tuple[str, str], DeviceLastConnectionInfo]:
         """For each device_id listed, give the user_ip it was last seen on
 
         Args:
@@ -758,7 +754,7 @@ class ClientIpWorkerStore(ClientIpBackgroundUpdateStore, MonthlyActiveUsersWorke
 
     async def get_user_ip_and_agents(
         self, user: UserID, since_ts: int = 0
-    ) -> List[LastConnectionInfo]:
+    ) -> list[LastConnectionInfo]:
         """Fetch the IPs and user agents for a user since the given timestamp.
 
         Args:
@@ -785,7 +781,7 @@ class ClientIpWorkerStore(ClientIpBackgroundUpdateStore, MonthlyActiveUsersWorke
             # the result
             return rows_from_db
 
-        results: Dict[Tuple[str, str], LastConnectionInfo] = {
+        results: dict[tuple[str, str], LastConnectionInfo] = {
             (connection["access_token"], connection["ip"]): connection
             for connection in rows_from_db
         }
@@ -807,7 +803,7 @@ class ClientIpWorkerStore(ClientIpBackgroundUpdateStore, MonthlyActiveUsersWorke
 
         return list(results.values())
 
-    async def get_last_seen_for_user_id(self, user_id: str) -> Optional[int]:
+    async def get_last_seen_for_user_id(self, user_id: str) -> int | None:
         """Get the last seen timestamp for a user, if we have it."""
 
         return await self.db_pool.simple_select_one_onecol(
diff --git a/synapse/storage/databases/main/delayed_events.py b/synapse/storage/databases/main/delayed_events.py
index 78f55b983f..b11ed86db2 100644
--- a/synapse/storage/databases/main/delayed_events.py
+++ b/synapse/storage/databases/main/delayed_events.py
@@ -13,7 +13,7 @@
 #
 
 import logging
-from typing import List, NewType, Optional, Tuple
+from typing import NewType
 
 import attr
 
@@ -42,10 +42,10 @@ Timestamp = NewType("Timestamp", int)
 class EventDetails:
     room_id: RoomID
     type: EventType
-    state_key: Optional[StateKey]
-    origin_server_ts: Optional[Timestamp]
+    state_key: StateKey | None
+    origin_server_ts: Timestamp | None
     content: JsonDict
-    device_id: Optional[DeviceID]
+    device_id: DeviceID | None
 
 
 @attr.s(slots=True, frozen=True, auto_attribs=True)
@@ -67,7 +67,7 @@ class DelayedEventsStore(SQLBaseStore):
             desc="get_delayed_events_stream_pos",
         )
 
-    async def update_delayed_events_stream_pos(self, stream_id: Optional[int]) -> None:
+    async def update_delayed_events_stream_pos(self, stream_id: int | None) -> None:
         """
         Updates the stream position of the background process to watch for state events
         that target the same piece of state as any pending delayed events.
@@ -85,15 +85,15 @@ class DelayedEventsStore(SQLBaseStore):
         self,
         *,
         user_localpart: str,
-        device_id: Optional[str],
+        device_id: str | None,
         creation_ts: Timestamp,
         room_id: str,
         event_type: str,
-        state_key: Optional[str],
-        origin_server_ts: Optional[int],
+        state_key: str | None,
+        origin_server_ts: int | None,
         content: JsonDict,
         delay: int,
-    ) -> Tuple[DelayID, Timestamp]:
+    ) -> tuple[DelayID, Timestamp]:
         """
         Inserts a new delayed event in the DB.
 
@@ -201,7 +201,7 @@ class DelayedEventsStore(SQLBaseStore):
     async def get_all_delayed_events_for_user(
         self,
         user_localpart: str,
-    ) -> List[JsonDict]:
+    ) -> list[JsonDict]:
         """Returns all pending delayed events owned by the given user."""
         # TODO: Support Pagination stream API ("next_batch" field)
         rows = await self.db_pool.execute(
@@ -236,9 +236,9 @@ class DelayedEventsStore(SQLBaseStore):
 
     async def process_timeout_delayed_events(
         self, current_ts: Timestamp
-    ) -> Tuple[
-        List[DelayedEventDetails],
-        Optional[Timestamp],
+    ) -> tuple[
+        list[DelayedEventDetails],
+        Timestamp | None,
     ]:
         """
         Marks for processing all delayed events that should have been sent prior to the provided time
@@ -250,9 +250,9 @@ class DelayedEventsStore(SQLBaseStore):
 
         def process_timeout_delayed_events_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[
-            List[DelayedEventDetails],
-            Optional[Timestamp],
+        ) -> tuple[
+            list[DelayedEventDetails],
+            Timestamp | None,
         ]:
             sql_cols = ", ".join(
                 (
@@ -322,9 +322,9 @@ class DelayedEventsStore(SQLBaseStore):
         *,
         delay_id: str,
         user_localpart: str,
-    ) -> Tuple[
+    ) -> tuple[
         EventDetails,
-        Optional[Timestamp],
+        Timestamp | None,
     ]:
         """
         Marks for processing the matching delayed event, regardless of its timeout time,
@@ -343,37 +343,32 @@ class DelayedEventsStore(SQLBaseStore):
 
         def process_target_delayed_event_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[
+        ) -> tuple[
             EventDetails,
-            Optional[Timestamp],
+            Timestamp | None,
         ]:
-            sql_cols = ", ".join(
-                (
-                    "room_id",
-                    "event_type",
-                    "state_key",
-                    "origin_server_ts",
-                    "content",
-                    "device_id",
-                )
-            )
-            sql_update = "UPDATE delayed_events SET is_processed = TRUE"
-            sql_where = "WHERE delay_id = ? AND user_localpart = ? AND NOT is_processed"
-            sql_args = (delay_id, user_localpart)
             txn.execute(
+                """
+                UPDATE delayed_events
+                SET is_processed = TRUE
+                WHERE delay_id = ? AND user_localpart = ?
+                    AND NOT is_processed
+                RETURNING
+                    room_id,
+                    event_type,
+                    state_key,
+                    origin_server_ts,
+                    content,
+                    device_id
+                """,
                 (
-                    f"{sql_update} {sql_where} RETURNING {sql_cols}"
-                    if self.database_engine.supports_returning
-                    else f"SELECT {sql_cols} FROM delayed_events {sql_where}"
+                    delay_id,
+                    user_localpart,
                 ),
-                sql_args,
             )
             row = txn.fetchone()
             if row is None:
                 raise NotFoundError("Delayed event not found")
-            elif not self.database_engine.supports_returning:
-                txn.execute(f"{sql_update} {sql_where}", sql_args)
-                assert txn.rowcount == 1
 
             event = EventDetails(
                 RoomID.from_string(row[0]),
@@ -395,7 +390,7 @@ class DelayedEventsStore(SQLBaseStore):
         *,
         delay_id: str,
         user_localpart: str,
-    ) -> Optional[Timestamp]:
+    ) -> Timestamp | None:
         """
         Cancels the matching delayed event, i.e. remove it as long as it hasn't been processed.
 
@@ -411,7 +406,7 @@ class DelayedEventsStore(SQLBaseStore):
 
         def cancel_delayed_event_txn(
             txn: LoggingTransaction,
-        ) -> Optional[Timestamp]:
+        ) -> Timestamp | None:
             try:
                 self.db_pool.simple_delete_one_txn(
                     txn,
@@ -441,7 +436,7 @@ class DelayedEventsStore(SQLBaseStore):
         event_type: str,
         state_key: str,
         not_from_localpart: str,
-    ) -> Optional[Timestamp]:
+    ) -> Timestamp | None:
         """
         Cancels all matching delayed state events, i.e. remove them as long as they haven't been processed.
 
@@ -457,7 +452,7 @@ class DelayedEventsStore(SQLBaseStore):
 
         def cancel_delayed_state_events_txn(
             txn: LoggingTransaction,
-        ) -> Optional[Timestamp]:
+        ) -> Timestamp | None:
             txn.execute(
                 """
                 DELETE FROM delayed_events
@@ -531,7 +526,7 @@ class DelayedEventsStore(SQLBaseStore):
             desc="unprocess_delayed_events",
         )
 
-    async def get_next_delayed_event_send_ts(self) -> Optional[Timestamp]:
+    async def get_next_delayed_event_send_ts(self) -> Timestamp | None:
         """
         Returns the send time of the next delayed event to be sent, if any.
         """
@@ -543,7 +538,7 @@ class DelayedEventsStore(SQLBaseStore):
 
     def _get_next_delayed_event_send_ts_txn(
         self, txn: LoggingTransaction
-    ) -> Optional[Timestamp]:
+    ) -> Timestamp | None:
         result = self.db_pool.simple_select_one_onecol_txn(
             txn,
             table="delayed_events",
diff --git a/synapse/storage/databases/main/deviceinbox.py b/synapse/storage/databases/main/deviceinbox.py
index f6f3c94a0d..a12411d723 100644
--- a/synapse/storage/databases/main/deviceinbox.py
+++ b/synapse/storage/databases/main/deviceinbox.py
@@ -24,12 +24,7 @@ import logging
 from typing import (
     TYPE_CHECKING,
     Collection,
-    Dict,
     Iterable,
-    List,
-    Optional,
-    Set,
-    Tuple,
     cast,
 )
 
@@ -91,14 +86,15 @@ class DeviceInboxWorkerStore(SQLBaseStore):
 
         # Map of (user_id, device_id) to the last stream_id that has been
         # deleted up to. This is so that we can no op deletions.
-        self._last_device_delete_cache: ExpiringCache[
-            Tuple[str, Optional[str]], int
-        ] = ExpiringCache(
-            cache_name="last_device_delete_cache",
-            server_name=self.server_name,
-            clock=self._clock,
-            max_len=10000,
-            expiry_ms=30 * 60 * 1000,
+        self._last_device_delete_cache: ExpiringCache[tuple[str, str | None], int] = (
+            ExpiringCache(
+                cache_name="last_device_delete_cache",
+                server_name=self.server_name,
+                hs=hs,
+                clock=self.clock,
+                max_len=10000,
+                expiry_ms=30 * 60 * 1000,
+            )
         )
 
         self._can_write_to_device = (
@@ -154,7 +150,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
         )
 
         if hs.config.worker.run_background_tasks:
-            self._clock.looping_call(
+            self.clock.looping_call(
                 run_as_background_process,
                 DEVICE_FEDERATION_INBOX_CLEANUP_INTERVAL_MS,
                 "_delete_old_federation_inbox_rows",
@@ -202,7 +198,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
         user_ids: Collection[str],
         from_stream_id: int,
         to_stream_id: int,
-    ) -> Dict[Tuple[str, str], List[JsonDict]]:
+    ) -> dict[tuple[str, str], list[JsonDict]]:
         """
         Retrieve to-device messages for a given set of users.
 
@@ -241,7 +237,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
         from_stream_id: int,
         to_stream_id: int,
         limit: int = 100,
-    ) -> Tuple[List[JsonDict], int]:
+    ) -> tuple[list[JsonDict], int]:
         """
         Retrieve to-device messages for a single user device.
 
@@ -270,7 +266,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
 
         def get_device_messages_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[List[JsonDict], int]:
+        ) -> tuple[list[JsonDict], int]:
             sql = """
                 SELECT stream_id, message_json FROM device_inbox
                 WHERE user_id = ? AND device_id = ?
@@ -283,7 +279,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
             # Create and fill a dictionary of (user ID, device ID) -> list of messages
             # intended for each device.
             last_processed_stream_pos = to_stream_id
-            to_device_messages: List[JsonDict] = []
+            to_device_messages: list[JsonDict] = []
             rowcount = 0
             for row in txn:
                 rowcount += 1
@@ -330,7 +326,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
         user_ids: Collection[str],
         from_stream_id: int,
         to_stream_id: int,
-    ) -> Tuple[Dict[Tuple[str, str], List[JsonDict]], int]:
+    ) -> tuple[dict[tuple[str, str], list[JsonDict]], int]:
         """
         Retrieve pending to-device messages for a collection of user devices.
 
@@ -362,7 +358,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
             logger.warning("No users provided upon querying for device IDs")
             return {}, to_stream_id
 
-        user_ids_to_query: Set[str] = set()
+        user_ids_to_query: set[str] = set()
 
         # Determine which users have devices with pending messages
         for user_id in user_ids:
@@ -377,7 +373,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
 
         def get_device_messages_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[Dict[Tuple[str, str], List[JsonDict]], int]:
+        ) -> tuple[dict[tuple[str, str], list[JsonDict]], int]:
             # Build a query to select messages from any of the given devices that
             # are between the given stream id bounds.
 
@@ -388,7 +384,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
             # since device_inbox has an index on `(user_id, device_id, stream_id)`
 
             user_device_dicts = cast(
-                List[Tuple[str]],
+                list[tuple[str]],
                 self.db_pool.simple_select_many_txn(
                     txn,
                     table="devices",
@@ -435,7 +431,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
 
             # Create and fill a dictionary of (user ID, device ID) -> list of messages
             # intended for each device.
-            recipient_device_to_messages: Dict[Tuple[str, str], List[JsonDict]] = {}
+            recipient_device_to_messages: dict[tuple[str, str], list[JsonDict]] = {}
             rowcount = 0
             for row in txn:
                 rowcount += 1
@@ -472,7 +468,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
     async def delete_messages_for_device(
         self,
         user_id: str,
-        device_id: Optional[str],
+        device_id: str | None,
         up_to_stream_id: int,
     ) -> int:
         """
@@ -530,11 +526,11 @@ class DeviceInboxWorkerStore(SQLBaseStore):
     async def delete_messages_for_device_between(
         self,
         user_id: str,
-        device_id: Optional[str],
-        from_stream_id: Optional[int],
+        device_id: str | None,
+        from_stream_id: int | None,
         to_stream_id: int,
         limit: int,
-    ) -> Tuple[Optional[int], int]:
+    ) -> tuple[int | None, int]:
         """Delete N device messages between the stream IDs, returning the
         highest stream ID deleted (or None if all messages in the range have
         been deleted) and the number of messages deleted.
@@ -554,7 +550,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
 
         def delete_messages_for_device_between_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[Optional[int], int]:
+        ) -> tuple[int | None, int]:
             txn.execute(
                 """
                 SELECT MAX(stream_id) FROM (
@@ -597,7 +593,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
     @trace
     async def get_new_device_msgs_for_remote(
         self, destination: str, last_stream_id: int, current_stream_id: int, limit: int
-    ) -> Tuple[List[JsonDict], int]:
+    ) -> tuple[list[JsonDict], int]:
         """
         Args:
             destination: The name of the remote server.
@@ -627,7 +623,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
         @trace
         def get_new_messages_for_remote_destination_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[List[JsonDict], int]:
+        ) -> tuple[list[JsonDict], int]:
             sql = (
                 "SELECT stream_id, messages_json FROM device_federation_outbox"
                 " WHERE destination = ?"
@@ -683,7 +679,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
 
     async def get_all_new_device_messages(
         self, instance_name: str, last_id: int, current_id: int, limit: int
-    ) -> Tuple[List[Tuple[int, tuple]], int, bool]:
+    ) -> tuple[list[tuple[int, tuple]], int, bool]:
         """Get updates for to device replication stream.
 
         Args:
@@ -710,7 +706,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
 
         def get_all_new_device_messages_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[List[Tuple[int, tuple]], int, bool]:
+        ) -> tuple[list[tuple[int, tuple]], int, bool]:
             # We limit like this as we might have multiple rows per stream_id, and
             # we want to make sure we always get all entries for any stream_id
             # we return.
@@ -745,8 +741,8 @@ class DeviceInboxWorkerStore(SQLBaseStore):
     @trace
     async def add_messages_to_device_inbox(
         self,
-        local_messages_by_user_then_device: Dict[str, Dict[str, JsonDict]],
-        remote_messages_by_destination: Dict[str, JsonDict],
+        local_messages_by_user_then_device: dict[str, dict[str, JsonDict]],
+        remote_messages_by_destination: dict[str, JsonDict],
     ) -> int:
         """Used to send messages from this server.
 
@@ -826,7 +822,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
                             )
 
         async with self._to_device_msg_id_gen.get_next() as stream_id:
-            now_ms = self._clock.time_msec()
+            now_ms = self.clock.time_msec()
             await self.db_pool.runInteraction(
                 "add_messages_to_device_inbox", add_messages_txn, now_ms, stream_id
             )
@@ -843,7 +839,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
         self,
         origin: str,
         message_id: str,
-        local_messages_by_user_then_device: Dict[str, Dict[str, JsonDict]],
+        local_messages_by_user_then_device: dict[str, dict[str, JsonDict]],
     ) -> int:
         assert self._can_write_to_device
 
@@ -881,7 +877,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
             )
 
         async with self._to_device_msg_id_gen.get_next() as stream_id:
-            now_ms = self._clock.time_msec()
+            now_ms = self.clock.time_msec()
             await self.db_pool.runInteraction(
                 "add_messages_from_remote_to_device_inbox",
                 add_messages_txn,
@@ -897,7 +893,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
         self,
         txn: LoggingTransaction,
         stream_id: int,
-        messages_by_user_then_device: Dict[str, Dict[str, JsonDict]],
+        messages_by_user_then_device: dict[str, dict[str, JsonDict]],
     ) -> None:
         assert self._can_write_to_device
 
@@ -928,7 +924,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
                 # We exclude hidden devices (such as cross-signing keys) here as they are
                 # not expected to receive to-device messages.
                 rows = cast(
-                    List[Tuple[str]],
+                    list[tuple[str]],
                     self.db_pool.simple_select_many_txn(
                         txn,
                         table="devices",
@@ -1002,7 +998,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
             # We delete at most 100 rows that are older than
             # DEVICE_FEDERATION_INBOX_CLEANUP_DELAY_MS
             delete_before_ts = (
-                self._clock.time_msec() - DEVICE_FEDERATION_INBOX_CLEANUP_DELAY_MS
+                self.clock.time_msec() - DEVICE_FEDERATION_INBOX_CLEANUP_DELAY_MS
             )
             sql = """
                 WITH to_delete AS (
@@ -1032,7 +1028,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
 
             # We sleep a bit so that we don't hammer the database in a tight
             # loop first time we run this.
-            await self._clock.sleep(1)
+            await self.clock.sleep(1)
 
     async def get_devices_with_messages(
         self, user_id: str, device_ids: StrCollection
@@ -1054,7 +1050,7 @@ class DeviceInboxWorkerStore(SQLBaseStore):
             txn.execute(sql, args)
             return {row[0] for row in txn}
 
-        results: Set[str] = set()
+        results: set[str] = set()
         for batch_device_ids in batch_iter(device_ids, 1000):
             batch_results = await self.db_pool.runInteraction(
                 "get_devices_with_messages",
@@ -1142,7 +1138,7 @@ class DeviceInboxBackgroundUpdateStore(SQLBaseStore):
 
         def _remove_dead_devices_from_device_inbox_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[int, bool]:
+        ) -> tuple[int, bool]:
             if "max_stream_id" in progress:
                 max_stream_id = progress["max_stream_id"]
             else:
@@ -1150,7 +1146,7 @@ class DeviceInboxBackgroundUpdateStore(SQLBaseStore):
                 # There's a type mismatch here between how we want to type the row and
                 # what fetchone says it returns, but we silence it because we know that
                 # res can't be None.
-                res = cast(Tuple[Optional[int]], txn.fetchone())
+                res = cast(tuple[int | None], txn.fetchone())
                 if res[0] is None:
                     # this can only happen if the `device_inbox` table is empty, in which
                     # case we have no work to do.
@@ -1213,7 +1209,7 @@ class DeviceInboxBackgroundUpdateStore(SQLBaseStore):
                 max_stream_id = progress["max_stream_id"]
             else:
                 txn.execute("SELECT max(stream_id) FROM device_federation_outbox")
-                res = cast(Tuple[Optional[int]], txn.fetchone())
+                res = cast(tuple[int | None], txn.fetchone())
                 if res[0] is None:
                     # this can only happen if the `device_inbox` table is empty, in which
                     # case we have no work to do.
diff --git a/synapse/storage/databases/main/devices.py b/synapse/storage/databases/main/devices.py
index fc1e1c73f1..caae2a0648 100644
--- a/synapse/storage/databases/main/devices.py
+++ b/synapse/storage/databases/main/devices.py
@@ -24,13 +24,8 @@ from typing import (
     TYPE_CHECKING,
     Any,
     Collection,
-    Dict,
     Iterable,
-    List,
     Mapping,
-    Optional,
-    Set,
-    Tuple,
     cast,
 )
 
@@ -195,7 +190,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
             )
 
         if hs.config.worker.run_background_tasks:
-            self._clock.looping_call(
+            self.clock.looping_call(
                 self._prune_old_outbound_device_pokes, 60 * 60 * 1000
             )
 
@@ -258,7 +253,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         return self._device_list_id_gen
 
     async def count_devices_by_users(
-        self, user_ids: Optional[Collection[str]] = None
+        self, user_ids: Collection[str] | None = None
     ) -> int:
         """Retrieve number of all devices of given users.
         Only returns number of devices that are not marked as hidden.
@@ -284,7 +279,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
             )
 
             txn.execute(sql + clause, args)
-            return cast(Tuple[int], txn.fetchone())[0]
+            return cast(tuple[int], txn.fetchone())[0]
 
         if not user_ids:
             return 0
@@ -297,9 +292,9 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         self,
         user_id: str,
         device_id: str,
-        initial_device_display_name: Optional[str],
-        auth_provider_id: Optional[str] = None,
-        auth_provider_session_id: Optional[str] = None,
+        initial_device_display_name: str | None,
+        auth_provider_id: str | None = None,
+        auth_provider_session_id: str | None = None,
     ) -> bool:
         """Ensure the given device is known; add it to the store if not
 
@@ -381,7 +376,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
             device_ids: The IDs of the devices to delete
         """
 
-        def _delete_devices_txn(txn: LoggingTransaction, device_ids: List[str]) -> None:
+        def _delete_devices_txn(txn: LoggingTransaction, device_ids: list[str]) -> None:
             self.db_pool.simple_delete_many_txn(
                 txn,
                 table="devices",
@@ -445,7 +440,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
             )
 
     async def update_device(
-        self, user_id: str, device_id: str, new_display_name: Optional[str] = None
+        self, user_id: str, device_id: str, new_display_name: str | None = None
     ) -> None:
         """Update a device. Only updates the device if it is not marked as
         hidden.
@@ -473,7 +468,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
     @cached(tree=True)
     async def get_device(
         self, user_id: str, device_id: str
-    ) -> Optional[Mapping[str, Any]]:
+    ) -> Mapping[str, Any] | None:
         """Retrieve a device. Only returns devices that are not marked as
         hidden.
 
@@ -497,7 +492,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
 
     async def get_devices_by_user(
         self, user_id: str
-    ) -> Dict[str, Dict[str, Optional[str]]]:
+    ) -> dict[str, dict[str, str | None]]:
         """Retrieve all of a user's registered devices. Only returns devices
         that are not marked as hidden.
 
@@ -508,7 +503,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
             and "display_name" for each device. Display name may be null.
         """
         devices = cast(
-            List[Tuple[str, str, Optional[str]]],
+            list[tuple[str, str, str | None]],
             await self.db_pool.simple_select_list(
                 table="devices",
                 keyvalues={"user_id": user_id, "hidden": False},
@@ -524,7 +519,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
 
     async def get_devices_by_auth_provider_session_id(
         self, auth_provider_id: str, auth_provider_session_id: str
-    ) -> List[Tuple[str, str]]:
+    ) -> list[tuple[str, str]]:
         """Retrieve the list of devices associated with a SSO IdP session ID.
 
         Args:
@@ -534,7 +529,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
             A list of dicts containing the device_id and the user_id of each device
         """
         return cast(
-            List[Tuple[str, str]],
+            list[tuple[str, str]],
             await self.db_pool.simple_select_list(
                 table="device_auth_providers",
                 keyvalues={
@@ -549,7 +544,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
     @trace
     async def get_device_updates_by_remote(
         self, destination: str, from_stream_id: int, limit: int
-    ) -> Tuple[int, List[Tuple[str, JsonDict]]]:
+    ) -> tuple[int, list[tuple[str, JsonDict]]]:
         """Get a stream of device updates to send to the given remote server.
 
         Args:
@@ -659,8 +654,8 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         last_processed_stream_id = from_stream_id
 
         # A map of (user ID, device ID) to (stream ID, context).
-        query_map: Dict[Tuple[str, str], Tuple[int, Optional[str]]] = {}
-        cross_signing_keys_by_user: Dict[str, Dict[str, object]] = {}
+        query_map: dict[tuple[str, str], tuple[int, str | None]] = {}
+        cross_signing_keys_by_user: dict[str, dict[str, object]] = {}
         for user_id, device_id, update_stream_id, update_context in updates:
             # Calculate the remaining length budget.
             # Note that, for now, each entry in `cross_signing_keys_by_user`
@@ -766,7 +761,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         from_stream_id: int,
         now_stream_id: int,
         limit: int,
-    ) -> List[Tuple[str, str, int, Optional[str]]]:
+    ) -> list[tuple[str, str, int, str | None]]:
         """Return device update information for a given remote destination
 
         Args:
@@ -792,14 +787,14 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         """
         txn.execute(sql, (destination, from_stream_id, now_stream_id, limit))
 
-        return cast(List[Tuple[str, str, int, Optional[str]]], txn.fetchall())
+        return cast(list[tuple[str, str, int, str | None]], txn.fetchall())
 
     async def _get_device_update_edus_by_remote(
         self,
         destination: str,
         from_stream_id: int,
-        query_map: Dict[Tuple[str, str], Tuple[int, Optional[str]]],
-    ) -> List[Tuple[str, dict]]:
+        query_map: dict[tuple[str, str], tuple[int, str | None]],
+    ) -> list[tuple[str, dict]]:
         """Returns a list of device update EDUs as well as E2EE keys
 
         Args:
@@ -933,7 +928,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         txn.execute(sql, (destination, stream_id))
 
     async def add_user_signature_change_to_streams(
-        self, from_user_id: str, user_ids: List[str]
+        self, from_user_id: str, user_ids: list[str]
     ) -> int:
         """Persist that a user has made new signatures
 
@@ -962,7 +957,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         self,
         txn: LoggingTransaction,
         from_user_id: str,
-        user_ids: List[str],
+        user_ids: list[str],
         stream_id: int,
     ) -> None:
         txn.call_after(
@@ -984,8 +979,8 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
     @trace
     @cancellable
     async def get_user_devices_from_cache(
-        self, user_ids: Set[str], user_and_device_ids: List[Tuple[str, str]]
-    ) -> Tuple[Set[str], Dict[str, Mapping[str, JsonMapping]]]:
+        self, user_ids: set[str], user_and_device_ids: list[tuple[str, str]]
+    ) -> tuple[set[str], dict[str, Mapping[str, JsonMapping]]]:
         """Get the devices (and keys if any) for remote users from the cache.
 
         Args:
@@ -1005,13 +1000,13 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         user_ids_not_in_cache = unique_user_ids - user_ids_in_cache
 
         # First fetch all the users which all devices are to be returned.
-        results: Dict[str, Mapping[str, JsonMapping]] = {}
+        results: dict[str, Mapping[str, JsonMapping]] = {}
         for user_id in user_ids:
             if user_id in user_ids_in_cache:
                 results[user_id] = await self.get_cached_devices_for_user(user_id)
         # Then fetch all device-specific requests, but skip users we've already
         # fetched all devices for.
-        device_specific_results: Dict[str, Dict[str, JsonMapping]] = {}
+        device_specific_results: dict[str, dict[str, JsonMapping]] = {}
         for user_id, device_id in user_and_device_ids:
             if user_id in user_ids_in_cache and user_id not in user_ids:
                 device = await self._get_cached_user_device(user_id, device_id)
@@ -1025,7 +1020,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
 
     async def get_users_whose_devices_are_cached(
         self, user_ids: StrCollection
-    ) -> Set[str]:
+    ) -> set[str]:
         """Checks which of the given users we have cached the devices for."""
         user_map = await self.get_device_list_last_stream_id_for_remotes(user_ids)
 
@@ -1056,7 +1051,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         self, user_id: str
     ) -> Mapping[str, JsonMapping]:
         devices = cast(
-            List[Tuple[str, str]],
+            list[tuple[str, str]],
             await self.db_pool.simple_select_list(
                 table="device_lists_remote_cache",
                 keyvalues={"user_id": user_id},
@@ -1071,7 +1066,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         self,
         from_key: MultiWriterStreamToken,
         to_key: MultiWriterStreamToken,
-    ) -> Set[str]:
+    ) -> set[str]:
         """Get all users whose devices have changed in the given range.
 
         Args:
@@ -1130,8 +1125,8 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         self,
         from_key: MultiWriterStreamToken,
         user_ids: Collection[str],
-        to_key: Optional[MultiWriterStreamToken] = None,
-    ) -> Set[str]:
+        to_key: MultiWriterStreamToken | None = None,
+    ) -> set[str]:
         """Get set of users whose devices have changed since `from_key` that
         are in the given list of user_ids.
 
@@ -1164,14 +1159,14 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
             txn: LoggingTransaction,
             from_key: MultiWriterStreamToken,
             to_key: MultiWriterStreamToken,
-        ) -> Set[str]:
+        ) -> set[str]:
             sql = """
                 SELECT user_id, stream_id, instance_name
                 FROM device_lists_stream
                 WHERE  ? < stream_id AND stream_id <= ? AND %s
             """
 
-            changes: Set[str] = set()
+            changes: set[str] = set()
 
             # Query device changes with a batch of users at a time
             for chunk in batch_iter(user_ids_to_check, 100):
@@ -1204,7 +1199,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
 
     async def get_users_whose_signatures_changed(
         self, user_id: str, from_key: MultiWriterStreamToken
-    ) -> Set[str]:
+    ) -> set[str]:
         """Get the users who have new cross-signing signatures made by `user_id` since
         `from_key`.
 
@@ -1243,7 +1238,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
 
     async def get_all_device_list_changes_for_remotes(
         self, instance_name: str, last_id: int, current_id: int, limit: int
-    ) -> Tuple[List[Tuple[int, tuple]], int, bool]:
+    ) -> tuple[list[tuple[int, tuple]], int, bool]:
         """Get updates for device lists replication stream.
 
         Args:
@@ -1270,7 +1265,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
 
         def _get_all_device_list_changes_for_remotes(
             txn: Cursor,
-        ) -> Tuple[List[Tuple[int, tuple]], int, bool]:
+        ) -> tuple[list[tuple[int, tuple]], int, bool]:
             # This query Does The Right Thing where it'll correctly apply the
             # bounds to the inner queries.
             sql = """
@@ -1302,7 +1297,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
     @cached(max_entries=10000)
     async def get_device_list_last_stream_id_for_remote(
         self, user_id: str
-    ) -> Optional[str]:
+    ) -> str | None:
         """Get the last stream_id we got for a user. May be None if we haven't
         got any information for them.
         """
@@ -1320,9 +1315,9 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
     )
     async def get_device_list_last_stream_id_for_remotes(
         self, user_ids: Iterable[str]
-    ) -> Mapping[str, Optional[str]]:
+    ) -> Mapping[str, str | None]:
         rows = cast(
-            List[Tuple[str, str]],
+            list[tuple[str, str]],
             await self.db_pool.simple_select_many_batch(
                 table="device_lists_remote_extremeties",
                 column="user_id",
@@ -1332,15 +1327,15 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
             ),
         )
 
-        results: Dict[str, Optional[str]] = dict.fromkeys(user_ids)
+        results: dict[str, str | None] = dict.fromkeys(user_ids)
         results.update(rows)
 
         return results
 
     async def get_user_ids_requiring_device_list_resync(
         self,
-        user_ids: Optional[Collection[str]] = None,
-    ) -> Set[str]:
+        user_ids: Collection[str] | None = None,
+    ) -> set[str]:
         """Given a list of remote users return the list of users that we
         should resync the device lists for. If None is given instead of a list,
         return every user that we should resync the device lists for.
@@ -1350,7 +1345,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         """
         if user_ids:
             rows = cast(
-                List[Tuple[str]],
+                list[tuple[str]],
                 await self.db_pool.simple_select_many_batch(
                     table="device_lists_remote_resync",
                     column="user_id",
@@ -1361,7 +1356,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
             )
         else:
             rows = cast(
-                List[Tuple[str]],
+                list[tuple[str]],
                 await self.db_pool.simple_select_list(
                     table="device_lists_remote_resync",
                     keyvalues=None,
@@ -1390,7 +1385,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
                     table="device_lists_remote_resync",
                     keyvalues={"user_id": user_id},
                     values={},
-                    insertion_values={"added_ts": self._clock.time_msec()},
+                    insertion_values={"added_ts": self.clock.time_msec()},
                 )
 
         await self.db_pool.runInteraction(
@@ -1406,7 +1401,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
             desc="mark_remote_user_device_cache_as_valid",
         )
 
-    async def handle_potentially_left_users(self, user_ids: Set[str]) -> None:
+    async def handle_potentially_left_users(self, user_ids: set[str]) -> None:
         """Given a set of remote users check if the server still shares a room with
         them. If not then mark those users' device cache as stale.
         """
@@ -1423,7 +1418,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
     def handle_potentially_left_users_txn(
         self,
         txn: LoggingTransaction,
-        user_ids: Set[str],
+        user_ids: set[str],
     ) -> None:
         """Given a set of remote users check if the server still shares a room with
         them. If not then mark those users' device cache as stale.
@@ -1461,9 +1456,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
             txn, self.get_device_list_last_stream_id_for_remote, (user_id,)
         )
 
-    async def get_dehydrated_device(
-        self, user_id: str
-    ) -> Optional[Tuple[str, JsonDict]]:
+    async def get_dehydrated_device(self, user_id: str) -> tuple[str, JsonDict] | None:
         """Retrieve the information for a dehydrated device.
 
         Args:
@@ -1488,8 +1481,8 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         device_id: str,
         device_data: str,
         time: int,
-        keys: Optional[JsonDict] = None,
-    ) -> Optional[str]:
+        keys: JsonDict | None = None,
+    ) -> str | None:
         # TODO: make keys non-optional once support for msc2697 is dropped
         if keys:
             device_keys = keys.get("device_keys", None)
@@ -1538,8 +1531,8 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         device_id: str,
         device_data: JsonDict,
         time_now: int,
-        keys: Optional[dict] = None,
-    ) -> Optional[str]:
+        keys: dict | None = None,
+    ) -> str | None:
         """Store a dehydrated device for a user.
 
         Args:
@@ -1601,7 +1594,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         that user when the destination comes back. It doesn't matter which device
         we keep.
         """
-        yesterday = self._clock.time_msec() - prune_age
+        yesterday = self.clock.time_msec() - prune_age
 
         def _prune_txn(txn: LoggingTransaction) -> None:
             # look for (user, destination) pairs which have an update older than
@@ -1672,7 +1665,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
 
     async def get_local_devices_not_accessed_since(
         self, since_ms: int
-    ) -> Dict[str, List[str]]:
+    ) -> dict[str, list[str]]:
         """Retrieves local devices that haven't been accessed since a given date.
 
         Args:
@@ -1687,20 +1680,20 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
 
         def get_devices_not_accessed_since_txn(
             txn: LoggingTransaction,
-        ) -> List[Tuple[str, str]]:
+        ) -> list[tuple[str, str]]:
             sql = """
                 SELECT user_id, device_id
                 FROM devices WHERE last_seen < ? AND hidden = FALSE
             """
             txn.execute(sql, (since_ms,))
-            return cast(List[Tuple[str, str]], txn.fetchall())
+            return cast(list[tuple[str, str]], txn.fetchall())
 
         rows = await self.db_pool.runInteraction(
             "get_devices_not_accessed_since",
             get_devices_not_accessed_since_txn,
         )
 
-        devices: Dict[str, List[str]] = {}
+        devices: dict[str, list[str]] = {}
         for user_id, device_id in rows:
             # Remote devices are never stale from our point of view.
             if self.hs.is_mine_id(user_id):
@@ -1728,7 +1721,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         room_ids: Collection[str],
         from_token: MultiWriterStreamToken,
         to_token: MultiWriterStreamToken,
-    ) -> Optional[Set[str]]:
+    ) -> set[str] | None:
         """Return the set of users whose devices have changed in the given rooms
         since the given stream ID.
 
@@ -1759,7 +1752,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         def _get_device_list_changes_in_rooms_txn(
             txn: LoggingTransaction,
             chunk: list[str],
-        ) -> Set[str]:
+        ) -> set[str]:
             clause, args = make_in_list_sql_clause(
                 self.database_engine, "room_id", chunk
             )
@@ -1788,7 +1781,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
 
         return changes
 
-    async def get_all_device_list_changes(self, from_id: int, to_id: int) -> Set[str]:
+    async def get_all_device_list_changes(self, from_id: int, to_id: int) -> set[str]:
         """Return the set of rooms where devices have changed since the given
         stream ID.
 
@@ -1807,7 +1800,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
 
         def _get_all_device_list_changes_txn(
             txn: LoggingTransaction,
-        ) -> Set[str]:
+        ) -> set[str]:
             txn.execute(sql, (from_id, to_id))
             return {room_id for (room_id,) in txn}
 
@@ -1818,7 +1811,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
 
     async def get_device_list_changes_in_room(
         self, room_id: str, min_stream_id: int
-    ) -> Collection[Tuple[str, str]]:
+    ) -> Collection[tuple[str, str]]:
         """Get all device list changes that happened in the room since the given
         stream ID.
 
@@ -1834,9 +1827,9 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
 
         def get_device_list_changes_in_room_txn(
             txn: LoggingTransaction,
-        ) -> Collection[Tuple[str, str]]:
+        ) -> Collection[tuple[str, str]]:
             txn.execute(sql, (room_id, min_stream_id))
-            return cast(Collection[Tuple[str, str]], txn.fetchall())
+            return cast(Collection[tuple[str, str]], txn.fetchall())
 
         return await self.db_pool.runInteraction(
             "get_device_list_changes_in_room",
@@ -1911,7 +1904,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         )
 
     async def update_remote_device_list_cache(
-        self, user_id: str, devices: List[dict], stream_id: int
+        self, user_id: str, devices: list[dict], stream_id: int
     ) -> None:
         """Replace the entire cache of the remote user's devices.
 
@@ -1932,7 +1925,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         )
 
     def _update_remote_device_list_cache_txn(
-        self, txn: LoggingTransaction, user_id: str, devices: List[dict], stream_id: int
+        self, txn: LoggingTransaction, user_id: str, devices: list[dict], stream_id: int
     ) -> None:
         """Replace the list of cached devices for this user with the given list."""
         self.db_pool.simple_delete_txn(
@@ -1967,7 +1960,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         user_id: str,
         device_ids: StrCollection,
         room_ids: StrCollection,
-    ) -> Optional[int]:
+    ) -> int | None:
         """Persist that a user's devices have been updated, and which hosts
         (if any) should be poked.
 
@@ -2016,7 +2009,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
 
             return stream_ids[-1]
 
-        last_stream_id: Optional[int] = None
+        last_stream_id: int | None = None
         for batch_device_ids in batch_iter(device_ids, 1000):
             last_stream_id = await self.db_pool.runInteraction(
                 "add_device_change_to_stream",
@@ -2031,7 +2024,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         txn: LoggingTransaction,
         user_id: str,
         device_ids: Collection[str],
-        stream_ids: List[int],
+        stream_ids: list[int],
     ) -> None:
         txn.call_after(
             self._device_list_stream_cache.entity_has_changed,
@@ -2076,7 +2069,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         device_id: str,
         hosts: Collection[str],
         stream_id: int,
-        context: Optional[Dict[str, str]],
+        context: dict[str, str] | None,
     ) -> None:
         if self._device_list_federation_stream_cache:
             for host in hosts:
@@ -2086,7 +2079,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
                     stream_id,
                 )
 
-        now = self._clock.time_msec()
+        now = self.clock.time_msec()
 
         encoded_context = json_encoder.encode(context)
         mark_sent = not self.hs.is_mine_id(user_id)
@@ -2163,8 +2156,8 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         user_id: str,
         device_ids: StrCollection,
         room_ids: StrCollection,
-        stream_ids: List[int],
-        context: Dict[str, str],
+        stream_ids: list[int],
+        context: dict[str, str],
     ) -> None:
         """Record the user in the room has updated their device."""
 
@@ -2208,7 +2201,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
 
     async def get_uncoverted_outbound_room_pokes(
         self, start_stream_id: int, start_room_id: str, limit: int = 10
-    ) -> List[Tuple[str, str, str, int, Optional[Dict[str, str]]]]:
+    ) -> list[tuple[str, str, str, int, dict[str, str] | None]]:
         """Get device list changes by room that have not yet been handled and
         written to `device_lists_outbound_pokes`.
 
@@ -2236,7 +2229,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
 
         def get_uncoverted_outbound_room_pokes_txn(
             txn: LoggingTransaction,
-        ) -> List[Tuple[str, str, str, int, Optional[Dict[str, str]]]]:
+        ) -> list[tuple[str, str, str, int, dict[str, str] | None]]:
             txn.execute(
                 sql,
                 (
@@ -2270,7 +2263,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
         device_id: str,
         room_id: str,
         hosts: Collection[str],
-        context: Optional[Dict[str, str]],
+        context: dict[str, str] | None,
     ) -> None:
         """Queue the device update to be sent to the given set of hosts,
         calculated from the room ID.
@@ -2327,7 +2320,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
 
     async def get_pending_remote_device_list_updates_for_room(
         self, room_id: str
-    ) -> Collection[Tuple[str, str]]:
+    ) -> Collection[tuple[str, str]]:
         """Get the set of remote device list updates from the pending table for
         the room.
         """
@@ -2361,16 +2354,16 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
 
         def get_pending_remote_device_list_updates_for_room_txn(
             txn: LoggingTransaction,
-        ) -> Collection[Tuple[str, str]]:
+        ) -> Collection[tuple[str, str]]:
             txn.execute(sql, (room_id, min_device_stream_id))
-            return cast(Collection[Tuple[str, str]], txn.fetchall())
+            return cast(Collection[tuple[str, str]], txn.fetchall())
 
         return await self.db_pool.runInteraction(
             "get_pending_remote_device_list_updates_for_room",
             get_pending_remote_device_list_updates_for_room_txn,
         )
 
-    async def get_device_change_last_converted_pos(self) -> Tuple[int, str]:
+    async def get_device_change_last_converted_pos(self) -> tuple[int, str]:
         """
         Get the position of the last row in `device_list_changes_in_room` that has been
         converted to `device_lists_outbound_pokes`.
@@ -2388,7 +2381,7 @@ class DeviceWorkerStore(RoomMemberWorkerStore, EndToEndKeyWorkerStore):
             retcols=["stream_id", "room_id"],
             desc="get_device_change_last_converted_pos",
         )
-        return cast(Tuple[int, str], min(rows))
+        return cast(tuple[int, str], min(rows))
 
     async def set_device_change_last_converted_pos(
         self,
diff --git a/synapse/storage/databases/main/directory.py b/synapse/storage/databases/main/directory.py
index 49c0575aca..5e14ad4480 100644
--- a/synapse/storage/databases/main/directory.py
+++ b/synapse/storage/databases/main/directory.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import Iterable, List, Optional, Sequence, Tuple
+from typing import Iterable, Sequence
 
 import attr
 
@@ -34,13 +34,13 @@ from synapse.util.caches.descriptors import cached
 class RoomAliasMapping:
     room_id: str
     room_alias: str
-    servers: List[str]
+    servers: list[str]
 
 
 class DirectoryWorkerStore(CacheInvalidationWorkerStore):
     async def get_association_from_room_alias(
         self, room_alias: RoomAlias
-    ) -> Optional[RoomAliasMapping]:
+    ) -> RoomAliasMapping | None:
         """Gets the room_id and server list for a given room_alias
 
         Args:
@@ -94,7 +94,7 @@ class DirectoryWorkerStore(CacheInvalidationWorkerStore):
         room_alias: RoomAlias,
         room_id: str,
         servers: Iterable[str],
-        creator: Optional[str] = None,
+        creator: str | None = None,
     ) -> None:
         """Creates an association between a room alias and room_id/servers
 
@@ -136,7 +136,7 @@ class DirectoryWorkerStore(CacheInvalidationWorkerStore):
                 409, "Room alias %s already exists" % room_alias.to_string()
             )
 
-    async def delete_room_alias(self, room_alias: RoomAlias) -> Optional[str]:
+    async def delete_room_alias(self, room_alias: RoomAlias) -> str | None:
         room_id = await self.db_pool.runInteraction(
             "delete_room_alias", self._delete_room_alias_txn, room_alias
         )
@@ -145,7 +145,7 @@ class DirectoryWorkerStore(CacheInvalidationWorkerStore):
 
     def _delete_room_alias_txn(
         self, txn: LoggingTransaction, room_alias: RoomAlias
-    ) -> Optional[str]:
+    ) -> str | None:
         txn.execute(
             "SELECT room_id FROM room_aliases WHERE room_alias = ?",
             (room_alias.to_string(),),
@@ -174,7 +174,7 @@ class DirectoryWorkerStore(CacheInvalidationWorkerStore):
         self,
         old_room_id: str,
         new_room_id: str,
-        creator: Optional[str] = None,
+        creator: str | None = None,
     ) -> None:
         """Repoint all of the aliases for a given room, to a different room.
 
@@ -187,7 +187,7 @@ class DirectoryWorkerStore(CacheInvalidationWorkerStore):
 
         def _update_aliases_for_room_txn(txn: LoggingTransaction) -> None:
             update_creator_sql = ""
-            sql_params: Tuple[str, ...] = (new_room_id, old_room_id)
+            sql_params: tuple[str, ...] = (new_room_id, old_room_id)
             if creator:
                 update_creator_sql = ", creator = ?"
                 sql_params = (new_room_id, creator, old_room_id)
diff --git a/synapse/storage/databases/main/e2e_room_keys.py b/synapse/storage/databases/main/e2e_room_keys.py
index d978e115e4..01e9fb4dcf 100644
--- a/synapse/storage/databases/main/e2e_room_keys.py
+++ b/synapse/storage/databases/main/e2e_room_keys.py
@@ -21,13 +21,9 @@
 
 from typing import (
     TYPE_CHECKING,
-    Dict,
     Iterable,
-    List,
     Literal,
     Mapping,
-    Optional,
-    Tuple,
     TypedDict,
     cast,
 )
@@ -195,7 +191,7 @@ class EndToEndRoomKeyStore(EndToEndRoomKeyBackgroundStore):
         )
 
     async def add_e2e_room_keys(
-        self, user_id: str, version: str, room_keys: Iterable[Tuple[str, str, RoomKey]]
+        self, user_id: str, version: str, room_keys: Iterable[tuple[str, str, RoomKey]]
     ) -> None:
         """Bulk add room keys to a given backup.
 
@@ -255,10 +251,10 @@ class EndToEndRoomKeyStore(EndToEndRoomKeyBackgroundStore):
         self,
         user_id: str,
         version: str,
-        room_id: Optional[str] = None,
-        session_id: Optional[str] = None,
-    ) -> Dict[
-        Literal["rooms"], Dict[str, Dict[Literal["sessions"], Dict[str, RoomKey]]]
+        room_id: str | None = None,
+        session_id: str | None = None,
+    ) -> dict[
+        Literal["rooms"], dict[str, dict[Literal["sessions"], dict[str, RoomKey]]]
     ]:
         """Bulk get the E2E room keys for a given backup, optionally filtered to a given
         room, or a given session.
@@ -290,7 +286,7 @@ class EndToEndRoomKeyStore(EndToEndRoomKeyBackgroundStore):
                 keyvalues["session_id"] = session_id
 
         rows = cast(
-            List[Tuple[str, str, int, int, int, str]],
+            list[tuple[str, str, int, int, int, str]],
             await self.db_pool.simple_select_list(
                 table="e2e_room_keys",
                 keyvalues=keyvalues,
@@ -306,8 +302,8 @@ class EndToEndRoomKeyStore(EndToEndRoomKeyBackgroundStore):
             ),
         )
 
-        sessions: Dict[
-            Literal["rooms"], Dict[str, Dict[Literal["sessions"], Dict[str, RoomKey]]]
+        sessions: dict[
+            Literal["rooms"], dict[str, dict[Literal["sessions"], dict[str, RoomKey]]]
         ] = {"rooms": {}}
         for (
             room_id,
@@ -333,7 +329,7 @@ class EndToEndRoomKeyStore(EndToEndRoomKeyBackgroundStore):
         user_id: str,
         version: str,
         room_keys: Mapping[str, Mapping[Literal["sessions"], Iterable[str]]],
-    ) -> Dict[str, Dict[str, RoomKey]]:
+    ) -> dict[str, dict[str, RoomKey]]:
         """Get multiple room keys at a time.  The difference between this function and
         get_e2e_room_keys is that this function can be used to retrieve
         multiple specific keys at a time, whereas get_e2e_room_keys is used for
@@ -370,7 +366,7 @@ class EndToEndRoomKeyStore(EndToEndRoomKeyBackgroundStore):
         user_id: str,
         version: int,
         room_keys: Mapping[str, Mapping[Literal["sessions"], Iterable[str]]],
-    ) -> Dict[str, Dict[str, RoomKey]]:
+    ) -> dict[str, dict[str, RoomKey]]:
         if not room_keys:
             return {}
 
@@ -400,7 +396,7 @@ class EndToEndRoomKeyStore(EndToEndRoomKeyBackgroundStore):
 
         txn.execute(sql, params)
 
-        ret: Dict[str, Dict[str, RoomKey]] = {}
+        ret: dict[str, dict[str, RoomKey]] = {}
 
         for row in txn:
             room_id = row[0]
@@ -441,8 +437,8 @@ class EndToEndRoomKeyStore(EndToEndRoomKeyBackgroundStore):
         self,
         user_id: str,
         version: str,
-        room_id: Optional[str] = None,
-        session_id: Optional[str] = None,
+        room_id: str | None = None,
+        session_id: str | None = None,
     ) -> None:
         """Bulk delete the E2E room keys for a given backup, optionally filtered to a given
         room or a given session.
@@ -483,13 +479,13 @@ class EndToEndRoomKeyStore(EndToEndRoomKeyBackgroundStore):
         )
         # `SELECT MAX() FROM ...` will always return 1 row. The value in that row will
         # be `NULL` when there are no available versions.
-        row = cast(Tuple[Optional[int]], txn.fetchone())
+        row = cast(tuple[int | None], txn.fetchone())
         if row[0] is None:
             raise StoreError(404, "No current backup version")
         return row[0]
 
     async def get_e2e_room_keys_version_info(
-        self, user_id: str, version: Optional[str] = None
+        self, user_id: str, version: str | None = None
     ) -> JsonDict:
         """Get info metadata about a version of our room_keys backup.
 
@@ -559,7 +555,7 @@ class EndToEndRoomKeyStore(EndToEndRoomKeyBackgroundStore):
                 "SELECT MAX(version) FROM e2e_room_keys_versions WHERE user_id=?",
                 (user_id,),
             )
-            current_version = cast(Tuple[Optional[int]], txn.fetchone())[0]
+            current_version = cast(tuple[int | None], txn.fetchone())[0]
             if current_version is None:
                 current_version = 0
 
@@ -587,8 +583,8 @@ class EndToEndRoomKeyStore(EndToEndRoomKeyBackgroundStore):
         self,
         user_id: str,
         version: str,
-        info: Optional[JsonDict] = None,
-        version_etag: Optional[int] = None,
+        info: JsonDict | None = None,
+        version_etag: int | None = None,
     ) -> None:
         """Update a given backup version
 
@@ -600,7 +596,7 @@ class EndToEndRoomKeyStore(EndToEndRoomKeyBackgroundStore):
             version_etag: etag of the keys in the backup. If None, then the etag
                 is not updated.
         """
-        updatevalues: Dict[str, object] = {}
+        updatevalues: dict[str, object] = {}
 
         if info is not None and "auth_data" in info:
             updatevalues["auth_data"] = json_encoder.encode(info["auth_data"])
@@ -624,7 +620,7 @@ class EndToEndRoomKeyStore(EndToEndRoomKeyBackgroundStore):
 
     @trace
     async def delete_e2e_room_keys_version(
-        self, user_id: str, version: Optional[str] = None
+        self, user_id: str, version: str | None = None
     ) -> None:
         """Delete a given backup version of the user's room keys.
         Doesn't delete their actual key data.
diff --git a/synapse/storage/databases/main/end_to_end_keys.py b/synapse/storage/databases/main/end_to_end_keys.py
index 2e9f62075a..c93ebd3dda 100644
--- a/synapse/storage/databases/main/end_to_end_keys.py
+++ b/synapse/storage/databases/main/end_to_end_keys.py
@@ -25,16 +25,10 @@ from typing import (
     TYPE_CHECKING,
     Any,
     Collection,
-    Dict,
     Iterable,
-    List,
     Literal,
     Mapping,
-    Optional,
     Sequence,
-    Set,
-    Tuple,
-    Union,
     cast,
     overload,
 )
@@ -75,12 +69,12 @@ if TYPE_CHECKING:
 class DeviceKeyLookupResult:
     """The type returned by get_e2e_device_keys_and_signatures"""
 
-    display_name: Optional[str]
+    display_name: str | None
 
     # the key data from e2e_device_keys_json. Typically includes fields like
     # "algorithm", "keys" (including the curve25519 identity key and the ed25519 signing
     # key) and "signatures" (a map from (user id) to (key id/device_id) to signature.)
-    keys: Optional[JsonDict]
+    keys: JsonDict | None
 
 
 class EndToEndKeyBackgroundStore(SQLBaseStore):
@@ -155,7 +149,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
 
     async def get_e2e_device_keys_for_federation_query(
         self, user_id: str
-    ) -> Tuple[int, Sequence[JsonMapping]]:
+    ) -> tuple[int, Sequence[JsonMapping]]:
         """Get all devices (with any device keys) for a user
 
         Returns:
@@ -241,9 +235,9 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
     @cancellable
     async def get_e2e_device_keys_for_cs_api(
         self,
-        query_list: Collection[Tuple[str, Optional[str]]],
+        query_list: Collection[tuple[str, str | None]],
         include_displaynames: bool = True,
-    ) -> Dict[str, Dict[str, JsonDict]]:
+    ) -> dict[str, dict[str, JsonDict]]:
         """Fetch a list of device keys, formatted suitably for the C/S API.
         Args:
             query_list: List of pairs of user_ids and device_ids.
@@ -262,7 +256,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
 
         # Build the result structure, un-jsonify the results, and add the
         # "unsigned" section
-        rv: Dict[str, Dict[str, JsonDict]] = {}
+        rv: dict[str, dict[str, JsonDict]] = {}
         for user_id, device_keys in results.items():
             rv[user_id] = {}
             for device_id, device_info in device_keys.items():
@@ -284,37 +278,37 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
     @overload
     async def get_e2e_device_keys_and_signatures(
         self,
-        query_list: Collection[Tuple[str, Optional[str]]],
+        query_list: Collection[tuple[str, str | None]],
         include_all_devices: Literal[False] = False,
-    ) -> Dict[str, Dict[str, DeviceKeyLookupResult]]: ...
+    ) -> dict[str, dict[str, DeviceKeyLookupResult]]: ...
 
     @overload
     async def get_e2e_device_keys_and_signatures(
         self,
-        query_list: Collection[Tuple[str, Optional[str]]],
+        query_list: Collection[tuple[str, str | None]],
         include_all_devices: bool = False,
         include_deleted_devices: Literal[False] = False,
-    ) -> Dict[str, Dict[str, DeviceKeyLookupResult]]: ...
+    ) -> dict[str, dict[str, DeviceKeyLookupResult]]: ...
 
     @overload
     async def get_e2e_device_keys_and_signatures(
         self,
-        query_list: Collection[Tuple[str, Optional[str]]],
+        query_list: Collection[tuple[str, str | None]],
         include_all_devices: Literal[True],
         include_deleted_devices: Literal[True],
-    ) -> Dict[str, Dict[str, Optional[DeviceKeyLookupResult]]]: ...
+    ) -> dict[str, dict[str, DeviceKeyLookupResult | None]]: ...
 
     @trace
     @cancellable
     async def get_e2e_device_keys_and_signatures(
         self,
-        query_list: Collection[Tuple[str, Optional[str]]],
+        query_list: Collection[tuple[str, str | None]],
         include_all_devices: bool = False,
         include_deleted_devices: bool = False,
-    ) -> Union[
-        Dict[str, Dict[str, DeviceKeyLookupResult]],
-        Dict[str, Dict[str, Optional[DeviceKeyLookupResult]]],
-    ]:
+    ) -> (
+        dict[str, dict[str, DeviceKeyLookupResult]]
+        | dict[str, dict[str, DeviceKeyLookupResult | None]]
+    ):
         """Fetch a list of device keys
 
         Any cross-signatures made on the keys by the owner of the device are also
@@ -388,18 +382,18 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
 
     async def _get_e2e_device_keys(
         self,
-        query_list: Collection[Tuple[str, Optional[str]]],
+        query_list: Collection[tuple[str, str | None]],
         include_all_devices: bool = False,
         include_deleted_devices: bool = False,
-    ) -> Dict[str, Dict[str, Optional[DeviceKeyLookupResult]]]:
+    ) -> dict[str, dict[str, DeviceKeyLookupResult | None]]:
         """Get information on devices from the database
 
         The results include the device's keys and self-signatures, but *not* any
         cross-signing signatures which have been added subsequently (for which, see
         get_e2e_device_keys_and_signatures)
         """
-        query_clauses: List[str] = []
-        query_params_list: List[List[object]] = []
+        query_clauses: list[str] = []
+        query_params_list: list[list[object]] = []
 
         if include_all_devices is False:
             include_deleted_devices = False
@@ -437,7 +431,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
                 query_clauses.append(user_device_id_in_list_clause)
                 query_params_list.append(user_device_args)
 
-        result: Dict[str, Dict[str, Optional[DeviceKeyLookupResult]]] = {}
+        result: dict[str, dict[str, DeviceKeyLookupResult | None]] = {}
 
         def get_e2e_device_keys_txn(
             txn: LoggingTransaction, query_clause: str, query_params: list
@@ -490,8 +484,8 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
     @cached()
     def _get_e2e_cross_signing_signatures_for_device(
         self,
-        user_id_and_device_id: Tuple[str, str],
-    ) -> Sequence[Tuple[str, str]]:
+        user_id_and_device_id: tuple[str, str],
+    ) -> Sequence[tuple[str, str]]:
         """
         The single-item version of `_get_e2e_cross_signing_signatures_for_devices`.
         See @cachedList for why a separate method is needed.
@@ -503,8 +497,8 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
         list_name="device_query",
     )
     async def _get_e2e_cross_signing_signatures_for_devices(
-        self, device_query: Iterable[Tuple[str, str]]
-    ) -> Mapping[Tuple[str, str], Sequence[Tuple[str, str]]]:
+        self, device_query: Iterable[tuple[str, str]]
+    ) -> Mapping[tuple[str, str], Sequence[tuple[str, str]]]:
         """Get cross-signing signatures for a given list of user IDs and devices.
 
         Args:
@@ -524,8 +518,8 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
         """
 
         def _get_e2e_cross_signing_signatures_for_devices_txn(
-            txn: LoggingTransaction, device_query: Iterable[Tuple[str, str]]
-        ) -> Mapping[Tuple[str, str], Sequence[Tuple[str, str]]]:
+            txn: LoggingTransaction, device_query: Iterable[tuple[str, str]]
+        ) -> Mapping[tuple[str, str], Sequence[tuple[str, str]]]:
             where_clause_sql, where_clause_params = make_tuple_in_list_sql_clause(
                 self.database_engine,
                 columns=("target_user_id", "target_device_id", "user_id"),
@@ -541,7 +535,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
 
             txn.execute(signature_sql, where_clause_params)
 
-            devices_and_signatures: Dict[Tuple[str, str], List[Tuple[str, str]]] = {}
+            devices_and_signatures: dict[tuple[str, str], list[tuple[str, str]]] = {}
 
             # `@cachedList` requires we return one key for every item in `device_query`.
             # Pre-populate `devices_and_signatures` with each key so that none are missing.
@@ -567,8 +561,8 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
         )
 
     async def get_e2e_one_time_keys(
-        self, user_id: str, device_id: str, key_ids: List[str]
-    ) -> Dict[Tuple[str, str], str]:
+        self, user_id: str, device_id: str, key_ids: list[str]
+    ) -> dict[tuple[str, str], str]:
         """Retrieve a number of one-time keys for a user
 
         Args:
@@ -581,7 +575,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
         """
 
         rows = cast(
-            List[Tuple[str, str, str]],
+            list[tuple[str, str, str]],
             await self.db_pool.simple_select_many_batch(
                 table="e2e_one_time_keys_json",
                 column="key_id",
@@ -600,7 +594,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
         user_id: str,
         device_id: str,
         time_now: int,
-        new_keys: Iterable[Tuple[str, str, str]],
+        new_keys: Iterable[tuple[str, str, str]],
     ) -> None:
         """Insert some new one time keys for a device. Errors if any of the
         keys already exist.
@@ -627,7 +621,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
         user_id: str,
         device_id: str,
         time_now: int,
-        new_keys: Iterable[Tuple[str, str, str]],
+        new_keys: Iterable[tuple[str, str, str]],
     ) -> None:
         """Insert some new one time keys for a device. Errors if any of the keys already exist.
 
@@ -674,7 +668,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
             A mapping from algorithm to number of keys for that algorithm.
         """
 
-        def _count_e2e_one_time_keys(txn: LoggingTransaction) -> Dict[str, int]:
+        def _count_e2e_one_time_keys(txn: LoggingTransaction) -> dict[str, int]:
             sql = (
                 "SELECT algorithm, COUNT(key_id) FROM e2e_one_time_keys_json"
                 " WHERE user_id = ? AND device_id = ?"
@@ -901,8 +895,8 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
         )
 
     async def get_e2e_cross_signing_key(
-        self, user_id: str, key_type: str, from_user_id: Optional[str] = None
-    ) -> Optional[JsonMapping]:
+        self, user_id: str, key_type: str, from_user_id: str | None = None
+    ) -> JsonMapping | None:
         """Returns a user's cross-signing key.
 
         Args:
@@ -938,7 +932,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
     )
     async def _get_bare_e2e_cross_signing_keys_bulk(
         self, user_ids: Iterable[str]
-    ) -> Mapping[str, Optional[Mapping[str, JsonMapping]]]:
+    ) -> Mapping[str, Mapping[str, JsonMapping] | None]:
         """Returns the cross-signing keys for a set of users.  The output of this
         function should be passed to _get_e2e_cross_signing_signatures_txn if
         the signatures for the calling user need to be fetched.
@@ -962,7 +956,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
         self,
         txn: LoggingTransaction,
         user_ids: Iterable[str],
-    ) -> Dict[str, Dict[str, JsonDict]]:
+    ) -> dict[str, dict[str, JsonDict]]:
         """Returns the cross-signing keys for a set of users.  The output of this
         function should be passed to _get_e2e_cross_signing_signatures_txn if
         the signatures for the calling user need to be fetched.
@@ -977,7 +971,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
             the dict.
 
         """
-        result: Dict[str, Dict[str, JsonDict]] = {}
+        result: dict[str, dict[str, JsonDict]] = {}
 
         for user_chunk in batch_iter(user_ids, 100):
             clause, params = make_in_list_sql_clause(
@@ -1017,9 +1011,9 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
     def _get_e2e_cross_signing_signatures_txn(
         self,
         txn: LoggingTransaction,
-        keys: Dict[str, Optional[Dict[str, JsonDict]]],
+        keys: dict[str, dict[str, JsonDict] | None],
         from_user_id: str,
-    ) -> Dict[str, Optional[Dict[str, JsonDict]]]:
+    ) -> dict[str, dict[str, JsonDict] | None]:
         """Returns the cross-signing signatures made by a user on a set of keys.
 
         Args:
@@ -1037,7 +1031,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
         # find out what cross-signing keys (a.k.a. devices) we need to get
         # signatures for.  This is a map of (user_id, device_id) to key type
         # (device_id is the key's public part).
-        devices: Dict[Tuple[str, str], str] = {}
+        devices: dict[tuple[str, str], str] = {}
 
         for user_id, user_keys in keys.items():
             if user_keys is None:
@@ -1100,8 +1094,8 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
 
     @cancellable
     async def get_e2e_cross_signing_keys_bulk(
-        self, user_ids: List[str], from_user_id: Optional[str] = None
-    ) -> Mapping[str, Optional[Mapping[str, JsonMapping]]]:
+        self, user_ids: list[str], from_user_id: str | None = None
+    ) -> Mapping[str, Mapping[str, JsonMapping] | None]:
         """Returns the cross-signing keys for a set of users.
 
         Args:
@@ -1118,7 +1112,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
 
         if from_user_id:
             result = cast(
-                Dict[str, Optional[Mapping[str, JsonMapping]]],
+                dict[str, Mapping[str, JsonMapping] | None],
                 await self.db_pool.runInteraction(
                     "get_e2e_cross_signing_signatures",
                     self._get_e2e_cross_signing_signatures_txn,
@@ -1131,7 +1125,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
 
     async def get_all_user_signature_changes_for_remotes(
         self, instance_name: str, last_id: int, current_id: int, limit: int
-    ) -> Tuple[List[Tuple[int, tuple]], int, bool]:
+    ) -> tuple[list[tuple[int, tuple]], int, bool]:
         """Get updates for groups replication stream.
 
         Note that the user signature stream represents when a user signs their
@@ -1163,7 +1157,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
 
         def _get_all_user_signature_changes_for_remotes_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[List[Tuple[int, tuple]], int, bool]:
+        ) -> tuple[list[tuple[int, tuple]], int, bool]:
             sql = """
                 SELECT stream_id, from_user_id AS user_id
                 FROM user_signature_stream
@@ -1194,9 +1188,9 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
         ...
 
     async def claim_e2e_one_time_keys(
-        self, query_list: Collection[Tuple[str, str, str, int]]
-    ) -> Tuple[
-        Dict[str, Dict[str, Dict[str, JsonDict]]], List[Tuple[str, str, str, int]]
+        self, query_list: Collection[tuple[str, str, str, int]]
+    ) -> tuple[
+        dict[str, dict[str, dict[str, JsonDict]]], list[tuple[str, str, str, int]]
     ]:
         """Take a list of one time keys out of the database.
 
@@ -1211,12 +1205,12 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
                 may be less than the input counts. In this case, the returned counts
                 are the number of claims that were not fulfilled.
         """
-        results: Dict[str, Dict[str, Dict[str, JsonDict]]] = {}
-        missing: List[Tuple[str, str, str, int]] = []
+        results: dict[str, dict[str, dict[str, JsonDict]]] = {}
+        missing: list[tuple[str, str, str, int]] = []
         if isinstance(self.database_engine, PostgresEngine):
             # If we can use execute_values we can use a single batch query
             # in autocommit mode.
-            unfulfilled_claim_counts: Dict[Tuple[str, str, str], int] = {}
+            unfulfilled_claim_counts: dict[tuple[str, str, str], int] = {}
             for user_id, device_id, algorithm, count in query_list:
                 unfulfilled_claim_counts[user_id, device_id, algorithm] = count
 
@@ -1265,8 +1259,8 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
         return results, missing
 
     async def claim_e2e_fallback_keys(
-        self, query_list: Iterable[Tuple[str, str, str, bool]]
-    ) -> Dict[str, Dict[str, Dict[str, JsonDict]]]:
+        self, query_list: Iterable[tuple[str, str, str, bool]]
+    ) -> dict[str, dict[str, dict[str, JsonDict]]]:
         """Take a list of fallback keys out of the database.
 
         Args:
@@ -1293,13 +1287,13 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
     def _claim_e2e_fallback_keys_bulk_txn(
         self,
         txn: LoggingTransaction,
-        query_list: Iterable[Tuple[str, str, str, bool]],
-    ) -> Dict[str, Dict[str, Dict[str, JsonDict]]]:
+        query_list: Iterable[tuple[str, str, str, bool]],
+    ) -> dict[str, dict[str, dict[str, JsonDict]]]:
         """Efficient implementation of claim_e2e_fallback_keys for Postgres.
 
         Safe to autocommit: this is a single query.
         """
-        results: Dict[str, Dict[str, Dict[str, JsonDict]]] = {}
+        results: dict[str, dict[str, dict[str, JsonDict]]] = {}
 
         sql = """
             WITH claims(user_id, device_id, algorithm, mark_as_used) AS (
@@ -1312,11 +1306,11 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
             RETURNING k.user_id, k.device_id, k.algorithm, k.key_id, k.key_json;
         """
         claimed_keys = cast(
-            List[Tuple[str, str, str, str, str]],
+            list[tuple[str, str, str, str, str]],
             txn.execute_values(sql, query_list),
         )
 
-        seen_user_device: Set[Tuple[str, str]] = set()
+        seen_user_device: set[tuple[str, str]] = set()
         for user_id, device_id, algorithm, key_id, key_json in claimed_keys:
             device_results = results.setdefault(user_id, {}).setdefault(device_id, {})
             device_results[f"{algorithm}:{key_id}"] = json_decoder.decode(key_json)
@@ -1330,10 +1324,10 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
 
     async def _claim_e2e_fallback_keys_simple(
         self,
-        query_list: Iterable[Tuple[str, str, str, bool]],
-    ) -> Dict[str, Dict[str, Dict[str, JsonDict]]]:
+        query_list: Iterable[tuple[str, str, str, bool]],
+    ) -> dict[str, dict[str, dict[str, JsonDict]]]:
         """Naive, inefficient implementation of claim_e2e_fallback_keys for SQLite."""
-        results: Dict[str, Dict[str, Dict[str, JsonDict]]] = {}
+        results: dict[str, dict[str, dict[str, JsonDict]]] = {}
         for user_id, device_id, algorithm, mark_as_used in query_list:
             row = await self.db_pool.simple_select_one(
                 table="e2e_fallback_keys_json",
@@ -1381,7 +1375,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
         device_id: str,
         algorithm: str,
         count: int,
-    ) -> List[Tuple[str, str]]:
+    ) -> list[tuple[str, str]]:
         """Claim OTK for device for DBs that don't support RETURNING.
 
         Returns:
@@ -1426,8 +1420,8 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
     def _claim_e2e_one_time_keys_bulk(
         self,
         txn: LoggingTransaction,
-        query_list: Iterable[Tuple[str, str, str, int]],
-    ) -> List[Tuple[str, str, str, str, str]]:
+        query_list: Iterable[tuple[str, str, str, int]],
+    ) -> list[tuple[str, str, str, str, str]]:
         """Bulk claim OTKs, for DBs that support DELETE FROM... RETURNING.
 
         Args:
@@ -1466,7 +1460,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
             RETURNING user_id, device_id, algorithm, key_id, key_json;
         """
         otk_rows = cast(
-            List[Tuple[str, str, str, str, str]], txn.execute_values(sql, query_list)
+            list[tuple[str, str, str, str, str]], txn.execute_values(sql, query_list)
         )
 
         seen_user_device = {
@@ -1482,7 +1476,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
 
     async def get_master_cross_signing_key_updatable_before(
         self, user_id: str
-    ) -> Tuple[bool, Optional[int]]:
+    ) -> tuple[bool, int | None]:
         """Get time before which a master cross-signing key may be replaced without UIA.
 
         (UIA means "User-Interactive Auth".)
@@ -1503,7 +1497,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
 
         """
 
-        def impl(txn: LoggingTransaction) -> Tuple[bool, Optional[int]]:
+        def impl(txn: LoggingTransaction) -> tuple[bool, int | None]:
             # We want to distinguish between three cases:
             txn.execute(
                 """
@@ -1515,7 +1509,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
             """,
                 (user_id,),
             )
-            row = cast(Optional[Tuple[Optional[int]]], txn.fetchone())
+            row = cast(tuple[int | None] | None, txn.fetchone())
             if row is None:
                 return False, None
             return True, row[0]
@@ -1527,7 +1521,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
 
     async def delete_old_otks_for_next_user_batch(
         self, after_user_id: str, number_of_users: int
-    ) -> Tuple[List[str], int]:
+    ) -> tuple[list[str], int]:
         """Deletes old OTKs belonging to the next batch of users
 
         Returns:
@@ -1536,7 +1530,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
              * `rows` is the number of deleted rows
         """
 
-        def impl(txn: LoggingTransaction) -> Tuple[List[str], int]:
+        def impl(txn: LoggingTransaction) -> tuple[list[str], int]:
             # Find a batch of users
             txn.execute(
                 """
@@ -1564,7 +1558,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
                 DELETE FROM e2e_one_time_keys_json
                 WHERE {clause} AND ts_added_ms < ? AND length(key_id) = 6
                 """
-            args.append(self._clock.time_msec() - (7 * 24 * 3600 * 1000))
+            args.append(self.clock.time_msec() - (7 * 24 * 3600 * 1000))
             txn.execute(sql, args)
 
             return users, txn.rowcount
@@ -1575,7 +1569,7 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
 
     async def allow_master_cross_signing_key_replacement_without_uia(
         self, user_id: str, duration_ms: int
-    ) -> Optional[int]:
+    ) -> int | None:
         """Mark this user's latest master key as being replaceable without UIA.
 
         Said replacement will only be permitted for a short time after calling this
@@ -1585,9 +1579,9 @@ class EndToEndKeyWorkerStore(EndToEndKeyBackgroundStore, CacheInvalidationWorker
             None, if there is no such key.
             Otherwise, the timestamp before which replacement is allowed without UIA.
         """
-        timestamp = self._clock.time_msec() + duration_ms
+        timestamp = self.clock.time_msec() + duration_ms
 
-        def impl(txn: LoggingTransaction) -> Optional[int]:
+        def impl(txn: LoggingTransaction) -> int | None:
             txn.execute(
                 """
                 UPDATE e2e_cross_signing_keys
diff --git a/synapse/storage/databases/main/event_federation.py b/synapse/storage/databases/main/event_federation.py
index 5c9bd2e848..b2f0aeaf58 100644
--- a/synapse/storage/databases/main/event_federation.py
+++ b/synapse/storage/databases/main/event_federation.py
@@ -25,15 +25,9 @@ from queue import Empty, PriorityQueue
 from typing import (
     TYPE_CHECKING,
     Collection,
-    Dict,
-    FrozenSet,
     Generator,
     Iterable,
-    List,
-    Optional,
     Sequence,
-    Set,
-    Tuple,
     cast,
 )
 
@@ -132,9 +126,9 @@ class BackfillQueueNavigationItem:
 @attr.s(frozen=True, slots=True, auto_attribs=True)
 class StateDifference:
     # The event IDs in the auth difference.
-    auth_difference: Set[str]
+    auth_difference: set[str]
     # The event IDs in the conflicted state subgraph. Used in v2.1 only.
-    conflicted_subgraph: Optional[Set[str]]
+    conflicted_subgraph: set[str] | None
 
 
 class _NoChainCoverIndex(Exception):
@@ -147,7 +141,7 @@ class EventFederationWorkerStore(
 ):
     # TODO: this attribute comes from EventPushActionWorkerStore. Should we inherit from
     # that store so that mypy can deduce this for itself?
-    stream_ordering_month_ago: Optional[int]
+    stream_ordering_month_ago: int | None
 
     def __init__(
         self,
@@ -165,8 +159,9 @@ class EventFederationWorkerStore(
             )
 
         # Cache of event ID to list of auth event IDs and their depths.
-        self._event_auth_cache: LruCache[str, List[Tuple[str, int]]] = LruCache(
+        self._event_auth_cache: LruCache[str, list[tuple[str, int]]] = LruCache(
             max_size=500000,
+            clock=self.hs.get_clock(),
             server_name=self.server_name,
             cache_name="_event_auth_cache",
             size_callback=len,
@@ -176,7 +171,7 @@ class EventFederationWorkerStore(
         # index.
         self.tests_allow_no_chain_cover_index = True
 
-        self._clock.looping_call(self._get_stats_for_federation_staging, 30 * 1000)
+        self.clock.looping_call(self._get_stats_for_federation_staging, 30 * 1000)
 
         if isinstance(self.database_engine, PostgresEngine):
             self.db_pool.updates.register_background_validate_constraint_and_delete_rows(
@@ -198,7 +193,7 @@ class EventFederationWorkerStore(
 
     async def get_auth_chain(
         self, room_id: str, event_ids: Collection[str], include_given: bool = False
-    ) -> List[EventBase]:
+    ) -> list[EventBase]:
         """Get auth events for given event_ids. The events *must* be state events.
 
         Args:
@@ -221,7 +216,7 @@ class EventFederationWorkerStore(
         room_id: str,
         event_ids: Collection[str],
         include_given: bool = False,
-    ) -> Set[str]:
+    ) -> set[str]:
         """Get auth events for given event_ids. The events *must* be state events.
 
         Args:
@@ -266,7 +261,7 @@ class EventFederationWorkerStore(
         room_id: str,
         event_ids: Collection[str],
         include_given: bool,
-    ) -> Set[str]:
+    ) -> set[str]:
         """Calculates the auth chain IDs using the chain index."""
 
         # First we look up the chain ID/sequence numbers for the given events.
@@ -274,10 +269,10 @@ class EventFederationWorkerStore(
         initial_events = set(event_ids)
 
         # All the events that we've found that are reachable from the events.
-        seen_events: Set[str] = set()
+        seen_events: set[str] = set()
 
         # A map from chain ID to max sequence number of the given events.
-        event_chains: Dict[int, int] = {}
+        event_chains: dict[int, int] = {}
 
         sql = """
             SELECT event_id, chain_id, sequence_number
@@ -312,7 +307,7 @@ class EventFederationWorkerStore(
         # are reachable from any event.
 
         # A map from chain ID to max sequence number *reachable* from any event ID.
-        chains: Dict[int, int] = {}
+        chains: dict[int, int] = {}
         for links in self._get_chain_links(txn, set(event_chains.keys())):
             for chain_id in links:
                 if chain_id not in event_chains:
@@ -365,8 +360,8 @@ class EventFederationWorkerStore(
 
     @classmethod
     def _get_chain_links(
-        cls, txn: LoggingTransaction, chains_to_fetch: Set[int]
-    ) -> Generator[Dict[int, List[Tuple[int, int, int]]], None, None]:
+        cls, txn: LoggingTransaction, chains_to_fetch: set[int]
+    ) -> Generator[dict[int, list[tuple[int, int, int]]], None, None]:
         """Fetch all auth chain links from the given set of chains, and all
         links from those chains, recursively.
 
@@ -409,7 +404,7 @@ class EventFederationWorkerStore(
             )
             txn.execute(sql % (clause,), args)
 
-            links: Dict[int, List[Tuple[int, int, int]]] = {}
+            links: dict[int, list[tuple[int, int, int]]] = {}
 
             for (
                 origin_chain_id,
@@ -427,7 +422,7 @@ class EventFederationWorkerStore(
 
     def _get_auth_chain_ids_txn(
         self, txn: LoggingTransaction, event_ids: Collection[str], include_given: bool
-    ) -> Set[str]:
+    ) -> set[str]:
         """Calculates the auth chain IDs.
 
         This is used when we don't have a cover index for the room.
@@ -448,10 +443,10 @@ class EventFederationWorkerStore(
 
         front = set(event_ids)
         while front:
-            new_front: Set[str] = set()
+            new_front: set[str] = set()
             for chunk in batch_iter(front, 100):
                 # Pull the auth events either from the cache or DB.
-                to_fetch: List[str] = []  # Event IDs to fetch from DB
+                to_fetch: list[str] = []  # Event IDs to fetch from DB
                 for event_id in chunk:
                     res = self._event_auth_cache.get(event_id)
                     if res is None:
@@ -467,7 +462,7 @@ class EventFederationWorkerStore(
 
                     # Note we need to batch up the results by event ID before
                     # adding to the cache.
-                    to_cache: Dict[str, List[Tuple[str, int]]] = {}
+                    to_cache: dict[str, list[tuple[str, int]]] = {}
                     for event_id, auth_event_id, auth_event_depth in txn:
                         to_cache.setdefault(event_id, []).append(
                             (auth_event_id, auth_event_depth)
@@ -487,8 +482,8 @@ class EventFederationWorkerStore(
     async def get_auth_chain_difference(
         self,
         room_id: str,
-        state_sets: List[Set[str]],
-    ) -> Set[str]:
+        state_sets: list[set[str]],
+    ) -> set[str]:
         state_diff = await self.get_auth_chain_difference_extended(
             room_id, state_sets, None, None
         )
@@ -497,9 +492,9 @@ class EventFederationWorkerStore(
     async def get_auth_chain_difference_extended(
         self,
         room_id: str,
-        state_sets: List[Set[str]],
-        conflicted_set: Optional[Set[str]],
-        additional_backwards_reachable_conflicted_events: Optional[Set[str]],
+        state_sets: list[set[str]],
+        conflicted_set: set[str] | None,
+        additional_backwards_reachable_conflicted_events: set[str] | None,
     ) -> StateDifference:
         """ "Given sets of state events figure out the auth chain difference (as
         per state res v2 algorithm).
@@ -559,9 +554,9 @@ class EventFederationWorkerStore(
         self,
         txn: LoggingTransaction,
         room_id: str,
-        state_sets: List[Set[str]],
-        conflicted_set: Optional[Set[str]] = None,
-        additional_backwards_reachable_conflicted_events: Optional[Set[str]] = None,
+        state_sets: list[set[str]],
+        conflicted_set: set[str] | None = None,
+        additional_backwards_reachable_conflicted_events: set[str] | None = None,
     ) -> StateDifference:
         """Calculates the auth chain difference using the chain index.
 
@@ -586,14 +581,14 @@ class EventFederationWorkerStore(
                 )
 
         # Map from event_id -> (chain ID, seq no)
-        chain_info: Dict[str, Tuple[int, int]] = {}
+        chain_info: dict[str, tuple[int, int]] = {}
 
         # Map from chain ID -> seq no -> event Id
-        chain_to_event: Dict[int, Dict[int, str]] = {}
+        chain_to_event: dict[int, dict[int, str]] = {}
 
         # All the chains that we've found that are reachable from the state
         # sets.
-        seen_chains: Set[int] = set()
+        seen_chains: set[int] = set()
 
         # Fetch the chain cover index for the initial set of events we're
         # considering.
@@ -620,7 +615,7 @@ class EventFederationWorkerStore(
         events_missing_chain_info = initial_events.difference(chain_info)
 
         # The result set to return, i.e. the auth chain difference.
-        auth_difference_result: Set[str] = set()
+        auth_difference_result: set[str] = set()
 
         if events_missing_chain_info:
             # For some reason we have events we haven't calculated the chain
@@ -651,21 +646,21 @@ class EventFederationWorkerStore(
 
         # A subset of chain_info for conflicted events only, as we need to
         # loop all conflicted chain positions. Map from event_id -> (chain ID, seq no)
-        conflicted_chain_positions: Dict[str, Tuple[int, int]] = {}
+        conflicted_chain_positions: dict[str, tuple[int, int]] = {}
         # For each chain, remember the positions where conflicted events are.
         # We need this for calculating the forward reachable events.
-        conflicted_chain_to_seq: Dict[int, Set[int]] = {}  # chain_id => {seq_num}
+        conflicted_chain_to_seq: dict[int, set[int]] = {}  # chain_id => {seq_num}
         #  A subset of chain_info for additional backwards reachable events only, as we need to
         # loop all additional backwards reachable events for calculating backwards reachable events.
-        additional_backwards_reachable_positions: Dict[
-            str, Tuple[int, int]
+        additional_backwards_reachable_positions: dict[
+            str, tuple[int, int]
         ] = {}  # event_id => (chain_id, seq_num)
         # These next two fields are critical as the intersection of them is the conflicted subgraph.
         # We'll populate them when we walk the chain links.
         # chain_id => max(seq_num) backwards reachable (e.g 4 means 1,2,3,4 are backwards reachable)
-        conflicted_backwards_reachable: Dict[int, int] = {}
+        conflicted_backwards_reachable: dict[int, int] = {}
         # chain_id => min(seq_num) forwards reachable (e.g 4 means 4,5,6..n are forwards reachable)
-        conflicted_forwards_reachable: Dict[int, int] = {}
+        conflicted_forwards_reachable: dict[int, int] = {}
 
         # populate the v2.1 data structures
         if is_state_res_v21:
@@ -687,9 +682,9 @@ class EventFederationWorkerStore(
 
         # Corresponds to `state_sets`, except as a map from chain ID to max
         # sequence number reachable from the state set.
-        set_to_chain: List[Dict[int, int]] = []
+        set_to_chain: list[dict[int, int]] = []
         for state_set in state_sets:
-            chains: Dict[int, int] = {}
+            chains: dict[int, int] = {}
             set_to_chain.append(chains)
 
             for state_id in state_set:
@@ -801,7 +796,7 @@ class EventFederationWorkerStore(
 
         # Mapping from chain ID to the range of sequence numbers that should be
         # pulled from the database.
-        auth_diff_chain_to_gap: Dict[int, Tuple[int, int]] = {}
+        auth_diff_chain_to_gap: dict[int, tuple[int, int]] = {}
 
         for chain_id in seen_chains:
             min_seq_no = min(chains.get(chain_id, 0) for chains in set_to_chain)
@@ -819,10 +814,10 @@ class EventFederationWorkerStore(
                         auth_diff_chain_to_gap[chain_id] = (min_seq_no, max_seq_no)
                         break
 
-        conflicted_subgraph_result: Set[str] = set()
+        conflicted_subgraph_result: set[str] = set()
         # Mapping from chain ID to the range of sequence numbers that should be
         # pulled from the database.
-        conflicted_subgraph_chain_to_gap: Dict[int, Tuple[int, int]] = {}
+        conflicted_subgraph_chain_to_gap: dict[int, tuple[int, int]] = {}
         if is_state_res_v21:
             # also include the conflicted subgraph using backward/forward reachability info from all
             # the conflicted events. To calculate this, we want to extract the intersection between
@@ -881,9 +876,9 @@ class EventFederationWorkerStore(
         )
 
     def _fetch_event_ids_from_chains_txn(
-        self, txn: LoggingTransaction, chains: Dict[int, Tuple[int, int]]
-    ) -> Set[str]:
-        result: Set[str] = set()
+        self, txn: LoggingTransaction, chains: dict[int, tuple[int, int]]
+    ) -> set[str]:
+        result: set[str] = set()
         if isinstance(self.database_engine, PostgresEngine):
             # We can use `execute_values` to efficiently fetch the gaps when
             # using postgres.
@@ -917,10 +912,10 @@ class EventFederationWorkerStore(
         self,
         txn: LoggingTransaction,
         room_id: str,
-        state_sets: List[Set[str]],
-        events_missing_chain_info: Set[str],
+        state_sets: list[set[str]],
+        events_missing_chain_info: set[str],
         events_that_have_chain_index: Collection[str],
-    ) -> Set[str]:
+    ) -> set[str]:
         """Helper for `_get_auth_chain_difference_using_cover_index_txn` to
         handle the case where we haven't calculated the chain cover index for
         all events.
@@ -961,7 +956,7 @@ class EventFederationWorkerStore(
             WHERE tc.room_id = ?
         """
         txn.execute(sql, (room_id,))
-        event_to_auth_ids: Dict[str, Set[str]] = {}
+        event_to_auth_ids: dict[str, set[str]] = {}
         events_that_have_chain_index = set(events_that_have_chain_index)
         for event_id, auth_id, auth_id_has_chain in txn:
             s = event_to_auth_ids.setdefault(event_id, set())
@@ -981,7 +976,7 @@ class EventFederationWorkerStore(
             raise _NoChainCoverIndex(room_id)
 
         # Create a map from event IDs we care about to their partial auth chain.
-        event_id_to_partial_auth_chain: Dict[str, Set[str]] = {}
+        event_id_to_partial_auth_chain: dict[str, set[str]] = {}
         for event_id, auth_ids in event_to_auth_ids.items():
             if not any(event_id in state_set for state_set in state_sets):
                 continue
@@ -1004,7 +999,7 @@ class EventFederationWorkerStore(
         #   1. Update the state sets to only include indexed events; and
         #   2. Create a new list containing the auth chains of the un-indexed
         #      events
-        unindexed_state_sets: List[Set[str]] = []
+        unindexed_state_sets: list[set[str]] = []
         for state_set in state_sets:
             unindexed_state_set = set()
             for event_id, auth_chain in event_id_to_partial_auth_chain.items():
@@ -1030,8 +1025,8 @@ class EventFederationWorkerStore(
         return union - intersection
 
     def _get_auth_chain_difference_txn(
-        self, txn: LoggingTransaction, state_sets: List[Set[str]]
-    ) -> Set[str]:
+        self, txn: LoggingTransaction, state_sets: list[set[str]]
+    ) -> set[str]:
         """Calculates the auth chain difference using a breadth first search.
 
         This is used when we don't have a cover index for the room.
@@ -1086,7 +1081,7 @@ class EventFederationWorkerStore(
         }
 
         # The sorted list of events whose auth chains we should walk.
-        search: List[Tuple[int, str]] = []
+        search: list[tuple[int, str]] = []
 
         # We need to get the depth of the initial events for sorting purposes.
         sql = """
@@ -1103,13 +1098,13 @@ class EventFederationWorkerStore(
 
             # I think building a temporary list with fetchall is more efficient than
             # just `search.extend(txn)`, but this is unconfirmed
-            search.extend(cast(List[Tuple[int, str]], txn.fetchall()))
+            search.extend(cast(list[tuple[int, str]], txn.fetchall()))
 
         # sort by depth
         search.sort()
 
         # Map from event to its auth events
-        event_to_auth_events: Dict[str, Set[str]] = {}
+        event_to_auth_events: dict[str, set[str]] = {}
 
         base_sql = """
             SELECT a.event_id, auth_id, depth
@@ -1128,8 +1123,8 @@ class EventFederationWorkerStore(
             # currently walking, either from cache or DB.
             search, chunk = search[:-100], search[-100:]
 
-            found: List[Tuple[str, str, int]] = []  # Results found
-            to_fetch: List[str] = []  # Event IDs to fetch from DB
+            found: list[tuple[str, str, int]] = []  # Results found
+            to_fetch: list[str] = []  # Event IDs to fetch from DB
             for _, event_id in chunk:
                 res = self._event_auth_cache.get(event_id)
                 if res is None:
@@ -1146,7 +1141,7 @@ class EventFederationWorkerStore(
                 # We parse the results and add the to the `found` set and the
                 # cache (note we need to batch up the results by event ID before
                 # adding to the cache).
-                to_cache: Dict[str, List[Tuple[str, int]]] = {}
+                to_cache: dict[str, list[tuple[str, int]]] = {}
                 for event_id, auth_event_id, auth_event_depth in txn:
                     to_cache.setdefault(event_id, []).append(
                         (auth_event_id, auth_event_depth)
@@ -1203,7 +1198,7 @@ class EventFederationWorkerStore(
         room_id: str,
         current_depth: int,
         limit: int,
-    ) -> List[Tuple[str, int]]:
+    ) -> list[tuple[str, int]]:
         """
         Get the backward extremities to backfill from in the room along with the
         approximate depth.
@@ -1234,7 +1229,7 @@ class EventFederationWorkerStore(
 
         def get_backfill_points_in_room_txn(
             txn: LoggingTransaction, room_id: str
-        ) -> List[Tuple[str, int]]:
+        ) -> list[tuple[str, int]]:
             # Assemble a tuple lookup of event_id -> depth for the oldest events
             # we know of in the room. Backwards extremeties are the oldest
             # events we know of in the room but we only know of them because
@@ -1328,14 +1323,14 @@ class EventFederationWorkerStore(
                 (
                     room_id,
                     current_depth,
-                    self._clock.time_msec(),
+                    self.clock.time_msec(),
                     BACKFILL_EVENT_EXPONENTIAL_BACKOFF_MAXIMUM_DOUBLING_STEPS,
                     BACKFILL_EVENT_EXPONENTIAL_BACKOFF_STEP_MILLISECONDS,
                     limit,
                 ),
             )
 
-            return cast(List[Tuple[str, int]], txn.fetchall())
+            return cast(list[tuple[str, int]], txn.fetchall())
 
         return await self.db_pool.runInteraction(
             "get_backfill_points_in_room",
@@ -1345,14 +1340,14 @@ class EventFederationWorkerStore(
 
     async def get_max_depth_of(
         self, event_ids: Collection[str]
-    ) -> Tuple[Optional[str], int]:
+    ) -> tuple[str | None, int]:
         """Returns the event ID and depth for the event that has the max depth from a set of event IDs
 
         Args:
             event_ids: The event IDs to calculate the max depth of.
         """
         rows = cast(
-            List[Tuple[str, int]],
+            list[tuple[str, int]],
             await self.db_pool.simple_select_many_batch(
                 table="events",
                 column="event_id",
@@ -1377,14 +1372,14 @@ class EventFederationWorkerStore(
 
             return max_depth_event_id, current_max_depth
 
-    async def get_min_depth_of(self, event_ids: List[str]) -> Tuple[Optional[str], int]:
+    async def get_min_depth_of(self, event_ids: list[str]) -> tuple[str | None, int]:
         """Returns the event ID and depth for the event that has the min depth from a set of event IDs
 
         Args:
             event_ids: The event IDs to calculate the max depth of.
         """
         rows = cast(
-            List[Tuple[str, int]],
+            list[tuple[str, int]],
             await self.db_pool.simple_select_many_batch(
                 table="events",
                 column="event_id",
@@ -1409,7 +1404,7 @@ class EventFederationWorkerStore(
 
             return min_depth_event_id, current_min_depth
 
-    async def get_prev_events_for_room(self, room_id: str) -> List[str]:
+    async def get_prev_events_for_room(self, room_id: str) -> list[str]:
         """
         Gets a subset of the current forward extremities in the given room.
 
@@ -1430,7 +1425,7 @@ class EventFederationWorkerStore(
 
     def _get_prev_events_for_room_txn(
         self, txn: LoggingTransaction, room_id: str
-    ) -> List[str]:
+    ) -> list[str]:
         # we just use the 10 newest events. Older events will become
         # prev_events of future events.
 
@@ -1448,7 +1443,7 @@ class EventFederationWorkerStore(
 
     async def get_rooms_with_many_extremities(
         self, min_count: int, limit: int, room_id_filter: Iterable[str]
-    ) -> List[str]:
+    ) -> list[str]:
         """Get the top rooms with at least N extremities.
 
         Args:
@@ -1461,7 +1456,7 @@ class EventFederationWorkerStore(
             sorted by extremity count.
         """
 
-        def _get_rooms_with_many_extremities_txn(txn: LoggingTransaction) -> List[str]:
+        def _get_rooms_with_many_extremities_txn(txn: LoggingTransaction) -> list[str]:
             where_clause = "1=1"
             if room_id_filter:
                 where_clause = "room_id NOT IN (%s)" % (
@@ -1486,7 +1481,7 @@ class EventFederationWorkerStore(
         )
 
     @cached(max_entries=5000, iterable=True)
-    async def get_latest_event_ids_in_room(self, room_id: str) -> FrozenSet[str]:
+    async def get_latest_event_ids_in_room(self, room_id: str) -> frozenset[str]:
         event_ids = await self.db_pool.simple_select_onecol(
             table="event_forward_extremities",
             keyvalues={"room_id": room_id},
@@ -1495,7 +1490,7 @@ class EventFederationWorkerStore(
         )
         return frozenset(event_ids)
 
-    async def get_min_depth(self, room_id: str) -> Optional[int]:
+    async def get_min_depth(self, room_id: str) -> int | None:
         """For the given room, get the minimum depth we have seen for it."""
         return await self.db_pool.runInteraction(
             "get_min_depth", self._get_min_depth_interaction, room_id
@@ -1503,7 +1498,7 @@ class EventFederationWorkerStore(
 
     def _get_min_depth_interaction(
         self, txn: LoggingTransaction, room_id: str
-    ) -> Optional[int]:
+    ) -> int | None:
         min_depth = self.db_pool.simple_select_one_onecol_txn(
             txn,
             table="room_depth",
@@ -1609,7 +1604,7 @@ class EventFederationWorkerStore(
                 WHERE room_id = ?
         """
 
-        def get_forward_extremeties_for_room_txn(txn: LoggingTransaction) -> List[str]:
+        def get_forward_extremeties_for_room_txn(txn: LoggingTransaction) -> list[str]:
             txn.execute(sql, (stream_ordering, room_id))
             return [event_id for (event_id,) in txn]
 
@@ -1626,7 +1621,7 @@ class EventFederationWorkerStore(
 
     def _get_connected_prev_event_backfill_results_txn(
         self, txn: LoggingTransaction, event_id: str, limit: int
-    ) -> List[BackfillQueueNavigationItem]:
+    ) -> list[BackfillQueueNavigationItem]:
         """
         Find any events connected by prev_event the specified event_id.
 
@@ -1674,8 +1669,8 @@ class EventFederationWorkerStore(
         ]
 
     async def get_backfill_events(
-        self, room_id: str, seed_event_id_list: List[str], limit: int
-    ) -> List[EventBase]:
+        self, room_id: str, seed_event_id_list: list[str], limit: int
+    ) -> list[EventBase]:
         """Get a list of Events for a given topic that occurred before (and
         including) the events in seed_event_id_list. Return a list of max size `limit`
 
@@ -1693,7 +1688,7 @@ class EventFederationWorkerStore(
         )
         events = await self.get_events_as_list(event_ids)
         return sorted(
-            # type-ignore: mypy doesn't like negating the Optional[int] stream_ordering.
+            # type-ignore: mypy doesn't like negating the int | None stream_ordering.
             # But it's never None, because these events were previously persisted to the DB.
             events,
             key=lambda e: (-e.depth, -e.internal_metadata.stream_ordering),  # type: ignore[operator]
@@ -1703,9 +1698,9 @@ class EventFederationWorkerStore(
         self,
         txn: LoggingTransaction,
         room_id: str,
-        seed_event_id_list: List[str],
+        seed_event_id_list: list[str],
         limit: int,
-    ) -> Set[str]:
+    ) -> set[str]:
         """
         We want to make sure that we do a breadth-first, "depth" ordered search.
         We also handle navigating historical branches of history connected by
@@ -1718,7 +1713,7 @@ class EventFederationWorkerStore(
             limit,
         )
 
-        event_id_results: Set[str] = set()
+        event_id_results: set[str] = set()
 
         # In a PriorityQueue, the lowest valued entries are retrieved first.
         # We're using depth as the priority in the queue and tie-break based on
@@ -1726,7 +1721,7 @@ class EventFederationWorkerStore(
         # highest and newest-in-time message. We add events to the queue with a
         # negative depth so that we process the newest-in-time messages first
         # going backwards in time. stream_ordering follows the same pattern.
-        queue: "PriorityQueue[Tuple[int, int, str, str]]" = PriorityQueue()
+        queue: "PriorityQueue[tuple[int, int, str, str]]" = PriorityQueue()
 
         for seed_event_id in seed_event_id_list:
             event_lookup_result = self.db_pool.simple_select_one_txn(
@@ -1841,12 +1836,12 @@ class EventFederationWorkerStore(
                 last_cause=EXCLUDED.last_cause;
         """
 
-        txn.execute(sql, (room_id, event_id, 1, self._clock.time_msec(), cause))
+        txn.execute(sql, (room_id, event_id, 1, self.clock.time_msec(), cause))
 
     @trace
     async def get_event_ids_with_failed_pull_attempts(
         self, event_ids: StrCollection
-    ) -> Set[str]:
+    ) -> set[str]:
         """
         Filter the given list of `event_ids` and return events which have any failed
         pull attempts.
@@ -1859,7 +1854,7 @@ class EventFederationWorkerStore(
         """
 
         rows = cast(
-            List[Tuple[str]],
+            list[tuple[str]],
             await self.db_pool.simple_select_many_batch(
                 table="event_failed_pull_attempts",
                 column="event_id",
@@ -1876,7 +1871,7 @@ class EventFederationWorkerStore(
         self,
         room_id: str,
         event_ids: Collection[str],
-    ) -> Dict[str, int]:
+    ) -> dict[str, int]:
         """
         Filter down the events to ones that we've failed to pull before recently. Uses
         exponential backoff.
@@ -1890,7 +1885,7 @@ class EventFederationWorkerStore(
             next timestamp at which we may try pulling them again.
         """
         event_failed_pull_attempts = cast(
-            List[Tuple[str, int, int]],
+            list[tuple[str, int, int]],
             await self.db_pool.simple_select_many_batch(
                 table="event_failed_pull_attempts",
                 column="event_id",
@@ -1905,7 +1900,7 @@ class EventFederationWorkerStore(
             ),
         )
 
-        current_time = self._clock.time_msec()
+        current_time = self.clock.time_msec()
 
         event_ids_with_backoff = {}
         for event_id, last_attempt_ts, num_attempts in event_failed_pull_attempts:
@@ -1931,10 +1926,10 @@ class EventFederationWorkerStore(
     async def get_missing_events(
         self,
         room_id: str,
-        earliest_events: List[str],
-        latest_events: List[str],
+        earliest_events: list[str],
+        latest_events: list[str],
         limit: int,
-    ) -> List[EventBase]:
+    ) -> list[EventBase]:
         ids = await self.db_pool.runInteraction(
             "get_missing_events",
             self._get_missing_events,
@@ -1949,13 +1944,13 @@ class EventFederationWorkerStore(
         self,
         txn: LoggingTransaction,
         room_id: str,
-        earliest_events: List[str],
-        latest_events: List[str],
+        earliest_events: list[str],
+        latest_events: list[str],
         limit: int,
-    ) -> List[str]:
+    ) -> list[str]:
         seen_events = set(earliest_events)
         front = set(latest_events) - seen_events
-        event_results: List[str] = []
+        event_results: list[str] = []
 
         query = (
             "SELECT prev_event_id FROM event_edges "
@@ -1982,7 +1977,7 @@ class EventFederationWorkerStore(
 
     @trace
     @tag_args
-    async def get_successor_events(self, event_id: str) -> List[str]:
+    async def get_successor_events(self, event_id: str) -> list[str]:
         """Fetch all events that have the given event as a prev event
 
         Args:
@@ -2025,7 +2020,7 @@ class EventFederationWorkerStore(
             values={},
             insertion_values={
                 "room_id": event.room_id,
-                "received_ts": self._clock.time_msec(),
+                "received_ts": self.clock.time_msec(),
                 "event_json": json_encoder.encode(event.get_dict()),
                 "internal_metadata": json_encoder.encode(
                     event.internal_metadata.get_dict()
@@ -2038,72 +2033,40 @@ class EventFederationWorkerStore(
         self,
         origin: str,
         event_id: str,
-    ) -> Optional[int]:
+    ) -> int | None:
         """Remove the given event from the staging area.
 
         Returns:
             The received_ts of the row that was deleted, if any.
         """
-        if self.db_pool.engine.supports_returning:
 
-            def _remove_received_event_from_staging_txn(
-                txn: LoggingTransaction,
-            ) -> Optional[int]:
-                sql = """
-                    DELETE FROM federation_inbound_events_staging
-                    WHERE origin = ? AND event_id = ?
-                    RETURNING received_ts
-                """
+        def _remove_received_event_from_staging_txn(
+            txn: LoggingTransaction,
+        ) -> int | None:
+            sql = """
+                DELETE FROM federation_inbound_events_staging
+                WHERE origin = ? AND event_id = ?
+                RETURNING received_ts
+            """
 
-                txn.execute(sql, (origin, event_id))
-                row = cast(Optional[Tuple[int]], txn.fetchone())
+            txn.execute(sql, (origin, event_id))
+            row = cast(tuple[int] | None, txn.fetchone())
 
-                if row is None:
-                    return None
+            if row is None:
+                return None
 
-                return row[0]
+            return row[0]
 
-            return await self.db_pool.runInteraction(
-                "remove_received_event_from_staging",
-                _remove_received_event_from_staging_txn,
-                db_autocommit=True,
-            )
-
-        else:
-
-            def _remove_received_event_from_staging_txn(
-                txn: LoggingTransaction,
-            ) -> Optional[int]:
-                received_ts = self.db_pool.simple_select_one_onecol_txn(
-                    txn,
-                    table="federation_inbound_events_staging",
-                    keyvalues={
-                        "origin": origin,
-                        "event_id": event_id,
-                    },
-                    retcol="received_ts",
-                    allow_none=True,
-                )
-                self.db_pool.simple_delete_txn(
-                    txn,
-                    table="federation_inbound_events_staging",
-                    keyvalues={
-                        "origin": origin,
-                        "event_id": event_id,
-                    },
-                )
-
-                return received_ts
-
-            return await self.db_pool.runInteraction(
-                "remove_received_event_from_staging",
-                _remove_received_event_from_staging_txn,
-            )
+        return await self.db_pool.runInteraction(
+            "remove_received_event_from_staging",
+            _remove_received_event_from_staging_txn,
+            db_autocommit=True,
+        )
 
     async def get_next_staged_event_id_for_room(
         self,
         room_id: str,
-    ) -> Optional[Tuple[str, str]]:
+    ) -> tuple[str, str] | None:
         """
         Get the next event ID in the staging area for the given room.
 
@@ -2113,7 +2076,7 @@ class EventFederationWorkerStore(
 
         def _get_next_staged_event_id_for_room_txn(
             txn: LoggingTransaction,
-        ) -> Optional[Tuple[str, str]]:
+        ) -> tuple[str, str] | None:
             sql = """
                 SELECT origin, event_id
                 FROM federation_inbound_events_staging
@@ -2124,7 +2087,7 @@ class EventFederationWorkerStore(
 
             txn.execute(sql, (room_id,))
 
-            return cast(Optional[Tuple[str, str]], txn.fetchone())
+            return cast(tuple[str, str] | None, txn.fetchone())
 
         return await self.db_pool.runInteraction(
             "get_next_staged_event_id_for_room", _get_next_staged_event_id_for_room_txn
@@ -2134,12 +2097,12 @@ class EventFederationWorkerStore(
         self,
         room_id: str,
         room_version: RoomVersion,
-    ) -> Optional[Tuple[str, EventBase]]:
+    ) -> tuple[str, EventBase] | None:
         """Get the next event in the staging area for the given room."""
 
         def _get_next_staged_event_for_room_txn(
             txn: LoggingTransaction,
-        ) -> Optional[Tuple[str, str, str]]:
+        ) -> tuple[str, str, str] | None:
             sql = """
                 SELECT event_json, internal_metadata, origin
                 FROM federation_inbound_events_staging
@@ -2149,7 +2112,7 @@ class EventFederationWorkerStore(
             """
             txn.execute(sql, (room_id,))
 
-            return cast(Optional[Tuple[str, str, str]], txn.fetchone())
+            return cast(tuple[str, str, str] | None, txn.fetchone())
 
         row = await self.db_pool.runInteraction(
             "get_next_staged_event_for_room", _get_next_staged_event_for_room_txn
@@ -2198,7 +2161,7 @@ class EventFederationWorkerStore(
         # by other events in the queue). We do this so that we can always
         # backpaginate in all the events we have dropped.
         rows = cast(
-            List[Tuple[str, str]],
+            list[tuple[str, str]],
             await self.db_pool.simple_select_list(
                 table="federation_inbound_events_staging",
                 keyvalues={"room_id": room_id},
@@ -2209,8 +2172,8 @@ class EventFederationWorkerStore(
 
         # Find the set of events referenced by those in the queue, as well as
         # collecting all the event IDs in the queue.
-        referenced_events: Set[str] = set()
-        seen_events: Set[str] = set()
+        referenced_events: set[str] = set()
+        seen_events: set[str] = set()
         for event_id, event_json in rows:
             seen_events.add(event_id)
             event_d = db_to_json(event_json)
@@ -2271,7 +2234,7 @@ class EventFederationWorkerStore(
 
         return True
 
-    async def get_all_rooms_with_staged_incoming_events(self) -> List[str]:
+    async def get_all_rooms_with_staged_incoming_events(self) -> list[str]:
         """Get the room IDs of all events currently staged."""
         return await self.db_pool.simple_select_onecol(
             table="federation_inbound_events_staging",
@@ -2286,20 +2249,20 @@ class EventFederationWorkerStore(
 
         def _get_stats_for_federation_staging_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[int, int]:
+        ) -> tuple[int, int]:
             txn.execute("SELECT count(*) FROM federation_inbound_events_staging")
-            (count,) = cast(Tuple[int], txn.fetchone())
+            (count,) = cast(tuple[int], txn.fetchone())
 
             txn.execute(
                 "SELECT min(received_ts) FROM federation_inbound_events_staging"
             )
 
-            (received_ts,) = cast(Tuple[Optional[int]], txn.fetchone())
+            (received_ts,) = cast(tuple[int | None], txn.fetchone())
 
             # If there is nothing in the staging area default it to 0.
             age = 0
             if received_ts is not None:
-                age = self._clock.time_msec() - received_ts
+                age = self.clock.time_msec() - received_ts
 
             return count, age
 
@@ -2408,8 +2371,8 @@ class EventFederationStore(EventFederationWorkerStore):
 def _materialize(
     origin_chain_id: int,
     origin_sequence_number: int,
-    links: Dict[int, List[Tuple[int, int, int]]],
-    materialized: Dict[int, int],
+    links: dict[int, list[tuple[int, int, int]]],
+    materialized: dict[int, int],
     backwards: bool = True,
 ) -> None:
     """Helper function for fetching auth chain links. For a given origin chain
@@ -2467,10 +2430,10 @@ def _materialize(
 
 
 def _generate_forward_links(
-    links: Dict[int, List[Tuple[int, int, int]]],
-) -> Dict[int, List[Tuple[int, int, int]]]:
+    links: dict[int, list[tuple[int, int, int]]],
+) -> dict[int, list[tuple[int, int, int]]]:
     """Reverse the input links from the given backwards links"""
-    new_links: Dict[int, List[Tuple[int, int, int]]] = {}
+    new_links: dict[int, list[tuple[int, int, int]]] = {}
     for origin_chain_id, chain_links in links.items():
         for origin_seq_num, target_chain_id, target_seq_num in chain_links:
             new_links.setdefault(target_chain_id, []).append(
@@ -2480,9 +2443,9 @@ def _generate_forward_links(
 
 
 def accumulate_forwards_reachable_events(
-    conflicted_forwards_reachable: Dict[int, int],
-    back_links: Dict[int, List[Tuple[int, int, int]]],
-    conflicted_chain_positions: Dict[str, Tuple[int, int]],
+    conflicted_forwards_reachable: dict[int, int],
+    back_links: dict[int, list[tuple[int, int, int]]],
+    conflicted_chain_positions: dict[str, tuple[int, int]],
 ) -> None:
     """Accumulate new forwards reachable events using the back_links provided.
 
diff --git a/synapse/storage/databases/main/event_push_actions.py b/synapse/storage/databases/main/event_push_actions.py
index 4db0230421..2e99d7314e 100644
--- a/synapse/storage/databases/main/event_push_actions.py
+++ b/synapse/storage/databases/main/event_push_actions.py
@@ -84,17 +84,14 @@ from collections import defaultdict
 from typing import (
     TYPE_CHECKING,
     Collection,
-    Dict,
-    List,
     Mapping,
-    Optional,
-    Tuple,
-    Union,
     cast,
 )
 
 import attr
 
+from twisted.internet.task import LoopingCall
+
 from synapse.api.constants import MAIN_TIMELINE, ReceiptTypes
 from synapse.metrics.background_process_metrics import wrap_as_background_process
 from synapse.storage._base import SQLBaseStore, db_to_json, make_in_list_sql_clause
@@ -116,11 +113,11 @@ if TYPE_CHECKING:
 logger = logging.getLogger(__name__)
 
 
-DEFAULT_NOTIF_ACTION: List[Union[dict, str]] = [
+DEFAULT_NOTIF_ACTION: list[dict | str] = [
     "notify",
     {"set_tweak": "highlight", "value": False},
 ]
-DEFAULT_HIGHLIGHT_ACTION: List[Union[dict, str]] = [
+DEFAULT_HIGHLIGHT_ACTION: list[dict | str] = [
     "notify",
     {"set_tweak": "sound", "value": "default"},
     {"set_tweak": "highlight"},
@@ -136,7 +133,7 @@ class _RoomReceipt:
 
     unthreaded_stream_ordering: int = 0
     # threaded_stream_ordering includes the main pseudo-thread.
-    threaded_stream_ordering: Dict[str, int] = attr.Factory(dict)
+    threaded_stream_ordering: dict[str, int] = attr.Factory(dict)
 
     def is_unread(self, thread_id: str, stream_ordering: int) -> bool:
         """Returns True if the stream ordering is unread according to the receipt information."""
@@ -163,7 +160,7 @@ class HttpPushAction:
     event_id: str
     room_id: str
     stream_ordering: int
-    actions: List[Union[dict, str]]
+    actions: list[dict | str]
 
 
 @attr.s(slots=True, frozen=True, auto_attribs=True)
@@ -173,7 +170,7 @@ class EmailPushAction(HttpPushAction):
     push notification.
     """
 
-    received_ts: Optional[int]
+    received_ts: int | None
 
 
 @attr.s(slots=True, frozen=True, auto_attribs=True)
@@ -222,9 +219,7 @@ class RoomNotifCounts:
 _EMPTY_ROOM_NOTIF_COUNTS = RoomNotifCounts(NotifCounts(), {})
 
 
-def _serialize_action(
-    actions: Collection[Union[Mapping, str]], is_highlight: bool
-) -> str:
+def _serialize_action(actions: Collection[Mapping | str], is_highlight: bool) -> str:
     """Custom serializer for actions. This allows us to "compress" common actions.
 
     We use the fact that most users have the same actions for notifs (and for
@@ -242,7 +237,7 @@ def _serialize_action(
     return json_encoder.encode(actions)
 
 
-def _deserialize_action(actions: str, is_highlight: bool) -> List[Union[dict, str]]:
+def _deserialize_action(actions: str, is_highlight: bool) -> list[dict | str]:
     """Custom deserializer for actions. This allows us to "compress" common actions"""
     if actions:
         return db_to_json(actions)
@@ -254,6 +249,8 @@ def _deserialize_action(actions: str, is_highlight: bool) -> List[Union[dict, st
 
 
 class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBaseStore):
+    _background_tasks: list[LoopingCall] = []
+
     def __init__(
         self,
         database: DatabasePool,
@@ -263,28 +260,24 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
         super().__init__(database, db_conn, hs)
 
         # Track when the process started.
-        self._started_ts = self._clock.time_msec()
+        self._started_ts = self.clock.time_msec()
 
         # These get correctly set by _find_stream_orderings_for_times_txn
-        self.stream_ordering_month_ago: Optional[int] = None
-        self.stream_ordering_day_ago: Optional[int] = None
+        self.stream_ordering_month_ago: int | None = None
+        self.stream_ordering_day_ago: int | None = None
 
         cur = db_conn.cursor(txn_name="_find_stream_orderings_for_times_txn")
         self._find_stream_orderings_for_times_txn(cur)
         cur.close()
 
-        self.find_stream_orderings_looping_call = self._clock.looping_call(
-            self._find_stream_orderings_for_times, 10 * 60 * 1000
-        )
+        self.clock.looping_call(self._find_stream_orderings_for_times, 10 * 60 * 1000)
 
         self._rotate_count = 10000
         self._doing_notif_rotation = False
         if hs.config.worker.run_background_tasks:
-            self._rotate_notif_loop = self._clock.looping_call(
-                self._rotate_notifs, 30 * 1000
-            )
+            self.clock.looping_call(self._rotate_notifs, 30 * 1000)
 
-            self._clear_old_staging_loop = self._clock.looping_call(
+            self.clock.looping_call(
                 self._clear_old_push_actions_staging, 30 * 60 * 1000
             )
 
@@ -351,7 +344,7 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
         )
         return 0
 
-    async def get_unread_counts_by_room_for_user(self, user_id: str) -> Dict[str, int]:
+    async def get_unread_counts_by_room_for_user(self, user_id: str) -> dict[str, int]:
         """Get the notification count by room for a user. Only considers notifications,
         not highlight or unread counts, and threads are currently aggregated under their room.
 
@@ -373,7 +366,7 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
 
     def _get_unread_counts_by_room_for_user_txn(
         self, txn: LoggingTransaction, user_id: str
-    ) -> Dict[str, int]:
+    ) -> dict[str, int]:
         receipt_types_clause, args = make_in_list_sql_clause(
             self.database_engine,
             "receipt_type",
@@ -440,7 +433,7 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
         txn.execute(sql, args)
 
         seen_thread_ids = set()
-        room_to_count: Dict[str, int] = defaultdict(int)
+        room_to_count: dict[str, int] = defaultdict(int)
 
         for room_id, thread_id, notif_count in txn:
             room_to_count[room_id] += notif_count
@@ -585,7 +578,7 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
         """
 
         main_counts = NotifCounts()
-        thread_counts: Dict[str, NotifCounts] = {}
+        thread_counts: dict[str, NotifCounts] = {}
 
         def _get_thread(thread_id: str) -> NotifCounts:
             if thread_id == MAIN_TIMELINE:
@@ -776,9 +769,9 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
         room_id: str,
         user_id: str,
         stream_ordering: int,
-        max_stream_ordering: Optional[int] = None,
-        thread_id: Optional[str] = None,
-    ) -> List[Tuple[int, int, str]]:
+        max_stream_ordering: int | None = None,
+        thread_id: str | None = None,
+    ) -> list[tuple[int, int, str]]:
         """Returns the notify and unread counts from `event_push_actions` for
         the given user/room in the given range.
 
@@ -840,12 +833,12 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
         """
 
         txn.execute(sql, args)
-        return cast(List[Tuple[int, int, str]], txn.fetchall())
+        return cast(list[tuple[int, int, str]], txn.fetchall())
 
     async def get_push_action_users_in_range(
         self, min_stream_ordering: int, max_stream_ordering: int
-    ) -> List[str]:
-        def f(txn: LoggingTransaction) -> List[str]:
+    ) -> list[str]:
+        def f(txn: LoggingTransaction) -> list[str]:
             sql = (
                 "SELECT DISTINCT(user_id) FROM event_push_actions WHERE"
                 " stream_ordering >= ? AND stream_ordering <= ? AND notif = 1"
@@ -861,7 +854,7 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
         user_id: str,
         room_ids: StrCollection,
         thread_ids: StrCollection,
-    ) -> Dict[str, _RoomReceipt]:
+    ) -> dict[str, _RoomReceipt]:
         """
         Get (private) read receipts for a user in each of the given room IDs
         and thread IDs.
@@ -936,7 +929,7 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
 
         txn.execute(sql, args)
 
-        result: Dict[str, _RoomReceipt] = {}
+        result: dict[str, _RoomReceipt] = {}
         for room_id, thread_id, stream_ordering in txn:
             room_receipt = result.setdefault(room_id, _RoomReceipt())
             if thread_id is None:
@@ -952,7 +945,7 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
         min_stream_ordering: int,
         max_stream_ordering: int,
         limit: int = 20,
-    ) -> List[HttpPushAction]:
+    ) -> list[HttpPushAction]:
         """Get a list of the most recent unread push actions for a given user,
         within the given stream ordering range. Called by the httppusher.
 
@@ -971,7 +964,7 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
 
         def get_push_actions_txn(
             txn: LoggingTransaction,
-        ) -> List[Tuple[str, str, str, int, str, bool]]:
+        ) -> list[tuple[str, str, str, int, str, bool]]:
             sql = """
                 SELECT ep.event_id, ep.room_id, ep.thread_id, ep.stream_ordering,
                     ep.actions, ep.highlight
@@ -984,7 +977,7 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
                 ORDER BY ep.stream_ordering ASC LIMIT ?
             """
             txn.execute(sql, (user_id, min_stream_ordering, max_stream_ordering, limit))
-            return cast(List[Tuple[str, str, str, int, str, bool]], txn.fetchall())
+            return cast(list[tuple[str, str, str, int, str, bool]], txn.fetchall())
 
         push_actions = await self.db_pool.runInteraction(
             "get_unread_push_actions_for_user_in_range_http", get_push_actions_txn
@@ -1040,7 +1033,7 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
         min_stream_ordering: int,
         max_stream_ordering: int,
         limit: int = 20,
-    ) -> List[EmailPushAction]:
+    ) -> list[EmailPushAction]:
         """Get a list of the most recent unread push actions for a given user,
         within the given stream ordering range. Called by the emailpusher
 
@@ -1059,7 +1052,7 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
 
         def get_push_actions_txn(
             txn: LoggingTransaction,
-        ) -> List[Tuple[str, str, str, int, str, bool, int]]:
+        ) -> list[tuple[str, str, str, int, str, bool, int]]:
             sql = """
                 SELECT ep.event_id, ep.room_id, ep.thread_id, ep.stream_ordering,
                     ep.actions, ep.highlight, e.received_ts
@@ -1073,7 +1066,7 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
                 ORDER BY ep.stream_ordering DESC LIMIT ?
             """
             txn.execute(sql, (user_id, min_stream_ordering, max_stream_ordering, limit))
-            return cast(List[Tuple[str, str, str, int, str, bool, int]], txn.fetchall())
+            return cast(list[tuple[str, str, str, int, str, bool, int]], txn.fetchall())
 
         push_actions = await self.db_pool.runInteraction(
             "get_unread_push_actions_for_user_in_range_email", get_push_actions_txn
@@ -1159,7 +1152,7 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
     async def add_push_actions_to_staging(
         self,
         event_id: str,
-        user_id_actions: Dict[str, Collection[Union[Mapping, str]]],
+        user_id_actions: dict[str, Collection[Mapping | str]],
         count_as_unread: bool,
         thread_id: str,
     ) -> None:
@@ -1178,8 +1171,8 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
         # This is a helper function for generating the necessary tuple that
         # can be used to insert into the `event_push_actions_staging` table.
         def _gen_entry(
-            user_id: str, actions: Collection[Union[Mapping, str]]
-        ) -> Tuple[str, str, str, int, int, int, str, int]:
+            user_id: str, actions: Collection[Mapping | str]
+        ) -> tuple[str, str, str, int, int, int, str, int]:
             is_highlight = 1 if _action_has_highlight(actions) else 0
             notif = 1 if "notify" in actions else 0
             return (
@@ -1190,7 +1183,7 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
                 is_highlight,  # highlight column
                 int(count_as_unread),  # unread column
                 thread_id,  # thread_id column
-                self._clock.time_msec(),  # inserted_ts column
+                self.clock.time_msec(),  # inserted_ts column
             )
 
         await self.db_pool.simple_insert_many(
@@ -1241,14 +1234,14 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
     def _find_stream_orderings_for_times_txn(self, txn: LoggingTransaction) -> None:
         logger.info("Searching for stream ordering 1 month ago")
         self.stream_ordering_month_ago = self._find_first_stream_ordering_after_ts_txn(
-            txn, self._clock.time_msec() - 30 * 24 * 60 * 60 * 1000
+            txn, self.clock.time_msec() - 30 * 24 * 60 * 60 * 1000
         )
         logger.info(
             "Found stream ordering 1 month ago: it's %d", self.stream_ordering_month_ago
         )
         logger.info("Searching for stream ordering 1 day ago")
         self.stream_ordering_day_ago = self._find_first_stream_ordering_after_ts_txn(
-            txn, self._clock.time_msec() - 24 * 60 * 60 * 1000
+            txn, self.clock.time_msec() - 24 * 60 * 60 * 1000
         )
         logger.info(
             "Found stream ordering 1 day ago: it's %d", self.stream_ordering_day_ago
@@ -1296,7 +1289,7 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
             The stream ordering
         """
         txn.execute("SELECT MAX(stream_ordering) FROM events")
-        max_stream_ordering = cast(Tuple[Optional[int]], txn.fetchone())[0]
+        max_stream_ordering = cast(tuple[int | None], txn.fetchone())[0]
 
         if max_stream_ordering is None:
             return 0
@@ -1354,8 +1347,8 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
 
     async def get_time_of_last_push_action_before(
         self, stream_ordering: int
-    ) -> Optional[int]:
-        def f(txn: LoggingTransaction) -> Optional[Tuple[int]]:
+    ) -> int | None:
+        def f(txn: LoggingTransaction) -> tuple[int] | None:
             sql = """
                 SELECT e.received_ts
                 FROM event_push_actions AS ep
@@ -1365,7 +1358,7 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
                 LIMIT 1
             """
             txn.execute(sql, (stream_ordering,))
-            return cast(Optional[Tuple[int]], txn.fetchone())
+            return cast(tuple[int] | None, txn.fetchone())
 
         result = await self.db_pool.runInteraction(
             "get_time_of_last_push_action_before", f
@@ -1457,7 +1450,7 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
                 limit,
             ),
         )
-        rows = cast(List[Tuple[int, str, str, Optional[str], int]], txn.fetchall())
+        rows = cast(list[tuple[int, str, str, str | None, int]], txn.fetchall())
 
         # For each new read receipt we delete push actions from before it and
         # recalculate the summary.
@@ -1469,7 +1462,7 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
                 continue
 
             thread_clause = ""
-            thread_args: Tuple = ()
+            thread_args: tuple = ()
             if thread_id is not None:
                 thread_clause = "AND thread_id = ?"
                 thread_args = (thread_id,)
@@ -1654,7 +1647,7 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
         # object because we might not have the same amount of rows in each of them. To do
         # this, we use a dict indexed on the user ID and room ID to make it easier to
         # populate.
-        summaries: Dict[Tuple[str, str, str], _EventPushSummary] = {}
+        summaries: dict[tuple[str, str, str], _EventPushSummary] = {}
         for row in txn:
             summaries[(row[0], row[1], row[2])] = _EventPushSummary(
                 unread_count=row[3],
@@ -1787,7 +1780,7 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
 
         # We delete anything more than an hour old, on the assumption that we'll
         # never take more than an hour to persist an event.
-        delete_before_ts = self._clock.time_msec() - 60 * 60 * 1000
+        delete_before_ts = self.clock.time_msec() - 60 * 60 * 1000
 
         if self._started_ts > delete_before_ts:
             # We need to wait for at least an hour before we started deleting,
@@ -1824,18 +1817,18 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
                 return
 
             # We sleep to ensure that we don't overwhelm the DB.
-            await self._clock.sleep(1.0)
+            await self.clock.sleep(1.0)
 
     async def get_push_actions_for_user(
         self,
         user_id: str,
-        before: Optional[int] = None,
+        before: int | None = None,
         limit: int = 50,
         only_highlight: bool = False,
-    ) -> List[UserPushAction]:
+    ) -> list[UserPushAction]:
         def f(
             txn: LoggingTransaction,
-        ) -> List[Tuple[str, str, int, int, str, bool, str, int]]:
+        ) -> list[tuple[str, str, int, int, str, bool, str, int]]:
             before_clause = ""
             if before:
                 before_clause = "AND epa.stream_ordering < ?"
@@ -1863,7 +1856,7 @@ class EventPushActionsWorkerStore(ReceiptsWorkerStore, StreamWorkerStore, SQLBas
             """ % (before_clause,)
             txn.execute(sql, args)
             return cast(
-                List[Tuple[str, str, int, int, str, bool, str, int]], txn.fetchall()
+                list[tuple[str, str, int, int, str, bool, str, int]], txn.fetchall()
             )
 
         push_actions = await self.db_pool.runInteraction("get_push_actions_for_user", f)
@@ -1918,7 +1911,7 @@ class EventPushActionsStore(EventPushActionsWorkerStore):
         )
 
 
-def _action_has_highlight(actions: Collection[Union[Mapping, str]]) -> bool:
+def _action_has_highlight(actions: Collection[Mapping | str]) -> bool:
     for action in actions:
         if not isinstance(action, dict):
             continue
diff --git a/synapse/storage/databases/main/events.py b/synapse/storage/databases/main/events.py
index b6037468b3..59112e647c 100644
--- a/synapse/storage/databases/main/events.py
+++ b/synapse/storage/databases/main/events.py
@@ -27,14 +27,9 @@ from typing import (
     TYPE_CHECKING,
     Any,
     Collection,
-    Dict,
     Generator,
     Iterable,
-    List,
-    Optional,
     Sequence,
-    Set,
-    Tuple,
     TypedDict,
     cast,
 )
@@ -129,7 +124,7 @@ class DeltaState:
             should e.g. be removed from `current_state_events` table.
     """
 
-    to_delete: List[Tuple[str, str]]
+    to_delete: list[tuple[str, str]]
     to_insert: StateMap[str]
     no_longer_in_room: bool = False
 
@@ -145,10 +140,10 @@ class SlidingSyncStateInsertValues(TypedDict, total=False):
     `sliding_sync_membership_snapshots` database tables.
     """
 
-    room_type: Optional[str]
-    is_encrypted: Optional[bool]
-    room_name: Optional[str]
-    tombstone_successor_room_id: Optional[str]
+    room_type: str | None
+    is_encrypted: bool | None
+    room_name: str | None
+    tombstone_successor_room_id: str | None
 
 
 class SlidingSyncMembershipSnapshotSharedInsertValues(
@@ -159,7 +154,7 @@ class SlidingSyncMembershipSnapshotSharedInsertValues(
     multiple memberships
     """
 
-    has_known_state: Optional[bool]
+    has_known_state: bool | None
 
 
 @attr.s(slots=True, auto_attribs=True)
@@ -197,7 +192,7 @@ class SlidingSyncTableChanges:
     # foreground update for
     # `sliding_sync_joined_rooms`/`sliding_sync_membership_snapshots` (tracked by
     # https://github.com/element-hq/synapse/issues/17623)
-    joined_room_bump_stamp_to_fully_insert: Optional[int]
+    joined_room_bump_stamp_to_fully_insert: int | None
     # Values to upsert into `sliding_sync_joined_rooms`
     joined_room_updates: SlidingSyncStateInsertValues
 
@@ -207,9 +202,9 @@ class SlidingSyncTableChanges:
         SlidingSyncMembershipSnapshotSharedInsertValues
     )
     # List of membership to insert into `sliding_sync_membership_snapshots`
-    to_insert_membership_snapshots: List[SlidingSyncMembershipInfo]
+    to_insert_membership_snapshots: list[SlidingSyncMembershipInfo]
     # List of user_id to delete from `sliding_sync_membership_snapshots`
-    to_delete_membership_snapshots: List[str]
+    to_delete_membership_snapshots: list[str]
 
 
 @attr.s(slots=True, auto_attribs=True)
@@ -226,7 +221,7 @@ class NewEventChainLinks:
     chain_id: int
     sequence_number: int
 
-    links: List[Tuple[int, int]] = attr.Factory(list)
+    links: list[tuple[int, int]] = attr.Factory(list)
 
 
 class PersistEventsStore:
@@ -274,11 +269,11 @@ class PersistEventsStore:
     async def _persist_events_and_state_updates(
         self,
         room_id: str,
-        events_and_contexts: List[EventPersistencePair],
+        events_and_contexts: list[EventPersistencePair],
         *,
-        state_delta_for_room: Optional[DeltaState],
-        new_forward_extremities: Optional[Set[str]],
-        new_event_links: Dict[str, NewEventChainLinks],
+        state_delta_for_room: DeltaState | None,
+        new_forward_extremities: set[str] | None,
+        new_event_links: dict[str, NewEventChainLinks],
         use_negative_stream_ordering: bool = False,
         inhibit_local_membership_updates: bool = False,
     ) -> None:
@@ -585,21 +580,21 @@ class PersistEventsStore:
         ]
 
         membership_snapshot_shared_insert_values: SlidingSyncMembershipSnapshotSharedInsertValues = {}
-        membership_infos_to_insert_membership_snapshots: List[
+        membership_infos_to_insert_membership_snapshots: list[
             SlidingSyncMembershipInfo
         ] = []
         if to_insert:
-            membership_event_id_to_user_id_map: Dict[str, str] = {}
+            membership_event_id_to_user_id_map: dict[str, str] = {}
             for state_key, event_id in to_insert.items():
                 if state_key[0] == EventTypes.Member and self.is_mine_id(state_key[1]):
                     membership_event_id_to_user_id_map[event_id] = state_key[1]
 
-            membership_event_map: Dict[str, EventBase] = {}
+            membership_event_map: dict[str, EventBase] = {}
             # In normal event persist scenarios, we should be able to find the
             # membership events in the `events_and_contexts` given to us but it's
             # possible a state reset happened which added us to the room without a
             # corresponding new membership event (reset back to a previous membership).
-            missing_membership_event_ids: Set[str] = set()
+            missing_membership_event_ids: set[str] = set()
             for membership_event_id in membership_event_id_to_user_id_map.keys():
                 membership_event = event_map.get(membership_event_id)
                 if membership_event:
@@ -668,7 +663,7 @@ class PersistEventsStore:
                 # these state events in `events_and_contexts` since we don't generally
                 # batch up local membership changes with other events, but it can
                 # happen.
-                missing_state_event_ids: Set[str] = set()
+                missing_state_event_ids: set[str] = set()
                 for state_key, event_id in current_state_ids_map.items():
                     event = event_map.get(event_id)
                     if event:
@@ -721,7 +716,7 @@ class PersistEventsStore:
         # `_update_sliding_sync_tables_with_new_persisted_events_txn()`)
         #
         joined_room_updates: SlidingSyncStateInsertValues = {}
-        bump_stamp_to_fully_insert: Optional[int] = None
+        bump_stamp_to_fully_insert: int | None = None
         if not delta_state.no_longer_in_room:
             current_state_ids_map = {}
 
@@ -780,7 +775,7 @@ class PersistEventsStore:
             # events in the `events_and_contexts` given to us but it's possible a state
             # reset happened which that reset back to a previous state.
             current_state_map = {}
-            missing_event_ids: Set[str] = set()
+            missing_event_ids: set[str] = set()
             for state_key, event_id in current_state_ids_map.items():
                 event = event_map.get(event_id)
                 if event:
@@ -826,7 +821,7 @@ class PersistEventsStore:
 
     async def calculate_chain_cover_index_for_events(
         self, room_id: str, events: Collection[EventBase]
-    ) -> Dict[str, NewEventChainLinks]:
+    ) -> dict[str, NewEventChainLinks]:
         # Filter to state events, and ensure there are no duplicates.
         state_events = []
         seen_events = set()
@@ -849,7 +844,7 @@ class PersistEventsStore:
 
     def calculate_chain_cover_index_for_events_txn(
         self, txn: LoggingTransaction, room_id: str, state_events: Collection[EventBase]
-    ) -> Dict[str, NewEventChainLinks]:
+    ) -> dict[str, NewEventChainLinks]:
         # We now calculate chain ID/sequence numbers for any state events we're
         # persisting. We ignore out of band memberships as we're not in the room
         # and won't have their auth chain (we'll fix it up later if we join the
@@ -905,7 +900,7 @@ class PersistEventsStore:
             event_to_auth_chain,
         )
 
-    async def _get_events_which_are_prevs(self, event_ids: Iterable[str]) -> List[str]:
+    async def _get_events_which_are_prevs(self, event_ids: Iterable[str]) -> list[str]:
         """Filter the supplied list of event_ids to get those which are prev_events of
         existing (non-outlier/rejected) events.
 
@@ -915,7 +910,7 @@ class PersistEventsStore:
         Returns:
             Filtered event ids
         """
-        results: List[str] = []
+        results: list[str] = []
 
         def _get_events_which_are_prevs_txn(
             txn: LoggingTransaction, batch: Collection[str]
@@ -946,7 +941,7 @@ class PersistEventsStore:
 
         return results
 
-    async def _get_prevs_before_rejected(self, event_ids: Iterable[str]) -> Set[str]:
+    async def _get_prevs_before_rejected(self, event_ids: Iterable[str]) -> set[str]:
         """Get soft-failed ancestors to remove from the extremities.
 
         Given a set of events, find all those that have been soft-failed or
@@ -967,7 +962,7 @@ class PersistEventsStore:
 
         # The set of event_ids to return. This includes all soft-failed events
         # and their prev events.
-        existing_prevs: Set[str] = set()
+        existing_prevs: set[str] = set()
 
         def _get_prevs_before_rejected_txn(
             txn: LoggingTransaction, batch: Collection[str]
@@ -1016,12 +1011,12 @@ class PersistEventsStore:
         txn: LoggingTransaction,
         *,
         room_id: str,
-        events_and_contexts: List[EventPersistencePair],
+        events_and_contexts: list[EventPersistencePair],
         inhibit_local_membership_updates: bool,
-        state_delta_for_room: Optional[DeltaState],
-        new_forward_extremities: Optional[Set[str]],
-        new_event_links: Dict[str, NewEventChainLinks],
-        sliding_sync_table_changes: Optional[SlidingSyncTableChanges],
+        state_delta_for_room: DeltaState | None,
+        new_forward_extremities: set[str] | None,
+        new_event_links: dict[str, NewEventChainLinks],
+        sliding_sync_table_changes: SlidingSyncTableChanges | None,
     ) -> None:
         """Insert some number of room events into the necessary database tables.
 
@@ -1178,8 +1173,8 @@ class PersistEventsStore:
     def _persist_event_auth_chain_txn(
         self,
         txn: LoggingTransaction,
-        events: List[EventBase],
-        new_event_links: Dict[str, NewEventChainLinks],
+        events: list[EventBase],
+        new_event_links: dict[str, NewEventChainLinks],
     ) -> None:
         if new_event_links:
             self._persist_chain_cover_index(txn, self.db_pool, new_event_links)
@@ -1212,9 +1207,9 @@ class PersistEventsStore:
         txn: LoggingTransaction,
         db_pool: DatabasePool,
         event_chain_id_gen: SequenceGenerator,
-        event_to_room_id: Dict[str, str],
-        event_to_types: Dict[str, Tuple[str, str]],
-        event_to_auth_chain: Dict[str, StrCollection],
+        event_to_room_id: dict[str, str],
+        event_to_types: dict[str, tuple[str, str]],
+        event_to_auth_chain: dict[str, StrCollection],
     ) -> None:
         """Calculate and persist the chain cover index for the given events.
 
@@ -1241,10 +1236,10 @@ class PersistEventsStore:
         txn: LoggingTransaction,
         db_pool: DatabasePool,
         event_chain_id_gen: SequenceGenerator,
-        event_to_room_id: Dict[str, str],
-        event_to_types: Dict[str, Tuple[str, str]],
-        event_to_auth_chain: Dict[str, StrCollection],
-    ) -> Dict[str, NewEventChainLinks]:
+        event_to_room_id: dict[str, str],
+        event_to_types: dict[str, tuple[str, str]],
+        event_to_auth_chain: dict[str, StrCollection],
+    ) -> dict[str, NewEventChainLinks]:
         """Calculate the chain cover index for the given events.
 
         Args:
@@ -1259,7 +1254,7 @@ class PersistEventsStore:
         """
 
         # Map from event ID to chain ID/sequence number.
-        chain_map: Dict[str, Tuple[int, int]] = {}
+        chain_map: dict[str, tuple[int, int]] = {}
 
         # Set of event IDs to calculate chain ID/seq numbers for.
         events_to_calc_chain_id_for = set(event_to_room_id)
@@ -1268,7 +1263,7 @@ class PersistEventsStore:
         # we're looking at. These should just be out of band memberships, where
         # we didn't have the auth chain when we first persisted.
         auth_chain_to_calc_rows = cast(
-            List[Tuple[str, str, str]],
+            list[tuple[str, str, str]],
             db_pool.simple_select_many_txn(
                 txn,
                 table="event_auth_chain_to_calculate",
@@ -1490,7 +1485,7 @@ class PersistEventsStore:
         cls,
         txn: LoggingTransaction,
         db_pool: DatabasePool,
-        new_event_links: Dict[str, NewEventChainLinks],
+        new_event_links: dict[str, NewEventChainLinks],
     ) -> None:
         db_pool.simple_insert_many_txn(
             txn,
@@ -1536,12 +1531,12 @@ class PersistEventsStore:
         txn: LoggingTransaction,
         db_pool: DatabasePool,
         event_chain_id_gen: SequenceGenerator,
-        event_to_room_id: Dict[str, str],
-        event_to_types: Dict[str, Tuple[str, str]],
-        event_to_auth_chain: Dict[str, StrCollection],
-        events_to_calc_chain_id_for: Set[str],
-        chain_map: Dict[str, Tuple[int, int]],
-    ) -> Dict[str, Tuple[int, int]]:
+        event_to_room_id: dict[str, str],
+        event_to_types: dict[str, tuple[str, str]],
+        event_to_auth_chain: dict[str, StrCollection],
+        events_to_calc_chain_id_for: set[str],
+        chain_map: dict[str, tuple[int, int]],
+    ) -> dict[str, tuple[int, int]]:
         """Allocates, but does not persist, chain ID/sequence numbers for the
         events in `events_to_calc_chain_id_for`. (c.f. _add_chain_cover_index
         for info on args)
@@ -1573,8 +1568,8 @@ class PersistEventsStore:
         #      new chain if the sequence number has already been allocated.
         #
 
-        existing_chains: Set[int] = set()
-        tree: List[Tuple[str, Optional[str]]] = []
+        existing_chains: set[int] = set()
+        tree: list[tuple[str, str | None]] = []
 
         # We need to do this in a topologically sorted order as we want to
         # generate chain IDs/sequence numbers of an event's auth events before
@@ -1604,7 +1599,7 @@ class PersistEventsStore:
         )
         txn.execute(sql % (clause,), args)
 
-        chain_to_max_seq_no: Dict[Any, int] = {row[0]: row[1] for row in txn}
+        chain_to_max_seq_no: dict[Any, int] = {row[0]: row[1] for row in txn}
 
         # Allocate the new events chain ID/sequence numbers.
         #
@@ -1614,8 +1609,8 @@ class PersistEventsStore:
         # number of new chain IDs in one call, replacing all temporary
         # objects with real allocated chain IDs.
 
-        unallocated_chain_ids: Set[object] = set()
-        new_chain_tuples: Dict[str, Tuple[Any, int]] = {}
+        unallocated_chain_ids: set[object] = set()
+        new_chain_tuples: dict[str, tuple[Any, int]] = {}
         for event_id, auth_event_id in tree:
             # If we reference an auth_event_id we fetch the allocated chain ID,
             # either from the existing `chain_map` or the newly generated
@@ -1626,7 +1621,7 @@ class PersistEventsStore:
                 if not existing_chain_id:
                     existing_chain_id = chain_map[auth_event_id]
 
-            new_chain_tuple: Optional[Tuple[Any, int]] = None
+            new_chain_tuple: tuple[Any, int] | None = None
             if existing_chain_id:
                 # We found a chain ID/sequence number candidate, check its
                 # not already taken.
@@ -1653,7 +1648,7 @@ class PersistEventsStore:
         )
 
         # Map from potentially temporary chain ID to real chain ID
-        chain_id_to_allocated_map: Dict[Any, int] = dict(
+        chain_id_to_allocated_map: dict[Any, int] = dict(
             zip(unallocated_chain_ids, newly_allocated_chain_ids)
         )
         chain_id_to_allocated_map.update((c, c) for c in existing_chains)
@@ -1666,12 +1661,12 @@ class PersistEventsStore:
     def _persist_transaction_ids_txn(
         self,
         txn: LoggingTransaction,
-        events_and_contexts: List[EventPersistencePair],
+        events_and_contexts: list[EventPersistencePair],
     ) -> None:
         """Persist the mapping from transaction IDs to event IDs (if defined)."""
 
         inserted_ts = self._clock.time_msec()
-        to_insert_device_id: List[Tuple[str, str, str, str, str, int]] = []
+        to_insert_device_id: list[tuple[str, str, str, str, str, int]] = []
         for event, _ in events_and_contexts:
             txn_id = getattr(event.internal_metadata, "txn_id", None)
             device_id = getattr(event.internal_metadata, "device_id", None)
@@ -1899,7 +1894,7 @@ class PersistEventsStore:
                     sliding_sync_table_changes.joined_room_updates.values()
                 )
 
-                args: List[Any] = [
+                args: list[Any] = [
                     room_id,
                     room_id,
                     sliding_sync_table_changes.joined_room_bump_stamp_to_fully_insert,
@@ -2316,7 +2311,7 @@ class PersistEventsStore:
         self,
         txn: LoggingTransaction,
         room_id: str,
-        events_and_contexts: List[EventPersistencePair],
+        events_and_contexts: list[EventPersistencePair],
     ) -> None:
         """
         Update the latest `event_stream_ordering`/`bump_stamp` columns in the
@@ -2427,7 +2422,7 @@ class PersistEventsStore:
         self,
         txn: LoggingTransaction,
         room_id: str,
-        new_forward_extremities: Set[str],
+        new_forward_extremities: set[str],
         max_stream_order: int,
     ) -> None:
         self.db_pool.simple_delete_txn(
@@ -2456,8 +2451,8 @@ class PersistEventsStore:
 
     @classmethod
     def _filter_events_and_contexts_for_duplicates(
-        cls, events_and_contexts: List[EventPersistencePair]
-    ) -> List[EventPersistencePair]:
+        cls, events_and_contexts: list[EventPersistencePair]
+    ) -> list[EventPersistencePair]:
         """Ensure that we don't have the same event twice.
 
         Pick the earliest non-outlier if there is one, else the earliest one.
@@ -2486,7 +2481,7 @@ class PersistEventsStore:
         self,
         txn: LoggingTransaction,
         room_id: str,
-        events_and_contexts: List[EventPersistencePair],
+        events_and_contexts: list[EventPersistencePair],
     ) -> None:
         """Update min_depth for each room
 
@@ -2495,7 +2490,7 @@ class PersistEventsStore:
             room_id: The room ID
             events_and_contexts: events we are persisting
         """
-        stream_ordering: Optional[int] = None
+        stream_ordering: int | None = None
         depth_update = 0
         for event, context in events_and_contexts:
             # Don't update the stream ordering for backfilled events because
@@ -2528,8 +2523,8 @@ class PersistEventsStore:
     def _update_outliers_txn(
         self,
         txn: LoggingTransaction,
-        events_and_contexts: List[EventPersistencePair],
-    ) -> List[EventPersistencePair]:
+        events_and_contexts: list[EventPersistencePair],
+    ) -> list[EventPersistencePair]:
         """Update any outliers with new event info.
 
         This turns outliers into ex-outliers (unless the new event was rejected), and
@@ -2547,7 +2542,7 @@ class PersistEventsStore:
                 a room that has been un-partial stated.
         """
         rows = cast(
-            List[Tuple[str, bool]],
+            list[tuple[str, bool]],
             self.db_pool.simple_select_many_txn(
                 txn,
                 "events",
@@ -2740,8 +2735,8 @@ class PersistEventsStore:
     def _store_rejected_events_txn(
         self,
         txn: LoggingTransaction,
-        events_and_contexts: List[EventPersistencePair],
-    ) -> List[EventPersistencePair]:
+        events_and_contexts: list[EventPersistencePair],
+    ) -> list[EventPersistencePair]:
         """Add rows to the 'rejections' table for received events which were
         rejected
 
@@ -2768,8 +2763,8 @@ class PersistEventsStore:
         self,
         txn: LoggingTransaction,
         *,
-        events_and_contexts: List[EventPersistencePair],
-        all_events_and_contexts: List[EventPersistencePair],
+        events_and_contexts: list[EventPersistencePair],
+        all_events_and_contexts: list[EventPersistencePair],
         inhibit_local_membership_updates: bool = False,
     ) -> None:
         """Update all the miscellaneous tables for new events
@@ -2863,9 +2858,9 @@ class PersistEventsStore:
     def _add_to_cache(
         self,
         txn: LoggingTransaction,
-        events_and_contexts: List[EventPersistencePair],
+        events_and_contexts: list[EventPersistencePair],
     ) -> None:
-        to_prefill: List[EventCacheEntry] = []
+        to_prefill: list[EventCacheEntry] = []
 
         ev_map = {e.event_id: e for e, _ in events_and_contexts}
         if not ev_map:
@@ -2925,7 +2920,7 @@ class PersistEventsStore:
         self,
         txn: LoggingTransaction,
         event_id: str,
-        labels: List[str],
+        labels: list[str],
         room_id: str,
         topological_ordering: int,
     ) -> None:
@@ -2967,7 +2962,7 @@ class PersistEventsStore:
     def _store_room_members_txn(
         self,
         txn: LoggingTransaction,
-        events: List[EventBase],
+        events: list[EventBase],
         *,
         inhibit_local_membership_updates: bool = False,
     ) -> None:
@@ -3336,8 +3331,8 @@ class PersistEventsStore:
     def _set_push_actions_for_event_and_users_txn(
         self,
         txn: LoggingTransaction,
-        events_and_contexts: List[EventPersistencePair],
-        all_events_and_contexts: List[EventPersistencePair],
+        events_and_contexts: list[EventPersistencePair],
+        all_events_and_contexts: list[EventPersistencePair],
     ) -> None:
         """Handles moving push actions from staging table to main
         event_push_actions table for all events in `events_and_contexts`.
@@ -3517,7 +3512,7 @@ class PersistEventsStore:
         )
 
     def _handle_mult_prev_events(
-        self, txn: LoggingTransaction, events: List[EventBase]
+        self, txn: LoggingTransaction, events: list[EventBase]
     ) -> None:
         """
         For the given event, update the event edges table and forward and
@@ -3535,7 +3530,7 @@ class PersistEventsStore:
         self._update_backward_extremeties(txn, events)
 
     def _update_backward_extremeties(
-        self, txn: LoggingTransaction, events: List[EventBase]
+        self, txn: LoggingTransaction, events: list[EventBase]
     ) -> None:
         """Updates the event_backward_extremities tables based on the new/updated
         events being persisted.
@@ -3637,16 +3632,16 @@ class _LinkMap:
 
     # Stores the set of links as nested maps: source chain ID -> target chain ID
     # -> source sequence number -> target sequence number.
-    maps: Dict[int, Dict[int, Dict[int, int]]] = attr.Factory(dict)
+    maps: dict[int, dict[int, dict[int, int]]] = attr.Factory(dict)
 
     # Stores the links that have been added (with new set to true), as tuples of
     # `(source chain ID, source sequence no, target chain ID, target sequence no.)`
-    additions: Set[Tuple[int, int, int, int]] = attr.Factory(set)
+    additions: set[tuple[int, int, int, int]] = attr.Factory(set)
 
     def add_link(
         self,
-        src_tuple: Tuple[int, int],
-        target_tuple: Tuple[int, int],
+        src_tuple: tuple[int, int],
+        target_tuple: tuple[int, int],
         new: bool = True,
     ) -> bool:
         """Add a new link between two chains, ensuring no redundant links are added.
@@ -3701,7 +3696,7 @@ class _LinkMap:
         current_links[src_seq] = target_seq
         return True
 
-    def get_additions(self) -> Generator[Tuple[int, int, int, int], None, None]:
+    def get_additions(self) -> Generator[tuple[int, int, int, int], None, None]:
         """Gets any newly added links.
 
         Yields:
@@ -3715,8 +3710,8 @@ class _LinkMap:
 
     def exists_path_from(
         self,
-        src_tuple: Tuple[int, int],
-        target_tuple: Tuple[int, int],
+        src_tuple: tuple[int, int],
+        target_tuple: tuple[int, int],
     ) -> bool:
         """Checks if there is a path between the source chain ID/sequence and
         target chain ID/sequence.
@@ -3728,7 +3723,7 @@ class _LinkMap:
             return target_seq <= src_seq
 
         # We have to graph traverse the links to check for indirect paths.
-        visited_chains: Dict[int, int] = collections.Counter()
+        visited_chains: dict[int, int] = collections.Counter()
         search = [(src_chain, src_seq)]
         while search:
             chain, seq = search.pop()
diff --git a/synapse/storage/databases/main/events_bg_updates.py b/synapse/storage/databases/main/events_bg_updates.py
index 0a0102ee64..f8300e016b 100644
--- a/synapse/storage/databases/main/events_bg_updates.py
+++ b/synapse/storage/databases/main/events_bg_updates.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Dict, List, Optional, Set, Tuple, cast
+from typing import TYPE_CHECKING, cast
 
 import attr
 
@@ -97,7 +97,7 @@ class _CalculateChainCover:
     # Map from room_id to last depth/stream processed for each room that we have
     # processed all events for (i.e. the rooms we can flip the
     # `has_auth_chain_index` for)
-    finished_room_map: Dict[str, Tuple[int, int]]
+    finished_room_map: dict[str, tuple[int, int]]
 
 
 @attr.s(slots=True, frozen=True, auto_attribs=True)
@@ -109,7 +109,7 @@ class _JoinedRoomStreamOrderingUpdate:
     # The most recent event stream_ordering for the room
     most_recent_event_stream_ordering: int
     # The most recent event `bump_stamp` for the room
-    most_recent_bump_stamp: Optional[int]
+    most_recent_bump_stamp: int | None
 
 
 class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseStore):
@@ -451,7 +451,7 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
             chunks = [event_ids[i : i + 100] for i in range(0, len(event_ids), 100)]
             for chunk in chunks:
                 ev_rows = cast(
-                    List[Tuple[str, str]],
+                    list[tuple[str, str]],
                     self.db_pool.simple_select_many_txn(
                         txn,
                         table="event_json",
@@ -527,8 +527,8 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
             # The set of extremity event IDs that we're checking this round
             original_set = set()
 
-            # A dict[str, Set[str]] of event ID to their prev events.
-            graph: Dict[str, Set[str]] = {}
+            # A dict[str, set[str]] of event ID to their prev events.
+            graph: dict[str, set[str]] = {}
 
             # The set of descendants of the original set that are not rejected
             # nor soft-failed. Ancestors of these events should be removed
@@ -647,7 +647,7 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
             if deleted:
                 # We now need to invalidate the caches of these rooms
                 rows = cast(
-                    List[Tuple[str]],
+                    list[tuple[str]],
                     self.db_pool.simple_select_many_txn(
                         txn,
                         table="events",
@@ -730,7 +730,7 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
                 WHERE ? <= event_id AND event_id <= ?
             """
 
-            txn.execute(sql, (self._clock.time_msec(), last_event_id, upper_event_id))
+            txn.execute(sql, (self.clock.time_msec(), last_event_id, upper_event_id))
 
             self.db_pool.updates._background_update_progress_txn(
                 txn, "redactions_received_ts", {"last_event_id": upper_event_id}
@@ -851,7 +851,7 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
 
         def get_rejected_events(
             txn: Cursor,
-        ) -> List[Tuple[str, str, JsonDict, bool, bool]]:
+        ) -> list[tuple[str, str, JsonDict, bool, bool]]:
             # Fetch rejected event json, their room version and whether we have
             # inserted them into the state_events or auth_events tables.
             #
@@ -883,7 +883,7 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
             )
 
             return cast(
-                List[Tuple[str, str, JsonDict, bool, bool]],
+                list[tuple[str, str, JsonDict, bool, bool]],
                 [(row[0], row[1], db_to_json(row[2]), row[3], row[4]) for row in txn],
             )
 
@@ -1038,7 +1038,7 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
         last_room_id: str,
         last_depth: int,
         last_stream: int,
-        batch_size: Optional[int],
+        batch_size: int | None,
         single_room: bool,
     ) -> _CalculateChainCover:
         """Calculate the chain cover for `batch_size` events, ordered by
@@ -1126,7 +1126,7 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
 
         # We also need to fetch the auth events for them.
         auth_events = cast(
-            List[Tuple[str, str]],
+            list[tuple[str, str]],
             self.db_pool.simple_select_many_txn(
                 txn,
                 table="event_auth",
@@ -1137,7 +1137,7 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
             ),
         )
 
-        event_to_auth_chain: Dict[str, List[str]] = {}
+        event_to_auth_chain: dict[str, list[str]] = {}
         for event_id, auth_id in auth_events:
             event_to_auth_chain.setdefault(event_id, []).append(auth_id)
 
@@ -1151,7 +1151,7 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
             self.event_chain_id_gen,
             event_to_room_id,
             event_to_types,
-            cast(Dict[str, StrCollection], event_to_auth_chain),
+            cast(dict[str, StrCollection], event_to_auth_chain),
         )
 
         return _CalculateChainCover(
@@ -1256,7 +1256,7 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
 
             results = list(txn)
             # (event_id, parent_id, rel_type) for each relation
-            relations_to_insert: List[Tuple[str, str, str, str]] = []
+            relations_to_insert: list[tuple[str, str, str, str]] = []
             for event_id, event_json_raw in results:
                 try:
                     event_json = db_to_json(event_json_raw)
@@ -1636,7 +1636,7 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
         # We don't need to fetch any progress state because we just grab the next N
         # events in `sliding_sync_joined_rooms_to_recalculate`
 
-        def _get_rooms_to_update_txn(txn: LoggingTransaction) -> List[Tuple[str]]:
+        def _get_rooms_to_update_txn(txn: LoggingTransaction) -> list[tuple[str]]:
             """
             Returns:
                 A list of room ID's to update along with the progress value
@@ -1658,7 +1658,7 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
                 (batch_size,),
             )
 
-            rooms_to_update_rows = cast(List[Tuple[str]], txn.fetchall())
+            rooms_to_update_rows = cast(list[tuple[str]], txn.fetchall())
 
             return rooms_to_update_rows
 
@@ -1674,9 +1674,9 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
             return 0
 
         # Map from room_id to insert/update state values in the `sliding_sync_joined_rooms` table.
-        joined_room_updates: Dict[str, SlidingSyncStateInsertValues] = {}
+        joined_room_updates: dict[str, SlidingSyncStateInsertValues] = {}
         # Map from room_id to stream_ordering/bump_stamp, etc values
-        joined_room_stream_ordering_updates: Dict[
+        joined_room_stream_ordering_updates: dict[
             str, _JoinedRoomStreamOrderingUpdate
         ] = {}
         # As long as we get this value before we fetch the current state, we can use it
@@ -1886,17 +1886,17 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
 
         def _find_memberships_to_update_txn(
             txn: LoggingTransaction,
-        ) -> List[
-            Tuple[
+        ) -> list[
+            tuple[
                 str,
-                Optional[str],
-                Optional[str],
+                str | None,
+                str | None,
                 str,
                 str,
                 str,
                 str,
                 int,
-                Optional[str],
+                str | None,
                 bool,
             ]
         ]:
@@ -1979,17 +1979,17 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
                 raise Exception("last_event_stream_ordering should not be None")
 
             memberships_to_update_rows = cast(
-                List[
-                    Tuple[
+                list[
+                    tuple[
                         str,
-                        Optional[str],
-                        Optional[str],
+                        str | None,
+                        str | None,
                         str,
                         str,
                         str,
                         str,
                         int,
-                        Optional[str],
+                        str | None,
                         bool,
                     ]
                 ],
@@ -2023,7 +2023,7 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
 
         def _find_previous_invite_or_knock_membership_txn(
             txn: LoggingTransaction, room_id: str, user_id: str, event_id: str
-        ) -> Optional[Tuple[str, str]]:
+        ) -> tuple[str, str] | None:
             # Find the previous invite/knock event before the leave event
             #
             # Here are some notes on how we landed on this query:
@@ -2085,11 +2085,11 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
             return event_id, membership
 
         # Map from (room_id, user_id) to ...
-        to_insert_membership_snapshots: Dict[
-            Tuple[str, str], SlidingSyncMembershipSnapshotSharedInsertValues
+        to_insert_membership_snapshots: dict[
+            tuple[str, str], SlidingSyncMembershipSnapshotSharedInsertValues
         ] = {}
-        to_insert_membership_infos: Dict[
-            Tuple[str, str], SlidingSyncMembershipInfoWithEventPos
+        to_insert_membership_infos: dict[
+            tuple[str, str], SlidingSyncMembershipInfoWithEventPos
         ] = {}
         for (
             room_id,
@@ -2510,7 +2510,7 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
             )
 
             memberships_to_update_rows = cast(
-                List[Tuple[str, str, str, int, int]],
+                list[tuple[str, str, str, int, int]],
                 txn.fetchall(),
             )
             if not memberships_to_update_rows:
@@ -2519,9 +2519,9 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
             # Assemble the values to update
             #
             # (room_id, user_id)
-            key_values: List[Tuple[str, str]] = []
+            key_values: list[tuple[str, str]] = []
             # (forgotten,)
-            value_values: List[Tuple[int]] = []
+            value_values: list[tuple[int]] = []
             for (
                 room_id,
                 user_id,
@@ -2585,7 +2585,7 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
 
         room_id_bound = progress.get("room_id", "")
 
-        def redo_max_depth_bg_update_txn(txn: LoggingTransaction) -> Tuple[bool, int]:
+        def redo_max_depth_bg_update_txn(txn: LoggingTransaction) -> tuple[bool, int]:
             txn.execute(
                 """
                 SELECT room_id, room_version FROM rooms
@@ -2597,8 +2597,8 @@ class EventsBackgroundUpdatesStore(StreamWorkerStore, StateDeltasStore, SQLBaseS
             )
 
             # Find the next room ID to process, with a relevant room version.
-            room_ids: List[str] = []
-            max_room_id: Optional[str] = None
+            room_ids: list[str] = []
+            max_room_id: str | None = None
             for room_id, room_version_str in txn:
                 max_room_id = room_id
 
@@ -2704,7 +2704,7 @@ def _resolve_stale_data_in_sliding_sync_joined_rooms_table(
 
     # If we have nothing written to the `sliding_sync_joined_rooms` table, there is
     # nothing to clean up
-    row = cast(Optional[Tuple[int]], txn.fetchone())
+    row = cast(tuple[int] | None, txn.fetchone())
     max_stream_ordering_sliding_sync_joined_rooms_table = None
     depends_on = None
     if row is not None:
@@ -2830,7 +2830,7 @@ def _resolve_stale_data_in_sliding_sync_membership_snapshots_table(
 
     # If we have nothing written to the `sliding_sync_membership_snapshots` table,
     # there is nothing to clean up
-    row = cast(Optional[Tuple[int]], txn.fetchone())
+    row = cast(tuple[int] | None, txn.fetchone())
     max_stream_ordering_sliding_sync_membership_snapshots_table = None
     if row is not None:
         (max_stream_ordering_sliding_sync_membership_snapshots_table,) = row
diff --git a/synapse/storage/databases/main/events_forward_extremities.py b/synapse/storage/databases/main/events_forward_extremities.py
index bd763885d7..9908244dbf 100644
--- a/synapse/storage/databases/main/events_forward_extremities.py
+++ b/synapse/storage/databases/main/events_forward_extremities.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import List, Optional, Tuple, cast
+from typing import cast
 
 from synapse.api.errors import SynapseError
 from synapse.storage.database import LoggingTransaction
@@ -98,7 +98,7 @@ class EventForwardExtremitiesStore(
 
     async def get_forward_extremities_for_room(
         self, room_id: str
-    ) -> List[Tuple[str, int, int, Optional[int]]]:
+    ) -> list[tuple[str, int, int, int | None]]:
         """
         Get list of forward extremities for a room.
 
@@ -108,7 +108,7 @@ class EventForwardExtremitiesStore(
 
         def get_forward_extremities_for_room_txn(
             txn: LoggingTransaction,
-        ) -> List[Tuple[str, int, int, Optional[int]]]:
+        ) -> list[tuple[str, int, int, int | None]]:
             sql = """
                 SELECT event_id, state_group, depth, received_ts
                 FROM event_forward_extremities
@@ -118,7 +118,7 @@ class EventForwardExtremitiesStore(
             """
 
             txn.execute(sql, (room_id,))
-            return cast(List[Tuple[str, int, int, Optional[int]]], txn.fetchall())
+            return cast(list[tuple[str, int, int, int | None]], txn.fetchall())
 
         return await self.db_pool.runInteraction(
             "get_forward_extremities_for_room",
diff --git a/synapse/storage/databases/main/events_worker.py b/synapse/storage/databases/main/events_worker.py
index 31e2312211..29bc1b982a 100644
--- a/synapse/storage/databases/main/events_worker.py
+++ b/synapse/storage/databases/main/events_worker.py
@@ -27,15 +27,10 @@ from typing import (
     TYPE_CHECKING,
     Any,
     Collection,
-    Dict,
     Iterable,
-    List,
     Literal,
     Mapping,
     MutableMapping,
-    Optional,
-    Set,
-    Tuple,
     cast,
     overload,
 )
@@ -70,7 +65,6 @@ from synapse.logging.opentracing import (
 )
 from synapse.metrics import SERVER_NAME_LABEL
 from synapse.metrics.background_process_metrics import (
-    run_as_background_process,
     wrap_as_background_process,
 )
 from synapse.replication.tcp.streams import BackfillStream, UnPartialStatedEventStream
@@ -151,7 +145,7 @@ class InvalidEventError(Exception):
 @attr.s(slots=True, auto_attribs=True)
 class EventCacheEntry:
     event: EventBase
-    redacted_event: Optional[EventBase]
+    redacted_event: EventBase | None
 
 
 @attr.s(slots=True, frozen=True, auto_attribs=True)
@@ -189,10 +183,10 @@ class _EventRow:
     instance_name: str
     json: str
     internal_metadata: str
-    format_version: Optional[int]
-    room_version_id: Optional[str]
-    rejected_reason: Optional[str]
-    redactions: List[str]
+    format_version: int | None
+    room_version_id: str | None
+    rejected_reason: str | None
+    redactions: list[str]
     outlier: bool
 
 
@@ -282,13 +276,14 @@ class EventsWorkerStore(SQLBaseStore):
 
         if hs.config.worker.run_background_tasks:
             # We periodically clean out old transaction ID mappings
-            self._clock.looping_call(
+            self.clock.looping_call(
                 self._cleanup_old_transaction_ids,
                 5 * 60 * 1000,
             )
 
-        self._get_event_cache: AsyncLruCache[Tuple[str], EventCacheEntry] = (
+        self._get_event_cache: AsyncLruCache[tuple[str], EventCacheEntry] = (
             AsyncLruCache(
+                clock=hs.get_clock(),
                 server_name=self.server_name,
                 cache_name="*getEvent*",
                 max_size=hs.config.caches.event_cache_size,
@@ -300,8 +295,8 @@ class EventsWorkerStore(SQLBaseStore):
         # Map from event ID to a deferred that will result in a map from event
         # ID to cache entry. Note that the returned dict may not have the
         # requested event in it if the event isn't in the DB.
-        self._current_event_fetches: Dict[
-            str, ObservableDeferred[Dict[str, EventCacheEntry]]
+        self._current_event_fetches: dict[
+            str, ObservableDeferred[dict[str, EventCacheEntry]]
         ] = {}
 
         # We keep track of the events we have currently loaded in memory so that
@@ -311,8 +306,8 @@ class EventsWorkerStore(SQLBaseStore):
         self._event_ref: MutableMapping[str, EventBase] = weakref.WeakValueDictionary()
 
         self._event_fetch_lock = threading.Condition()
-        self._event_fetch_list: List[
-            Tuple[Iterable[str], "defer.Deferred[Dict[str, _EventRow]]"]
+        self._event_fetch_list: list[
+            tuple[Iterable[str], "defer.Deferred[dict[str, _EventRow]]"]
         ] = []
         self._event_fetch_ongoing = 0
         event_fetch_ongoing_gauge.labels(**{SERVER_NAME_LABEL: self.server_name}).set(
@@ -323,7 +318,7 @@ class EventsWorkerStore(SQLBaseStore):
         # the DataStore and PersistEventStore.
         def get_chain_id_txn(txn: Cursor) -> int:
             txn.execute("SELECT COALESCE(max(chain_id), 0) FROM event_auth_chains")
-            return cast(Tuple[int], txn.fetchone())[0]
+            return cast(tuple[int], txn.fetchone())[0]
 
         self.event_chain_id_gen = build_sequence_generator(
             db_conn,
@@ -387,7 +382,7 @@ class EventsWorkerStore(SQLBaseStore):
 
     async def get_un_partial_stated_events_from_stream(
         self, instance_name: str, last_id: int, current_id: int, limit: int
-    ) -> Tuple[List[Tuple[int, Tuple[str, bool]]], int, bool]:
+    ) -> tuple[list[tuple[int, tuple[str, bool]]], int, bool]:
         """Get updates for the un-partial-stated events replication stream.
 
         Args:
@@ -414,7 +409,7 @@ class EventsWorkerStore(SQLBaseStore):
 
         def get_un_partial_stated_events_from_stream_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[List[Tuple[int, Tuple[str, bool]]], int, bool]:
+        ) -> tuple[list[tuple[int, tuple[str, bool]]], int, bool]:
             sql = """
                 SELECT stream_id, event_id, rejection_status_changed
                 FROM un_partial_stated_event_stream
@@ -505,7 +500,7 @@ class EventsWorkerStore(SQLBaseStore):
         get_prev_content: bool = ...,
         allow_rejected: bool = ...,
         allow_none: Literal[False] = ...,
-        check_room_id: Optional[str] = ...,
+        check_room_id: str | None = ...,
     ) -> EventBase: ...
 
     @overload
@@ -516,8 +511,8 @@ class EventsWorkerStore(SQLBaseStore):
         get_prev_content: bool = ...,
         allow_rejected: bool = ...,
         allow_none: Literal[True] = ...,
-        check_room_id: Optional[str] = ...,
-    ) -> Optional[EventBase]: ...
+        check_room_id: str | None = ...,
+    ) -> EventBase | None: ...
 
     @cancellable
     async def get_event(
@@ -527,8 +522,8 @@ class EventsWorkerStore(SQLBaseStore):
         get_prev_content: bool = False,
         allow_rejected: bool = False,
         allow_none: bool = False,
-        check_room_id: Optional[str] = None,
-    ) -> Optional[EventBase]:
+        check_room_id: str | None = None,
+    ) -> EventBase | None:
         """Get an event from the database by event_id.
 
         Events for unknown room versions will also be filtered out.
@@ -585,7 +580,7 @@ class EventsWorkerStore(SQLBaseStore):
         redact_behaviour: EventRedactBehaviour = EventRedactBehaviour.redact,
         get_prev_content: bool = False,
         allow_rejected: bool = False,
-    ) -> Dict[str, EventBase]:
+    ) -> dict[str, EventBase]:
         """Get events from the database
 
         Unknown events will be omitted from the response.
@@ -633,7 +628,7 @@ class EventsWorkerStore(SQLBaseStore):
         redact_behaviour: EventRedactBehaviour = EventRedactBehaviour.redact,
         get_prev_content: bool = False,
         allow_rejected: bool = False,
-    ) -> List[EventBase]:
+    ) -> list[EventBase]:
         """Get events from the database and return in a list in the same order
         as given by `event_ids` arg.
 
@@ -792,7 +787,7 @@ class EventsWorkerStore(SQLBaseStore):
         self,
         event_ids: Collection[str],
         allow_rejected: bool = False,
-    ) -> Dict[str, EventCacheEntry]:
+    ) -> dict[str, EventCacheEntry]:
         """Fetch a bunch of events from the cache or the database.
 
         Note that the events pulled by this function will not have any redactions
@@ -836,9 +831,9 @@ class EventsWorkerStore(SQLBaseStore):
         # avoid extraneous work (if we don't do this we can end up in a n^2 mode
         # when we wait on the same Deferred N times, then try and merge the
         # same dict into itself N times).
-        already_fetching_ids: Set[str] = set()
-        already_fetching_deferreds: Set[
-            ObservableDeferred[Dict[str, EventCacheEntry]]
+        already_fetching_ids: set[str] = set()
+        already_fetching_deferreds: set[
+            ObservableDeferred[dict[str, EventCacheEntry]]
         ] = set()
 
         for event_id in missing_events_ids:
@@ -853,7 +848,7 @@ class EventsWorkerStore(SQLBaseStore):
 
         if missing_events_ids:
 
-            async def get_missing_events_from_cache_or_db() -> Dict[
+            async def get_missing_events_from_cache_or_db() -> dict[
                 str, EventCacheEntry
             ]:
                 """Fetches the events in `missing_event_ids` from the database.
@@ -869,7 +864,7 @@ class EventsWorkerStore(SQLBaseStore):
                 # to all the events we pulled from the DB (this will result in this
                 # function returning more events than requested, but that can happen
                 # already due to `_get_events_from_db`).
-                fetching_deferred: ObservableDeferred[Dict[str, EventCacheEntry]] = (
+                fetching_deferred: ObservableDeferred[dict[str, EventCacheEntry]] = (
                     ObservableDeferred(defer.Deferred(), consumeErrors=True)
                 )
                 for event_id in missing_events_ids:
@@ -908,7 +903,7 @@ class EventsWorkerStore(SQLBaseStore):
             # We must allow the database fetch to complete in the presence of
             # cancellations, since multiple `_get_events_from_cache_or_db` calls can
             # reuse the same fetch.
-            missing_events: Dict[str, EventCacheEntry] = await delay_cancellation(
+            missing_events: dict[str, EventCacheEntry] = await delay_cancellation(
                 get_missing_events_from_cache_or_db()
             )
             event_entry_map.update(missing_events)
@@ -999,7 +994,7 @@ class EventsWorkerStore(SQLBaseStore):
 
     async def _get_events_from_cache(
         self, events: Iterable[str], update_metrics: bool = True
-    ) -> Dict[str, EventCacheEntry]:
+    ) -> dict[str, EventCacheEntry]:
         """Fetch events from the caches, both in memory and any external.
 
         May return rejected events.
@@ -1025,7 +1020,7 @@ class EventsWorkerStore(SQLBaseStore):
     @trace
     async def _get_events_from_external_cache(
         self, events: Collection[str], update_metrics: bool = True
-    ) -> Dict[str, EventCacheEntry]:
+    ) -> dict[str, EventCacheEntry]:
         """Fetch events from any configured external cache.
 
         May return rejected events.
@@ -1051,7 +1046,7 @@ class EventsWorkerStore(SQLBaseStore):
 
     def _get_events_from_local_cache(
         self, events: Iterable[str], update_metrics: bool = True
-    ) -> Dict[str, EventCacheEntry]:
+    ) -> dict[str, EventCacheEntry]:
         """Fetch events from the local, in memory, caches.
 
         May return rejected events.
@@ -1094,8 +1089,8 @@ class EventsWorkerStore(SQLBaseStore):
         self,
         context: EventContext,
         state_keys_to_include: StateFilter,
-        membership_user_id: Optional[str] = None,
-    ) -> List[JsonDict]:
+        membership_user_id: str | None = None,
+    ) -> list[JsonDict]:
         """
         Retrieve the stripped state from a room, given an event context to retrieve state
         from as well as the state types to include. Optionally, include the membership
@@ -1154,9 +1149,7 @@ class EventsWorkerStore(SQLBaseStore):
                 should_start = False
 
         if should_start:
-            run_as_background_process(
-                "fetch_events", self.server_name, self._fetch_thread
-            )
+            self.hs.run_as_background_process("fetch_events", self._fetch_thread)
 
     async def _fetch_thread(self) -> None:
         """Services requests for events from `_event_fetch_list`."""
@@ -1259,7 +1252,7 @@ class EventsWorkerStore(SQLBaseStore):
     def _fetch_event_list(
         self,
         conn: LoggingDatabaseConnection,
-        event_list: List[Tuple[Iterable[str], "defer.Deferred[Dict[str, _EventRow]]"]],
+        event_list: list[tuple[Iterable[str], "defer.Deferred[dict[str, _EventRow]]"]],
     ) -> None:
         """Handle a load of requests from the _event_fetch_list queue
 
@@ -1276,7 +1269,7 @@ class EventsWorkerStore(SQLBaseStore):
                 were not part of this request.
         """
         with Measure(
-            self._clock, name="_fetch_event_list", server_name=self.server_name
+            self.clock, name="_fetch_event_list", server_name=self.server_name
         ):
             try:
                 events_to_fetch = {
@@ -1314,7 +1307,7 @@ class EventsWorkerStore(SQLBaseStore):
     @trace
     async def _get_events_from_db(
         self, event_ids: Collection[str]
-    ) -> Dict[str, EventCacheEntry]:
+    ) -> dict[str, EventCacheEntry]:
         """Fetch a bunch of events from the database.
 
         May return rejected events.
@@ -1335,8 +1328,8 @@ class EventsWorkerStore(SQLBaseStore):
             str(len(event_ids)),
         )
 
-        fetched_event_ids: Set[str] = set()
-        fetched_events: Dict[str, _EventRow] = {}
+        fetched_event_ids: set[str] = set()
+        fetched_events: dict[str, _EventRow] = {}
 
         @trace
         async def _fetch_event_ids_and_get_outstanding_redactions(
@@ -1353,7 +1346,7 @@ class EventsWorkerStore(SQLBaseStore):
             row_map = await self._enqueue_events(event_ids_to_fetch)
 
             # we need to recursively fetch any redactions of those events
-            redaction_ids: Set[str] = set()
+            redaction_ids: set[str] = set()
             for event_id in event_ids_to_fetch:
                 row = row_map.get(event_id)
                 fetched_event_ids.add(event_id)
@@ -1380,7 +1373,7 @@ class EventsWorkerStore(SQLBaseStore):
                 )
 
         # build a map from event_id to EventBase
-        event_map: Dict[str, EventBase] = {}
+        event_map: dict[str, EventBase] = {}
         for event_id, row in fetched_events.items():
             assert row.event_id == event_id
 
@@ -1409,7 +1402,7 @@ class EventsWorkerStore(SQLBaseStore):
 
             room_version_id = row.room_version_id
 
-            room_version: Optional[RoomVersion]
+            room_version: RoomVersion | None
             if not room_version_id:
                 # this should only happen for out-of-band membership events which
                 # arrived before https://github.com/matrix-org/synapse/issues/6983
@@ -1493,7 +1486,7 @@ class EventsWorkerStore(SQLBaseStore):
 
         # finally, we can decide whether each one needs redacting, and build
         # the cache entries.
-        result_map: Dict[str, EventCacheEntry] = {}
+        result_map: dict[str, EventCacheEntry] = {}
         for event_id, original_ev in event_map.items():
             redactions = fetched_events[event_id].redactions
             redacted_event = self._maybe_redact_event_row(
@@ -1513,7 +1506,7 @@ class EventsWorkerStore(SQLBaseStore):
 
         return result_map
 
-    async def _enqueue_events(self, events: Collection[str]) -> Dict[str, _EventRow]:
+    async def _enqueue_events(self, events: Collection[str]) -> dict[str, _EventRow]:
         """Fetches events from the database using the _event_fetch_list. This
         allows batch and bulk fetching of events - it allows us to fetch events
         without having to create a new transaction for each request for events.
@@ -1526,7 +1519,7 @@ class EventsWorkerStore(SQLBaseStore):
             that weren't requested.
         """
 
-        events_d: "defer.Deferred[Dict[str, _EventRow]]" = defer.Deferred()
+        events_d: "defer.Deferred[dict[str, _EventRow]]" = defer.Deferred()
         with self._event_fetch_lock:
             self._event_fetch_list.append((events, events_d))
             self._event_fetch_lock.notify()
@@ -1542,7 +1535,7 @@ class EventsWorkerStore(SQLBaseStore):
 
     def _fetch_event_rows(
         self, txn: LoggingTransaction, event_ids: Iterable[str]
-    ) -> Dict[str, _EventRow]:
+    ) -> dict[str, _EventRow]:
         """Fetch event rows from the database
 
         Events which are not found are omitted from the result.
@@ -1609,7 +1602,7 @@ class EventsWorkerStore(SQLBaseStore):
 
             # check for MSC4932 redactions
             to_check = []
-            events: List[_EventRow] = []
+            events: list[_EventRow] = []
             for e in evs:
                 event = event_dict.get(e)
                 if not event:
@@ -1658,8 +1651,8 @@ class EventsWorkerStore(SQLBaseStore):
         self,
         original_ev: EventBase,
         redactions: Iterable[str],
-        event_map: Dict[str, EventBase],
-    ) -> Optional[EventBase]:
+        event_map: dict[str, EventBase],
+    ) -> EventBase | None:
         """Given an event object and a list of possible redacting event ids,
         determine whether to honour any of those redactions and if so return a redacted
         event.
@@ -1729,12 +1722,12 @@ class EventsWorkerStore(SQLBaseStore):
         # no valid redaction found for this event
         return None
 
-    async def have_events_in_timeline(self, event_ids: Iterable[str]) -> Set[str]:
+    async def have_events_in_timeline(self, event_ids: Iterable[str]) -> set[str]:
         """Given a list of event ids, check if we have already processed and
         stored them as non outliers.
         """
         rows = cast(
-            List[Tuple[str]],
+            list[tuple[str]],
             await self.db_pool.simple_select_many_batch(
                 table="events",
                 retcols=("event_id",),
@@ -1751,7 +1744,7 @@ class EventsWorkerStore(SQLBaseStore):
     @tag_args
     async def have_seen_events(
         self, room_id: str, event_ids: Iterable[str]
-    ) -> Set[str]:
+    ) -> set[str]:
         """Given a list of event ids, check if we have already processed them.
 
         The room_id is only used to structure the cache (so that it can later be
@@ -1770,7 +1763,7 @@ class EventsWorkerStore(SQLBaseStore):
         # we break it down. However, each batch requires its own index scan, so we make
         # the batches as big as possible.
 
-        results: Set[str] = set()
+        results: set[str] = set()
         for event_ids_chunk in batch_iter(event_ids, 500):
             events_seen_dict = await self._have_seen_events_dict(
                 room_id, event_ids_chunk
@@ -1800,7 +1793,7 @@ class EventsWorkerStore(SQLBaseStore):
         #  not being invalidated when purging events from a room. The optimisation can
         #  be re-added after https://github.com/matrix-org/synapse/issues/13476
 
-        def have_seen_events_txn(txn: LoggingTransaction) -> Dict[str, bool]:
+        def have_seen_events_txn(txn: LoggingTransaction) -> dict[str, bool]:
             # we deliberately do *not* query the database for room_id, to make the
             # query an index-only lookup on `events_event_id_key`.
             #
@@ -1852,7 +1845,7 @@ class EventsWorkerStore(SQLBaseStore):
             room_id,
         )
 
-    async def get_room_complexity(self, room_id: str) -> Dict[str, float]:
+    async def get_room_complexity(self, room_id: str) -> dict[str, float]:
         """
         Get a rough approximation of the complexity of the room. This is used by
         remote servers to decide whether they wish to join the room or not.
@@ -1875,7 +1868,7 @@ class EventsWorkerStore(SQLBaseStore):
 
     async def get_all_new_forward_event_rows(
         self, instance_name: str, last_id: int, current_id: int, limit: int
-    ) -> List[Tuple[int, str, str, str, str, str, str, str, bool, bool]]:
+    ) -> list[tuple[int, str, str, str, str, str, str, str, bool, bool]]:
         """Returns new events, for the Events replication stream
 
         Args:
@@ -1891,7 +1884,7 @@ class EventsWorkerStore(SQLBaseStore):
 
         def get_all_new_forward_event_rows(
             txn: LoggingTransaction,
-        ) -> List[Tuple[int, str, str, str, str, str, str, str, bool, bool]]:
+        ) -> list[tuple[int, str, str, str, str, str, str, str, bool, bool]]:
             sql = (
                 "SELECT e.stream_ordering, e.event_id, e.room_id, e.type,"
                 " se.state_key, redacts, relates_to_id, membership, rejections.reason IS NOT NULL,"
@@ -1909,7 +1902,7 @@ class EventsWorkerStore(SQLBaseStore):
             )
             txn.execute(sql, (last_id, current_id, instance_name, limit))
             return cast(
-                List[Tuple[int, str, str, str, str, str, str, str, bool, bool]],
+                list[tuple[int, str, str, str, str, str, str, str, bool, bool]],
                 txn.fetchall(),
             )
 
@@ -1919,7 +1912,7 @@ class EventsWorkerStore(SQLBaseStore):
 
     async def get_ex_outlier_stream_rows(
         self, instance_name: str, last_id: int, current_id: int
-    ) -> List[Tuple[int, str, str, str, str, str, str, str, bool, bool]]:
+    ) -> list[tuple[int, str, str, str, str, str, str, str, bool, bool]]:
         """Returns de-outliered events, for the Events replication stream
 
         Args:
@@ -1934,7 +1927,7 @@ class EventsWorkerStore(SQLBaseStore):
 
         def get_ex_outlier_stream_rows_txn(
             txn: LoggingTransaction,
-        ) -> List[Tuple[int, str, str, str, str, str, str, str, bool, bool]]:
+        ) -> list[tuple[int, str, str, str, str, str, str, str, bool, bool]]:
             sql = (
                 "SELECT out.event_stream_ordering, e.event_id, e.room_id, e.type,"
                 " se.state_key, redacts, relates_to_id, membership, rejections.reason IS NOT NULL,"
@@ -1956,7 +1949,7 @@ class EventsWorkerStore(SQLBaseStore):
 
             txn.execute(sql, (last_id, current_id, instance_name))
             return cast(
-                List[Tuple[int, str, str, str, str, str, str, str, bool, bool]],
+                list[tuple[int, str, str, str, str, str, str, str, bool, bool]],
                 txn.fetchall(),
             )
 
@@ -1966,7 +1959,7 @@ class EventsWorkerStore(SQLBaseStore):
 
     async def get_all_new_backfill_event_rows(
         self, instance_name: str, last_id: int, current_id: int, limit: int
-    ) -> Tuple[List[Tuple[int, Tuple[str, str, str, str, str, str]]], int, bool]:
+    ) -> tuple[list[tuple[int, tuple[str, str, str, str, str, str]]], int, bool]:
         """Get updates for backfill replication stream, including all new
         backfilled events and events that have gone from being outliers to not.
 
@@ -1996,7 +1989,7 @@ class EventsWorkerStore(SQLBaseStore):
 
         def get_all_new_backfill_event_rows(
             txn: LoggingTransaction,
-        ) -> Tuple[List[Tuple[int, Tuple[str, str, str, str, str, str]]], int, bool]:
+        ) -> tuple[list[tuple[int, tuple[str, str, str, str, str, str]]], int, bool]:
             sql = (
                 "SELECT -e.stream_ordering, e.event_id, e.room_id, e.type,"
                 " se.state_key, redacts, relates_to_id"
@@ -2010,10 +2003,10 @@ class EventsWorkerStore(SQLBaseStore):
                 " LIMIT ?"
             )
             txn.execute(sql, (-last_id, -current_id, instance_name, limit))
-            new_event_updates: List[
-                Tuple[int, Tuple[str, str, str, str, str, str]]
+            new_event_updates: list[
+                tuple[int, tuple[str, str, str, str, str, str]]
             ] = []
-            row: Tuple[int, str, str, str, str, str, str]
+            row: tuple[int, str, str, str, str, str, str]
             # Type safety: iterating over `txn` yields `Tuple`, i.e.
             # `Tuple[Any, ...]` of arbitrary length. Mypy detects assigning a
             # variadic tuple to a fixed length tuple and flags it up as an error.
@@ -2059,7 +2052,7 @@ class EventsWorkerStore(SQLBaseStore):
 
     async def get_all_updated_current_state_deltas(
         self, instance_name: str, from_token: int, to_token: int, target_row_count: int
-    ) -> Tuple[List[Tuple[int, str, str, str, str]], int, bool]:
+    ) -> tuple[list[tuple[int, str, str, str, str]], int, bool]:
         """Fetch updates from current_state_delta_stream
 
         Args:
@@ -2081,7 +2074,7 @@ class EventsWorkerStore(SQLBaseStore):
 
         def get_all_updated_current_state_deltas_txn(
             txn: LoggingTransaction,
-        ) -> List[Tuple[int, str, str, str, str]]:
+        ) -> list[tuple[int, str, str, str, str]]:
             sql = """
                 SELECT stream_id, room_id, type, state_key, event_id
                 FROM current_state_delta_stream
@@ -2090,23 +2083,23 @@ class EventsWorkerStore(SQLBaseStore):
                 ORDER BY stream_id ASC LIMIT ?
             """
             txn.execute(sql, (from_token, to_token, instance_name, target_row_count))
-            return cast(List[Tuple[int, str, str, str, str]], txn.fetchall())
+            return cast(list[tuple[int, str, str, str, str]], txn.fetchall())
 
         def get_deltas_for_stream_id_txn(
             txn: LoggingTransaction, stream_id: int
-        ) -> List[Tuple[int, str, str, str, str]]:
+        ) -> list[tuple[int, str, str, str, str]]:
             sql = """
                 SELECT stream_id, room_id, type, state_key, event_id
                 FROM current_state_delta_stream
                 WHERE stream_id = ?
             """
             txn.execute(sql, [stream_id])
-            return cast(List[Tuple[int, str, str, str, str]], txn.fetchall())
+            return cast(list[tuple[int, str, str, str, str]], txn.fetchall())
 
         # we need to make sure that, for every stream id in the results, we get *all*
         # the rows with that stream id.
 
-        rows: List[Tuple[int, str, str, str, str]] = await self.db_pool.runInteraction(
+        rows: list[tuple[int, str, str, str, str]] = await self.db_pool.runInteraction(
             "get_all_updated_current_state_deltas",
             get_all_updated_current_state_deltas_txn,
         )
@@ -2137,7 +2130,7 @@ class EventsWorkerStore(SQLBaseStore):
 
     async def get_senders_for_event_ids(
         self, event_ids: Collection[str]
-    ) -> Dict[str, Optional[str]]:
+    ) -> dict[str, str | None]:
         """
         Given a sequence of event IDs, return the sender associated with each.
 
@@ -2153,7 +2146,7 @@ class EventsWorkerStore(SQLBaseStore):
 
         def _get_senders_for_event_ids(
             txn: LoggingTransaction,
-        ) -> Dict[str, Optional[str]]:
+        ) -> dict[str, str | None]:
             rows = self.db_pool.simple_select_many_txn(
                 txn=txn,
                 table="events",
@@ -2169,7 +2162,7 @@ class EventsWorkerStore(SQLBaseStore):
         )
 
     @cached(max_entries=5000)
-    async def get_event_ordering(self, event_id: str, room_id: str) -> Tuple[int, int]:
+    async def get_event_ordering(self, event_id: str, room_id: str) -> tuple[int, int]:
         res = await self.db_pool.simple_select_one(
             table="events",
             retcols=["topological_ordering", "stream_ordering"],
@@ -2184,7 +2177,7 @@ class EventsWorkerStore(SQLBaseStore):
 
         return int(res[0]), int(res[1])
 
-    async def get_next_event_to_expire(self) -> Optional[Tuple[str, int]]:
+    async def get_next_event_to_expire(self) -> tuple[str, int] | None:
         """Retrieve the entry with the lowest expiry timestamp in the event_expiry
         table, or None if there's no more event to expire.
 
@@ -2196,7 +2189,7 @@ class EventsWorkerStore(SQLBaseStore):
 
         def get_next_event_to_expire_txn(
             txn: LoggingTransaction,
-        ) -> Optional[Tuple[str, int]]:
+        ) -> tuple[str, int] | None:
             txn.execute(
                 """
                 SELECT event_id, expiry_ts FROM event_expiry
@@ -2204,7 +2197,7 @@ class EventsWorkerStore(SQLBaseStore):
                 """
             )
 
-            return cast(Optional[Tuple[str, int]], txn.fetchone())
+            return cast(tuple[str, int] | None, txn.fetchone())
 
         return await self.db_pool.runInteraction(
             desc="get_next_event_to_expire", func=get_next_event_to_expire_txn
@@ -2212,7 +2205,7 @@ class EventsWorkerStore(SQLBaseStore):
 
     async def get_event_id_from_transaction_id_and_device_id(
         self, room_id: str, user_id: str, device_id: str, txn_id: str
-    ) -> Optional[str]:
+    ) -> str | None:
         """Look up if we have already persisted an event for the transaction ID,
         returning the event ID if so.
         """
@@ -2231,7 +2224,7 @@ class EventsWorkerStore(SQLBaseStore):
 
     async def get_already_persisted_events(
         self, events: Iterable[EventBase]
-    ) -> Dict[str, str]:
+    ) -> dict[str, str]:
         """Look up if we have already persisted an event for the transaction ID,
         returning a mapping from event ID in the given list to the event ID of
         an existing event.
@@ -2241,7 +2234,7 @@ class EventsWorkerStore(SQLBaseStore):
         """
 
         mapping = {}
-        txn_id_to_event: Dict[Tuple[str, str, str, str], str] = {}
+        txn_id_to_event: dict[tuple[str, str, str, str], str] = {}
 
         for event in events:
             device_id = getattr(event.internal_metadata, "device_id", None)
@@ -2278,7 +2271,7 @@ class EventsWorkerStore(SQLBaseStore):
         """Cleans out transaction id mappings older than 24hrs."""
 
         def _cleanup_old_transaction_ids_txn(txn: LoggingTransaction) -> None:
-            one_day_ago = self._clock.time_msec() - 24 * 60 * 60 * 1000
+            one_day_ago = self.clock.time_msec() - 24 * 60 * 60 * 1000
             sql = """
                 DELETE FROM event_txn_id_device_id
                 WHERE inserted_ts < ?
@@ -2433,7 +2426,7 @@ class EventsWorkerStore(SQLBaseStore):
 
     async def get_event_id_for_timestamp(
         self, room_id: str, timestamp: int, direction: Direction
-    ) -> Optional[str]:
+    ) -> str | None:
         """Find the closest event to the given timestamp in the given direction.
 
         Args:
@@ -2487,7 +2480,7 @@ class EventsWorkerStore(SQLBaseStore):
             LIMIT 1;
         """
 
-        def get_event_id_for_timestamp_txn(txn: LoggingTransaction) -> Optional[str]:
+        def get_event_id_for_timestamp_txn(txn: LoggingTransaction) -> str | None:
             txn.execute(
                 sql_template,
                 (room_id, timestamp),
@@ -2518,7 +2511,7 @@ class EventsWorkerStore(SQLBaseStore):
             any of the events which are unknown (or are outliers).
         """
         result = cast(
-            List[Tuple[str]],
+            list[tuple[str]],
             await self.db_pool.simple_select_many_batch(
                 table="partial_state_events",
                 column="event_id",
@@ -2543,7 +2536,7 @@ class EventsWorkerStore(SQLBaseStore):
         )
         return result is not None
 
-    async def get_partial_state_events_batch(self, room_id: str) -> List[str]:
+    async def get_partial_state_events_batch(self, room_id: str) -> list[str]:
         """
         Get a list of events in the given room that:
         - have partial state; and
@@ -2562,7 +2555,7 @@ class EventsWorkerStore(SQLBaseStore):
     @staticmethod
     def _get_partial_state_events_batch_txn(
         txn: LoggingTransaction, room_id: str
-    ) -> List[str]:
+    ) -> list[str]:
         # we want to work through the events from oldest to newest, so
         # we only want events whose prev_events do *not* have partial state - hence
         # the 'NOT EXISTS' clause in the below.
@@ -2597,7 +2590,7 @@ class EventsWorkerStore(SQLBaseStore):
         self,
         txn: LoggingTransaction,
         event_id: str,
-        rejection_reason: Optional[str],
+        rejection_reason: str | None,
     ) -> None:
         """Mark an event that was previously accepted as rejected, or vice versa
 
@@ -2633,7 +2626,7 @@ class EventsWorkerStore(SQLBaseStore):
                 keyvalues={"event_id": event_id},
                 values={
                     "reason": rejection_reason,
-                    "last_check": self._clock.time_msec(),
+                    "last_check": self.clock.time_msec(),
                 },
             )
         self.db_pool.simple_update_txn(
@@ -2646,8 +2639,8 @@ class EventsWorkerStore(SQLBaseStore):
         self.invalidate_get_event_cache_after_txn(txn, event_id)
 
     async def get_events_sent_by_user_in_room(
-        self, user_id: str, room_id: str, limit: int, filter: Optional[List[str]] = None
-    ) -> Optional[List[str]]:
+        self, user_id: str, room_id: str, limit: int, filter: list[str] | None = None
+    ) -> list[str] | None:
         """
         Get a list of event ids of events sent by the user in the specified room
 
@@ -2662,10 +2655,10 @@ class EventsWorkerStore(SQLBaseStore):
             txn: LoggingTransaction,
             user_id: str,
             room_id: str,
-            filter: Optional[List[str]],
+            filter: list[str] | None,
             batch_size: int,
             offset: int,
-        ) -> Tuple[Optional[List[str]], int]:
+        ) -> tuple[list[str] | None, int]:
             if filter:
                 base_clause, args = make_in_list_sql_clause(
                     txn.database_engine, "type", filter
@@ -2698,7 +2691,7 @@ class EventsWorkerStore(SQLBaseStore):
         if batch_size > limit:
             batch_size = limit
 
-        selected_ids: List[str] = []
+        selected_ids: list[str] = []
         while offset < limit:
             res, offset = await self.db_pool.runInteraction(
                 "get_events_by_user",
@@ -2773,7 +2766,7 @@ class EventsWorkerStore(SQLBaseStore):
     @cached(tree=True)
     async def get_metadata_for_event(
         self, room_id: str, event_id: str
-    ) -> Optional[EventMetadata]:
+    ) -> EventMetadata | None:
         row = await self.db_pool.simple_select_one(
             table="events",
             keyvalues={"room_id": room_id, "event_id": event_id},
diff --git a/synapse/storage/databases/main/experimental_features.py b/synapse/storage/databases/main/experimental_features.py
index d980c57fa8..77b6c36884 100644
--- a/synapse/storage/databases/main/experimental_features.py
+++ b/synapse/storage/databases/main/experimental_features.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import TYPE_CHECKING, Dict, FrozenSet, List, Tuple, cast
+from typing import TYPE_CHECKING, cast
 
 from synapse.storage.database import (
     DatabasePool,
@@ -44,7 +44,7 @@ class ExperimentalFeaturesStore(CacheInvalidationWorkerStore):
         super().__init__(database, db_conn, hs)
 
     @cached()
-    async def list_enabled_features(self, user_id: str) -> FrozenSet[str]:
+    async def list_enabled_features(self, user_id: str) -> frozenset[str]:
         """
         Checks to see what features are enabled for a given user
         Args:
@@ -54,7 +54,7 @@ class ExperimentalFeaturesStore(CacheInvalidationWorkerStore):
             the features currently enabled for the user
         """
         enabled = cast(
-            List[Tuple[str]],
+            list[tuple[str]],
             await self.db_pool.simple_select_list(
                 table="per_user_experimental_features",
                 keyvalues={"user_id": user_id, "enabled": True},
@@ -67,7 +67,7 @@ class ExperimentalFeaturesStore(CacheInvalidationWorkerStore):
     async def set_features_for_user(
         self,
         user: str,
-        features: Dict["ExperimentalFeature", bool],
+        features: dict["ExperimentalFeature", bool],
     ) -> None:
         """
         Enables or disables features for a given user
diff --git a/synapse/storage/databases/main/filtering.py b/synapse/storage/databases/main/filtering.py
index af9634bad4..2019ad9904 100644
--- a/synapse/storage/databases/main/filtering.py
+++ b/synapse/storage/databases/main/filtering.py
@@ -20,7 +20,7 @@
 #
 #
 
-from typing import TYPE_CHECKING, Optional, Tuple, Union, cast
+from typing import TYPE_CHECKING, cast
 
 from canonicaljson import encode_canonical_json
 
@@ -72,7 +72,7 @@ class FilteringWorkerStore(SQLBaseStore):
 
         lower_bound_id = progress.get("lower_bound_id", "")
 
-        def _get_last_id(txn: LoggingTransaction) -> Optional[str]:
+        def _get_last_id(txn: LoggingTransaction) -> str | None:
             sql = """
                     SELECT user_id FROM user_filters
                     WHERE user_id > ?
@@ -151,7 +151,7 @@ class FilteringWorkerStore(SQLBaseStore):
 
     @cached(num_args=2)
     async def get_user_filter(
-        self, user_id: UserID, filter_id: Union[int, str]
+        self, user_id: UserID, filter_id: int | str
     ) -> JsonMapping:
         # filter_id is BIGINT UNSIGNED, so if it isn't a number, fail
         # with a coherent error message rather than 500 M_UNKNOWN.
@@ -187,7 +187,7 @@ class FilteringWorkerStore(SQLBaseStore):
 
             sql = "SELECT MAX(filter_id) FROM user_filters WHERE full_user_id = ?"
             txn.execute(sql, (user_id.to_string(),))
-            max_id = cast(Tuple[Optional[int]], txn.fetchone())[0]
+            max_id = cast(tuple[int | None], txn.fetchone())[0]
             if max_id is None:
                 filter_id = 0
             else:
diff --git a/synapse/storage/databases/main/keys.py b/synapse/storage/databases/main/keys.py
index 2a99a97dd6..f81257b5a1 100644
--- a/synapse/storage/databases/main/keys.py
+++ b/synapse/storage/databases/main/keys.py
@@ -22,7 +22,7 @@
 import itertools
 import json
 import logging
-from typing import Dict, Iterable, List, Mapping, Optional, Tuple, Union, cast
+from typing import Iterable, Mapping, cast
 
 from canonicaljson import encode_canonical_json
 from signedjson.key import decode_verify_key_bytes
@@ -50,7 +50,7 @@ class KeyStore(CacheInvalidationWorkerStore):
         server_name: str,
         from_server: str,
         ts_added_ms: int,
-        verify_keys: Dict[str, FetchKeyResult],
+        verify_keys: dict[str, FetchKeyResult],
         response_json: JsonDict,
     ) -> None:
         """Stores the keys for the given server that we got from `from_server`.
@@ -130,7 +130,7 @@ class KeyStore(CacheInvalidationWorkerStore):
 
     @cached()
     def _get_server_keys_json(
-        self, server_name_and_key_id: Tuple[str, str]
+        self, server_name_and_key_id: tuple[str, str]
     ) -> FetchKeyResult:
         raise NotImplementedError()
 
@@ -138,8 +138,8 @@ class KeyStore(CacheInvalidationWorkerStore):
         cached_method_name="_get_server_keys_json", list_name="server_name_and_key_ids"
     )
     async def get_server_keys_json(
-        self, server_name_and_key_ids: Iterable[Tuple[str, str]]
-    ) -> Mapping[Tuple[str, str], FetchKeyResult]:
+        self, server_name_and_key_ids: Iterable[tuple[str, str]]
+    ) -> Mapping[tuple[str, str], FetchKeyResult]:
         """
         Args:
             server_name_and_key_ids:
@@ -151,7 +151,7 @@ class KeyStore(CacheInvalidationWorkerStore):
         """
         keys = {}
 
-        def _get_keys(txn: Cursor, batch: Tuple[Tuple[str, str], ...]) -> None:
+        def _get_keys(txn: Cursor, batch: tuple[tuple[str, str], ...]) -> None:
             """Processes a batch of keys to fetch, and adds the result to `keys`."""
 
             # batch_iter always returns tuples so it's safe to do len(batch)
@@ -189,7 +189,7 @@ class KeyStore(CacheInvalidationWorkerStore):
                     valid_until_ts=ts_valid_until_ms,
                 )
 
-        def _txn(txn: Cursor) -> Dict[Tuple[str, str], FetchKeyResult]:
+        def _txn(txn: Cursor) -> dict[tuple[str, str], FetchKeyResult]:
             for batch in batch_iter(server_name_and_key_ids, 50):
                 _get_keys(txn, batch)
             return keys
@@ -201,7 +201,7 @@ class KeyStore(CacheInvalidationWorkerStore):
         self,
         server_name: str,
         key_id: str,
-    ) -> Optional[FetchKeyResultForRemote]:
+    ) -> FetchKeyResultForRemote | None:
         raise NotImplementedError()
 
     @cachedList(
@@ -209,13 +209,13 @@ class KeyStore(CacheInvalidationWorkerStore):
     )
     async def get_server_keys_json_for_remote(
         self, server_name: str, key_ids: Iterable[str]
-    ) -> Mapping[str, Optional[FetchKeyResultForRemote]]:
+    ) -> Mapping[str, FetchKeyResultForRemote | None]:
         """Fetch the cached keys for the given server/key IDs.
 
         If we have multiple entries for a given key ID, returns the most recent.
         """
         rows = cast(
-            List[Tuple[str, str, int, int, Union[bytes, memoryview]]],
+            list[tuple[str, str, int, int, bytes | memoryview]],
             await self.db_pool.simple_select_many_batch(
                 table="server_keys_json",
                 column="key_id",
@@ -252,13 +252,13 @@ class KeyStore(CacheInvalidationWorkerStore):
     async def get_all_server_keys_json_for_remote(
         self,
         server_name: str,
-    ) -> Dict[str, FetchKeyResultForRemote]:
+    ) -> dict[str, FetchKeyResultForRemote]:
         """Fetch the cached keys for the given server.
 
         If we have multiple entries for a given key ID, returns the most recent.
         """
         rows = cast(
-            List[Tuple[str, str, int, int, Union[bytes, memoryview]]],
+            list[tuple[str, str, int, int, bytes | memoryview]],
             await self.db_pool.simple_select_list(
                 table="server_keys_json",
                 keyvalues={"server_name": server_name},
diff --git a/synapse/storage/databases/main/lock.py b/synapse/storage/databases/main/lock.py
index d0e4a91b59..51f04acbcb 100644
--- a/synapse/storage/databases/main/lock.py
+++ b/synapse/storage/databases/main/lock.py
@@ -21,14 +21,13 @@
 import logging
 from contextlib import AsyncExitStack
 from types import TracebackType
-from typing import TYPE_CHECKING, Collection, Optional, Set, Tuple, Type
+from typing import TYPE_CHECKING, Collection, Optional
 from weakref import WeakValueDictionary
 
 from twisted.internet import defer
 from twisted.internet.task import LoopingCall
 
 from synapse.metrics.background_process_metrics import (
-    run_as_background_process,
     wrap_as_background_process,
 )
 from synapse.storage._base import SQLBaseStore
@@ -83,7 +82,7 @@ class LockStore(SQLBaseStore):
 
         # A map from `(lock_name, lock_key)` to lock that we think we
         # currently hold.
-        self._live_lock_tokens: WeakValueDictionary[Tuple[str, str], Lock] = (
+        self._live_lock_tokens: WeakValueDictionary[tuple[str, str], Lock] = (
             WeakValueDictionary()
         )
 
@@ -92,22 +91,22 @@ class LockStore(SQLBaseStore):
         # multiple read locks at a time but only one write lock (no mixing read
         # and write locks at the same time).
         self._live_read_write_lock_tokens: WeakValueDictionary[
-            Tuple[str, str, str], Lock
+            tuple[str, str, str], Lock
         ] = WeakValueDictionary()
 
         # When we shut down we want to remove the locks. Technically this can
         # lead to a race, as we may drop the lock while we are still processing.
         # However, a) it should be a small window, b) the lock is best effort
         # anyway and c) we want to really avoid leaking locks when we restart.
-        hs.get_clock().add_system_event_trigger(
-            "before",
-            "shutdown",
-            self._on_shutdown,
+        hs.register_async_shutdown_handler(
+            phase="before",
+            eventType="shutdown",
+            shutdown_func=self._on_shutdown,
         )
 
-        self._acquiring_locks: Set[Tuple[str, str]] = set()
+        self._acquiring_locks: set[tuple[str, str]] = set()
 
-        self._clock.looping_call(
+        self.clock.looping_call(
             self._reap_stale_read_write_locks, _LOCK_TIMEOUT_MS / 10.0
         )
 
@@ -153,7 +152,7 @@ class LockStore(SQLBaseStore):
         if lock and await lock.is_still_valid():
             return None
 
-        now = self._clock.time_msec()
+        now = self.clock.time_msec()
         token = random_string(6)
 
         def _try_acquire_lock_txn(txn: LoggingTransaction) -> bool:
@@ -202,7 +201,8 @@ class LockStore(SQLBaseStore):
         lock = Lock(
             self.server_name,
             self._reactor,
-            self._clock,
+            self.hs,
+            self.clock,
             self,
             read_write=False,
             lock_name=lock_name,
@@ -251,7 +251,7 @@ class LockStore(SQLBaseStore):
         # constraints. If it doesn't then we have acquired the lock,
         # otherwise we haven't.
 
-        now = self._clock.time_msec()
+        now = self.clock.time_msec()
         token = random_string(6)
 
         self.db_pool.simple_insert_txn(
@@ -270,7 +270,8 @@ class LockStore(SQLBaseStore):
         lock = Lock(
             self.server_name,
             self._reactor,
-            self._clock,
+            self.hs,
+            self.clock,
             self,
             read_write=True,
             lock_name=lock_name,
@@ -287,9 +288,9 @@ class LockStore(SQLBaseStore):
 
     async def try_acquire_multi_read_write_lock(
         self,
-        lock_names: Collection[Tuple[str, str]],
+        lock_names: Collection[tuple[str, str]],
         write: bool,
-    ) -> Optional[AsyncExitStack]:
+    ) -> AsyncExitStack | None:
         """Try to acquire multiple locks for the given names/keys. Will return
         an async context manager if the locks are successfully acquired, which
         *must* be used (otherwise the lock will leak).
@@ -317,7 +318,7 @@ class LockStore(SQLBaseStore):
     def _try_acquire_multi_read_write_lock_txn(
         self,
         txn: LoggingTransaction,
-        lock_names: Collection[Tuple[str, str]],
+        lock_names: Collection[tuple[str, str]],
         write: bool,
     ) -> Collection["Lock"]:
         locks = []
@@ -338,7 +339,7 @@ class LockStore(SQLBaseStore):
         """
 
         def reap_stale_read_write_locks_txn(txn: LoggingTransaction) -> None:
-            txn.execute(delete_sql, (self._clock.time_msec() - _LOCK_TIMEOUT_MS,))
+            txn.execute(delete_sql, (self.clock.time_msec() - _LOCK_TIMEOUT_MS,))
             if txn.rowcount:
                 logger.info("Reaped %d stale locks", txn.rowcount)
 
@@ -374,6 +375,7 @@ class Lock:
         self,
         server_name: str,
         reactor: ISynapseReactor,
+        hs: "HomeServer",
         clock: Clock,
         store: LockStore,
         read_write: bool,
@@ -387,6 +389,7 @@ class Lock:
         """
         self._server_name = server_name
         self._reactor = reactor
+        self._hs = hs
         self._clock = clock
         self._store = store
         self._read_write = read_write
@@ -399,7 +402,7 @@ class Lock:
 
         # We might be called from a non-main thread, so we defer setting up the
         # looping call.
-        self._looping_call: Optional[LoopingCall] = None
+        self._looping_call: LoopingCall | None = None
         reactor.callFromThread(self._setup_looping_call)
 
         self._dropped = False
@@ -410,6 +413,7 @@ class Lock:
             _RENEWAL_INTERVAL_MS,
             self._server_name,
             self._store,
+            self._hs,
             self._clock,
             self._read_write,
             self._lock_name,
@@ -421,6 +425,7 @@ class Lock:
     def _renew(
         server_name: str,
         store: LockStore,
+        hs: "HomeServer",
         clock: Clock,
         read_write: bool,
         lock_name: str,
@@ -457,9 +462,8 @@ class Lock:
                 desc="renew_lock",
             )
 
-        return run_as_background_process(
+        return hs.run_as_background_process(
             "Lock._renew",
-            server_name,
             _internal_renew,
             store,
             clock,
@@ -493,9 +497,9 @@ class Lock:
 
     async def __aexit__(
         self,
-        _exctype: Optional[Type[BaseException]],
-        _excinst: Optional[BaseException],
-        _exctb: Optional[TracebackType],
+        _exctype: type[BaseException] | None,
+        _excinst: BaseException | None,
+        _exctb: TracebackType | None,
     ) -> bool:
         await self.release()
 
diff --git a/synapse/storage/databases/main/media_repository.py b/synapse/storage/databases/main/media_repository.py
index f726846e57..50664d63e5 100644
--- a/synapse/storage/databases/main/media_repository.py
+++ b/synapse/storage/databases/main/media_repository.py
@@ -25,10 +25,6 @@ from typing import (
     TYPE_CHECKING,
     Collection,
     Iterable,
-    List,
-    Optional,
-    Tuple,
-    Union,
     cast,
 )
 
@@ -59,16 +55,16 @@ logger = logging.getLogger(__name__)
 class LocalMedia:
     media_id: str
     media_type: str
-    media_length: Optional[int]
+    media_length: int | None
     upload_name: str
     created_ts: int
-    url_cache: Optional[str]
+    url_cache: str | None
     last_access_ts: int
-    quarantined_by: Optional[str]
+    quarantined_by: str | None
     safe_from_quarantine: bool
-    user_id: Optional[str]
-    authenticated: Optional[bool]
-    sha256: Optional[str]
+    user_id: str | None
+    authenticated: bool | None
+    sha256: str | None
 
 
 @attr.s(slots=True, frozen=True, auto_attribs=True)
@@ -77,20 +73,20 @@ class RemoteMedia:
     media_id: str
     media_type: str
     media_length: int
-    upload_name: Optional[str]
+    upload_name: str | None
     filesystem_id: str
     created_ts: int
     last_access_ts: int
-    quarantined_by: Optional[str]
-    authenticated: Optional[bool]
-    sha256: Optional[str]
+    quarantined_by: str | None
+    authenticated: bool | None
+    sha256: str | None
 
 
 @attr.s(slots=True, frozen=True, auto_attribs=True)
 class UrlCache:
     response_code: int
     expires_ts: int
-    og: Union[str, bytes]
+    og: str | bytes
 
 
 class MediaSortOrder(Enum):
@@ -185,7 +181,7 @@ class MediaRepositoryBackgroundUpdateStore(SQLBaseStore):
         )
 
         if hs.config.media.can_load_media_repo:
-            self.unused_expiration_time: Optional[int] = (
+            self.unused_expiration_time: int | None = (
                 hs.config.media.unused_expiration_time
             )
         else:
@@ -226,7 +222,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
         super().__init__(database, db_conn, hs)
         self.server_name: str = hs.hostname
 
-    async def get_local_media(self, media_id: str) -> Optional[LocalMedia]:
+    async def get_local_media(self, media_id: str) -> LocalMedia | None:
         """Get the metadata for a local piece of media
 
         Returns:
@@ -275,7 +271,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
         user_id: str,
         order_by: str = MediaSortOrder.CREATED_TS.value,
         direction: Direction = Direction.FORWARDS,
-    ) -> Tuple[List[LocalMedia], int]:
+    ) -> tuple[list[LocalMedia], int]:
         """Get a paginated list of metadata for a local piece of media
         which an user_id has uploaded
 
@@ -292,7 +288,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
 
         def get_local_media_by_user_paginate_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[List[LocalMedia], int]:
+        ) -> tuple[list[LocalMedia], int]:
             # Set ordering
             order_by_column = MediaSortOrder(order_by).value
 
@@ -301,14 +297,14 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
             else:
                 order = "ASC"
 
-            args: List[Union[str, int]] = [user_id]
+            args: list[str | int] = [user_id]
             sql = """
                 SELECT COUNT(*) as total_media
                 FROM local_media_repository
                 WHERE user_id = ?
             """
             txn.execute(sql, args)
-            count = cast(Tuple[int], txn.fetchone())[0]
+            count = cast(tuple[int], txn.fetchone())[0]
 
             sql = """
                 SELECT
@@ -365,7 +361,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
         keep_profiles: bool,
         include_quarantined_media: bool,
         include_protected_media: bool,
-    ) -> List[str]:
+    ) -> list[str]:
         """
         Retrieve a list of media IDs from the local media store.
 
@@ -437,7 +433,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
                 AND NOT safe_from_quarantine
             """
 
-        def _get_local_media_ids_txn(txn: LoggingTransaction) -> List[str]:
+        def _get_local_media_ids_txn(txn: LoggingTransaction) -> list[str]:
             txn.execute(sql, (before_ts, before_ts, size_gt))
             return [row[0] for row in txn]
 
@@ -474,12 +470,12 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
         media_id: str,
         media_type: str,
         time_now_ms: int,
-        upload_name: Optional[str],
+        upload_name: str | None,
         media_length: int,
         user_id: UserID,
-        url_cache: Optional[str] = None,
-        sha256: Optional[str] = None,
-        quarantined_by: Optional[str] = None,
+        url_cache: str | None = None,
+        sha256: str | None = None,
+        quarantined_by: str | None = None,
     ) -> None:
         if self.hs.config.media.enable_authenticated_media:
             authenticated = True
@@ -507,12 +503,12 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
         self,
         media_id: str,
         media_type: str,
-        upload_name: Optional[str],
+        upload_name: str | None,
         media_length: int,
         user_id: UserID,
         sha256: str,
-        url_cache: Optional[str] = None,
-        quarantined_by: Optional[str] = None,
+        url_cache: str | None = None,
+        quarantined_by: str | None = None,
     ) -> None:
         updatevalues = {
             "media_type": media_type,
@@ -544,7 +540,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
             desc="mark_local_media_as_safe",
         )
 
-    async def count_pending_media(self, user_id: UserID) -> Tuple[int, int]:
+    async def count_pending_media(self, user_id: UserID) -> tuple[int, int]:
         """Count the number of pending media for a user.
 
         Returns:
@@ -552,7 +548,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
             expiration timestamp.
         """
 
-        def get_pending_media_txn(txn: LoggingTransaction) -> Tuple[int, int]:
+        def get_pending_media_txn(txn: LoggingTransaction) -> tuple[int, int]:
             sql = """
             SELECT COUNT(*), MIN(created_ts)
             FROM local_media_repository
@@ -565,7 +561,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
                 sql,
                 (
                     user_id.to_string(),
-                    self._clock.time_msec() - self.unused_expiration_time,
+                    self.clock.time_msec() - self.unused_expiration_time,
                 ),
             )
             row = txn.fetchone()
@@ -577,13 +573,13 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
             "get_pending_media", get_pending_media_txn
         )
 
-    async def get_url_cache(self, url: str, ts: int) -> Optional[UrlCache]:
+    async def get_url_cache(self, url: str, ts: int) -> UrlCache | None:
         """Get the media_id and ts for a cached URL as of the given timestamp
         Returns:
             None if the URL isn't cached.
         """
 
-        def get_url_cache_txn(txn: LoggingTransaction) -> Optional[UrlCache]:
+        def get_url_cache_txn(txn: LoggingTransaction) -> UrlCache | None:
             # get the most recently cached result (relative to the given ts)
             sql = """
                 SELECT response_code, expires_ts, og
@@ -617,7 +613,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
         self,
         url: str,
         response_code: int,
-        etag: Optional[str],
+        etag: str | None,
         expires_ts: int,
         og: str,
         media_id: str,
@@ -637,9 +633,9 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
             desc="store_url_cache",
         )
 
-    async def get_local_media_thumbnails(self, media_id: str) -> List[ThumbnailInfo]:
+    async def get_local_media_thumbnails(self, media_id: str) -> list[ThumbnailInfo]:
         rows = cast(
-            List[Tuple[int, int, str, str, int]],
+            list[tuple[int, int, str, str, int]],
             await self.db_pool.simple_select_list(
                 "local_media_repository_thumbnails",
                 {"media_id": media_id},
@@ -685,7 +681,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
 
     async def get_cached_remote_media(
         self, origin: str, media_id: str
-    ) -> Optional[RemoteMedia]:
+    ) -> RemoteMedia | None:
         row = await self.db_pool.simple_select_one(
             "remote_media_cache",
             {"media_origin": origin, "media_id": media_id},
@@ -726,9 +722,9 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
         media_type: str,
         media_length: int,
         time_now_ms: int,
-        upload_name: Optional[str],
+        upload_name: str | None,
         filesystem_id: str,
-        sha256: Optional[str],
+        sha256: str | None,
     ) -> None:
         if self.hs.config.media.enable_authenticated_media:
             authenticated = True
@@ -755,7 +751,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
     async def update_cached_last_access_time(
         self,
         local_media: Iterable[str],
-        remote_media: Iterable[Tuple[str, str]],
+        remote_media: Iterable[tuple[str, str]],
         time_ms: int,
     ) -> None:
         """Updates the last access time of the given media
@@ -793,9 +789,9 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
 
     async def get_remote_media_thumbnails(
         self, origin: str, media_id: str
-    ) -> List[ThumbnailInfo]:
+    ) -> list[ThumbnailInfo]:
         rows = cast(
-            List[Tuple[int, int, str, str, int]],
+            list[tuple[int, int, str, str, int]],
             await self.db_pool.simple_select_list(
                 "remote_media_cache_thumbnails",
                 {"media_origin": origin, "media_id": media_id},
@@ -824,7 +820,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
         t_width: int,
         t_height: int,
         t_type: str,
-    ) -> Optional[ThumbnailInfo]:
+    ) -> ThumbnailInfo | None:
         """Fetch the thumbnail info of given width, height and type."""
 
         row = await self.db_pool.simple_select_one(
@@ -881,7 +877,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
 
     async def get_remote_media_ids(
         self, before_ts: int, include_quarantined_media: bool
-    ) -> List[Tuple[str, str, str]]:
+    ) -> list[tuple[str, str, str]]:
         """
         Retrieve a list of server name, media ID tuples from the remote media cache.
 
@@ -911,7 +907,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
             """
 
         return cast(
-            List[Tuple[str, str, str]],
+            list[tuple[str, str, str]],
             await self.db_pool.execute("get_remote_media_ids", sql, before_ts),
         )
 
@@ -932,7 +928,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
             "delete_remote_media", delete_remote_media_txn
         )
 
-    async def get_expired_url_cache(self, now_ts: int) -> List[str]:
+    async def get_expired_url_cache(self, now_ts: int) -> list[str]:
         sql = (
             "SELECT media_id FROM local_media_repository_url_cache"
             " WHERE expires_ts < ?"
@@ -940,7 +936,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
             " LIMIT 500"
         )
 
-        def _get_expired_url_cache_txn(txn: LoggingTransaction) -> List[str]:
+        def _get_expired_url_cache_txn(txn: LoggingTransaction) -> list[str]:
             txn.execute(sql, (now_ts,))
             return [row[0] for row in txn]
 
@@ -959,7 +955,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
 
         await self.db_pool.runInteraction("delete_url_cache", _delete_url_cache_txn)
 
-    async def get_url_cache_media_before(self, before_ts: int) -> List[str]:
+    async def get_url_cache_media_before(self, before_ts: int) -> list[str]:
         sql = (
             "SELECT media_id FROM local_media_repository"
             " WHERE created_ts < ? AND url_cache IS NOT NULL"
@@ -967,7 +963,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
             " LIMIT 500"
         )
 
-        def _get_url_cache_media_before_txn(txn: LoggingTransaction) -> List[str]:
+        def _get_url_cache_media_before_txn(txn: LoggingTransaction) -> list[str]:
             txn.execute(sql, (before_ts,))
             return [row[0] for row in txn]
 
@@ -1059,7 +1055,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
             txn: LoggingTransaction,
         ) -> int:
             # Calculate the timestamp for the start of the time period
-            start_ts = self._clock.time_msec() - time_period_ms
+            start_ts = self.clock.time_msec() - time_period_ms
             txn.execute(sql, (user_id, start_ts))
             row = txn.fetchone()
             if row is None:
diff --git a/synapse/storage/databases/main/metrics.py b/synapse/storage/databases/main/metrics.py
index a3467bff3d..dc8e2c1616 100644
--- a/synapse/storage/databases/main/metrics.py
+++ b/synapse/storage/databases/main/metrics.py
@@ -21,7 +21,7 @@
 import calendar
 import logging
 import time
-from typing import TYPE_CHECKING, Dict, List, Tuple, cast
+from typing import TYPE_CHECKING, cast
 
 from synapse.metrics import SERVER_NAME_LABEL, GaugeBucketCollector
 from synapse.metrics.background_process_metrics import wrap_as_background_process
@@ -78,14 +78,14 @@ class ServerMetricsStore(EventPushActionsWorkerStore, SQLBaseStore):
 
         # Read the extrems every 60 minutes
         if hs.config.worker.run_background_tasks:
-            self._clock.looping_call(self._read_forward_extremities, 60 * 60 * 1000)
+            self.clock.looping_call(self._read_forward_extremities, 60 * 60 * 1000)
 
         # Used in _generate_user_daily_visits to keep track of progress
         self._last_user_visit_update = self._get_start_of_day()
 
     @wrap_as_background_process("read_forward_extremities")
     async def _read_forward_extremities(self) -> None:
-        def fetch(txn: LoggingTransaction) -> List[Tuple[int, int]]:
+        def fetch(txn: LoggingTransaction) -> list[tuple[int, int]]:
             txn.execute(
                 """
                 SELECT t1.c, t2.c
@@ -98,7 +98,7 @@ class ServerMetricsStore(EventPushActionsWorkerStore, SQLBaseStore):
                 ) t2 ON t1.room_id = t2.room_id
                 """
             )
-            return cast(List[Tuple[int, int]], txn.fetchall())
+            return cast(list[tuple[int, int]], txn.fetchall())
 
         res = await self.db_pool.runInteraction("read_forward_extremities", fetch)
 
@@ -125,7 +125,7 @@ class ServerMetricsStore(EventPushActionsWorkerStore, SQLBaseStore):
                 AND stream_ordering > ?
             """
             txn.execute(sql, (self.stream_ordering_day_ago,))
-            (count,) = cast(Tuple[int], txn.fetchone())
+            (count,) = cast(tuple[int], txn.fetchone())
             return count
 
         return await self.db_pool.runInteraction("count_e2ee_messages", _count_messages)
@@ -144,7 +144,7 @@ class ServerMetricsStore(EventPushActionsWorkerStore, SQLBaseStore):
             """
 
             txn.execute(sql, (like_clause, self.stream_ordering_day_ago))
-            (count,) = cast(Tuple[int], txn.fetchone())
+            (count,) = cast(tuple[int], txn.fetchone())
             return count
 
         return await self.db_pool.runInteraction(
@@ -159,7 +159,7 @@ class ServerMetricsStore(EventPushActionsWorkerStore, SQLBaseStore):
                 AND stream_ordering > ?
             """
             txn.execute(sql, (self.stream_ordering_day_ago,))
-            (count,) = cast(Tuple[int], txn.fetchone())
+            (count,) = cast(tuple[int], txn.fetchone())
             return count
 
         return await self.db_pool.runInteraction(
@@ -181,7 +181,7 @@ class ServerMetricsStore(EventPushActionsWorkerStore, SQLBaseStore):
                 AND stream_ordering > ?
             """
             txn.execute(sql, (self.stream_ordering_day_ago,))
-            (count,) = cast(Tuple[int], txn.fetchone())
+            (count,) = cast(tuple[int], txn.fetchone())
             return count
 
         return await self.db_pool.runInteraction("count_messages", _count_messages)
@@ -200,7 +200,7 @@ class ServerMetricsStore(EventPushActionsWorkerStore, SQLBaseStore):
             """
 
             txn.execute(sql, (like_clause, self.stream_ordering_day_ago))
-            (count,) = cast(Tuple[int], txn.fetchone())
+            (count,) = cast(tuple[int], txn.fetchone())
             return count
 
         return await self.db_pool.runInteraction(
@@ -215,7 +215,7 @@ class ServerMetricsStore(EventPushActionsWorkerStore, SQLBaseStore):
                 AND stream_ordering > ?
             """
             txn.execute(sql, (self.stream_ordering_day_ago,))
-            (count,) = cast(Tuple[int], txn.fetchone())
+            (count,) = cast(tuple[int], txn.fetchone())
             return count
 
         return await self.db_pool.runInteraction("count_daily_active_rooms", _count)
@@ -224,7 +224,7 @@ class ServerMetricsStore(EventPushActionsWorkerStore, SQLBaseStore):
         """
         Counts the number of users who used this homeserver in the last 24 hours.
         """
-        yesterday = int(self._clock.time_msec()) - (1000 * 60 * 60 * 24)
+        yesterday = int(self.clock.time_msec()) - (1000 * 60 * 60 * 24)
         return await self.db_pool.runInteraction(
             "count_daily_users", self._count_users, yesterday
         )
@@ -236,7 +236,7 @@ class ServerMetricsStore(EventPushActionsWorkerStore, SQLBaseStore):
         from the mau figure in synapse.storage.monthly_active_users which,
         amongst other things, includes a 3 day grace period before a user counts.
         """
-        thirty_days_ago = int(self._clock.time_msec()) - (1000 * 60 * 60 * 24 * 30)
+        thirty_days_ago = int(self.clock.time_msec()) - (1000 * 60 * 60 * 24 * 30)
         return await self.db_pool.runInteraction(
             "count_monthly_users", self._count_users, thirty_days_ago
         )
@@ -256,10 +256,10 @@ class ServerMetricsStore(EventPushActionsWorkerStore, SQLBaseStore):
         # Mypy knows that fetchone() might return None if there are no rows.
         # We know better: "SELECT COUNT(...) FROM ..." without any GROUP BY always
         # returns exactly one row.
-        (count,) = cast(Tuple[int], txn.fetchone())
+        (count,) = cast(tuple[int], txn.fetchone())
         return count
 
-    async def count_r30v2_users(self) -> Dict[str, int]:
+    async def count_r30v2_users(self) -> dict[str, int]:
         """
         Counts the number of 30 day retained users, defined as users that:
          - Appear more than once in the past 60 days
@@ -279,9 +279,9 @@ class ServerMetricsStore(EventPushActionsWorkerStore, SQLBaseStore):
               - "web" (any web application -- it's not possible to distinguish Element Web here)
         """
 
-        def _count_r30v2_users(txn: LoggingTransaction) -> Dict[str, int]:
+        def _count_r30v2_users(txn: LoggingTransaction) -> dict[str, int]:
             thirty_days_in_secs = 86400 * 30
-            now = int(self._clock.time())
+            now = int(self.clock.time())
             sixty_days_ago_in_secs = now - 2 * thirty_days_in_secs
             one_day_from_now_in_secs = now + 86400
 
@@ -376,7 +376,7 @@ class ServerMetricsStore(EventPushActionsWorkerStore, SQLBaseStore):
                     thirty_days_in_secs * 1000,
                 ),
             )
-            (count,) = cast(Tuple[int], txn.fetchone())
+            (count,) = cast(tuple[int], txn.fetchone())
             results["all"] = count
 
             return results
@@ -389,7 +389,7 @@ class ServerMetricsStore(EventPushActionsWorkerStore, SQLBaseStore):
         """
         Returns millisecond unixtime for start of UTC day.
         """
-        now = time.gmtime(self._clock.time())
+        now = time.gmtime(self.clock.time())
         today_start = calendar.timegm((now.tm_year, now.tm_mon, now.tm_mday, 0, 0, 0))
         return today_start * 1000
 
@@ -403,7 +403,7 @@ class ServerMetricsStore(EventPushActionsWorkerStore, SQLBaseStore):
             logger.info("Calling _generate_user_daily_visits")
             today_start = self._get_start_of_day()
             a_day_in_milliseconds = 24 * 60 * 60 * 1000
-            now = self._clock.time_msec()
+            now = self.clock.time_msec()
 
             # A note on user_agent. Technically a given device can have multiple
             # user agents, so we need to decide which one to pick. We could have
diff --git a/synapse/storage/databases/main/monthly_active_users.py b/synapse/storage/databases/main/monthly_active_users.py
index f5a6b98be7..b51edd5d0c 100644
--- a/synapse/storage/databases/main/monthly_active_users.py
+++ b/synapse/storage/databases/main/monthly_active_users.py
@@ -18,7 +18,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, Dict, List, Mapping, Optional, Tuple, cast
+from typing import TYPE_CHECKING, Mapping, cast
 
 from synapse.metrics.background_process_metrics import wrap_as_background_process
 from synapse.storage.database import (
@@ -49,7 +49,6 @@ class MonthlyActiveUsersWorkerStore(RegistrationWorkerStore):
         hs: "HomeServer",
     ):
         super().__init__(database, db_conn, hs)
-        self._clock = hs.get_clock()
         self.hs = hs
 
         if hs.config.redis.redis_enabled:
@@ -95,7 +94,7 @@ class MonthlyActiveUsersWorkerStore(RegistrationWorkerStore):
                 WHERE (users.appservice_id IS NULL OR users.appservice_id = '');
             """
             txn.execute(sql)
-            (count,) = cast(Tuple[int], txn.fetchone())
+            (count,) = cast(tuple[int], txn.fetchone())
             return count
 
         return await self.db_pool.runInteraction("count_users", _count_users)
@@ -113,7 +112,7 @@ class MonthlyActiveUsersWorkerStore(RegistrationWorkerStore):
 
         """
 
-        def _count_users_by_service(txn: LoggingTransaction) -> Dict[str, int]:
+        def _count_users_by_service(txn: LoggingTransaction) -> dict[str, int]:
             sql = """
                 SELECT COALESCE(appservice_id, 'native'), COUNT(*)
                 FROM monthly_active_users
@@ -122,7 +121,7 @@ class MonthlyActiveUsersWorkerStore(RegistrationWorkerStore):
             """
 
             txn.execute(sql)
-            result = cast(List[Tuple[str, int]], txn.fetchall())
+            result = cast(list[tuple[str, int]], txn.fetchall())
             return dict(result)
 
         return await self.db_pool.runInteraction(
@@ -130,8 +129,8 @@ class MonthlyActiveUsersWorkerStore(RegistrationWorkerStore):
         )
 
     async def get_monthly_active_users_by_service(
-        self, start_timestamp: Optional[int] = None, end_timestamp: Optional[int] = None
-    ) -> List[Tuple[str, str]]:
+        self, start_timestamp: int | None = None, end_timestamp: int | None = None
+    ) -> list[tuple[str, str]]:
         """Generates list of monthly active users and their services.
         Please see "get_monthly_active_count_by_service" docstring for more details
         about services.
@@ -161,7 +160,7 @@ class MonthlyActiveUsersWorkerStore(RegistrationWorkerStore):
             where_clause = ""
             query_params = []
 
-        def _list_users(txn: LoggingTransaction) -> List[Tuple[str, str]]:
+        def _list_users(txn: LoggingTransaction) -> list[tuple[str, str]]:
             sql = f"""
                     SELECT COALESCE(appservice_id, 'native'), user_id
                     FROM monthly_active_users
@@ -170,11 +169,11 @@ class MonthlyActiveUsersWorkerStore(RegistrationWorkerStore):
                 """
 
             txn.execute(sql, query_params)
-            return cast(List[Tuple[str, str]], txn.fetchall())
+            return cast(list[tuple[str, str]], txn.fetchall())
 
         return await self.db_pool.runInteraction("list_users", _list_users)
 
-    async def get_registered_reserved_users(self) -> List[str]:
+    async def get_registered_reserved_users(self) -> list[str]:
         """Of the reserved threepids defined in config, retrieve those that are associated
         with registered users
 
@@ -195,7 +194,7 @@ class MonthlyActiveUsersWorkerStore(RegistrationWorkerStore):
         return users
 
     @cached(num_args=1)
-    async def user_last_seen_monthly_active(self, user_id: str) -> Optional[int]:
+    async def user_last_seen_monthly_active(self, user_id: str) -> int | None:
         """
         Checks if a given user is part of the monthly active user group
 
@@ -220,13 +219,13 @@ class MonthlyActiveUsersWorkerStore(RegistrationWorkerStore):
         entries exist.
         """
 
-        def _reap_users(txn: LoggingTransaction, reserved_users: List[str]) -> None:
+        def _reap_users(txn: LoggingTransaction, reserved_users: list[str]) -> None:
             """
             Args:
                 reserved_users: reserved users to preserve
             """
 
-            thirty_days_ago = int(self._clock.time_msec()) - (1000 * 60 * 60 * 24 * 30)
+            thirty_days_ago = int(self.clock.time_msec()) - (1000 * 60 * 60 * 24 * 30)
 
             in_clause, in_clause_args = make_in_list_sql_clause(
                 self.database_engine, "user_id", reserved_users
@@ -295,7 +294,7 @@ class MonthlyActiveUsersWorkerStore(RegistrationWorkerStore):
         )
 
     def _initialise_reserved_users(
-        self, txn: LoggingTransaction, threepids: List[dict]
+        self, txn: LoggingTransaction, threepids: list[dict]
     ) -> None:
         """Ensures that reserved threepids are accounted for in the MAU table, should
         be called on start up.
@@ -328,7 +327,7 @@ class MonthlyActiveUsersWorkerStore(RegistrationWorkerStore):
                         txn,
                         table="monthly_active_users",
                         keyvalues={"user_id": user_id},
-                        values={"timestamp": int(self._clock.time_msec())},
+                        values={"timestamp": int(self.clock.time_msec())},
                     )
             else:
                 logger.warning("mau limit reserved threepid %s not found in db", tp)
@@ -391,7 +390,7 @@ class MonthlyActiveUsersWorkerStore(RegistrationWorkerStore):
             txn,
             table="monthly_active_users",
             keyvalues={"user_id": user_id},
-            values={"timestamp": int(self._clock.time_msec())},
+            values={"timestamp": int(self.clock.time_msec())},
         )
 
         self._invalidate_cache_and_stream(txn, self.get_monthly_active_count, ())
diff --git a/synapse/storage/databases/main/openid.py b/synapse/storage/databases/main/openid.py
index 0db7f73730..15c47a2562 100644
--- a/synapse/storage/databases/main/openid.py
+++ b/synapse/storage/databases/main/openid.py
@@ -19,7 +19,6 @@
 #
 #
 
-from typing import Optional
 
 from synapse.storage._base import SQLBaseStore
 from synapse.storage.database import LoggingTransaction
@@ -41,8 +40,8 @@ class OpenIdStore(SQLBaseStore):
 
     async def get_user_id_for_open_id_token(
         self, token: str, ts_now_ms: int
-    ) -> Optional[str]:
-        def get_user_id_for_token_txn(txn: LoggingTransaction) -> Optional[str]:
+    ) -> str | None:
+        def get_user_id_for_token_txn(txn: LoggingTransaction) -> str | None:
             sql = (
                 "SELECT user_id FROM open_id_tokens"
                 " WHERE token = ? AND ? <= ts_valid_until_ms"
diff --git a/synapse/storage/databases/main/presence.py b/synapse/storage/databases/main/presence.py
index 587f51df2c..75ca9e40d7 100644
--- a/synapse/storage/databases/main/presence.py
+++ b/synapse/storage/databases/main/presence.py
@@ -21,13 +21,8 @@
 from typing import (
     TYPE_CHECKING,
     Any,
-    Dict,
     Iterable,
-    List,
     Mapping,
-    Optional,
-    Tuple,
-    Union,
     cast,
 )
 
@@ -116,8 +111,8 @@ class PresenceStore(PresenceBackgroundUpdateStore, CacheInvalidationWorkerStore)
         )
 
     async def update_presence(
-        self, presence_states: List[UserPresenceState]
-    ) -> Tuple[int, int]:
+        self, presence_states: list[UserPresenceState]
+    ) -> tuple[int, int]:
         assert self._can_persist_presence
 
         stream_ordering_manager = self._presence_id_gen.get_next_mult(
@@ -142,8 +137,8 @@ class PresenceStore(PresenceBackgroundUpdateStore, CacheInvalidationWorkerStore)
     def _update_presence_txn(
         self,
         txn: LoggingTransaction,
-        stream_orderings: List[int],
-        presence_states: List[UserPresenceState],
+        stream_orderings: list[int],
+        presence_states: list[UserPresenceState],
     ) -> None:
         for stream_id, state in zip(stream_orderings, presence_states):
             txn.call_after(
@@ -193,7 +188,7 @@ class PresenceStore(PresenceBackgroundUpdateStore, CacheInvalidationWorkerStore)
 
     async def get_all_presence_updates(
         self, instance_name: str, last_id: int, current_id: int, limit: int
-    ) -> Tuple[List[Tuple[int, list]], int, bool]:
+    ) -> tuple[list[tuple[int, list]], int, bool]:
         """Get updates for presence replication stream.
 
         Args:
@@ -220,7 +215,7 @@ class PresenceStore(PresenceBackgroundUpdateStore, CacheInvalidationWorkerStore)
 
         def get_all_presence_updates_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[List[Tuple[int, list]], int, bool]:
+        ) -> tuple[list[tuple[int, list]], int, bool]:
             sql = """
                 SELECT stream_id, user_id, state, last_active_ts,
                     last_federation_update_ts, last_user_sync_ts,
@@ -232,7 +227,7 @@ class PresenceStore(PresenceBackgroundUpdateStore, CacheInvalidationWorkerStore)
             """
             txn.execute(sql, (last_id, current_id, limit))
             updates = cast(
-                List[Tuple[int, list]],
+                list[tuple[int, list]],
                 [(row[0], row[1:]) for row in txn],
             )
 
@@ -263,7 +258,7 @@ class PresenceStore(PresenceBackgroundUpdateStore, CacheInvalidationWorkerStore)
         # TODO All these columns are nullable, but we don't expect that:
         #      https://github.com/matrix-org/synapse/issues/16467
         rows = cast(
-            List[Tuple[str, str, int, int, int, Optional[str], Union[int, bool]]],
+            list[tuple[str, str, int, int, int, str | None, int | bool]],
             await self.db_pool.simple_select_many_batch(
                 table="presence_stream",
                 column="user_id",
@@ -320,7 +315,7 @@ class PresenceStore(PresenceBackgroundUpdateStore, CacheInvalidationWorkerStore)
     @cached()
     async def _get_full_presence_stream_token_for_user(
         self, user_id: str
-    ) -> Optional[int]:
+    ) -> int | None:
         """Get the presence token corresponding to the last full presence update
         for this user.
 
@@ -375,7 +370,7 @@ class PresenceStore(PresenceBackgroundUpdateStore, CacheInvalidationWorkerStore)
     async def get_presence_for_all_users(
         self,
         include_offline: bool = True,
-    ) -> Dict[str, UserPresenceState]:
+    ) -> dict[str, UserPresenceState]:
         """Retrieve the current presence state for all users.
 
         Note that the presence_stream table is culled frequently, so it should only
@@ -402,7 +397,7 @@ class PresenceStore(PresenceBackgroundUpdateStore, CacheInvalidationWorkerStore)
             # TODO All these columns are nullable, but we don't expect that:
             #      https://github.com/matrix-org/synapse/issues/16467
             rows = cast(
-                List[Tuple[str, str, int, int, int, Optional[str], Union[int, bool]]],
+                list[tuple[str, str, int, int, int, str | None, int | bool]],
                 await self.db_pool.runInteraction(
                     "get_presence_for_all_users",
                     self.db_pool.simple_select_list_paginate_txn,
@@ -457,7 +452,7 @@ class PresenceStore(PresenceBackgroundUpdateStore, CacheInvalidationWorkerStore)
     def get_presence_stream_id_gen(self) -> MultiWriterIdGenerator:
         return self._presence_id_gen
 
-    def _get_active_presence(self, db_conn: Connection) -> List[UserPresenceState]:
+    def _get_active_presence(self, db_conn: Connection) -> list[UserPresenceState]:
         """Fetch non-offline presence from the database so that we can register
         the appropriate time outs.
         """
@@ -488,7 +483,7 @@ class PresenceStore(PresenceBackgroundUpdateStore, CacheInvalidationWorkerStore)
             for user_id, state, last_active_ts, last_federation_update_ts, last_user_sync_ts, status_msg, currently_active in rows
         ]
 
-    def take_presence_startup_info(self) -> List[UserPresenceState]:
+    def take_presence_startup_info(self) -> list[UserPresenceState]:
         active_on_startup = self._presence_on_startup
         self._presence_on_startup = []
         return active_on_startup
diff --git a/synapse/storage/databases/main/profile.py b/synapse/storage/databases/main/profile.py
index 30d8a58d96..11ad516eb3 100644
--- a/synapse/storage/databases/main/profile.py
+++ b/synapse/storage/databases/main/profile.py
@@ -19,7 +19,7 @@
 #
 #
 import json
-from typing import TYPE_CHECKING, Dict, Optional, Tuple, cast
+from typing import TYPE_CHECKING, cast
 
 from canonicaljson import encode_canonical_json
 
@@ -75,7 +75,7 @@ class ProfileWorkerStore(SQLBaseStore):
 
         lower_bound_id = progress.get("lower_bound_id", "")
 
-        def _get_last_id(txn: LoggingTransaction) -> Optional[str]:
+        def _get_last_id(txn: LoggingTransaction) -> str | None:
             sql = """
                     SELECT user_id FROM profiles
                     WHERE user_id > ?
@@ -176,7 +176,7 @@ class ProfileWorkerStore(SQLBaseStore):
 
         return ProfileInfo(avatar_url=profile[1], display_name=profile[0])
 
-    async def get_profile_displayname(self, user_id: UserID) -> Optional[str]:
+    async def get_profile_displayname(self, user_id: UserID) -> str | None:
         """
         Fetch the display name of a user.
 
@@ -193,7 +193,7 @@ class ProfileWorkerStore(SQLBaseStore):
             desc="get_profile_displayname",
         )
 
-    async def get_profile_avatar_url(self, user_id: UserID) -> Optional[str]:
+    async def get_profile_avatar_url(self, user_id: UserID) -> str | None:
         """
         Fetch the avatar URL of a user.
 
@@ -240,7 +240,7 @@ class ProfileWorkerStore(SQLBaseStore):
 
                 # Test exists first since value being None is used for both
                 # missing and a null JSON value.
-                exists, value = cast(Tuple[bool, JsonValue], txn.fetchone())
+                exists, value = cast(tuple[bool, JsonValue], txn.fetchone())
                 if not exists:
                     raise StoreError(404, "No row found")
                 return value
@@ -257,9 +257,7 @@ class ProfileWorkerStore(SQLBaseStore):
                 )
 
                 # If value_type is None, then the value did not exist.
-                value_type, value = cast(
-                    Tuple[Optional[str], JsonValue], txn.fetchone()
-                )
+                value_type, value = cast(tuple[str | None, JsonValue], txn.fetchone())
                 if not value_type:
                     raise StoreError(404, "No row found")
                 # If value_type is object or array, then need to deserialize the JSON.
@@ -271,7 +269,7 @@ class ProfileWorkerStore(SQLBaseStore):
 
         return await self.db_pool.runInteraction("get_profile_field", get_profile_field)
 
-    async def get_profile_fields(self, user_id: UserID) -> Dict[str, str]:
+    async def get_profile_fields(self, user_id: UserID) -> dict[str, str]:
         """
         Get all custom profile fields for a user.
 
@@ -346,7 +344,7 @@ class ProfileWorkerStore(SQLBaseStore):
                 # possible due to the grammar.
                 (f'$."{new_field_name}"', user_id.localpart),
             )
-        row = cast(Tuple[Optional[int], Optional[int], Optional[int]], txn.fetchone())
+        row = cast(tuple[int | None, int | None, int | None], txn.fetchone())
 
         # The values return null if the column is null.
         total_bytes = (
@@ -373,7 +371,7 @@ class ProfileWorkerStore(SQLBaseStore):
             raise StoreError(400, "Profile too large", Codes.PROFILE_TOO_LARGE)
 
     async def set_profile_displayname(
-        self, user_id: UserID, new_displayname: Optional[str]
+        self, user_id: UserID, new_displayname: str | None
     ) -> None:
         """
         Set the display name of a user.
@@ -406,7 +404,7 @@ class ProfileWorkerStore(SQLBaseStore):
         )
 
     async def set_profile_avatar_url(
-        self, user_id: UserID, new_avatar_url: Optional[str]
+        self, user_id: UserID, new_avatar_url: str | None
     ) -> None:
         """
         Set the avatar of a user.
diff --git a/synapse/storage/databases/main/purge_events.py b/synapse/storage/databases/main/purge_events.py
index d4642a1309..10de1b35a6 100644
--- a/synapse/storage/databases/main/purge_events.py
+++ b/synapse/storage/databases/main/purge_events.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import Any, Set, Tuple, cast
+from typing import Any, cast
 
 from synapse.api.errors import SynapseError
 from synapse.storage.database import LoggingTransaction
@@ -103,7 +103,7 @@ The tables with a `room_id` column regardless of whether they have a useful inde
 class PurgeEventsStore(StateGroupWorkerStore, CacheInvalidationWorkerStore):
     async def purge_history(
         self, room_id: str, token: str, delete_local_events: bool
-    ) -> Set[int]:
+    ) -> set[int]:
         """Deletes room history before a certain point.
 
         Note that only a single purge can occur at once, this is guaranteed via
@@ -137,7 +137,7 @@ class PurgeEventsStore(StateGroupWorkerStore, CacheInvalidationWorkerStore):
         room_id: str,
         token: RoomStreamToken,
         delete_local_events: bool,
-    ) -> Set[int]:
+    ) -> set[int]:
         # Tables that should be pruned:
         #     event_auth
         #     event_backward_extremities
@@ -204,7 +204,7 @@ class PurgeEventsStore(StateGroupWorkerStore, CacheInvalidationWorkerStore):
         logger.info("[purge] looking for events to delete")
 
         should_delete_expr = "state_events.state_key IS NULL"
-        should_delete_params: Tuple[Any, ...] = ()
+        should_delete_params: tuple[Any, ...] = ()
         if not delete_local_events:
             should_delete_expr += " AND event_id NOT LIKE ?"
 
@@ -355,7 +355,7 @@ class PurgeEventsStore(StateGroupWorkerStore, CacheInvalidationWorkerStore):
         """,
             (room_id,),
         )
-        (min_depth,) = cast(Tuple[int], txn.fetchone())
+        (min_depth,) = cast(tuple[int], txn.fetchone())
 
         logger.info("[purge] updating room_depth to %d", min_depth)
 
diff --git a/synapse/storage/databases/main/push_rule.py b/synapse/storage/databases/main/push_rule.py
index 1860be1713..d361166cec 100644
--- a/synapse/storage/databases/main/push_rule.py
+++ b/synapse/storage/databases/main/push_rule.py
@@ -23,14 +23,9 @@ from typing import (
     TYPE_CHECKING,
     Any,
     Collection,
-    Dict,
     Iterable,
-    List,
     Mapping,
-    Optional,
     Sequence,
-    Tuple,
-    Union,
     cast,
 )
 
@@ -69,8 +64,8 @@ logger = logging.getLogger(__name__)
 
 
 def _load_rules(
-    rawrules: List[Tuple[str, int, str, str]],
-    enabled_map: Dict[str, bool],
+    rawrules: list[tuple[str, int, str, str]],
+    enabled_map: dict[str, bool],
     experimental_config: ExperimentalConfig,
 ) -> FilteredPushRules:
     """Take the DB rows returned from the DB and convert them into a full
@@ -206,7 +201,7 @@ class PushRulesWorkerStore(
     @cached(max_entries=5000)
     async def get_push_rules_for_user(self, user_id: str) -> FilteredPushRules:
         rows = cast(
-            List[Tuple[str, int, int, str, str]],
+            list[tuple[str, int, int, str, str]],
             await self.db_pool.simple_select_list(
                 table="push_rules",
                 keyvalues={"user_name": user_id},
@@ -232,9 +227,9 @@ class PushRulesWorkerStore(
             self.hs.config.experimental,
         )
 
-    async def get_push_rules_enabled_for_user(self, user_id: str) -> Dict[str, bool]:
+    async def get_push_rules_enabled_for_user(self, user_id: str) -> dict[str, bool]:
         results = cast(
-            List[Tuple[str, Optional[Union[int, bool]]]],
+            list[tuple[str, int | bool | None]],
             await self.db_pool.simple_select_list(
                 table="push_rules_enable",
                 keyvalues={"user_name": user_id},
@@ -257,7 +252,7 @@ class PushRulesWorkerStore(
                     " WHERE user_id = ? AND ? < stream_id"
                 )
                 txn.execute(sql, (user_id, last_id))
-                (count,) = cast(Tuple[int], txn.fetchone())
+                (count,) = cast(tuple[int], txn.fetchone())
                 return bool(count)
 
             return await self.db_pool.runInteraction(
@@ -271,7 +266,7 @@ class PushRulesWorkerStore(
         if not user_ids:
             return {}
 
-        raw_rules: Dict[str, List[Tuple[str, int, str, str]]] = {
+        raw_rules: dict[str, list[tuple[str, int, str, str]]] = {
             user_id: [] for user_id in user_ids
         }
 
@@ -280,7 +275,7 @@ class PushRulesWorkerStore(
             gather_results(
                 (
                     cast(
-                        "defer.Deferred[List[Tuple[str, str, int, int, str, str]]]",
+                        "defer.Deferred[list[tuple[str, str, int, int, str, str]]]",
                         run_in_background(
                             self.db_pool.simple_select_many_batch,
                             table="push_rules",
@@ -312,7 +307,7 @@ class PushRulesWorkerStore(
                 (rule_id, priority_class, conditions, actions)
             )
 
-        results: Dict[str, FilteredPushRules] = {}
+        results: dict[str, FilteredPushRules] = {}
 
         for user_id, rules in raw_rules.items():
             results[user_id] = _load_rules(
@@ -323,14 +318,14 @@ class PushRulesWorkerStore(
 
     async def bulk_get_push_rules_enabled(
         self, user_ids: Collection[str]
-    ) -> Dict[str, Dict[str, bool]]:
+    ) -> dict[str, dict[str, bool]]:
         if not user_ids:
             return {}
 
-        results: Dict[str, Dict[str, bool]] = {user_id: {} for user_id in user_ids}
+        results: dict[str, dict[str, bool]] = {user_id: {} for user_id in user_ids}
 
         rows = cast(
-            List[Tuple[str, str, Optional[int]]],
+            list[tuple[str, str, int | None]],
             await self.db_pool.simple_select_many_batch(
                 table="push_rules_enable",
                 column="user_name",
@@ -346,7 +341,7 @@ class PushRulesWorkerStore(
 
     async def get_all_push_rule_updates(
         self, instance_name: str, last_id: int, current_id: int, limit: int
-    ) -> Tuple[List[Tuple[int, Tuple[str]]], int, bool]:
+    ) -> tuple[list[tuple[int, tuple[str]]], int, bool]:
         """Get updates for push_rules replication stream.
 
         Args:
@@ -373,7 +368,7 @@ class PushRulesWorkerStore(
 
         def get_all_push_rule_updates_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[List[Tuple[int, Tuple[str]]], int, bool]:
+        ) -> tuple[list[tuple[int, tuple[str]]], int, bool]:
             sql = """
                 SELECT stream_id, user_id
                 FROM push_rules_stream
@@ -383,7 +378,7 @@ class PushRulesWorkerStore(
             """
             txn.execute(sql, (last_id, current_id, limit))
             updates = cast(
-                List[Tuple[int, Tuple[str]]],
+                list[tuple[int, tuple[str]]],
                 [(stream_id, (user_id,)) for stream_id, user_id in txn],
             )
 
@@ -405,9 +400,9 @@ class PushRulesWorkerStore(
         rule_id: str,
         priority_class: int,
         conditions: Sequence[Mapping[str, str]],
-        actions: Sequence[Union[Mapping[str, Any], str]],
-        before: Optional[str] = None,
-        after: Optional[str] = None,
+        actions: Sequence[Mapping[str, Any] | str],
+        before: str | None = None,
+        after: str | None = None,
     ) -> None:
         if not self._is_push_writer:
             raise Exception("Not a push writer")
@@ -794,7 +789,7 @@ class PushRulesWorkerStore(
         self,
         user_id: str,
         rule_id: str,
-        actions: List[Union[dict, str]],
+        actions: list[dict | str],
         is_default_rule: bool,
     ) -> None:
         """
@@ -885,7 +880,7 @@ class PushRulesWorkerStore(
         user_id: str,
         rule_id: str,
         op: str,
-        data: Optional[JsonDict] = None,
+        data: JsonDict | None = None,
     ) -> None:
         if not self._is_push_writer:
             raise Exception("Not a push writer")
diff --git a/synapse/storage/databases/main/pusher.py b/synapse/storage/databases/main/pusher.py
index 1b2aa79ab1..e7ab7f64f9 100644
--- a/synapse/storage/databases/main/pusher.py
+++ b/synapse/storage/databases/main/pusher.py
@@ -23,12 +23,8 @@ import logging
 from typing import (
     TYPE_CHECKING,
     Any,
-    Dict,
     Iterable,
     Iterator,
-    List,
-    Optional,
-    Tuple,
     cast,
 )
 
@@ -51,10 +47,10 @@ if TYPE_CHECKING:
 logger = logging.getLogger(__name__)
 
 # The type of a row in the pushers table.
-PusherRow = Tuple[
+PusherRow = tuple[
     int,  # id
     str,  # user_name
-    Optional[int],  # access_token
+    int | None,  # access_token
     str,  # profile_tag
     str,  # kind
     str,  # app_id
@@ -192,7 +188,7 @@ class PusherWorkerStore(SQLBaseStore):
     async def get_pushers_by_user_id(self, user_id: str) -> Iterator[PusherConfig]:
         return await self.get_pushers_by({"user_name": user_id})
 
-    async def get_pushers_by(self, keyvalues: Dict[str, Any]) -> Iterator[PusherConfig]:
+    async def get_pushers_by(self, keyvalues: dict[str, Any]) -> Iterator[PusherConfig]:
         """Retrieve pushers that match the given criteria.
 
         Args:
@@ -202,7 +198,7 @@ class PusherWorkerStore(SQLBaseStore):
             The pushers for which the given columns have the given values.
         """
 
-        def get_pushers_by_txn(txn: LoggingTransaction) -> List[PusherRow]:
+        def get_pushers_by_txn(txn: LoggingTransaction) -> list[PusherRow]:
             # We could technically use simple_select_list here, but we need to call
             # COALESCE on the 'enabled' column. While it is technically possible to give
             # simple_select_list the whole `COALESCE(...) AS ...` as a column name, it
@@ -220,7 +216,7 @@ class PusherWorkerStore(SQLBaseStore):
 
             txn.execute(sql, list(keyvalues.values()))
 
-            return cast(List[PusherRow], txn.fetchall())
+            return cast(list[PusherRow], txn.fetchall())
 
         ret = await self.db_pool.runInteraction(
             desc="get_pushers_by",
@@ -230,7 +226,7 @@ class PusherWorkerStore(SQLBaseStore):
         return self._decode_pushers_rows(ret)
 
     async def get_enabled_pushers(self) -> Iterator[PusherConfig]:
-        def get_enabled_pushers_txn(txn: LoggingTransaction) -> List[PusherRow]:
+        def get_enabled_pushers_txn(txn: LoggingTransaction) -> list[PusherRow]:
             txn.execute(
                 """
                 SELECT id, user_name, access_token, profile_tag, kind, app_id,
@@ -240,7 +236,7 @@ class PusherWorkerStore(SQLBaseStore):
                 FROM pushers WHERE COALESCE(enabled, TRUE)
                 """
             )
-            return cast(List[PusherRow], txn.fetchall())
+            return cast(list[PusherRow], txn.fetchall())
 
         return self._decode_pushers_rows(
             await self.db_pool.runInteraction(
@@ -250,7 +246,7 @@ class PusherWorkerStore(SQLBaseStore):
 
     async def get_all_updated_pushers_rows(
         self, instance_name: str, last_id: int, current_id: int, limit: int
-    ) -> Tuple[List[Tuple[int, tuple]], int, bool]:
+    ) -> tuple[list[tuple[int, tuple]], int, bool]:
         """Get updates for pushers replication stream.
 
         Args:
@@ -277,7 +273,7 @@ class PusherWorkerStore(SQLBaseStore):
 
         def get_all_updated_pushers_rows_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[List[Tuple[int, tuple]], int, bool]:
+        ) -> tuple[list[tuple[int, tuple]], int, bool]:
             sql = """
                 SELECT id, user_name, app_id, pushkey
                 FROM pushers
@@ -286,7 +282,7 @@ class PusherWorkerStore(SQLBaseStore):
             """
             txn.execute(sql, (last_id, current_id, limit))
             updates = cast(
-                List[Tuple[int, tuple]],
+                list[tuple[int, tuple]],
                 [
                     (stream_id, (user_name, app_id, pushkey, False))
                     for stream_id, user_name, app_id, pushkey in txn
@@ -368,7 +364,7 @@ class PusherWorkerStore(SQLBaseStore):
         return bool(updated)
 
     async def update_pusher_failing_since(
-        self, app_id: str, pushkey: str, user_id: str, failing_since: Optional[int]
+        self, app_id: str, pushkey: str, user_id: str, failing_since: int | None
     ) -> None:
         await self.db_pool.simple_update(
             table="pushers",
@@ -379,9 +375,9 @@ class PusherWorkerStore(SQLBaseStore):
 
     async def get_throttle_params_by_room(
         self, pusher_id: int
-    ) -> Dict[str, ThrottleParams]:
+    ) -> dict[str, ThrottleParams]:
         res = cast(
-            List[Tuple[str, Optional[int], Optional[int]]],
+            list[tuple[str, int | None, int | None]],
             await self.db_pool.simple_select_list(
                 "pusher_throttle",
                 {"pusher": pusher_id},
@@ -610,7 +606,7 @@ class PusherBackgroundUpdatesStore(SQLBaseStore):
                 (last_pusher_id, batch_size),
             )
 
-            rows = cast(List[Tuple[int, Optional[str], Optional[str]]], txn.fetchall())
+            rows = cast(list[tuple[int, str | None, str | None]], txn.fetchall())
             if len(rows) == 0:
                 return 0
 
@@ -669,13 +665,13 @@ class PusherStore(PusherWorkerStore, PusherBackgroundUpdatesStore):
         device_display_name: str,
         pushkey: str,
         pushkey_ts: int,
-        lang: Optional[str],
-        data: Optional[JsonDict],
+        lang: str | None,
+        data: JsonDict | None,
         last_stream_ordering: int,
         profile_tag: str = "",
         enabled: bool = True,
-        device_id: Optional[str] = None,
-        access_token_id: Optional[int] = None,
+        device_id: str | None = None,
+        access_token_id: int | None = None,
     ) -> None:
         async with self._pushers_id_gen.get_next() as stream_id:
             await self.db_pool.simple_upsert(
@@ -764,7 +760,7 @@ class PusherStore(PusherWorkerStore, PusherBackgroundUpdatesStore):
         # account.
         pushers = list(await self.get_pushers_by_user_id(user_id))
 
-        def delete_pushers_txn(txn: LoggingTransaction, stream_ids: List[int]) -> None:
+        def delete_pushers_txn(txn: LoggingTransaction, stream_ids: list[int]) -> None:
             self._invalidate_cache_and_stream(  # type: ignore[attr-defined]
                 txn, self.get_if_user_has_pusher, (user_id,)
             )
diff --git a/synapse/storage/databases/main/receipts.py b/synapse/storage/databases/main/receipts.py
index ff4eb9acb2..ba5e07a051 100644
--- a/synapse/storage/databases/main/receipts.py
+++ b/synapse/storage/databases/main/receipts.py
@@ -24,14 +24,9 @@ from typing import (
     TYPE_CHECKING,
     Any,
     Collection,
-    Dict,
     Iterable,
-    List,
     Mapping,
-    Optional,
     Sequence,
-    Set,
-    Tuple,
     cast,
 )
 
@@ -71,7 +66,7 @@ class ReceiptInRoom:
     receipt_type: str
     user_id: str
     event_id: str
-    thread_id: Optional[str]
+    thread_id: str | None
     data: JsonMapping
 
     @staticmethod
@@ -92,14 +87,14 @@ class ReceiptInRoom:
         # matching threaded receipts.
 
         # Set of (user_id, event_id)
-        unthreaded_receipts: Set[Tuple[str, str]] = {
+        unthreaded_receipts: set[tuple[str, str]] = {
             (receipt.user_id, receipt.event_id)
             for receipt in receipts
             if receipt.thread_id is None
         }
 
         # event_id -> receipt_type -> user_id -> receipt data
-        content: Dict[str, Dict[str, Dict[str, JsonMapping]]] = {}
+        content: dict[str, dict[str, dict[str, JsonMapping]]] = {}
         for receipt in receipts:
             data = receipt.data
             if receipt.thread_id is not None:
@@ -180,7 +175,7 @@ class ReceiptsWorkerStore(SQLBaseStore):
         user_id: str,
         room_id: str,
         receipt_types: Collection[str],
-    ) -> Optional[Tuple[str, int]]:
+    ) -> tuple[str, int] | None:
         """
         Fetch the event ID and stream_ordering for the latest unthreaded receipt
         in a room with one of the given receipt types.
@@ -212,11 +207,11 @@ class ReceiptsWorkerStore(SQLBaseStore):
         args.extend((user_id, room_id))
         txn.execute(sql, args)
 
-        return cast(Optional[Tuple[str, int]], txn.fetchone())
+        return cast(tuple[str, int] | None, txn.fetchone())
 
     async def get_receipts_for_user(
         self, user_id: str, receipt_types: Iterable[str]
-    ) -> Dict[str, str]:
+    ) -> dict[str, str]:
         """
         Fetch the event IDs for the latest receipts sent by the given user.
 
@@ -285,7 +280,7 @@ class ReceiptsWorkerStore(SQLBaseStore):
             A map of room ID to the latest receipt information.
         """
 
-        def f(txn: LoggingTransaction) -> List[Tuple[str, str, int, int]]:
+        def f(txn: LoggingTransaction) -> list[tuple[str, str, int, int]]:
             sql = (
                 "SELECT rl.room_id, rl.event_id,"
                 " e.topological_ordering, e.stream_ordering"
@@ -297,7 +292,7 @@ class ReceiptsWorkerStore(SQLBaseStore):
                 " AND receipt_type = ?"
             )
             txn.execute(sql, (user_id, receipt_type))
-            return cast(List[Tuple[str, str, int, int]], txn.fetchall())
+            return cast(list[tuple[str, str, int, int]], txn.fetchall())
 
         rows = await self.db_pool.runInteraction(
             "get_receipts_for_user_with_orderings", f
@@ -315,8 +310,8 @@ class ReceiptsWorkerStore(SQLBaseStore):
         self,
         room_ids: Iterable[str],
         to_key: MultiWriterStreamToken,
-        from_key: Optional[MultiWriterStreamToken] = None,
-    ) -> List[JsonMapping]:
+        from_key: MultiWriterStreamToken | None = None,
+    ) -> list[JsonMapping]:
         """Get receipts for multiple rooms for sending to clients.
 
         Args:
@@ -347,7 +342,7 @@ class ReceiptsWorkerStore(SQLBaseStore):
         self,
         room_id: str,
         to_key: MultiWriterStreamToken,
-        from_key: Optional[MultiWriterStreamToken] = None,
+        from_key: MultiWriterStreamToken | None = None,
     ) -> Sequence[JsonMapping]:
         """Get receipts for a single room for sending to clients.
 
@@ -375,11 +370,11 @@ class ReceiptsWorkerStore(SQLBaseStore):
         self,
         room_id: str,
         to_key: MultiWriterStreamToken,
-        from_key: Optional[MultiWriterStreamToken] = None,
+        from_key: MultiWriterStreamToken | None = None,
     ) -> Sequence[JsonMapping]:
         """See get_linearized_receipts_for_room"""
 
-        def f(txn: LoggingTransaction) -> List[Tuple[str, str, str, str]]:
+        def f(txn: LoggingTransaction) -> list[tuple[str, str, str, str]]:
             if from_key:
                 sql = """
                     SELECT stream_id, instance_name, receipt_type, user_id, event_id, data
@@ -429,7 +424,7 @@ class ReceiptsWorkerStore(SQLBaseStore):
         self,
         room_ids: Collection[str],
         to_key: MultiWriterStreamToken,
-        from_key: Optional[MultiWriterStreamToken] = None,
+        from_key: MultiWriterStreamToken | None = None,
     ) -> Mapping[str, Sequence[JsonMapping]]:
         if not room_ids:
             return {}
@@ -466,7 +461,7 @@ class ReceiptsWorkerStore(SQLBaseStore):
 
                 txn.execute(sql + clause, [to_key.get_max_stream_pos()] + list(args))
 
-            results: Dict[str, List[ReceiptInRoom]] = {}
+            results: dict[str, list[ReceiptInRoom]] = {}
             for (
                 stream_id,
                 instance_name,
@@ -515,7 +510,7 @@ class ReceiptsWorkerStore(SQLBaseStore):
 
     async def get_linearized_receipts_for_events(
         self,
-        room_and_event_ids: Collection[Tuple[str, str]],
+        room_and_event_ids: Collection[tuple[str, str]],
     ) -> Mapping[str, Sequence[ReceiptInRoom]]:
         """Get all receipts for the given set of events.
 
@@ -531,8 +526,8 @@ class ReceiptsWorkerStore(SQLBaseStore):
 
         def get_linearized_receipts_for_events_txn(
             txn: LoggingTransaction,
-            room_id_event_id_tuples: Collection[Tuple[str, str]],
-        ) -> List[Tuple[str, str, str, str, Optional[str], str]]:
+            room_id_event_id_tuples: Collection[tuple[str, str]],
+        ) -> list[tuple[str, str, str, str, str | None, str]]:
             clause, args = make_tuple_in_list_sql_clause(
                 self.database_engine, ("room_id", "event_id"), room_id_event_id_tuples
             )
@@ -548,7 +543,7 @@ class ReceiptsWorkerStore(SQLBaseStore):
             return txn.fetchall()
 
         # room_id -> receipts
-        room_to_receipts: Dict[str, List[ReceiptInRoom]] = {}
+        room_to_receipts: dict[str, list[ReceiptInRoom]] = {}
         for batch in batch_iter(room_and_event_ids, 1000):
             batch_results = await self.db_pool.runInteraction(
                 "get_linearized_receipts_for_events",
@@ -582,7 +577,7 @@ class ReceiptsWorkerStore(SQLBaseStore):
     async def get_linearized_receipts_for_all_rooms(
         self,
         to_key: MultiWriterStreamToken,
-        from_key: Optional[MultiWriterStreamToken] = None,
+        from_key: MultiWriterStreamToken | None = None,
     ) -> Mapping[str, JsonMapping]:
         """Get receipts for all rooms between two stream_ids, up
         to a limit of the latest 100 read receipts.
@@ -596,7 +591,7 @@ class ReceiptsWorkerStore(SQLBaseStore):
             A dictionary of roomids to a list of receipts.
         """
 
-        def f(txn: LoggingTransaction) -> List[Tuple[str, str, str, str, str]]:
+        def f(txn: LoggingTransaction) -> list[tuple[str, str, str, str, str]]:
             if from_key:
                 sql = """
                     SELECT stream_id, instance_name, room_id, receipt_type, user_id, event_id, data
@@ -659,7 +654,7 @@ class ReceiptsWorkerStore(SQLBaseStore):
         def get_linearized_receipts_for_user_in_rooms_txn(
             txn: LoggingTransaction,
             batch_room_ids: StrCollection,
-        ) -> List[Tuple[str, str, str, str, Optional[str], str]]:
+        ) -> list[tuple[str, str, str, str, str | None, str]]:
             clause, args = make_in_list_sql_clause(
                 self.database_engine, "room_id", batch_room_ids
             )
@@ -687,7 +682,7 @@ class ReceiptsWorkerStore(SQLBaseStore):
             ]
 
         # room_id -> receipts
-        room_to_receipts: Dict[str, List[ReceiptInRoom]] = {}
+        room_to_receipts: dict[str, list[ReceiptInRoom]] = {}
         for batch in batch_iter(room_ids, 1000):
             batch_results = await self.db_pool.runInteraction(
                 "get_linearized_receipts_for_events",
@@ -746,7 +741,7 @@ class ReceiptsWorkerStore(SQLBaseStore):
 
             return [room_id for (room_id,) in txn]
 
-        results: List[str] = []
+        results: list[str] = []
         for batch in batch_iter(room_ids, 1000):
             batch_result = await self.db_pool.runInteraction(
                 "get_rooms_with_receipts_between", f, batch
@@ -757,7 +752,7 @@ class ReceiptsWorkerStore(SQLBaseStore):
 
     async def get_users_sent_receipts_between(
         self, last_id: int, current_id: int
-    ) -> List[str]:
+    ) -> list[str]:
         """Get all users who sent receipts between `last_id` exclusive and
         `current_id` inclusive.
 
@@ -768,7 +763,7 @@ class ReceiptsWorkerStore(SQLBaseStore):
         if last_id == current_id:
             return []
 
-        def _get_users_sent_receipts_between_txn(txn: LoggingTransaction) -> List[str]:
+        def _get_users_sent_receipts_between_txn(txn: LoggingTransaction) -> list[str]:
             sql = """
                 SELECT DISTINCT user_id FROM receipts_linearized
                 WHERE ? < stream_id AND stream_id <= ?
@@ -783,8 +778,8 @@ class ReceiptsWorkerStore(SQLBaseStore):
 
     async def get_all_updated_receipts(
         self, instance_name: str, last_id: int, current_id: int, limit: int
-    ) -> Tuple[
-        List[Tuple[int, Tuple[str, str, str, str, Optional[str], JsonDict]]], int, bool
+    ) -> tuple[
+        list[tuple[int, tuple[str, str, str, str, str | None, JsonDict]]], int, bool
     ]:
         """Get updates for receipts replication stream.
 
@@ -812,8 +807,8 @@ class ReceiptsWorkerStore(SQLBaseStore):
 
         def get_all_updated_receipts_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[
-            List[Tuple[int, Tuple[str, str, str, str, Optional[str], JsonDict]]],
+        ) -> tuple[
+            list[tuple[int, tuple[str, str, str, str, str | None, JsonDict]]],
             int,
             bool,
         ]:
@@ -828,7 +823,7 @@ class ReceiptsWorkerStore(SQLBaseStore):
             txn.execute(sql, (last_id, current_id, instance_name, limit))
 
             updates = cast(
-                List[Tuple[int, Tuple[str, str, str, str, Optional[str], JsonDict]]],
+                list[tuple[int, tuple[str, str, str, str, str | None, JsonDict]]],
                 [(r[0], r[1:6] + (db_to_json(r[6]),)) for r in txn],
             )
 
@@ -888,10 +883,10 @@ class ReceiptsWorkerStore(SQLBaseStore):
         receipt_type: str,
         user_id: str,
         event_id: str,
-        thread_id: Optional[str],
+        thread_id: str | None,
         data: JsonDict,
         stream_id: int,
-    ) -> Optional[int]:
+    ) -> int | None:
         """Inserts a receipt into the database if it's newer than the current one.
 
         Returns:
@@ -917,7 +912,7 @@ class ReceiptsWorkerStore(SQLBaseStore):
         if stream_ordering is not None:
             if thread_id is None:
                 thread_clause = "r.thread_id IS NULL"
-                thread_args: Tuple[str, ...] = ()
+                thread_args: tuple[str, ...] = ()
             else:
                 thread_clause = "r.thread_id = ?"
                 thread_args = (thread_id,)
@@ -986,7 +981,7 @@ class ReceiptsWorkerStore(SQLBaseStore):
         return rx_ts
 
     def _graph_to_linear(
-        self, txn: LoggingTransaction, room_id: str, event_ids: List[str]
+        self, txn: LoggingTransaction, room_id: str, event_ids: list[str]
     ) -> str:
         """
         Generate a linearized event from a list of events (i.e. a list of forward
@@ -1026,10 +1021,10 @@ class ReceiptsWorkerStore(SQLBaseStore):
         room_id: str,
         receipt_type: str,
         user_id: str,
-        event_ids: List[str],
-        thread_id: Optional[str],
+        event_ids: list[str],
+        thread_id: str | None,
         data: dict,
-    ) -> Optional[PersistedPosition]:
+    ) -> PersistedPosition | None:
         """Insert a receipt, either from local client or remote server.
 
         Automatically does conversion between linearized and graph
@@ -1073,7 +1068,7 @@ class ReceiptsWorkerStore(SQLBaseStore):
         if event_ts is None:
             return None
 
-        now = self._clock.time_msec()
+        now = self.clock.time_msec()
         logger.debug(
             "Receipt %s for event %s in %s (%i ms old)",
             receipt_type,
@@ -1098,8 +1093,8 @@ class ReceiptsWorkerStore(SQLBaseStore):
         room_id: str,
         receipt_type: str,
         user_id: str,
-        event_ids: List[str],
-        thread_id: Optional[str],
+        event_ids: list[str],
+        thread_id: str | None,
         data: JsonDict,
     ) -> None:
         assert self._can_write_to_receipts
@@ -1237,7 +1232,7 @@ class ReceiptsBackgroundUpdateStore(SQLBaseStore):
                 HAVING COUNT(*) > 1
             """
             txn.execute(sql)
-            duplicate_keys = cast(List[Tuple[int, str, str, str]], list(txn))
+            duplicate_keys = cast(list[tuple[int, str, str, str]], list(txn))
 
             # Then remove duplicate receipts, keeping the one with the highest
             # `stream_id`. Since there might be duplicate rows with the same
@@ -1255,7 +1250,7 @@ class ReceiptsBackgroundUpdateStore(SQLBaseStore):
                 LIMIT 1
                 """
                 txn.execute(sql, (room_id, receipt_type, user_id, stream_id))
-                row_id = cast(Tuple[str], txn.fetchone())[0]
+                row_id = cast(tuple[str], txn.fetchone())[0]
 
                 sql = f"""
                     DELETE FROM receipts_linearized
@@ -1306,7 +1301,7 @@ class ReceiptsBackgroundUpdateStore(SQLBaseStore):
                 HAVING COUNT(*) > 1
             """
             txn.execute(sql)
-            duplicate_keys = cast(List[Tuple[str, str, str]], list(txn))
+            duplicate_keys = cast(list[tuple[str, str, str]], list(txn))
 
             # Then remove all duplicate receipts.
             # We could be clever and try to keep the latest receipt out of every set of
diff --git a/synapse/storage/databases/main/registration.py b/synapse/storage/databases/main/registration.py
index 117444e7b7..545b0f11c4 100644
--- a/synapse/storage/databases/main/registration.py
+++ b/synapse/storage/databases/main/registration.py
@@ -22,7 +22,7 @@
 import logging
 import random
 import re
-from typing import TYPE_CHECKING, Any, Dict, List, Optional, Tuple, Union, cast
+from typing import TYPE_CHECKING, Any, cast
 
 import attr
 
@@ -94,8 +94,8 @@ class TokenLookupResult:
     token_id: int
     is_guest: bool = False
     shadow_banned: bool = False
-    device_id: Optional[str] = None
-    valid_until_ms: Optional[int] = None
+    device_id: str | None = None
+    valid_until_ms: int | None = None
     token_owner: str = attr.ib()
     token_used: bool = False
 
@@ -118,7 +118,7 @@ class RefreshTokenLookupResult:
     token_id: int
     """The ID of this refresh token."""
 
-    next_token_id: Optional[int]
+    next_token_id: int | None
     """The ID of the refresh token which replaced this one."""
 
     has_next_refresh_token_been_refreshed: bool
@@ -127,11 +127,11 @@ class RefreshTokenLookupResult:
     has_next_access_token_been_used: bool
     """True if the next access token was already used at least once."""
 
-    expiry_ts: Optional[int]
+    expiry_ts: int | None
     """The time at which the refresh token expires and can not be used.
     If None, the refresh token doesn't expire."""
 
-    ultimate_session_expiry_ts: Optional[int]
+    ultimate_session_expiry_ts: int | None
     """The time at which the session comes to an end and can no longer be
     refreshed.
     If None, the session can be refreshed indefinitely."""
@@ -144,10 +144,10 @@ class LoginTokenLookupResult:
     user_id: str
     """The user this token belongs to."""
 
-    auth_provider_id: Optional[str]
+    auth_provider_id: str | None
     """The SSO Identity Provider that the user authenticated with, to get this token."""
 
-    auth_provider_session_id: Optional[str]
+    auth_provider_session_id: str | None
     """The session ID advertised by the SSO Identity Provider."""
 
 
@@ -171,7 +171,7 @@ class ThreepidValidationSession:
     """ID of the validation session"""
     last_send_attempt: int
     """a number serving to dedupe send attempts for this session"""
-    validated_at: Optional[int]
+    validated_at: int | None
     """timestamp of when this session was validated if so"""
 
 
@@ -212,7 +212,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
             )
 
             if hs.config.worker.run_background_tasks:
-                self._clock.call_later(
+                self.clock.call_later(
                     0.0,
                     self._set_expiration_date_when_missing,
                 )
@@ -226,20 +226,20 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
 
         # Create a background job for culling expired 3PID validity tokens
         if hs.config.worker.run_background_tasks:
-            self._clock.looping_call(
+            self.clock.looping_call(
                 self.cull_expired_threepid_validation_tokens, THIRTY_MINUTES_IN_MS
             )
 
     async def register_user(
         self,
         user_id: str,
-        password_hash: Optional[str] = None,
+        password_hash: str | None = None,
         was_guest: bool = False,
         make_guest: bool = False,
-        appservice_id: Optional[str] = None,
-        create_profile_with_displayname: Optional[str] = None,
+        appservice_id: str | None = None,
+        create_profile_with_displayname: str | None = None,
         admin: bool = False,
-        user_type: Optional[str] = None,
+        user_type: str | None = None,
         shadow_banned: bool = False,
         approved: bool = False,
     ) -> None:
@@ -286,19 +286,19 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
         self,
         txn: LoggingTransaction,
         user_id: str,
-        password_hash: Optional[str],
+        password_hash: str | None,
         was_guest: bool,
         make_guest: bool,
-        appservice_id: Optional[str],
-        create_profile_with_displayname: Optional[str],
+        appservice_id: str | None,
+        create_profile_with_displayname: str | None,
         admin: bool,
-        user_type: Optional[str],
+        user_type: str | None,
         shadow_banned: bool,
         approved: bool,
     ) -> None:
         user_id_obj = UserID.from_string(user_id)
 
-        now = int(self._clock.time())
+        now = int(self.clock.time())
 
         user_approved = approved or not self._require_approval
 
@@ -379,10 +379,10 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
         self._invalidate_cache_and_stream(txn, self.get_user_by_id, (user_id,))
 
     @cached()
-    async def get_user_by_id(self, user_id: str) -> Optional[UserInfo]:
+    async def get_user_by_id(self, user_id: str) -> UserInfo | None:
         """Returns info about the user account, if it exists."""
 
-        def get_user_by_id_txn(txn: LoggingTransaction) -> Optional[UserInfo]:
+        def get_user_by_id_txn(txn: LoggingTransaction) -> UserInfo | None:
             # We could technically use simple_select_one here, but it would not perform
             # the COALESCEs (unless hacked into the column names), which could yield
             # confusing results.
@@ -457,7 +457,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
         if not info:
             return False
 
-        now = self._clock.time_msec()
+        now = self.clock.time_msec()
         days = self.config.server.mau_appservice_trial_days.get(
             info.appservice_id, self.config.server.mau_trial_days
         )
@@ -466,7 +466,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
         return is_trial
 
     @cached()
-    async def get_user_by_access_token(self, token: str) -> Optional[TokenLookupResult]:
+    async def get_user_by_access_token(self, token: str) -> TokenLookupResult | None:
         """Get a user from the given access token.
 
         Args:
@@ -479,7 +479,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
         )
 
     @cached()
-    async def get_expiration_ts_for_user(self, user_id: str) -> Optional[int]:
+    async def get_expiration_ts_for_user(self, user_id: str) -> int | None:
         """Get the expiration timestamp for the account bearing a given user ID.
 
         Args:
@@ -515,8 +515,8 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
         user_id: str,
         expiration_ts: int,
         email_sent: bool,
-        renewal_token: Optional[str] = None,
-        token_used_ts: Optional[int] = None,
+        renewal_token: str | None = None,
+        token_used_ts: int | None = None,
     ) -> None:
         """Updates the account validity properties of the given account, with the
         given values.
@@ -576,7 +576,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
 
     async def get_user_from_renewal_token(
         self, renewal_token: str
-    ) -> Tuple[str, int, Optional[int]]:
+    ) -> tuple[str, int, int | None]:
         """Get a user ID and renewal status from a renewal token.
 
         Args:
@@ -592,7 +592,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
                     has not been renewed using the current token yet.
         """
         return cast(
-            Tuple[str, int, Optional[int]],
+            tuple[str, int, int | None],
             await self.db_pool.simple_select_one(
                 table="account_validity",
                 keyvalues={"renewal_token": renewal_token},
@@ -617,7 +617,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
             desc="get_renewal_token_for_user",
         )
 
-    async def get_users_expiring_soon(self) -> List[Tuple[str, int]]:
+    async def get_users_expiring_soon(self) -> list[tuple[str, int]]:
         """Selects users whose account will expire in the [now, now + renew_at] time
         window (see configuration for account_validity for information on what renew_at
         refers to).
@@ -628,19 +628,19 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
 
         def select_users_txn(
             txn: LoggingTransaction, now_ms: int, renew_at: int
-        ) -> List[Tuple[str, int]]:
+        ) -> list[tuple[str, int]]:
             sql = (
                 "SELECT user_id, expiration_ts_ms FROM account_validity"
                 " WHERE email_sent = FALSE AND (expiration_ts_ms - ?) <= ?"
             )
             values = [now_ms, renew_at]
             txn.execute(sql, values)
-            return cast(List[Tuple[str, int]], txn.fetchall())
+            return cast(list[tuple[str, int]], txn.fetchall())
 
         return await self.db_pool.runInteraction(
             "get_users_expiring_soon",
             select_users_txn,
-            self._clock.time_msec(),
+            self.clock.time_msec(),
             self.config.account_validity.account_validity_renew_at,
         )
 
@@ -745,7 +745,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
         await self.db_pool.runInteraction("set_shadow_banned", set_shadow_banned_txn)
 
     async def set_user_type(
-        self, user: UserID, user_type: Optional[Union[UserTypes, str]]
+        self, user: UserID, user_type: UserTypes | str | None
     ) -> None:
         """Sets the user type.
 
@@ -766,7 +766,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
 
     def _query_for_auth(
         self, txn: LoggingTransaction, token: str
-    ) -> Optional[TokenLookupResult]:
+    ) -> TokenLookupResult | None:
         sql = """
             SELECT users.name as user_id,
                 users.is_guest,
@@ -858,17 +858,17 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
         )
         return True if res == UserTypes.SUPPORT else False
 
-    async def get_users_by_id_case_insensitive(self, user_id: str) -> Dict[str, str]:
+    async def get_users_by_id_case_insensitive(self, user_id: str) -> dict[str, str]:
         """Gets users that match user_id case insensitively.
 
         Returns:
              A mapping of user_id -> password_hash.
         """
 
-        def f(txn: LoggingTransaction) -> Dict[str, str]:
+        def f(txn: LoggingTransaction) -> dict[str, str]:
             sql = "SELECT name, password_hash FROM users WHERE lower(name) = lower(?)"
             txn.execute(sql, (user_id,))
-            result = cast(List[Tuple[str, str]], txn.fetchall())
+            result = cast(list[tuple[str, str]], txn.fetchall())
             return dict(result)
 
         return await self.db_pool.runInteraction("get_users_by_id_case_insensitive", f)
@@ -978,7 +978,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
 
     async def replace_user_external_id(
         self,
-        record_external_ids: List[Tuple[str, str]],
+        record_external_ids: list[tuple[str, str]],
         user_id: str,
     ) -> None:
         """Replace mappings from external user ids to a mxid in a single transaction.
@@ -1027,7 +1027,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
     @cached()
     async def get_user_by_external_id(
         self, auth_provider: str, external_id: str
-    ) -> Optional[str]:
+    ) -> str | None:
         """Look up a user by their external auth id
 
         Args:
@@ -1045,7 +1045,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
             desc="get_user_by_external_id",
         )
 
-    async def get_external_ids_by_user(self, mxid: str) -> List[Tuple[str, str]]:
+    async def get_external_ids_by_user(self, mxid: str) -> list[tuple[str, str]]:
         """Look up external ids for the given user
 
         Args:
@@ -1055,7 +1055,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
             Tuples of (auth_provider, external_id)
         """
         return cast(
-            List[Tuple[str, str]],
+            list[tuple[str, str]],
             await self.db_pool.simple_select_list(
                 table="user_external_ids",
                 keyvalues={"user_id": mxid},
@@ -1075,7 +1075,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
 
         return await self.db_pool.runInteraction("count_users", _count_users)
 
-    async def count_daily_user_type(self) -> Dict[str, int]:
+    async def count_daily_user_type(self) -> dict[str, int]:
         """
         Counts 1) native non guest users
                2) native guests users
@@ -1083,8 +1083,8 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
         who registered on the homeserver in the past 24 hours
         """
 
-        def _count_daily_user_type(txn: LoggingTransaction) -> Dict[str, int]:
-            yesterday = int(self._clock.time()) - (60 * 60 * 24)
+        def _count_daily_user_type(txn: LoggingTransaction) -> dict[str, int]:
+            yesterday = int(self.clock.time()) - (60 * 60 * 24)
 
             sql = """
                 SELECT user_type, COUNT(*) AS count FROM (
@@ -1116,7 +1116,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
                 WHERE appservice_id IS NULL
             """
             )
-            (count,) = cast(Tuple[int], txn.fetchone())
+            (count,) = cast(tuple[int], txn.fetchone())
             return count
 
         return await self.db_pool.runInteraction("count_users", _count_users)
@@ -1145,7 +1145,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
 
         return str(next_id)
 
-    async def get_user_id_by_threepid(self, medium: str, address: str) -> Optional[str]:
+    async def get_user_id_by_threepid(self, medium: str, address: str) -> str | None:
         """Returns user id from threepid
 
         Args:
@@ -1163,7 +1163,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
 
     def get_user_id_by_threepid_txn(
         self, txn: LoggingTransaction, medium: str, address: str
-    ) -> Optional[str]:
+    ) -> str | None:
         """Returns user id from threepid
 
         Args:
@@ -1196,9 +1196,9 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
             {"user_id": user_id, "validated_at": validated_at, "added_at": added_at},
         )
 
-    async def user_get_threepids(self, user_id: str) -> List[ThreepidResult]:
+    async def user_get_threepids(self, user_id: str) -> list[ThreepidResult]:
         results = cast(
-            List[Tuple[str, str, int, int]],
+            list[tuple[str, str, int, int]],
             await self.db_pool.simple_select_list(
                 "user_threepids",
                 keyvalues={"user_id": user_id},
@@ -1253,7 +1253,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
             desc="add_user_bound_threepid",
         )
 
-    async def user_get_bound_threepids(self, user_id: str) -> List[Tuple[str, str]]:
+    async def user_get_bound_threepids(self, user_id: str) -> list[tuple[str, str]]:
         """Get the threepids that a user has bound to an identity server through the homeserver
         The homeserver remembers where binds to an identity server occurred. Using this
         method can retrieve those threepids.
@@ -1267,7 +1267,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
                 address: The address of the threepid (e.g "bob@example.com")
         """
         return cast(
-            List[Tuple[str, str]],
+            list[tuple[str, str]],
             await self.db_pool.simple_select_list(
                 table="user_threepid_id_server",
                 keyvalues={"user_id": user_id},
@@ -1302,7 +1302,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
 
     async def get_id_servers_user_bound(
         self, user_id: str, medium: str, address: str
-    ) -> List[str]:
+    ) -> list[str]:
         """Get the list of identity servers that the server proxied bind
         requests to for given user and threepid
 
@@ -1386,12 +1386,12 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
 
     async def get_threepid_validation_session(
         self,
-        medium: Optional[str],
+        medium: str | None,
         client_secret: str,
-        address: Optional[str] = None,
-        sid: Optional[str] = None,
-        validated: Optional[bool] = True,
-    ) -> Optional[ThreepidValidationSession]:
+        address: str | None = None,
+        sid: str | None = None,
+        validated: bool | None = True,
+    ) -> ThreepidValidationSession | None:
         """Gets a session_id and last_send_attempt (if available) for a
         combination of validation metadata
 
@@ -1425,7 +1425,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
 
         def get_threepid_validation_session_txn(
             txn: LoggingTransaction,
-        ) -> Optional[ThreepidValidationSession]:
+        ) -> ThreepidValidationSession | None:
             sql = """
                 SELECT address, session_id, medium, client_secret,
                 last_send_attempt, validated_at
@@ -1496,7 +1496,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
         await self.db_pool.runInteraction(
             "cull_expired_threepid_validation_tokens",
             cull_expired_threepid_validation_tokens_txn,
-            self._clock.time_msec(),
+            self.clock.time_msec(),
         )
 
     @wrap_as_background_process("account_validity_set_expiration_dates")
@@ -1537,7 +1537,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
                 random value in the [now + period - d ; now + period] range, d being a
                 delta equal to 10% of the validity period.
         """
-        now_ms = self._clock.time_msec()
+        now_ms = self.clock.time_msec()
         assert self._account_validity_period is not None
         expiration_ts = now_ms + self._account_validity_period
 
@@ -1555,7 +1555,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
             values={"expiration_ts_ms": expiration_ts, "email_sent": False},
         )
 
-    async def get_user_pending_deactivation(self) -> Optional[str]:
+    async def get_user_pending_deactivation(self) -> str | None:
         """
         Gets one user from the table of users waiting to be parted from all the rooms
         they're in.
@@ -1608,7 +1608,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
         Raises:
             StoreError if there was a problem updating this.
         """
-        now = self._clock.time_msec()
+        now = self.clock.time_msec()
 
         await self.db_pool.simple_update_one(
             "access_tokens",
@@ -1639,7 +1639,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
         uses_allowed, pending, completed, expiry_time = res
 
         # Check if the token has expired
-        now = self._clock.time_msec()
+        now = self.clock.time_msec()
         if expiry_time and expiry_time < now:
             return False
 
@@ -1686,7 +1686,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
         """
 
         def _use_registration_token_txn(txn: LoggingTransaction) -> None:
-            # Normally, res is Optional[Dict[str, Any]].
+            # Normally, res is dict[str, Any] | None.
             # Override type because the return type is only optional if
             # allow_none is True, and we don't want mypy throwing errors
             # about None not being indexable.
@@ -1715,8 +1715,8 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
         )
 
     async def get_registration_tokens(
-        self, valid: Optional[bool] = None
-    ) -> List[Tuple[str, Optional[int], int, int, Optional[int]]]:
+        self, valid: bool | None = None
+    ) -> list[tuple[str, int | None, int, int, int | None]]:
         """List all registration tokens. Used by the admin API.
 
         Args:
@@ -1734,8 +1734,8 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
         """
 
         def select_registration_tokens_txn(
-            txn: LoggingTransaction, now: int, valid: Optional[bool]
-        ) -> List[Tuple[str, Optional[int], int, int, Optional[int]]]:
+            txn: LoggingTransaction, now: int, valid: bool | None
+        ) -> list[tuple[str, int | None, int, int, int | None]]:
             if valid is None:
                 # Return all tokens regardless of validity
                 txn.execute(
@@ -1765,17 +1765,17 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
                 txn.execute(sql, [now])
 
             return cast(
-                List[Tuple[str, Optional[int], int, int, Optional[int]]], txn.fetchall()
+                list[tuple[str, int | None, int, int, int | None]], txn.fetchall()
             )
 
         return await self.db_pool.runInteraction(
             "select_registration_tokens",
             select_registration_tokens_txn,
-            self._clock.time_msec(),
+            self.clock.time_msec(),
             valid,
         )
 
-    async def get_one_registration_token(self, token: str) -> Optional[Dict[str, Any]]:
+    async def get_one_registration_token(self, token: str) -> dict[str, Any] | None:
         """Get info about the given registration token. Used by the admin API.
 
         Args:
@@ -1801,9 +1801,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
             "expiry_time": row[4],
         }
 
-    async def generate_registration_token(
-        self, length: int, chars: str
-    ) -> Optional[str]:
+    async def generate_registration_token(self, length: int, chars: str) -> str | None:
         """Generate a random registration token. Used by the admin API.
 
         Args:
@@ -1843,7 +1841,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
         )
 
     async def create_registration_token(
-        self, token: str, uses_allowed: Optional[int], expiry_time: Optional[int]
+        self, token: str, uses_allowed: int | None, expiry_time: int | None
     ) -> bool:
         """Create a new registration token. Used by the admin API.
 
@@ -1892,8 +1890,8 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
         )
 
     async def update_registration_token(
-        self, token: str, updatevalues: Dict[str, Optional[int]]
-    ) -> Optional[Dict[str, Any]]:
+        self, token: str, updatevalues: dict[str, int | None]
+    ) -> dict[str, Any] | None:
         """Update a registration token. Used by the admin API.
 
         Args:
@@ -1909,7 +1907,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
 
         def _update_registration_token_txn(
             txn: LoggingTransaction,
-        ) -> Optional[Dict[str, Any]]:
+        ) -> dict[str, Any] | None:
             try:
                 self.db_pool.simple_update_one_txn(
                     txn,
@@ -1996,14 +1994,12 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
             desc="mark_access_token_as_used",
         )
 
-    async def lookup_refresh_token(
-        self, token: str
-    ) -> Optional[RefreshTokenLookupResult]:
+    async def lookup_refresh_token(self, token: str) -> RefreshTokenLookupResult | None:
         """Lookup a refresh token with hints about its validity."""
 
         def _lookup_refresh_token_txn(
             txn: LoggingTransaction,
-        ) -> Optional[RefreshTokenLookupResult]:
+        ) -> RefreshTokenLookupResult | None:
             txn.execute(
                 """
                 SELECT
@@ -2154,8 +2150,8 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
         user_id: str,
         token: str,
         expiry_ts: int,
-        auth_provider_id: Optional[str],
-        auth_provider_session_id: Optional[str],
+        auth_provider_id: str | None,
+        auth_provider_session_id: str | None,
     ) -> None:
         """Adds a short-term login token for the given user.
 
@@ -2251,7 +2247,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
             "consume_login_token",
             self._consume_login_token,
             token,
-            self._clock.time_msec(),
+            self.clock.time_msec(),
         )
 
     async def invalidate_login_tokens_by_session_id(
@@ -2271,7 +2267,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
                 "auth_provider_id": auth_provider_id,
                 "auth_provider_session_id": auth_provider_session_id,
             },
-            updatevalues={"used_ts": self._clock.time_msec()},
+            updatevalues={"used_ts": self.clock.time_msec()},
             desc="invalidate_login_tokens_by_session_id",
         )
 
@@ -2455,9 +2451,9 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
     async def user_delete_access_tokens(
         self,
         user_id: str,
-        except_token_id: Optional[int] = None,
-        device_id: Optional[str] = None,
-    ) -> List[Tuple[str, int, Optional[str]]]:
+        except_token_id: int | None = None,
+        device_id: str | None = None,
+    ) -> list[tuple[str, int, str | None]]:
         """
         Invalidate access and refresh tokens belonging to a user
 
@@ -2471,14 +2467,14 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
             A tuple of (token, token id, device id) for each of the deleted tokens
         """
 
-        def f(txn: LoggingTransaction) -> List[Tuple[str, int, Optional[str]]]:
+        def f(txn: LoggingTransaction) -> list[tuple[str, int, str | None]]:
             keyvalues = {"user_id": user_id}
             if device_id is not None:
                 keyvalues["device_id"] = device_id
 
             items = keyvalues.items()
             where_clause = " AND ".join(k + " = ?" for k, _ in items)
-            values: List[Union[str, int]] = [v for _, v in items]
+            values: list[str | int] = [v for _, v in items]
             # Conveniently, refresh_tokens and access_tokens both use the user_id and device_id fields. Only caveat
             # is the `except_token_id` param that is tricky to get right, so for now we're just using the same where
             # clause and values before we handle that. This seems to be only used in the "set password" handler.
@@ -2517,7 +2513,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
         self,
         user_id: str,
         device_ids: StrCollection,
-    ) -> List[Tuple[str, int, Optional[str]]]:
+    ) -> list[tuple[str, int, str | None]]:
         """
         Invalidate access and refresh tokens belonging to a user
 
@@ -2530,7 +2526,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
 
         def user_delete_access_tokens_for_devices_txn(
             txn: LoggingTransaction, batch_device_ids: StrCollection
-        ) -> List[Tuple[str, int, Optional[str]]]:
+        ) -> list[tuple[str, int, str | None]]:
             self.db_pool.simple_delete_many_txn(
                 txn,
                 table="refresh_tokens",
@@ -2544,31 +2540,13 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
             )
             args.append(user_id)
 
-            if self.database_engine.supports_returning:
-                sql = f"""
-                    DELETE FROM access_tokens
-                    WHERE {clause} AND user_id = ?
-                    RETURNING token, id, device_id
-                """
-                txn.execute(sql, args)
-                tokens_and_devices = txn.fetchall()
-            else:
-                tokens_and_devices = self.db_pool.simple_select_many_txn(
-                    txn,
-                    table="access_tokens",
-                    column="device_id",
-                    iterable=batch_device_ids,
-                    keyvalues={"user_id": user_id},
-                    retcols=("token", "id", "device_id"),
-                )
-
-                self.db_pool.simple_delete_many_txn(
-                    txn,
-                    table="access_tokens",
-                    keyvalues={"user_id": user_id},
-                    column="device_id",
-                    values=batch_device_ids,
-                )
+            sql = f"""
+                DELETE FROM access_tokens
+                WHERE {clause} AND user_id = ?
+                RETURNING token, id, device_id
+            """
+            txn.execute(sql, args)
+            tokens_and_devices = txn.fetchall()
 
             self._invalidate_cache_and_stream_bulk(
                 txn,
@@ -2601,7 +2579,7 @@ class RegistrationWorkerStore(StatsStore, CacheInvalidationWorkerStore):
         await self.db_pool.runInteraction("delete_access_token", f)
 
     async def user_set_password_hash(
-        self, user_id: str, password_hash: Optional[str]
+        self, user_id: str, password_hash: str | None
     ) -> None:
         """
         NB. This does *not* evict any cache because the one use for this
@@ -2640,7 +2618,6 @@ class RegistrationBackgroundUpdateStore(RegistrationWorkerStore):
     ):
         super().__init__(database, db_conn, hs)
 
-        self._clock = hs.get_clock()
         self.config = hs.config
 
         self.db_pool.updates.register_background_index_update(
@@ -2687,7 +2664,7 @@ class RegistrationBackgroundUpdateStore(RegistrationWorkerStore):
 
         def _background_update_set_deactivated_flag_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[bool, int]:
+        ) -> tuple[bool, int]:
             txn.execute(
                 """
                 SELECT
@@ -2761,7 +2738,7 @@ class RegistrationStore(RegistrationBackgroundUpdateStore):
 
         # Create a background job for removing expired login tokens
         if hs.config.worker.run_background_tasks:
-            self._clock.looping_call(
+            self.clock.looping_call(
                 self._delete_expired_login_tokens, THIRTY_MINUTES_IN_MS
             )
 
@@ -2769,10 +2746,10 @@ class RegistrationStore(RegistrationBackgroundUpdateStore):
         self,
         user_id: str,
         token: str,
-        device_id: Optional[str],
-        valid_until_ms: Optional[int],
-        puppets_user_id: Optional[str] = None,
-        refresh_token_id: Optional[int] = None,
+        device_id: str | None,
+        valid_until_ms: int | None,
+        puppets_user_id: str | None = None,
+        refresh_token_id: int | None = None,
     ) -> int:
         """Adds an access token for the given user.
 
@@ -2790,7 +2767,7 @@ class RegistrationStore(RegistrationBackgroundUpdateStore):
             The token ID
         """
         next_id = self._access_tokens_id_gen.get_next()
-        now = self._clock.time_msec()
+        now = self.clock.time_msec()
 
         await self.db_pool.simple_insert(
             "access_tokens",
@@ -2814,9 +2791,9 @@ class RegistrationStore(RegistrationBackgroundUpdateStore):
         self,
         user_id: str,
         token: str,
-        device_id: Optional[str],
-        expiry_ts: Optional[int],
-        ultimate_session_expiry_ts: Optional[int],
+        device_id: str | None,
+        expiry_ts: int | None,
+        ultimate_session_expiry_ts: int | None,
     ) -> int:
         """Adds a refresh token for the given user.
 
@@ -2874,7 +2851,7 @@ class RegistrationStore(RegistrationBackgroundUpdateStore):
                 keyvalues={"name": user_id},
                 updatevalues={
                     "consent_version": consent_version,
-                    "consent_ts": self._clock.time_msec(),
+                    "consent_ts": self.clock.time_msec(),
                 },
             )
             self._invalidate_cache_and_stream(txn, self.get_user_by_id, (user_id,))
@@ -2908,7 +2885,7 @@ class RegistrationStore(RegistrationBackgroundUpdateStore):
 
     async def validate_threepid_session(
         self, session_id: str, client_secret: str, token: str, current_ts: int
-    ) -> Optional[str]:
+    ) -> str | None:
         """Attempt to validate a threepid session using a token
 
         Args:
@@ -2928,7 +2905,7 @@ class RegistrationStore(RegistrationBackgroundUpdateStore):
         """
 
         # Insert everything into a transaction in order to run atomically
-        def validate_threepid_session_txn(txn: LoggingTransaction) -> Optional[str]:
+        def validate_threepid_session_txn(txn: LoggingTransaction) -> str | None:
             row = self.db_pool.simple_select_one_txn(
                 txn,
                 table="threepid_validation_session",
@@ -2986,7 +2963,7 @@ class RegistrationStore(RegistrationBackgroundUpdateStore):
                 txn,
                 table="threepid_validation_session",
                 keyvalues={"session_id": session_id},
-                updatevalues={"validated_at": self._clock.time_msec()},
+                updatevalues={"validated_at": self.clock.time_msec()},
             )
 
             return next_link
@@ -3003,7 +2980,7 @@ class RegistrationStore(RegistrationBackgroundUpdateStore):
         session_id: str,
         client_secret: str,
         send_attempt: int,
-        next_link: Optional[str],
+        next_link: str | None,
         token: str,
         token_expires: int,
     ) -> None:
@@ -3064,7 +3041,7 @@ class RegistrationStore(RegistrationBackgroundUpdateStore):
 
         # We keep the expired tokens for an extra 5 minutes so we can measure how many
         # times a token is being used after its expiry
-        now = self._clock.time_msec()
+        now = self.clock.time_msec()
         await self.db_pool.runInteraction(
             "delete_expired_login_tokens",
             _delete_expired_login_tokens_txn,
diff --git a/synapse/storage/databases/main/rejections.py b/synapse/storage/databases/main/rejections.py
index a603258644..c73c3d761d 100644
--- a/synapse/storage/databases/main/rejections.py
+++ b/synapse/storage/databases/main/rejections.py
@@ -20,7 +20,6 @@
 #
 
 import logging
-from typing import Optional
 
 from synapse.storage._base import SQLBaseStore
 
@@ -28,7 +27,7 @@ logger = logging.getLogger(__name__)
 
 
 class RejectionsStore(SQLBaseStore):
-    async def get_rejection_reason(self, event_id: str) -> Optional[str]:
+    async def get_rejection_reason(self, event_id: str) -> str | None:
         return await self.db_pool.simple_select_one_onecol(
             table="rejections",
             retcol="reason",
diff --git a/synapse/storage/databases/main/relations.py b/synapse/storage/databases/main/relations.py
index 5d412d38b3..c367c8a071 100644
--- a/synapse/storage/databases/main/relations.py
+++ b/synapse/storage/databases/main/relations.py
@@ -19,25 +19,19 @@
 #
 
 import logging
+from collections import defaultdict
 from typing import (
     TYPE_CHECKING,
     Collection,
-    Dict,
-    FrozenSet,
     Iterable,
-    List,
     Mapping,
-    Optional,
     Sequence,
-    Set,
-    Tuple,
-    Union,
     cast,
 )
 
 import attr
 
-from synapse.api.constants import MAIN_TIMELINE, Direction, Membership, RelationTypes
+from synapse.api.constants import MAIN_TIMELINE, Direction, RelationTypes
 from synapse.api.errors import SynapseError
 from synapse.events import EventBase
 from synapse.storage._base import SQLBaseStore
@@ -107,20 +101,14 @@ class ThreadUpdateInfo:
     Information about a thread update for the sliding sync threads extension.
 
     Attributes:
-        thread_id: The event ID of the thread root event (the event that started the thread).
+        event_id: The event ID of the event in the thread.
         room_id: The room ID where this thread exists.
-        thread_root_event: The actual EventBase object for the thread root event,
-            if include_thread_roots was True in the request. Otherwise None.
-        prev_batch: A pagination token (exclusive) for fetching older events in this thread.
-            Only present if update_count > 1. This token can be used with the /relations
-            endpoint with dir=b to paginate backwards through the thread's history without
-            re-receiving the latest event that was already included in the sliding sync response.
+        stream_ordering: The stream ordering of this event.
     """
 
-    thread_id: str
+    event_id: str
     room_id: str
-    thread_root_event: Optional[EventBase]
-    prev_batch: Optional[StreamToken]
+    stream_ordering: int
 
 
 class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
@@ -200,14 +188,14 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
         room_id: str,
         event_id: str,
         event: EventBase,
-        relation_type: Optional[str] = None,
-        event_type: Optional[str] = None,
+        relation_type: str | None = None,
+        event_type: str | None = None,
         limit: int = 5,
         direction: Direction = Direction.BACKWARDS,
-        from_token: Optional[StreamToken] = None,
-        to_token: Optional[StreamToken] = None,
+        from_token: StreamToken | None = None,
+        to_token: StreamToken | None = None,
         recurse: bool = False,
-    ) -> Tuple[Sequence[_RelatedEvent], Optional[StreamToken]]:
+    ) -> tuple[Sequence[_RelatedEvent], StreamToken | None]:
         """Get a list of relations for an event, ordered by topological ordering.
 
         Args:
@@ -237,7 +225,7 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
         assert limit >= 0
 
         where_clause = ["room_id = ?"]
-        where_args: List[Union[str, int]] = [room_id]
+        where_args: list[str | int] = [room_id]
         is_redacted = event.internal_metadata.is_redacted()
 
         if relation_type is not None:
@@ -309,14 +297,14 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
 
         def _get_recent_references_for_event_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[List[_RelatedEvent], Optional[StreamToken]]:
+        ) -> tuple[list[_RelatedEvent], StreamToken | None]:
             txn.execute(sql, [event.event_id] + where_args + [limit + 1])
 
             events = []
-            topo_orderings: List[int] = []
-            stream_orderings: List[int] = []
+            topo_orderings: list[int] = []
+            stream_orderings: list[int] = []
             for event_id, relation_type, sender, topo_ordering, stream_ordering in cast(
-                List[Tuple[str, str, str, int, int]], txn
+                list[tuple[str, str, str, int, int]], txn
             ):
                 # Do not include edits for redacted events as they leak event
                 # content.
@@ -357,8 +345,8 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
     async def get_all_relations_for_event_with_types(
         self,
         event_id: str,
-        relation_types: List[str],
-    ) -> List[str]:
+        relation_types: list[str],
+    ) -> list[str]:
         """Get the event IDs of all events that have a relation to the given event with
         one of the given relation types.
 
@@ -373,9 +361,9 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
 
         def get_all_relation_ids_for_event_with_types_txn(
             txn: LoggingTransaction,
-        ) -> List[str]:
+        ) -> list[str]:
             rows = cast(
-                List[Tuple[str]],
+                list[tuple[str]],
                 self.db_pool.simple_select_many_txn(
                     txn=txn,
                     table="event_relations",
@@ -396,7 +384,7 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
     async def get_all_relations_for_event(
         self,
         event_id: str,
-    ) -> List[str]:
+    ) -> list[str]:
         """Get the event IDs of all events that have a relation to the given event.
 
         Args:
@@ -408,9 +396,9 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
 
         def get_all_relation_ids_for_event_txn(
             txn: LoggingTransaction,
-        ) -> List[str]:
+        ) -> list[str]:
             rows = cast(
-                List[Tuple[str]],
+                list[tuple[str]],
                 self.db_pool.simple_select_list_txn(
                     txn=txn,
                     table="event_relations",
@@ -490,13 +478,13 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
         return result is not None
 
     @cached()  # type: ignore[synapse-@cached-mutable]
-    async def get_references_for_event(self, event_id: str) -> List[JsonDict]:
+    async def get_references_for_event(self, event_id: str) -> list[JsonDict]:
         raise NotImplementedError()
 
     @cachedList(cached_method_name="get_references_for_event", list_name="event_ids")
     async def get_references_for_events(
         self, event_ids: Collection[str]
-    ) -> Mapping[str, Optional[Sequence[_RelatedEvent]]]:
+    ) -> Mapping[str, Sequence[_RelatedEvent] | None]:
         """Get a list of references to the given events.
 
         Args:
@@ -526,12 +514,12 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
 
         def _get_references_for_events_txn(
             txn: LoggingTransaction,
-        ) -> Mapping[str, List[_RelatedEvent]]:
+        ) -> Mapping[str, list[_RelatedEvent]]:
             txn.execute(sql, args)
 
-            result: Dict[str, List[_RelatedEvent]] = {}
+            result: dict[str, list[_RelatedEvent]] = {}
             for relates_to_id, event_id, sender in cast(
-                List[Tuple[str, str, str]], txn
+                list[tuple[str, str, str]], txn
             ):
                 result.setdefault(relates_to_id, []).append(
                     _RelatedEvent(event_id, sender)
@@ -544,14 +532,14 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
         )
 
     @cached()  # type: ignore[synapse-@cached-mutable]
-    def get_applicable_edit(self, event_id: str) -> Optional[EventBase]:
+    def get_applicable_edit(self, event_id: str) -> EventBase | None:
         raise NotImplementedError()
 
     # TODO: This returns a mutable object, which is generally bad.
     @cachedList(cached_method_name="get_applicable_edit", list_name="event_ids")  # type: ignore[synapse-@cached-mutable]
     async def get_applicable_edits(
         self, event_ids: Collection[str]
-    ) -> Mapping[str, Optional[EventBase]]:
+    ) -> Mapping[str, EventBase | None]:
         """Get the most recent edit (if any) that has happened for the given
         events.
 
@@ -606,14 +594,14 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
                 ORDER by edit.origin_server_ts, edit.event_id
             """
 
-        def _get_applicable_edits_txn(txn: LoggingTransaction) -> Dict[str, str]:
+        def _get_applicable_edits_txn(txn: LoggingTransaction) -> dict[str, str]:
             clause, args = make_in_list_sql_clause(
                 txn.database_engine, "relates_to_id", event_ids
             )
             args.append(RelationTypes.REPLACE)
 
             txn.execute(sql % (clause,), args)
-            return dict(cast(Iterable[Tuple[str, str]], txn.fetchall()))
+            return dict(cast(Iterable[tuple[str, str]], txn.fetchall()))
 
         edit_ids = await self.db_pool.runInteraction(
             "get_applicable_edits", _get_applicable_edits_txn
@@ -635,14 +623,14 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
         }
 
     @cached()  # type: ignore[synapse-@cached-mutable]
-    def get_thread_summary(self, event_id: str) -> Optional[Tuple[int, EventBase]]:
+    def get_thread_summary(self, event_id: str) -> tuple[int, EventBase] | None:
         raise NotImplementedError()
 
     # TODO: This returns a mutable object, which is generally bad.
     @cachedList(cached_method_name="get_thread_summary", list_name="event_ids")  # type: ignore[synapse-@cached-mutable]
     async def get_thread_summaries(
         self, event_ids: Collection[str]
-    ) -> Mapping[str, Optional[Tuple[int, EventBase]]]:
+    ) -> Mapping[str, tuple[int, EventBase] | None]:
         """Get the number of threaded replies and the latest reply (if any) for the given events.
 
         Args:
@@ -659,7 +647,7 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
 
         def _get_thread_summaries_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[Dict[str, int], Dict[str, str]]:
+        ) -> tuple[dict[str, int], dict[str, str]]:
             # Fetch the count of threaded events and the latest event ID.
             # TODO Should this only allow m.room.message events.
             if isinstance(self.database_engine, PostgresEngine):
@@ -730,7 +718,7 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
             args.append(RelationTypes.THREAD)
 
             txn.execute(sql % (clause,), args)
-            counts = dict(cast(List[Tuple[str, int]], txn.fetchall()))
+            counts = dict(cast(list[tuple[str, int]], txn.fetchall()))
 
             return counts, latest_event_ids
 
@@ -758,8 +746,8 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
     async def get_threaded_messages_per_user(
         self,
         event_ids: Collection[str],
-        users: FrozenSet[str] = frozenset(),
-    ) -> Dict[Tuple[str, str], int]:
+        users: frozenset[str] = frozenset(),
+    ) -> dict[tuple[str, str], int]:
         """Get the number of threaded replies for a set of users.
 
         This is used, in conjunction with get_thread_summaries, to calculate an
@@ -791,7 +779,7 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
 
         def _get_threaded_messages_per_user_txn(
             txn: LoggingTransaction,
-        ) -> Dict[Tuple[str, str], int]:
+        ) -> dict[tuple[str, str], int]:
             users_sql, users_args = make_in_list_sql_clause(
                 self.database_engine, "child.sender", users
             )
@@ -831,7 +819,7 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
             user participated in that event's thread, otherwise false.
         """
 
-        def _get_threads_participated_txn(txn: LoggingTransaction) -> Set[str]:
+        def _get_threads_participated_txn(txn: LoggingTransaction) -> set[str]:
             # Fetch whether the requester has participated or not.
             sql = """
                 SELECT DISTINCT relates_to_id
@@ -862,10 +850,10 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
 
     async def events_have_relations(
         self,
-        parent_ids: List[str],
-        relation_senders: Optional[List[str]],
-        relation_types: Optional[List[str]],
-    ) -> List[str]:
+        parent_ids: list[str],
+        relation_senders: list[str] | None,
+        relation_types: list[str] | None,
+    ) -> list[str]:
         """Check which events have a relationship from the given senders of the
         given types.
 
@@ -888,8 +876,8 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
                 %s;
         """
 
-        def _get_if_events_have_relations(txn: LoggingTransaction) -> List[str]:
-            clauses: List[str] = []
+        def _get_if_events_have_relations(txn: LoggingTransaction) -> list[str]:
+            clauses: list[str] = []
             clause, args = make_in_list_sql_clause(
                 txn.database_engine, "relates_to_id", parent_ids
             )
@@ -967,8 +955,8 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
         self,
         room_id: str,
         limit: int = 5,
-        from_token: Optional[ThreadsNextBatch] = None,
-    ) -> Tuple[Sequence[str], Optional[ThreadsNextBatch]]:
+        from_token: ThreadsNextBatch | None = None,
+    ) -> tuple[Sequence[str], ThreadsNextBatch | None]:
         """Get a list of thread IDs, ordered by topological ordering of their
         latest reply.
 
@@ -1008,10 +996,10 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
 
         def _get_threads_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[List[str], Optional[ThreadsNextBatch]]:
+        ) -> tuple[list[str], ThreadsNextBatch | None]:
             txn.execute(sql, (room_id, *pagination_args, limit + 1))
 
-            rows = cast(List[Tuple[str, int, int]], txn.fetchall())
+            rows = cast(list[tuple[str, int, int]], txn.fetchall())
             thread_ids = [r[0] for r in rows]
 
             # If there are more events, generate the next pagination key from the
@@ -1150,33 +1138,33 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
             "get_related_thread_id", _get_related_thread_id
         )
 
-    async def get_thread_updates_for_user(
+    async def get_thread_updates_for_rooms(
         self,
         *,
-        user_id: str,
-        from_token: Optional[RoomStreamToken] = None,
-        to_token: Optional[RoomStreamToken] = None,
+        room_ids: Collection[str],
+        from_token: RoomStreamToken | None = None,
+        to_token: RoomStreamToken | None = None,
         limit: int = 5,
-        include_thread_roots: bool = False,
-    ) -> Tuple[Sequence[ThreadUpdateInfo], Optional[StreamToken]]:
+        exclude_thread_ids: Collection[str] | None = None,
+    ) -> tuple[dict[str, list[ThreadUpdateInfo]], StreamToken | None]:
         """Get a list of updated threads, ordered by stream ordering of their
         latest reply, filtered to only include threads in rooms where the user
         is currently joined.
 
         Args:
-            user_id: The user ID to fetch thread updates for. Only threads in rooms
-                where this user is currently joined will be returned.
+            room_ids: The room IDs to fetch thread updates for.
             from_token: The lower bound (exclusive) for thread updates. If None,
                 fetch from the start of the room timeline.
             to_token: The upper bound (inclusive) for thread updates. If None,
                 fetch up to the current position in the room timeline.
             limit: Maximum number of thread updates to return.
-            include_thread_roots: If True, fetch and return the thread root EventBase
-                objects. If False, return None for the thread_root_event field.
+            exclude_thread_ids: Optional collection of thread root event IDs to exclude
+                from the results. Useful for filtering out threads already visible
+                in the room timeline.
 
         Returns:
             A tuple of:
-                A list of ThreadUpdateInfo objects containing thread update information,
+                A dict mapping thread_id to list of ThreadUpdateInfo objects,
                 ordered by stream_ordering descending (most recent first).
                 A prev_batch StreamToken (exclusive) if there are more results available,
                 None otherwise.
@@ -1184,74 +1172,73 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
         # Ensure bad limits aren't being passed in.
         assert limit > 0
 
-        # Generate the pagination clause, if necessary.
-        #
-        # Find any threads where the latest reply is between the stream ordering bounds.
-        pagination_clause = ""
-        pagination_args: List[str] = []
-        if from_token:
-            from_bound = from_token.stream
-            pagination_clause += " AND stream_ordering > ?"
-            pagination_args.append(str(from_bound))
-
-        if to_token:
-            to_bound = to_token.stream
-            pagination_clause += " AND stream_ordering <= ?"
-            pagination_args.append(str(to_bound))
-
-        # Build the update count clause - count events in the thread within the sync window
-        update_count_clause = ""
-        update_count_args: List[str] = []
-        update_count_clause = f"""
-            (SELECT COUNT(*)
-             FROM event_relations AS er
-             INNER JOIN events AS e ON er.event_id = e.event_id
-             WHERE er.relates_to_id = threads.thread_id
-               AND er.relation_type = '{RelationTypes.THREAD}'"""
-        if from_token:
-            update_count_clause += " AND e.stream_ordering > ?"
-            update_count_args.append(str(from_token.stream))
-        if to_token:
-            update_count_clause += " AND e.stream_ordering <= ?"
-            update_count_args.append(str(to_token.stream))
-        update_count_clause += ")"
-
-        # Filter threads to only those in rooms where the user is currently joined.
-        sql = f"""
-            SELECT thread_id, room_id, stream_ordering, {update_count_clause} AS update_count
-              FROM threads
-              WHERE EXISTS (
-                  SELECT 1
-                  FROM local_current_membership AS lcm
-                  WHERE lcm.room_id = threads.room_id
-                      AND lcm.user_id = ?
-                      AND lcm.membership = ?
-              )
-              {pagination_clause}
-              ORDER BY stream_ordering DESC
-              LIMIT ?
-        """
+        if len(room_ids) == 0:
+            return ({}), None
 
         def _get_thread_updates_for_user_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[List[Tuple[str, str, int, int]], Optional[int]]:
-            # Add 1 to the limit as a free way of determining if there are more results
-            # than the limit amount. If `limit + 1` results are returned, then there are
-            # more results. Otherwise we would need to do a separate query to determine
-            # if this was true when exactly `limit` results are returned.
+        ) -> tuple[list[tuple[str, str, str, int]], int | None]:
+            room_clause, room_id_values = make_in_list_sql_clause(
+                txn.database_engine, "e.room_id", room_ids
+            )
+
+            # Generate the pagination clause, if necessary.
+            pagination_clause = ""
+            pagination_args: list[str] = []
+            if from_token:
+                from_bound = from_token.stream
+                pagination_clause += " AND stream_ordering > ?"
+                pagination_args.append(str(from_bound))
+
+            if to_token:
+                to_bound = to_token.stream
+                pagination_clause += " AND stream_ordering <= ?"
+                pagination_args.append(str(to_bound))
+
+            # Generate the exclusion clause for thread IDs, if necessary.
+            exclusion_clause = ""
+            exclusion_args: list[str] = []
+            if exclude_thread_ids:
+                exclusion_clause, exclusion_args = make_in_list_sql_clause(
+                    txn.database_engine,
+                    "er.relates_to_id",
+                    exclude_thread_ids,
+                    negative=True,
+                )
+                exclusion_clause = f" AND {exclusion_clause}"
+
+            # TODO: improve the fact that multiple hits for the same thread means we
+            # won't get as many overall updates for the sss response
+
+            # Find any thread events between the stream ordering bounds.
+            sql = f"""
+                SELECT e.event_id, er.relates_to_id, e.room_id, e.stream_ordering
+                  FROM event_relations AS er
+                  INNER JOIN events AS e ON er.event_id = e.event_id
+                  WHERE er.relation_type = '{RelationTypes.THREAD}'
+                  AND {room_clause}
+                  {exclusion_clause}
+                  {pagination_clause}
+                  ORDER BY stream_ordering DESC
+                  LIMIT ?
+            """
+
+            # Fetch `limit + 1` rows as a way to detect if there are more results beyond
+            # what we're returning. If we get exactly `limit + 1` rows back, we know there
+            # are more results available and we can set `next_token`. We only return the
+            # first `limit` rows to the caller. This avoids needing a separate COUNT query.
             txn.execute(
                 sql,
                 (
-                    *update_count_args,
-                    user_id,
-                    Membership.JOIN,
+                    *room_id_values,
+                    *exclusion_args,
                     *pagination_args,
                     limit + 1,
                 ),
             )
 
-            # SQL returns: thread_id, room_id, stream_ordering, update_count
-            rows = cast(List[Tuple[str, str, int, int]], txn.fetchall())
+            # SQL returns: event_id, thread_id, room_id, stream_ordering
+            rows = cast(list[tuple[str, str, str, int]], txn.fetchall())
 
             # If there are more events, generate the next pagination key from the
             # last thread which will be returned.
@@ -1261,7 +1248,7 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
                 # that will be the last row we return from this function.
                 # This works as an exclusive bound that can be backpaginated from.
                 # Use the stream_ordering field (index 2 in original rows)
-                next_token = rows[-2][2]
+                next_token = rows[-2][3]
 
             return rows[:limit], next_token
 
@@ -1280,35 +1267,14 @@ class RelationsWorkerStore(EventsWorkerStore, SQLBaseStore):
                 StreamKeyType.ROOM, RoomStreamToken(stream=next_token_int - 1)
             )
 
-        # Optionally fetch thread root events
-        event_map = {}
-        if include_thread_roots and thread_infos:
-            thread_root_ids = [thread_id for thread_id, _, _, _ in thread_infos]
-            thread_root_events = await self.get_events_as_list(thread_root_ids)
-            event_map = {e.event_id: e for e in thread_root_events}
-
-        # Build ThreadUpdateInfo objects with per-thread prev_batch tokens.
-        thread_update_infos = []
-        for thread_id, room_id, stream_ordering, update_count in thread_infos:
-            # Generate prev_batch token if this thread has more than one update.
-            per_thread_prev_batch = None
-            if update_count > 1:
-                # Create a token pointing to one position before the latest event's
-                # stream position.
-                # This makes it exclusive - /relations with dir=b won't return the
-                # latest event again.
-                # Use StreamToken.START as base (all other streams at 0) since only room
-                # position matters.
-                per_thread_prev_batch = StreamToken.START.copy_and_replace(
-                    StreamKeyType.ROOM, RoomStreamToken(stream=stream_ordering - 1)
-                )
-
-            thread_update_infos.append(
+        # Build ThreadUpdateInfo objects.
+        thread_update_infos: dict[str, list[ThreadUpdateInfo]] = defaultdict(list)
+        for event_id, thread_id, room_id, stream_ordering in thread_infos:
+            thread_update_infos[thread_id].append(
                 ThreadUpdateInfo(
-                    thread_id=thread_id,
+                    event_id=event_id,
                     room_id=room_id,
-                    thread_root_event=event_map.get(thread_id),
-                    prev_batch=per_thread_prev_batch,
+                    stream_ordering=stream_ordering,
                 )
             )
 
diff --git a/synapse/storage/databases/main/room.py b/synapse/storage/databases/main/room.py
index 9f03c084a5..633df07736 100644
--- a/synapse/storage/databases/main/room.py
+++ b/synapse/storage/databases/main/room.py
@@ -27,13 +27,7 @@ from typing import (
     AbstractSet,
     Any,
     Collection,
-    Dict,
-    List,
     Mapping,
-    Optional,
-    Set,
-    Tuple,
-    Union,
     cast,
 )
 
@@ -86,24 +80,24 @@ class RatelimitOverride:
 @attr.s(slots=True, frozen=True, auto_attribs=True)
 class LargestRoomStats:
     room_id: str
-    name: Optional[str]
-    canonical_alias: Optional[str]
+    name: str | None
+    canonical_alias: str | None
     joined_members: int
-    join_rules: Optional[str]
-    guest_access: Optional[str]
-    history_visibility: Optional[str]
+    join_rules: str | None
+    guest_access: str | None
+    history_visibility: str | None
     state_events: int
-    avatar: Optional[str]
-    topic: Optional[str]
-    room_type: Optional[str]
+    avatar: str | None
+    topic: str | None
+    room_type: str | None
 
 
 @attr.s(slots=True, frozen=True, auto_attribs=True)
 class RoomStats(LargestRoomStats):
     joined_local_members: int
-    version: Optional[str]
-    creator: Optional[str]
-    encryption: Optional[str]
+    version: str | None
+    creator: str | None
+    encryption: str | None
     federatable: bool
     public: bool
 
@@ -138,8 +132,8 @@ class RoomSortOrder(Enum):
 
 @attr.s(slots=True, frozen=True, auto_attribs=True)
 class PartialStateResyncInfo:
-    joined_via: Optional[str]
-    servers_in_room: Set[str] = attr.ib(factory=set)
+    joined_via: str | None
+    servers_in_room: set[str] = attr.ib(factory=set)
 
 
 class RoomWorkerStore(CacheInvalidationWorkerStore):
@@ -209,7 +203,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
             logger.error("store_room with room_id=%s failed: %s", room_id, e)
             raise StoreError(500, "Problem creating room.")
 
-    async def get_room(self, room_id: str) -> Optional[Tuple[bool, bool]]:
+    async def get_room(self, room_id: str) -> tuple[bool, bool] | None:
         """Retrieve a room.
 
         Args:
@@ -222,7 +216,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
             or None if the room is unknown.
         """
         row = cast(
-            Optional[Tuple[Optional[Union[int, bool]], Optional[Union[int, bool]]]],
+            tuple[int | bool | None, int | bool | None] | None,
             await self.db_pool.simple_select_one(
                 table="rooms",
                 keyvalues={"room_id": room_id},
@@ -235,7 +229,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
             return row
         return bool(row[0]), bool(row[1])
 
-    async def get_room_with_stats(self, room_id: str) -> Optional[RoomStats]:
+    async def get_room_with_stats(self, room_id: str) -> RoomStats | None:
         """Retrieve room with statistics.
 
         Args:
@@ -246,7 +240,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
 
         def get_room_with_stats_txn(
             txn: LoggingTransaction, room_id: str
-        ) -> Optional[RoomStats]:
+        ) -> RoomStats | None:
             sql = """
                 SELECT room_id, state.name, state.canonical_alias, curr.joined_members,
                   curr.local_users_in_room AS joined_local_members, rooms.room_version AS version,
@@ -287,7 +281,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
             "get_room_with_stats", get_room_with_stats_txn, room_id
         )
 
-    async def get_public_room_ids(self) -> List[str]:
+    async def get_public_room_ids(self) -> list[str]:
         return await self.db_pool.simple_select_onecol(
             table="rooms",
             keyvalues={"is_public": True},
@@ -296,8 +290,8 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
         )
 
     def _construct_room_type_where_clause(
-        self, room_types: Union[List[Union[str, None]], None]
-    ) -> Tuple[Union[str, None], list]:
+        self, room_types: list[str | None] | None
+    ) -> tuple[str | None, list]:
         if not room_types:
             return None, []
 
@@ -324,9 +318,9 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
 
     async def count_public_rooms(
         self,
-        network_tuple: Optional[ThirdPartyInstanceID],
+        network_tuple: ThirdPartyInstanceID | None,
         ignore_non_federatable: bool,
-        search_filter: Optional[dict],
+        search_filter: dict | None,
     ) -> int:
         """Counts the number of public rooms as tracked in the room_stats_current
         and room_stats_state table.
@@ -387,7 +381,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
             """
 
             txn.execute(sql, query_args)
-            return cast(Tuple[int], txn.fetchone())[0]
+            return cast(tuple[int], txn.fetchone())[0]
 
         return await self.db_pool.runInteraction(
             "count_public_rooms", _count_public_rooms_txn
@@ -399,20 +393,20 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
         def f(txn: LoggingTransaction) -> int:
             sql = "SELECT count(*)  FROM rooms"
             txn.execute(sql)
-            row = cast(Tuple[int], txn.fetchone())
+            row = cast(tuple[int], txn.fetchone())
             return row[0]
 
         return await self.db_pool.runInteraction("get_rooms", f)
 
     async def get_largest_public_rooms(
         self,
-        network_tuple: Optional[ThirdPartyInstanceID],
-        search_filter: Optional[dict],
-        limit: Optional[int],
-        bounds: Optional[Tuple[int, str]],
+        network_tuple: ThirdPartyInstanceID | None,
+        search_filter: dict | None,
+        limit: int | None,
+        bounds: tuple[int, str] | None,
         forwards: bool,
         ignore_non_federatable: bool = False,
-    ) -> List[LargestRoomStats]:
+    ) -> list[LargestRoomStats]:
         """Gets the largest public rooms (where largest is in terms of joined
         members, as tracked in the statistics table).
 
@@ -433,7 +427,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
         """
 
         where_clauses = []
-        query_args: List[Union[str, int]] = []
+        query_args: list[str | int] = []
 
         if network_tuple:
             if network_tuple.appservice_id:
@@ -549,7 +543,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
 
         def _get_largest_public_rooms_txn(
             txn: LoggingTransaction,
-        ) -> List[LargestRoomStats]:
+        ) -> list[LargestRoomStats]:
             txn.execute(sql, query_args)
 
             results = [
@@ -579,7 +573,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
         )
 
     @cached(max_entries=10000)
-    async def is_room_blocked(self, room_id: str) -> Optional[bool]:
+    async def is_room_blocked(self, room_id: str) -> bool | None:
         return await self.db_pool.simple_select_one_onecol(
             table="blocked_rooms",
             keyvalues={"room_id": room_id},
@@ -588,7 +582,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
             desc="is_room_blocked",
         )
 
-    async def room_is_blocked_by(self, room_id: str) -> Optional[str]:
+    async def room_is_blocked_by(self, room_id: str) -> str | None:
         """
         Function to retrieve user who has blocked the room.
         user_id is non-nullable
@@ -608,10 +602,10 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
         limit: int,
         order_by: str,
         reverse_order: bool,
-        search_term: Optional[str],
-        public_rooms: Optional[bool],
-        empty_rooms: Optional[bool],
-    ) -> Tuple[List[Dict[str, Any]], int]:
+        search_term: str | None,
+        public_rooms: bool | None,
+        empty_rooms: bool | None,
+    ) -> tuple[list[dict[str, Any]], int]:
         """Function to retrieve a paginated list of rooms as json.
 
         Args:
@@ -760,7 +754,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
 
         def _get_rooms_paginate_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[List[Dict[str, Any]], int]:
+        ) -> tuple[list[dict[str, Any]], int]:
             # Add the search term into the WHERE clause
             # and execute the data query
             txn.execute(info_sql, where_args + [limit, start])
@@ -795,7 +789,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
             # Add the search term into the WHERE clause if present
             txn.execute(count_sql, where_args)
 
-            room_count = cast(Tuple[int], txn.fetchone())
+            room_count = cast(tuple[int], txn.fetchone())
             return rooms, room_count[0]
 
         return await self.db_pool.runInteraction(
@@ -804,7 +798,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
         )
 
     @cached(max_entries=10000)
-    async def get_ratelimit_for_user(self, user_id: str) -> Optional[RatelimitOverride]:
+    async def get_ratelimit_for_user(self, user_id: str) -> RatelimitOverride | None:
         """Check if there are any overrides for ratelimiting for the given user
 
         Args:
@@ -909,7 +903,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
 
         def get_retention_policy_for_room_txn(
             txn: LoggingTransaction,
-        ) -> Optional[Tuple[Optional[int], Optional[int]]]:
+        ) -> tuple[int | None, int | None] | None:
             txn.execute(
                 """
                 SELECT min_lifetime, max_lifetime FROM room_retention
@@ -919,7 +913,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
                 (room_id,),
             )
 
-            return cast(Optional[Tuple[Optional[int], Optional[int]]], txn.fetchone())
+            return cast(tuple[int | None, int | None] | None, txn.fetchone())
 
         ret = await self.db_pool.runInteraction(
             "get_retention_policy_for_room",
@@ -951,7 +945,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
             max_lifetime=max_lifetime,
         )
 
-    async def get_media_mxcs_in_room(self, room_id: str) -> Tuple[List[str], List[str]]:
+    async def get_media_mxcs_in_room(self, room_id: str) -> tuple[list[str], list[str]]:
         """Retrieves all the local and remote media MXC URIs in a given room
 
         Args:
@@ -963,7 +957,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
 
         def _get_media_mxcs_in_room_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[List[str], List[str]]:
+        ) -> tuple[list[str], list[str]]:
             local_mxcs, remote_mxcs = self._get_media_mxcs_in_room_txn(txn, room_id)
             local_media_mxcs = []
             remote_media_mxcs = []
@@ -1001,7 +995,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
 
     def _get_media_mxcs_in_room_txn(
         self, txn: LoggingTransaction, room_id: str
-    ) -> Tuple[List[str], List[Tuple[str, str]]]:
+    ) -> tuple[list[str], list[tuple[str, str]]]:
         """Retrieves all the local and remote media MXC URIs in a given room
 
         Returns:
@@ -1062,7 +1056,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
         self,
         server_name: str,
         media_id: str,
-        quarantined_by: Optional[str],
+        quarantined_by: str | None,
     ) -> int:
         """quarantines or unquarantines a single local or remote media id
 
@@ -1107,7 +1101,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
 
     def _get_media_ids_by_user_txn(
         self, txn: LoggingTransaction, user_id: str, filter_quarantined: bool = True
-    ) -> List[str]:
+    ) -> list[str]:
         """Retrieves local media IDs by a given user
 
         Args:
@@ -1137,9 +1131,9 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
     def _quarantine_local_media_txn(
         self,
         txn: LoggingTransaction,
-        hashes: Set[str],
-        media_ids: Set[str],
-        quarantined_by: Optional[str],
+        hashes: set[str],
+        media_ids: set[str],
+        quarantined_by: str | None,
     ) -> int:
         """Quarantine and unquarantine local media items.
 
@@ -1192,9 +1186,9 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
     def _quarantine_remote_media_txn(
         self,
         txn: LoggingTransaction,
-        hashes: Set[str],
-        media: Set[Tuple[str, str]],
-        quarantined_by: Optional[str],
+        hashes: set[str],
+        media: set[tuple[str, str]],
+        quarantined_by: str | None,
     ) -> int:
         """Quarantine and unquarantine remote items
 
@@ -1240,9 +1234,9 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
     def _quarantine_media_txn(
         self,
         txn: LoggingTransaction,
-        local_mxcs: List[str],
-        remote_mxcs: List[Tuple[str, str]],
-        quarantined_by: Optional[str],
+        local_mxcs: list[str],
+        remote_mxcs: list[tuple[str, str]],
+        quarantined_by: str | None,
     ) -> int:
         """Quarantine and unquarantine local and remote media items
 
@@ -1345,8 +1339,8 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
         )
 
     async def get_rooms_for_retention_period_in_range(
-        self, min_ms: Optional[int], max_ms: Optional[int], include_null: bool = False
-    ) -> Dict[str, RetentionPolicy]:
+        self, min_ms: int | None, max_ms: int | None, include_null: bool = False
+    ) -> dict[str, RetentionPolicy]:
         """Retrieves all of the rooms within the given retention range.
 
         Optionally includes the rooms which don't have a retention policy.
@@ -1368,7 +1362,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
 
         def get_rooms_for_retention_period_in_range_txn(
             txn: LoggingTransaction,
-        ) -> Dict[str, RetentionPolicy]:
+        ) -> dict[str, RetentionPolicy]:
             range_conditions = []
             args = []
 
@@ -1425,7 +1419,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
 
     async def get_partial_state_servers_at_join(
         self, room_id: str
-    ) -> Optional[AbstractSet[str]]:
+    ) -> AbstractSet[str] | None:
         """Gets the set of servers in a partial state room at the time we joined it.
 
         Returns:
@@ -1464,10 +1458,10 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
             A dictionary of rooms with partial state, with room IDs as keys and
             lists of servers in rooms as values.
         """
-        room_servers: Dict[str, PartialStateResyncInfo] = {}
+        room_servers: dict[str, PartialStateResyncInfo] = {}
 
         rows = cast(
-            List[Tuple[str, str]],
+            list[tuple[str, str]],
             await self.db_pool.simple_select_list(
                 table="partial_state_rooms",
                 keyvalues={},
@@ -1480,7 +1474,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
             room_servers[room_id] = PartialStateResyncInfo(joined_via=joined_via)
 
         rows = cast(
-            List[Tuple[str, str]],
+            list[tuple[str, str]],
             await self.db_pool.simple_select_list(
                 "partial_state_rooms_servers",
                 keyvalues=None,
@@ -1533,7 +1527,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
         """
 
         rows = cast(
-            List[Tuple[str]],
+            list[tuple[str]],
             await self.db_pool.simple_select_many_batch(
                 table="partial_state_rooms",
                 column="room_id",
@@ -1571,7 +1565,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
 
     async def get_join_event_id_and_device_lists_stream_id_for_partial_state(
         self, room_id: str
-    ) -> Tuple[str, int]:
+    ) -> tuple[str, int]:
         """Get the event ID of the initial join that started the partial
         join, and the device list stream ID at the point we started the partial
         join.
@@ -1583,7 +1577,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
         """
 
         return cast(
-            Tuple[str, int],
+            tuple[str, int],
             await self.db_pool.simple_select_one(
                 table="partial_state_rooms",
                 keyvalues={"room_id": room_id},
@@ -1602,7 +1596,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
 
     async def get_un_partial_stated_rooms_between(
         self, last_id: int, current_id: int, room_ids: Collection[str]
-    ) -> Set[str]:
+    ) -> set[str]:
         """Get all rooms that got un partial stated between `last_id` exclusive and
         `current_id` inclusive.
 
@@ -1615,7 +1609,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
 
         def _get_un_partial_stated_rooms_between_txn(
             txn: LoggingTransaction,
-        ) -> Set[str]:
+        ) -> set[str]:
             sql = """
                 SELECT DISTINCT room_id FROM un_partial_stated_room_stream
                 WHERE ? < stream_id AND stream_id <= ? AND
@@ -1636,7 +1630,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
 
     async def get_un_partial_stated_rooms_from_stream(
         self, instance_name: str, last_id: int, current_id: int, limit: int
-    ) -> Tuple[List[Tuple[int, Tuple[str]]], int, bool]:
+    ) -> tuple[list[tuple[int, tuple[str]]], int, bool]:
         """Get updates for un partial stated rooms replication stream.
 
         Args:
@@ -1663,7 +1657,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
 
         def get_un_partial_stated_rooms_from_stream_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[List[Tuple[int, Tuple[str]]], int, bool]:
+        ) -> tuple[list[tuple[int, tuple[str]]], int, bool]:
             sql = """
                 SELECT stream_id, room_id
                 FROM un_partial_stated_room_stream
@@ -1686,7 +1680,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
             get_un_partial_stated_rooms_from_stream_txn,
         )
 
-    async def get_event_report(self, report_id: int) -> Optional[Dict[str, Any]]:
+    async def get_event_report(self, report_id: int) -> dict[str, Any] | None:
         """Retrieve an event report
 
         Args:
@@ -1698,7 +1692,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
 
         def _get_event_report_txn(
             txn: LoggingTransaction, report_id: int
-        ) -> Optional[Dict[str, Any]]:
+        ) -> dict[str, Any] | None:
             sql = """
                 SELECT
                     er.id,
@@ -1752,10 +1746,10 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
         start: int,
         limit: int,
         direction: Direction = Direction.BACKWARDS,
-        user_id: Optional[str] = None,
-        room_id: Optional[str] = None,
-        event_sender_user_id: Optional[str] = None,
-    ) -> Tuple[List[Dict[str, Any]], int]:
+        user_id: str | None = None,
+        room_id: str | None = None,
+        event_sender_user_id: str | None = None,
+    ) -> tuple[list[dict[str, Any]], int]:
         """Retrieve a paginated list of event reports
 
         Args:
@@ -1775,9 +1769,9 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
 
         def _get_event_reports_paginate_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[List[Dict[str, Any]], int]:
+        ) -> tuple[list[dict[str, Any]], int]:
             filters = []
-            args: List[object] = []
+            args: list[object] = []
 
             if user_id:
                 filters.append("er.user_id LIKE ?")
@@ -1810,7 +1804,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
                 {}
                 """.format(where_clause)
             txn.execute(sql, args)
-            count = cast(Tuple[int], txn.fetchone())[0]
+            count = cast(tuple[int], txn.fetchone())[0]
 
             sql = """
                 SELECT
@@ -2214,7 +2208,7 @@ class RoomBackgroundUpdateStore(RoomWorkerStore):
 
         last_room = progress.get("room_id", "")
 
-        def _get_rooms(txn: LoggingTransaction) -> List[str]:
+        def _get_rooms(txn: LoggingTransaction) -> list[str]:
             txn.execute(
                 """
                 SELECT room_id
@@ -2460,7 +2454,7 @@ class RoomStore(RoomBackgroundUpdateStore, RoomWorkerStore):
         self._instance_name = hs.get_instance_name()
 
     async def upsert_room_on_join(
-        self, room_id: str, room_version: RoomVersion, state_events: List[EventBase]
+        self, room_id: str, room_version: RoomVersion, state_events: list[EventBase]
     ) -> None:
         """Ensure that the room is stored in the table
 
@@ -2606,7 +2600,7 @@ class RoomStore(RoomBackgroundUpdateStore, RoomWorkerStore):
         room_id: str,
         event_id: str,
         user_id: str,
-        reason: Optional[str],
+        reason: str | None,
         content: JsonDict,
         received_ts: int,
     ) -> int:
@@ -2700,7 +2694,7 @@ class RoomStore(RoomBackgroundUpdateStore, RoomWorkerStore):
         )
         return next_id
 
-    async def clear_partial_state_room(self, room_id: str) -> Optional[int]:
+    async def clear_partial_state_room(self, room_id: str) -> int | None:
         """Clears the partial state flag for a room.
 
         Args:
diff --git a/synapse/storage/databases/main/roommember.py b/synapse/storage/databases/main/roommember.py
index 9db2e14a06..4fb7779d38 100644
--- a/synapse/storage/databases/main/roommember.py
+++ b/synapse/storage/databases/main/roommember.py
@@ -24,16 +24,9 @@ from typing import (
     TYPE_CHECKING,
     AbstractSet,
     Collection,
-    Dict,
-    FrozenSet,
     Iterable,
-    List,
     Mapping,
-    Optional,
     Sequence,
-    Set,
-    Tuple,
-    Union,
     cast,
 )
 
@@ -187,7 +180,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
             desc="get_users_in_room",
         )
 
-    def get_users_in_room_txn(self, txn: LoggingTransaction, room_id: str) -> List[str]:
+    def get_users_in_room_txn(self, txn: LoggingTransaction, room_id: str) -> list[str]:
         """Returns a list of users in the room."""
 
         return self.db_pool.simple_select_onecol_txn(
@@ -242,7 +235,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
         def _get_subset_users_in_room_with_profiles(
             txn: LoggingTransaction,
-        ) -> Dict[str, ProfileInfo]:
+        ) -> dict[str, ProfileInfo]:
             clause, ids = make_in_list_sql_clause(
                 self.database_engine, "c.state_key", user_ids
             )
@@ -287,7 +280,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
         def _get_users_in_room_with_profiles(
             txn: LoggingTransaction,
-        ) -> Dict[str, ProfileInfo]:
+        ) -> dict[str, ProfileInfo]:
             sql = """
                 SELECT state_key, display_name, avatar_url FROM room_memberships as m
                 INNER JOIN current_state_events as c
@@ -328,14 +321,14 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
         def _get_room_summary_txn(
             txn: LoggingTransaction,
-        ) -> Dict[str, MemberSummary]:
+        ) -> dict[str, MemberSummary]:
             # first get counts.
             # We do this all in one transaction to keep the cache small.
             # FIXME: get rid of this when we have room_stats
 
             counts = self._get_member_counts_txn(txn, room_id)
 
-            res: Dict[str, MemberSummary] = {}
+            res: dict[str, MemberSummary] = {}
             for membership, count in counts.items():
                 res.setdefault(membership, MemberSummary([], count))
 
@@ -392,7 +385,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
     def _get_member_counts_txn(
         self, txn: LoggingTransaction, room_id: str
-    ) -> Dict[str, int]:
+    ) -> dict[str, int]:
         """Get a mapping of number of users by membership"""
 
         # Note, rejected events will have a null membership field, so
@@ -451,7 +444,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
     async def get_invite_for_local_user_in_room(
         self, user_id: str, room_id: str
-    ) -> Optional[RoomsForUser]:
+    ) -> RoomsForUser | None:
         """Gets the invite for the given *local* user and room.
 
         Args:
@@ -473,7 +466,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
         user_id: str,
         membership_list: Collection[str],
         excluded_rooms: StrCollection = (),
-    ) -> List[RoomsForUser]:
+    ) -> list[RoomsForUser]:
         """Get all the rooms for this *local* user where the membership for this user
         matches one in the membership list.
 
@@ -536,8 +529,8 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
         self,
         txn: LoggingTransaction,
         user_id: str,
-        membership_list: List[str],
-    ) -> List[RoomsForUser]:
+        membership_list: list[str],
+    ) -> list[RoomsForUser]:
         """Get all the rooms for this *local* user where the membership for this user
         matches one in the membership list.
 
@@ -603,12 +596,12 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
     async def get_local_users_related_to_room(
         self, room_id: str
-    ) -> List[Tuple[str, str]]:
+    ) -> list[tuple[str, str]]:
         """
         Retrieves a list of the current roommembers who are local to the server and their membership status.
         """
         return cast(
-            List[Tuple[str, str]],
+            list[tuple[str, str]],
             await self.db_pool.simple_select_list(
                 table="local_current_membership",
                 keyvalues={"room_id": room_id},
@@ -660,7 +653,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
     async def get_local_current_membership_for_user_in_room(
         self, user_id: str, room_id: str
-    ) -> Tuple[Optional[str], Optional[str]]:
+    ) -> tuple[str | None, str | None]:
         """Retrieve the current local membership state and event ID for a user in a room.
 
         Args:
@@ -677,7 +670,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
             raise SynapseError(HTTPStatus.BAD_REQUEST, message, errcode=Codes.BAD_JSON)
 
         results = cast(
-            Optional[Tuple[str, str]],
+            tuple[str, str] | None,
             await self.db_pool.simple_select_one(
                 "local_current_membership",
                 {"room_id": room_id, "user_id": user_id},
@@ -693,7 +686,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
     async def get_users_server_still_shares_room_with(
         self, user_ids: Collection[str]
-    ) -> Set[str]:
+    ) -> set[str]:
         """Given a list of users return the set that the server still share a
         room with.
         """
@@ -711,7 +704,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
         self,
         txn: LoggingTransaction,
         user_ids: Collection[str],
-    ) -> Set[str]:
+    ) -> set[str]:
         if not user_ids:
             return set()
 
@@ -734,7 +727,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
     async def get_rooms_user_currently_banned_from(
         self, user_id: str
-    ) -> FrozenSet[str]:
+    ) -> frozenset[str]:
         """Returns a set of room_ids the user is currently banned from.
 
         If a remote user only returns rooms this server is currently
@@ -754,7 +747,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
         return frozenset(room_ids)
 
     @cached(max_entries=500000, iterable=True)
-    async def get_rooms_for_user(self, user_id: str) -> FrozenSet[str]:
+    async def get_rooms_for_user(self, user_id: str) -> frozenset[str]:
         """Returns a set of room_ids the user is currently joined to.
 
         If a remote user only returns rooms this server is currently
@@ -780,7 +773,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
     )
     async def _get_rooms_for_users(
         self, user_ids: Collection[str]
-    ) -> Mapping[str, FrozenSet[str]]:
+    ) -> Mapping[str, frozenset[str]]:
         """A batched version of `get_rooms_for_user`.
 
         Returns:
@@ -788,7 +781,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
         """
 
         rows = cast(
-            List[Tuple[str, str]],
+            list[tuple[str, str]],
             await self.db_pool.simple_select_many_batch(
                 table="current_state_events",
                 column="state_key",
@@ -805,7 +798,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
             ),
         )
 
-        user_rooms: Dict[str, Set[str]] = {user_id: set() for user_id in user_ids}
+        user_rooms: dict[str, set[str]] = {user_id: set() for user_id in user_ids}
 
         for state_key, room_id in rows:
             user_rooms[state_key].add(room_id)
@@ -814,11 +807,11 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
     async def get_rooms_for_users(
         self, user_ids: Collection[str]
-    ) -> Dict[str, FrozenSet[str]]:
+    ) -> dict[str, frozenset[str]]:
         """A batched wrapper around `_get_rooms_for_users`, to prevent locking
         other calls to `get_rooms_for_user` for large user lists.
         """
-        all_user_rooms: Dict[str, FrozenSet[str]] = {}
+        all_user_rooms: dict[str, frozenset[str]] = {}
 
         # 250 users is pretty arbitrary but the data can be quite large if users
         # are in many rooms.
@@ -838,7 +831,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
     )
     async def _do_users_share_a_room(
         self, user_id: str, other_user_ids: Collection[str]
-    ) -> Mapping[str, Optional[bool]]:
+    ) -> Mapping[str, bool | None]:
         """Return mapping from user ID to whether they share a room with the
         given user.
 
@@ -848,7 +841,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
         def do_users_share_a_room_txn(
             txn: LoggingTransaction, user_ids: Collection[str]
-        ) -> Dict[str, bool]:
+        ) -> dict[str, bool]:
             clause, args = make_in_list_sql_clause(
                 self.database_engine, "state_key", user_ids
             )
@@ -882,7 +875,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
     async def do_users_share_a_room(
         self, user_id: str, other_user_ids: Collection[str]
-    ) -> Set[str]:
+    ) -> set[str]:
         """Return the set of users who share a room with the first users"""
 
         user_dict = await self._do_users_share_a_room(user_id, other_user_ids)
@@ -901,7 +894,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
     )
     async def _do_users_share_a_room_joined_or_invited(
         self, user_id: str, other_user_ids: Collection[str]
-    ) -> Mapping[str, Optional[bool]]:
+    ) -> Mapping[str, bool | None]:
         """Return mapping from user ID to whether they share a room with the
         given user via being either joined or invited.
 
@@ -911,7 +904,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
         def do_users_share_a_room_joined_or_invited_txn(
             txn: LoggingTransaction, user_ids: Collection[str]
-        ) -> Dict[str, bool]:
+        ) -> dict[str, bool]:
             clause, args = make_in_list_sql_clause(
                 self.database_engine, "state_key", user_ids
             )
@@ -947,7 +940,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
     async def do_users_share_a_room_joined_or_invited(
         self, user_id: str, other_user_ids: Collection[str]
-    ) -> Set[str]:
+    ) -> set[str]:
         """Return the set of users who share a room with the first users via being either joined or invited"""
 
         user_dict = await self._do_users_share_a_room_joined_or_invited(
@@ -956,11 +949,11 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
         return {u for u, share_room in user_dict.items() if share_room}
 
-    async def get_users_who_share_room_with_user(self, user_id: str) -> Set[str]:
+    async def get_users_who_share_room_with_user(self, user_id: str) -> set[str]:
         """Returns the set of users who share a room with `user_id`"""
         room_ids = await self.get_rooms_for_user(user_id)
 
-        user_who_share_room: Set[str] = set()
+        user_who_share_room: set[str] = set()
         for room_id in room_ids:
             user_ids = await self.get_users_in_room(room_id)
             user_who_share_room.update(user_ids)
@@ -969,8 +962,8 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
     @cached(cache_context=True, iterable=True)
     async def get_mutual_rooms_between_users(
-        self, user_ids: FrozenSet[str], cache_context: _CacheContext
-    ) -> FrozenSet[str]:
+        self, user_ids: frozenset[str], cache_context: _CacheContext
+    ) -> frozenset[str]:
         """
         Returns the set of rooms that all users in `user_ids` share.
 
@@ -979,7 +972,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
               overlapping joined rooms for.
             cache_context
         """
-        shared_room_ids: Optional[FrozenSet[str]] = None
+        shared_room_ids: frozenset[str] | None = None
         for user_id in user_ids:
             room_ids = await self.get_rooms_for_user(
                 user_id, on_invalidate=cache_context.invalidate
@@ -993,7 +986,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
     async def get_joined_user_ids_from_state(
         self, room_id: str, state: StateMap[str]
-    ) -> Set[str]:
+    ) -> set[str]:
         """
         For a given set of state IDs, get a set of user IDs in the room.
 
@@ -1002,7 +995,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
         """
 
         with Measure(
-            self._clock,
+            self.clock,
             name="get_joined_user_ids_from_state",
             server_name=self.server_name,
         ):
@@ -1050,7 +1043,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
     )
     def _get_user_id_from_membership_event_id(
         self, event_id: str
-    ) -> Optional[Tuple[str, ProfileInfo]]:
+    ) -> tuple[str, ProfileInfo] | None:
         raise NotImplementedError()
 
     @cachedList(
@@ -1059,7 +1052,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
     )
     async def _get_user_ids_from_membership_event_ids(
         self, event_ids: Iterable[str]
-    ) -> Mapping[str, Optional[str]]:
+    ) -> Mapping[str, str | None]:
         """For given set of member event_ids check if they point to a join
         event.
 
@@ -1071,7 +1064,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
         """
 
         rows = cast(
-            List[Tuple[str, str]],
+            list[tuple[str, str]],
             await self.db_pool.simple_select_many_batch(
                 table="room_memberships",
                 column="event_id",
@@ -1148,7 +1141,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
         # For PostgreSQL we can use a regex to pull out the domains from the
         # joined users in `current_state_events` via regex.
 
-        def get_current_hosts_in_room_txn(txn: LoggingTransaction) -> Set[str]:
+        def get_current_hosts_in_room_txn(txn: LoggingTransaction) -> set[str]:
             sql = """
                 SELECT DISTINCT substring(state_key FROM '@[^:]*:(.*)$')
                 FROM current_state_events
@@ -1165,7 +1158,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
         )
 
     @cached(iterable=True, max_entries=10000)
-    async def get_current_hosts_in_room_ordered(self, room_id: str) -> Tuple[str, ...]:
+    async def get_current_hosts_in_room_ordered(self, room_id: str) -> tuple[str, ...]:
         """
         Get current hosts in room based on current state.
 
@@ -1201,7 +1194,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
         def get_current_hosts_in_room_ordered_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[str, ...]:
+        ) -> tuple[str, ...]:
             # Returns a list of servers currently joined in the room sorted by
             # longest in the room first (aka. with the lowest depth). The
             # heuristic of sorting by servers who have been in the room the
@@ -1234,7 +1227,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
     async def _get_approximate_current_memberships_in_room(
         self, room_id: str
-    ) -> Mapping[str, Optional[str]]:
+    ) -> Mapping[str, str | None]:
         """Build a map from event id to membership, for all events in the current state.
 
         The event ids of non-memberships events (e.g. `m.room.power_levels`) are present
@@ -1245,7 +1238,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
         """
 
         rows = cast(
-            List[Tuple[str, Optional[str]]],
+            list[tuple[str, str | None]],
             await self.db_pool.simple_select_list(
                 "current_state_events",
                 keyvalues={"room_id": room_id},
@@ -1297,7 +1290,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
             The forgotten rooms.
         """
 
-        def _get_forgotten_rooms_for_user_txn(txn: LoggingTransaction) -> Set[str]:
+        def _get_forgotten_rooms_for_user_txn(txn: LoggingTransaction) -> set[str]:
             # This is a slightly convoluted query that first looks up all rooms
             # that the user has forgotten in the past, then rechecks that list
             # to see if any have subsequently been updated. This is done so that
@@ -1348,7 +1341,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
         # If any rows still exist it means someone has not forgotten this room yet
         return not rows[0][0]
 
-    async def get_rooms_user_has_been_in(self, user_id: str) -> Set[str]:
+    async def get_rooms_user_has_been_in(self, user_id: str) -> set[str]:
         """Get all rooms that the user has ever been in.
 
         Args:
@@ -1369,7 +1362,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
     async def get_membership_event_ids_for_user(
         self, user_id: str, room_id: str
-    ) -> Set[str]:
+    ) -> set[str]:
         """Get all event_ids for the given user and room.
 
         Args:
@@ -1392,7 +1385,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
     @cached(max_entries=5000)
     async def _get_membership_from_event_id(
         self, member_event_id: str
-    ) -> Optional[EventIdMembership]:
+    ) -> EventIdMembership | None:
         raise NotImplementedError()
 
     @cachedList(
@@ -1400,7 +1393,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
     )
     async def get_membership_from_event_ids(
         self, member_event_ids: Iterable[str]
-    ) -> Mapping[str, Optional[EventIdMembership]]:
+    ) -> Mapping[str, EventIdMembership | None]:
         """Get user_id and membership of a set of event IDs.
 
         Returns:
@@ -1409,7 +1402,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
         """
 
         rows = cast(
-            List[Tuple[str, str, str]],
+            list[tuple[str, str, str]],
             await self.db_pool.simple_select_many_batch(
                 table="room_memberships",
                 column="event_id",
@@ -1533,7 +1526,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
         def _txn(
             txn: LoggingTransaction,
-        ) -> Dict[str, RoomsForUserSlidingSync]:
+        ) -> dict[str, RoomsForUserSlidingSync]:
             # XXX: If you use any new columns that can change (like from
             # `sliding_sync_joined_rooms` or `forgotten`), make sure to bust the
             # `get_sliding_sync_rooms_for_user_from_membership_snapshots` cache in the
@@ -1582,7 +1575,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
         self,
         user_id: str,
         to_token: StreamToken,
-    ) -> Dict[str, RoomsForUserSlidingSync]:
+    ) -> dict[str, RoomsForUserSlidingSync]:
         """
         Get all the self-leave rooms for a user after the `to_token` (outside the token
         range) that are potentially relevant[1] and needed to handle a sliding sync
@@ -1614,7 +1607,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
         def _txn(
             txn: LoggingTransaction,
-        ) -> Dict[str, RoomsForUserSlidingSync]:
+        ) -> dict[str, RoomsForUserSlidingSync]:
             sql = """
                 SELECT m.room_id, m.sender, m.membership, m.membership_event_id,
                     r.room_version,
@@ -1641,7 +1634,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
             txn.execute(sql, (user_id, min_to_token_position))
 
             # Map from room_id to membership info
-            room_membership_for_user_map: Dict[str, RoomsForUserSlidingSync] = {}
+            room_membership_for_user_map: dict[str, RoomsForUserSlidingSync] = {}
             for row in txn:
                 room_for_user = RoomsForUserSlidingSync(
                     room_id=row[0],
@@ -1685,12 +1678,12 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
     async def get_sliding_sync_room_for_user(
         self, user_id: str, room_id: str
-    ) -> Optional[RoomsForUserSlidingSync]:
+    ) -> RoomsForUserSlidingSync | None:
         """Get the sliding sync room entry for the given user and room."""
 
         def get_sliding_sync_room_for_user_txn(
             txn: LoggingTransaction,
-        ) -> Optional[RoomsForUserSlidingSync]:
+        ) -> RoomsForUserSlidingSync | None:
             sql = """
                 SELECT m.room_id, m.sender, m.membership, m.membership_event_id,
                     r.room_version,
@@ -1728,7 +1721,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
     async def get_sliding_sync_room_for_user_batch(
         self, user_id: str, room_ids: StrCollection
-    ) -> Dict[str, RoomsForUserSlidingSync]:
+    ) -> dict[str, RoomsForUserSlidingSync]:
         """Get the sliding sync room entry for the given user and rooms."""
 
         if not room_ids:
@@ -1736,7 +1729,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
         def get_sliding_sync_room_for_user_batch_txn(
             txn: LoggingTransaction,
-        ) -> Dict[str, RoomsForUserSlidingSync]:
+        ) -> dict[str, RoomsForUserSlidingSync]:
             clause, args = make_in_list_sql_clause(
                 self.database_engine, "m.room_id", room_ids
             )
@@ -1779,7 +1772,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
     async def get_rooms_for_user_by_date(
         self, user_id: str, from_ts: int
-    ) -> FrozenSet[str]:
+    ) -> frozenset[str]:
         """
         Fetch a list of rooms that the user has joined at or after the given timestamp, including
         those they subsequently have left/been banned from.
@@ -1993,7 +1986,7 @@ class RoomMemberBackgroundUpdateStore(SQLBaseStore):
 
         def _background_current_state_membership_txn(
             txn: LoggingTransaction, last_processed_room: str
-        ) -> Tuple[int, bool]:
+        ) -> tuple[int, bool]:
             processed = 0
             while processed < batch_size:
                 txn.execute(
@@ -2063,7 +2056,7 @@ class RoomMemberStore(
 
 def extract_heroes_from_room_summary(
     details: Mapping[str, MemberSummary], me: str
-) -> List[str]:
+) -> list[str]:
     """Determine the users that represent a room, from the perspective of the `me` user.
 
     This function expects `MemberSummary.members` to already be sorted by
@@ -2105,13 +2098,13 @@ class _JoinedHostsCache:
     """The cached data used by the `_get_joined_hosts_cache`."""
 
     # Dict of host to the set of their users in the room at the state group.
-    hosts_to_joined_users: Dict[str, Set[str]] = attr.Factory(dict)
+    hosts_to_joined_users: dict[str, set[str]] = attr.Factory(dict)
 
     # The state group `hosts_to_joined_users` is derived from. Will be an object
     # if the instance is newly created or if the state is not based on a state
     # group. (An object is used as a sentinel value to ensure that it never is
     # equal to anything else).
-    state_group: Union[object, int] = attr.Factory(object)
+    state_group: object | int = attr.Factory(object)
 
     def __len__(self) -> int:
         return sum(len(v) for v in self.hosts_to_joined_users.values())
diff --git a/synapse/storage/databases/main/search.py b/synapse/storage/databases/main/search.py
index 47dfdf64e5..d6eace5efa 100644
--- a/synapse/storage/databases/main/search.py
+++ b/synapse/storage/databases/main/search.py
@@ -28,11 +28,6 @@ from typing import (
     Any,
     Collection,
     Iterable,
-    List,
-    Optional,
-    Set,
-    Tuple,
-    Union,
     cast,
 )
 
@@ -63,7 +58,7 @@ class SearchEntry:
     value: str
     event_id: str
     room_id: str
-    stream_ordering: Optional[int]
+    stream_ordering: int | None
     origin_server_ts: int
 
 
@@ -362,7 +357,7 @@ class SearchBackgroundUpdateStore(SearchWorkerStore):
                 pg,
             )
 
-        def reindex_search_txn(txn: LoggingTransaction) -> Tuple[int, bool]:
+        def reindex_search_txn(txn: LoggingTransaction) -> tuple[int, bool]:
             sql = """
             UPDATE event_search AS es
             SET stream_ordering = e.stream_ordering, origin_server_ts = e.origin_server_ts
@@ -451,7 +446,7 @@ class SearchStore(SearchBackgroundUpdateStore):
         """
         clauses = []
 
-        args: List[Any] = []
+        args: list[Any] = []
 
         # Make sure we don't explode because the person is in too many rooms.
         # We filter the results below regardless.
@@ -471,7 +466,7 @@ class SearchStore(SearchBackgroundUpdateStore):
         count_args = args
         count_clauses = clauses
 
-        sqlite_highlights: List[str] = []
+        sqlite_highlights: list[str] = []
 
         if isinstance(self.database_engine, PostgresEngine):
             search_query = search_term
@@ -519,7 +514,7 @@ class SearchStore(SearchBackgroundUpdateStore):
 
         # List of tuples of (rank, room_id, event_id).
         results = cast(
-            List[Tuple[Union[int, float], str, str]],
+            list[tuple[int | float, str, str]],
             await self.db_pool.execute("search_msgs", sql, *args),
         )
 
@@ -544,7 +539,7 @@ class SearchStore(SearchBackgroundUpdateStore):
 
         # List of tuples of (room_id, count).
         count_results = cast(
-            List[Tuple[str, int]],
+            list[tuple[str, int]],
             await self.db_pool.execute("search_rooms_count", count_sql, *count_args),
         )
 
@@ -565,7 +560,7 @@ class SearchStore(SearchBackgroundUpdateStore):
         search_term: str,
         keys: Iterable[str],
         limit: int,
-        pagination_token: Optional[str] = None,
+        pagination_token: str | None = None,
     ) -> JsonDict:
         """Performs a full text search over events with given keys.
 
@@ -580,7 +575,7 @@ class SearchStore(SearchBackgroundUpdateStore):
             Each match as a dictionary.
         """
         clauses = []
-        args: List[Any] = []
+        args: list[Any] = []
 
         # Make sure we don't explode because the person is in too many rooms.
         # We filter the results below regardless.
@@ -602,7 +597,7 @@ class SearchStore(SearchBackgroundUpdateStore):
         count_args = list(args)
         count_clauses = list(clauses)
 
-        sqlite_highlights: List[str] = []
+        sqlite_highlights: list[str] = []
 
         if pagination_token:
             try:
@@ -686,7 +681,7 @@ class SearchStore(SearchBackgroundUpdateStore):
 
         # List of tuples of (rank, room_id, event_id, origin_server_ts, stream_ordering).
         results = cast(
-            List[Tuple[Union[int, float], str, str, int, int]],
+            list[tuple[int | float, str, str, int, int]],
             await self.db_pool.execute("search_rooms", sql, *args),
         )
 
@@ -711,7 +706,7 @@ class SearchStore(SearchBackgroundUpdateStore):
 
         # List of tuples of (room_id, count).
         count_results = cast(
-            List[Tuple[str, int]],
+            list[tuple[str, int]],
             await self.db_pool.execute("search_rooms_count", count_sql, *count_args),
         )
 
@@ -732,8 +727,8 @@ class SearchStore(SearchBackgroundUpdateStore):
         }
 
     async def _find_highlights_in_postgres(
-        self, search_query: str, events: List[EventBase]
-    ) -> Set[str]:
+        self, search_query: str, events: list[EventBase]
+    ) -> set[str]:
         """Given a list of events and a search term, return a list of words
         that match from the content of the event.
 
@@ -748,7 +743,7 @@ class SearchStore(SearchBackgroundUpdateStore):
             A set of strings.
         """
 
-        def f(txn: LoggingTransaction) -> Set[str]:
+        def f(txn: LoggingTransaction) -> set[str]:
             highlight_words = set()
             for event in events:
                 # As a hack we simply join values of all possible keys. This is
@@ -811,7 +806,7 @@ def _to_postgres_options(options_dict: JsonDict) -> str:
 
 @dataclass
 class Phrase:
-    phrase: List[str]
+    phrase: list[str]
 
 
 class SearchToken(enum.Enum):
@@ -820,8 +815,8 @@ class SearchToken(enum.Enum):
     And = enum.auto()
 
 
-Token = Union[str, Phrase, SearchToken]
-TokenList = List[Token]
+Token = str | Phrase | SearchToken
+TokenList = list[Token]
 
 
 def _is_stop_word(word: str) -> bool:
@@ -901,7 +896,7 @@ def _tokenize_query(query: str) -> TokenList:
     return tokens
 
 
-def _tokens_to_sqlite_match_query(tokens: TokenList) -> Tuple[str, List[str]]:
+def _tokens_to_sqlite_match_query(tokens: TokenList) -> tuple[str, list[str]]:
     """
     Convert the list of tokens to a string suitable for passing to sqlite's MATCH.
     Assume sqlite was compiled with enhanced query syntax.
@@ -934,7 +929,7 @@ def _tokens_to_sqlite_match_query(tokens: TokenList) -> Tuple[str, List[str]]:
     return "".join(match_query), highlights
 
 
-def _parse_query_for_sqlite(search_term: str) -> Tuple[str, List[str]]:
+def _parse_query_for_sqlite(search_term: str) -> tuple[str, list[str]]:
     """Takes a plain unicode string from the user and converts it into a form
     that can be passed to sqllite's matchinfo().
 
diff --git a/synapse/storage/databases/main/session.py b/synapse/storage/databases/main/session.py
index 8a5fa8386c..1154bb2d59 100644
--- a/synapse/storage/databases/main/session.py
+++ b/synapse/storage/databases/main/session.py
@@ -55,7 +55,7 @@ class SessionStore(SQLBaseStore):
 
         # Create a background job for culling expired sessions.
         if hs.config.worker.run_background_tasks:
-            self._clock.looping_call(self._delete_expired_sessions, 30 * 60 * 1000)
+            self.clock.looping_call(self._delete_expired_sessions, 30 * 60 * 1000)
 
     async def create_session(
         self, session_type: str, value: JsonDict, expiry_ms: int
@@ -133,7 +133,7 @@ class SessionStore(SQLBaseStore):
             _get_session,
             session_type,
             session_id,
-            self._clock.time_msec(),
+            self.clock.time_msec(),
         )
 
     @wrap_as_background_process("delete_expired_sessions")
@@ -147,5 +147,5 @@ class SessionStore(SQLBaseStore):
         await self.db_pool.runInteraction(
             "delete_expired_sessions",
             _delete_expired_sessions_txn,
-            self._clock.time_msec(),
+            self.clock.time_msec(),
         )
diff --git a/synapse/storage/databases/main/signatures.py b/synapse/storage/databases/main/signatures.py
index ef86151e31..8072a8c741 100644
--- a/synapse/storage/databases/main/signatures.py
+++ b/synapse/storage/databases/main/signatures.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import Collection, Dict, List, Mapping, Tuple
+from typing import Collection, Mapping
 
 from unpaddedbase64 import encode_base64
 
@@ -59,7 +59,7 @@ class SignatureWorkerStore(EventsWorkerStore):
             allow_rejected=True,
         )
 
-        hashes: Dict[str, Dict[str, bytes]] = {}
+        hashes: dict[str, dict[str, bytes]] = {}
         for event_id in event_ids:
             event = events.get(event_id)
             if event is None:
@@ -72,7 +72,7 @@ class SignatureWorkerStore(EventsWorkerStore):
 
     async def add_event_hashes(
         self, event_ids: Collection[str]
-    ) -> List[Tuple[str, Dict[str, str]]]:
+    ) -> list[tuple[str, dict[str, str]]]:
         """
 
         Args:
diff --git a/synapse/storage/databases/main/sliding_sync.py b/synapse/storage/databases/main/sliding_sync.py
index f7af3e88d3..2b67e75ac4 100644
--- a/synapse/storage/databases/main/sliding_sync.py
+++ b/synapse/storage/databases/main/sliding_sync.py
@@ -14,7 +14,7 @@
 
 
 import logging
-from typing import TYPE_CHECKING, Dict, List, Mapping, Optional, Set, cast
+from typing import TYPE_CHECKING, Mapping, cast
 
 import attr
 
@@ -79,7 +79,7 @@ class SlidingSyncStore(SQLBaseStore):
     async def get_latest_bump_stamp_for_room(
         self,
         room_id: str,
-    ) -> Optional[int]:
+    ) -> int | None:
         """
         Get the `bump_stamp` for the room.
 
@@ -99,7 +99,7 @@ class SlidingSyncStore(SQLBaseStore):
         """
 
         return cast(
-            Optional[int],
+            int | None,
             await self.db_pool.simple_select_one_onecol(
                 table="sliding_sync_joined_rooms",
                 keyvalues={"room_id": room_id},
@@ -121,7 +121,7 @@ class SlidingSyncStore(SQLBaseStore):
         user_id: str,
         device_id: str,
         conn_id: str,
-        previous_connection_position: Optional[int],
+        previous_connection_position: int | None,
         per_connection_state: "MutablePerConnectionState",
     ) -> int:
         """Persist updates to the per-connection state for a sliding sync
@@ -154,7 +154,7 @@ class SlidingSyncStore(SQLBaseStore):
         user_id: str,
         device_id: str,
         conn_id: str,
-        previous_connection_position: Optional[int],
+        previous_connection_position: int | None,
         per_connection_state: "PerConnectionStateDB",
     ) -> int:
         # First we fetch (or create) the connection key associated with the
@@ -201,7 +201,7 @@ class SlidingSyncStore(SQLBaseStore):
                     "user_id": user_id,
                     "effective_device_id": device_id,
                     "conn_id": conn_id,
-                    "created_ts": self._clock.time_msec(),
+                    "created_ts": self.clock.time_msec(),
                 },
                 returning=("connection_key",),
             )
@@ -212,7 +212,7 @@ class SlidingSyncStore(SQLBaseStore):
             table="sliding_sync_connection_positions",
             values={
                 "connection_key": connection_key,
-                "created_ts": self._clock.time_msec(),
+                "created_ts": self.clock.time_msec(),
             },
             returning=("connection_position",),
         )
@@ -222,7 +222,7 @@ class SlidingSyncStore(SQLBaseStore):
         # with the updates to `required_state`
 
         # Dict from required state json -> required state ID
-        required_state_to_id: Dict[str, int] = {}
+        required_state_to_id: dict[str, int] = {}
         if previous_connection_position is not None:
             rows = self.db_pool.simple_select_list_txn(
                 txn,
@@ -233,8 +233,8 @@ class SlidingSyncStore(SQLBaseStore):
             for required_state_id, required_state in rows:
                 required_state_to_id[required_state] = required_state_id
 
-        room_to_state_ids: Dict[str, int] = {}
-        unique_required_state: Dict[str, List[str]] = {}
+        room_to_state_ids: dict[str, int] = {}
+        unique_required_state: dict[str, list[str]] = {}
         for room_id, room_state in per_connection_state.room_configs.items():
             serialized_state = json_encoder.encode(
                 # We store the required state as a sorted list of event type /
@@ -418,7 +418,7 @@ class SlidingSyncStore(SQLBaseStore):
             ),
         )
 
-        required_state_map: Dict[int, Dict[str, Set[str]]] = {}
+        required_state_map: dict[int, dict[str, set[str]]] = {}
         for row in rows:
             state = required_state_map[row[0]] = {}
             for event_type, state_key in db_to_json(row[1]):
@@ -437,7 +437,7 @@ class SlidingSyncStore(SQLBaseStore):
             ),
         )
 
-        room_configs: Dict[str, RoomSyncConfig] = {}
+        room_configs: dict[str, RoomSyncConfig] = {}
         for (
             room_id,
             timeline_limit,
@@ -449,9 +449,9 @@ class SlidingSyncStore(SQLBaseStore):
             )
 
         # Now look up the per-room stream data.
-        rooms: Dict[str, HaveSentRoom[str]] = {}
-        receipts: Dict[str, HaveSentRoom[str]] = {}
-        account_data: Dict[str, HaveSentRoom[str]] = {}
+        rooms: dict[str, HaveSentRoom[str]] = {}
+        receipts: dict[str, HaveSentRoom[str]] = {}
+        account_data: dict[str, HaveSentRoom[str]] = {}
 
         receipt_rows = self.db_pool.simple_select_list_txn(
             txn,
diff --git a/synapse/storage/databases/main/state.py b/synapse/storage/databases/main/state.py
index cfcc731f86..a0aea4975c 100644
--- a/synapse/storage/databases/main/state.py
+++ b/synapse/storage/databases/main/state.py
@@ -25,17 +25,10 @@ from typing import (
     TYPE_CHECKING,
     Any,
     Collection,
-    Dict,
-    FrozenSet,
     Iterable,
-    List,
     Mapping,
     MutableMapping,
-    Optional,
-    Set,
-    Tuple,
     TypeVar,
-    Union,
     cast,
     overload,
 )
@@ -91,8 +84,8 @@ class EventMetadata:
 
     room_id: str
     event_type: str
-    state_key: Optional[str]
-    rejection_reason: Optional[str]
+    state_key: str | None
+    rejection_reason: str | None
 
 
 def _retrieve_and_check_room_version(room_id: str, room_version_id: str) -> RoomVersion:
@@ -199,7 +192,7 @@ class StateGroupWorkerStore(EventsWorkerStore, SQLBaseStore):
     @trace
     async def get_metadata_for_events(
         self, event_ids: Collection[str]
-    ) -> Dict[str, EventMetadata]:
+    ) -> dict[str, EventMetadata]:
         """Get some metadata (room_id, type, state_key) for the given events.
 
         This method is a faster alternative than fetching the full events from
@@ -212,7 +205,7 @@ class StateGroupWorkerStore(EventsWorkerStore, SQLBaseStore):
         def get_metadata_for_events_txn(
             txn: LoggingTransaction,
             batch_ids: Collection[str],
-        ) -> Dict[str, EventMetadata]:
+        ) -> dict[str, EventMetadata]:
             clause, args = make_in_list_sql_clause(
                 self.database_engine, "e.event_id", batch_ids
             )
@@ -236,7 +229,7 @@ class StateGroupWorkerStore(EventsWorkerStore, SQLBaseStore):
                 for event_id, room_id, event_type, state_key, rejection_reason in txn
             }
 
-        result_map: Dict[str, EventMetadata] = {}
+        result_map: dict[str, EventMetadata] = {}
         for batch_ids in batch_iter(event_ids, 1000):
             result_map.update(
                 await self.db_pool.runInteraction(
@@ -248,7 +241,7 @@ class StateGroupWorkerStore(EventsWorkerStore, SQLBaseStore):
 
         return result_map
 
-    async def get_room_predecessor(self, room_id: str) -> Optional[JsonMapping]:
+    async def get_room_predecessor(self, room_id: str) -> JsonMapping | None:
         """Get the predecessor of an upgraded room if it exists.
         Otherwise return None.
 
@@ -308,7 +301,7 @@ class StateGroupWorkerStore(EventsWorkerStore, SQLBaseStore):
         return create_event
 
     @cached(max_entries=10000)
-    async def get_room_type(self, room_id: str) -> Union[Optional[str], Sentinel]:
+    async def get_room_type(self, room_id: str) -> str | None | Sentinel:
         """Fetch room type for given room.
 
         Since this function is cached, any missing values would be cached as
@@ -329,8 +322,8 @@ class StateGroupWorkerStore(EventsWorkerStore, SQLBaseStore):
 
     @cachedList(cached_method_name="get_room_type", list_name="room_ids")
     async def bulk_get_room_type(
-        self, room_ids: Set[str]
-    ) -> Mapping[str, Union[Optional[str], Sentinel]]:
+        self, room_ids: set[str]
+    ) -> Mapping[str, str | None | Sentinel]:
         """
         Bulk fetch room types for the given rooms (via current state).
 
@@ -347,7 +340,7 @@ class StateGroupWorkerStore(EventsWorkerStore, SQLBaseStore):
 
         def txn(
             txn: LoggingTransaction,
-        ) -> MutableMapping[str, Union[Optional[str], Sentinel]]:
+        ) -> MutableMapping[str, str | None | Sentinel]:
             clause, args = make_in_list_sql_clause(
                 txn.database_engine, "room_id", room_ids
             )
@@ -403,13 +396,13 @@ class StateGroupWorkerStore(EventsWorkerStore, SQLBaseStore):
         return results
 
     @cached(max_entries=10000)
-    async def get_room_encryption(self, room_id: str) -> Optional[str]:
+    async def get_room_encryption(self, room_id: str) -> str | None:
         raise NotImplementedError()
 
     @cachedList(cached_method_name="get_room_encryption", list_name="room_ids")
     async def bulk_get_room_encryption(
-        self, room_ids: Set[str]
-    ) -> Mapping[str, Union[Optional[str], Sentinel]]:
+        self, room_ids: set[str]
+    ) -> Mapping[str, str | None | Sentinel]:
         """
         Bulk fetch room encryption for the given rooms (via current state).
 
@@ -427,7 +420,7 @@ class StateGroupWorkerStore(EventsWorkerStore, SQLBaseStore):
 
         def txn(
             txn: LoggingTransaction,
-        ) -> MutableMapping[str, Union[Optional[str], Sentinel]]:
+        ) -> MutableMapping[str, str | None | Sentinel]:
             clause, args = make_in_list_sql_clause(
                 txn.database_engine, "room_id", room_ids
             )
@@ -469,7 +462,7 @@ class StateGroupWorkerStore(EventsWorkerStore, SQLBaseStore):
         # If we haven't updated `room_stats_state` with the room yet, query the state
         # directly. This should happen only rarely so we don't mind if we do this in a
         # loop.
-        encryption_event_ids: List[str] = []
+        encryption_event_ids: list[str] = []
         for room_id in room_ids - results.keys():
             state_map = await self.get_partial_filtered_current_state_ids(
                 room_id,
@@ -541,7 +534,7 @@ class StateGroupWorkerStore(EventsWorkerStore, SQLBaseStore):
 
     async def check_if_events_in_current_state(
         self, event_ids: StrCollection
-    ) -> FrozenSet[str]:
+    ) -> frozenset[str]:
         """Checks and returns which of the given events is part of the current state."""
         rows = await self.db_pool.simple_select_many_batch(
             table="current_state_events",
@@ -556,7 +549,7 @@ class StateGroupWorkerStore(EventsWorkerStore, SQLBaseStore):
     # FIXME: how should this be cached?
     @cancellable
     async def get_partial_filtered_current_state_ids(
-        self, room_id: str, state_filter: Optional[StateFilter] = None
+        self, room_id: str, state_filter: StateFilter | None = None
     ) -> StateMap[str]:
         """Get the current state event of a given type for a room based on the
         current_state_events table.  This may not be as up-to-date as the result
@@ -609,7 +602,7 @@ class StateGroupWorkerStore(EventsWorkerStore, SQLBaseStore):
         )
 
     @cached(max_entries=50000)
-    async def _get_state_group_for_event(self, event_id: str) -> Optional[int]:
+    async def _get_state_group_for_event(self, event_id: str) -> int | None:
         return await self.db_pool.simple_select_one_onecol(
             table="event_to_state_groups",
             keyvalues={"event_id": event_id},
@@ -632,7 +625,7 @@ class StateGroupWorkerStore(EventsWorkerStore, SQLBaseStore):
              RuntimeError if the state is unknown at any of the given events
         """
         rows = cast(
-            List[Tuple[str, int]],
+            list[tuple[str, int]],
             await self.db_pool.simple_select_many_batch(
                 table="event_to_state_groups",
                 column="event_id",
@@ -651,7 +644,7 @@ class StateGroupWorkerStore(EventsWorkerStore, SQLBaseStore):
 
     async def get_referenced_state_groups(
         self, state_groups: Iterable[int]
-    ) -> Set[int]:
+    ) -> set[int]:
         """Check if the state groups are referenced by events.
 
         Args:
@@ -662,7 +655,7 @@ class StateGroupWorkerStore(EventsWorkerStore, SQLBaseStore):
         """
 
         rows = cast(
-            List[Tuple[int]],
+            list[tuple[int]],
             await self.db_pool.simple_select_many_batch(
                 table="event_to_state_groups",
                 column="state_group",
@@ -803,7 +796,7 @@ class MainStateBackgroundUpdateStore(RoomMemberWorkerStore):
 
         def _background_remove_left_rooms_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[bool, Set[str]]:
+        ) -> tuple[bool, set[str]]:
             # get a batch of room ids to consider
             sql = """
                 SELECT DISTINCT room_id FROM current_state_events
@@ -884,7 +877,7 @@ class MainStateBackgroundUpdateStore(RoomMemberWorkerStore):
             # server didn't share a room with the remote user and therefore may
             # have missed any device updates.
             rows = cast(
-                List[Tuple[str]],
+                list[tuple[str]],
                 self.db_pool.simple_select_many_txn(
                     txn,
                     table="current_state_events",
@@ -975,7 +968,7 @@ class StateStore(StateGroupWorkerStore, MainStateBackgroundUpdateStore):
 
 
 @attr.s(auto_attribs=True, slots=True)
-class StateMapWrapper(Dict[StateKey, str]):
+class StateMapWrapper(dict[StateKey, str]):
     """A wrapper around a StateMap[str] to ensure that we only query for items
     that were not filtered out.
 
@@ -991,15 +984,13 @@ class StateMapWrapper(Dict[StateKey, str]):
         return super().__getitem__(key)
 
     @overload  # type: ignore[override]
-    def get(self, key: StateKey, default: None = None, /) -> Optional[str]: ...
+    def get(self, key: StateKey, default: None = None, /) -> str | None: ...
     @overload
     def get(self, key: StateKey, default: str, /) -> str: ...
     @overload
-    def get(self, key: StateKey, default: _T, /) -> Union[str, _T]: ...
+    def get(self, key: StateKey, default: _T, /) -> str | _T: ...
 
-    def get(
-        self, key: StateKey, default: Union[str, _T, None] = None
-    ) -> Union[str, _T, None]:
+    def get(self, key: StateKey, default: str | _T | None = None) -> str | _T | None:
         if key not in self.state_filter:
             raise Exception("State map was filtered and doesn't include: %s", key)
         return super().get(key, default)
diff --git a/synapse/storage/databases/main/state_deltas.py b/synapse/storage/databases/main/state_deltas.py
index 303b232d7b..cd8f286d08 100644
--- a/synapse/storage/databases/main/state_deltas.py
+++ b/synapse/storage/databases/main/state_deltas.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, List, Optional, Tuple
+from typing import TYPE_CHECKING
 
 import attr
 
@@ -50,10 +50,10 @@ class StateDelta:
     event_type: str
     state_key: str
 
-    event_id: Optional[str]
+    event_id: str | None
     """new event_id for this state key. None if the state has been deleted."""
 
-    prev_event_id: Optional[str]
+    prev_event_id: str | None
     """previous event_id for this state key. None if it's new state."""
 
 
@@ -79,7 +79,7 @@ class StateDeltasStore(SQLBaseStore):
 
     async def get_partial_current_state_deltas(
         self, prev_stream_id: int, max_stream_id: int
-    ) -> Tuple[int, List[StateDelta]]:
+    ) -> tuple[int, list[StateDelta]]:
         """Fetch a list of room state changes since the given stream id
 
         This may be the partial state if we're lazy joining the room.
@@ -114,7 +114,7 @@ class StateDeltasStore(SQLBaseStore):
 
         def get_current_state_deltas_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[int, List[StateDelta]]:
+        ) -> tuple[int, list[StateDelta]]:
             # First we calculate the max stream id that will give us less than
             # N results.
             # We arbitrarily limit to 100 stream_id entries to ensure we don't
@@ -191,9 +191,9 @@ class StateDeltasStore(SQLBaseStore):
         txn: LoggingTransaction,
         room_id: str,
         *,
-        from_token: Optional[RoomStreamToken],
-        to_token: Optional[RoomStreamToken],
-    ) -> List[StateDelta]:
+        from_token: RoomStreamToken | None,
+        to_token: RoomStreamToken | None,
+    ) -> list[StateDelta]:
         """
         Get the state deltas between two tokens.
 
@@ -237,9 +237,9 @@ class StateDeltasStore(SQLBaseStore):
         self,
         room_id: str,
         *,
-        from_token: Optional[RoomStreamToken],
-        to_token: Optional[RoomStreamToken],
-    ) -> List[StateDelta]:
+        from_token: RoomStreamToken | None,
+        to_token: RoomStreamToken | None,
+    ) -> list[StateDelta]:
         """
         Get the state deltas between two tokens.
 
@@ -275,7 +275,7 @@ class StateDeltasStore(SQLBaseStore):
         room_ids: StrCollection,
         from_token: RoomStreamToken,
         to_token: RoomStreamToken,
-    ) -> List[StateDelta]:
+    ) -> list[StateDelta]:
         """Get the state deltas between two tokens for the set of rooms."""
 
         room_ids = self._curr_state_delta_stream_cache.get_entities_changed(
@@ -287,7 +287,7 @@ class StateDeltasStore(SQLBaseStore):
         def get_current_state_deltas_for_rooms_txn(
             txn: LoggingTransaction,
             room_ids: StrCollection,
-        ) -> List[StateDelta]:
+        ) -> list[StateDelta]:
             clause, args = make_in_list_sql_clause(
                 self.database_engine, "room_id", room_ids
             )
diff --git a/synapse/storage/databases/main/stats.py b/synapse/storage/databases/main/stats.py
index 74830b7129..6568e2aa08 100644
--- a/synapse/storage/databases/main/stats.py
+++ b/synapse/storage/databases/main/stats.py
@@ -26,12 +26,7 @@ from typing import (
     TYPE_CHECKING,
     Any,
     Counter,
-    Dict,
     Iterable,
-    List,
-    Optional,
-    Tuple,
-    Union,
     cast,
 )
 
@@ -154,7 +149,7 @@ class StatsStore(StateDeltasStore):
 
         last_user_id = progress.get("last_user_id", "")
 
-        def _get_next_batch(txn: LoggingTransaction) -> List[str]:
+        def _get_next_batch(txn: LoggingTransaction) -> list[str]:
             sql = """
                     SELECT DISTINCT name FROM users
                     WHERE name > ?
@@ -200,7 +195,7 @@ class StatsStore(StateDeltasStore):
 
         last_room_id = progress.get("last_room_id", "")
 
-        def _get_next_batch(txn: LoggingTransaction) -> List[str]:
+        def _get_next_batch(txn: LoggingTransaction) -> list[str]:
             sql = """
                     SELECT DISTINCT room_id FROM current_state_events
                     WHERE room_id > ?
@@ -245,7 +240,7 @@ class StatsStore(StateDeltasStore):
             desc="stats_incremental_position",
         )
 
-    async def update_room_state(self, room_id: str, fields: Dict[str, Any]) -> None:
+    async def update_room_state(self, room_id: str, fields: dict[str, Any]) -> None:
         """Update the state of a room.
 
         fields can contain the following keys with string values:
@@ -299,7 +294,7 @@ class StatsStore(StateDeltasStore):
     @cached()
     async def get_earliest_token_for_stats(
         self, stats_type: str, id: str
-    ) -> Optional[int]:
+    ) -> int | None:
         """
         Fetch the "earliest token". This is used by the room stats delta
         processor to ignore deltas that have been processed between the
@@ -320,7 +315,7 @@ class StatsStore(StateDeltasStore):
         )
 
     async def bulk_update_stats_delta(
-        self, ts: int, updates: Dict[str, Dict[str, Counter[str]]], stream_id: int
+        self, ts: int, updates: dict[str, dict[str, Counter[str]]], stream_id: int
     ) -> None:
         """Bulk update stats tables for a given stream_id and updates the stats
         incremental position.
@@ -363,9 +358,9 @@ class StatsStore(StateDeltasStore):
         ts: int,
         stats_type: str,
         stats_id: str,
-        fields: Dict[str, int],
+        fields: dict[str, int],
         complete_with_stream_id: int,
-        absolute_field_overrides: Optional[Dict[str, int]] = None,
+        absolute_field_overrides: dict[str, int] | None = None,
     ) -> None:
         """
         Updates the statistics for a subject, with a delta (difference/relative
@@ -401,9 +396,9 @@ class StatsStore(StateDeltasStore):
         ts: int,
         stats_type: str,
         stats_id: str,
-        fields: Dict[str, int],
+        fields: dict[str, int],
         complete_with_stream_id: int,
-        absolute_field_overrides: Optional[Dict[str, int]] = None,
+        absolute_field_overrides: dict[str, int] | None = None,
     ) -> None:
         if absolute_field_overrides is None:
             absolute_field_overrides = {}
@@ -450,9 +445,9 @@ class StatsStore(StateDeltasStore):
         self,
         txn: LoggingTransaction,
         table: str,
-        keyvalues: Dict[str, Any],
-        absolutes: Dict[str, Any],
-        additive_relatives: Dict[str, int],
+        keyvalues: dict[str, Any],
+        absolutes: dict[str, Any],
+        additive_relatives: dict[str, int],
     ) -> None:
         """Used to update values in the stats tables.
 
@@ -510,11 +505,11 @@ class StatsStore(StateDeltasStore):
 
         def _fetch_current_state_stats(
             txn: LoggingTransaction,
-        ) -> Tuple[List[str], Dict[str, int], int, List[str], int]:
+        ) -> tuple[list[str], dict[str, int], int, list[str], int]:
             pos = self.get_room_max_stream_ordering()  # type: ignore[attr-defined]
 
             rows = cast(
-                List[Tuple[str]],
+                list[tuple[str]],
                 self.db_pool.simple_select_many_txn(
                     txn,
                     table="current_state_events",
@@ -544,7 +539,7 @@ class StatsStore(StateDeltasStore):
                 """,
                 (room_id,),
             )
-            membership_counts = dict(cast(Iterable[Tuple[str, int]], txn))
+            membership_counts = dict(cast(Iterable[tuple[str, int]], txn))
 
             txn.execute(
                 """
@@ -554,7 +549,7 @@ class StatsStore(StateDeltasStore):
                 (room_id,),
             )
 
-            current_state_events_count = cast(Tuple[int], txn.fetchone())[0]
+            current_state_events_count = cast(tuple[int], txn.fetchone())[0]
 
             users_in_room = self.get_users_in_room_txn(txn, room_id)  # type: ignore[attr-defined]
 
@@ -588,7 +583,7 @@ class StatsStore(StateDeltasStore):
             )
             return
 
-        room_state: Dict[str, Union[None, bool, str]] = {
+        room_state: dict[str, None | bool | str] = {
             "join_rules": None,
             "history_visibility": None,
             "encryption": None,
@@ -651,7 +646,7 @@ class StatsStore(StateDeltasStore):
     async def _calculate_and_set_initial_state_for_user(self, user_id: str) -> None:
         def _calculate_and_set_initial_state_for_user_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[int, int]:
+        ) -> tuple[int, int]:
             pos = self._get_max_stream_id_in_current_state_deltas_txn(txn)
 
             txn.execute(
@@ -662,7 +657,7 @@ class StatsStore(StateDeltasStore):
                 """,
                 (user_id,),
             )
-            count = cast(Tuple[int], txn.fetchone())[0]
+            count = cast(tuple[int], txn.fetchone())[0]
             return count, pos
 
         joined_rooms, pos = await self.db_pool.runInteraction(
@@ -683,12 +678,12 @@ class StatsStore(StateDeltasStore):
         self,
         start: int,
         limit: int,
-        from_ts: Optional[int] = None,
-        until_ts: Optional[int] = None,
-        order_by: Optional[str] = UserSortOrder.USER_ID.value,
+        from_ts: int | None = None,
+        until_ts: int | None = None,
+        order_by: str | None = UserSortOrder.USER_ID.value,
         direction: Direction = Direction.FORWARDS,
-        search_term: Optional[str] = None,
-    ) -> Tuple[List[Tuple[str, Optional[str], int, int]], int]:
+        search_term: str | None = None,
+    ) -> tuple[list[tuple[str, str | None, int, int]], int]:
         """Function to retrieve a paginated list of users and their uploaded local media
         (size and number). This will return a json list of users and the
         total number of users matching the filter criteria.
@@ -713,7 +708,7 @@ class StatsStore(StateDeltasStore):
 
         def get_users_media_usage_paginate_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[List[Tuple[str, Optional[str], int, int]], int]:
+        ) -> tuple[list[tuple[str, str | None, int, int]], int]:
             filters = []
             args: list = []
 
@@ -766,7 +761,7 @@ class StatsStore(StateDeltasStore):
                 sql_base=sql_base,
             )
             txn.execute(sql, args)
-            count = cast(Tuple[int], txn.fetchone())[0]
+            count = cast(tuple[int], txn.fetchone())[0]
 
             sql = """
                 SELECT
@@ -785,7 +780,7 @@ class StatsStore(StateDeltasStore):
 
             args += [limit, start]
             txn.execute(sql, args)
-            users = cast(List[Tuple[str, Optional[str], int, int]], txn.fetchall())
+            users = cast(list[tuple[str, str | None, int, int]], txn.fetchall())
 
             return users, count
 
diff --git a/synapse/storage/databases/main/stream.py b/synapse/storage/databases/main/stream.py
index 66280f2f9a..8644ff412e 100644
--- a/synapse/storage/databases/main/stream.py
+++ b/synapse/storage/databases/main/stream.py
@@ -47,15 +47,10 @@ from typing import (
     AbstractSet,
     Any,
     Collection,
-    Dict,
     Iterable,
-    List,
     Literal,
     Mapping,
-    Optional,
     Protocol,
-    Set,
-    Tuple,
     cast,
     overload,
 )
@@ -106,24 +101,24 @@ class PaginateFunction(Protocol):
         *,
         room_id: str,
         from_key: RoomStreamToken,
-        to_key: Optional[RoomStreamToken] = None,
+        to_key: RoomStreamToken | None = None,
         direction: Direction = Direction.BACKWARDS,
         limit: int = 0,
-    ) -> Tuple[List[EventBase], RoomStreamToken, bool]: ...
+    ) -> tuple[list[EventBase], RoomStreamToken, bool]: ...
 
 
 # Used as return values for pagination APIs
 @attr.s(slots=True, frozen=True, auto_attribs=True)
 class _EventDictReturn:
     event_id: str
-    topological_ordering: Optional[int]
+    topological_ordering: int | None
     stream_ordering: int
 
 
 @attr.s(slots=True, frozen=True, auto_attribs=True)
 class _EventsAround:
-    events_before: List[EventBase]
-    events_after: List[EventBase]
+    events_before: list[EventBase]
+    events_after: list[EventBase]
     start: RoomStreamToken
     end: RoomStreamToken
 
@@ -143,22 +138,22 @@ class CurrentStateDeltaMembership:
 
     room_id: str
     # Event
-    event_id: Optional[str]
+    event_id: str | None
     event_pos: PersistedEventPosition
     membership: str
-    sender: Optional[str]
+    sender: str | None
     # Prev event
-    prev_event_id: Optional[str]
-    prev_event_pos: Optional[PersistedEventPosition]
-    prev_membership: Optional[str]
-    prev_sender: Optional[str]
+    prev_event_id: str | None
+    prev_event_pos: PersistedEventPosition | None
+    prev_membership: str | None
+    prev_sender: str | None
 
 
 def generate_pagination_where_clause(
     direction: Direction,
-    column_names: Tuple[str, str],
-    from_token: Optional[Tuple[Optional[int], int]],
-    to_token: Optional[Tuple[Optional[int], int]],
+    column_names: tuple[str, str],
+    from_token: tuple[int | None, int] | None,
+    to_token: tuple[int | None, int] | None,
     engine: BaseDatabaseEngine,
 ) -> str:
     """Creates an SQL expression to bound the columns by the pagination
@@ -222,11 +217,9 @@ def generate_pagination_where_clause(
 
 def generate_pagination_bounds(
     direction: Direction,
-    from_token: Optional[RoomStreamToken],
-    to_token: Optional[RoomStreamToken],
-) -> Tuple[
-    str, Optional[Tuple[Optional[int], int]], Optional[Tuple[Optional[int], int]]
-]:
+    from_token: RoomStreamToken | None,
+    to_token: RoomStreamToken | None,
+) -> tuple[str, tuple[int | None, int] | None, tuple[int | None, int] | None]:
     """
     Generate a start and end point for this page of events.
 
@@ -261,7 +254,7 @@ def generate_pagination_bounds(
     # by fetching all events between the min stream token and the maximum
     # stream token (as returned by `RoomStreamToken.get_max_stream_pos`) and
     # then filtering the results.
-    from_bound: Optional[Tuple[Optional[int], int]] = None
+    from_bound: tuple[int | None, int] | None = None
     if from_token:
         if from_token.topological is not None:
             from_bound = from_token.as_historical_tuple()
@@ -276,7 +269,7 @@ def generate_pagination_bounds(
                 from_token.stream,
             )
 
-    to_bound: Optional[Tuple[Optional[int], int]] = None
+    to_bound: tuple[int | None, int] | None = None
     if to_token:
         if to_token.topological is not None:
             to_bound = to_token.as_historical_tuple()
@@ -295,7 +288,7 @@ def generate_pagination_bounds(
 
 
 def generate_next_token(
-    direction: Direction, last_topo_ordering: Optional[int], last_stream_ordering: int
+    direction: Direction, last_topo_ordering: int | None, last_stream_ordering: int
 ) -> RoomStreamToken:
     """
     Generate the next room stream token based on the currently returned data.
@@ -320,8 +313,8 @@ def generate_next_token(
 
 def _make_generic_sql_bound(
     bound: str,
-    column_names: Tuple[str, str],
-    values: Tuple[Optional[int], int],
+    column_names: tuple[str, str],
+    values: tuple[int | None, int],
     engine: BaseDatabaseEngine,
 ) -> str:
     """Create an SQL expression that bounds the given column names by the
@@ -385,9 +378,9 @@ def _make_generic_sql_bound(
 
 
 def _filter_results(
-    lower_token: Optional[RoomStreamToken],
-    upper_token: Optional[RoomStreamToken],
-    instance_name: Optional[str],
+    lower_token: RoomStreamToken | None,
+    upper_token: RoomStreamToken | None,
+    instance_name: str | None,
     topological_ordering: int,
     stream_ordering: int,
 ) -> bool:
@@ -440,9 +433,9 @@ def _filter_results(
 
 
 def _filter_results_by_stream(
-    lower_token: Optional[RoomStreamToken],
-    upper_token: Optional[RoomStreamToken],
-    instance_name: Optional[str],
+    lower_token: RoomStreamToken | None,
+    upper_token: RoomStreamToken | None,
+    instance_name: str | None,
     stream_ordering: int,
 ) -> bool:
     """
@@ -484,7 +477,7 @@ def _filter_results_by_stream(
     return True
 
 
-def filter_to_clause(event_filter: Optional[Filter]) -> Tuple[str, List[str]]:
+def filter_to_clause(event_filter: Filter | None) -> tuple[str, list[str]]:
     # NB: This may create SQL clauses that don't optimise well (and we don't
     # have indices on all possible clauses). E.g. it may create
     # "room_id == X AND room_id != X", which postgres doesn't optimise.
@@ -666,10 +659,10 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
         *,
         room_ids: Collection[str],
         from_key: RoomStreamToken,
-        to_key: Optional[RoomStreamToken] = None,
+        to_key: RoomStreamToken | None = None,
         direction: Direction = Direction.BACKWARDS,
         limit: int = 0,
-    ) -> Dict[str, Tuple[List[EventBase], RoomStreamToken, bool]]:
+    ) -> dict[str, tuple[list[EventBase], RoomStreamToken, bool]]:
         """Get new room events in stream ordering since `from_key`.
 
         Args:
@@ -730,7 +723,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
 
     def get_rooms_that_changed(
         self, room_ids: Collection[str], from_key: RoomStreamToken
-    ) -> Set[str]:
+    ) -> set[str]:
         """Given a list of rooms and a token, return rooms where there may have
         been changes.
         """
@@ -765,7 +758,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
                     AND event_stream_ordering > ?
             """
 
-            results: Set[str] = set()
+            results: set[str] = set()
             for batch in batch_iter(room_ids, 1000):
                 clause, args = make_in_list_sql_clause(
                     self.database_engine, "room_id", batch
@@ -788,10 +781,10 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
         *,
         room_id: str,
         from_key: RoomStreamToken,
-        to_key: Optional[RoomStreamToken] = None,
+        to_key: RoomStreamToken | None = None,
         direction: Direction = Direction.BACKWARDS,
         limit: int = 0,
-    ) -> Tuple[List[EventBase], RoomStreamToken, bool]:
+    ) -> tuple[list[EventBase], RoomStreamToken, bool]:
         """
         Paginate events by `stream_ordering` in the room from the `from_key` in the
         given `direction` to the `to_key` or `limit`.
@@ -876,7 +869,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
             engine=self.database_engine,
         )
 
-        def f(txn: LoggingTransaction) -> Tuple[List[_EventDictReturn], bool]:
+        def f(txn: LoggingTransaction) -> tuple[list[_EventDictReturn], bool]:
             sql = f"""
                 SELECT event_id, instance_name, stream_ordering
                 FROM events
@@ -940,8 +933,8 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
         user_id: str,
         from_key: RoomStreamToken,
         to_key: RoomStreamToken,
-        excluded_room_ids: Optional[List[str]] = None,
-    ) -> List[CurrentStateDeltaMembership]:
+        excluded_room_ids: list[str] | None = None,
+    ) -> list[CurrentStateDeltaMembership]:
         """
         Fetch membership events (and the previous event that was replaced by that one)
         for a given user.
@@ -995,13 +988,13 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
             if not has_changed:
                 return []
 
-        def f(txn: LoggingTransaction) -> List[CurrentStateDeltaMembership]:
+        def f(txn: LoggingTransaction) -> list[CurrentStateDeltaMembership]:
             # To handle tokens with a non-empty instance_map we fetch more
             # results than necessary and then filter down
             min_from_id = from_key.stream
             max_to_id = to_key.get_max_stream_pos()
 
-            args: List[Any] = [min_from_id, max_to_id, EventTypes.Member, user_id]
+            args: list[Any] = [min_from_id, max_to_id, EventTypes.Member, user_id]
 
             # TODO: It would be good to assert that the `from_token`/`to_token` is >=
             # the first row in `current_state_delta_stream` for the rooms we're
@@ -1044,7 +1037,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
 
             txn.execute(sql, args)
 
-            membership_changes: List[CurrentStateDeltaMembership] = []
+            membership_changes: list[CurrentStateDeltaMembership] = []
             for (
                 room_id,
                 event_id,
@@ -1135,8 +1128,8 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
         user_id: str,
         from_key: RoomStreamToken,
         to_key: RoomStreamToken,
-        excluded_room_ids: Optional[AbstractSet[str]] = None,
-    ) -> Dict[str, RoomsForUserStateReset]:
+        excluded_room_ids: AbstractSet[str] | None = None,
+    ) -> dict[str, RoomsForUserStateReset]:
         """
         Fetch membership events that result in a meaningful membership change for a
         given user.
@@ -1185,7 +1178,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
         if excluded_room_ids is not None:
             room_ids_to_exclude = excluded_room_ids
 
-        def f(txn: LoggingTransaction) -> Dict[str, RoomsForUserStateReset]:
+        def f(txn: LoggingTransaction) -> dict[str, RoomsForUserStateReset]:
             # To handle tokens with a non-empty instance_map we fetch more
             # results than necessary and then filter down
             min_from_id = from_key.stream
@@ -1248,7 +1241,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
                 (user_id, EventTypes.Member, user_id, min_from_id, max_to_id),
             )
 
-            membership_changes: Dict[str, RoomsForUserStateReset] = {}
+            membership_changes: dict[str, RoomsForUserStateReset] = {}
             for (
                 room_id,
                 membership_event_id,
@@ -1332,8 +1325,8 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
         user_id: str,
         from_key: RoomStreamToken,
         to_key: RoomStreamToken,
-        excluded_rooms: Optional[List[str]] = None,
-    ) -> List[EventBase]:
+        excluded_rooms: list[str] | None = None,
+    ) -> list[EventBase]:
         """Fetch membership events for a given user.
 
         All such events whose stream ordering `s` lies in the range
@@ -1351,13 +1344,13 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
             if not has_changed:
                 return []
 
-        def f(txn: LoggingTransaction) -> List[_EventDictReturn]:
+        def f(txn: LoggingTransaction) -> list[_EventDictReturn]:
             # To handle tokens with a non-empty instance_map we fetch more
             # results than necessary and then filter down
             min_from_id = from_key.stream
             max_to_id = to_key.get_max_stream_pos()
 
-            args: List[Any] = [user_id, min_from_id, max_to_id]
+            args: list[Any] = [user_id, min_from_id, max_to_id]
 
             ignore_room_clause = ""
             if excluded_rooms is not None and len(excluded_rooms) > 0:
@@ -1403,7 +1396,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
 
     async def get_recent_events_for_room(
         self, room_id: str, limit: int, end_token: RoomStreamToken
-    ) -> Tuple[List[EventBase], RoomStreamToken]:
+    ) -> tuple[list[EventBase], RoomStreamToken]:
         """Get the most recent events in the room in topological ordering.
 
         Args:
@@ -1428,7 +1421,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
 
     async def get_recent_event_ids_for_room(
         self, room_id: str, limit: int, end_token: RoomStreamToken
-    ) -> Tuple[List[_EventDictReturn], RoomStreamToken]:
+    ) -> tuple[list[_EventDictReturn], RoomStreamToken]:
         """Get the most recent events in the room in topological ordering.
 
         Args:
@@ -1459,7 +1452,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
 
     async def get_room_event_before_stream_ordering(
         self, room_id: str, stream_ordering: int
-    ) -> Optional[Tuple[int, int, str]]:
+    ) -> tuple[int, int, str] | None:
         """Gets details of the first event in a room at or before a stream ordering
 
         Args:
@@ -1470,7 +1463,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
             A tuple of (stream ordering, topological ordering, event_id)
         """
 
-        def _f(txn: LoggingTransaction) -> Optional[Tuple[int, int, str]]:
+        def _f(txn: LoggingTransaction) -> tuple[int, int, str] | None:
             sql = """
                 SELECT stream_ordering, topological_ordering, event_id
                 FROM events
@@ -1483,7 +1476,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
                 LIMIT 1
             """
             txn.execute(sql, (room_id, stream_ordering))
-            return cast(Optional[Tuple[int, int, str]], txn.fetchone())
+            return cast(tuple[int, int, str] | None, txn.fetchone())
 
         return await self.db_pool.runInteraction(
             "get_room_event_before_stream_ordering", _f
@@ -1493,7 +1486,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
         self,
         room_id: str,
         end_token: RoomStreamToken,
-    ) -> Optional[str]:
+    ) -> str | None:
         """Returns the ID of the last event in a room at or before a stream ordering
 
         Args:
@@ -1518,8 +1511,8 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
     async def get_last_event_pos_in_room(
         self,
         room_id: str,
-        event_types: Optional[StrCollection] = None,
-    ) -> Optional[Tuple[str, PersistedEventPosition]]:
+        event_types: StrCollection | None = None,
+    ) -> tuple[str, PersistedEventPosition] | None:
         """
         Returns the ID and event position of the last event in a room.
 
@@ -1536,9 +1529,9 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
 
         def _get_last_event_pos_in_room_txn(
             txn: LoggingTransaction,
-        ) -> Optional[Tuple[str, PersistedEventPosition]]:
+        ) -> tuple[str, PersistedEventPosition] | None:
             event_type_clause = ""
-            event_type_args: List[str] = []
+            event_type_args: list[str] = []
             if event_types is not None and len(event_types) > 0:
                 event_type_clause, event_type_args = make_in_list_sql_clause(
                     txn.database_engine, "type", event_types
@@ -1562,7 +1555,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
                 [room_id] + event_type_args,
             )
 
-            row = cast(Optional[Tuple[str, int, str]], txn.fetchone())
+            row = cast(tuple[str, int, str] | None, txn.fetchone())
             if row is not None:
                 event_id, stream_ordering, instance_name = row
 
@@ -1584,8 +1577,8 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
         self,
         room_id: str,
         end_token: RoomStreamToken,
-        event_types: Optional[StrCollection] = None,
-    ) -> Optional[Tuple[str, PersistedEventPosition]]:
+        event_types: StrCollection | None = None,
+    ) -> tuple[str, PersistedEventPosition] | None:
         """
         Returns the ID and event position of the last event in a room at or before a
         stream ordering.
@@ -1602,7 +1595,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
 
         def get_last_event_pos_in_room_before_stream_ordering_txn(
             txn: LoggingTransaction,
-        ) -> Optional[Tuple[str, PersistedEventPosition]]:
+        ) -> tuple[str, PersistedEventPosition] | None:
             # We're looking for the closest event at or before the token. We need to
             # handle the fact that the stream token can be a vector clock (with an
             # `instance_map`) and events can be persisted on different instances
@@ -1616,7 +1609,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
             max_stream = end_token.get_max_stream_pos()
 
             event_type_clause = ""
-            event_type_args: List[str] = []
+            event_type_args: list[str] = []
             if event_types is not None and len(event_types) > 0:
                 event_type_clause, event_type_args = make_in_list_sql_clause(
                     txn.database_engine, "type", event_types
@@ -1692,7 +1685,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
         self,
         room_ids: StrCollection,
         end_token: RoomStreamToken,
-    ) -> Dict[str, int]:
+    ) -> dict[str, int]:
         """Bulk fetch the stream position of the latest events in the given
         rooms
         """
@@ -1705,8 +1698,8 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
         # Check that the stream position for the rooms are from before the
         # minimum position of the token. If not then we need to fetch more
         # rows.
-        results: Dict[str, int] = {}
-        recheck_rooms: Set[str] = set()
+        results: dict[str, int] = {}
+        recheck_rooms: set[str] = set()
         min_token = end_token.stream
         for room_id, stream in uncapped_results.items():
             if stream is None:
@@ -1739,7 +1732,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
     @cachedList(cached_method_name="_get_max_event_pos", list_name="room_ids")
     async def _bulk_get_max_event_pos(
         self, room_ids: StrCollection
-    ) -> Mapping[str, Optional[int]]:
+    ) -> Mapping[str, int | None]:
         """Fetch the max position of a persisted event in the room."""
 
         # We need to be careful not to return positions ahead of the current
@@ -1747,11 +1740,11 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
         now_token = self.get_room_max_token()
         max_pos = now_token.get_max_stream_pos()
 
-        results: Dict[str, int] = {}
+        results: dict[str, int] = {}
 
         # First, we check for the rooms in the stream change cache to see if we
         # can just use the latest position from it.
-        missing_room_ids: Set[str] = set()
+        missing_room_ids: set[str] = set()
         for room_id in room_ids:
             stream_pos = self._events_stream_cache.get_max_pos_of_last_change(room_id)
             if stream_pos is not None:
@@ -1770,7 +1763,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
 
         def bulk_get_max_event_pos_fallback_txn(
             txn: LoggingTransaction, batched_room_ids: StrCollection
-        ) -> Dict[str, int]:
+        ) -> dict[str, int]:
             clause, args = make_in_list_sql_clause(
                 self.database_engine, "room_id", batched_room_ids
             )
@@ -1795,7 +1788,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
         # the joins and sub-queries.
         def bulk_get_max_event_pos_from_sliding_sync_tables_txn(
             txn: LoggingTransaction, batched_room_ids: StrCollection
-        ) -> Dict[str, int]:
+        ) -> dict[str, int]:
             clause, args = make_in_list_sql_clause(
                 self.database_engine, "room_id", batched_room_ids
             )
@@ -1808,7 +1801,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
             txn.execute(sql, args)
             return {row[0]: row[1] for row in txn}
 
-        recheck_rooms: Set[str] = set()
+        recheck_rooms: set[str] = set()
         for batched in batch_iter(room_ids, 1000):
             if await self.have_finished_sliding_sync_background_jobs():
                 batch_results = await self.db_pool.runInteraction(
@@ -1864,14 +1857,14 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
         txn: LoggingTransaction,
         event_id: str,
         allow_none: bool = False,
-    ) -> Optional[int]: ...
+    ) -> int | None: ...
 
     def get_stream_id_for_event_txn(
         self,
         txn: LoggingTransaction,
         event_id: str,
         allow_none: bool = False,
-    ) -> Optional[int]:
+    ) -> int | None:
         # Type ignore: we pass keyvalues a Dict[str, str]; the function wants
         # Dict[str, Any]. I think mypy is unhappy because Dict is invariant?
         return self.db_pool.simple_select_one_onecol_txn(  # type: ignore[call-overload]
@@ -1974,7 +1967,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
         event_id: str,
         before_limit: int,
         after_limit: int,
-        event_filter: Optional[Filter] = None,
+        event_filter: Filter | None = None,
     ) -> _EventsAround:
         """Retrieve events and pagination tokens around a given event in a
         room.
@@ -2012,7 +2005,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
         event_id: str,
         before_limit: int,
         after_limit: int,
-        event_filter: Optional[Filter],
+        event_filter: Filter | None,
     ) -> dict:
         """Retrieves event_ids and pagination tokens around a given event in a
         room.
@@ -2077,7 +2070,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
         from_id: int,
         current_id: int,
         limit: int,
-    ) -> Tuple[int, Dict[str, Optional[int]]]:
+    ) -> tuple[int, dict[str, int | None]]:
         """Get all new events
 
         Returns all event ids with from_id < stream_ordering <= current_id.
@@ -2098,7 +2091,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
 
         def get_all_new_event_ids_stream_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[int, Dict[str, Optional[int]]]:
+        ) -> tuple[int, dict[str, int | None]]:
             sql = (
                 "SELECT e.stream_ordering, e.event_id, e.received_ts"
                 " FROM events AS e"
@@ -2115,7 +2108,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
             if len(rows) == limit:
                 upper_bound = rows[-1][0]
 
-            event_to_received_ts: Dict[str, Optional[int]] = {
+            event_to_received_ts: dict[str, int | None] = {
                 row[1]: row[2] for row in rows
             }
             return upper_bound, event_to_received_ts
@@ -2194,7 +2187,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
         """
         txn.execute(sql)
         min_positions = dict(
-            cast(Iterable[Tuple[str, int]], txn)
+            cast(Iterable[tuple[str, int]], txn)
         )  # Map from type -> min position
 
         # Ensure we do actually have some values here
@@ -2225,11 +2218,11 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
         txn: LoggingTransaction,
         room_id: str,
         from_token: RoomStreamToken,
-        to_token: Optional[RoomStreamToken] = None,
+        to_token: RoomStreamToken | None = None,
         direction: Direction = Direction.BACKWARDS,
         limit: int = 0,
-        event_filter: Optional[Filter] = None,
-    ) -> Tuple[List[_EventDictReturn], RoomStreamToken, bool]:
+        event_filter: Filter | None = None,
+    ) -> tuple[list[_EventDictReturn], RoomStreamToken, bool]:
         """Returns list of events before or after a given token.
 
         Args:
@@ -2269,7 +2262,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
             # Token selection matches what we do below if there are no rows
             return [], to_token if to_token else from_token, False
 
-        args: List[Any] = [room_id]
+        args: list[Any] = [room_id]
 
         order, from_bound, to_bound = generate_pagination_bounds(
             direction, from_token, to_token
@@ -2399,11 +2392,11 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
         *,
         room_id: str,
         from_key: RoomStreamToken,
-        to_key: Optional[RoomStreamToken] = None,
+        to_key: RoomStreamToken | None = None,
         direction: Direction = Direction.BACKWARDS,
         limit: int = 0,
-        event_filter: Optional[Filter] = None,
-    ) -> Tuple[List[EventBase], RoomStreamToken, bool]:
+        event_filter: Filter | None = None,
+    ) -> tuple[list[EventBase], RoomStreamToken, bool]:
         """
         Paginate events by `topological_ordering` (tie-break with `stream_ordering`) in
         the room from the `from_key` in the given `direction` to the `to_key` or
@@ -2529,9 +2522,9 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
     async def get_timeline_gaps(
         self,
         room_id: str,
-        from_token: Optional[RoomStreamToken],
+        from_token: RoomStreamToken | None,
         to_token: RoomStreamToken,
-    ) -> Optional[RoomStreamToken]:
+    ) -> RoomStreamToken | None:
         """Check if there is a gap, and return a token that marks the position
         of the gap in the stream.
         """
diff --git a/synapse/storage/databases/main/tags.py b/synapse/storage/databases/main/tags.py
index 94cf7f4052..0768dd78c0 100644
--- a/synapse/storage/databases/main/tags.py
+++ b/synapse/storage/databases/main/tags.py
@@ -21,7 +21,7 @@
 #
 
 import logging
-from typing import Any, Dict, Iterable, List, Mapping, Tuple, cast
+from typing import Any, Iterable, Mapping, cast
 
 from synapse.api.constants import AccountDataTypes
 from synapse.replication.tcp.streams import AccountDataStream
@@ -52,13 +52,13 @@ class TagsWorkerStore(AccountDataWorkerStore):
         """
 
         rows = cast(
-            List[Tuple[str, str, str]],
+            list[tuple[str, str, str]],
             await self.db_pool.simple_select_list(
                 "room_tags", {"user_id": user_id}, ["room_id", "tag", "content"]
             ),
         )
 
-        tags_by_room: Dict[str, Dict[str, JsonDict]] = {}
+        tags_by_room: dict[str, dict[str, JsonDict]] = {}
         for room_id, tag, content in rows:
             room_tags = tags_by_room.setdefault(room_id, {})
             room_tags[tag] = db_to_json(content)
@@ -66,7 +66,7 @@ class TagsWorkerStore(AccountDataWorkerStore):
 
     async def get_all_updated_tags(
         self, instance_name: str, last_id: int, current_id: int, limit: int
-    ) -> Tuple[List[Tuple[int, str, str]], int, bool]:
+    ) -> tuple[list[tuple[int, str, str]], int, bool]:
         """Get updates for tags replication stream.
 
         Args:
@@ -93,7 +93,7 @@ class TagsWorkerStore(AccountDataWorkerStore):
 
         def get_all_updated_tags_txn(
             txn: LoggingTransaction,
-        ) -> List[Tuple[int, str, str]]:
+        ) -> list[tuple[int, str, str]]:
             sql = (
                 "SELECT stream_id, user_id, room_id"
                 " FROM room_tags_revisions as r"
@@ -102,7 +102,7 @@ class TagsWorkerStore(AccountDataWorkerStore):
             )
             txn.execute(sql, (last_id, current_id, limit))
             # mypy doesn't understand what the query is selecting.
-            return cast(List[Tuple[int, str, str]], txn.fetchall())
+            return cast(list[tuple[int, str, str]], txn.fetchall())
 
         tag_ids = await self.db_pool.runInteraction(
             "get_all_updated_tags", get_all_updated_tags_txn
@@ -131,7 +131,7 @@ class TagsWorkerStore(AccountDataWorkerStore):
             rooms that changed since the stream_id token.
         """
 
-        def get_updated_tags_txn(txn: LoggingTransaction) -> List[str]:
+        def get_updated_tags_txn(txn: LoggingTransaction) -> list[str]:
             sql = (
                 "SELECT room_id from room_tags_revisions"
                 " WHERE user_id = ? AND stream_id > ?"
@@ -218,7 +218,7 @@ class TagsWorkerStore(AccountDataWorkerStore):
             A mapping of tags to tag content.
         """
         rows = cast(
-            List[Tuple[str, str]],
+            list[tuple[str, str]],
             await self.db_pool.simple_select_list(
                 table="room_tags",
                 keyvalues={"user_id": user_id, "room_id": room_id},
@@ -338,8 +338,8 @@ class TagsWorkerStore(AccountDataWorkerStore):
         if stream_name == AccountDataStream.NAME:
             # Cast is safe because the `AccountDataStream` should only be giving us
             # `AccountDataStreamRow`
-            account_data_stream_rows: List[AccountDataStream.AccountDataStreamRow] = (
-                cast(List[AccountDataStream.AccountDataStreamRow], rows)
+            account_data_stream_rows: list[AccountDataStream.AccountDataStreamRow] = (
+                cast(list[AccountDataStream.AccountDataStreamRow], rows)
             )
 
             for row in account_data_stream_rows:
diff --git a/synapse/storage/databases/main/task_scheduler.py b/synapse/storage/databases/main/task_scheduler.py
index 2d4804fef6..05ebb57cf3 100644
--- a/synapse/storage/databases/main/task_scheduler.py
+++ b/synapse/storage/databases/main/task_scheduler.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import TYPE_CHECKING, Any, List, Optional, Tuple, cast
+from typing import TYPE_CHECKING, Any, cast
 
 from synapse.storage._base import SQLBaseStore, db_to_json
 from synapse.storage.database import (
@@ -34,7 +34,7 @@ from synapse.util.json import json_encoder
 if TYPE_CHECKING:
     from synapse.server import HomeServer
 
-ScheduledTaskRow = Tuple[str, str, str, int, str, str, str, str]
+ScheduledTaskRow = tuple[str, str, str, int, str, str, str, str]
 
 
 class TaskSchedulerWorkerStore(SQLBaseStore):
@@ -63,12 +63,12 @@ class TaskSchedulerWorkerStore(SQLBaseStore):
     async def get_scheduled_tasks(
         self,
         *,
-        actions: Optional[List[str]] = None,
-        resource_id: Optional[str] = None,
-        statuses: Optional[List[TaskStatus]] = None,
-        max_timestamp: Optional[int] = None,
-        limit: Optional[int] = None,
-    ) -> List[ScheduledTask]:
+        actions: list[str] | None = None,
+        resource_id: str | None = None,
+        statuses: list[TaskStatus] | None = None,
+        max_timestamp: int | None = None,
+        limit: int | None = None,
+    ) -> list[ScheduledTask]:
         """Get a list of scheduled tasks from the DB.
 
         Args:
@@ -82,9 +82,9 @@ class TaskSchedulerWorkerStore(SQLBaseStore):
         Returns: a list of `ScheduledTask`, ordered by increasing timestamps
         """
 
-        def get_scheduled_tasks_txn(txn: LoggingTransaction) -> List[ScheduledTaskRow]:
-            clauses: List[str] = []
-            args: List[Any] = []
+        def get_scheduled_tasks_txn(txn: LoggingTransaction) -> list[ScheduledTaskRow]:
+            clauses: list[str] = []
+            args: list[Any] = []
             if resource_id:
                 clauses.append("resource_id = ?")
                 args.append(resource_id)
@@ -115,7 +115,7 @@ class TaskSchedulerWorkerStore(SQLBaseStore):
                 args.append(limit)
 
             txn.execute(sql, args)
-            return cast(List[ScheduledTaskRow], txn.fetchall())
+            return cast(list[ScheduledTaskRow], txn.fetchall())
 
         rows = await self.db_pool.runInteraction(
             "get_scheduled_tasks", get_scheduled_tasks_txn
@@ -152,9 +152,9 @@ class TaskSchedulerWorkerStore(SQLBaseStore):
         id: str,
         timestamp: int,
         *,
-        status: Optional[TaskStatus] = None,
-        result: Optional[JsonMapping] = None,
-        error: Optional[str] = None,
+        status: TaskStatus | None = None,
+        result: JsonMapping | None = None,
+        error: str | None = None,
     ) -> bool:
         """Update a scheduled task in the DB with some new value(s).
 
@@ -182,7 +182,7 @@ class TaskSchedulerWorkerStore(SQLBaseStore):
         )
         return nb_rows > 0
 
-    async def get_scheduled_task(self, id: str) -> Optional[ScheduledTask]:
+    async def get_scheduled_task(self, id: str) -> ScheduledTask | None:
         """Get a specific `ScheduledTask` from its id.
 
         Args:
@@ -191,7 +191,7 @@ class TaskSchedulerWorkerStore(SQLBaseStore):
         Returns: the task if available, `None` otherwise
         """
         row = cast(
-            Optional[ScheduledTaskRow],
+            ScheduledTaskRow | None,
             await self.db_pool.simple_select_one(
                 table="scheduled_tasks",
                 keyvalues={"id": id},
diff --git a/synapse/storage/databases/main/thread_subscriptions.py b/synapse/storage/databases/main/thread_subscriptions.py
index 50084887a4..e177e67ab1 100644
--- a/synapse/storage/databases/main/thread_subscriptions.py
+++ b/synapse/storage/databases/main/thread_subscriptions.py
@@ -14,12 +14,7 @@ import logging
 from typing import (
     TYPE_CHECKING,
     Any,
-    FrozenSet,
     Iterable,
-    List,
-    Optional,
-    Tuple,
-    Union,
     cast,
 )
 
@@ -165,8 +160,8 @@ class ThreadSubscriptionsWorkerStore(CacheInvalidationWorkerStore):
         room_id: str,
         thread_root_event_id: str,
         *,
-        automatic_event_orderings: Optional[EventOrderings],
-    ) -> Optional[Union[int, AutomaticSubscriptionConflicted]]:
+        automatic_event_orderings: EventOrderings | None,
+    ) -> int | AutomaticSubscriptionConflicted | None:
         """Updates a user's subscription settings for a specific thread root.
 
         If no change would be made to the subscription, does not produce any database change.
@@ -208,7 +203,7 @@ class ThreadSubscriptionsWorkerStore(CacheInvalidationWorkerStore):
 
         def _subscribe_user_to_thread_txn(
             txn: LoggingTransaction,
-        ) -> Optional[Union[int, AutomaticSubscriptionConflicted]]:
+        ) -> int | AutomaticSubscriptionConflicted | None:
             requested_automatic = automatic_event_orderings is not None
 
             row = self.db_pool.simple_select_one_txn(
@@ -310,7 +305,7 @@ class ThreadSubscriptionsWorkerStore(CacheInvalidationWorkerStore):
 
     async def unsubscribe_user_from_thread(
         self, user_id: str, room_id: str, thread_root_event_id: str
-    ) -> Optional[int]:
+    ) -> int | None:
         """Unsubscribes a user from a thread.
 
         If no change would be made to the subscription, does not produce any database change.
@@ -326,7 +321,7 @@ class ThreadSubscriptionsWorkerStore(CacheInvalidationWorkerStore):
 
         assert self._can_write_to_thread_subscriptions
 
-        def _unsubscribe_user_from_thread_txn(txn: LoggingTransaction) -> Optional[int]:
+        def _unsubscribe_user_from_thread_txn(txn: LoggingTransaction) -> int | None:
             already_subscribed = self.db_pool.simple_select_one_onecol_txn(
                 txn,
                 table="thread_subscriptions",
@@ -423,7 +418,7 @@ class ThreadSubscriptionsWorkerStore(CacheInvalidationWorkerStore):
     @cached(tree=True)
     async def get_subscription_for_thread(
         self, user_id: str, room_id: str, thread_root_event_id: str
-    ) -> Optional[ThreadSubscription]:
+    ) -> ThreadSubscription | None:
         """Get the thread subscription for a specific thread and user.
 
         Args:
@@ -479,7 +474,7 @@ class ThreadSubscriptionsWorkerStore(CacheInvalidationWorkerStore):
     @cached(max_entries=100)
     async def get_subscribers_to_thread(
         self, room_id: str, thread_root_event_id: str
-    ) -> FrozenSet[str]:
+    ) -> frozenset[str]:
         """
         Returns:
             the set of user_ids for local users who are subscribed to the given thread.
@@ -510,7 +505,7 @@ class ThreadSubscriptionsWorkerStore(CacheInvalidationWorkerStore):
 
     async def get_updated_thread_subscriptions(
         self, *, from_id: int, to_id: int, limit: int
-    ) -> List[Tuple[int, str, str, str]]:
+    ) -> list[tuple[int, str, str, str]]:
         """Get updates to thread subscriptions between two stream IDs.
 
         Args:
@@ -524,7 +519,7 @@ class ThreadSubscriptionsWorkerStore(CacheInvalidationWorkerStore):
 
         def get_updated_thread_subscriptions_txn(
             txn: LoggingTransaction,
-        ) -> List[Tuple[int, str, str, str]]:
+        ) -> list[tuple[int, str, str, str]]:
             sql = """
                 SELECT stream_id, user_id, room_id, event_id
                 FROM thread_subscriptions
@@ -534,7 +529,7 @@ class ThreadSubscriptionsWorkerStore(CacheInvalidationWorkerStore):
             """
 
             txn.execute(sql, (from_id, to_id, limit))
-            return cast(List[Tuple[int, str, str, str]], txn.fetchall())
+            return cast(list[tuple[int, str, str, str]], txn.fetchall())
 
         return await self.db_pool.runInteraction(
             "get_updated_thread_subscriptions",
@@ -543,7 +538,7 @@ class ThreadSubscriptionsWorkerStore(CacheInvalidationWorkerStore):
 
     async def get_latest_updated_thread_subscriptions_for_user(
         self, user_id: str, *, from_id: int, to_id: int, limit: int
-    ) -> List[Tuple[int, str, str, bool, Optional[bool]]]:
+    ) -> list[tuple[int, str, str, bool, bool | None]]:
         """Get the latest updates to thread subscriptions for a specific user.
 
         Args:
@@ -561,7 +556,7 @@ class ThreadSubscriptionsWorkerStore(CacheInvalidationWorkerStore):
 
         def get_updated_thread_subscriptions_for_user_txn(
             txn: LoggingTransaction,
-        ) -> List[Tuple[int, str, str, bool, Optional[bool]]]:
+        ) -> list[tuple[int, str, str, bool, bool | None]]:
             sql = """
                 WITH the_updates AS (
                     SELECT stream_id, room_id, event_id, subscribed, automatic
diff --git a/synapse/storage/databases/main/transactions.py b/synapse/storage/databases/main/transactions.py
index bfc324b80d..70c5b928fd 100644
--- a/synapse/storage/databases/main/transactions.py
+++ b/synapse/storage/databases/main/transactions.py
@@ -21,7 +21,7 @@
 
 import logging
 from enum import Enum
-from typing import TYPE_CHECKING, Iterable, List, Mapping, Optional, Tuple, cast
+from typing import TYPE_CHECKING, Iterable, Mapping, cast
 
 import attr
 from canonicaljson import encode_canonical_json
@@ -81,11 +81,11 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
         super().__init__(database, db_conn, hs)
 
         if hs.config.worker.run_background_tasks:
-            self._clock.looping_call(self._cleanup_transactions, 30 * 60 * 1000)
+            self.clock.looping_call(self._cleanup_transactions, 30 * 60 * 1000)
 
     @wrap_as_background_process("cleanup_transactions")
     async def _cleanup_transactions(self) -> None:
-        now = self._clock.time_msec()
+        now = self.clock.time_msec()
         day_ago = now - 24 * 60 * 60 * 1000
 
         def _cleanup_transactions_txn(txn: LoggingTransaction) -> None:
@@ -97,7 +97,7 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
 
     async def get_received_txn_response(
         self, transaction_id: str, origin: str
-    ) -> Optional[Tuple[int, JsonDict]]:
+    ) -> tuple[int, JsonDict] | None:
         """For an incoming transaction from a given origin, check if we have
         already responded to it. If so, return the response code and response
         body (as a dict).
@@ -120,7 +120,7 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
 
     def _get_received_txn_response(
         self, txn: LoggingTransaction, transaction_id: str, origin: str
-    ) -> Optional[Tuple[int, JsonDict]]:
+    ) -> tuple[int, JsonDict] | None:
         result = self.db_pool.simple_select_one_txn(
             txn,
             table="received_transactions",
@@ -160,7 +160,7 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
             insertion_values={
                 "response_code": code,
                 "response_json": db_binary_type(encode_canonical_json(response_dict)),
-                "ts": self._clock.time_msec(),
+                "ts": self.clock.time_msec(),
             },
             desc="set_received_txn_response",
         )
@@ -169,7 +169,7 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
     async def get_destination_retry_timings(
         self,
         destination: str,
-    ) -> Optional[DestinationRetryTimings]:
+    ) -> DestinationRetryTimings | None:
         """Gets the current retry timings (if any) for a given destination.
 
         Args:
@@ -190,7 +190,7 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
 
     def _get_destination_retry_timings(
         self, txn: LoggingTransaction, destination: str
-    ) -> Optional[DestinationRetryTimings]:
+    ) -> DestinationRetryTimings | None:
         result = self.db_pool.simple_select_one_txn(
             txn,
             table="destinations",
@@ -213,9 +213,9 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
     )
     async def get_destination_retry_timings_batch(
         self, destinations: StrCollection
-    ) -> Mapping[str, Optional[DestinationRetryTimings]]:
+    ) -> Mapping[str, DestinationRetryTimings | None]:
         rows = cast(
-            List[Tuple[str, Optional[int], Optional[int], Optional[int]]],
+            list[tuple[str, int | None, int | None, int | None]],
             await self.db_pool.simple_select_many_batch(
                 table="destinations",
                 iterable=destinations,
@@ -241,7 +241,7 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
     async def set_destination_retry_timings(
         self,
         destination: str,
-        failure_ts: Optional[int],
+        failure_ts: int | None,
         retry_last_ts: int,
         retry_interval: int,
     ) -> None:
@@ -269,7 +269,7 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
         self,
         txn: LoggingTransaction,
         destination: str,
-        failure_ts: Optional[int],
+        failure_ts: int | None,
         retry_last_ts: int,
         retry_interval: int,
     ) -> None:
@@ -337,7 +337,7 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
 
     async def get_destination_last_successful_stream_ordering(
         self, destination: str
-    ) -> Optional[int]:
+    ) -> int | None:
         """
         Gets the stream ordering of the PDU most-recently successfully sent
         to the specified destination, or None if this information has not been
@@ -377,7 +377,7 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
         self,
         destination: str,
         last_successful_stream_ordering: int,
-    ) -> List[str]:
+    ) -> list[str]:
         """
         Returns at most 50 event IDs and their corresponding stream_orderings
         that correspond to the oldest events that have not yet been sent to
@@ -403,7 +403,7 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
         txn: LoggingTransaction,
         destination: str,
         last_successful_stream_ordering: int,
-    ) -> List[str]:
+    ) -> list[str]:
         q = """
                 SELECT event_id FROM destination_rooms
                  JOIN events USING (stream_ordering)
@@ -420,8 +420,8 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
         return event_ids
 
     async def get_catch_up_outstanding_destinations(
-        self, after_destination: Optional[str]
-    ) -> List[str]:
+        self, after_destination: str | None
+    ) -> list[str]:
         """
         Get a list of destinations we should retry transaction sending to.
 
@@ -449,8 +449,8 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
 
     @staticmethod
     def _get_catch_up_outstanding_destinations_txn(
-        txn: LoggingTransaction, now_time_ms: int, after_destination: Optional[str]
-    ) -> List[str]:
+        txn: LoggingTransaction, now_time_ms: int, after_destination: str | None
+    ) -> list[str]:
         # We're looking for destinations which satisfy either of the following
         # conditions:
         #
@@ -537,11 +537,11 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
         self,
         start: int,
         limit: int,
-        destination: Optional[str] = None,
+        destination: str | None = None,
         order_by: str = DestinationSortOrder.DESTINATION.value,
         direction: Direction = Direction.FORWARDS,
-    ) -> Tuple[
-        List[Tuple[str, Optional[int], Optional[int], Optional[int], Optional[int]]],
+    ) -> tuple[
+        list[tuple[str, int | None, int | None, int | None, int | None]],
         int,
     ]:
         """Function to retrieve a paginated list of destinations.
@@ -566,10 +566,8 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
 
         def get_destinations_paginate_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[
-            List[
-                Tuple[str, Optional[int], Optional[int], Optional[int], Optional[int]]
-            ],
+        ) -> tuple[
+            list[tuple[str, int | None, int | None, int | None, int | None]],
             int,
         ]:
             order_by_column = DestinationSortOrder(order_by).value
@@ -579,7 +577,7 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
             else:
                 order = "ASC"
 
-            args: List[object] = []
+            args: list[object] = []
             where_statement = ""
             if destination:
                 args.extend(["%" + destination.lower() + "%"])
@@ -588,7 +586,7 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
             sql_base = f"FROM destinations {where_statement} "
             sql = f"SELECT COUNT(*) as total_destinations {sql_base}"
             txn.execute(sql, args)
-            count = cast(Tuple[int], txn.fetchone())[0]
+            count = cast(tuple[int], txn.fetchone())[0]
 
             sql = f"""
                 SELECT destination, retry_last_ts, retry_interval, failure_ts,
@@ -599,11 +597,7 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
             """
             txn.execute(sql, args + [limit, start])
             destinations = cast(
-                List[
-                    Tuple[
-                        str, Optional[int], Optional[int], Optional[int], Optional[int]
-                    ]
-                ],
+                list[tuple[str, int | None, int | None, int | None, int | None]],
                 txn.fetchall(),
             )
             return destinations, count
@@ -618,7 +612,7 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
         start: int,
         limit: int,
         direction: Direction = Direction.FORWARDS,
-    ) -> Tuple[List[Tuple[str, int]], int]:
+    ) -> tuple[list[tuple[str, int]], int]:
         """Function to retrieve a paginated list of destination's rooms.
         This will return a json list of rooms and the
         total number of rooms.
@@ -636,7 +630,7 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
 
         def get_destination_rooms_paginate_txn(
             txn: LoggingTransaction,
-        ) -> Tuple[List[Tuple[str, int]], int]:
+        ) -> tuple[list[tuple[str, int]], int]:
             if direction == Direction.BACKWARDS:
                 order = "DESC"
             else:
@@ -648,10 +642,10 @@ class TransactionWorkerStore(CacheInvalidationWorkerStore):
                 WHERE destination = ?
                 """
             txn.execute(sql, [destination])
-            count = cast(Tuple[int], txn.fetchone())[0]
+            count = cast(tuple[int], txn.fetchone())[0]
 
             rooms = cast(
-                List[Tuple[str, int]],
+                list[tuple[str, int]],
                 self.db_pool.simple_select_list_paginate_txn(
                     txn=txn,
                     table="destination_rooms",
diff --git a/synapse/storage/databases/main/ui_auth.py b/synapse/storage/databases/main/ui_auth.py
index 569925e39f..e523f0238a 100644
--- a/synapse/storage/databases/main/ui_auth.py
+++ b/synapse/storage/databases/main/ui_auth.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Any, Dict, List, Optional, Tuple, Union, cast
+from typing import Any, cast
 
 import attr
 
@@ -142,7 +142,7 @@ class UIAuthWorkerStore(SQLBaseStore):
         self,
         session_id: str,
         stage_type: str,
-        result: Union[str, bool, JsonDict],
+        result: str | bool | JsonDict,
     ) -> None:
         """
         Mark a session stage as completed.
@@ -170,7 +170,7 @@ class UIAuthWorkerStore(SQLBaseStore):
 
     async def get_completed_ui_auth_stages(
         self, session_id: str
-    ) -> Dict[str, Union[str, bool, JsonDict]]:
+    ) -> dict[str, str | bool | JsonDict]:
         """
         Retrieve the completed stages of a UI authentication session.
 
@@ -182,7 +182,7 @@ class UIAuthWorkerStore(SQLBaseStore):
         """
         results = {}
         rows = cast(
-            List[Tuple[str, str]],
+            list[tuple[str, str]],
             await self.db_pool.simple_select_list(
                 table="ui_auth_sessions_credentials",
                 keyvalues={"session_id": session_id},
@@ -262,7 +262,7 @@ class UIAuthWorkerStore(SQLBaseStore):
         )
 
     async def get_ui_auth_session_data(
-        self, session_id: str, key: str, default: Optional[Any] = None
+        self, session_id: str, key: str, default: Any | None = None
     ) -> Any:
         """
         Retrieve data stored with set_session_data
@@ -302,14 +302,14 @@ class UIAuthWorkerStore(SQLBaseStore):
     async def get_user_agents_ips_to_ui_auth_session(
         self,
         session_id: str,
-    ) -> List[Tuple[str, str]]:
+    ) -> list[tuple[str, str]]:
         """Get the given user agents / IPs used during the ui auth process
 
         Returns:
             List of user_agent/ip pairs
         """
         return cast(
-            List[Tuple[str, str]],
+            list[tuple[str, str]],
             await self.db_pool.simple_select_list(
                 table="ui_auth_sessions_ips",
                 keyvalues={"session_id": session_id},
@@ -353,7 +353,7 @@ class UIAuthWorkerStore(SQLBaseStore):
         # If a registration token was used, decrement the pending counter
         # before deleting the session.
         rows = cast(
-            List[Tuple[str]],
+            list[tuple[str]],
             self.db_pool.simple_select_many_txn(
                 txn,
                 table="ui_auth_sessions_credentials",
@@ -365,7 +365,7 @@ class UIAuthWorkerStore(SQLBaseStore):
         )
 
         # Get the tokens used and how much pending needs to be decremented by.
-        token_counts: Dict[str, int] = {}
+        token_counts: dict[str, int] = {}
         for r in rows:
             # If registration was successfully completed, the result of the
             # registration token stage for that session will be True.
@@ -378,7 +378,7 @@ class UIAuthWorkerStore(SQLBaseStore):
         # Update the `pending` counters.
         if len(token_counts) > 0:
             token_rows = cast(
-                List[Tuple[str, int]],
+                list[tuple[str, int]],
                 self.db_pool.simple_select_many_txn(
                     txn,
                     table="registration_tokens",
diff --git a/synapse/storage/databases/main/user_directory.py b/synapse/storage/databases/main/user_directory.py
index 9deb9ab73c..6c5abc71ae 100644
--- a/synapse/storage/databases/main/user_directory.py
+++ b/synapse/storage/databases/main/user_directory.py
@@ -26,11 +26,7 @@ from typing import (
     TYPE_CHECKING,
     Collection,
     Iterable,
-    List,
-    Optional,
     Sequence,
-    Set,
-    Tuple,
     TypedDict,
     cast,
 )
@@ -75,8 +71,8 @@ class _UserDirProfile:
     user_id: str
 
     # If the display name or avatar URL are unexpected types, replace with None
-    display_name: Optional[str] = attr.ib(default=None, converter=non_null_str_or_none)
-    avatar_url: Optional[str] = attr.ib(default=None, converter=non_null_str_or_none)
+    display_name: str | None = attr.ib(default=None, converter=non_null_str_or_none)
+    avatar_url: str | None = attr.ib(default=None, converter=non_null_str_or_none)
 
 
 class UserDirectoryBackgroundUpdateStore(StateDeltasStore):
@@ -209,7 +205,7 @@ class UserDirectoryBackgroundUpdateStore(StateDeltasStore):
 
         def _get_next_batch(
             txn: LoggingTransaction,
-        ) -> Optional[Sequence[Tuple[str, int]]]:
+        ) -> Sequence[tuple[str, int]] | None:
             # Only fetch 250 rooms, so we don't fetch too many at once, even
             # if those 250 rooms have less than batch_size state events.
             sql = """
@@ -218,7 +214,7 @@ class UserDirectoryBackgroundUpdateStore(StateDeltasStore):
                 LIMIT 250
             """ % (TEMP_TABLE + "_rooms",)
             txn.execute(sql)
-            rooms_to_work_on = cast(List[Tuple[str, int]], txn.fetchall())
+            rooms_to_work_on = cast(list[tuple[str, int]], txn.fetchall())
 
             if not rooms_to_work_on:
                 return None
@@ -355,28 +351,20 @@ class UserDirectoryBackgroundUpdateStore(StateDeltasStore):
 
         def _populate_user_directory_process_users_txn(
             txn: LoggingTransaction,
-        ) -> Optional[int]:
-            if self.database_engine.supports_returning:
-                # Note: we use an ORDER BY in the SELECT to force usage of an
-                # index. Otherwise, postgres does a sequential scan that is
-                # surprisingly slow (I think due to the fact it will read/skip
-                # over lots of already deleted rows).
-                sql = f"""
-                    DELETE FROM {TEMP_TABLE + "_users"}
-                    WHERE user_id IN (
-                        SELECT user_id FROM {TEMP_TABLE + "_users"} ORDER BY user_id LIMIT ?
-                    )
-                    RETURNING user_id
-                """
-                txn.execute(sql, (batch_size,))
-                user_result = cast(List[Tuple[str]], txn.fetchall())
-            else:
-                sql = "SELECT user_id FROM %s ORDER BY user_id LIMIT %s" % (
-                    TEMP_TABLE + "_users",
-                    str(batch_size),
+        ) -> int | None:
+            # Note: we use an ORDER BY in the SELECT to force usage of an
+            # index. Otherwise, postgres does a sequential scan that is
+            # surprisingly slow (I think due to the fact it will read/skip
+            # over lots of already deleted rows).
+            sql = f"""
+                DELETE FROM {TEMP_TABLE + "_users"}
+                WHERE user_id IN (
+                    SELECT user_id FROM {TEMP_TABLE + "_users"} ORDER BY user_id LIMIT ?
                 )
-                txn.execute(sql)
-                user_result = cast(List[Tuple[str]], txn.fetchall())
+                RETURNING user_id
+            """
+            txn.execute(sql, (batch_size,))
+            user_result = cast(list[tuple[str]], txn.fetchall())
 
             if not user_result:
                 return None
@@ -408,7 +396,7 @@ class UserDirectoryBackgroundUpdateStore(StateDeltasStore):
 
             # Next fetch their profiles. Note that not all users have profiles.
             profile_rows = cast(
-                List[Tuple[str, Optional[str], Optional[str]]],
+                list[tuple[str, str | None, str | None]],
                 self.db_pool.simple_select_many_txn(
                     txn,
                     table="profiles",
@@ -435,17 +423,6 @@ class UserDirectoryBackgroundUpdateStore(StateDeltasStore):
             # Actually insert the users with their profiles into the directory.
             self._update_profiles_in_user_dir_txn(txn, profiles_to_insert)
 
-            # We've finished processing the users. Delete it from the table, if
-            # we haven't already.
-            if not self.database_engine.supports_returning:
-                self.db_pool.simple_delete_many_txn(
-                    txn,
-                    table=TEMP_TABLE + "_users",
-                    column="user_id",
-                    values=users_to_work_on,
-                    keyvalues={},
-                )
-
             # Update the remaining counter.
             progress["remaining"] -= len(users_to_work_on)
             self.db_pool.updates._background_update_progress_txn(
@@ -514,7 +491,7 @@ class UserDirectoryBackgroundUpdateStore(StateDeltasStore):
         ]
 
         rows = cast(
-            List[Tuple[str, Optional[str]]],
+            list[tuple[str, str | None]],
             self.db_pool.simple_select_many_txn(
                 txn,
                 table="users",
@@ -608,7 +585,7 @@ class UserDirectoryBackgroundUpdateStore(StateDeltasStore):
 
     async def get_remote_servers_with_profiles_to_refresh(
         self, now_ts: int, limit: int
-    ) -> List[str]:
+    ) -> list[str]:
         """
         Get a list of up to `limit` server names which have users whose
         locally-cached profiles we believe to be stale
@@ -617,7 +594,7 @@ class UserDirectoryBackgroundUpdateStore(StateDeltasStore):
 
         def _get_remote_servers_with_refreshable_profiles_txn(
             txn: LoggingTransaction,
-        ) -> List[str]:
+        ) -> list[str]:
             sql = """
                 SELECT user_server_name
                 FROM user_directory_stale_remote_users
@@ -636,7 +613,7 @@ class UserDirectoryBackgroundUpdateStore(StateDeltasStore):
 
     async def get_remote_users_to_refresh_on_server(
         self, server_name: str, now_ts: int, limit: int
-    ) -> List[Tuple[str, int, int]]:
+    ) -> list[tuple[str, int, int]]:
         """
         Get a list of up to `limit` user IDs from the server `server_name`
         whose locally-cached profiles we believe to be stale
@@ -651,7 +628,7 @@ class UserDirectoryBackgroundUpdateStore(StateDeltasStore):
 
         def _get_remote_users_to_refresh_on_server_txn(
             txn: LoggingTransaction,
-        ) -> List[Tuple[str, int, int]]:
+        ) -> list[tuple[str, int, int]]:
             sql = """
                 SELECT user_id, retry_counter, next_try_at_ts
                 FROM user_directory_stale_remote_users
@@ -660,7 +637,7 @@ class UserDirectoryBackgroundUpdateStore(StateDeltasStore):
                 LIMIT ?
             """
             txn.execute(sql, (server_name, now_ts, limit))
-            return cast(List[Tuple[str, int, int]], txn.fetchall())
+            return cast(list[tuple[str, int, int]], txn.fetchall())
 
         return await self.db_pool.runInteraction(
             "get_remote_users_to_refresh_on_server",
@@ -668,7 +645,7 @@ class UserDirectoryBackgroundUpdateStore(StateDeltasStore):
         )
 
     async def update_profile_in_user_dir(
-        self, user_id: str, display_name: Optional[str], avatar_url: Optional[str]
+        self, user_id: str, display_name: str | None, avatar_url: str | None
     ) -> None:
         """
         Update or add a user's profile in the user directory.
@@ -771,7 +748,7 @@ class UserDirectoryBackgroundUpdateStore(StateDeltasStore):
             raise Exception("Unrecognized database engine")
 
     async def add_users_who_share_private_room(
-        self, room_id: str, user_id_tuples: Iterable[Tuple[str, str]]
+        self, room_id: str, user_id_tuples: Iterable[tuple[str, str]]
     ) -> None:
         """Insert entries into the users_who_share_private_rooms table. The first
         user should be a local user.
@@ -834,7 +811,7 @@ class UserDirectoryBackgroundUpdateStore(StateDeltasStore):
 
     async def _get_user_in_directory(
         self, user_id: str
-    ) -> Optional[Tuple[Optional[str], Optional[str]]]:
+    ) -> tuple[str | None, str | None] | None:
         """
         Fetch the user information in the user directory.
 
@@ -843,7 +820,7 @@ class UserDirectoryBackgroundUpdateStore(StateDeltasStore):
             avatar URL (both of which may be None).
         """
         return cast(
-            Optional[Tuple[Optional[str], Optional[str]]],
+            tuple[str | None, str | None] | None,
             await self.db_pool.simple_select_one(
                 table="user_directory",
                 keyvalues={"user_id": user_id},
@@ -853,7 +830,7 @@ class UserDirectoryBackgroundUpdateStore(StateDeltasStore):
             ),
         )
 
-    async def update_user_directory_stream_pos(self, stream_id: Optional[int]) -> None:
+    async def update_user_directory_stream_pos(self, stream_id: int | None) -> None:
         await self.db_pool.simple_update_one(
             table="user_directory_stream_pos",
             keyvalues={},
@@ -864,7 +841,7 @@ class UserDirectoryBackgroundUpdateStore(StateDeltasStore):
 
 class SearchResult(TypedDict):
     limited: bool
-    results: List[UserProfile]
+    results: list[UserProfile]
 
 
 class UserDirectoryStore(UserDirectoryBackgroundUpdateStore):
@@ -911,7 +888,7 @@ class UserDirectoryStore(UserDirectoryBackgroundUpdateStore):
             "remove_from_user_dir", _remove_from_user_dir_txn
         )
 
-    async def get_users_in_dir_due_to_room(self, room_id: str) -> Set[str]:
+    async def get_users_in_dir_due_to_room(self, room_id: str) -> set[str]:
         """Get all user_ids that are in the room directory because they're
         in the given room_id
         """
@@ -965,7 +942,7 @@ class UserDirectoryStore(UserDirectoryBackgroundUpdateStore):
             "remove_user_who_share_room", _remove_user_who_share_room_txn
         )
 
-    async def get_user_dir_rooms_user_is_in(self, user_id: str) -> List[str]:
+    async def get_user_dir_rooms_user_is_in(self, user_id: str) -> list[str]:
         """
         Returns the rooms that a user is in.
 
@@ -993,7 +970,7 @@ class UserDirectoryStore(UserDirectoryBackgroundUpdateStore):
         users.update(rows)
         return list(users)
 
-    async def get_user_directory_stream_pos(self) -> Optional[int]:
+    async def get_user_directory_stream_pos(self) -> int | None:
         """
         Get the stream ID of the user directory stream.
 
@@ -1031,7 +1008,7 @@ class UserDirectoryStore(UserDirectoryBackgroundUpdateStore):
                 }
         """
 
-        join_args: Tuple[str, ...] = (user_id,)
+        join_args: tuple[str, ...] = (user_id,)
 
         if self.hs.config.userdirectory.user_directory_search_all_users:
             where_clause = "user_id != ?"
@@ -1060,7 +1037,7 @@ class UserDirectoryStore(UserDirectoryBackgroundUpdateStore):
         # We allow manipulating the ranking algorithm by injecting statements
         # based on config options.
         additional_ordering_statements = []
-        ordering_arguments: Tuple[str, ...] = ()
+        ordering_arguments: tuple[str, ...] = ()
 
         if isinstance(self.database_engine, PostgresEngine):
             full_query, exact_query, prefix_query = _parse_query_postgres(search_term)
@@ -1166,7 +1143,7 @@ class UserDirectoryStore(UserDirectoryBackgroundUpdateStore):
             raise Exception("Unrecognized database engine")
 
         results = cast(
-            List[Tuple[str, Optional[str], Optional[str]]],
+            list[tuple[str, str | None, str | None]],
             await self.db_pool.execute("search_user_dir", sql, *args),
         )
 
@@ -1232,7 +1209,7 @@ def _parse_query_sqlite(search_term: str) -> str:
     return " & ".join("(%s* OR %s)" % (result, result) for result in results)
 
 
-def _parse_query_postgres(search_term: str) -> Tuple[str, str, str]:
+def _parse_query_postgres(search_term: str) -> tuple[str, str, str]:
     """Takes a plain unicode string from the user and converts it into a form
     that can be passed to the database.
     We use this so that we can add prefix matching, which isn't something
@@ -1263,7 +1240,7 @@ def _parse_query_postgres(search_term: str) -> Tuple[str, str, str]:
     return both, exact, prefix
 
 
-def _parse_words(search_term: str) -> List[str]:
+def _parse_words(search_term: str) -> list[str]:
     """Split the provided search string into a list of its words using ICU.
 
     Args:
@@ -1275,7 +1252,7 @@ def _parse_words(search_term: str) -> List[str]:
     return _parse_words_with_icu(search_term)
 
 
-def _parse_words_with_icu(search_term: str) -> List[str]:
+def _parse_words_with_icu(search_term: str) -> list[str]:
     """Break down the provided search string into its individual words using ICU
     (International Components for Unicode).
 
@@ -1298,7 +1275,7 @@ def _parse_words_with_icu(search_term: str) -> List[str]:
     #
     # In particular, user-71 in postgres gets tokenised to "user, -71", and this
     # will not match a query for "user, 71".
-    new_results: List[str] = []
+    new_results: list[str] = []
     i = 0
     while i < len(results):
         curr = results[i]
diff --git a/synapse/storage/databases/main/user_erasure_store.py b/synapse/storage/databases/main/user_erasure_store.py
index cceed484c3..f89f11e149 100644
--- a/synapse/storage/databases/main/user_erasure_store.py
+++ b/synapse/storage/databases/main/user_erasure_store.py
@@ -18,7 +18,7 @@
 #
 #
 
-from typing import Iterable, List, Mapping, Tuple, cast
+from typing import Iterable, Mapping, cast
 
 from synapse.storage.database import LoggingTransaction
 from synapse.storage.databases.main import CacheInvalidationWorkerStore
@@ -57,7 +57,7 @@ class UserErasureWorkerStore(CacheInvalidationWorkerStore):
             for each user, whether the user has requested erasure.
         """
         rows = cast(
-            List[Tuple[str]],
+            list[tuple[str]],
             await self.db_pool.simple_select_many_batch(
                 table="erased_users",
                 column="user_id",
diff --git a/synapse/storage/databases/state/bg_updates.py b/synapse/storage/databases/state/bg_updates.py
index ac38b2ab19..8c505041f0 100644
--- a/synapse/storage/databases/state/bg_updates.py
+++ b/synapse/storage/databases/state/bg_updates.py
@@ -22,12 +22,7 @@
 import logging
 from typing import (
     TYPE_CHECKING,
-    Dict,
-    List,
     Mapping,
-    Optional,
-    Tuple,
-    Union,
 )
 
 from synapse.logging.opentracing import tag_args, trace
@@ -85,7 +80,7 @@ class StateGroupBackgroundUpdateStore(SQLBaseStore):
         else:
             # We don't use WITH RECURSIVE on sqlite3 as there are distributions
             # that ship with an sqlite3 version that doesn't support it (e.g. wheezy)
-            next_group: Optional[int] = state_group
+            next_group: int | None = state_group
             count = 0
 
             while next_group:
@@ -106,8 +101,8 @@ class StateGroupBackgroundUpdateStore(SQLBaseStore):
     def _get_state_groups_from_groups_txn(
         self,
         txn: LoggingTransaction,
-        groups: List[int],
-        state_filter: Optional[StateFilter] = None,
+        groups: list[int],
+        state_filter: StateFilter | None = None,
     ) -> Mapping[int, StateMap[str]]:
         """
         Given a number of state groups, fetch the latest state for each group.
@@ -123,7 +118,7 @@ class StateGroupBackgroundUpdateStore(SQLBaseStore):
         if state_filter is None:
             state_filter = StateFilter.all()
 
-        results: Dict[int, MutableStateMap[str]] = {group: {} for group in groups}
+        results: dict[int, MutableStateMap[str]] = {group: {} for group in groups}
 
         if isinstance(self.database_engine, PostgresEngine):
             # Temporarily disable sequential scans in this transaction. This is
@@ -147,7 +142,7 @@ class StateGroupBackgroundUpdateStore(SQLBaseStore):
                 %s
             """
 
-            overall_select_query_args: List[Union[int, str]] = []
+            overall_select_query_args: list[int | str] = []
 
             # This is an optimization to create a select clause per-condition. This
             # makes the query planner a lot smarter on what rows should pull out in the
@@ -156,7 +151,7 @@ class StateGroupBackgroundUpdateStore(SQLBaseStore):
             use_condition_optimization = (
                 not state_filter.include_others and not state_filter.is_full()
             )
-            state_filter_condition_combos: List[Tuple[str, Optional[str]]] = []
+            state_filter_condition_combos: list[tuple[str, str | None]] = []
             # We don't need to caclculate this list if we're not using the condition
             # optimization
             if use_condition_optimization:
@@ -173,7 +168,7 @@ class StateGroupBackgroundUpdateStore(SQLBaseStore):
             # `filter_events_for_client` which just uses 2 conditions
             # (`EventTypes.RoomHistoryVisibility` and `EventTypes.Member`).
             if use_condition_optimization and len(state_filter_condition_combos) < 10:
-                select_clause_list: List[str] = []
+                select_clause_list: list[str] = []
                 for etype, skey in state_filter_condition_combos:
                     if skey is None:
                         where_clause = "(type = ?)"
@@ -216,7 +211,7 @@ class StateGroupBackgroundUpdateStore(SQLBaseStore):
                 """
 
             for group in groups:
-                args: List[Union[int, str]] = [group]
+                args: list[int | str] = [group]
                 args.extend(overall_select_query_args)
 
                 txn.execute(sql % (overall_select_clause,), args)
@@ -238,7 +233,7 @@ class StateGroupBackgroundUpdateStore(SQLBaseStore):
             #
             # We just haven't put in the time to refactor this.
             for group in groups:
-                next_group: Optional[int] = group
+                next_group: int | None = group
 
                 while next_group:
                     # We did this before by getting the list of group ids, and
@@ -347,7 +342,7 @@ class StateBackgroundUpdateStore(StateGroupBackgroundUpdateStore):
             )
             max_group = rows[0][0]
 
-        def reindex_txn(txn: LoggingTransaction) -> Tuple[bool, int]:
+        def reindex_txn(txn: LoggingTransaction) -> tuple[bool, int]:
             new_last_state_group = last_state_group
             for count in range(batch_size):
                 txn.execute(
diff --git a/synapse/storage/databases/state/deletion.py b/synapse/storage/databases/state/deletion.py
index 9b62c1d814..23150e8626 100644
--- a/synapse/storage/databases/state/deletion.py
+++ b/synapse/storage/databases/state/deletion.py
@@ -20,9 +20,6 @@ from typing import (
     AsyncIterator,
     Collection,
     Mapping,
-    Optional,
-    Set,
-    Tuple,
 )
 
 from synapse.events.snapshot import EventPersistencePair
@@ -233,7 +230,7 @@ class StateDeletionDataStore:
         any state groups referenced still exist and that they don't get deleted
         during this."""
 
-        referenced_state_groups: Set[int] = set()
+        referenced_state_groups: set[int] = set()
         for event, ctx in event_and_contexts:
             if ctx.rejected or event.internal_metadata.is_outlier():
                 continue
@@ -269,7 +266,7 @@ class StateDeletionDataStore:
             )
 
     def _mark_state_groups_as_persisting_txn(
-        self, txn: LoggingTransaction, state_groups: Set[int]
+        self, txn: LoggingTransaction, state_groups: set[int]
     ) -> None:
         """Marks the given state groups as being persisted."""
 
@@ -508,7 +505,7 @@ class StateDeletionDataStore:
 
     async def get_next_state_group_collection_to_delete(
         self,
-    ) -> Optional[Tuple[str, Mapping[int, int]]]:
+    ) -> tuple[str, Mapping[int, int]] | None:
         """Get the next set of state groups to try and delete
 
         Returns:
@@ -522,7 +519,7 @@ class StateDeletionDataStore:
     def _get_next_state_group_collection_to_delete_txn(
         self,
         txn: LoggingTransaction,
-    ) -> Optional[Tuple[str, Mapping[int, int]]]:
+    ) -> tuple[str, Mapping[int, int]] | None:
         """Implementation of `get_next_state_group_collection_to_delete`"""
 
         # We want to return chunks of state groups that were marked for deletion
diff --git a/synapse/storage/databases/state/store.py b/synapse/storage/databases/state/store.py
index 9b3b7e086f..d3ce7a8b55 100644
--- a/synapse/storage/databases/state/store.py
+++ b/synapse/storage/databases/state/store.py
@@ -22,13 +22,8 @@
 import logging
 from typing import (
     TYPE_CHECKING,
-    Dict,
     Iterable,
-    List,
     Mapping,
-    Optional,
-    Set,
-    Tuple,
     cast,
 )
 
@@ -73,8 +68,8 @@ class _GetStateGroupDelta:
     us use the iterable flag when caching
     """
 
-    prev_group: Optional[int]
-    delta_ids: Optional[StateMap[str]]
+    prev_group: int | None
+    delta_ids: StateMap[str] | None
 
     def __len__(self) -> int:
         return len(self.delta_ids) if self.delta_ids else 0
@@ -125,6 +120,7 @@ class StateGroupDataStore(StateBackgroundUpdateStore, SQLBaseStore):
 
         self._state_group_cache: DictionaryCache[int, StateKey, str] = DictionaryCache(
             name="*stateGroupCache*",
+            clock=hs.get_clock(),
             server_name=self.server_name,
             # TODO: this hasn't been tuned yet
             max_entries=50000,
@@ -132,6 +128,7 @@ class StateGroupDataStore(StateBackgroundUpdateStore, SQLBaseStore):
         self._state_group_members_cache: DictionaryCache[int, StateKey, str] = (
             DictionaryCache(
                 name="*stateGroupMembersCache*",
+                clock=hs.get_clock(),
                 server_name=self.server_name,
                 max_entries=500000,
             )
@@ -172,7 +169,7 @@ class StateGroupDataStore(StateBackgroundUpdateStore, SQLBaseStore):
                 return _GetStateGroupDelta(None, None)
 
             delta_ids = cast(
-                List[Tuple[str, str, str]],
+                list[tuple[str, str, str]],
                 self.db_pool.simple_select_list_txn(
                     txn,
                     table="state_groups_state",
@@ -197,8 +194,8 @@ class StateGroupDataStore(StateBackgroundUpdateStore, SQLBaseStore):
     @tag_args
     @cancellable
     async def _get_state_groups_from_groups(
-        self, groups: List[int], state_filter: StateFilter
-    ) -> Dict[int, StateMap[str]]:
+        self, groups: list[int], state_filter: StateFilter
+    ) -> dict[int, StateMap[str]]:
         """Returns the state groups for a given set of groups from the
         database, filtering on types of state events.
 
@@ -209,7 +206,7 @@ class StateGroupDataStore(StateBackgroundUpdateStore, SQLBaseStore):
         Returns:
             Dict of state group to state map.
         """
-        results: Dict[int, StateMap[str]] = {}
+        results: dict[int, StateMap[str]] = {}
 
         chunks = [groups[i : i + 100] for i in range(0, len(groups), 100)]
         for chunk in chunks:
@@ -230,7 +227,7 @@ class StateGroupDataStore(StateBackgroundUpdateStore, SQLBaseStore):
         cache: DictionaryCache[int, StateKey, str],
         group: int,
         state_filter: StateFilter,
-    ) -> Tuple[MutableStateMap[str], bool]:
+    ) -> tuple[MutableStateMap[str], bool]:
         """Checks if group is in cache. See `get_state_for_groups`
 
         Args:
@@ -281,8 +278,8 @@ class StateGroupDataStore(StateBackgroundUpdateStore, SQLBaseStore):
     @tag_args
     @cancellable
     async def _get_state_for_groups(
-        self, groups: Iterable[int], state_filter: Optional[StateFilter] = None
-    ) -> Dict[int, MutableStateMap[str]]:
+        self, groups: Iterable[int], state_filter: StateFilter | None = None
+    ) -> dict[int, MutableStateMap[str]]:
         """Gets the state at each of a list of state groups, optionally
         filtering by type/state_key
 
@@ -353,7 +350,7 @@ class StateGroupDataStore(StateBackgroundUpdateStore, SQLBaseStore):
         groups: Iterable[int],
         cache: DictionaryCache[int, StateKey, str],
         state_filter: StateFilter,
-    ) -> Tuple[Dict[int, MutableStateMap[str]], Set[int]]:
+    ) -> tuple[dict[int, MutableStateMap[str]], set[int]]:
         """Gets the state at each of a list of state groups, optionally
         filtering by type/state_key, querying from a specific cache.
 
@@ -385,7 +382,7 @@ class StateGroupDataStore(StateBackgroundUpdateStore, SQLBaseStore):
 
     def _insert_into_cache(
         self,
-        group_to_state_dict: Dict[int, StateMap[str]],
+        group_to_state_dict: dict[int, StateMap[str]],
         state_filter: StateFilter,
         cache_seq_num_members: int,
         cache_seq_num_non_members: int,
@@ -450,10 +447,10 @@ class StateGroupDataStore(StateBackgroundUpdateStore, SQLBaseStore):
     @tag_args
     async def store_state_deltas_for_batched(
         self,
-        events_and_context: List[Tuple[EventBase, UnpersistedEventContextBase]],
+        events_and_context: list[tuple[EventBase, UnpersistedEventContextBase]],
         room_id: str,
         prev_group: int,
-    ) -> List[Tuple[EventBase, UnpersistedEventContext]]:
+    ) -> list[tuple[EventBase, UnpersistedEventContext]]:
         """Generate and store state deltas for a group of events and contexts created to be
         batch persisted. Note that all the events must be in a linear chain (ie a <- b <- c).
 
@@ -467,9 +464,9 @@ class StateGroupDataStore(StateBackgroundUpdateStore, SQLBaseStore):
 
         def insert_deltas_group_txn(
             txn: LoggingTransaction,
-            events_and_context: List[Tuple[EventBase, UnpersistedEventContext]],
+            events_and_context: list[tuple[EventBase, UnpersistedEventContext]],
             prev_group: int,
-        ) -> List[Tuple[EventBase, UnpersistedEventContext]]:
+        ) -> list[tuple[EventBase, UnpersistedEventContext]]:
             """Generate and store state groups for the provided events and contexts.
 
             Requires that we have the state as a delta from the last persisted state group.
@@ -573,9 +570,9 @@ class StateGroupDataStore(StateBackgroundUpdateStore, SQLBaseStore):
         self,
         event_id: str,
         room_id: str,
-        prev_group: Optional[int],
-        delta_ids: Optional[StateMap[str]],
-        current_state_ids: Optional[StateMap[str]],
+        prev_group: int | None,
+        delta_ids: StateMap[str] | None,
+        current_state_ids: StateMap[str] | None,
     ) -> int:
         """Store a new set of state, returning a newly assigned state group.
 
@@ -604,7 +601,7 @@ class StateGroupDataStore(StateBackgroundUpdateStore, SQLBaseStore):
 
         def insert_delta_group_txn(
             txn: LoggingTransaction, prev_group: int, delta_ids: StateMap[str]
-        ) -> Optional[int]:
+        ) -> int | None:
             """Try and persist the new group as a delta.
 
             Requires that we have the state as a delta from a previous state group.
@@ -780,7 +777,7 @@ class StateGroupDataStore(StateBackgroundUpdateStore, SQLBaseStore):
         )
 
         rows = cast(
-            List[Tuple[int]],
+            list[tuple[int]],
             self.db_pool.simple_select_many_txn(
                 txn,
                 table="state_group_edges",
@@ -851,7 +848,7 @@ class StateGroupDataStore(StateBackgroundUpdateStore, SQLBaseStore):
     @tag_args
     async def get_previous_state_groups(
         self, state_groups: Iterable[int]
-    ) -> Dict[int, int]:
+    ) -> dict[int, int]:
         """Fetch the previous groups of the given state groups.
 
         Args:
@@ -862,7 +859,7 @@ class StateGroupDataStore(StateBackgroundUpdateStore, SQLBaseStore):
         """
 
         rows = cast(
-            List[Tuple[int, int]],
+            list[tuple[int, int]],
             await self.db_pool.simple_select_many_batch(
                 table="state_group_edges",
                 column="state_group",
@@ -879,7 +876,7 @@ class StateGroupDataStore(StateBackgroundUpdateStore, SQLBaseStore):
     @tag_args
     async def get_next_state_groups(
         self, state_groups: Iterable[int]
-    ) -> Dict[int, int]:
+    ) -> dict[int, int]:
         """Fetch the groups that have the given state groups as their previous
         state groups.
 
@@ -891,7 +888,7 @@ class StateGroupDataStore(StateBackgroundUpdateStore, SQLBaseStore):
         """
 
         rows = cast(
-            List[Tuple[int, int]],
+            list[tuple[int, int]],
             await self.db_pool.simple_select_many_batch(
                 table="state_group_edges",
                 column="prev_state_group",
diff --git a/synapse/storage/engines/_base.py b/synapse/storage/engines/_base.py
index 9fec42c2e0..026b742aad 100644
--- a/synapse/storage/engines/_base.py
+++ b/synapse/storage/engines/_base.py
@@ -20,7 +20,7 @@
 #
 import abc
 from enum import IntEnum
-from typing import TYPE_CHECKING, Any, Generic, Mapping, Optional, TypeVar
+from typing import TYPE_CHECKING, Any, Generic, Mapping, TypeVar
 
 from synapse.storage.types import Connection, Cursor, DBAPI2Module
 
@@ -63,12 +63,6 @@ class BaseDatabaseEngine(Generic[ConnectionType, CursorType], metaclass=abc.ABCM
         """
         ...
 
-    @property
-    @abc.abstractmethod
-    def supports_returning(self) -> bool:
-        """Do we support the `RETURNING` clause in insert/update/delete?"""
-        ...
-
     @abc.abstractmethod
     def check_database(
         self, db_conn: ConnectionType, allow_outdated_version: bool = False
@@ -129,7 +123,7 @@ class BaseDatabaseEngine(Generic[ConnectionType, CursorType], metaclass=abc.ABCM
 
     @abc.abstractmethod
     def attempt_to_set_isolation_level(
-        self, conn: ConnectionType, isolation_level: Optional[int]
+        self, conn: ConnectionType, isolation_level: int | None
     ) -> None:
         """Attempt to set the connections isolation level.
 
diff --git a/synapse/storage/engines/postgres.py b/synapse/storage/engines/postgres.py
index e4cd359201..cc7e5508fd 100644
--- a/synapse/storage/engines/postgres.py
+++ b/synapse/storage/engines/postgres.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Any, Mapping, NoReturn, Optional, Tuple, cast
+from typing import TYPE_CHECKING, Any, Mapping, NoReturn, cast
 
 import psycopg2.extensions
 
@@ -60,10 +60,10 @@ class PostgresEngine(
         # some degenerate query plan has been created and the client has probably
         # timed out/walked off anyway.
         # This is in milliseconds.
-        self.statement_timeout: Optional[int] = database_config.get(
+        self.statement_timeout: int | None = database_config.get(
             "statement_timeout", 60 * 60 * 1000
         )
-        self._version: Optional[int] = None  # unknown as yet
+        self._version: int | None = None  # unknown as yet
 
         self.isolation_level_map: Mapping[int, int] = {
             IsolationLevel.READ_COMMITTED: psycopg2.extensions.ISOLATION_LEVEL_READ_COMMITTED,
@@ -79,11 +79,11 @@ class PostgresEngine(
     def single_threaded(self) -> bool:
         return False
 
-    def get_db_locale(self, txn: Cursor) -> Tuple[str, str]:
+    def get_db_locale(self, txn: Cursor) -> tuple[str, str]:
         txn.execute(
             "SELECT datcollate, datctype FROM pg_database WHERE datname = current_database()"
         )
-        collation, ctype = cast(Tuple[str, str], txn.fetchone())
+        collation, ctype = cast(tuple[str, str], txn.fetchone())
         return collation, ctype
 
     def check_database(
@@ -193,11 +193,6 @@ class PostgresEngine(
         """Do we support using `a = ANY(?)` and passing a list"""
         return True
 
-    @property
-    def supports_returning(self) -> bool:
-        """Do we support the `RETURNING` clause in insert/update/delete?"""
-        return True
-
     def is_deadlock(self, error: Exception) -> bool:
         if isinstance(error, psycopg2.DatabaseError):
             # https://www.postgresql.org/docs/current/static/errcodes-appendix.html
@@ -239,7 +234,7 @@ class PostgresEngine(
         return conn.set_session(autocommit=autocommit)
 
     def attempt_to_set_isolation_level(
-        self, conn: psycopg2.extensions.connection, isolation_level: Optional[int]
+        self, conn: psycopg2.extensions.connection, isolation_level: int | None
     ) -> None:
         if isolation_level is None:
             isolation_level = self.default_isolation_level
diff --git a/synapse/storage/engines/sqlite.py b/synapse/storage/engines/sqlite.py
index 9d1795ebe5..3b1b19c00e 100644
--- a/synapse/storage/engines/sqlite.py
+++ b/synapse/storage/engines/sqlite.py
@@ -22,7 +22,7 @@ import platform
 import sqlite3
 import struct
 import threading
-from typing import TYPE_CHECKING, Any, List, Mapping, Optional
+from typing import TYPE_CHECKING, Any, Mapping
 
 from synapse.storage.engines import BaseDatabaseEngine
 from synapse.storage.engines._base import AUTO_INCREMENT_PRIMARY_KEYPLACEHOLDER
@@ -45,7 +45,7 @@ class Sqlite3Engine(BaseDatabaseEngine[sqlite3.Connection, sqlite3.Cursor]):
         # A connection to a database that has already been prepared, to use as a
         # base for an in-memory connection. This is used during unit tests to
         # speed up setting up the DB.
-        self._prepped_conn: Optional[sqlite3.Connection] = database_config.get(
+        self._prepped_conn: sqlite3.Connection | None = database_config.get(
             "_TEST_PREPPED_CONN"
         )
 
@@ -68,11 +68,6 @@ class Sqlite3Engine(BaseDatabaseEngine[sqlite3.Connection, sqlite3.Cursor]):
         """Do we support using `a = ANY(?)` and passing a list"""
         return False
 
-    @property
-    def supports_returning(self) -> bool:
-        """Do we support the `RETURNING` clause in insert/update/delete?"""
-        return sqlite3.sqlite_version_info >= (3, 35, 0)
-
     def check_database(
         self, db_conn: sqlite3.Connection, allow_outdated_version: bool = False
     ) -> None:
@@ -80,8 +75,8 @@ class Sqlite3Engine(BaseDatabaseEngine[sqlite3.Connection, sqlite3.Cursor]):
             # Synapse is untested against older SQLite versions, and we don't want
             # to let users upgrade to a version of Synapse with broken support for their
             # sqlite version, because it risks leaving them with a half-upgraded db.
-            if sqlite3.sqlite_version_info < (3, 27, 0):
-                raise RuntimeError("Synapse requires sqlite 3.27 or above.")
+            if sqlite3.sqlite_version_info < (3, 37, 2):
+                raise RuntimeError("Synapse requires sqlite 3.37.2 or above.")
 
     def check_new_database(self, txn: Cursor) -> None:
         """Gets called when setting up a brand new database. This allows us to
@@ -146,7 +141,7 @@ class Sqlite3Engine(BaseDatabaseEngine[sqlite3.Connection, sqlite3.Cursor]):
         pass
 
     def attempt_to_set_isolation_level(
-        self, conn: sqlite3.Connection, isolation_level: Optional[int]
+        self, conn: sqlite3.Connection, isolation_level: int | None
     ) -> None:
         # All transactions are SERIALIZABLE by default in sqlite
         pass
@@ -182,7 +177,7 @@ class Sqlite3Engine(BaseDatabaseEngine[sqlite3.Connection, sqlite3.Cursor]):
 # Following functions taken from: https://github.com/coleifer/peewee
 
 
-def _parse_match_info(buf: bytes) -> List[int]:
+def _parse_match_info(buf: bytes) -> list[int]:
     bufsize = len(buf)
     return [struct.unpack("@I", buf[i : i + 4])[0] for i in range(0, bufsize, 4)]
 
diff --git a/synapse/storage/invite_rule.py b/synapse/storage/invite_rule.py
index f63390871e..3de77e8c21 100644
--- a/synapse/storage/invite_rule.py
+++ b/synapse/storage/invite_rule.py
@@ -1,6 +1,6 @@
 import logging
 from enum import Enum
-from typing import Optional, Pattern
+from typing import Pattern
 
 from matrix_common.regex import glob_to_regex
 
@@ -20,7 +20,7 @@ class InviteRule(Enum):
 class InviteRulesConfig:
     """Class to determine if a given user permits an invite from another user, and the action to take."""
 
-    def __init__(self, account_data: Optional[JsonMapping]):
+    def __init__(self, account_data: JsonMapping | None):
         self.allowed_users: list[Pattern[str]] = []
         self.ignored_users: list[Pattern[str]] = []
         self.blocked_users: list[Pattern[str]] = []
@@ -30,7 +30,7 @@ class InviteRulesConfig:
         self.blocked_servers: list[Pattern[str]] = []
 
         def process_field(
-            values: Optional[list[str]],
+            values: list[str] | None,
             ruleset: list[Pattern[str]],
             rule: InviteRule,
         ) -> None:
diff --git a/synapse/storage/prepare_database.py b/synapse/storage/prepare_database.py
index bf087702ea..2def1e130c 100644
--- a/synapse/storage/prepare_database.py
+++ b/synapse/storage/prepare_database.py
@@ -28,10 +28,7 @@ from typing import (
     Counter as CounterType,
     Generator,
     Iterable,
-    List,
-    Optional,
     TextIO,
-    Tuple,
 )
 
 import attr
@@ -77,7 +74,7 @@ class _SchemaState:
     current_version: int = attr.ib()
     """The current schema version of the database"""
 
-    compat_version: Optional[int] = attr.ib()
+    compat_version: int | None = attr.ib()
     """The SCHEMA_VERSION of the oldest version of Synapse for this database
 
     If this is None, we have an old version of the database without the necessary
@@ -97,7 +94,7 @@ class _SchemaState:
 def prepare_database(
     db_conn: LoggingDatabaseConnection,
     database_engine: BaseDatabaseEngine,
-    config: Optional[HomeServerConfig],
+    config: HomeServerConfig | None,
     databases: Collection[str] = ("main", "state"),
 ) -> None:
     """Prepares a physical database for usage. Will either create all necessary tables
@@ -270,7 +267,7 @@ def _setup_new_database(
         for database in databases
     )
 
-    directory_entries: List[_DirectoryListing] = []
+    directory_entries: list[_DirectoryListing] = []
     for directory in directories:
         directory_entries.extend(
             _DirectoryListing(file_name, os.path.join(directory, file_name))
@@ -309,7 +306,7 @@ def _upgrade_existing_database(
     cur: LoggingTransaction,
     current_schema_state: _SchemaState,
     database_engine: BaseDatabaseEngine,
-    config: Optional[HomeServerConfig],
+    config: HomeServerConfig | None,
     databases: Collection[str],
     is_empty: bool = False,
 ) -> None:
@@ -453,7 +450,7 @@ def _upgrade_existing_database(
         file_name_counter: CounterType[str] = Counter()
 
         # Now find which directories have anything of interest.
-        directory_entries: List[_DirectoryListing] = []
+        directory_entries: list[_DirectoryListing] = []
         for directory in directories:
             logger.debug("Looking for schema deltas in %s", directory)
             try:
@@ -593,7 +590,7 @@ def _apply_module_schema_files(
     cur: Cursor,
     database_engine: BaseDatabaseEngine,
     modname: str,
-    names_and_streams: Iterable[Tuple[str, TextIO]],
+    names_and_streams: Iterable[tuple[str, TextIO]],
 ) -> None:
     """Apply the module schemas for a single module
 
@@ -685,7 +682,7 @@ def execute_statements_from_stream(cur: Cursor, f: TextIO) -> None:
 
 def _get_or_create_schema_state(
     txn: Cursor, database_engine: BaseDatabaseEngine
-) -> Optional[_SchemaState]:
+) -> _SchemaState | None:
     # Bluntly try creating the schema_version tables.
     sql_path = os.path.join(schema_path, "common", "schema_version.sql")
     database_engine.execute_script_file(txn, sql_path)
@@ -700,7 +697,7 @@ def _get_or_create_schema_state(
     current_version = int(row[0])
     upgraded = bool(row[1])
 
-    compat_version: Optional[int] = None
+    compat_version: int | None = None
     txn.execute("SELECT compat_version FROM schema_compat_version")
     row = txn.fetchone()
     if row is not None:
diff --git a/synapse/storage/roommember.py b/synapse/storage/roommember.py
index 9dc6c395e8..4c1ace28e7 100644
--- a/synapse/storage/roommember.py
+++ b/synapse/storage/roommember.py
@@ -20,7 +20,6 @@
 #
 
 import logging
-from typing import List, Optional, Tuple
 
 import attr
 
@@ -42,14 +41,14 @@ class RoomsForUser:
 @attr.s(slots=True, frozen=True, weakref_slot=False, auto_attribs=True)
 class RoomsForUserSlidingSync:
     room_id: str
-    sender: Optional[str]
+    sender: str | None
     membership: str
-    event_id: Optional[str]
+    event_id: str | None
     event_pos: PersistedEventPosition
     room_version_id: str
 
     has_known_state: bool
-    room_type: Optional[str]
+    room_type: str | None
     is_encrypted: bool
 
 
@@ -60,9 +59,9 @@ class RoomsForUserStateReset:
     without a corresponding event so that information isn't always available."""
 
     room_id: str
-    sender: Optional[str]
+    sender: str | None
     membership: str
-    event_id: Optional[str]
+    event_id: str | None
     event_pos: PersistedEventPosition
     room_version_id: str
 
@@ -75,8 +74,8 @@ class GetRoomsForUserWithStreamOrdering:
 
 @attr.s(slots=True, frozen=True, weakref_slot=False, auto_attribs=True)
 class ProfileInfo:
-    avatar_url: Optional[str]
-    display_name: Optional[str]
+    avatar_url: str | None
+    display_name: str | None
 
 
 # TODO This is used as a cached value and is mutable.
@@ -84,6 +83,6 @@ class ProfileInfo:
 class MemberSummary:
     # A truncated list of (user_id, event_id) tuples for users of a given
     # membership type, suitable for use in calculating heroes for a room.
-    members: List[Tuple[str, str]]
+    members: list[tuple[str, str]]
     # The total number of users of a given membership type.
     count: int
diff --git a/synapse/storage/schema/main/delta/30/as_users.py b/synapse/storage/schema/main/delta/30/as_users.py
index 060217575b..b7e9a11c2f 100644
--- a/synapse/storage/schema/main/delta/30/as_users.py
+++ b/synapse/storage/schema/main/delta/30/as_users.py
@@ -19,7 +19,7 @@
 #
 #
 import logging
-from typing import Dict, Iterable, List, Tuple, cast
+from typing import Iterable, cast
 
 from synapse.config.appservice import load_appservices
 from synapse.config.homeserver import HomeServerConfig
@@ -44,7 +44,7 @@ def run_upgrade(
     config: HomeServerConfig,
 ) -> None:
     cur.execute("SELECT name FROM users")
-    rows = cast(Iterable[Tuple[str]], cur.fetchall())
+    rows = cast(Iterable[tuple[str]], cur.fetchall())
 
     config_files = []
     try:
@@ -54,7 +54,7 @@ def run_upgrade(
 
     appservices = load_appservices(config.server.server_name, config_files)
 
-    owned: Dict[str, List[str]] = {}
+    owned: dict[str, list[str]] = {}
 
     for row in rows:
         user_id = row[0]
diff --git a/synapse/storage/types.py b/synapse/storage/types.py
index 4329d88c9a..ad9e5391e3 100644
--- a/synapse/storage/types.py
+++ b/synapse/storage/types.py
@@ -23,21 +23,16 @@ from typing import (
     Any,
     Callable,
     Iterator,
-    List,
     Mapping,
-    Optional,
     Protocol,
     Sequence,
-    Tuple,
-    Type,
-    Union,
 )
 
 """
 Some very basic protocol definitions for the DB-API2 classes specified in PEP-249
 """
 
-SQLQueryParameters = Union[Sequence[Any], Mapping[str, Any]]
+SQLQueryParameters = Sequence[Any] | Mapping[str, Any]
 
 
 class Cursor(Protocol):
@@ -47,16 +42,16 @@ class Cursor(Protocol):
         self, sql: str, parameters: Sequence[SQLQueryParameters]
     ) -> Any: ...
 
-    def fetchone(self) -> Optional[Tuple]: ...
+    def fetchone(self) -> tuple | None: ...
 
-    def fetchmany(self, size: Optional[int] = ...) -> List[Tuple]: ...
+    def fetchmany(self, size: int | None = ...) -> list[tuple]: ...
 
-    def fetchall(self) -> List[Tuple]: ...
+    def fetchall(self) -> list[tuple]: ...
 
     @property
     def description(
         self,
-    ) -> Optional[Sequence[Any]]:
+    ) -> Sequence[Any] | None:
         # At the time of writing, Synapse only assumes that `column[0]: str` for each
         # `column in description`. Since this is hard to express in the type system, and
         # as this is rarely used in Synapse, we deem `column: Any` good enough.
@@ -66,7 +61,7 @@ class Cursor(Protocol):
     def rowcount(self) -> int:
         return 0
 
-    def __iter__(self) -> Iterator[Tuple]: ...
+    def __iter__(self) -> Iterator[tuple]: ...
 
     def close(self) -> None: ...
 
@@ -84,10 +79,10 @@ class Connection(Protocol):
 
     def __exit__(
         self,
-        exc_type: Optional[Type[BaseException]],
-        exc_value: Optional[BaseException],
-        traceback: Optional[TracebackType],
-    ) -> Optional[bool]: ...
+        exc_type: type[BaseException] | None,
+        exc_value: BaseException | None,
+        traceback: TracebackType | None,
+    ) -> bool | None: ...
 
 
 class DBAPI2Module(Protocol):
@@ -117,20 +112,20 @@ class DBAPI2Module(Protocol):
     # explain why this is necessary for safety. TL;DR: we shouldn't be able to write
     # to `x`, only read from it. See also https://github.com/python/mypy/issues/6002 .
     @property
-    def Warning(self) -> Type[Exception]: ...
+    def Warning(self) -> type[Exception]: ...
 
     @property
-    def Error(self) -> Type[Exception]: ...
+    def Error(self) -> type[Exception]: ...
 
     # Errors are divided into `InterfaceError`s (something went wrong in the database
     # driver) and `DatabaseError`s (something went wrong in the database). These are
     # both subclasses of `Error`, but we can't currently express this in type
     # annotations due to https://github.com/python/mypy/issues/8397
     @property
-    def InterfaceError(self) -> Type[Exception]: ...
+    def InterfaceError(self) -> type[Exception]: ...
 
     @property
-    def DatabaseError(self) -> Type[Exception]: ...
+    def DatabaseError(self) -> type[Exception]: ...
 
     # Everything below is a subclass of `DatabaseError`.
 
@@ -139,7 +134,7 @@ class DBAPI2Module(Protocol):
     # - An invalid date time was provided.
     # - A string contained a null code point.
     @property
-    def DataError(self) -> Type[Exception]: ...
+    def DataError(self) -> type[Exception]: ...
 
     # Roughly: something went wrong in the database, but it's not within the application
     # programmer's control. Examples:
@@ -150,18 +145,18 @@ class DBAPI2Module(Protocol):
     # - The database ran out of resources, such as storage, memory, connections, etc.
     # - The database encountered an error from the operating system.
     @property
-    def OperationalError(self) -> Type[Exception]: ...
+    def OperationalError(self) -> type[Exception]: ...
 
     # Roughly: we've given the database data which breaks a rule we asked it to enforce.
     # Examples:
     # - Stop, criminal scum! You violated the foreign key constraint
     # - Also check constraints, non-null constraints, etc.
     @property
-    def IntegrityError(self) -> Type[Exception]: ...
+    def IntegrityError(self) -> type[Exception]: ...
 
     # Roughly: something went wrong within the database server itself.
     @property
-    def InternalError(self) -> Type[Exception]: ...
+    def InternalError(self) -> type[Exception]: ...
 
     # Roughly: the application did something silly that needs to be fixed. Examples:
     # - We don't have permissions to do something.
@@ -169,11 +164,11 @@ class DBAPI2Module(Protocol):
     # - We tried to use a reserved name.
     # - We referred to a column that doesn't exist.
     @property
-    def ProgrammingError(self) -> Type[Exception]: ...
+    def ProgrammingError(self) -> type[Exception]: ...
 
     # Roughly: we've tried to do something that this database doesn't support.
     @property
-    def NotSupportedError(self) -> Type[Exception]: ...
+    def NotSupportedError(self) -> type[Exception]: ...
 
     # We originally wrote
     # def connect(self, *args, **kwargs) -> Connection: ...
diff --git a/synapse/storage/util/id_generators.py b/synapse/storage/util/id_generators.py
index 1b7c5dac7a..66c993cbd9 100644
--- a/synapse/storage/util/id_generators.py
+++ b/synapse/storage/util/id_generators.py
@@ -28,17 +28,10 @@ from typing import (
     TYPE_CHECKING,
     AsyncContextManager,
     ContextManager,
-    Dict,
     Generic,
     Iterable,
-    List,
-    Optional,
     Sequence,
-    Set,
-    Tuple,
-    Type,
     TypeVar,
-    Union,
     cast,
 )
 
@@ -223,9 +216,9 @@ class MultiWriterIdGenerator(AbstractStreamIdGenerator):
         stream_name: str,
         server_name: str,
         instance_name: str,
-        tables: List[Tuple[str, str, str]],
+        tables: list[tuple[str, str, str]],
         sequence_name: str,
-        writers: List[str],
+        writers: list[str],
         positive: bool = True,
     ) -> None:
         self._db = db
@@ -243,7 +236,7 @@ class MultiWriterIdGenerator(AbstractStreamIdGenerator):
         # Note: If we are a negative stream then we still store all the IDs as
         # positive to make life easier for us, and simply negate the IDs when we
         # return them.
-        self._current_positions: Dict[str, int] = {}
+        self._current_positions: dict[str, int] = {}
 
         # Set of local IDs that we're still processing. The current position
         # should be less than the minimum of this set (if not empty).
@@ -260,7 +253,7 @@ class MultiWriterIdGenerator(AbstractStreamIdGenerator):
 
         # Set of local IDs that we've processed that are larger than the current
         # position, due to there being smaller unpersisted IDs.
-        self._finished_ids: Set[int] = set()
+        self._finished_ids: set[int] = set()
 
         # We track the max position where we know everything before has been
         # persisted. This is done by a) looking at the min across all instances
@@ -281,7 +274,7 @@ class MultiWriterIdGenerator(AbstractStreamIdGenerator):
         self._persisted_upto_position = (
             min(self._current_positions.values()) if self._current_positions else 1
         )
-        self._known_persisted_positions: List[int] = []
+        self._known_persisted_positions: list[int] = []
 
         # The maximum stream ID that we have seen been allocated across any writer.
         # Since this defaults to 1, this means that ID 1 is assumed to have already
@@ -348,7 +341,7 @@ class MultiWriterIdGenerator(AbstractStreamIdGenerator):
     def _load_current_ids(
         self,
         db_conn: LoggingDatabaseConnection,
-        tables: List[Tuple[str, str, str]],
+        tables: list[tuple[str, str, str]],
         sequence_name: str,
     ) -> None:
         cur = db_conn.cursor(txn_name="_load_current_ids")
@@ -439,7 +432,7 @@ class MultiWriterIdGenerator(AbstractStreamIdGenerator):
 
             self._persisted_upto_position = min_stream_id
 
-            rows: List[Tuple[str, int]] = []
+            rows: list[tuple[str, int]] = []
             for table, instance_column, id_column in tables:
                 sql = """
                     SELECT %(instance)s, %(id)s FROM %(table)s
@@ -453,13 +446,13 @@ class MultiWriterIdGenerator(AbstractStreamIdGenerator):
                 cur.execute(sql, (min_stream_id * self._return_factor,))
 
                 # Cast safety: this corresponds to the types returned by the query above.
-                rows.extend(cast(Iterable[Tuple[str, int]], cur))
+                rows.extend(cast(Iterable[tuple[str, int]], cur))
 
             # Sort by stream_id (ascending, lowest -> highest) so that we handle
             # rows in order for each instance because we don't want to overwrite
             # the current_position of an instance to a lower stream ID than
             # we're actually at.
-            def sort_by_stream_id_key_func(row: Tuple[str, int]) -> int:
+            def sort_by_stream_id_key_func(row: tuple[str, int]) -> int:
                 (instance, stream_id) = row
                 # If `stream_id` is ever `None`, we will see a `TypeError: '<'
                 # not supported between instances of 'NoneType' and 'X'` error.
@@ -492,7 +485,7 @@ class MultiWriterIdGenerator(AbstractStreamIdGenerator):
         stream_ids = self._load_next_mult_id_txn(txn, 1)
         return stream_ids[0]
 
-    def _load_next_mult_id_txn(self, txn: Cursor, n: int) -> List[int]:
+    def _load_next_mult_id_txn(self, txn: Cursor, n: int) -> list[int]:
         # We need to track that we've requested some more stream IDs, and what
         # the current max allocated stream ID is. This is to prevent a race
         # where we've been allocated stream IDs but they have not yet been added
@@ -529,7 +522,7 @@ class MultiWriterIdGenerator(AbstractStreamIdGenerator):
             AsyncContextManager[int], _MultiWriterCtxManager(self, self._notifier)
         )
 
-    def get_next_mult(self, n: int) -> AsyncContextManager[List[int]]:
+    def get_next_mult(self, n: int) -> AsyncContextManager[list[int]]:
         # If we have a list of instances that are allowed to write to this
         # stream, make sure we're in it.
         if self._writers and self._instance_name not in self._writers:
@@ -537,7 +530,7 @@ class MultiWriterIdGenerator(AbstractStreamIdGenerator):
 
         # Cast safety: see get_next.
         return cast(
-            AsyncContextManager[List[int]],
+            AsyncContextManager[list[int]],
             _MultiWriterCtxManager(self, self._notifier, n),
         )
 
@@ -578,7 +571,7 @@ class MultiWriterIdGenerator(AbstractStreamIdGenerator):
 
         return self._return_factor * next_id
 
-    def get_next_mult_txn(self, txn: LoggingTransaction, n: int) -> List[int]:
+    def get_next_mult_txn(self, txn: LoggingTransaction, n: int) -> list[int]:
         """
         Usage:
 
@@ -615,7 +608,7 @@ class MultiWriterIdGenerator(AbstractStreamIdGenerator):
 
         return [self._return_factor * next_id for next_id in next_ids]
 
-    def _mark_ids_as_finished(self, next_ids: List[int]) -> None:
+    def _mark_ids_as_finished(self, next_ids: list[int]) -> None:
         """These IDs have finished being processed so we should advance the
         current position if possible.
         """
@@ -624,7 +617,7 @@ class MultiWriterIdGenerator(AbstractStreamIdGenerator):
             self._unfinished_ids.difference_update(next_ids)
             self._finished_ids.update(next_ids)
 
-            new_cur: Optional[int] = None
+            new_cur: int | None = None
 
             if self._unfinished_ids or self._in_flight_fetches:
                 # If there are unfinished IDs then the new position will be the
@@ -707,7 +700,7 @@ class MultiWriterIdGenerator(AbstractStreamIdGenerator):
                 self._instance_name, self._persisted_upto_position
             )
 
-    def get_positions(self) -> Dict[str, int]:
+    def get_positions(self) -> dict[str, int]:
         """Get a copy of the current positon map.
 
         Note that this won't necessarily include all configured writers if some
@@ -849,10 +842,10 @@ class _AsyncCtxManagerWrapper(Generic[T]):
 
     async def __aexit__(
         self,
-        exc_type: Optional[Type[BaseException]],
-        exc: Optional[BaseException],
-        tb: Optional[TracebackType],
-    ) -> Optional[bool]:
+        exc_type: type[BaseException] | None,
+        exc: BaseException | None,
+        tb: TracebackType | None,
+    ) -> bool | None:
         return self.inner.__exit__(exc_type, exc, tb)
 
 
@@ -862,10 +855,10 @@ class _MultiWriterCtxManager:
 
     id_gen: MultiWriterIdGenerator
     notifier: "ReplicationNotifier"
-    multiple_ids: Optional[int] = None
-    stream_ids: List[int] = attr.Factory(list)
+    multiple_ids: int | None = None
+    stream_ids: list[int] = attr.Factory(list)
 
-    async def __aenter__(self) -> Union[int, List[int]]:
+    async def __aenter__(self) -> int | list[int]:
         # It's safe to run this in autocommit mode as fetching values from a
         # sequence ignores transaction semantics anyway.
         self.stream_ids = await self.id_gen._db.runInteraction(
@@ -882,9 +875,9 @@ class _MultiWriterCtxManager:
 
     async def __aexit__(
         self,
-        exc_type: Optional[Type[BaseException]],
-        exc: Optional[BaseException],
-        tb: Optional[TracebackType],
+        exc_type: type[BaseException] | None,
+        exc: BaseException | None,
+        tb: TracebackType | None,
     ) -> bool:
         self.id_gen._mark_ids_as_finished(self.stream_ids)
 
diff --git a/synapse/storage/util/partial_state_events_tracker.py b/synapse/storage/util/partial_state_events_tracker.py
index f8addf38f6..5078f6367b 100644
--- a/synapse/storage/util/partial_state_events_tracker.py
+++ b/synapse/storage/util/partial_state_events_tracker.py
@@ -21,7 +21,7 @@
 
 import logging
 from collections import defaultdict
-from typing import Collection, Dict, Set
+from typing import Collection
 
 from twisted.internet import defer
 from twisted.internet.defer import Deferred
@@ -43,7 +43,7 @@ class PartialStateEventsTracker:
         self._store = store
         # a map from event id to a set of Deferreds which are waiting for that event to be
         # un-partial-stated.
-        self._observers: Dict[str, Set[Deferred[None]]] = defaultdict(set)
+        self._observers: dict[str, set[Deferred[None]]] = defaultdict(set)
 
     def notify_un_partial_stated(self, event_id: str) -> None:
         """Notify that we now have full state for a given event
@@ -93,7 +93,7 @@ class PartialStateEventsTracker:
         )
 
         # create an observer for each lazy-joined event
-        observers: Dict[str, Deferred[None]] = {
+        observers: dict[str, Deferred[None]] = {
             event_id: Deferred() for event_id in partial_state_event_ids
         }
         for event_id, observer in observers.items():
@@ -140,7 +140,7 @@ class PartialCurrentStateTracker:
 
         # a map from room id to a set of Deferreds which are waiting for that room to be
         # un-partial-stated.
-        self._observers: Dict[str, Set[Deferred[None]]] = defaultdict(set)
+        self._observers: dict[str, set[Deferred[None]]] = defaultdict(set)
 
     def notify_un_partial_stated(self, room_id: str) -> None:
         """Notify that we now have full current state for a given room
diff --git a/synapse/storage/util/sequence.py b/synapse/storage/util/sequence.py
index cac3eba1a5..5bee3cf34f 100644
--- a/synapse/storage/util/sequence.py
+++ b/synapse/storage/util/sequence.py
@@ -21,7 +21,7 @@
 import abc
 import logging
 import threading
-from typing import TYPE_CHECKING, Callable, List, Optional
+from typing import TYPE_CHECKING, Callable
 
 from synapse.storage.engines import (
     BaseDatabaseEngine,
@@ -61,7 +61,7 @@ class SequenceGenerator(metaclass=abc.ABCMeta):
         ...
 
     @abc.abstractmethod
-    def get_next_mult_txn(self, txn: Cursor, n: int) -> List[int]:
+    def get_next_mult_txn(self, txn: Cursor, n: int) -> list[int]:
         """Get the next `n` IDs in the sequence"""
         ...
 
@@ -71,7 +71,7 @@ class SequenceGenerator(metaclass=abc.ABCMeta):
         db_conn: "LoggingDatabaseConnection",
         table: str,
         id_column: str,
-        stream_name: Optional[str] = None,
+        stream_name: str | None = None,
         positive: bool = True,
     ) -> None:
         """Should be called during start up to test that the current value of
@@ -105,7 +105,7 @@ class PostgresSequenceGenerator(SequenceGenerator):
         assert fetch_res is not None
         return fetch_res[0]
 
-    def get_next_mult_txn(self, txn: Cursor, n: int) -> List[int]:
+    def get_next_mult_txn(self, txn: Cursor, n: int) -> list[int]:
         txn.execute(
             "SELECT nextval(?) FROM generate_series(1, ?)", (self._sequence_name, n)
         )
@@ -116,7 +116,7 @@ class PostgresSequenceGenerator(SequenceGenerator):
         db_conn: "LoggingDatabaseConnection",
         table: str,
         id_column: str,
-        stream_name: Optional[str] = None,
+        stream_name: str | None = None,
         positive: bool = True,
     ) -> None:
         """See SequenceGenerator.check_consistency for docstring."""
@@ -223,10 +223,10 @@ class LocalSequenceGenerator(SequenceGenerator):
                  get_next_id_txn; should return the current maximum id
         """
         # the callback. this is cleared after it is called, so that it can be GCed.
-        self._callback: Optional[GetFirstCallbackType] = get_first_callback
+        self._callback: GetFirstCallbackType | None = get_first_callback
 
         # The current max value, or None if we haven't looked in the DB yet.
-        self._current_max_id: Optional[int] = None
+        self._current_max_id: int | None = None
         self._lock = threading.Lock()
 
     def get_next_id_txn(self, txn: Cursor) -> int:
@@ -241,7 +241,7 @@ class LocalSequenceGenerator(SequenceGenerator):
             self._current_max_id += 1
             return self._current_max_id
 
-    def get_next_mult_txn(self, txn: Cursor, n: int) -> List[int]:
+    def get_next_mult_txn(self, txn: Cursor, n: int) -> list[int]:
         with self._lock:
             if self._current_max_id is None:
                 assert self._callback is not None
@@ -257,7 +257,7 @@ class LocalSequenceGenerator(SequenceGenerator):
         db_conn: Connection,
         table: str,
         id_column: str,
-        stream_name: Optional[str] = None,
+        stream_name: str | None = None,
         positive: bool = True,
     ) -> None:
         # There is nothing to do for in memory sequences
@@ -278,9 +278,9 @@ def build_sequence_generator(
     database_engine: BaseDatabaseEngine,
     get_first_callback: GetFirstCallbackType,
     sequence_name: str,
-    table: Optional[str],
-    id_column: Optional[str],
-    stream_name: Optional[str] = None,
+    table: str | None,
+    id_column: str | None,
+    stream_name: str | None = None,
     positive: bool = True,
 ) -> SequenceGenerator:
     """Get the best impl of SequenceGenerator available
diff --git a/synapse/streams/__init__.py b/synapse/streams/__init__.py
index 67635d7ebe..0d386e538e 100644
--- a/synapse/streams/__init__.py
+++ b/synapse/streams/__init__.py
@@ -19,7 +19,7 @@
 #
 #
 from abc import ABC, abstractmethod
-from typing import Generic, List, Optional, Tuple, TypeVar
+from typing import Generic, TypeVar
 
 from synapse.types import StrCollection, UserID
 
@@ -38,6 +38,6 @@ class EventSource(ABC, Generic[K, R]):
         limit: int,
         room_ids: StrCollection,
         is_guest: bool,
-        explicit_room_id: Optional[str] = None,
-    ) -> Tuple[List[R], K]:
+        explicit_room_id: str | None = None,
+    ) -> tuple[list[R], K]:
         raise NotImplementedError()
diff --git a/synapse/streams/config.py b/synapse/streams/config.py
index 53751e7624..4f7f44ac65 100644
--- a/synapse/streams/config.py
+++ b/synapse/streams/config.py
@@ -19,7 +19,6 @@
 #
 #
 import logging
-from typing import Optional
 
 import attr
 
@@ -66,8 +65,8 @@ def extract_stream_token_from_pagination_token(token_str: str) -> str:
 class PaginationConfig:
     """A configuration object which stores pagination parameters."""
 
-    from_token: Optional[StreamToken]
-    to_token: Optional[StreamToken]
+    from_token: StreamToken | None
+    to_token: StreamToken | None
     direction: Direction
     limit: int
 
diff --git a/synapse/streams/events.py b/synapse/streams/events.py
index 1e4bebe46d..143f659499 100644
--- a/synapse/streams/events.py
+++ b/synapse/streams/events.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Sequence, Tuple
+from typing import TYPE_CHECKING, Sequence
 
 import attr
 
@@ -52,7 +52,7 @@ class _EventSourcesInner:
     receipt: ReceiptEventSource
     account_data: AccountDataEventSource
 
-    def get_sources(self) -> Sequence[Tuple[StreamKeyType, EventSource]]:
+    def get_sources(self) -> Sequence[tuple[StreamKeyType, EventSource]]:
         return [
             (StreamKeyType.ROOM, self.room),
             (StreamKeyType.PRESENCE, self.presence),
diff --git a/synapse/synapse_rust/acl.pyi b/synapse/synapse_rust/acl.pyi
index 985994d313..934d0de80a 100644
--- a/synapse/synapse_rust/acl.pyi
+++ b/synapse/synapse_rust/acl.pyi
@@ -13,10 +13,8 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
-from typing import List
-
 class ServerAclEvaluator:
     def __init__(
-        self, allow_ip_literals: bool, allow: List[str], deny: List[str]
+        self, allow_ip_literals: bool, allow: list[str], deny: list[str]
     ) -> None: ...
     def server_matches_acl_event(self, server_name: str) -> bool: ...
diff --git a/synapse/synapse_rust/events.pyi b/synapse/synapse_rust/events.pyi
index a82211283b..0add391c65 100644
--- a/synapse/synapse_rust/events.pyi
+++ b/synapse/synapse_rust/events.pyi
@@ -10,16 +10,16 @@
 # See the GNU Affero General Public License for more details:
 # <https://www.gnu.org/licenses/agpl-3.0.html>.
 
-from typing import List, Mapping, Optional, Tuple
+from typing import Mapping
 
 from synapse.types import JsonDict
 
 class EventInternalMetadata:
     def __init__(self, internal_metadata_dict: JsonDict): ...
 
-    stream_ordering: Optional[int]
+    stream_ordering: int | None
     """the stream ordering of this event. None, until it has been persisted."""
-    instance_name: Optional[str]
+    instance_name: str | None
     """the instance name of the server that persisted this event. None, until it has been persisted."""
 
     outlier: bool
@@ -62,7 +62,7 @@ class EventInternalMetadata:
         (Added in synapse 0.99.0, so may be unreliable for events received before that)
         """
 
-    def get_send_on_behalf_of(self) -> Optional[str]:
+    def get_send_on_behalf_of(self) -> str | None:
         """Whether this server should send the event on behalf of another server.
         This is used by the federation "send_join" API to forward the initial join
         event for a server in the room.
@@ -115,7 +115,7 @@ def event_visible_to_server(
     history_visibility: str,
     erased_senders: Mapping[str, bool],
     partial_state_invisible: bool,
-    memberships: List[Tuple[str, str]],
+    memberships: list[tuple[str, str]],
 ) -> bool:
     """Determine whether the server is allowed to see the unredacted event.
 
diff --git a/synapse/synapse_rust/http_client.pyi b/synapse/synapse_rust/http_client.pyi
index 9fb7831e6b..530d2be8e3 100644
--- a/synapse/synapse_rust/http_client.pyi
+++ b/synapse/synapse_rust/http_client.pyi
@@ -17,6 +17,10 @@ from twisted.internet.defer import Deferred
 from synapse.types import ISynapseReactor
 
 class HttpClient:
+    """
+    The returned deferreds follow Synapse logcontext rules.
+    """
+
     def __init__(self, reactor: ISynapseReactor, user_agent: str) -> None: ...
     def get(self, url: str, response_limit: int) -> Deferred[bytes]: ...
     def post(
diff --git a/synapse/synapse_rust/push.pyi b/synapse/synapse_rust/push.pyi
index a3e12ad648..9d8f0389e8 100644
--- a/synapse/synapse_rust/push.pyi
+++ b/synapse/synapse_rust/push.pyi
@@ -13,7 +13,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
-from typing import Any, Collection, Dict, Mapping, Optional, Sequence, Tuple, Union
+from typing import Any, Collection, Mapping, Sequence
 
 from synapse.types import JsonDict, JsonValue
 
@@ -25,7 +25,7 @@ class PushRule:
     @property
     def conditions(self) -> Sequence[Mapping[str, str]]: ...
     @property
-    def actions(self) -> Sequence[Union[Mapping[str, Any], str]]: ...
+    def actions(self) -> Sequence[Mapping[str, Any] | str]: ...
     @property
     def default(self) -> bool: ...
     @property
@@ -43,7 +43,7 @@ class FilteredPushRules:
     def __init__(
         self,
         push_rules: PushRules,
-        enabled_map: Dict[str, bool],
+        enabled_map: dict[str, bool],
         msc1767_enabled: bool,
         msc3381_polls_enabled: bool,
         msc3664_enabled: bool,
@@ -51,7 +51,7 @@ class FilteredPushRules:
         msc4210_enabled: bool,
         msc4306_enabled: bool,
     ): ...
-    def rules(self) -> Collection[Tuple[PushRule, bool]]: ...
+    def rules(self) -> Collection[tuple[PushRule, bool]]: ...
 
 def get_base_rule_ids() -> Collection[str]: ...
 
@@ -61,11 +61,11 @@ class PushRuleEvaluator:
         flattened_keys: Mapping[str, JsonValue],
         has_mentions: bool,
         room_member_count: int,
-        sender_power_level: Optional[int],
+        sender_power_level: int | None,
         notification_power_levels: Mapping[str, int],
         related_events_flattened: Mapping[str, Mapping[str, JsonValue]],
         related_event_match_enabled: bool,
-        room_version_feature_flags: Tuple[str, ...],
+        room_version_feature_flags: tuple[str, ...],
         msc3931_enabled: bool,
         msc4210_enabled: bool,
         msc4306_enabled: bool,
@@ -73,14 +73,14 @@ class PushRuleEvaluator:
     def run(
         self,
         push_rules: FilteredPushRules,
-        user_id: Optional[str],
-        display_name: Optional[str],
-        msc4306_thread_subscription_state: Optional[bool],
-    ) -> Collection[Union[Mapping, str]]: ...
+        user_id: str | None,
+        display_name: str | None,
+        msc4306_thread_subscription_state: bool | None,
+    ) -> Collection[Mapping | str]: ...
     def matches(
         self,
         condition: JsonDict,
-        user_id: Optional[str],
-        display_name: Optional[str],
-        msc4306_thread_subscription_state: Optional[bool] = None,
+        user_id: str | None,
+        display_name: str | None,
+        msc4306_thread_subscription_state: bool | None = None,
     ) -> bool: ...
diff --git a/synapse/synapse_rust/segmenter.pyi b/synapse/synapse_rust/segmenter.pyi
index 5f36765947..19a0a4d83c 100644
--- a/synapse/synapse_rust/segmenter.pyi
+++ b/synapse/synapse_rust/segmenter.pyi
@@ -1,3 +1 @@
-from typing import List
-
-def parse_words(text: str) -> List[str]: ...
+def parse_words(text: str) -> list[str]: ...
diff --git a/synapse/types/__init__.py b/synapse/types/__init__.py
index 0386cb77d6..16892b37c0 100644
--- a/synapse/types/__init__.py
+++ b/synapse/types/__init__.py
@@ -29,17 +29,12 @@ from typing import (
     AbstractSet,
     Any,
     ClassVar,
-    Dict,
-    List,
     Literal,
     Mapping,
     Match,
     MutableMapping,
     NoReturn,
     Optional,
-    Set,
-    Tuple,
-    Type,
     TypedDict,
     TypeVar,
     Union,
@@ -84,16 +79,16 @@ logger = logging.getLogger(__name__)
 # Define a state map type from type/state_key to T (usually an event ID or
 # event)
 T = TypeVar("T")
-StateKey = Tuple[str, str]
+StateKey = tuple[str, str]
 StateMap = Mapping[StateKey, T]
 MutableStateMap = MutableMapping[StateKey, T]
 
 # JSON types. These could be made stronger, but will do for now.
 # A "simple" (canonical) JSON value.
-SimpleJsonValue = Optional[Union[str, int, bool]]
-JsonValue = Union[List[SimpleJsonValue], Tuple[SimpleJsonValue, ...], SimpleJsonValue]
+SimpleJsonValue = str | int | bool | None
+JsonValue = list[SimpleJsonValue] | tuple[SimpleJsonValue, ...] | SimpleJsonValue
 # A JSON-serialisable dict.
-JsonDict = Dict[str, Any]
+JsonDict = dict[str, Any]
 # A JSON-serialisable mapping; roughly speaking an immutable JSONDict.
 # Useful when you have a TypedDict which isn't going to be mutated and you don't want
 # to cast to JsonDict everywhere.
@@ -106,12 +101,12 @@ JsonSerializable = object
 #
 # StrCollection is an unordered collection of strings. If ordering is important,
 # StrSequence can be used instead.
-StrCollection = Union[Tuple[str, ...], List[str], AbstractSet[str]]
+StrCollection = tuple[str, ...] | list[str] | AbstractSet[str]
 # Sequence[str] that does not include str itself; str being a Sequence[str]
 # is very misleading and results in bugs.
 #
 # Unlike StrCollection, StrSequence is an ordered collection of strings.
-StrSequence = Union[Tuple[str, ...], List[str]]
+StrSequence = tuple[str, ...] | list[str]
 
 
 # Note that this seems to require inheriting *directly* from Interface in order
@@ -163,15 +158,15 @@ class Requester:
     """
 
     user: "UserID"
-    access_token_id: Optional[int]
+    access_token_id: int | None
     is_guest: bool
-    scope: Set[str]
+    scope: set[str]
     shadow_banned: bool
-    device_id: Optional[str]
+    device_id: str | None
     app_service: Optional["ApplicationService"]
     authenticated_entity: str
 
-    def serialize(self) -> Dict[str, Any]:
+    def serialize(self) -> dict[str, Any]:
         """Converts self to a type that can be serialized as JSON, and then
         deserialized by `deserialize`
 
@@ -191,7 +186,7 @@ class Requester:
 
     @staticmethod
     def deserialize(
-        store: "ApplicationServiceWorkerStore", input: Dict[str, Any]
+        store: "ApplicationServiceWorkerStore", input: dict[str, Any]
     ) -> "Requester":
         """Converts a dict that was produced by `serialize` back into a
         Requester.
@@ -221,13 +216,13 @@ class Requester:
 
 def create_requester(
     user_id: Union[str, "UserID"],
-    access_token_id: Optional[int] = None,
+    access_token_id: int | None = None,
     is_guest: bool = False,
     scope: StrCollection = (),
     shadow_banned: bool = False,
-    device_id: Optional[str] = None,
+    device_id: str | None = None,
     app_service: Optional["ApplicationService"] = None,
-    authenticated_entity: Optional[str] = None,
+    authenticated_entity: str | None = None,
 ) -> Requester:
     """
     Create a new ``Requester`` object
@@ -305,11 +300,11 @@ class DomainSpecificString(metaclass=abc.ABCMeta):
     def __copy__(self: DS) -> DS:
         return self
 
-    def __deepcopy__(self: DS, memo: Dict[str, object]) -> DS:
+    def __deepcopy__(self: DS, memo: dict[str, object]) -> DS:
         return self
 
     @classmethod
-    def from_string(cls: Type[DS], s: str) -> DS:
+    def from_string(cls: type[DS], s: str) -> DS:
         """Parse the string given by 's' into a structure object."""
         if len(s) < 1 or s[0:1] != cls.SIGIL:
             raise SynapseError(
@@ -337,7 +332,7 @@ class DomainSpecificString(metaclass=abc.ABCMeta):
         return "%s%s:%s" % (self.SIGIL, self.localpart, self.domain)
 
     @classmethod
-    def is_valid(cls: Type[DS], s: str) -> bool:
+    def is_valid(cls: type[DS], s: str) -> bool:
         """Parses the input string and attempts to ensure it is valid."""
         # TODO: this does not reject an empty localpart or an overly-long string.
         # See https://spec.matrix.org/v1.2/appendices/#identifier-grammar
@@ -390,10 +385,10 @@ class RoomID:
 
     SIGIL = "!"
     id: str
-    room_id_with_domain: Optional[RoomIdWithDomain]
+    room_id_with_domain: RoomIdWithDomain | None
 
     @classmethod
-    def is_valid(cls: Type["RoomID"], s: str) -> bool:
+    def is_valid(cls: type["RoomID"], s: str) -> bool:
         if ":" in s:
             return RoomIdWithDomain.is_valid(s)
         try:
@@ -402,7 +397,7 @@ class RoomID:
         except Exception:
             return False
 
-    def get_domain(self) -> Optional[str]:
+    def get_domain(self) -> str | None:
         if not self.room_id_with_domain:
             return None
         return self.room_id_with_domain.domain
@@ -415,7 +410,7 @@ class RoomID:
     __repr__ = to_string
 
     @classmethod
-    def from_string(cls: Type["RoomID"], s: str) -> "RoomID":
+    def from_string(cls: type["RoomID"], s: str) -> "RoomID":
         # sigil check
         if len(s) < 1 or s[0] != cls.SIGIL:
             raise SynapseError(
@@ -424,7 +419,7 @@ class RoomID:
                 Codes.INVALID_PARAM,
             )
 
-        room_id_with_domain: Optional[RoomIdWithDomain] = None
+        room_id_with_domain: RoomIdWithDomain | None = None
         if ":" in s:
             room_id_with_domain = RoomIdWithDomain.from_string(s)
         else:
@@ -492,7 +487,7 @@ NON_MXID_CHARACTER_PATTERN = re.compile(
 
 
 def map_username_to_mxid_localpart(
-    username: Union[str, bytes], case_sensitive: bool = False
+    username: str | bytes, case_sensitive: bool = False
 ) -> str:
     """Map a username onto a string suitable for a MXID
 
@@ -749,7 +744,7 @@ class RoomStreamToken(AbstractMultiWriterStreamToken):
     attributes, must be hashable.
     """
 
-    topological: Optional[int] = attr.ib(
+    topological: int | None = attr.ib(
         validator=attr.validators.optional(attr.validators.instance_of(int)),
         kw_only=True,
         default=None,
@@ -829,7 +824,7 @@ class RoomStreamToken(AbstractMultiWriterStreamToken):
 
         return super().copy_and_advance(other)
 
-    def as_historical_tuple(self) -> Tuple[int, int]:
+    def as_historical_tuple(self) -> tuple[int, int]:
         """Returns a tuple of `(topological, stream)` for historical tokens.
 
         Raises if not an historical token (i.e. doesn't have a topological part).
@@ -959,7 +954,7 @@ class MultiWriterStreamToken(AbstractMultiWriterStreamToken):
     def is_stream_position_in_range(
         low: Optional["AbstractMultiWriterStreamToken"],
         high: Optional["AbstractMultiWriterStreamToken"],
-        instance_name: Optional[str],
+        instance_name: str | None,
         pos: int,
     ) -> bool:
         """Checks if a given persisted position is between the two given tokens.
@@ -1229,11 +1224,11 @@ class StreamToken:
     @overload
     def get_field(
         self, key: StreamKeyType
-    ) -> Union[int, RoomStreamToken, MultiWriterStreamToken]: ...
+    ) -> int | RoomStreamToken | MultiWriterStreamToken: ...
 
     def get_field(
         self, key: StreamKeyType
-    ) -> Union[int, RoomStreamToken, MultiWriterStreamToken]:
+    ) -> int | RoomStreamToken | MultiWriterStreamToken:
         """Returns the stream ID for the given key."""
         return getattr(self, key.value)
 
@@ -1399,8 +1394,8 @@ class PersistedEventPosition(PersistedPosition):
 
 @attr.s(slots=True, frozen=True, auto_attribs=True)
 class ThirdPartyInstanceID:
-    appservice_id: Optional[str]
-    network_id: Optional[str]
+    appservice_id: str | None
+    network_id: str | None
 
     # Deny iteration because it will bite you if you try to create a singleton
     # set by:
@@ -1412,7 +1407,7 @@ class ThirdPartyInstanceID:
     def __copy__(self) -> "ThirdPartyInstanceID":
         return self
 
-    def __deepcopy__(self, memo: Dict[str, object]) -> "ThirdPartyInstanceID":
+    def __deepcopy__(self, memo: dict[str, object]) -> "ThirdPartyInstanceID":
         return self
 
     @classmethod
@@ -1436,8 +1431,8 @@ class ReadReceipt:
     room_id: str
     receipt_type: str
     user_id: str
-    event_ids: List[str]
-    thread_id: Optional[str]
+    event_ids: list[str]
+    thread_id: str | None
     data: JsonDict
 
 
@@ -1459,8 +1454,8 @@ class DeviceListUpdates:
     # The latter happening only once, thus always giving you the same sets
     # across multiple DeviceListUpdates instances.
     # Also see: don't define mutable default arguments.
-    changed: Set[str] = attr.ib(factory=set)
-    left: Set[str] = attr.ib(factory=set)
+    changed: set[str] = attr.ib(factory=set)
+    left: set[str] = attr.ib(factory=set)
 
     def __bool__(self) -> bool:
         return bool(self.changed or self.left)
@@ -1468,7 +1463,7 @@ class DeviceListUpdates:
 
 def get_verify_key_from_cross_signing_key(
     key_info: Mapping[str, Any],
-) -> Tuple[str, VerifyKey]:
+) -> tuple[str, VerifyKey]:
     """Get the key ID and signedjson verify key from a cross-signing key dict
 
     Args:
@@ -1512,11 +1507,11 @@ class UserInfo:
     """
 
     user_id: UserID
-    appservice_id: Optional[int]
-    consent_server_notice_sent: Optional[str]
-    consent_version: Optional[str]
-    consent_ts: Optional[int]
-    user_type: Optional[str]
+    appservice_id: int | None
+    consent_server_notice_sent: str | None
+    consent_version: str | None
+    consent_ts: int | None
+    user_type: str | None
     creation_ts: int
     is_admin: bool
     is_deactivated: bool
@@ -1529,14 +1524,14 @@ class UserInfo:
 
 class UserProfile(TypedDict):
     user_id: str
-    display_name: Optional[str]
-    avatar_url: Optional[str]
+    display_name: str | None
+    avatar_url: str | None
 
 
 @attr.s(auto_attribs=True, frozen=True, slots=True)
 class RetentionPolicy:
-    min_lifetime: Optional[int] = None
-    max_lifetime: Optional[int] = None
+    min_lifetime: int | None = None
+    max_lifetime: int | None = None
 
 
 class TaskStatus(str, Enum):
@@ -1568,13 +1563,13 @@ class ScheduledTask:
     # In milliseconds since epoch in system time timezone, usually UTC.
     timestamp: int
     # Optionally bind a task to some resource id for easy retrieval
-    resource_id: Optional[str]
+    resource_id: str | None
     # Optional parameters that will be passed to the function ran by the task
-    params: Optional[JsonMapping]
+    params: JsonMapping | None
     # Optional result that can be updated by the running task
-    result: Optional[JsonMapping]
+    result: JsonMapping | None
     # Optional error that should be assigned a value when the status is FAILED
-    error: Optional[str]
+    error: str | None
 
 
 @attr.s(auto_attribs=True, frozen=True, slots=True)
diff --git a/synapse/types/handlers/__init__.py b/synapse/types/handlers/__init__.py
index f2fbc1dddf..b9d1b41a75 100644
--- a/synapse/types/handlers/__init__.py
+++ b/synapse/types/handlers/__init__.py
@@ -19,7 +19,7 @@
 #
 
 
-from typing import List, Optional, TypedDict
+from typing import TypedDict
 
 from synapse.api.constants import EventTypes
 
@@ -66,10 +66,10 @@ class ShutdownRoomParams(TypedDict):
             even if there are still users joined to the room.
     """
 
-    requester_user_id: Optional[str]
-    new_room_user_id: Optional[str]
-    new_room_name: Optional[str]
-    message: Optional[str]
+    requester_user_id: str | None
+    new_room_user_id: str | None
+    new_room_name: str | None
+    message: str | None
     block: bool
     purge: bool
     force_purge: bool
@@ -87,7 +87,7 @@ class ShutdownRoomResponse(TypedDict):
         new_room_id: A string representing the room ID of the new room.
     """
 
-    kicked_users: List[str]
-    failed_to_kick_users: List[str]
-    local_aliases: List[str]
-    new_room_id: Optional[str]
+    kicked_users: list[str]
+    failed_to_kick_users: list[str]
+    local_aliases: list[str]
+    new_room_id: str | None
diff --git a/synapse/types/handlers/sliding_sync.py b/synapse/types/handlers/sliding_sync.py
index 3a7a50066d..a5d90252b7 100644
--- a/synapse/types/handlers/sliding_sync.py
+++ b/synapse/types/handlers/sliding_sync.py
@@ -21,23 +21,18 @@ from typing import (
     AbstractSet,
     Any,
     Callable,
-    Dict,
     Final,
     Generic,
-    List,
     Mapping,
     MutableMapping,
-    Optional,
     Sequence,
-    Set,
-    Tuple,
     TypeVar,
     cast,
 )
 
 import attr
+from pydantic import ConfigDict
 
-from synapse._pydantic_compat import Extra
 from synapse.api.constants import EventTypes
 from synapse.events import EventBase
 
@@ -72,15 +67,12 @@ class SlidingSyncConfig(SlidingSyncBody):
 
     user: UserID
     requester: Requester
-
-    # Pydantic config
-    class Config:
-        # By default, ignore fields that we don't recognise.
-        extra = Extra.ignore
-        # By default, don't allow fields to be reassigned after parsing.
-        allow_mutation = False
-        # Allow custom types like `UserID` to be used in the model
-        arbitrary_types_allowed = True
+    model_config = ConfigDict(
+        extra="ignore",
+        frozen=True,
+        # Allow custom types like `UserID` to be used in the model.
+        arbitrary_types_allowed=True,
+    )
 
 
 class OperationType(Enum):
@@ -176,31 +168,31 @@ class SlidingSyncResult:
         @attr.s(slots=True, frozen=True, auto_attribs=True)
         class StrippedHero:
             user_id: str
-            display_name: Optional[str]
-            avatar_url: Optional[str]
+            display_name: str | None
+            avatar_url: str | None
 
-        name: Optional[str]
-        avatar: Optional[str]
-        heroes: Optional[List[StrippedHero]]
+        name: str | None
+        avatar: str | None
+        heroes: list[StrippedHero] | None
         is_dm: bool
         initial: bool
         unstable_expanded_timeline: bool
         # Should be empty for invite/knock rooms with `stripped_state`
-        required_state: List[EventBase]
+        required_state: list[EventBase]
         # Should be empty for invite/knock rooms with `stripped_state`
-        timeline_events: List[EventBase]
-        bundled_aggregations: Optional[Dict[str, "BundledAggregations"]]
+        timeline_events: list[EventBase]
+        bundled_aggregations: dict[str, "BundledAggregations"] | None
         # Optional because it's only relevant to invite/knock rooms
-        stripped_state: List[JsonDict]
+        stripped_state: list[JsonDict]
         # Only optional because it won't be included for invite/knock rooms with `stripped_state`
-        prev_batch: Optional[StreamToken]
+        prev_batch: StreamToken | None
         # Only optional because it won't be included for invite/knock rooms with `stripped_state`
-        limited: Optional[bool]
+        limited: bool | None
         # Only optional because it won't be included for invite/knock rooms with `stripped_state`
-        num_live: Optional[int]
-        bump_stamp: Optional[int]
-        joined_count: Optional[int]
-        invited_count: Optional[int]
+        num_live: int | None
+        bump_stamp: int | None
+        joined_count: int | None
+        invited_count: int | None
         notification_count: int
         highlight_count: int
 
@@ -243,11 +235,11 @@ class SlidingSyncResult:
             """
 
             op: OperationType
-            range: Tuple[int, int]
-            room_ids: List[str]
+            range: tuple[int, int]
+            room_ids: list[str]
 
         count: int
-        ops: List[Operation]
+        ops: list[Operation]
 
     @attr.s(slots=True, frozen=True, auto_attribs=True)
     class Extensions:
@@ -291,7 +283,7 @@ class SlidingSyncResult:
             """
 
             # Only present on incremental syncs
-            device_list_updates: Optional[DeviceListUpdates]
+            device_list_updates: DeviceListUpdates | None
             device_one_time_keys_count: Mapping[str, int]
             device_unused_fallback_key_types: Sequence[str]
 
@@ -374,7 +366,7 @@ class SlidingSyncResult:
             @attr.s(slots=True, frozen=True, auto_attribs=True)
             class ThreadSubscription:
                 # always present when `subscribed`
-                automatic: Optional[bool]
+                automatic: bool | None
 
                 # the same as our stream_id; useful for clients to resolve
                 # race conditions locally
@@ -387,10 +379,10 @@ class SlidingSyncResult:
                 bump_stamp: int
 
             # room_id -> event_id (of thread root) -> the subscription change
-            subscribed: Optional[Mapping[str, Mapping[str, ThreadSubscription]]]
+            subscribed: Mapping[str, Mapping[str, ThreadSubscription]] | None
             # room_id -> event_id (of thread root) -> the unsubscription
-            unsubscribed: Optional[Mapping[str, Mapping[str, ThreadUnsubscription]]]
-            prev_batch: Optional[ThreadSubscriptionsToken]
+            unsubscribed: Mapping[str, Mapping[str, ThreadUnsubscription]] | None
+            prev_batch: ThreadSubscriptionsToken | None
 
             def __bool__(self) -> bool:
                 return (
@@ -433,26 +425,26 @@ class SlidingSyncResult:
                         unsigned.m.relations.m.thread). Only present if thread_root is included.
                 """
 
-                thread_root: Optional[EventBase]
-                prev_batch: Optional[StreamToken]
-                bundled_aggregations: Optional["BundledAggregations"] = None
+                thread_root: EventBase | None
+                prev_batch: StreamToken | None
+                bundled_aggregations: "BundledAggregations | None" = None
 
                 def __bool__(self) -> bool:
                     return bool(self.thread_root) or bool(self.prev_batch)
 
-            updates: Optional[Mapping[str, Mapping[str, ThreadUpdate]]]
-            prev_batch: Optional[StreamToken]
+            updates: Mapping[str, Mapping[str, ThreadUpdate]] | None
+            prev_batch: StreamToken | None
 
             def __bool__(self) -> bool:
                 return bool(self.updates) or bool(self.prev_batch)
 
-        to_device: Optional[ToDeviceExtension] = None
-        e2ee: Optional[E2eeExtension] = None
-        account_data: Optional[AccountDataExtension] = None
-        receipts: Optional[ReceiptsExtension] = None
-        typing: Optional[TypingExtension] = None
-        thread_subscriptions: Optional[ThreadSubscriptionsExtension] = None
-        threads: Optional[ThreadsExtension] = None
+        to_device: ToDeviceExtension | None = None
+        e2ee: E2eeExtension | None = None
+        account_data: AccountDataExtension | None = None
+        receipts: ReceiptsExtension | None = None
+        typing: TypingExtension | None = None
+        thread_subscriptions: ThreadSubscriptionsExtension | None = None
+        threads: ThreadsExtension | None = None
 
         def __bool__(self) -> bool:
             return bool(
@@ -467,7 +459,7 @@ class SlidingSyncResult:
 
     next_pos: SlidingSyncStreamToken
     lists: Mapping[str, SlidingWindowList]
-    rooms: Dict[str, RoomResult]
+    rooms: dict[str, RoomResult]
     extensions: Extensions
 
     def __bool__(self) -> bool:
@@ -537,7 +529,7 @@ class RoomSyncConfig:
         Args:
             room_params: `SlidingSyncConfig.SlidingSyncList` or `SlidingSyncConfig.RoomSubscription`
         """
-        required_state_map: Dict[str, Set[str]] = {}
+        required_state_map: dict[str, set[str]] = {}
         for (
             state_type,
             state_key,
@@ -789,7 +781,7 @@ class HaveSentRoom(Generic[T]):
     """
 
     status: HaveSentRoomFlag
-    last_token: Optional[T]
+    last_token: T | None
 
     @staticmethod
     def live() -> "HaveSentRoom[T]":
diff --git a/synapse/types/rest/client/__init__.py b/synapse/types/rest/client/__init__.py
index 3e98fb3def..e10cca7d9b 100644
--- a/synapse/types/rest/client/__init__.py
+++ b/synapse/types/rest/client/__init__.py
@@ -18,18 +18,19 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import TYPE_CHECKING, Dict, List, Optional, Tuple, Union
-
-from synapse._pydantic_compat import (
-    Extra,
+from pydantic import (
+    ConfigDict,
     Field,
     StrictBool,
     StrictInt,
     StrictStr,
-    conint,
-    constr,
-    validator,
+    StringConstraints,
+    field_validator,
+    model_validator,
 )
+from pydantic_core import PydanticCustomError
+from typing_extensions import Annotated, Self
+
 from synapse.types.rest import RequestBodyModel
 from synapse.util.threepids import validate_email
 
@@ -44,39 +45,36 @@ class AuthenticationData(RequestBodyModel):
     `.dict(exclude_unset=True)` to access them.
     """
 
-    class Config:
-        extra = Extra.allow
+    model_config = ConfigDict(extra="allow")
 
-    session: Optional[StrictStr] = None
-    type: Optional[StrictStr] = None
+    session: StrictStr | None = None
+    type: StrictStr | None = None
 
 
-if TYPE_CHECKING:
-    ClientSecretStr = StrictStr
-else:
-    # See also assert_valid_client_secret()
-    ClientSecretStr = constr(
-        regex="[0-9a-zA-Z.=_-]",  # noqa: F722
+# See also assert_valid_client_secret()
+ClientSecretStr = Annotated[
+    str,
+    StringConstraints(
+        pattern="[0-9a-zA-Z.=_-]",
         min_length=1,
         max_length=255,
         strict=True,
-    )
+    ),
+]
 
 
 class ThreepidRequestTokenBody(RequestBodyModel):
     client_secret: ClientSecretStr
-    id_server: Optional[StrictStr]
-    id_access_token: Optional[StrictStr]
-    next_link: Optional[StrictStr]
+    id_server: StrictStr | None = None
+    id_access_token: StrictStr | None = None
+    next_link: StrictStr | None = None
     send_attempt: StrictInt
 
-    @validator("id_access_token", always=True)
-    def token_required_for_identity_server(
-        cls, token: Optional[str], values: Dict[str, object]
-    ) -> Optional[str]:
-        if values.get("id_server") is not None and token is None:
+    @model_validator(mode="after")
+    def token_required_for_identity_server(self) -> Self:
+        if self.id_server is not None and self.id_access_token is None:
             raise ValueError("id_access_token is required if an id_server is supplied.")
-        return token
+        return self
 
 
 class EmailRequestTokenBody(ThreepidRequestTokenBody):
@@ -87,14 +85,21 @@ class EmailRequestTokenBody(ThreepidRequestTokenBody):
     # know the exact spelling (eg. upper and lower case) of address in the database.
     # Without this, an email stored in the database as "foo@bar.com" would cause
     # user requests for "FOO@bar.com" to raise a Not Found error.
-    _email_validator = validator("email", allow_reuse=True)(validate_email)
+    @field_validator("email")
+    @classmethod
+    def _email_validator(cls, email: StrictStr) -> StrictStr:
+        try:
+            return validate_email(email)
+        except ValueError as e:
+            # To ensure backward compatibility of HTTP error codes, we return a
+            # Pydantic error with the custom, unrecognized error type
+            # "email_custom_err_type" instead of the default error type
+            # "value_error". This results in the more generic BAD_JSON HTTP
+            # error instead of the more specific INVALID_PARAM one.
+            raise PydanticCustomError("email_custom_err_type", str(e), None) from e
 
 
-if TYPE_CHECKING:
-    ISO3116_1_Alpha_2 = StrictStr
-else:
-    # Per spec: two-letter uppercase ISO-3166-1-alpha-2
-    ISO3116_1_Alpha_2 = constr(regex="[A-Z]{2}", strict=True)
+ISO3116_1_Alpha_2 = Annotated[str, StringConstraints(pattern="[A-Z]{2}", strict=True)]
 
 
 class MsisdnRequestTokenBody(ThreepidRequestTokenBody):
@@ -144,12 +149,10 @@ class SlidingSyncBody(RequestBodyModel):
                 (Max 1000 messages)
         """
 
-        required_state: List[Tuple[StrictStr, StrictStr]]
-        # mypy workaround via https://github.com/pydantic/pydantic/issues/156#issuecomment-1130883884
-        if TYPE_CHECKING:
-            timeline_limit: int
-        else:
-            timeline_limit: conint(le=1000, strict=True)  # type: ignore[valid-type]
+        required_state: list[
+            Annotated[tuple[StrictStr, StrictStr], Field(strict=False)]
+        ]
+        timeline_limit: Annotated[int, Field(le=1000, strict=True)]
 
     class SlidingSyncList(CommonRoomParameters):
         """
@@ -241,25 +244,30 @@ class SlidingSyncBody(RequestBodyModel):
                     list of favourite rooms again.
             """
 
-            is_dm: Optional[StrictBool] = None
-            spaces: Optional[List[StrictStr]] = None
-            is_encrypted: Optional[StrictBool] = None
-            is_invite: Optional[StrictBool] = None
-            room_types: Optional[List[Union[StrictStr, None]]] = None
-            not_room_types: Optional[List[Union[StrictStr, None]]] = None
-            room_name_like: Optional[StrictStr] = None
-            tags: Optional[List[StrictStr]] = None
-            not_tags: Optional[List[StrictStr]] = None
+            is_dm: StrictBool | None = None
+            spaces: list[StrictStr] | None = None
+            is_encrypted: StrictBool | None = None
+            is_invite: StrictBool | None = None
+            room_types: list[StrictStr | None] | None = None
+            not_room_types: list[StrictStr | None] | None = None
+            room_name_like: StrictStr | None = None
+            tags: list[StrictStr] | None = None
+            not_tags: list[StrictStr] | None = None
 
-        # mypy workaround via https://github.com/pydantic/pydantic/issues/156#issuecomment-1130883884
-        if TYPE_CHECKING:
-            ranges: Optional[List[Tuple[int, int]]] = None
-        else:
-            ranges: Optional[
-                List[Tuple[conint(ge=0, strict=True), conint(ge=0, strict=True)]]
-            ] = None  # type: ignore[valid-type]
-        slow_get_all_rooms: Optional[StrictBool] = False
-        filters: Optional[Filters] = None
+        ranges: (
+            list[
+                Annotated[
+                    tuple[
+                        Annotated[int, Field(ge=0, strict=True)],
+                        Annotated[int, Field(ge=0, strict=True)],
+                    ],
+                    Field(strict=False),
+                ]
+            ]
+            | None
+        ) = None
+        slow_get_all_rooms: StrictBool | None = False
+        filters: Filters | None = None
 
     class RoomSubscription(CommonRoomParameters):
         pass
@@ -282,14 +290,13 @@ class SlidingSyncBody(RequestBodyModel):
                 since: The `next_batch` from the previous sync response
             """
 
-            enabled: Optional[StrictBool] = False
+            enabled: StrictBool | None = False
             limit: StrictInt = 100
-            since: Optional[StrictStr] = None
+            since: StrictStr | None = None
 
-            @validator("since")
-            def since_token_check(
-                cls, value: Optional[StrictStr]
-            ) -> Optional[StrictStr]:
+            @field_validator("since")
+            @classmethod
+            def since_token_check(cls, value: StrictStr | None) -> StrictStr | None:
                 # `since` comes in as an opaque string token but we know that it's just
                 # an integer representing the position in the device inbox stream. We
                 # want to pre-validate it to make sure it works fine in downstream code.
@@ -312,7 +319,7 @@ class SlidingSyncBody(RequestBodyModel):
                 enabled
             """
 
-            enabled: Optional[StrictBool] = False
+            enabled: StrictBool | None = False
 
         class AccountDataExtension(RequestBodyModel):
             """The Account Data extension (MSC3959)
@@ -325,11 +332,11 @@ class SlidingSyncBody(RequestBodyModel):
                     extension to.
             """
 
-            enabled: Optional[StrictBool] = False
+            enabled: StrictBool | None = False
             # Process all lists defined in the Sliding Window API. (This is the default.)
-            lists: Optional[List[StrictStr]] = ["*"]
+            lists: list[StrictStr] | None = ["*"]
             # Process all room subscriptions defined in the Room Subscription API. (This is the default.)
-            rooms: Optional[List[StrictStr]] = ["*"]
+            rooms: list[StrictStr] | None = ["*"]
 
         class ReceiptsExtension(RequestBodyModel):
             """The Receipts extension (MSC3960)
@@ -342,11 +349,11 @@ class SlidingSyncBody(RequestBodyModel):
                     extension to.
             """
 
-            enabled: Optional[StrictBool] = False
+            enabled: StrictBool | None = False
             # Process all lists defined in the Sliding Window API. (This is the default.)
-            lists: Optional[List[StrictStr]] = ["*"]
+            lists: list[StrictStr] | None = ["*"]
             # Process all room subscriptions defined in the Room Subscription API. (This is the default.)
-            rooms: Optional[List[StrictStr]] = ["*"]
+            rooms: list[StrictStr] | None = ["*"]
 
         class TypingExtension(RequestBodyModel):
             """The Typing Notification extension (MSC3961)
@@ -359,11 +366,11 @@ class SlidingSyncBody(RequestBodyModel):
                     extension to.
             """
 
-            enabled: Optional[StrictBool] = False
+            enabled: StrictBool | None = False
             # Process all lists defined in the Sliding Window API. (This is the default.)
-            lists: Optional[List[StrictStr]] = ["*"]
+            lists: list[StrictStr] | None = ["*"]
             # Process all room subscriptions defined in the Room Subscription API. (This is the default.)
-            rooms: Optional[List[StrictStr]] = ["*"]
+            rooms: list[StrictStr] | None = ["*"]
 
         class ThreadSubscriptionsExtension(RequestBodyModel):
             """The Thread Subscriptions extension (MSC4308)
@@ -373,7 +380,7 @@ class SlidingSyncBody(RequestBodyModel):
                 limit: maximum number of subscription changes to return (default 100)
             """
 
-            enabled: Optional[StrictBool] = False
+            enabled: StrictBool | None = False
             limit: StrictInt = 100
 
         class ThreadsExtension(RequestBodyModel):
@@ -385,36 +392,55 @@ class SlidingSyncBody(RequestBodyModel):
                 limit: maximum number of thread updates to return across all joined rooms.
             """
 
-            enabled: Optional[StrictBool] = False
+            enabled: StrictBool | None = False
             include_roots: StrictBool = False
             limit: StrictInt = 100
 
-        to_device: Optional[ToDeviceExtension] = None
-        e2ee: Optional[E2eeExtension] = None
-        account_data: Optional[AccountDataExtension] = None
-        receipts: Optional[ReceiptsExtension] = None
-        typing: Optional[TypingExtension] = None
-        thread_subscriptions: Optional[ThreadSubscriptionsExtension] = Field(
-            alias="io.element.msc4308.thread_subscriptions"
+        to_device: ToDeviceExtension | None = None
+        e2ee: E2eeExtension | None = None
+        account_data: AccountDataExtension | None = None
+        receipts: ReceiptsExtension | None = None
+        typing: TypingExtension | None = None
+        thread_subscriptions: ThreadSubscriptionsExtension | None = Field(
+            None, alias="io.element.msc4308.thread_subscriptions"
         )
-        threads: Optional[ThreadsExtension] = Field(alias="io.element.msc4360.threads")
-
-    conn_id: Optional[StrictStr]
-
-    # mypy workaround via https://github.com/pydantic/pydantic/issues/156#issuecomment-1130883884
-    if TYPE_CHECKING:
-        lists: Optional[Dict[str, SlidingSyncList]] = None
-    else:
-        lists: Optional[Dict[constr(max_length=64, strict=True), SlidingSyncList]] = (
-            None  # type: ignore[valid-type]
+        threads: ThreadsExtension | None = Field(
+            None, alias="io.element.msc4360.threads"
         )
-    room_subscriptions: Optional[Dict[StrictStr, RoomSubscription]] = None
-    extensions: Optional[Extensions] = None
 
-    @validator("lists")
+    conn_id: StrictStr | None = None
+    lists: (
+        dict[
+            Annotated[str, StringConstraints(max_length=64, strict=True)],
+            SlidingSyncList,
+        ]
+        | None
+    ) = None
+    room_subscriptions: dict[StrictStr, RoomSubscription] | None = None
+    extensions: Extensions | None = None
+
+    @field_validator("lists")
+    @classmethod
     def lists_length_check(
-        cls, value: Optional[Dict[str, SlidingSyncList]]
-    ) -> Optional[Dict[str, SlidingSyncList]]:
+        cls, value: dict[str, SlidingSyncList] | None
+    ) -> dict[str, SlidingSyncList] | None:
         if value is not None:
             assert len(value) <= 100, f"Max lists: 100 but saw {len(value)}"
         return value
+
+
+class ThreadUpdatesBody(RequestBodyModel):
+    """
+    Thread updates companion endpoint request body (MSC4360).
+
+    Allows filtering thread updates using the same filter criteria as sliding sync lists.
+    This enables clients to paginate thread updates using the same room filters that
+    were applied when generating the prev_batch token.
+
+    Attributes:
+        filters: Optional room filters to apply, using the same structure as
+            SlidingSyncList.Filters. If not provided, thread updates from all
+            joined rooms are returned.
+    """
+
+    filters: SlidingSyncBody.SlidingSyncList.Filters | None = None
diff --git a/synapse/types/state.py b/synapse/types/state.py
index 6420e050a5..ab619a7fb8 100644
--- a/synapse/types/state.py
+++ b/synapse/types/state.py
@@ -25,13 +25,8 @@ from typing import (
     Any,
     Callable,
     Collection,
-    Dict,
     Iterable,
-    List,
     Mapping,
-    Optional,
-    Set,
-    Tuple,
     TypeVar,
 )
 
@@ -42,7 +37,7 @@ from synapse.api.constants import EventTypes
 from synapse.types import MutableStateMap, StateKey, StateMap
 
 if TYPE_CHECKING:
-    from typing import FrozenSet  # noqa: used within quoted type hint; flake8 sad
+    pass  # noqa: used within quoted type hint; flake8 sad
 
 
 logger = logging.getLogger(__name__)
@@ -64,7 +59,7 @@ class StateFilter:
             appear in `types`.
     """
 
-    types: "immutabledict[str, Optional[FrozenSet[str]]]"
+    types: "immutabledict[str, frozenset[str] | None]"
     include_others: bool = False
 
     def __attrs_post_init__(self) -> None:
@@ -105,7 +100,7 @@ class StateFilter:
         return _NONE_STATE_FILTER
 
     @staticmethod
-    def from_types(types: Iterable[Tuple[str, Optional[str]]]) -> "StateFilter":
+    def from_types(types: Iterable[tuple[str, str | None]]) -> "StateFilter":
         """Creates a filter that only fetches the given types
 
         Args:
@@ -115,7 +110,7 @@ class StateFilter:
         Returns:
             The new state filter.
         """
-        type_dict: Dict[str, Optional[Set[str]]] = {}
+        type_dict: dict[str, set[str] | None] = {}
         for typ, s in types:
             if typ in type_dict:
                 if type_dict[typ] is None:
@@ -134,7 +129,7 @@ class StateFilter:
             )
         )
 
-    def to_types(self) -> Iterable[Tuple[str, Optional[str]]]:
+    def to_types(self) -> Iterable[tuple[str, str | None]]:
         """The inverse to `from_types`."""
         for event_type, state_keys in self.types.items():
             if state_keys is None:
@@ -161,13 +156,13 @@ class StateFilter:
 
     @staticmethod
     def freeze(
-        types: Mapping[str, Optional[Collection[str]]], include_others: bool
+        types: Mapping[str, Collection[str] | None], include_others: bool
     ) -> "StateFilter":
         """
         Returns a (frozen) StateFilter with the same contents as the parameters
         specified here, which can be made of mutable types.
         """
-        types_with_frozen_values: Dict[str, Optional[FrozenSet[str]]] = {}
+        types_with_frozen_values: dict[str, frozenset[str] | None] = {}
         for state_types, state_keys in types.items():
             if state_keys is not None:
                 types_with_frozen_values[state_types] = frozenset(state_keys)
@@ -240,7 +235,7 @@ class StateFilter:
             # We want to return all non-members
             return _ALL_NON_MEMBER_STATE_FILTER
 
-    def make_sql_filter_clause(self) -> Tuple[str, List[str]]:
+    def make_sql_filter_clause(self) -> tuple[str, list[str]]:
         """Converts the filter to an SQL clause.
 
         For example:
@@ -257,7 +252,7 @@ class StateFilter:
         """
 
         where_clause = ""
-        where_args: List[str] = []
+        where_args: list[str] = []
 
         if self.is_full():
             return where_clause, where_args
@@ -293,7 +288,7 @@ class StateFilter:
 
         return where_clause, where_args
 
-    def max_entries_returned(self) -> Optional[int]:
+    def max_entries_returned(self) -> int | None:
         """Returns the maximum number of entries this filter will return if
         known, otherwise returns None.
 
@@ -353,7 +348,7 @@ class StateFilter:
             state_keys is None for state_keys in self.types.values()
         )
 
-    def concrete_types(self) -> List[Tuple[str, str]]:
+    def concrete_types(self) -> list[tuple[str, str]]:
         """Returns a list of concrete type/state_keys (i.e. not None) that
         will be fetched. This will be a complete list if `has_wildcards`
         returns False, but otherwise will be a subset (or even empty).
@@ -368,7 +363,7 @@ class StateFilter:
             for s in state_keys
         ]
 
-    def wildcard_types(self) -> List[str]:
+    def wildcard_types(self) -> list[str]:
         """Returns a list of event types which require us to fetch all state keys.
         This will be empty unless `has_wildcards` returns True.
 
@@ -377,7 +372,7 @@ class StateFilter:
         """
         return [t for t, state_keys in self.types.items() if state_keys is None]
 
-    def get_member_split(self) -> Tuple["StateFilter", "StateFilter"]:
+    def get_member_split(self) -> tuple["StateFilter", "StateFilter"]:
         """Return the filter split into two: one which assumes it's exclusively
         matching against member state, and one which assumes it's matching
         against non member state.
@@ -416,7 +411,7 @@ class StateFilter:
 
     def _decompose_into_four_parts(
         self,
-    ) -> Tuple[Tuple[bool, Set[str]], Tuple[Set[str], Set[StateKey]]]:
+    ) -> tuple[tuple[bool, set[str]], tuple[set[str], set[StateKey]]]:
         """
         Decomposes this state filter into 4 constituent parts, which can be
         thought of as this:
@@ -432,18 +427,18 @@ class StateFilter:
         correspondence.
         """
         is_all = self.include_others
-        excluded_types: Set[str] = {t for t in self.types if is_all}
-        wildcard_types: Set[str] = {t for t, s in self.types.items() if s is None}
-        concrete_keys: Set[StateKey] = set(self.concrete_types())
+        excluded_types: set[str] = {t for t in self.types if is_all}
+        wildcard_types: set[str] = {t for t, s in self.types.items() if s is None}
+        concrete_keys: set[StateKey] = set(self.concrete_types())
 
         return (is_all, excluded_types), (wildcard_types, concrete_keys)
 
     @staticmethod
     def _recompose_from_four_parts(
         all_part: bool,
-        minus_wildcards: Set[str],
-        plus_wildcards: Set[str],
-        plus_state_keys: Set[StateKey],
+        minus_wildcards: set[str],
+        plus_wildcards: set[str],
+        plus_state_keys: set[StateKey],
     ) -> "StateFilter":
         """
         Recomposes a state filter from 4 parts.
@@ -454,7 +449,7 @@ class StateFilter:
 
         # {state type -> set of state keys OR None for wildcard}
         # (The same structure as that of a StateFilter.)
-        new_types: Dict[str, Optional[Set[str]]] = {}
+        new_types: dict[str, set[str] | None] = {}
 
         # if we start with all, insert the excluded statetypes as empty sets
         # to prevent them from being included
diff --git a/synapse/util/__init__.py b/synapse/util/__init__.py
index 2ae2e245a9..f937080f9e 100644
--- a/synapse/util/__init__.py
+++ b/synapse/util/__init__.py
@@ -23,12 +23,9 @@ import collections.abc
 import logging
 import typing
 from typing import (
-    Dict,
     Iterator,
     Mapping,
-    Optional,
     Sequence,
-    Set,
     TypeVar,
 )
 
@@ -63,7 +60,7 @@ def unwrapFirstError(failure: Failure) -> Failure:
 
 def log_failure(
     failure: Failure, msg: str, consumeErrors: bool = True
-) -> Optional[Failure]:
+) -> Failure | None:
     """Creates a function suitable for passing to `Deferred.addErrback` that
     logs any failures that occur.
 
@@ -119,8 +116,8 @@ class MutableOverlayMapping(collections.abc.MutableMapping[K, V]):
     """
 
     _underlying_map: Mapping[K, V]
-    _mutable_map: Dict[K, V] = attr.ib(factory=dict)
-    _deletions: Set[K] = attr.ib(factory=set)
+    _mutable_map: dict[K, V] = attr.ib(factory=dict)
+    _deletions: set[K] = attr.ib(factory=set)
 
     def __getitem__(self, key: K) -> V:
         if key in self._deletions:
diff --git a/synapse/util/async_helpers.py b/synapse/util/async_helpers.py
index 5c828420a2..678ed103be 100644
--- a/synapse/util/async_helpers.py
+++ b/synapse/util/async_helpers.py
@@ -35,18 +35,12 @@ from typing import (
     Callable,
     Collection,
     Coroutine,
-    Dict,
     Generator,
     Generic,
     Hashable,
     Iterable,
-    List,
     Literal,
-    Optional,
-    Set,
-    Tuple,
     TypeVar,
-    Union,
     overload,
 )
 
@@ -55,7 +49,6 @@ from typing_extensions import Concatenate, ParamSpec, Unpack
 
 from twisted.internet import defer
 from twisted.internet.defer import CancelledError
-from twisted.internet.interfaces import IReactorTime
 from twisted.python.failure import Failure
 
 from synapse.logging.context import (
@@ -109,8 +102,8 @@ class ObservableDeferred(Generic[_T], AbstractObservableDeferred[_T]):
     __slots__ = ["_deferred", "_observers", "_result"]
 
     _deferred: "defer.Deferred[_T]"
-    _observers: Union[List["defer.Deferred[_T]"], Tuple[()]]
-    _result: Union[None, Tuple[Literal[True], _T], Tuple[Literal[False], Failure]]
+    _observers: list["defer.Deferred[_T]"] | tuple[()]
+    _result: None | tuple[Literal[True], _T] | tuple[Literal[False], Failure]
 
     def __init__(self, deferred: "defer.Deferred[_T]", consumeErrors: bool = False):
         object.__setattr__(self, "_deferred", deferred)
@@ -137,7 +130,7 @@ class ObservableDeferred(Generic[_T], AbstractObservableDeferred[_T]):
                     )
             return r
 
-        def errback(f: Failure) -> Optional[Failure]:
+        def errback(f: Failure) -> Failure | None:
             object.__setattr__(self, "_result", (False, f))
 
             # once we have set _result, no more entries will be added to _observers,
@@ -192,7 +185,7 @@ class ObservableDeferred(Generic[_T], AbstractObservableDeferred[_T]):
     def has_succeeded(self) -> bool:
         return self._result is not None and self._result[0] is True
 
-    def get_result(self) -> Union[_T, Failure]:
+    def get_result(self) -> _T | Failure:
         if self._result is None:
             raise ValueError(f"{self!r} has no result yet")
         return self._result[1]
@@ -269,7 +262,7 @@ async def yieldable_gather_results(
     iter: Iterable[T],
     *args: P.args,
     **kwargs: P.kwargs,
-) -> List[R]:
+) -> list[R]:
     """Executes the function with each argument concurrently.
 
     Args:
@@ -311,7 +304,7 @@ async def yieldable_gather_results_delaying_cancellation(
     iter: Iterable[T],
     *args: P.args,
     **kwargs: P.kwargs,
-) -> List[R]:
+) -> list[R]:
     """Executes the function with each argument concurrently.
     Cancellation is delayed until after all the results have been gathered.
 
@@ -352,49 +345,49 @@ T7 = TypeVar("T7")
 
 @overload
 def gather_results(
-    deferredList: Tuple[()], consumeErrors: bool = ...
-) -> "defer.Deferred[Tuple[()]]": ...
+    deferredList: tuple[()], consumeErrors: bool = ...
+) -> "defer.Deferred[tuple[()]]": ...
 
 
 @overload
 def gather_results(
-    deferredList: Tuple["defer.Deferred[T1]"],
+    deferredList: tuple["defer.Deferred[T1]"],
     consumeErrors: bool = ...,
-) -> "defer.Deferred[Tuple[T1]]": ...
+) -> "defer.Deferred[tuple[T1]]": ...
 
 
 @overload
 def gather_results(
-    deferredList: Tuple["defer.Deferred[T1]", "defer.Deferred[T2]"],
+    deferredList: tuple["defer.Deferred[T1]", "defer.Deferred[T2]"],
     consumeErrors: bool = ...,
-) -> "defer.Deferred[Tuple[T1, T2]]": ...
+) -> "defer.Deferred[tuple[T1, T2]]": ...
 
 
 @overload
 def gather_results(
-    deferredList: Tuple[
+    deferredList: tuple[
         "defer.Deferred[T1]", "defer.Deferred[T2]", "defer.Deferred[T3]"
     ],
     consumeErrors: bool = ...,
-) -> "defer.Deferred[Tuple[T1, T2, T3]]": ...
+) -> "defer.Deferred[tuple[T1, T2, T3]]": ...
 
 
 @overload
 def gather_results(
-    deferredList: Tuple[
+    deferredList: tuple[
         "defer.Deferred[T1]",
         "defer.Deferred[T2]",
         "defer.Deferred[T3]",
         "defer.Deferred[T4]",
     ],
     consumeErrors: bool = ...,
-) -> "defer.Deferred[Tuple[T1, T2, T3, T4]]": ...
+) -> "defer.Deferred[tuple[T1, T2, T3, T4]]": ...
 
 
 def gather_results(  # type: ignore[misc]
-    deferredList: Tuple["defer.Deferred[T1]", ...],
+    deferredList: tuple["defer.Deferred[T1]", ...],
     consumeErrors: bool = False,
-) -> "defer.Deferred[Tuple[T1, ...]]":
+) -> "defer.Deferred[tuple[T1, ...]]":
     """Combines a tuple of `Deferred`s into a single `Deferred`.
 
     Wraps `defer.gatherResults` to provide type annotations that support heterogenous
@@ -408,104 +401,102 @@ def gather_results(  # type: ignore[misc]
 
 @overload
 async def gather_optional_coroutines(
-    *coroutines: Unpack[Tuple[Optional[Coroutine[Any, Any, T1]]]],
-) -> Tuple[Optional[T1]]: ...
+    *coroutines: Unpack[tuple[Coroutine[Any, Any, T1] | None]],
+) -> tuple[T1 | None]: ...
 
 
 @overload
 async def gather_optional_coroutines(
     *coroutines: Unpack[
-        Tuple[
-            Optional[Coroutine[Any, Any, T1]],
-            Optional[Coroutine[Any, Any, T2]],
+        tuple[
+            Coroutine[Any, Any, T1] | None,
+            Coroutine[Any, Any, T2] | None,
         ]
     ],
-) -> Tuple[Optional[T1], Optional[T2]]: ...
+) -> tuple[T1 | None, T2 | None]: ...
 
 
 @overload
 async def gather_optional_coroutines(
     *coroutines: Unpack[
-        Tuple[
-            Optional[Coroutine[Any, Any, T1]],
-            Optional[Coroutine[Any, Any, T2]],
-            Optional[Coroutine[Any, Any, T3]],
+        tuple[
+            Coroutine[Any, Any, T1] | None,
+            Coroutine[Any, Any, T2] | None,
+            Coroutine[Any, Any, T3] | None,
         ]
     ],
-) -> Tuple[Optional[T1], Optional[T2], Optional[T3]]: ...
+) -> tuple[T1 | None, T2 | None, T3 | None]: ...
 
 
 @overload
 async def gather_optional_coroutines(
     *coroutines: Unpack[
-        Tuple[
-            Optional[Coroutine[Any, Any, T1]],
-            Optional[Coroutine[Any, Any, T2]],
-            Optional[Coroutine[Any, Any, T3]],
-            Optional[Coroutine[Any, Any, T4]],
+        tuple[
+            Coroutine[Any, Any, T1] | None,
+            Coroutine[Any, Any, T2] | None,
+            Coroutine[Any, Any, T3] | None,
+            Coroutine[Any, Any, T4] | None,
         ]
     ],
-) -> Tuple[Optional[T1], Optional[T2], Optional[T3], Optional[T4]]: ...
+) -> tuple[T1 | None, T2 | None, T3 | None, T4 | None]: ...
 
 
 @overload
 async def gather_optional_coroutines(
     *coroutines: Unpack[
-        Tuple[
-            Optional[Coroutine[Any, Any, T1]],
-            Optional[Coroutine[Any, Any, T2]],
-            Optional[Coroutine[Any, Any, T3]],
-            Optional[Coroutine[Any, Any, T4]],
-            Optional[Coroutine[Any, Any, T5]],
+        tuple[
+            Coroutine[Any, Any, T1] | None,
+            Coroutine[Any, Any, T2] | None,
+            Coroutine[Any, Any, T3] | None,
+            Coroutine[Any, Any, T4] | None,
+            Coroutine[Any, Any, T5] | None,
         ]
     ],
-) -> Tuple[Optional[T1], Optional[T2], Optional[T3], Optional[T4], Optional[T5]]: ...
+) -> tuple[T1 | None, T2 | None, T3 | None, T4 | None, T5 | None]: ...
 
 
 @overload
 async def gather_optional_coroutines(
     *coroutines: Unpack[
-        Tuple[
-            Optional[Coroutine[Any, Any, T1]],
-            Optional[Coroutine[Any, Any, T2]],
-            Optional[Coroutine[Any, Any, T3]],
-            Optional[Coroutine[Any, Any, T4]],
-            Optional[Coroutine[Any, Any, T5]],
-            Optional[Coroutine[Any, Any, T6]],
+        tuple[
+            Coroutine[Any, Any, T1] | None,
+            Coroutine[Any, Any, T2] | None,
+            Coroutine[Any, Any, T3] | None,
+            Coroutine[Any, Any, T4] | None,
+            Coroutine[Any, Any, T5] | None,
+            Coroutine[Any, Any, T6] | None,
         ]
     ],
-) -> Tuple[
-    Optional[T1], Optional[T2], Optional[T3], Optional[T4], Optional[T5], Optional[T6]
-]: ...
+) -> tuple[T1 | None, T2 | None, T3 | None, T4 | None, T5 | None, T6 | None]: ...
 
 
 @overload
 async def gather_optional_coroutines(
     *coroutines: Unpack[
-        Tuple[
-            Optional[Coroutine[Any, Any, T1]],
-            Optional[Coroutine[Any, Any, T2]],
-            Optional[Coroutine[Any, Any, T3]],
-            Optional[Coroutine[Any, Any, T4]],
-            Optional[Coroutine[Any, Any, T5]],
-            Optional[Coroutine[Any, Any, T6]],
-            Optional[Coroutine[Any, Any, T7]],
+        tuple[
+            Coroutine[Any, Any, T1] | None,
+            Coroutine[Any, Any, T2] | None,
+            Coroutine[Any, Any, T3] | None,
+            Coroutine[Any, Any, T4] | None,
+            Coroutine[Any, Any, T5] | None,
+            Coroutine[Any, Any, T6] | None,
+            Coroutine[Any, Any, T7] | None,
         ]
     ],
-) -> Tuple[
-    Optional[T1],
-    Optional[T2],
-    Optional[T3],
-    Optional[T4],
-    Optional[T5],
-    Optional[T6],
-    Optional[T7],
+) -> tuple[
+    T1 | None,
+    T2 | None,
+    T3 | None,
+    T4 | None,
+    T5 | None,
+    T6 | None,
+    T7 | None,
 ]: ...
 
 
 async def gather_optional_coroutines(
-    *coroutines: Unpack[Tuple[Optional[Coroutine[Any, Any, T1]], ...]],
-) -> Tuple[Optional[T1], ...]:
+    *coroutines: Unpack[tuple[Coroutine[Any, Any, T1] | None, ...]],
+) -> tuple[T1 | None, ...]:
     """Helper function that allows waiting on multiple coroutines at once.
 
     The return value is a tuple of the return values of the coroutines in order.
@@ -574,10 +565,9 @@ class Linearizer:
 
     def __init__(
         self,
-        *,
         name: str,
-        max_count: int = 1,
         clock: Clock,
+        max_count: int = 1,
     ):
         """
         Args:
@@ -590,7 +580,7 @@ class Linearizer:
         self._clock = clock
 
         # key_to_defer is a map from the key to a _LinearizerEntry.
-        self.key_to_defer: Dict[Hashable, _LinearizerEntry] = {}
+        self.key_to_defer: dict[Hashable, _LinearizerEntry] = {}
 
     def is_queued(self, key: Hashable) -> bool:
         """Checks whether there is a process queued up waiting"""
@@ -725,10 +715,10 @@ class ReadWriteLock:
 
     def __init__(self) -> None:
         # Latest readers queued
-        self.key_to_current_readers: Dict[str, Set[defer.Deferred]] = {}
+        self.key_to_current_readers: dict[str, set[defer.Deferred]] = {}
 
         # Latest writer queued
-        self.key_to_current_writer: Dict[str, defer.Deferred] = {}
+        self.key_to_current_writer: dict[str, defer.Deferred] = {}
 
     def read(self, key: str) -> AsyncContextManager:
         @asynccontextmanager
@@ -797,7 +787,11 @@ class ReadWriteLock:
 
 
 def timeout_deferred(
-    deferred: "defer.Deferred[_T]", timeout: float, reactor: IReactorTime
+    *,
+    deferred: "defer.Deferred[_T]",
+    timeout: float,
+    cancel_on_shutdown: bool = True,
+    clock: Clock,
 ) -> "defer.Deferred[_T]":
     """The in built twisted `Deferred.addTimeout` fails to time out deferreds
     that have a canceller that throws exceptions. This method creates a new
@@ -815,7 +809,13 @@ def timeout_deferred(
     Args:
         deferred: The Deferred to potentially timeout.
         timeout: Timeout in seconds
-        reactor: The twisted reactor to use
+        cancel_on_shutdown: Whether this call should be tracked for cleanup during
+            shutdown. In general, all calls should be tracked. There may be a use case
+            not to track calls with a `timeout` of 0 (or similarly short) since tracking
+            them may result in rapid insertions and removals of tracked calls
+            unnecessarily. But unless a specific instance of tracking proves to be an
+            issue, we can just track all delayed calls.
+        clock: The `Clock` instance used to track delayed calls.
 
 
     Returns:
@@ -829,7 +829,8 @@ def timeout_deferred(
         timed_out[0] = True
 
         try:
-            deferred.cancel()
+            with PreserveLoggingContext():
+                deferred.cancel()
         except Exception:  # if we throw any exception it'll break time outs
             logger.exception("Canceller failed during timeout")
 
@@ -839,7 +840,10 @@ def timeout_deferred(
         if not new_d.called:
             new_d.errback(defer.TimeoutError("Timed out after %gs" % (timeout,)))
 
-    delayed_call = reactor.callLater(timeout, time_it_out)
+    # We don't track these calls since they are short.
+    delayed_call = clock.call_later(
+        timeout, time_it_out, call_later_cancel_on_shutdown=cancel_on_shutdown
+    )
 
     def convert_cancelled(value: Failure) -> Failure:
         # if the original deferred was cancelled, and our timeout has fired, then
@@ -883,7 +887,7 @@ class DoneAwaitable(Awaitable[R]):
         return self.value
 
 
-def maybe_awaitable(value: Union[Awaitable[R], R]) -> Awaitable[R]:
+def maybe_awaitable(value: Awaitable[R] | R) -> Awaitable[R]:
     """Convert a value to an awaitable if not already an awaitable."""
     if inspect.isawaitable(value):
         return value
@@ -981,9 +985,9 @@ class AwakenableSleeper:
     currently sleeping.
     """
 
-    def __init__(self, reactor: IReactorTime) -> None:
-        self._streams: Dict[str, Set[defer.Deferred[None]]] = {}
-        self._reactor = reactor
+    def __init__(self, clock: Clock) -> None:
+        self._streams: dict[str, set[defer.Deferred[None]]] = {}
+        self._clock = clock
 
     def wake(self, name: str) -> None:
         """Wake everything related to `name` that is currently sleeping."""
@@ -1002,7 +1006,11 @@ class AwakenableSleeper:
 
         # Create a deferred that gets called in N seconds
         sleep_deferred: "defer.Deferred[None]" = defer.Deferred()
-        call = self._reactor.callLater(delay_ms / 1000, sleep_deferred.callback, None)
+        call = self._clock.call_later(
+            delay_ms / 1000,
+            sleep_deferred.callback,
+            None,
+        )
 
         # Create a deferred that will get called if `wake` is called with
         # the same `name`.
@@ -1036,13 +1044,14 @@ class AwakenableSleeper:
 class DeferredEvent:
     """Like threading.Event but for async code"""
 
-    def __init__(self, reactor: IReactorTime) -> None:
-        self._reactor = reactor
+    def __init__(self, clock: Clock) -> None:
+        self._clock = clock
         self._deferred: "defer.Deferred[None]" = defer.Deferred()
 
     def set(self) -> None:
         if not self._deferred.called:
-            self._deferred.callback(None)
+            with PreserveLoggingContext():
+                self._deferred.callback(None)
 
     def clear(self) -> None:
         if self._deferred.called:
@@ -1055,22 +1064,15 @@ class DeferredEvent:
         if self.is_set():
             return True
 
-        # Create a deferred that gets called in N seconds
-        sleep_deferred: "defer.Deferred[None]" = defer.Deferred()
-        call = self._reactor.callLater(timeout_seconds, sleep_deferred.callback, None)
-
         try:
             await make_deferred_yieldable(
-                defer.DeferredList(
-                    [sleep_deferred, self._deferred],
-                    fireOnOneCallback=True,
-                    fireOnOneErrback=True,
-                    consumeErrors=True,
+                timeout_deferred(
+                    deferred=stop_cancellation(self._deferred),
+                    timeout=timeout_seconds,
+                    clock=self._clock,
                 )
             )
-        finally:
-            # Cancel the sleep if we were woken up
-            if call.active():
-                call.cancel()
+        except defer.TimeoutError:
+            pass
 
         return self.is_set()
diff --git a/synapse/util/background_queue.py b/synapse/util/background_queue.py
new file mode 100644
index 0000000000..93ffd9f271
--- /dev/null
+++ b/synapse/util/background_queue.py
@@ -0,0 +1,142 @@
+#
+# This file is licensed under the Affero General Public License (AGPL) version 3.
+#
+# Copyright (C) 2025 Element Creations Ltd
+#
+# This program is free software: you can redistribute it and/or modify
+# it under the terms of the GNU Affero General Public License as
+# published by the Free Software Foundation, either version 3 of the
+# License, or (at your option) any later version.
+#
+# See the GNU Affero General Public License for more details:
+# <https://www.gnu.org/licenses/agpl-3.0.html>.
+#
+#
+#
+
+import collections
+import logging
+from typing import (
+    TYPE_CHECKING,
+    Awaitable,
+    Callable,
+    Generic,
+    TypeVar,
+)
+
+from twisted.internet import defer
+
+from synapse.util.async_helpers import DeferredEvent
+from synapse.util.constants import MILLISECONDS_PER_SECOND
+
+if TYPE_CHECKING:
+    from synapse.server import HomeServer
+
+logger = logging.getLogger(__name__)
+
+T = TypeVar("T")
+
+
+class BackgroundQueue(Generic[T]):
+    """A single-producer single-consumer async queue processing items in the
+    background.
+
+    This is optimised for the case where we receive many items, but processing
+    each one takes a short amount of time. In this case we don't want to pay the
+    overhead of a new background process each time. Instead, we spawn a
+    background process that will wait for new items to arrive.
+
+    If the background process has been idle for a while, it will exit, and a new
+    background process will be spawned when new items arrive.
+
+    Args:
+        hs: The homeserver.
+        name: The name of the background process.
+        callback: The async callback to process each item.
+        timeout_ms: The time in milliseconds to wait for new items before
+            exiting the background process.
+    """
+
+    def __init__(
+        self,
+        hs: "HomeServer",
+        name: str,
+        callback: Callable[[T], Awaitable[None]],
+        timeout_ms: int = 1000,
+    ) -> None:
+        self._hs = hs
+        self._name = name
+        self._callback = callback
+        self._timeout_ms = timeout_ms
+
+        # The queue of items to process.
+        self._queue: collections.deque[T] = collections.deque()
+
+        # Indicates if a background process is running, and if so whether there
+        # is new data in the queue. Used to signal to an existing background
+        # process that there is new data added to the queue.
+        self._wakeup_event: DeferredEvent | None = None
+
+    def add(self, item: T) -> None:
+        """Add an item into the queue."""
+
+        self._queue.append(item)
+        if self._wakeup_event is None:
+            self._hs.run_as_background_process(self._name, self._process_queue)
+        else:
+            self._wakeup_event.set()
+
+    async def _process_queue(self) -> None:
+        """Process items in the queue until it is empty."""
+
+        # Make sure we're the only background process.
+        if self._wakeup_event is not None:
+            # If there is already a background process then we signal it to wake
+            # up and exit. We do not want multiple background processes running
+            # at a time.
+            self._wakeup_event.set()
+            return
+
+        self._wakeup_event = DeferredEvent(self._hs.get_clock())
+
+        try:
+            while True:
+                # Clear the event before checking the queue. If we cleared after
+                # we run the risk of the wakeup signal racing with us checking
+                # the queue. (This can't really happen in Python due to the
+                # single threaded nature, but let's be a bit defensive anyway.)
+                self._wakeup_event.clear()
+
+                while self._queue:
+                    item = self._queue.popleft()
+                    try:
+                        await self._callback(item)
+                    except defer.CancelledError:
+                        raise
+                    except Exception:
+                        logger.exception("Error processing background queue item")
+
+                # Wait for new data to arrive, timing out after a while to avoid
+                # keeping the background process alive forever.
+                #
+                # New data may have arrived and been processed while we were
+                # pulling from the queue, so this may return that there is new
+                # data immediately even though there isn't. That's fine, we'll
+                # just loop round, clear the event, recheck the queue, and then
+                # wait here again.
+                new_data = await self._wakeup_event.wait(
+                    timeout_seconds=self._timeout_ms / MILLISECONDS_PER_SECOND
+                )
+                if not new_data:
+                    # Timed out waiting for new data, so exit the loop
+                    break
+        finally:
+            # This background process is exiting, so clear the wakeup event to
+            # indicate that a new one should be started when new data arrives.
+            self._wakeup_event = None
+
+            # The queue must be empty here.
+            assert not self._queue
+
+    def __len__(self) -> int:
+        return len(self._queue)
diff --git a/synapse/util/batching_queue.py b/synapse/util/batching_queue.py
index 4c4037412a..514abcbec1 100644
--- a/synapse/util/batching_queue.py
+++ b/synapse/util/batching_queue.py
@@ -21,14 +21,11 @@
 
 import logging
 from typing import (
+    TYPE_CHECKING,
     Awaitable,
     Callable,
-    Dict,
     Generic,
     Hashable,
-    List,
-    Set,
-    Tuple,
     TypeVar,
 )
 
@@ -38,9 +35,11 @@ from twisted.internet import defer
 
 from synapse.logging.context import PreserveLoggingContext, make_deferred_yieldable
 from synapse.metrics import SERVER_NAME_LABEL
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.util.clock import Clock
 
+if TYPE_CHECKING:
+    from synapse.server import HomeServer
+
 logger = logging.getLogger(__name__)
 
 
@@ -97,20 +96,21 @@ class BatchingQueue(Generic[V, R]):
         self,
         *,
         name: str,
-        server_name: str,
+        hs: "HomeServer",
         clock: Clock,
-        process_batch_callback: Callable[[List[V]], Awaitable[R]],
+        process_batch_callback: Callable[[list[V]], Awaitable[R]],
     ):
         self._name = name
-        self.server_name = server_name
+        self.hs = hs
+        self.server_name = hs.hostname
         self._clock = clock
 
         # The set of keys currently being processed.
-        self._processing_keys: Set[Hashable] = set()
+        self._processing_keys: set[Hashable] = set()
 
         # The currently pending batch of values by key, with a Deferred to call
         # with the result of the corresponding `_process_batch_callback` call.
-        self._next_values: Dict[Hashable, List[Tuple[V, defer.Deferred]]] = {}
+        self._next_values: dict[Hashable, list[tuple[V, defer.Deferred]]] = {}
 
         # The function to call with batches of values.
         self._process_batch_callback = process_batch_callback
@@ -127,6 +127,14 @@ class BatchingQueue(Generic[V, R]):
             name=self._name, **{SERVER_NAME_LABEL: self.server_name}
         )
 
+    def shutdown(self) -> None:
+        """
+        Prepares the object for garbage collection by removing any handed out
+        references.
+        """
+        number_queued.remove(self._name, self.server_name)
+        number_of_keys.remove(self._name, self.server_name)
+
     async def add_to_queue(self, value: V, key: Hashable = ()) -> R:
         """Adds the value to the queue with the given key, returning the result
         of the processing function for the batch that included the given value.
@@ -145,9 +153,7 @@ class BatchingQueue(Generic[V, R]):
         # If we're not currently processing the key fire off a background
         # process to start processing.
         if key not in self._processing_keys:
-            run_as_background_process(
-                self._name, self.server_name, self._process_queue, key
-            )
+            self.hs.run_as_background_process(self._name, self._process_queue, key)
 
         with self._number_in_flight_metric.track_inprogress():
             return await make_deferred_yieldable(d)
diff --git a/synapse/util/caches/__init__.py b/synapse/util/caches/__init__.py
index 710a29e3f0..a65ab7f57d 100644
--- a/synapse/util/caches/__init__.py
+++ b/synapse/util/caches/__init__.py
@@ -24,7 +24,7 @@ import logging
 import typing
 from enum import Enum, auto
 from sys import intern
-from typing import Any, Callable, Dict, List, Optional, Sized, TypeVar
+from typing import Any, Callable, Sized, TypeVar
 
 import attr
 from prometheus_client import REGISTRY
@@ -129,7 +129,7 @@ class CacheMetric:
     _cache: Sized
     _cache_type: str
     _cache_name: str
-    _collect_callback: Optional[Callable]
+    _collect_callback: Callable | None
     _server_name: str
 
     hits: int = 0
@@ -137,7 +137,7 @@ class CacheMetric:
     eviction_size_by_reason: typing.Counter[EvictionReason] = attr.ib(
         factory=collections.Counter
     )
-    memory_usage: Optional[int] = None
+    memory_usage: int | None = None
 
     def inc_hits(self) -> None:
         self.hits += 1
@@ -162,7 +162,7 @@ class CacheMetric:
         if self.memory_usage is not None:
             self.memory_usage = 0
 
-    def describe(self) -> List[str]:
+    def describe(self) -> list[str]:
         return []
 
     def collect(self) -> None:
@@ -208,9 +208,9 @@ def register_cache(
     cache_name: str,
     cache: Sized,
     server_name: str,
-    collect_callback: Optional[Callable] = None,
+    collect_callback: Callable | None = None,
     resizable: bool = True,
-    resize_callback: Optional[Callable] = None,
+    resize_callback: Callable | None = None,
 ) -> CacheMetric:
     """Register a cache object for metric collection and resizing.
 
@@ -244,7 +244,7 @@ def register_cache(
         collect_callback=collect_callback,
     )
     metric_name = "cache_%s_%s_%s" % (cache_type, cache_name, server_name)
-    CACHE_METRIC_REGISTRY.register_hook(metric_name, metric.collect)
+    CACHE_METRIC_REGISTRY.register_hook(server_name, metric_name, metric.collect)
     return metric
 
 
@@ -269,7 +269,7 @@ KNOWN_KEYS = {
     )
 }
 
-T = TypeVar("T", Optional[str], str)
+T = TypeVar("T", str | None, str)
 
 
 def intern_string(string: T) -> T:
@@ -283,7 +283,7 @@ def intern_string(string: T) -> T:
         return string
 
 
-def intern_dict(dictionary: Dict[str, Any]) -> Dict[str, Any]:
+def intern_dict(dictionary: dict[str, Any]) -> dict[str, Any]:
     """Takes a dictionary and interns well known keys and their values"""
     return {
         KNOWN_KEYS.get(key, key): _intern_known_values(key, value)
diff --git a/synapse/util/caches/cached_call.py b/synapse/util/caches/cached_call.py
index 9b86017cd9..491e7e52a1 100644
--- a/synapse/util/caches/cached_call.py
+++ b/synapse/util/caches/cached_call.py
@@ -19,7 +19,7 @@
 #
 #
 import enum
-from typing import Awaitable, Callable, Generic, Optional, TypeVar, Union
+from typing import Awaitable, Callable, Generic, TypeVar
 
 from twisted.internet.defer import Deferred
 from twisted.python.failure import Failure
@@ -74,9 +74,9 @@ class CachedCall(Generic[TV]):
             f: The underlying function. Only one call to this function will be alive
                 at once (per instance of CachedCall)
         """
-        self._callable: Optional[Callable[[], Awaitable[TV]]] = f
-        self._deferred: Optional[Deferred] = None
-        self._result: Union[_Sentinel, TV, Failure] = _Sentinel.sentinel
+        self._callable: Callable[[], Awaitable[TV]] | None = f
+        self._deferred: Deferred | None = None
+        self._result: _Sentinel | TV | Failure = _Sentinel.sentinel
 
     async def get(self) -> TV:
         """Kick off the call if necessary, and return the result"""
@@ -93,7 +93,7 @@ class CachedCall(Generic[TV]):
             # result in the deferred, since `awaiting` a deferred destroys its result.
             # (Also, if it's a Failure, GCing the deferred would log a critical error
             # about unhandled Failures)
-            def got_result(r: Union[TV, Failure]) -> None:
+            def got_result(r: TV | Failure) -> None:
                 self._result = r
 
             self._deferred.addBoth(got_result)
diff --git a/synapse/util/caches/deferred_cache.py b/synapse/util/caches/deferred_cache.py
index 92d446ce2a..a1601cd4e9 100644
--- a/synapse/util/caches/deferred_cache.py
+++ b/synapse/util/caches/deferred_cache.py
@@ -26,15 +26,11 @@ import threading
 from typing import (
     Callable,
     Collection,
-    Dict,
     Generic,
     MutableMapping,
     Optional,
-    Set,
     Sized,
-    Tuple,
     TypeVar,
-    Union,
     cast,
 )
 
@@ -47,6 +43,7 @@ from synapse.metrics import SERVER_NAME_LABEL
 from synapse.util.async_helpers import ObservableDeferred
 from synapse.util.caches.lrucache import LruCache
 from synapse.util.caches.treecache import TreeCache, iterate_tree_cache_entry
+from synapse.util.clock import Clock
 
 cache_pending_metric = Gauge(
     "synapse_util_caches_cache_pending",
@@ -82,6 +79,7 @@ class DeferredCache(Generic[KT, VT]):
         self,
         *,
         name: str,
+        clock: Clock,
         server_name: str,
         max_entries: int = 1000,
         tree: bool = False,
@@ -103,13 +101,14 @@ class DeferredCache(Generic[KT, VT]):
             prune_unread_entries: If True, cache entries that haven't been read recently
                 will be evicted from the cache in the background. Set to False to
                 opt-out of this behaviour.
+            clock: The homeserver `Clock` instance
         """
         cache_type = TreeCache if tree else dict
 
         # _pending_deferred_cache maps from the key value to a `CacheEntry` object.
-        self._pending_deferred_cache: Union[
-            TreeCache, "MutableMapping[KT, CacheEntry[KT, VT]]"
-        ] = cache_type()
+        self._pending_deferred_cache: (
+            TreeCache | "MutableMapping[KT, CacheEntry[KT, VT]]"
+        ) = cache_type()
 
         def metrics_cb() -> None:
             cache_pending_metric.labels(
@@ -120,6 +119,7 @@ class DeferredCache(Generic[KT, VT]):
         # a Deferred.
         self.cache: LruCache[KT, VT] = LruCache(
             max_size=max_entries,
+            clock=clock,
             server_name=server_name,
             cache_name=name,
             cache_type=cache_type,
@@ -135,7 +135,7 @@ class DeferredCache(Generic[KT, VT]):
             prune_unread_entries=prune_unread_entries,
         )
 
-        self.thread: Optional[threading.Thread] = None
+        self.thread: threading.Thread | None = None
 
     @property
     def max_entries(self) -> int:
@@ -154,7 +154,7 @@ class DeferredCache(Generic[KT, VT]):
     def get(
         self,
         key: KT,
-        callback: Optional[Callable[[], None]] = None,
+        callback: Callable[[], None] | None = None,
         update_metrics: bool = True,
     ) -> defer.Deferred:
         """Looks the key up in the caches.
@@ -198,8 +198,8 @@ class DeferredCache(Generic[KT, VT]):
     def get_bulk(
         self,
         keys: Collection[KT],
-        callback: Optional[Callable[[], None]] = None,
-    ) -> Tuple[Dict[KT, VT], Optional["defer.Deferred[Dict[KT, VT]]"], Collection[KT]]:
+        callback: Callable[[], None] | None = None,
+    ) -> tuple[dict[KT, VT], Optional["defer.Deferred[dict[KT, VT]]"], Collection[KT]]:
         """Bulk lookup of items in the cache.
 
         Returns:
@@ -262,9 +262,7 @@ class DeferredCache(Generic[KT, VT]):
 
         return (cached, pending_deferred, missing)
 
-    def get_immediate(
-        self, key: KT, default: T, update_metrics: bool = True
-    ) -> Union[VT, T]:
+    def get_immediate(self, key: KT, default: T, update_metrics: bool = True) -> VT | T:
         """If we have a *completed* cached value, return it."""
         return self.cache.get(key, default, update_metrics=update_metrics)
 
@@ -272,7 +270,7 @@ class DeferredCache(Generic[KT, VT]):
         self,
         key: KT,
         value: "defer.Deferred[VT]",
-        callback: Optional[Callable[[], None]] = None,
+        callback: Callable[[], None] | None = None,
     ) -> defer.Deferred:
         """Adds a new entry to the cache (or updates an existing one).
 
@@ -327,7 +325,7 @@ class DeferredCache(Generic[KT, VT]):
     def start_bulk_input(
         self,
         keys: Collection[KT],
-        callback: Optional[Callable[[], None]] = None,
+        callback: Callable[[], None] | None = None,
     ) -> "CacheMultipleEntries[KT, VT]":
         """Bulk set API for use when fetching multiple keys at once from the DB.
 
@@ -381,7 +379,7 @@ class DeferredCache(Generic[KT, VT]):
         return failure
 
     def prefill(
-        self, key: KT, value: VT, callback: Optional[Callable[[], None]] = None
+        self, key: KT, value: VT, callback: Callable[[], None] | None = None
     ) -> None:
         callbacks = (callback,) if callback else ()
         self.cache.set(key, value, callbacks=callbacks)
@@ -434,7 +432,7 @@ class CacheEntry(Generic[KT, VT], metaclass=abc.ABCMeta):
 
     @abc.abstractmethod
     def add_invalidation_callback(
-        self, key: KT, callback: Optional[Callable[[], None]]
+        self, key: KT, callback: Callable[[], None] | None
     ) -> None:
         """Add an invalidation callback"""
         ...
@@ -454,13 +452,13 @@ class CacheEntrySingle(CacheEntry[KT, VT]):
 
     def __init__(self, deferred: "defer.Deferred[VT]") -> None:
         self._deferred = ObservableDeferred(deferred, consumeErrors=True)
-        self._callbacks: Set[Callable[[], None]] = set()
+        self._callbacks: set[Callable[[], None]] = set()
 
     def deferred(self, key: KT) -> "defer.Deferred[VT]":
         return self._deferred.observe()
 
     def add_invalidation_callback(
-        self, key: KT, callback: Optional[Callable[[], None]]
+        self, key: KT, callback: Callable[[], None] | None
     ) -> None:
         if callback is None:
             return
@@ -477,9 +475,9 @@ class CacheMultipleEntries(CacheEntry[KT, VT]):
     __slots__ = ["_deferred", "_callbacks", "_global_callbacks"]
 
     def __init__(self) -> None:
-        self._deferred: Optional[ObservableDeferred[Dict[KT, VT]]] = None
-        self._callbacks: Dict[KT, Set[Callable[[], None]]] = {}
-        self._global_callbacks: Set[Callable[[], None]] = set()
+        self._deferred: ObservableDeferred[dict[KT, VT]] | None = None
+        self._callbacks: dict[KT, set[Callable[[], None]]] = {}
+        self._global_callbacks: set[Callable[[], None]] = set()
 
     def deferred(self, key: KT) -> "defer.Deferred[VT]":
         if not self._deferred:
@@ -487,7 +485,7 @@ class CacheMultipleEntries(CacheEntry[KT, VT]):
         return self._deferred.observe().addCallback(lambda res: res[key])
 
     def add_invalidation_callback(
-        self, key: KT, callback: Optional[Callable[[], None]]
+        self, key: KT, callback: Callable[[], None] | None
     ) -> None:
         if callback is None:
             return
@@ -498,7 +496,7 @@ class CacheMultipleEntries(CacheEntry[KT, VT]):
         return self._callbacks.get(key, set()) | self._global_callbacks
 
     def add_global_invalidation_callback(
-        self, callback: Optional[Callable[[], None]]
+        self, callback: Callable[[], None] | None
     ) -> None:
         """Add a callback for when any keys get invalidated."""
         if callback is None:
@@ -509,7 +507,7 @@ class CacheMultipleEntries(CacheEntry[KT, VT]):
     def complete_bulk(
         self,
         cache: DeferredCache[KT, VT],
-        result: Dict[KT, VT],
+        result: dict[KT, VT],
     ) -> None:
         """Called when there is a result"""
         for key, value in result.items():
diff --git a/synapse/util/caches/descriptors.py b/synapse/util/caches/descriptors.py
index 47b8f4ddc8..fd931cac89 100644
--- a/synapse/util/caches/descriptors.py
+++ b/synapse/util/caches/descriptors.py
@@ -26,19 +26,13 @@ from typing import (
     Awaitable,
     Callable,
     Collection,
-    Dict,
     Generic,
     Hashable,
     Iterable,
-    List,
     Mapping,
-    Optional,
     Protocol,
     Sequence,
-    Tuple,
-    Type,
     TypeVar,
-    Union,
     cast,
 )
 from weakref import WeakValueDictionary
@@ -53,18 +47,19 @@ from synapse.util import unwrapFirstError
 from synapse.util.async_helpers import delay_cancellation
 from synapse.util.caches.deferred_cache import DeferredCache
 from synapse.util.caches.lrucache import LruCache
+from synapse.util.clock import Clock
 
 logger = logging.getLogger(__name__)
 
-CacheKey = Union[Tuple, Any]
+CacheKey = tuple | Any
 
 F = TypeVar("F", bound=Callable[..., Any])
 
 
 class CachedFunction(Generic[F]):
-    invalidate: Callable[[Tuple[Any, ...]], None]
+    invalidate: Callable[[tuple[Any, ...]], None]
     invalidate_all: Callable[[], None]
-    prefill: Callable[[Tuple[Any, ...], Any], None]
+    prefill: Callable[[tuple[Any, ...], Any], None]
     cache: Any = None
     num_args: Any = None
 
@@ -79,10 +74,10 @@ class _CacheDescriptorBase:
     def __init__(
         self,
         orig: Callable[..., Any],
-        num_args: Optional[int],
-        uncached_args: Optional[Collection[str]] = None,
+        num_args: int | None,
+        uncached_args: Collection[str] | None = None,
         cache_context: bool = False,
-        name: Optional[str] = None,
+        name: str | None = None,
     ):
         self.orig = orig
         self.name = name or orig.__name__
@@ -154,13 +149,20 @@ class _CacheDescriptorBase:
         )
 
 
-class HasServerName(Protocol):
+class HasServerNameAndClock(Protocol):
     server_name: str
     """
     The homeserver name that this cache is associated with (used to label the metric)
     (`hs.hostname`).
     """
 
+    clock: Clock
+    """
+    The homeserver clock instance used to track delayed and looping calls. Important to
+    be able to fully cleanup the homeserver instance on server shutdown.
+    (`hs.get_clock()`).
+    """
+
 
 class DeferredCacheDescriptor(_CacheDescriptorBase):
     """A method decorator that applies a memoizing cache around the function.
@@ -212,13 +214,13 @@ class DeferredCacheDescriptor(_CacheDescriptorBase):
         *,
         orig: Callable[..., Any],
         max_entries: int = 1000,
-        num_args: Optional[int] = None,
-        uncached_args: Optional[Collection[str]] = None,
+        num_args: int | None = None,
+        uncached_args: Collection[str] | None = None,
         tree: bool = False,
         cache_context: bool = False,
         iterable: bool = False,
         prune_unread_entries: bool = True,
-        name: Optional[str] = None,
+        name: str | None = None,
     ):
         super().__init__(
             orig,
@@ -239,7 +241,7 @@ class DeferredCacheDescriptor(_CacheDescriptorBase):
         self.prune_unread_entries = prune_unread_entries
 
     def __get__(
-        self, obj: Optional[HasServerName], owner: Optional[Type]
+        self, obj: HasServerNameAndClock | None, owner: type | None
     ) -> Callable[..., "defer.Deferred[Any]"]:
         # We need access to instance-level `obj.server_name` attribute
         assert obj is not None, (
@@ -249,9 +251,13 @@ class DeferredCacheDescriptor(_CacheDescriptorBase):
         assert obj.server_name is not None, (
             "The `server_name` attribute must be set on the object where `@cached` decorator is used."
         )
+        assert obj.clock is not None, (
+            "The `clock` attribute must be set on the object where `@cached` decorator is used."
+        )
 
         cache: DeferredCache[CacheKey, Any] = DeferredCache(
             name=self.name,
+            clock=obj.clock,
             server_name=obj.server_name,
             max_entries=self.max_entries,
             tree=self.tree,
@@ -320,11 +326,11 @@ class DeferredCacheListDescriptor(_CacheDescriptorBase):
 
     def __init__(
         self,
-        orig: Callable[..., Awaitable[Dict]],
+        orig: Callable[..., Awaitable[dict]],
         cached_method_name: str,
         list_name: str,
-        num_args: Optional[int] = None,
-        name: Optional[str] = None,
+        num_args: int | None = None,
+        name: str | None = None,
     ):
         """
         Args:
@@ -351,8 +357,8 @@ class DeferredCacheListDescriptor(_CacheDescriptorBase):
             )
 
     def __get__(
-        self, obj: Optional[Any], objtype: Optional[Type] = None
-    ) -> Callable[..., "defer.Deferred[Dict[Hashable, Any]]"]:
+        self, obj: Any | None, objtype: type | None = None
+    ) -> Callable[..., "defer.Deferred[dict[Hashable, Any]]"]:
         cached_method = getattr(obj, self.cached_method_name)
         cache: DeferredCache[CacheKey, Any] = cached_method.cache
         num_args = cached_method.num_args
@@ -364,7 +370,7 @@ class DeferredCacheListDescriptor(_CacheDescriptorBase):
             )
 
         @functools.wraps(self.orig)
-        def wrapped(*args: Any, **kwargs: Any) -> "defer.Deferred[Dict]":
+        def wrapped(*args: Any, **kwargs: Any) -> "defer.Deferred[dict]":
             # If we're passed a cache_context then we'll want to call its
             # invalidate() whenever we are invalidated
             invalidate_callback = kwargs.pop("on_invalidate", None)
@@ -400,10 +406,10 @@ class DeferredCacheListDescriptor(_CacheDescriptorBase):
 
             results = {cache_key_to_arg(key): v for key, v in immediate_results.items()}
 
-            cached_defers: List["defer.Deferred[Any]"] = []
+            cached_defers: list["defer.Deferred[Any]"] = []
             if pending_deferred:
 
-                def update_results(r: Dict) -> None:
+                def update_results(r: dict) -> None:
                     for k, v in r.items():
                         results[cache_key_to_arg(k)] = v
 
@@ -413,7 +419,7 @@ class DeferredCacheListDescriptor(_CacheDescriptorBase):
             if missing:
                 cache_entry = cache.start_bulk_input(missing, invalidate_callback)
 
-                def complete_all(res: Dict[Hashable, Any]) -> None:
+                def complete_all(res: dict[Hashable, Any]) -> None:
                     missing_results = {}
                     for key in missing:
                         arg = cache_key_to_arg(key)
@@ -463,10 +469,10 @@ class _CacheContext:
     on a lower level.
     """
 
-    Cache = Union[DeferredCache, LruCache]
+    Cache = DeferredCache | LruCache
 
     _cache_context_objects: """WeakValueDictionary[
-        Tuple["_CacheContext.Cache", CacheKey], "_CacheContext"
+        tuple["_CacheContext.Cache", CacheKey], "_CacheContext"
     ]""" = WeakValueDictionary()
 
     def __init__(self, cache: "_CacheContext.Cache", cache_key: CacheKey) -> None:
@@ -500,13 +506,13 @@ class _CachedFunctionDescriptor:
     plugin."""
 
     max_entries: int
-    num_args: Optional[int]
-    uncached_args: Optional[Collection[str]]
+    num_args: int | None
+    uncached_args: Collection[str] | None
     tree: bool
     cache_context: bool
     iterable: bool
     prune_unread_entries: bool
-    name: Optional[str]
+    name: str | None
 
     def __call__(self, orig: F) -> CachedFunction[F]:
         d = DeferredCacheDescriptor(
@@ -526,13 +532,13 @@ class _CachedFunctionDescriptor:
 def cached(
     *,
     max_entries: int = 1000,
-    num_args: Optional[int] = None,
-    uncached_args: Optional[Collection[str]] = None,
+    num_args: int | None = None,
+    uncached_args: Collection[str] | None = None,
     tree: bool = False,
     cache_context: bool = False,
     iterable: bool = False,
     prune_unread_entries: bool = True,
-    name: Optional[str] = None,
+    name: str | None = None,
 ) -> _CachedFunctionDescriptor:
     return _CachedFunctionDescriptor(
         max_entries=max_entries,
@@ -553,8 +559,8 @@ class _CachedListFunctionDescriptor:
 
     cached_method_name: str
     list_name: str
-    num_args: Optional[int] = None
-    name: Optional[str] = None
+    num_args: int | None = None
+    name: str | None = None
 
     def __call__(self, orig: F) -> CachedFunction[F]:
         d = DeferredCacheListDescriptor(
@@ -571,8 +577,8 @@ def cachedList(
     *,
     cached_method_name: str,
     list_name: str,
-    num_args: Optional[int] = None,
-    name: Optional[str] = None,
+    num_args: int | None = None,
+    name: str | None = None,
 ) -> _CachedListFunctionDescriptor:
     """Creates a descriptor that wraps a function in a `DeferredCacheListDescriptor`.
 
diff --git a/synapse/util/caches/dictionary_cache.py b/synapse/util/caches/dictionary_cache.py
index 168ddc51cd..4289e327af 100644
--- a/synapse/util/caches/dictionary_cache.py
+++ b/synapse/util/caches/dictionary_cache.py
@@ -22,21 +22,17 @@ import enum
 import logging
 import threading
 from typing import (
-    Dict,
     Generic,
     Iterable,
     Literal,
-    Optional,
-    Set,
-    Tuple,
     TypeVar,
-    Union,
 )
 
 import attr
 
 from synapse.util.caches.lrucache import LruCache
 from synapse.util.caches.treecache import TreeCache
+from synapse.util.clock import Clock
 
 logger = logging.getLogger(__name__)
 
@@ -64,8 +60,8 @@ class DictionaryEntry(Generic[DKT, DV]):
     """
 
     full: bool
-    known_absent: Set[DKT]
-    value: Dict[DKT, DV]
+    known_absent: set[DKT]
+    value: dict[DKT, DV]
 
     def __len__(self) -> int:
         return len(self.value)
@@ -90,7 +86,7 @@ class _PerKeyValue(Generic[DV]):
 
     __slots__ = ["value"]
 
-    def __init__(self, value: Union[DV, Literal[_Sentinel.sentinel]]) -> None:
+    def __init__(self, value: DV | Literal[_Sentinel.sentinel]) -> None:
         self.value = value
 
     def __len__(self) -> int:
@@ -127,10 +123,13 @@ class DictionaryCache(Generic[KT, DKT, DV]):
     for the '2' dict key.
     """
 
-    def __init__(self, *, name: str, server_name: str, max_entries: int = 1000):
+    def __init__(
+        self, *, name: str, clock: Clock, server_name: str, max_entries: int = 1000
+    ):
         """
         Args:
             name
+            clock: The homeserver `Clock` instance
             server_name: The homeserver name that this cache is associated with
                 (used to label the metric) (`hs.hostname`).
             max_entries
@@ -156,10 +155,11 @@ class DictionaryCache(Generic[KT, DKT, DV]):
         #     * A key of `(KT, DKT)` has a value of `_PerKeyValue`
         #     * A key of `(KT, _FullCacheKey.KEY)` has a value of `Dict[DKT, DV]`
         self.cache: LruCache[
-            Tuple[KT, Union[DKT, Literal[_FullCacheKey.KEY]]],
-            Union[_PerKeyValue, Dict[DKT, DV]],
+            tuple[KT, DKT | Literal[_FullCacheKey.KEY]],
+            _PerKeyValue | dict[DKT, DV],
         ] = LruCache(
             max_size=max_entries,
+            clock=clock,
             server_name=server_name,
             cache_name=name,
             cache_type=TreeCache,
@@ -168,7 +168,7 @@ class DictionaryCache(Generic[KT, DKT, DV]):
 
         self.name = name
         self.sequence = 0
-        self.thread: Optional[threading.Thread] = None
+        self.thread: threading.Thread | None = None
 
     def check_thread(self) -> None:
         expected_thread = self.thread
@@ -180,9 +180,7 @@ class DictionaryCache(Generic[KT, DKT, DV]):
                     "Cache objects can only be accessed from the main thread"
                 )
 
-    def get(
-        self, key: KT, dict_keys: Optional[Iterable[DKT]] = None
-    ) -> DictionaryEntry:
+    def get(self, key: KT, dict_keys: Iterable[DKT] | None = None) -> DictionaryEntry:
         """Fetch an entry out of the cache
 
         Args:
@@ -292,8 +290,8 @@ class DictionaryCache(Generic[KT, DKT, DV]):
         self,
         sequence: int,
         key: KT,
-        value: Dict[DKT, DV],
-        fetched_keys: Optional[Iterable[DKT]] = None,
+        value: dict[DKT, DV],
+        fetched_keys: Iterable[DKT] | None = None,
     ) -> None:
         """Updates the entry in the cache.
 
@@ -327,7 +325,7 @@ class DictionaryCache(Generic[KT, DKT, DV]):
                 self._update_subset(key, value, fetched_keys)
 
     def _update_subset(
-        self, key: KT, value: Dict[DKT, DV], fetched_keys: Iterable[DKT]
+        self, key: KT, value: dict[DKT, DV], fetched_keys: Iterable[DKT]
     ) -> None:
         """Add the given dictionary values as explicit keys in the cache.
 
diff --git a/synapse/util/caches/expiringcache.py b/synapse/util/caches/expiringcache.py
index 305af5051c..528e4bb852 100644
--- a/synapse/util/caches/expiringcache.py
+++ b/synapse/util/caches/expiringcache.py
@@ -21,17 +21,27 @@
 
 import logging
 from collections import OrderedDict
-from typing import Any, Generic, Iterable, Literal, Optional, TypeVar, Union, overload
+from typing import (
+    TYPE_CHECKING,
+    Any,
+    Generic,
+    Iterable,
+    Literal,
+    TypeVar,
+    overload,
+)
 
 import attr
 
 from twisted.internet import defer
 
 from synapse.config import cache as cache_config
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.util.caches import EvictionReason, register_cache
 from synapse.util.clock import Clock
 
+if TYPE_CHECKING:
+    from synapse.server import HomeServer
+
 logger = logging.getLogger(__name__)
 
 
@@ -49,6 +59,7 @@ class ExpiringCache(Generic[KT, VT]):
         *,
         cache_name: str,
         server_name: str,
+        hs: "HomeServer",
         clock: Clock,
         max_len: int = 0,
         expiry_ms: int = 0,
@@ -99,9 +110,7 @@ class ExpiringCache(Generic[KT, VT]):
             return
 
         def f() -> "defer.Deferred[None]":
-            return run_as_background_process(
-                "prune_cache", server_name, self._prune_cache
-            )
+            return hs.run_as_background_process("prune_cache", self._prune_cache)
 
         self._clock.looping_call(f, self._expiry_ms / 2)
 
@@ -135,7 +144,7 @@ class ExpiringCache(Generic[KT, VT]):
 
         return entry.value
 
-    def pop(self, key: KT, default: T = SENTINEL) -> Union[VT, T]:
+    def pop(self, key: KT, default: T = SENTINEL) -> VT | T:
         """Removes and returns the value with the given key from the cache.
 
         If the key isn't in the cache then `default` will be returned if
@@ -162,12 +171,12 @@ class ExpiringCache(Generic[KT, VT]):
         return key in self._cache
 
     @overload
-    def get(self, key: KT, default: Literal[None] = None) -> Optional[VT]: ...
+    def get(self, key: KT, default: Literal[None] = None) -> VT | None: ...
 
     @overload
-    def get(self, key: KT, default: T) -> Union[VT, T]: ...
+    def get(self, key: KT, default: T) -> VT | T: ...
 
-    def get(self, key: KT, default: Optional[T] = None) -> Union[VT, Optional[T]]:
+    def get(self, key: KT, default: T | None = None) -> VT | T | None:
         try:
             return self[key]
         except KeyError:
diff --git a/synapse/util/caches/lrucache.py b/synapse/util/caches/lrucache.py
index 2d4cde19a5..d304e804e9 100644
--- a/synapse/util/caches/lrucache.py
+++ b/synapse/util/caches/lrucache.py
@@ -30,29 +30,18 @@ from typing import (
     Any,
     Callable,
     Collection,
-    Dict,
     Generic,
     Iterable,
-    List,
     Literal,
-    Optional,
-    Set,
-    Tuple,
-    Type,
     TypeVar,
-    Union,
     cast,
     overload,
 )
 
-from twisted.internet import defer, reactor
+from twisted.internet import defer
 
 from synapse.config import cache as cache_config
-from synapse.metrics.background_process_metrics import (
-    run_as_background_process,
-)
 from synapse.metrics.jemalloc import get_jemalloc_stats
-from synapse.types import ISynapseThreadlessReactor
 from synapse.util import caches
 from synapse.util.caches import CacheMetric, EvictionReason, register_cache
 from synapse.util.caches.treecache import (
@@ -123,16 +112,17 @@ GLOBAL_ROOT = ListNode["_Node"].create_root_node()
 
 def _expire_old_entries(
     server_name: str,
+    hs: "HomeServer",
     clock: Clock,
     expiry_seconds: float,
-    autotune_config: Optional[dict],
+    autotune_config: dict | None,
 ) -> "defer.Deferred[None]":
     """Walks the global cache list to find cache entries that haven't been
     accessed in the given number of seconds, or if a given memory threshold has been breached.
     """
 
     async def _internal_expire_old_entries(
-        clock: Clock, expiry_seconds: float, autotune_config: Optional[dict]
+        clock: Clock, expiry_seconds: float, autotune_config: dict | None
     ) -> None:
         if autotune_config:
             max_cache_memory_usage = autotune_config["max_cache_memory_usage"]
@@ -228,9 +218,8 @@ def _expire_old_entries(
 
         logger.info("Dropped %d items from caches", i)
 
-    return run_as_background_process(
+    return hs.run_as_background_process(
         "LruCache._expire_old_entries",
-        server_name,
         _internal_expire_old_entries,
         clock,
         expiry_seconds,
@@ -261,6 +250,7 @@ def setup_expire_lru_cache_entries(hs: "HomeServer") -> None:
         _expire_old_entries,
         30 * 1000,
         server_name,
+        hs,
         clock,
         expiry_time,
         hs.config.caches.cache_autotuning,
@@ -289,7 +279,7 @@ class _Node(Generic[KT, VT]):
         prune_unread_entries: bool = True,
     ):
         self._list_node = ListNode.insert_after(self, root)
-        self._global_list_node: Optional[_TimedListNode] = None
+        self._global_list_node: _TimedListNode | None = None
         if USE_GLOBAL_LIST and prune_unread_entries:
             self._global_list_node = _TimedListNode.insert_after(self, GLOBAL_ROOT)
             self._global_list_node.update_last_access(clock)
@@ -311,7 +301,7 @@ class _Node(Generic[KT, VT]):
         # footprint down. Storing `None` is free as its a singleton, while empty
         # lists are 56 bytes (and empty sets are 216 bytes, if we did the naive
         # thing and used sets).
-        self.callbacks: Optional[List[Callable[[], None]]] = None
+        self.callbacks: list[Callable[[], None]] | None = None
 
         self.add_callbacks(callbacks)
 
@@ -404,15 +394,15 @@ class LruCache(Generic[KT, VT]):
         self,
         *,
         max_size: int,
+        clock: Clock,
         server_name: str,
         cache_name: str,
-        cache_type: Type[Union[dict, TreeCache]] = dict,
-        size_callback: Optional[Callable[[VT], int]] = None,
-        metrics_collection_callback: Optional[Callable[[], None]] = None,
+        cache_type: type[dict | TreeCache] = dict,
+        size_callback: Callable[[VT], int] | None = None,
+        metrics_collection_callback: Callable[[], None] | None = None,
         apply_cache_factor_from_config: bool = True,
-        clock: Optional[Clock] = None,
         prune_unread_entries: bool = True,
-        extra_index_cb: Optional[Callable[[KT, VT], KT]] = None,
+        extra_index_cb: Callable[[KT, VT], KT] | None = None,
     ): ...
 
     @overload
@@ -420,30 +410,30 @@ class LruCache(Generic[KT, VT]):
         self,
         *,
         max_size: int,
+        clock: Clock,
         server_name: str,
         cache_name: Literal[None] = None,
-        cache_type: Type[Union[dict, TreeCache]] = dict,
-        size_callback: Optional[Callable[[VT], int]] = None,
-        metrics_collection_callback: Optional[Callable[[], None]] = None,
+        cache_type: type[dict | TreeCache] = dict,
+        size_callback: Callable[[VT], int] | None = None,
+        metrics_collection_callback: Callable[[], None] | None = None,
         apply_cache_factor_from_config: bool = True,
-        clock: Optional[Clock] = None,
         prune_unread_entries: bool = True,
-        extra_index_cb: Optional[Callable[[KT, VT], KT]] = None,
+        extra_index_cb: Callable[[KT, VT], KT] | None = None,
     ): ...
 
     def __init__(
         self,
         *,
         max_size: int,
+        clock: Clock,
         server_name: str,
-        cache_name: Optional[str] = None,
-        cache_type: Type[Union[dict, TreeCache]] = dict,
-        size_callback: Optional[Callable[[VT], int]] = None,
-        metrics_collection_callback: Optional[Callable[[], None]] = None,
+        cache_name: str | None = None,
+        cache_type: type[dict | TreeCache] = dict,
+        size_callback: Callable[[VT], int] | None = None,
+        metrics_collection_callback: Callable[[], None] | None = None,
         apply_cache_factor_from_config: bool = True,
-        clock: Optional[Clock] = None,
         prune_unread_entries: bool = True,
-        extra_index_cb: Optional[Callable[[KT, VT], KT]] = None,
+        extra_index_cb: Callable[[KT, VT], KT] | None = None,
     ):
         """
         Args:
@@ -492,16 +482,7 @@ class LruCache(Generic[KT, VT]):
 
                 Note: The new key does not have to be unique.
         """
-        # Default `clock` to something sensible. Note that we rename it to
-        # `real_clock` so that mypy doesn't think its still `Optional`.
-        if clock is None:
-            real_clock = Clock(
-                cast(ISynapseThreadlessReactor, reactor), server_name=server_name
-            )
-        else:
-            real_clock = clock
-
-        cache: Union[Dict[KT, _Node[KT, VT]], TreeCache] = cache_type()
+        cache: dict[KT, _Node[KT, VT]] | TreeCache = cache_type()
         self.cache = cache  # Used for introspection.
         self.apply_cache_factor_from_config = apply_cache_factor_from_config
 
@@ -517,10 +498,10 @@ class LruCache(Generic[KT, VT]):
 
         # register_cache might call our "set_cache_factor" callback; there's nothing to
         # do yet when we get resized.
-        self._on_resize: Optional[Callable[[], None]] = None
+        self._on_resize: Callable[[], None] | None = None
 
         if cache_name is not None and server_name is not None:
-            metrics: Optional[CacheMetric] = register_cache(
+            metrics: CacheMetric | None = register_cache(
                 cache_type="lru_cache",
                 cache_name=cache_name,
                 cache=self,
@@ -541,7 +522,7 @@ class LruCache(Generic[KT, VT]):
 
         lock = threading.Lock()
 
-        extra_index: Dict[KT, Set[KT]] = {}
+        extra_index: dict[KT, set[KT]] = {}
 
         def evict() -> None:
             while cache_len() > self.max_size:
@@ -592,7 +573,7 @@ class LruCache(Generic[KT, VT]):
                 key,
                 value,
                 weak_ref_to_self,
-                real_clock,
+                clock,
                 callbacks,
                 prune_unread_entries,
             )
@@ -610,7 +591,7 @@ class LruCache(Generic[KT, VT]):
                 metrics.inc_memory_usage(node.memory)
 
         def move_node_to_front(node: _Node[KT, VT]) -> None:
-            node.move_to_front(real_clock, list_root)
+            node.move_to_front(clock, list_root)
 
         def delete_node(node: _Node[KT, VT]) -> int:
             node.drop_from_lists()
@@ -642,7 +623,7 @@ class LruCache(Generic[KT, VT]):
             callbacks: Collection[Callable[[], None]] = ...,
             update_metrics: bool = ...,
             update_last_access: bool = ...,
-        ) -> Optional[VT]: ...
+        ) -> VT | None: ...
 
         @overload
         def cache_get(
@@ -651,16 +632,16 @@ class LruCache(Generic[KT, VT]):
             callbacks: Collection[Callable[[], None]] = ...,
             update_metrics: bool = ...,
             update_last_access: bool = ...,
-        ) -> Union[T, VT]: ...
+        ) -> T | VT: ...
 
         @synchronized
         def cache_get(
             key: KT,
-            default: Optional[T] = None,
+            default: T | None = None,
             callbacks: Collection[Callable[[], None]] = (),
             update_metrics: bool = True,
             update_last_access: bool = True,
-        ) -> Union[None, T, VT]:
+        ) -> None | T | VT:
             """Look up a key in the cache
 
             Args:
@@ -694,21 +675,21 @@ class LruCache(Generic[KT, VT]):
             key: tuple,
             default: Literal[None] = None,
             update_metrics: bool = True,
-        ) -> Union[None, Iterable[Tuple[KT, VT]]]: ...
+        ) -> None | Iterable[tuple[KT, VT]]: ...
 
         @overload
         def cache_get_multi(
             key: tuple,
             default: T,
             update_metrics: bool = True,
-        ) -> Union[T, Iterable[Tuple[KT, VT]]]: ...
+        ) -> T | Iterable[tuple[KT, VT]]: ...
 
         @synchronized
         def cache_get_multi(
             key: tuple,
-            default: Optional[T] = None,
+            default: T | None = None,
             update_metrics: bool = True,
-        ) -> Union[None, T, Iterable[Tuple[KT, VT]]]:
+        ) -> None | T | Iterable[tuple[KT, VT]]:
             """Returns a generator yielding all entries under the given key.
 
             Can only be used if backed by a tree cache.
@@ -786,13 +767,13 @@ class LruCache(Generic[KT, VT]):
                 return value
 
         @overload
-        def cache_pop(key: KT, default: Literal[None] = None) -> Optional[VT]: ...
+        def cache_pop(key: KT, default: Literal[None] = None) -> VT | None: ...
 
         @overload
-        def cache_pop(key: KT, default: T) -> Union[T, VT]: ...
+        def cache_pop(key: KT, default: T) -> T | VT: ...
 
         @synchronized
-        def cache_pop(key: KT, default: Optional[T] = None) -> Union[None, T, VT]:
+        def cache_pop(key: KT, default: T | None = None) -> None | T | VT:
             node = cache.get(key, None)
             if node:
                 evicted_len = delete_node(node)
@@ -942,22 +923,22 @@ class AsyncLruCache(Generic[KT, VT]):
         self._lru_cache: LruCache[KT, VT] = LruCache(*args, **kwargs)
 
     async def get(
-        self, key: KT, default: Optional[T] = None, update_metrics: bool = True
-    ) -> Optional[VT]:
+        self, key: KT, default: T | None = None, update_metrics: bool = True
+    ) -> VT | None:
         return self._lru_cache.get(key, update_metrics=update_metrics)
 
     async def get_external(
         self,
         key: KT,
-        default: Optional[T] = None,
+        default: T | None = None,
         update_metrics: bool = True,
-    ) -> Optional[VT]:
+    ) -> VT | None:
         # This method should fetch from any configured external cache, in this case noop.
         return None
 
     def get_local(
-        self, key: KT, default: Optional[T] = None, update_metrics: bool = True
-    ) -> Optional[VT]:
+        self, key: KT, default: T | None = None, update_metrics: bool = True
+    ) -> VT | None:
         return self._lru_cache.get(key, update_metrics=update_metrics)
 
     async def set(self, key: KT, value: VT) -> None:
diff --git a/synapse/util/caches/response_cache.py b/synapse/util/caches/response_cache.py
index 79e34262df..b1cdc81dda 100644
--- a/synapse/util/caches/response_cache.py
+++ b/synapse/util/caches/response_cache.py
@@ -24,10 +24,8 @@ from typing import (
     Any,
     Awaitable,
     Callable,
-    Dict,
     Generic,
     Iterable,
-    Optional,
     TypeVar,
 )
 
@@ -89,7 +87,7 @@ class ResponseCacheEntry:
     easier to cache Failure results.
     """
 
-    opentracing_span_context: "Optional[opentracing.SpanContext]"
+    opentracing_span_context: "opentracing.SpanContext | None"
     """The opentracing span which generated/is generating the result"""
 
 
@@ -119,7 +117,7 @@ class ResponseCache(Generic[KV]):
             timeout_ms
             enable_logging
         """
-        self._result_cache: Dict[KV, ResponseCacheEntry] = {}
+        self._result_cache: dict[KV, ResponseCacheEntry] = {}
 
         self.clock = clock
         self.timeout_sec = timeout_ms / 1000.0
@@ -151,7 +149,7 @@ class ResponseCache(Generic[KV]):
         """
         return self._result_cache.keys()
 
-    def _get(self, key: KV) -> Optional[ResponseCacheEntry]:
+    def _get(self, key: KV) -> ResponseCacheEntry | None:
         """Look up the given key.
 
         Args:
@@ -172,7 +170,7 @@ class ResponseCache(Generic[KV]):
         self,
         context: ResponseCacheContext[KV],
         deferred: "defer.Deferred[RV]",
-        opentracing_span_context: "Optional[opentracing.SpanContext]",
+        opentracing_span_context: "opentracing.SpanContext | None",
     ) -> ResponseCacheEntry:
         """Set the entry for the given key to the given deferred.
 
@@ -198,7 +196,17 @@ class ResponseCache(Generic[KV]):
             # the should_cache bit, we leave it in the cache for now and schedule
             # its removal later.
             if self.timeout_sec and context.should_cache:
-                self.clock.call_later(self.timeout_sec, self._entry_timeout, key)
+                self.clock.call_later(
+                    self.timeout_sec,
+                    self._entry_timeout,
+                    key,
+                    # We don't need to track these calls since they don't hold any strong
+                    # references which would keep the `HomeServer` in memory after shutdown.
+                    # We don't want to track these because they can get cancelled really
+                    # quickly and thrash the tracking mechanism, ie. during repeated calls
+                    # to /sync.
+                    call_later_cancel_on_shutdown=False,
+                )
             else:
                 # otherwise, remove the result immediately.
                 self.unset(key)
@@ -280,7 +288,7 @@ class ResponseCache(Generic[KV]):
             if cache_context:
                 kwargs["cache_context"] = context
 
-            span_context: Optional[opentracing.SpanContext] = None
+            span_context: opentracing.SpanContext | None = None
 
             async def cb() -> RV:
                 # NB it is important that we do not `await` before setting span_context!
diff --git a/synapse/util/caches/stream_change_cache.py b/synapse/util/caches/stream_change_cache.py
index 2cffd352d8..7c6c9bc572 100644
--- a/synapse/util/caches/stream_change_cache.py
+++ b/synapse/util/caches/stream_change_cache.py
@@ -21,7 +21,7 @@
 
 import logging
 import math
-from typing import Collection, Dict, FrozenSet, List, Mapping, Optional, Set, Union
+from typing import Collection, Mapping
 
 import attr
 from sortedcontainers import SortedDict
@@ -45,14 +45,14 @@ class AllEntitiesChangedResult:
     that callers do the correct checks.
     """
 
-    _entities: Optional[List[EntityType]]
+    _entities: list[EntityType] | None
 
     @property
     def hit(self) -> bool:
         return self._entities is not None
 
     @property
-    def entities(self) -> List[EntityType]:
+    def entities(self) -> list[EntityType]:
         assert self._entities is not None
         return self._entities
 
@@ -78,7 +78,7 @@ class StreamChangeCache:
         server_name: str,
         current_stream_pos: int,
         max_size: int = 10000,
-        prefilled_cache: Optional[Mapping[EntityType, int]] = None,
+        prefilled_cache: Mapping[EntityType, int] | None = None,
     ) -> None:
         """
         Args:
@@ -94,11 +94,11 @@ class StreamChangeCache:
         self._max_size = math.floor(max_size)
 
         # map from stream id to the set of entities which changed at that stream id.
-        self._cache: SortedDict[int, Set[EntityType]] = SortedDict()
+        self._cache: SortedDict[int, set[EntityType]] = SortedDict()
         # map from entity to the stream ID of the latest change for that entity.
         #
         # Must be kept in sync with _cache.
-        self._entity_to_key: Dict[EntityType, int] = {}
+        self._entity_to_key: dict[EntityType, int] = {}
 
         # the earliest stream_pos for which we can reliably answer
         # get_all_entities_changed. In other words, one less than the earliest
@@ -182,7 +182,7 @@ class StreamChangeCache:
 
     def get_entities_changed(
         self, entities: Collection[EntityType], stream_pos: int, _perf_factor: int = 1
-    ) -> Union[Set[EntityType], FrozenSet[EntityType]]:
+    ) -> set[EntityType] | frozenset[EntityType]:
         """
         Returns the subset of the given entities that have had changes after the given position.
 
@@ -291,7 +291,7 @@ class StreamChangeCache:
         if stream_pos < self._earliest_known_stream_pos:
             return AllEntitiesChangedResult(None)
 
-        changed_entities: List[EntityType] = []
+        changed_entities: list[EntityType] = []
 
         for k in self._cache.islice(start=self._cache.bisect_right(stream_pos)):
             changed_entities.extend(self._cache[k])
@@ -352,7 +352,7 @@ class StreamChangeCache:
             for entity in r:
                 self._entity_to_key.pop(entity, None)
 
-    def get_max_pos_of_last_change(self, entity: EntityType) -> Optional[int]:
+    def get_max_pos_of_last_change(self, entity: EntityType) -> int | None:
         """Returns an upper bound of the stream id of the last change to an
         entity.
 
diff --git a/synapse/util/caches/ttlcache.py b/synapse/util/caches/ttlcache.py
index 18c3a1e51c..25b87832d8 100644
--- a/synapse/util/caches/ttlcache.py
+++ b/synapse/util/caches/ttlcache.py
@@ -21,7 +21,7 @@
 
 import logging
 import time
-from typing import Any, Callable, Dict, Generic, Tuple, TypeVar, Union
+from typing import Any, Callable, Generic, TypeVar
 
 import attr
 from sortedcontainers import SortedList
@@ -56,7 +56,7 @@ class TTLCache(Generic[KT, VT]):
         """
 
         # map from key to _CacheEntry
-        self._data: Dict[KT, _CacheEntry[KT, VT]] = {}
+        self._data: dict[KT, _CacheEntry[KT, VT]] = {}
 
         # the _CacheEntries, sorted by expiry time
         self._expiry_list: SortedList[_CacheEntry[KT, VT]] = SortedList()
@@ -91,7 +91,7 @@ class TTLCache(Generic[KT, VT]):
         self._data[key] = entry
         self._expiry_list.add(entry)
 
-    def get(self, key: KT, default: T = SENTINEL) -> Union[VT, T]:
+    def get(self, key: KT, default: T = SENTINEL) -> VT | T:
         """Get a value from the cache
 
         Args:
@@ -113,7 +113,7 @@ class TTLCache(Generic[KT, VT]):
         self._metrics.inc_hits()
         return e.value
 
-    def get_with_expiry(self, key: KT) -> Tuple[VT, float, float]:
+    def get_with_expiry(self, key: KT) -> tuple[VT, float, float]:
         """Get a value, and its expiry time, from the cache
 
         Args:
@@ -134,7 +134,7 @@ class TTLCache(Generic[KT, VT]):
         self._metrics.inc_hits()
         return e.value, e.expiry_time, e.ttl
 
-    def pop(self, key: KT, default: T = SENTINEL) -> Union[VT, T]:
+    def pop(self, key: KT, default: T = SENTINEL) -> VT | T:
         """Remove a value from the cache
 
         If key is in the cache, remove it and return its value, else return default.
diff --git a/synapse/util/check_dependencies.py b/synapse/util/check_dependencies.py
index 1c79c0be48..7e92b55592 100644
--- a/synapse/util/check_dependencies.py
+++ b/synapse/util/check_dependencies.py
@@ -28,8 +28,9 @@ require. But this is probably just symptomatic of Python's package management.
 
 import logging
 from importlib import metadata
-from typing import Iterable, NamedTuple, Optional
+from typing import Any, Iterable, NamedTuple, Sequence, cast
 
+from packaging.markers import Marker, Value, Variable, default_environment
 from packaging.requirements import Requirement
 
 DISTRIBUTION_NAME = "matrix-synapse"
@@ -65,9 +66,23 @@ RUNTIME_EXTRAS = set(ALL_EXTRAS) - DEV_EXTRAS
 VERSION = metadata.version(DISTRIBUTION_NAME)
 
 
+def _marker_environment(extra: str) -> dict[str, str]:
+    """Return the marker environment for `extra`, seeded with the current interpreter."""
+
+    env = cast(dict[str, str], dict(default_environment()))
+    env["extra"] = extra
+    return env
+
+
 def _is_dev_dependency(req: Requirement) -> bool:
-    return req.marker is not None and any(
-        req.marker.evaluate({"extra": e}) for e in DEV_EXTRAS
+    """Return True if `req` is a development dependency."""
+    if req.marker is None:
+        return False
+
+    marker_extras = _extras_from_marker(req.marker)
+    return any(
+        extra in DEV_EXTRAS and req.marker.evaluate(_marker_environment(extra))
+        for extra in marker_extras
     )
 
 
@@ -95,6 +110,7 @@ def _generic_dependencies() -> Iterable[Dependency]:
     """Yield pairs (requirement, must_be_installed)."""
     requirements = metadata.requires(DISTRIBUTION_NAME)
     assert requirements is not None
+    env_no_extra = _marker_environment("")
     for raw_requirement in requirements:
         req = Requirement(raw_requirement)
         if _is_dev_dependency(req) or _should_ignore_runtime_requirement(req):
@@ -103,7 +119,7 @@ def _generic_dependencies() -> Iterable[Dependency]:
         # https://packaging.pypa.io/en/latest/markers.html#usage notes that
         #   > Evaluating an extra marker with no environment is an error
         # so we pass in a dummy empty extra value here.
-        must_be_installed = req.marker is None or req.marker.evaluate({"extra": ""})
+        must_be_installed = req.marker is None or req.marker.evaluate(env_no_extra)
         yield Dependency(req, must_be_installed)
 
 
@@ -111,6 +127,8 @@ def _dependencies_for_extra(extra: str) -> Iterable[Dependency]:
     """Yield additional dependencies needed for a given `extra`."""
     requirements = metadata.requires(DISTRIBUTION_NAME)
     assert requirements is not None
+    env_no_extra = _marker_environment("")
+    env_for_extra = _marker_environment(extra)
     for raw_requirement in requirements:
         req = Requirement(raw_requirement)
         if _is_dev_dependency(req):
@@ -118,13 +136,85 @@ def _dependencies_for_extra(extra: str) -> Iterable[Dependency]:
         # Exclude mandatory deps by only selecting deps needed with this extra.
         if (
             req.marker is not None
-            and req.marker.evaluate({"extra": extra})
-            and not req.marker.evaluate({"extra": ""})
+            and req.marker.evaluate(env_for_extra)
+            and not req.marker.evaluate(env_no_extra)
         ):
             yield Dependency(req, True)
 
 
-def _not_installed(requirement: Requirement, extra: Optional[str] = None) -> str:
+def _values_from_marker_value(value: Value) -> set[str]:
+    """Extract text values contained in a marker `Value`."""
+
+    raw: Any = value.value
+    if isinstance(raw, str):
+        return {raw}
+    if isinstance(raw, (tuple, list)):
+        return {str(item) for item in raw}
+    return {str(raw)}
+
+
+def _extras_from_marker(marker: Marker | None) -> set[str]:
+    """Return every `extra` referenced in the supplied marker tree."""
+
+    extras: set[str] = set()
+
+    if marker is None:
+        return extras
+
+    def collect(tree: object) -> None:
+        if isinstance(tree, list):
+            for item in tree:
+                collect(item)
+        elif isinstance(tree, tuple) and len(tree) == 3:
+            lhs, _op, rhs = tree
+            if (
+                isinstance(lhs, Variable)
+                and lhs.value == "extra"
+                and isinstance(rhs, Value)
+            ):
+                extras.update(_values_from_marker_value(rhs))
+            elif (
+                isinstance(rhs, Variable)
+                and rhs.value == "extra"
+                and isinstance(lhs, Value)
+            ):
+                extras.update(_values_from_marker_value(lhs))
+
+    collect(marker._markers)
+    return extras
+
+
+def _extras_to_consider_for_requirement(
+    marker: Marker, base_candidates: Sequence[str]
+) -> set[str]:
+    """
+    Augment `base_candidates` with extras explicitly mentioned in `marker`.
+
+    Markers can mention extras (e.g. `extra == "saml2"`).
+    """
+
+    # Avoid modifying the input sequence.
+    # Use a set to efficiently avoid duplicate extras.
+    extras = set(base_candidates)
+
+    for candidate in _extras_from_marker(marker):
+        extras.add(candidate)
+
+    return extras
+
+
+def _marker_applies_for_any_extra(requirement: Requirement, extras: set[str]) -> bool:
+    """Check whether a requirement's marker matches any evaluated `extra`."""
+
+    if requirement.marker is None:
+        return True
+
+    return any(
+        requirement.marker.evaluate(_marker_environment(extra)) for extra in extras
+    )
+
+
+def _not_installed(requirement: Requirement, extra: str | None = None) -> str:
     if extra:
         return (
             f"Synapse {VERSION} needs {requirement.name} for {extra}, "
@@ -135,7 +225,7 @@ def _not_installed(requirement: Requirement, extra: Optional[str] = None) -> str
 
 
 def _incorrect_version(
-    requirement: Requirement, got: str, extra: Optional[str] = None
+    requirement: Requirement, got: str, extra: str | None = None
 ) -> str:
     if extra:
         return (
@@ -148,7 +238,7 @@ def _incorrect_version(
         )
 
 
-def _no_reported_version(requirement: Requirement, extra: Optional[str] = None) -> str:
+def _no_reported_version(requirement: Requirement, extra: str | None = None) -> str:
     if extra:
         return (
             f"Synapse {VERSION} needs {requirement} for {extra}, "
@@ -161,10 +251,10 @@ def _no_reported_version(requirement: Requirement, extra: Optional[str] = None)
         )
 
 
-def check_requirements(extra: Optional[str] = None) -> None:
+def check_requirements(extra: str | None = None) -> None:
     """Check Synapse's dependencies are present and correctly versioned.
 
-    If provided, `extra` must be the name of an pacakging extra (e.g. "saml2" in
+    If provided, `extra` must be the name of an packaging extra (e.g. "saml2" in
     `pip install matrix-synapse[saml2]`).
 
     If `extra` is None, this function checks that
@@ -174,6 +264,15 @@ def check_requirements(extra: Optional[str] = None) -> None:
     If `extra` is not None, this function checks that
     - the dependencies needed for that extra are installed and correctly versioned.
 
+    `marker`s are optional attributes on each requirement which specify
+    conditions under which the requirement applies. For example, a requirement
+    might only be needed on Windows, or with Python < 3.14. Markers can
+    additionally mention `extras` themselves, meaning a requirement may not
+    apply if the marker mentions an extra that the user has not asked for.
+
+    This function skips a requirement when its markers do not apply in the
+    current environment.
+
     :raises DependencyException: if a dependency is missing or incorrectly versioned.
     :raises ValueError: if this extra does not exist.
     """
@@ -188,7 +287,25 @@ def check_requirements(extra: Optional[str] = None) -> None:
     deps_unfulfilled = []
     errors = []
 
+    if extra is None:
+        # Default to all mandatory dependencies (non-dev extras).
+        # "" means all dependencies that aren't conditional on an extra.
+        base_extra_candidates: Sequence[str] = ("", *RUNTIME_EXTRAS)
+    else:
+        base_extra_candidates = (extra,)
+
     for requirement, must_be_installed in dependencies:
+        if requirement.marker is not None:
+            candidate_extras = _extras_to_consider_for_requirement(
+                requirement.marker, base_extra_candidates
+            )
+            # Skip checking this dependency if the requirement's marker object
+            # (i.e. `python_version < "3.14" and os_name == "win32"`) does not
+            # apply for any of the extras we're considering.
+            if not _marker_applies_for_any_extra(requirement, candidate_extras):
+                continue
+
+        # Check if the requirement is installed and correctly versioned.
         try:
             dist: metadata.Distribution = metadata.distribution(requirement.name)
         except metadata.PackageNotFoundError:
diff --git a/synapse/util/clock.py b/synapse/util/clock.py
index e85af17005..5b59cef60a 100644
--- a/synapse/util/clock.py
+++ b/synapse/util/clock.py
@@ -19,8 +19,8 @@ from typing import (
     Callable,
 )
 
-import attr
 from typing_extensions import ParamSpec
+from zope.interface import implementer
 
 from twisted.internet import defer, task
 from twisted.internet.defer import Deferred
@@ -34,24 +34,54 @@ from synapse.util import log_failure
 P = ParamSpec("P")
 
 
-@attr.s(slots=True)
 class Clock:
     """
     A Clock wraps a Twisted reactor and provides utilities on top of it.
 
+    This clock should be used in place of calls to the base reactor wherever `LoopingCall`
+    or `DelayedCall` are made (such as when calling `reactor.callLater`. This is to
+    ensure the calls made by this `HomeServer` instance are tracked and can be cleaned
+    up during `HomeServer.shutdown()`.
+
+    We enforce usage of this clock instead of using the reactor directly via lints in
+    `scripts-dev/mypy_synapse_plugin.py`.
+
+
     Args:
         reactor: The Twisted reactor to use.
     """
 
-    _reactor: ISynapseThreadlessReactor = attr.ib()
-    _server_name: str = attr.ib()
+    _reactor: ISynapseThreadlessReactor
+
+    def __init__(self, reactor: ISynapseThreadlessReactor, server_name: str) -> None:
+        self._reactor = reactor
+        self._server_name = server_name
+
+        self._delayed_call_id: int = 0
+        """Unique ID used to track delayed calls"""
+
+        self._looping_calls: list[LoopingCall] = []
+        """List of active looping calls"""
+
+        self._call_id_to_delayed_call: dict[int, IDelayedCall] = {}
+        """Mapping from unique call ID to delayed call"""
+
+        self._is_shutdown = False
+        """Whether shutdown has been requested by the HomeServer"""
+
+    def shutdown(self) -> None:
+        self._is_shutdown = True
+        self.cancel_all_looping_calls()
+        self.cancel_all_delayed_calls()
 
     async def sleep(self, seconds: float) -> None:
         d: defer.Deferred[float] = defer.Deferred()
         # Start task in the `sentinel` logcontext, to avoid leaking the current context
         # into the reactor once it finishes.
         with context.PreserveLoggingContext():
-            self._reactor.callLater(seconds, d.callback, seconds)
+            # We can ignore the lint here since this class is the one location callLater should
+            # be called.
+            self._reactor.callLater(seconds, d.callback, seconds)  # type: ignore[call-later-not-tracked]
             await d
 
     def time(self) -> float:
@@ -124,6 +154,9 @@ class Clock:
     ) -> LoopingCall:
         """Common functionality for `looping_call` and `looping_call_now`"""
 
+        if self._is_shutdown:
+            raise Exception("Cannot start looping call. Clock has been shutdown")
+
         def wrapped_f(*args: P.args, **kwargs: P.kwargs) -> Deferred:
             assert context.current_context() is context.SENTINEL_CONTEXT, (
                 "Expected `looping_call` callback from the reactor to start with the sentinel logcontext "
@@ -155,7 +188,9 @@ class Clock:
                 # logcontext to the reactor
                 return context.run_in_background(f, *args, **kwargs)
 
-        call = task.LoopingCall(wrapped_f, *args, **kwargs)
+        # We can ignore the lint here since this is the one location LoopingCall's
+        # should be created.
+        call = task.LoopingCall(wrapped_f, *args, **kwargs)  # type: ignore[prefer-synapse-clock-looping-call]
         call.clock = self._reactor
         # If `now=true`, the function will be called here immediately so we need to be
         # in the sentinel context now.
@@ -165,10 +200,32 @@ class Clock:
         with context.PreserveLoggingContext():
             d = call.start(msec / 1000.0, now=now)
         d.addErrback(log_failure, "Looping call died", consumeErrors=False)
+        self._looping_calls.append(call)
         return call
 
+    def cancel_all_looping_calls(self, consumeErrors: bool = True) -> None:
+        """
+        Stop all running looping calls.
+
+        Args:
+            consumeErrors: Whether to re-raise errors encountered when cancelling the
+            scheduled call.
+        """
+        for call in self._looping_calls:
+            try:
+                call.stop()
+            except Exception:
+                if not consumeErrors:
+                    raise
+        self._looping_calls.clear()
+
     def call_later(
-        self, delay: float, callback: Callable, *args: Any, **kwargs: Any
+        self,
+        delay: float,
+        callback: Callable,
+        *args: Any,
+        call_later_cancel_on_shutdown: bool = True,
+        **kwargs: Any,
     ) -> IDelayedCall:
         """Call something later
 
@@ -180,39 +237,78 @@ class Clock:
             delay: How long to wait in seconds.
             callback: Function to call
             *args: Postional arguments to pass to function.
+            call_later_cancel_on_shutdown: Whether this call should be tracked for cleanup during
+                shutdown. In general, all calls should be tracked. There may be a use case
+                not to track calls with a `timeout` of 0 (or similarly short) since tracking
+                them may result in rapid insertions and removals of tracked calls
+                unnecessarily. But unless a specific instance of tracking proves to be an
+                issue, we can just track all delayed calls.
             **kwargs: Key arguments to pass to function.
         """
 
-        def wrapped_callback(*args: Any, **kwargs: Any) -> None:
-            assert context.current_context() is context.SENTINEL_CONTEXT, (
-                "Expected `call_later` callback from the reactor to start with the sentinel logcontext "
-                f"but saw {context.current_context()}. In other words, another task shouldn't have "
-                "leaked their logcontext to us."
-            )
+        if self._is_shutdown:
+            raise Exception("Cannot start delayed call. Clock has been shutdown")
 
-            # Because this is a callback from the reactor, we will be using the
-            # `sentinel` log context at this point. We want the function to log with
-            # some logcontext as we want to know which server the logs came from.
-            #
-            # We use `PreserveLoggingContext` to prevent our new `call_later`
-            # logcontext from finishing as soon as we exit this function, in case `f`
-            # returns an awaitable/deferred which would continue running and may try to
-            # restore the `loop_call` context when it's done (because it's trying to
-            # adhere to the Synapse logcontext rules.)
-            #
-            # This also ensures that we return to the `sentinel` context when we exit
-            # this function and yield control back to the reactor to avoid leaking the
-            # current logcontext to the reactor (which would then get picked up and
-            # associated with the next thing the reactor does)
-            with context.PreserveLoggingContext(
-                context.LoggingContext(name="call_later", server_name=self._server_name)
-            ):
-                # We use `run_in_background` to reset the logcontext after `f` (or the
-                # awaitable returned by `f`) completes to avoid leaking the current
-                # logcontext to the reactor
-                context.run_in_background(callback, *args, **kwargs)
+        def create_wrapped_callback(
+            track_for_shutdown_cancellation: bool,
+        ) -> Callable[P, None]:
+            def wrapped_callback(*args: Any, **kwargs: Any) -> None:
+                assert context.current_context() is context.SENTINEL_CONTEXT, (
+                    "Expected `call_later` callback from the reactor to start with the sentinel logcontext "
+                    f"but saw {context.current_context()}. In other words, another task shouldn't have "
+                    "leaked their logcontext to us."
+                )
 
-        return self._reactor.callLater(delay, wrapped_callback, *args, **kwargs)
+                # Because this is a callback from the reactor, we will be using the
+                # `sentinel` log context at this point. We want the function to log with
+                # some logcontext as we want to know which server the logs came from.
+                #
+                # We use `PreserveLoggingContext` to prevent our new `call_later`
+                # logcontext from finishing as soon as we exit this function, in case `f`
+                # returns an awaitable/deferred which would continue running and may try to
+                # restore the `call_later` context when it's done (because it's trying to
+                # adhere to the Synapse logcontext rules.)
+                #
+                # This also ensures that we return to the `sentinel` context when we exit
+                # this function and yield control back to the reactor to avoid leaking the
+                # current logcontext to the reactor (which would then get picked up and
+                # associated with the next thing the reactor does)
+                try:
+                    with context.PreserveLoggingContext(
+                        context.LoggingContext(
+                            name="call_later", server_name=self._server_name
+                        )
+                    ):
+                        # We use `run_in_background` to reset the logcontext after `f` (or the
+                        # awaitable returned by `f`) completes to avoid leaking the current
+                        # logcontext to the reactor
+                        context.run_in_background(callback, *args, **kwargs)
+                finally:
+                    if track_for_shutdown_cancellation:
+                        # We still want to remove the call from the tracking map. Even if
+                        # the callback raises an exception.
+                        self._call_id_to_delayed_call.pop(call_id)
+
+            return wrapped_callback
+
+        if call_later_cancel_on_shutdown:
+            call_id = self._delayed_call_id
+            self._delayed_call_id = self._delayed_call_id + 1
+
+            # We can ignore the lint here since this class is the one location callLater
+            # should be called.
+            call = self._reactor.callLater(
+                delay, create_wrapped_callback(True), *args, **kwargs
+            )  # type: ignore[call-later-not-tracked]
+            call = DelayedCallWrapper(call, call_id, self)
+            self._call_id_to_delayed_call[call_id] = call
+            return call
+        else:
+            # We can ignore the lint here since this class is the one location callLater should
+            # be called.
+            return self._reactor.callLater(
+                delay, create_wrapped_callback(False), *args, **kwargs
+            )  # type: ignore[call-later-not-tracked]
 
     def cancel_call_later(self, timer: IDelayedCall, ignore_errs: bool = False) -> None:
         try:
@@ -221,6 +317,24 @@ class Clock:
             if not ignore_errs:
                 raise
 
+    def cancel_all_delayed_calls(self, ignore_errs: bool = True) -> None:
+        """
+        Stop all scheduled calls that were marked with `cancel_on_shutdown` when they were created.
+
+        Args:
+            ignore_errs: Whether to re-raise errors encountered when cancelling the
+            scheduled call.
+        """
+        # We make a copy here since calling `cancel()` on a delayed_call
+        # will result in the call removing itself from the map mid-iteration.
+        for call in list(self._call_id_to_delayed_call.values()):
+            try:
+                call.cancel()
+            except Exception:
+                if not ignore_errs:
+                    raise
+        self._call_id_to_delayed_call.clear()
+
     def call_when_running(
         self,
         callback: Callable[P, object],
@@ -285,7 +399,7 @@ class Clock:
         callback: Callable[P, object],
         *args: P.args,
         **kwargs: P.kwargs,
-    ) -> None:
+    ) -> Any:
         """
         Add a function to be called when a system event occurs.
 
@@ -299,6 +413,9 @@ class Clock:
             callback: Function to call
             *args: Postional arguments to pass to function.
             **kwargs: Key arguments to pass to function.
+
+        Returns:
+            an ID that can be used to remove this call with `reactor.removeSystemEventTrigger`.
         """
 
         def wrapped_callback(*args: Any, **kwargs: Any) -> None:
@@ -334,6 +451,50 @@ class Clock:
 
         # We can ignore the lint here since this class is the one location
         # `addSystemEventTrigger` should be called.
-        self._reactor.addSystemEventTrigger(
+        return self._reactor.addSystemEventTrigger(
             phase, event_type, wrapped_callback, *args, **kwargs
         )  # type: ignore[prefer-synapse-clock-add-system-event-trigger]
+
+
+@implementer(IDelayedCall)
+class DelayedCallWrapper:
+    """Wraps an `IDelayedCall` so that we can intercept the call to `cancel()` and
+    properly cleanup the delayed call from the tracking map of the `Clock`.
+
+    args:
+        delayed_call: The actual `IDelayedCall`
+        call_id: Unique identifier for this delayed call
+        clock: The clock instance tracking this call
+    """
+
+    def __init__(self, delayed_call: IDelayedCall, call_id: int, clock: Clock):
+        self.delayed_call = delayed_call
+        self.call_id = call_id
+        self.clock = clock
+
+    def cancel(self) -> None:
+        """Remove the call from the tracking map and propagate the call to the
+        underlying delayed_call.
+        """
+        self.delayed_call.cancel()
+        try:
+            self.clock._call_id_to_delayed_call.pop(self.call_id)
+        except KeyError:
+            # If the delayed call isn't being tracked anymore we can just move on.
+            pass
+
+    def getTime(self) -> float:
+        """Propagate the call to the underlying delayed_call."""
+        return self.delayed_call.getTime()
+
+    def delay(self, secondsLater: float) -> None:
+        """Propagate the call to the underlying delayed_call."""
+        self.delayed_call.delay(secondsLater)
+
+    def reset(self, secondsFromNow: float) -> None:
+        """Propagate the call to the underlying delayed_call."""
+        self.delayed_call.reset(secondsFromNow)
+
+    def active(self) -> bool:
+        """Propagate the call to the underlying delayed_call."""
+        return self.delayed_call.active()
diff --git a/synapse/util/constants.py b/synapse/util/constants.py
index 9986017147..7a3d073df5 100644
--- a/synapse/util/constants.py
+++ b/synapse/util/constants.py
@@ -18,3 +18,5 @@
 # readability and catching bugs.
 ONE_MINUTE_SECONDS = 60
 ONE_HOUR_SECONDS = 60 * ONE_MINUTE_SECONDS
+
+MILLISECONDS_PER_SECOND = 1000
diff --git a/synapse/util/daemonize.py b/synapse/util/daemonize.py
index dba815040d..63e0571a78 100644
--- a/synapse/util/daemonize.py
+++ b/synapse/util/daemonize.py
@@ -27,7 +27,7 @@ import os
 import signal
 import sys
 from types import FrameType, TracebackType
-from typing import NoReturn, Optional, Type
+from typing import NoReturn
 
 from synapse.logging.context import (
     LoggingContext,
@@ -119,9 +119,9 @@ def daemonize_process(pid_file: str, logger: logging.Logger, chdir: str = "/") -
     # also catch any other uncaught exceptions before we get that far.)
 
     def excepthook(
-        type_: Type[BaseException],
+        type_: type[BaseException],
         value: BaseException,
-        traceback: Optional[TracebackType],
+        traceback: TracebackType | None,
     ) -> None:
         logger.critical("Unhanded exception", exc_info=(type_, value, traceback))
 
@@ -144,7 +144,7 @@ def daemonize_process(pid_file: str, logger: logging.Logger, chdir: str = "/") -
         sys.exit(1)
 
     # write a log line on SIGTERM.
-    def sigterm(signum: int, frame: Optional[FrameType]) -> NoReturn:
+    def sigterm(signum: int, frame: FrameType | None) -> NoReturn:
         logger.warning("Caught signal %s. Stopping daemon.", signum)
         sys.exit(0)
 
diff --git a/synapse/util/distributor.py b/synapse/util/distributor.py
index f48ae3373c..23ef67c752 100644
--- a/synapse/util/distributor.py
+++ b/synapse/util/distributor.py
@@ -20,15 +20,12 @@
 #
 import logging
 from typing import (
+    TYPE_CHECKING,
     Any,
     Awaitable,
     Callable,
-    Dict,
     Generic,
-    List,
-    Optional,
     TypeVar,
-    Union,
 )
 
 from typing_extensions import ParamSpec
@@ -36,10 +33,13 @@ from typing_extensions import ParamSpec
 from twisted.internet import defer
 
 from synapse.logging.context import make_deferred_yieldable, run_in_background
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.types import UserID
 from synapse.util.async_helpers import maybe_awaitable
 
+if TYPE_CHECKING:
+    from synapse.server import HomeServer
+
+
 logger = logging.getLogger(__name__)
 
 
@@ -58,15 +58,15 @@ class Distributor:
       model will do for today.
     """
 
-    def __init__(self, server_name: str) -> None:
+    def __init__(self, hs: "HomeServer") -> None:
         """
         Args:
             server_name: The homeserver name of the server (used to label metrics)
                 (this should be `hs.hostname`).
         """
-        self.server_name = server_name
-        self.signals: Dict[str, Signal] = {}
-        self.pre_registration: Dict[str, List[Callable]] = {}
+        self.hs = hs
+        self.signals: dict[str, Signal] = {}
+        self.pre_registration: dict[str, list[Callable]] = {}
 
     def declare(self, name: str) -> None:
         if name in self.signals:
@@ -97,8 +97,8 @@ class Distributor:
         if name not in self.signals:
             raise KeyError("%r does not have a signal named %s" % (self, name))
 
-        run_as_background_process(
-            name, self.server_name, self.signals[name].fire, *args, **kwargs
+        self.hs.run_as_background_process(
+            name, self.signals[name].fire, *args, **kwargs
         )
 
 
@@ -118,7 +118,7 @@ class Signal(Generic[P]):
 
     def __init__(self, name: str):
         self.name: str = name
-        self.observers: List[Callable[P, Any]] = []
+        self.observers: list[Callable[P, Any]] = []
 
     def observe(self, observer: Callable[P, Any]) -> None:
         """Adds a new callable to the observer list which will be invoked by
@@ -127,7 +127,7 @@ class Signal(Generic[P]):
         Each observer callable may return a Deferred."""
         self.observers.append(observer)
 
-    def fire(self, *args: P.args, **kwargs: P.kwargs) -> "defer.Deferred[List[Any]]":
+    def fire(self, *args: P.args, **kwargs: P.kwargs) -> "defer.Deferred[list[Any]]":
         """Invokes every callable in the observer list, passing in the args and
         kwargs. Exceptions thrown by observers are logged but ignored. It is
         not an error to fire a signal with no observers.
@@ -135,7 +135,7 @@ class Signal(Generic[P]):
         Returns a Deferred that will complete when all the observers have
         completed."""
 
-        async def do(observer: Callable[P, Union[R, Awaitable[R]]]) -> Optional[R]:
+        async def do(observer: Callable[P, R | Awaitable[R]]) -> R | None:
             try:
                 return await maybe_awaitable(observer(*args, **kwargs))
             except Exception as e:
diff --git a/synapse/util/events.py b/synapse/util/events.py
index 4808268702..19eca1c1ae 100644
--- a/synapse/util/events.py
+++ b/synapse/util/events.py
@@ -13,9 +13,10 @@
 #
 #
 
-from typing import Any, List, Optional
+from typing import Any
+
+from pydantic import Field, StrictStr, ValidationError, field_validator
 
-from synapse._pydantic_compat import Field, StrictStr, ValidationError, validator
 from synapse.types import JsonDict
 from synapse.util.pydantic_models import ParseModel
 from synapse.util.stringutils import random_string
@@ -40,7 +41,7 @@ class MTextRepresentation(ParseModel):
     """
 
     body: StrictStr
-    mimetype: Optional[StrictStr]
+    mimetype: StrictStr | None = None
 
 
 class MTopic(ParseModel):
@@ -52,7 +53,7 @@ class MTopic(ParseModel):
     See `TopicContentBlock` in the Matrix specification.
     """
 
-    m_text: Optional[List[MTextRepresentation]] = Field(alias="m.text")
+    m_text: list[MTextRepresentation] | None = Field(None, alias="m.text")
     """
     An ordered array of textual representations in different mimetypes.
     """
@@ -60,16 +61,17 @@ class MTopic(ParseModel):
     # Because "Receivers SHOULD use the first representation in the array that they
     # understand.", we ignore invalid representations in the `m.text` field and use
     # what we can.
-    @validator("m_text", pre=True)
+    @field_validator("m_text", mode="before")
+    @classmethod
     def ignore_invalid_representations(
         cls, m_text: Any
-    ) -> Optional[List[MTextRepresentation]]:
-        if not isinstance(m_text, list):
-            raise ValueError("m.text must be a list")
+    ) -> list[MTextRepresentation] | None:
+        if not isinstance(m_text, (list, tuple)):
+            raise ValueError("m.text must be a list or a tuple")
         representations = []
         for element in m_text:
             try:
-                representations.append(MTextRepresentation.parse_obj(element))
+                representations.append(MTextRepresentation.model_validate(element))
             except ValidationError:
                 continue
         return representations
@@ -85,22 +87,23 @@ class TopicContent(ParseModel):
     The topic in plain text.
     """
 
-    m_topic: Optional[MTopic] = Field(alias="m.topic")
+    m_topic: MTopic | None = Field(None, alias="m.topic")
     """
     Textual representation of the room topic in different mimetypes.
     """
 
     # We ignore invalid `m.topic` fields as we can always fall back to the plain-text
     # `topic` field.
-    @validator("m_topic", pre=True)
-    def ignore_invalid_m_topic(cls, m_topic: Any) -> Optional[MTopic]:
+    @field_validator("m_topic", mode="before")
+    @classmethod
+    def ignore_invalid_m_topic(cls, m_topic: Any) -> MTopic | None:
         try:
-            return MTopic.parse_obj(m_topic)
+            return MTopic.model_validate(m_topic)
         except ValidationError:
             return None
 
 
-def get_plain_text_topic_from_event_content(content: JsonDict) -> Optional[str]:
+def get_plain_text_topic_from_event_content(content: JsonDict) -> str | None:
     """
     Given the `content` of an `m.room.topic` event, returns the plain-text topic
     representation. Prefers pulling plain-text from the newer `m.topic` field if
@@ -114,7 +117,7 @@ def get_plain_text_topic_from_event_content(content: JsonDict) -> Optional[str]:
     """
 
     try:
-        topic_content = TopicContent.parse_obj(content)
+        topic_content = TopicContent.model_validate(content, strict=False)
     except ValidationError:
         return None
 
diff --git a/synapse/util/file_consumer.py b/synapse/util/file_consumer.py
index 9fa8d40234..8d64684084 100644
--- a/synapse/util/file_consumer.py
+++ b/synapse/util/file_consumer.py
@@ -19,7 +19,7 @@
 #
 
 import queue
-from typing import Any, BinaryIO, Optional, Union, cast
+from typing import Any, BinaryIO, cast
 
 from twisted.internet import threads
 from twisted.internet.defer import Deferred
@@ -50,7 +50,7 @@ class BackgroundFileConsumer:
         self._reactor: ISynapseReactor = reactor
 
         # Producer we're registered with
-        self._producer: Optional[Union[IPushProducer, IPullProducer]] = None
+        self._producer: IPushProducer | IPullProducer | None = None
 
         # True if PushProducer, false if PullProducer
         self.streaming = False
@@ -61,18 +61,18 @@ class BackgroundFileConsumer:
 
         # Queue of slices of bytes to be written. When producer calls
         # unregister a final None is sent.
-        self._bytes_queue: queue.Queue[Optional[bytes]] = queue.Queue()
+        self._bytes_queue: queue.Queue[bytes | None] = queue.Queue()
 
         # Deferred that is resolved when finished writing
         #
         # This is really Deferred[None], but mypy doesn't seem to like that.
-        self._finished_deferred: Optional[Deferred[Any]] = None
+        self._finished_deferred: Deferred[Any] | None = None
 
         # If the _writer thread throws an exception it gets stored here.
-        self._write_exception: Optional[Exception] = None
+        self._write_exception: Exception | None = None
 
     def registerProducer(
-        self, producer: Union[IPushProducer, IPullProducer], streaming: bool
+        self, producer: IPushProducer | IPullProducer, streaming: bool
     ) -> None:
         """Part of IConsumer interface
 
diff --git a/synapse/util/gai_resolver.py b/synapse/util/gai_resolver.py
index 3c7a966e87..f40de8dcc2 100644
--- a/synapse/util/gai_resolver.py
+++ b/synapse/util/gai_resolver.py
@@ -17,13 +17,8 @@ from socket import (
 from typing import (
     TYPE_CHECKING,
     Callable,
-    List,
     NoReturn,
-    Optional,
     Sequence,
-    Tuple,
-    Type,
-    Union,
 )
 
 from zope.interface import implementer
@@ -91,13 +86,13 @@ _socktypeToType = {
 }
 
 
-_GETADDRINFO_RESULT = List[
-    Tuple[
+_GETADDRINFO_RESULT = list[
+    tuple[
         AddressFamily,
         SocketKind,
         int,
         str,
-        Union[Tuple[str, int], Tuple[str, int, int, int], Tuple[int, bytes]],
+        tuple[str, int] | tuple[str, int, int, int] | tuple[int, bytes],
     ]
 ]
 
@@ -112,7 +107,7 @@ class GAIResolver:
     def __init__(
         self,
         reactor: IReactorThreads,
-        getThreadPool: Optional[Callable[[], "ThreadPool"]] = None,
+        getThreadPool: Callable[[], "ThreadPool"] | None = None,
         getaddrinfo: Callable[[str, int, int, int], _GETADDRINFO_RESULT] = getaddrinfo,
     ):
         """
@@ -141,7 +136,7 @@ class GAIResolver:
         resolutionReceiver: IResolutionReceiver,
         hostName: str,
         portNumber: int = 0,
-        addressTypes: Optional[Sequence[Type[IAddress]]] = None,
+        addressTypes: Sequence[type[IAddress]] | None = None,
         transportSemantics: str = "TCP",
     ) -> IHostResolution:
         """
diff --git a/synapse/util/httpresourcetree.py b/synapse/util/httpresourcetree.py
index 6471b31c94..46fa92a4c5 100644
--- a/synapse/util/httpresourcetree.py
+++ b/synapse/util/httpresourcetree.py
@@ -20,7 +20,6 @@
 #
 
 import logging
-from typing import Dict
 
 from twisted.web.resource import Resource
 
@@ -30,7 +29,7 @@ logger = logging.getLogger(__name__)
 
 
 def create_resource_tree(
-    desired_tree: Dict[str, Resource], root_resource: Resource
+    desired_tree: dict[str, Resource], root_resource: Resource
 ) -> Resource:
     """Create the resource tree for this homeserver.
 
@@ -48,7 +47,7 @@ def create_resource_tree(
     # unless you give it a Request object IN ADDITION to the name :/ So
     # instead, we'll store a copy of this mapping so we can actually add
     # extra resources to existing nodes. See self._resource_id for the key.
-    resource_mappings: Dict[str, Resource] = {}
+    resource_mappings: dict[str, Resource] = {}
     for full_path_str, res in desired_tree.items():
         # twisted requires all resources to be bytes
         full_path = full_path_str.encode("utf-8")
diff --git a/synapse/util/iterutils.py b/synapse/util/iterutils.py
index 0a6a30aab2..19789a4666 100644
--- a/synapse/util/iterutils.py
+++ b/synapse/util/iterutils.py
@@ -24,16 +24,12 @@ from itertools import islice
 from typing import (
     Callable,
     Collection,
-    Dict,
     Generator,
     Iterable,
     Iterator,
-    List,
     Mapping,
     Protocol,
-    Set,
     Sized,
-    Tuple,
     TypeVar,
 )
 
@@ -52,7 +48,7 @@ class _SelfSlice(Sized, Protocol):
     def __getitem__(self: S, i: slice) -> S: ...
 
 
-def batch_iter(iterable: Iterable[T], size: int) -> Iterator[Tuple[T, ...]]:
+def batch_iter(iterable: Iterable[T], size: int) -> Iterator[tuple[T, ...]]:
     """batch an iterable up into tuples with a maximum size
 
     Args:
@@ -80,7 +76,7 @@ def chunk_seq(iseq: S, maxlen: int) -> Iterator[S]:
 
 def partition(
     iterable: Iterable[T], predicate: Callable[[T], bool]
-) -> Tuple[List[T], List[T]]:
+) -> tuple[list[T], list[T]]:
     """
     Separate a given iterable into two lists based on the result of a predicate function.
 
@@ -115,7 +111,7 @@ def sorted_topologically(
     # This is implemented by Kahn's algorithm.
 
     degree_map = dict.fromkeys(nodes, 0)
-    reverse_graph: Dict[T, Set[T]] = {}
+    reverse_graph: dict[T, set[T]] = {}
 
     for node, edges in graph.items():
         if node not in degree_map:
@@ -165,7 +161,7 @@ def sorted_topologically_batched(
     """
 
     degree_map = dict.fromkeys(nodes, 0)
-    reverse_graph: Dict[T, Set[T]] = {}
+    reverse_graph: dict[T, set[T]] = {}
 
     for node, edges in graph.items():
         if node not in degree_map:
diff --git a/synapse/util/json.py b/synapse/util/json.py
index e6db55f8e4..b1091704a8 100644
--- a/synapse/util/json.py
+++ b/synapse/util/json.py
@@ -16,7 +16,6 @@
 import json
 from typing import (
     Any,
-    Dict,
 )
 
 from immutabledict import immutabledict
@@ -27,7 +26,7 @@ def _reject_invalid_json(val: Any) -> None:
     raise ValueError("Invalid JSON value: '%s'" % val)
 
 
-def _handle_immutabledict(obj: Any) -> Dict[Any, Any]:
+def _handle_immutabledict(obj: Any) -> dict[Any, Any]:
     """Helper for json_encoder. Makes immutabledicts serializable by returning
     the underlying dict
     """
diff --git a/synapse/util/linked_list.py b/synapse/util/linked_list.py
index 87f801c0cf..c7a164d02e 100644
--- a/synapse/util/linked_list.py
+++ b/synapse/util/linked_list.py
@@ -22,7 +22,7 @@
 """A circular doubly linked list implementation."""
 
 import threading
-from typing import Generic, Optional, Type, TypeVar
+from typing import Generic, TypeVar
 
 P = TypeVar("P")
 LN = TypeVar("LN", bound="ListNode")
@@ -47,13 +47,13 @@ class ListNode(Generic[P]):
         "next_node",
     ]
 
-    def __init__(self, cache_entry: Optional[P] = None) -> None:
+    def __init__(self, cache_entry: P | None = None) -> None:
         self.cache_entry = cache_entry
-        self.prev_node: Optional[ListNode[P]] = None
-        self.next_node: Optional[ListNode[P]] = None
+        self.prev_node: ListNode[P] | None = None
+        self.next_node: ListNode[P] | None = None
 
     @classmethod
-    def create_root_node(cls: Type["ListNode[P]"]) -> "ListNode[P]":
+    def create_root_node(cls: type["ListNode[P]"]) -> "ListNode[P]":
         """Create a new linked list by creating a "root" node, which is a node
         that has prev_node/next_node pointing to itself and no associated cache
         entry.
@@ -65,7 +65,7 @@ class ListNode(Generic[P]):
 
     @classmethod
     def insert_after(
-        cls: Type[LN],
+        cls: type[LN],
         cache_entry: P,
         node: "ListNode[P]",
     ) -> LN:
@@ -149,7 +149,7 @@ class ListNode(Generic[P]):
         prev_node.next_node = self
         next_node.prev_node = self
 
-    def get_cache_entry(self) -> Optional[P]:
+    def get_cache_entry(self) -> P | None:
         """Get the cache entry, returns None if this is the root node (i.e.
         cache_entry is None) or if the entry has been dropped.
         """
diff --git a/synapse/util/macaroons.py b/synapse/util/macaroons.py
index d683a57ab1..178b6fa377 100644
--- a/synapse/util/macaroons.py
+++ b/synapse/util/macaroons.py
@@ -22,7 +22,7 @@
 
 """Utilities for manipulating macaroons"""
 
-from typing import Callable, Literal, Optional
+from typing import Callable, Literal
 
 import attr
 import pymacaroons
@@ -52,7 +52,7 @@ def get_value_from_macaroon(macaroon: pymacaroons.Macaroon, key: str) -> str:
              caveat in the macaroon, or if the caveat was not found in the macaroon.
     """
     prefix = key + " = "
-    result: Optional[str] = None
+    result: str | None = None
     for caveat in macaroon.caveats:
         if not caveat.caveat_id.startswith(prefix):
             continue
diff --git a/synapse/util/manhole.py b/synapse/util/manhole.py
index 63ec3e7e1b..859e9a9072 100644
--- a/synapse/util/manhole.py
+++ b/synapse/util/manhole.py
@@ -21,7 +21,7 @@
 import inspect
 import sys
 import traceback
-from typing import Any, Dict, Optional
+from typing import Any
 
 from twisted.conch import manhole_ssh
 from twisted.conch.insults import insults
@@ -71,7 +71,7 @@ EddTrx3TNpr1D5m/f+6mnXWrc8u9y1+GNx9yz889xMjIBTBI9KqaaOs=
 -----END RSA PRIVATE KEY-----"""
 
 
-def manhole(settings: ManholeConfig, globals: Dict[str, Any]) -> ServerFactory:
+def manhole(settings: ManholeConfig, globals: dict[str, Any]) -> ServerFactory:
     """Starts a ssh listener with password authentication using
     the given username and password. Clients connecting to the ssh
     listener will find themselves in a colored python shell with
@@ -130,7 +130,7 @@ class SynapseManhole(ColoredManhole):
 
 
 class SynapseManholeInterpreter(ManholeInterpreter):
-    def showsyntaxerror(self, filename: Optional[str] = None) -> None:
+    def showsyntaxerror(self, filename: str | None = None) -> None:
         """Display the syntax error that just occurred.
 
         Overrides the base implementation, ignoring sys.excepthook. We always want
diff --git a/synapse/util/metrics.py b/synapse/util/metrics.py
index c4f3c8b965..3daba79124 100644
--- a/synapse/util/metrics.py
+++ b/synapse/util/metrics.py
@@ -25,11 +25,8 @@ from types import TracebackType
 from typing import (
     Awaitable,
     Callable,
-    Dict,
     Generator,
-    Optional,
     Protocol,
-    Type,
     TypeVar,
 )
 
@@ -138,7 +135,7 @@ class HasClockAndServerName(Protocol):
 
 
 def measure_func(
-    name: Optional[str] = None,
+    name: str | None = None,
 ) -> Callable[[Callable[P, Awaitable[R]]], Callable[P, Awaitable[R]]]:
     """Decorate an async method with a `Measure` context manager.
 
@@ -222,7 +219,7 @@ class Measure:
             server_name=self.server_name,
             parent_context=parent_context,
         )
-        self.start: Optional[float] = None
+        self.start: float | None = None
 
     def __enter__(self) -> "Measure":
         if self.start is not None:
@@ -238,9 +235,9 @@ class Measure:
 
     def __exit__(
         self,
-        exc_type: Optional[Type[BaseException]],
-        exc_val: Optional[BaseException],
-        exc_tb: Optional[TracebackType],
+        exc_type: type[BaseException] | None,
+        exc_val: BaseException | None,
+        exc_tb: TracebackType | None,
     ) -> None:
         if self.start is None:
             raise RuntimeError("Measure() block exited without being entered")
@@ -293,21 +290,50 @@ class DynamicCollectorRegistry(CollectorRegistry):
 
     def __init__(self) -> None:
         super().__init__()
-        self._pre_update_hooks: Dict[str, Callable[[], None]] = {}
+        self._server_name_to_pre_update_hooks: dict[
+            str, dict[str, Callable[[], None]]
+        ] = {}
+        """
+        Mapping of server name to a mapping of metric name to metric pre-update
+        hook
+        """
 
     def collect(self) -> Generator[Metric, None, None]:
         """
         Collects metrics, calling pre-update hooks first.
         """
 
-        for pre_update_hook in self._pre_update_hooks.values():
-            pre_update_hook()
+        for pre_update_hooks in self._server_name_to_pre_update_hooks.values():
+            for pre_update_hook in pre_update_hooks.values():
+                pre_update_hook()
 
         yield from super().collect()
 
-    def register_hook(self, metric_name: str, hook: Callable[[], None]) -> None:
+    def register_hook(
+        self, server_name: str, metric_name: str, hook: Callable[[], None]
+    ) -> None:
         """
         Registers a hook that is called before metric collection.
         """
 
-        self._pre_update_hooks[metric_name] = hook
+        server_hooks = self._server_name_to_pre_update_hooks.setdefault(server_name, {})
+        if server_hooks.get(metric_name) is not None:
+            # TODO: This should be an `assert` since registering the same metric name
+            # multiple times will clobber the old metric.
+            #
+            # We currently rely on this behaviour in a few places:
+            #  - We instantiate multiple `SyncRestServlet`, one per listener, and in the
+            #   `__init__` we setup a new `LruCache`.
+            #  - We instantiate multiple `ApplicationService` (one per configured
+            #    application service) which use the `@cached` decorator on some methods.
+            #
+            # Once the above behaviour is changed, this should be changed to an `assert`.
+            logger.error(
+                "Metric named %s already registered for server %s",
+                metric_name,
+                server_name,
+            )
+        server_hooks[metric_name] = hook
+
+    def unregister_hooks_for_homeserver(self, server_name: str) -> None:
+        self._server_name_to_pre_update_hooks.pop(server_name, None)
diff --git a/synapse/util/module_loader.py b/synapse/util/module_loader.py
index a33c75d54e..ae50e302ed 100644
--- a/synapse/util/module_loader.py
+++ b/synapse/util/module_loader.py
@@ -21,7 +21,7 @@
 import importlib
 import importlib.util
 from types import ModuleType
-from typing import Any, Tuple, Type
+from typing import Any
 
 import jsonschema
 
@@ -30,7 +30,7 @@ from synapse.config._util import json_error_to_config_error
 from synapse.types import StrSequence
 
 
-def load_module(provider: dict, config_path: StrSequence) -> Tuple[Type, Any]:
+def load_module(provider: dict, config_path: StrSequence) -> tuple[type, Any]:
     """Loads a synapse module with its config
 
     Args:
diff --git a/synapse/util/patch_inline_callbacks.py b/synapse/util/patch_inline_callbacks.py
index c776ad65b3..fca166a5b8 100644
--- a/synapse/util/patch_inline_callbacks.py
+++ b/synapse/util/patch_inline_callbacks.py
@@ -21,7 +21,7 @@
 import functools
 import sys
 from types import GeneratorType
-from typing import Any, Callable, Generator, List, TypeVar, cast
+from typing import Any, Callable, Generator, TypeVar, cast
 
 from typing_extensions import ParamSpec
 
@@ -56,7 +56,7 @@ def do_patch() -> None:
         @functools.wraps(f)
         def wrapped(*args: P.args, **kwargs: P.kwargs) -> "Deferred[T]":
             start_context = current_context()
-            changes: List[str] = []
+            changes: list[str] = []
             orig: Callable[P, "Deferred[T]"] = orig_inline_callbacks(
                 _check_yield_points(f, changes)
             )
@@ -126,7 +126,7 @@ def do_patch() -> None:
 
 def _check_yield_points(
     f: Callable[P, Generator["Deferred[object]", object, T]],
-    changes: List[str],
+    changes: list[str],
 ) -> Callable:
     """Wraps a generator that is about to be passed to defer.inlineCallbacks
     checking that after every yield the log contexts are correct.
diff --git a/synapse/util/pydantic_models.py b/synapse/util/pydantic_models.py
index 4880709501..783d122013 100644
--- a/synapse/util/pydantic_models.py
+++ b/synapse/util/pydantic_models.py
@@ -13,21 +13,30 @@
 #
 #
 
-import re
-from typing import Any, Callable, Generator
+from typing import Annotated
 
-from synapse._pydantic_compat import BaseModel, Extra, StrictStr
+from pydantic import AfterValidator, BaseModel, ConfigDict, StrictStr, StringConstraints
+
+from synapse.api.errors import SynapseError
 from synapse.types import EventID
 
 
 class ParseModel(BaseModel):
     """A custom version of Pydantic's BaseModel which
 
-     - ignores unknown fields and
-     - does not allow fields to be overwritten after construction,
+     - ignores unknown fields,
+     - does not allow fields to be overwritten after construction and
+     - enables strict mode,
 
     but otherwise uses Pydantic's default behaviour.
 
+    Strict mode can adversely affect some types of fields, and should be disabled
+    for a field if:
+
+    - the field's type is a `Path` or `FilePath`. Strict mode will refuse to
+      coerce from `str` (likely what the yaml parser will produce) to `FilePath`,
+      raising a `ValidationError`.
+
     For now, ignore unknown fields. In the future, we could change this so that unknown
     config values cause a ValidationError, provided the error messages are meaningful to
     server operators.
@@ -36,48 +45,19 @@ class ParseModel(BaseModel):
     https://pydantic-docs.helpmanual.io/usage/model_config/#change-behaviour-globally
     """
 
-    class Config:
-        # By default, ignore fields that we don't recognise.
-        extra = Extra.ignore
-        # By default, don't allow fields to be reassigned after parsing.
-        allow_mutation = False
+    model_config = ConfigDict(extra="ignore", frozen=True, strict=True)
 
 
-class AnyEventId(StrictStr):
-    """
-    A validator for strings that need to be an Event ID.
+def validate_event_id_v1_and_2(value: str) -> str:
+    try:
+        EventID.from_string(value)
+    except SynapseError as e:
+        raise ValueError from e
+    return value
 
-    Accepts any valid grammar of Event ID from any room version.
-    """
 
-    EVENT_ID_HASH_ROOM_VERSION_3_PLUS = re.compile(
-        r"^([a-zA-Z0-9-_]{43}|[a-zA-Z0-9+/]{43})$"
-    )
-
-    @classmethod
-    def __get_validators__(cls) -> Generator[Callable[..., Any], Any, Any]:
-        yield from super().__get_validators__()  # type: ignore
-        yield cls.validate_event_id
-
-    @classmethod
-    def validate_event_id(cls, value: str) -> str:
-        if not value.startswith("$"):
-            raise ValueError("Event ID must start with `$`")
-
-        if ":" in value:
-            # Room versions 1 and 2
-            EventID.from_string(value)  # throws on fail
-        else:
-            # Room versions 3+: event ID is $ + a base64 sha256 hash
-            # Room version 3 is base64, 4+ are base64Url
-            # In both cases, the base64 is unpadded.
-            # refs:
-            # - https://spec.matrix.org/v1.15/rooms/v3/ e.g. $acR1l0raoZnm60CBwAVgqbZqoO/mYU81xysh1u7XcJk
-            # - https://spec.matrix.org/v1.15/rooms/v4/ e.g. $Rqnc-F-dvnEYJTyHq_iKxU2bZ1CI92-kuZq3a5lr5Zg
-            b64_hash = value[1:]
-            if cls.EVENT_ID_HASH_ROOM_VERSION_3_PLUS.fullmatch(b64_hash) is None:
-                raise ValueError(
-                    "Event ID must either have a domain part or be a valid hash"
-                )
-
-        return value
+EventIdV1And2 = Annotated[StrictStr, AfterValidator(validate_event_id_v1_and_2)]
+EventIdV3Plus = Annotated[
+    StrictStr, StringConstraints(pattern=r"^\$([a-zA-Z0-9-_]{43}|[a-zA-Z0-9+/]{43})$")
+]
+AnyEventId = EventIdV1And2 | EventIdV3Plus
diff --git a/synapse/util/ratelimitutils.py b/synapse/util/ratelimitutils.py
index 695eb462bf..024706d9cf 100644
--- a/synapse/util/ratelimitutils.py
+++ b/synapse/util/ratelimitutils.py
@@ -28,15 +28,9 @@ from typing import (
     Any,
     Callable,
     ContextManager,
-    DefaultDict,
-    Dict,
     Iterator,
-    List,
     Mapping,
     MutableSet,
-    Optional,
-    Set,
-    Tuple,
 )
 from weakref import WeakSet
 
@@ -104,7 +98,7 @@ _rate_limiter_instances_lock = threading.Lock()
 
 def _get_counts_from_rate_limiter_instance(
     count_func: Callable[["FederationRateLimiter"], int],
-) -> Mapping[Tuple[str, ...], int]:
+) -> Mapping[tuple[str, ...], int]:
     """Returns a count of something (slept/rejected hosts) by (metrics_name)"""
     # Cast to a list to prevent it changing while the Prometheus
     # thread is collecting metrics
@@ -114,7 +108,7 @@ def _get_counts_from_rate_limiter_instance(
     # Map from (metrics_name,) -> int, the number of something like slept hosts
     # or rejected hosts. The key type is Tuple[str], but we leave the length
     # unspecified for compatability with LaterGauge's annotations.
-    counts: Dict[Tuple[str, ...], int] = {}
+    counts: dict[tuple[str, ...], int] = {}
     for rate_limiter_instance in rate_limiter_instances:
         # Only track metrics if they provided a `metrics_name` to
         # differentiate this instance of the rate limiter.
@@ -169,7 +163,7 @@ class FederationRateLimiter:
         our_server_name: str,
         clock: Clock,
         config: FederationRatelimitSettings,
-        metrics_name: Optional[str] = None,
+        metrics_name: str | None = None,
     ):
         """
         Args:
@@ -191,7 +185,7 @@ class FederationRateLimiter:
                 metrics_name=metrics_name,
             )
 
-        self.ratelimiters: DefaultDict[str, "_PerHostRatelimiter"] = (
+        self.ratelimiters: collections.defaultdict[str, "_PerHostRatelimiter"] = (
             collections.defaultdict(new_limiter)
         )
 
@@ -222,7 +216,7 @@ class _PerHostRatelimiter:
         our_server_name: str,
         clock: Clock,
         config: FederationRatelimitSettings,
-        metrics_name: Optional[str] = None,
+        metrics_name: str | None = None,
     ):
         """
         Args:
@@ -244,7 +238,7 @@ class _PerHostRatelimiter:
         self.concurrent_requests = config.concurrent
 
         # request_id objects for requests which have been slept
-        self.sleeping_requests: Set[object] = set()
+        self.sleeping_requests: set[object] = set()
 
         # map from request_id object to Deferred for requests which are ready
         # for processing but have been queued
@@ -253,11 +247,11 @@ class _PerHostRatelimiter:
         ] = collections.OrderedDict()
 
         # request id objects for requests which are in progress
-        self.current_processing: Set[object] = set()
+        self.current_processing: set[object] = set()
 
         # times at which we have recently (within the last window_size ms)
         # received requests.
-        self.request_times: List[int] = []
+        self.request_times: list[int] = []
 
     @contextlib.contextmanager
     def ratelimit(self, host: str) -> "Iterator[defer.Deferred[None]]":
@@ -419,4 +413,7 @@ class _PerHostRatelimiter:
             except KeyError:
                 pass
 
-        self.clock.call_later(0.0, start_next_request)
+        self.clock.call_later(
+            0.0,
+            start_next_request,
+        )
diff --git a/synapse/util/retryutils.py b/synapse/util/retryutils.py
index 42a0cc7aa8..8a5aab50f1 100644
--- a/synapse/util/retryutils.py
+++ b/synapse/util/retryutils.py
@@ -21,10 +21,9 @@
 import logging
 import random
 from types import TracebackType
-from typing import TYPE_CHECKING, Any, Optional, Type
+from typing import TYPE_CHECKING, Any, Optional
 
 from synapse.api.errors import CodeMessageException
-from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.storage import DataStore
 from synapse.types import StrCollection
 from synapse.util.clock import Clock
@@ -32,6 +31,7 @@ from synapse.util.clock import Clock
 if TYPE_CHECKING:
     from synapse.notifier import Notifier
     from synapse.replication.tcp.handler import ReplicationCommandHandler
+    from synapse.server import HomeServer
 
 logger = logging.getLogger(__name__)
 
@@ -62,6 +62,7 @@ async def get_retry_limiter(
     *,
     destination: str,
     our_server_name: str,
+    hs: "HomeServer",
     clock: Clock,
     store: DataStore,
     ignore_backoff: bool = False,
@@ -124,6 +125,7 @@ async def get_retry_limiter(
     return RetryDestinationLimiter(
         destination=destination,
         our_server_name=our_server_name,
+        hs=hs,
         clock=clock,
         store=store,
         failure_ts=failure_ts,
@@ -163,9 +165,10 @@ class RetryDestinationLimiter:
         *,
         destination: str,
         our_server_name: str,
+        hs: "HomeServer",
         clock: Clock,
         store: DataStore,
-        failure_ts: Optional[int],
+        failure_ts: int | None,
         retry_interval: int,
         backoff_on_404: bool = False,
         backoff_on_failure: bool = True,
@@ -181,6 +184,7 @@ class RetryDestinationLimiter:
         Args:
             destination
             our_server_name: Our homeserver name (used to label metrics) (`hs.hostname`)
+            hs: The homeserver instance
             clock
             store
             failure_ts: when this destination started failing (in ms since
@@ -197,6 +201,7 @@ class RetryDestinationLimiter:
                 error code.
         """
         self.our_server_name = our_server_name
+        self.hs = hs
         self.clock = clock
         self.store = store
         self.destination = destination
@@ -225,9 +230,9 @@ class RetryDestinationLimiter:
 
     def __exit__(
         self,
-        exc_type: Optional[Type[BaseException]],
-        exc_val: Optional[BaseException],
-        exc_tb: Optional[TracebackType],
+        exc_type: type[BaseException] | None,
+        exc_val: BaseException | None,
+        exc_tb: TracebackType | None,
     ) -> None:
         success = exc_type is None
         valid_err_code = False
@@ -331,6 +336,4 @@ class RetryDestinationLimiter:
                 logger.exception("Failed to store destination_retry_timings")
 
         # we deliberately do this in the background.
-        run_as_background_process(
-            "store_retry_timings", self.our_server_name, store_retry_timings
-        )
+        self.hs.run_as_background_process("store_retry_timings", store_retry_timings)
diff --git a/synapse/util/rust.py b/synapse/util/rust.py
index 37f43459f1..63b53b917f 100644
--- a/synapse/util/rust.py
+++ b/synapse/util/rust.py
@@ -24,7 +24,6 @@ import os
 import urllib.parse
 from hashlib import blake2b
 from importlib.metadata import Distribution, PackageNotFoundError
-from typing import Optional
 
 import synapse
 from synapse.synapse_rust import get_rust_file_digest
@@ -80,7 +79,7 @@ def _hash_rust_files_in_directory(directory: str) -> str:
     return hasher.hexdigest()
 
 
-def get_synapse_source_directory() -> Optional[str]:
+def get_synapse_source_directory() -> str | None:
     """Try and find the source directory of synapse for editable installs (like
     those used in development).
 
diff --git a/synapse/util/stringutils.py b/synapse/util/stringutils.py
index 32b5bc00c9..cc26c5181b 100644
--- a/synapse/util/stringutils.py
+++ b/synapse/util/stringutils.py
@@ -20,10 +20,11 @@
 #
 #
 import itertools
+import random
 import re
 import secrets
 import string
-from typing import Any, Iterable, Optional, Tuple
+from typing import Any, Iterable
 
 from netaddr import valid_ipv6
 
@@ -56,6 +57,10 @@ def random_string(length: int) -> str:
     """Generate a cryptographically secure string of random letters.
 
     Drawn from the characters: `a-z` and `A-Z`
+
+    Because this is generated from cryptographic sources, it takes a notable amount of
+    effort to generate (computationally expensive). If you don't need cryptographic
+    security, consider using `random_string_insecure_fast` for better performance.
     """
     return "".join(secrets.choice(string.ascii_letters) for _ in range(length))
 
@@ -68,6 +73,18 @@ def random_string_with_symbols(length: int) -> str:
     return "".join(secrets.choice(_string_with_symbols) for _ in range(length))
 
 
+def random_string_insecure_fast(length: int) -> str:
+    """
+    Generate a string of random letters (insecure, fast). This is a more performant but
+    insecure version of `random_string`.
+
+    WARNING: Not for security or cryptographic uses. Use `random_string` instead.
+
+    Drawn from the characters: `a-z` and `A-Z`
+    """
+    return "".join(random.choice(string.ascii_letters) for _ in range(length))
+
+
 def is_ascii(s: bytes) -> bool:
     try:
         s.decode("ascii").encode("ascii")
@@ -92,7 +109,7 @@ def assert_valid_client_secret(client_secret: str) -> None:
         )
 
 
-def parse_server_name(server_name: str) -> Tuple[str, Optional[int]]:
+def parse_server_name(server_name: str) -> tuple[str, int | None]:
     """Split a server name into host/port parts.
 
     Args:
@@ -123,7 +140,7 @@ def parse_server_name(server_name: str) -> Tuple[str, Optional[int]]:
 VALID_HOST_REGEX = re.compile("\\A[0-9a-zA-Z-]+(?:\\.[0-9a-zA-Z-]+)*\\Z")
 
 
-def parse_and_validate_server_name(server_name: str) -> Tuple[str, Optional[int]]:
+def parse_and_validate_server_name(server_name: str) -> tuple[str, int | None]:
     """Split a server name into host/port parts and do some basic validation.
 
     Args:
@@ -190,7 +207,7 @@ def valid_id_server_location(id_server: str) -> bool:
     return "#" not in path and "?" not in path
 
 
-def parse_and_validate_mxc_uri(mxc: str) -> Tuple[str, Optional[int], str]:
+def parse_and_validate_mxc_uri(mxc: str) -> tuple[str, int | None, str]:
     """Parse the given string as an MXC URI
 
     Checks that the "server name" part is a valid server name
@@ -268,7 +285,7 @@ def base62_encode(num: int, minwidth: int = 1) -> str:
     return pad + res
 
 
-def non_null_str_or_none(val: Any) -> Optional[str]:
+def non_null_str_or_none(val: Any) -> str | None:
     """Check that the arg is a string containing no null (U+0000) codepoints.
 
     If so, returns the given string unmodified; otherwise, returns None.
diff --git a/synapse/util/task_scheduler.py b/synapse/util/task_scheduler.py
index 0539989320..3b4423a1ff 100644
--- a/synapse/util/task_scheduler.py
+++ b/synapse/util/task_scheduler.py
@@ -20,19 +20,18 @@
 #
 
 import logging
-from typing import TYPE_CHECKING, Awaitable, Callable, Dict, List, Optional, Set, Tuple
+from typing import TYPE_CHECKING, Awaitable, Callable
 
 from twisted.python.failure import Failure
 
 from synapse.logging.context import (
     ContextResourceUsage,
     LoggingContext,
+    PreserveLoggingContext,
     nested_logging_context,
-    set_current_context,
 )
 from synapse.metrics import SERVER_NAME_LABEL, LaterGauge
 from synapse.metrics.background_process_metrics import (
-    run_as_background_process,
     wrap_as_background_process,
 )
 from synapse.types import JsonMapping, ScheduledTask, TaskStatus
@@ -54,8 +53,8 @@ running_tasks_gauge = LaterGauge(
 class TaskScheduler:
     """
     This is a simple task scheduler designed for resumable tasks. Normally,
-    you'd use `run_in_background` to start a background task or Twisted's
-    `deferLater` if you want to run it later.
+    you'd use `run_in_background` to start a background task or `clock.call_later`
+    if you want to run it later.
 
     The issue is that these tasks stop completely and won't resume if Synapse is
     shut down for any reason.
@@ -107,19 +106,17 @@ class TaskScheduler:
     OCCASIONAL_REPORT_INTERVAL_MS = 5 * 60 * 1000  # 5 minutes
 
     def __init__(self, hs: "HomeServer"):
-        self._hs = hs
-        self.server_name = (
-            hs.hostname
-        )  # nb must be called this for @wrap_as_background_process
+        self.hs = hs  # nb must be called this for @wrap_as_background_process
+        self.server_name = hs.hostname
         self._store = hs.get_datastores().main
         self._clock = hs.get_clock()
-        self._running_tasks: Set[str] = set()
+        self._running_tasks: set[str] = set()
         # A map between action names and their registered function
-        self._actions: Dict[
+        self._actions: dict[
             str,
             Callable[
                 [ScheduledTask],
-                Awaitable[Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]],
+                Awaitable[tuple[TaskStatus, JsonMapping | None, str | None]],
             ],
         ] = {}
         self._run_background_tasks = hs.config.worker.run_background_tasks
@@ -146,7 +143,7 @@ class TaskScheduler:
         self,
         function: Callable[
             [ScheduledTask],
-            Awaitable[Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]],
+            Awaitable[tuple[TaskStatus, JsonMapping | None, str | None]],
         ],
         action_name: str,
     ) -> None:
@@ -170,9 +167,9 @@ class TaskScheduler:
         self,
         action: str,
         *,
-        resource_id: Optional[str] = None,
-        timestamp: Optional[int] = None,
-        params: Optional[JsonMapping] = None,
+        resource_id: str | None = None,
+        timestamp: int | None = None,
+        params: JsonMapping | None = None,
     ) -> str:
         """Schedule a new potentially resumable task. A function matching the specified
         `action` should've been registered with `register_action` before the task is run.
@@ -215,7 +212,7 @@ class TaskScheduler:
             if self._run_background_tasks:
                 self._launch_scheduled_tasks()
             else:
-                self._hs.get_replication_command_handler().send_new_active_task(task.id)
+                self.hs.get_replication_command_handler().send_new_active_task(task.id)
 
         return task.id
 
@@ -223,10 +220,10 @@ class TaskScheduler:
         self,
         id: str,
         *,
-        timestamp: Optional[int] = None,
-        status: Optional[TaskStatus] = None,
-        result: Optional[JsonMapping] = None,
-        error: Optional[str] = None,
+        timestamp: int | None = None,
+        status: TaskStatus | None = None,
+        result: JsonMapping | None = None,
+        error: str | None = None,
     ) -> bool:
         """Update some task-associated values. This is exposed publicly so it can
         be used inside task functions, mainly to update the result or resume
@@ -266,7 +263,7 @@ class TaskScheduler:
             error=error,
         )
 
-    async def get_task(self, id: str) -> Optional[ScheduledTask]:
+    async def get_task(self, id: str) -> ScheduledTask | None:
         """Get a specific task description by id.
 
         Args:
@@ -281,12 +278,12 @@ class TaskScheduler:
     async def get_tasks(
         self,
         *,
-        actions: Optional[List[str]] = None,
-        resource_id: Optional[str] = None,
-        statuses: Optional[List[TaskStatus]] = None,
-        max_timestamp: Optional[int] = None,
-        limit: Optional[int] = None,
-    ) -> List[ScheduledTask]:
+        actions: list[str] | None = None,
+        resource_id: str | None = None,
+        statuses: list[TaskStatus] | None = None,
+        max_timestamp: int | None = None,
+        limit: int | None = None,
+    ) -> list[ScheduledTask]:
         """Get a list of tasks. Returns all the tasks if no args are provided.
 
         If an arg is `None`, all tasks matching the other args will be selected.
@@ -362,7 +359,7 @@ class TaskScheduler:
             finally:
                 self._launching_new_tasks = False
 
-        run_as_background_process("launch_scheduled_tasks", self.server_name, inner)
+        self.hs.run_as_background_process("launch_scheduled_tasks", inner)
 
     @wrap_as_background_process("clean_scheduled_tasks")
     async def _clean_scheduled_tasks(self) -> None:
@@ -425,14 +422,11 @@ class TaskScheduler:
             """
 
             current_time = self._clock.time()
-            calling_context = set_current_context(task_log_context)
-            try:
+            with PreserveLoggingContext(task_log_context):
                 usage = task_log_context.get_resource_usage()
                 TaskScheduler._log_task_usage(
                     "continuing", task, usage, current_time - start_time
                 )
-            finally:
-                set_current_context(calling_context)
 
         async def wrapper() -> None:
             with nested_logging_context(task.id) as log_context:
@@ -473,7 +467,10 @@ class TaskScheduler:
                 occasional_status_call.stop()
 
             # Try launch a new task since we've finished with this one.
-            self._clock.call_later(0.1, self._launch_scheduled_tasks)
+            self._clock.call_later(
+                0.1,
+                self._launch_scheduled_tasks,
+            )
 
         if len(self._running_tasks) >= TaskScheduler.MAX_CONCURRENT_RUNNING_TASKS:
             return
@@ -493,4 +490,4 @@ class TaskScheduler:
 
         self._running_tasks.add(task.id)
         await self.update_task(task.id, status=TaskStatus.ACTIVE)
-        run_as_background_process(f"task-{task.action}", self.server_name, wrapper)
+        self.hs.run_as_background_process(f"task-{task.action}", wrapper)
diff --git a/synapse/util/templates.py b/synapse/util/templates.py
index fc5dbc069c..d399b167c1 100644
--- a/synapse/util/templates.py
+++ b/synapse/util/templates.py
@@ -23,7 +23,7 @@
 
 import time
 import urllib.parse
-from typing import TYPE_CHECKING, Callable, Optional, Sequence, Union
+from typing import TYPE_CHECKING, Callable, Sequence
 
 import jinja2
 
@@ -34,7 +34,7 @@ if TYPE_CHECKING:
 def build_jinja_env(
     template_search_directories: Sequence[str],
     config: "HomeServerConfig",
-    autoescape: Union[bool, Callable[[Optional[str]], bool], None] = None,
+    autoescape: bool | Callable[[str | None], bool] | None = None,
 ) -> jinja2.Environment:
     """Set up a Jinja2 environment to load templates from the given search path
 
@@ -82,7 +82,7 @@ def build_jinja_env(
 
 
 def _create_mxc_to_http_filter(
-    public_baseurl: Optional[str],
+    public_baseurl: str | None,
 ) -> Callable[[str, int, int, str], str]:
     """Create and return a jinja2 filter that converts MXC urls to HTTP
 
diff --git a/synapse/util/wheel_timer.py b/synapse/util/wheel_timer.py
index 95eb1d7185..c63faa96df 100644
--- a/synapse/util/wheel_timer.py
+++ b/synapse/util/wheel_timer.py
@@ -19,7 +19,7 @@
 #
 #
 import logging
-from typing import Generic, Hashable, List, Set, TypeVar
+from typing import Generic, Hashable, TypeVar
 
 import attr
 
@@ -31,7 +31,7 @@ T = TypeVar("T", bound=Hashable)
 @attr.s(slots=True, frozen=True, auto_attribs=True)
 class _Entry(Generic[T]):
     end_key: int
-    elements: Set[T] = attr.Factory(set)
+    elements: set[T] = attr.Factory(set)
 
 
 class WheelTimer(Generic[T]):
@@ -46,7 +46,7 @@ class WheelTimer(Generic[T]):
                 accuracy of the timer.
         """
         self.bucket_size: int = bucket_size
-        self.entries: List[_Entry[T]] = []
+        self.entries: list[_Entry[T]] = []
 
     def insert(self, now: int, obj: T, then: int) -> None:
         """Inserts object into timer.
@@ -91,7 +91,7 @@ class WheelTimer(Generic[T]):
 
         self.entries[-1].elements.add(obj)
 
-    def fetch(self, now: int) -> List[T]:
+    def fetch(self, now: int) -> list[T]:
         """Fetch any objects that have timed out
 
         Args:
@@ -102,7 +102,7 @@ class WheelTimer(Generic[T]):
         """
         now_key = int(now / self.bucket_size)
 
-        ret: List[T] = []
+        ret: list[T] = []
         while self.entries and self.entries[0].end_key <= now_key:
             ret.extend(self.entries.pop(0).elements)
 
diff --git a/synapse/visibility.py b/synapse/visibility.py
index 662f2636d0..16b39e6200 100644
--- a/synapse/visibility.py
+++ b/synapse/visibility.py
@@ -23,14 +23,8 @@ import logging
 from enum import Enum, auto
 from typing import (
     Collection,
-    Dict,
     Final,
-    FrozenSet,
-    List,
-    Optional,
     Sequence,
-    Set,
-    Tuple,
 )
 
 import attr
@@ -76,18 +70,18 @@ MEMBERSHIP_PRIORITY = (
     Membership.BAN,
 )
 
-_HISTORY_VIS_KEY: Final[Tuple[str, str]] = (EventTypes.RoomHistoryVisibility, "")
+_HISTORY_VIS_KEY: Final[tuple[str, str]] = (EventTypes.RoomHistoryVisibility, "")
 
 
 @trace
 async def filter_events_for_client(
     storage: StorageControllers,
     user_id: str,
-    events: List[EventBase],
+    events: list[EventBase],
     is_peeking: bool = False,
-    always_include_ids: FrozenSet[str] = frozenset(),
+    always_include_ids: frozenset[str] = frozenset(),
     filter_send_to_client: bool = True,
-) -> List[EventBase]:
+) -> list[EventBase]:
     """
     Check which events a user is allowed to see. If the user can see the event but its
     sender asked for their data to be erased, prune the content of the event.
@@ -160,14 +154,14 @@ async def filter_events_for_client(
 
     if filter_send_to_client:
         room_ids = {e.room_id for e in events}
-        retention_policies: Dict[str, RetentionPolicy] = {}
+        retention_policies: dict[str, RetentionPolicy] = {}
 
         for room_id in room_ids:
             retention_policies[
                 room_id
             ] = await storage.main.get_retention_policy_for_room(room_id)
 
-    def allowed(event: EventBase) -> Optional[EventBase]:
+    def allowed(event: EventBase) -> EventBase | None:
         state_after_event = event_id_to_state.get(event.event_id)
         filtered = _check_client_allowed_to_see_event(
             user_id=user_id,
@@ -190,7 +184,7 @@ async def filter_events_for_client(
         # we won't have such a state. The only outliers that are returned here are the
         # user's own membership event, so we can just inspect that.
 
-        user_membership_event: Optional[EventBase]
+        user_membership_event: EventBase | None
         if event.type == EventTypes.Member and event.state_key == user_id:
             user_membership_event = event
         elif state_after_event is not None:
@@ -351,12 +345,12 @@ def _check_client_allowed_to_see_event(
     clock: Clock,
     filter_send_to_client: bool,
     is_peeking: bool,
-    always_include_ids: FrozenSet[str],
+    always_include_ids: frozenset[str],
     sender_ignored: bool,
     retention_policy: RetentionPolicy,
-    state: Optional[StateMap[EventBase]],
+    state: StateMap[EventBase] | None,
     sender_erased: bool,
-) -> Optional[EventBase]:
+) -> EventBase | None:
     """Check with the given user is allowed to see the given event
 
     See `filter_events_for_client` for details about args
@@ -652,7 +646,7 @@ async def filter_events_for_server(
     redact: bool,
     filter_out_erased_senders: bool,
     filter_out_remote_partial_state_events: bool,
-) -> List[EventBase]:
+) -> list[EventBase]:
     """Filter a list of events based on whether the target server is allowed to
     see them.
 
@@ -687,7 +681,7 @@ async def filter_events_for_server(
     # otherwise a room could be fully joined after we retrieve those, which would then bypass
     # this check but would base the filtering on an outdated view of the membership events.
 
-    partial_state_invisible_event_ids: Set[str] = set()
+    partial_state_invisible_event_ids: set[str] = set()
     if filter_out_remote_partial_state_events:
         for e in events:
             sender_domain = get_domain_from_id(e.sender)
@@ -733,7 +727,7 @@ async def filter_events_for_server(
 
 async def _event_to_history_vis(
     storage: StorageControllers, events: Collection[EventBase]
-) -> Dict[str, str]:
+) -> dict[str, str]:
     """Get the history visibility at each of the given events
 
     Returns a map from event id to history_visibility setting
@@ -758,7 +752,7 @@ async def _event_to_history_vis(
     }
     vis_events = await storage.main.get_events(visibility_ids)
 
-    result: Dict[str, str] = {}
+    result: dict[str, str] = {}
     for event in events:
         vis = HistoryVisibility.SHARED
         state_ids = event_to_state_ids.get(event.event_id)
@@ -780,7 +774,7 @@ async def _event_to_history_vis(
 
 async def _event_to_memberships(
     storage: StorageControllers, events: Collection[EventBase], server_name: str
-) -> Dict[str, StateMap[Tuple[str, str]]]:
+) -> dict[str, StateMap[tuple[str, str]]]:
     """Get the remote membership list at each of the given events
 
     Returns a map from event id to state map, which will contain only membership events
diff --git a/synmark/__main__.py b/synmark/__main__.py
index 82717c4fc7..5308c96012 100644
--- a/synmark/__main__.py
+++ b/synmark/__main__.py
@@ -22,7 +22,7 @@ import sys
 from argparse import REMAINDER, Namespace
 from contextlib import redirect_stderr
 from io import StringIO
-from typing import Any, Callable, Coroutine, List, TypeVar
+from typing import Any, Callable, Coroutine, TypeVar
 
 import pyperf
 
@@ -76,7 +76,7 @@ def make_test(
 
 if __name__ == "__main__":
 
-    def add_cmdline_args(cmd: List[str], args: Namespace) -> None:
+    def add_cmdline_args(cmd: list[str], args: Namespace) -> None:
         if args.log:
             cmd.extend(["--log"])
         cmd.extend(args.tests)
diff --git a/synmark/suites/logging.py b/synmark/suites/logging.py
index c3f3cceaa6..d89f487d3d 100644
--- a/synmark/suites/logging.py
+++ b/synmark/suites/logging.py
@@ -22,7 +22,6 @@ import logging
 import logging.config
 import warnings
 from io import StringIO
-from typing import Optional
 from unittest.mock import Mock
 
 from pyperf import perf_counter
@@ -33,7 +32,7 @@ from twisted.internet.protocol import ServerFactory
 from twisted.logger import LogBeginner, LogPublisher
 from twisted.protocols.basic import LineOnlyReceiver
 
-from synapse.config.logger import _setup_stdlib_logging
+from synapse.config.logger import _setup_stdlib_logging, one_time_logging_setup
 from synapse.logging import RemoteHandler
 from synapse.synapse_rust import reset_logging_config
 from synapse.types import ISynapseReactor
@@ -58,7 +57,7 @@ class LineCounter(LineOnlyReceiver):
 class Factory(ServerFactory):
     protocol = LineCounter
     wait_for: int
-    on_done: Optional[Deferred]
+    on_done: Deferred | None
 
 
 async def main(reactor: ISynapseReactor, loops: int) -> float:
@@ -86,7 +85,9 @@ async def main(reactor: ISynapseReactor, loops: int) -> float:
     hs_config = Config()
 
     # To be able to sleep.
-    clock = Clock(reactor, server_name=hs_config.server.server_name)
+    # Ignore linter error here since we are running outside of the context of a
+    # Synapse `HomeServer`.
+    clock = Clock(reactor, server_name=hs_config.server.server_name)  # type: ignore[multiple-internal-clocks]
 
     errors = StringIO()
     publisher = LogPublisher()
@@ -113,10 +114,10 @@ async def main(reactor: ISynapseReactor, loops: int) -> float:
     }
 
     logger = logging.getLogger("synapse")
+    one_time_logging_setup(logBeginner=beginner)
     _setup_stdlib_logging(
         hs_config,  # type: ignore[arg-type]
         None,
-        logBeginner=beginner,
     )
 
     # Force a new logging config without having to load it from a file.
diff --git a/synmark/suites/lrucache.py b/synmark/suites/lrucache.py
index 6314035bd7..830a3daa8f 100644
--- a/synmark/suites/lrucache.py
+++ b/synmark/suites/lrucache.py
@@ -23,14 +23,19 @@ from pyperf import perf_counter
 
 from synapse.types import ISynapseReactor
 from synapse.util.caches.lrucache import LruCache
+from synapse.util.clock import Clock
 
 
 async def main(reactor: ISynapseReactor, loops: int) -> float:
     """
     Benchmark `loops` number of insertions into LruCache without eviction.
     """
+    # Ignore linter error here since we are running outside of the context of a
+    # Synapse `HomeServer`.
     cache: LruCache[int, bool] = LruCache(
-        max_size=loops, server_name="synmark_benchmark"
+        max_size=loops,
+        clock=Clock(reactor, server_name="synmark_benchmark"),  # type: ignore[multiple-internal-clocks]
+        server_name="synmark_benchmark",
     )
 
     start = perf_counter()
diff --git a/synmark/suites/lrucache_evict.py b/synmark/suites/lrucache_evict.py
index b8cd589697..c67e0c9001 100644
--- a/synmark/suites/lrucache_evict.py
+++ b/synmark/suites/lrucache_evict.py
@@ -23,6 +23,7 @@ from pyperf import perf_counter
 
 from synapse.types import ISynapseReactor
 from synapse.util.caches.lrucache import LruCache
+from synapse.util.clock import Clock
 
 
 async def main(reactor: ISynapseReactor, loops: int) -> float:
@@ -30,8 +31,12 @@ async def main(reactor: ISynapseReactor, loops: int) -> float:
     Benchmark `loops` number of insertions into LruCache where half of them are
     evicted.
     """
+    # Ignore linter error here since we are running outside of the context of a
+    # Synapse `HomeServer`.
     cache: LruCache[int, bool] = LruCache(
-        max_size=loops // 2, server_name="synmark_benchmark"
+        max_size=loops // 2,
+        clock=Clock(reactor, server_name="synmark_benchmark"),  # type: ignore[multiple-internal-clocks]
+        server_name="synmark_benchmark",
     )
 
     start = perf_counter()
diff --git a/tests/api/test_auth.py b/tests/api/test_auth.py
index e7fcd928d7..f7905ced7e 100644
--- a/tests/api/test_auth.py
+++ b/tests/api/test_auth.py
@@ -42,7 +42,6 @@ from synapse.types import Requester, UserID
 from synapse.util.clock import Clock
 
 from tests import unittest
-from tests.unittest import override_config
 from tests.utils import mock_getRawHeaders
 
 
@@ -237,7 +236,6 @@ class AuthTestCase(unittest.HomeserverTestCase):
         request.requestHeaders.getRawHeaders = mock_getRawHeaders()
         self.get_failure(self.auth.get_user_by_req(request), AuthError)
 
-    @override_config({"experimental_features": {"msc3202_device_masquerading": True}})
     def test_get_user_by_req_appservice_valid_token_valid_device_id(self) -> None:
         """
         Tests that when an application service passes the device_id URL parameter
@@ -264,7 +262,7 @@ class AuthTestCase(unittest.HomeserverTestCase):
         request.getClientAddress.return_value.host = "127.0.0.1"
         request.args[b"access_token"] = [self.test_token]
         request.args[b"user_id"] = [masquerading_user_id]
-        request.args[b"org.matrix.msc3202.device_id"] = [masquerading_device_id]
+        request.args[b"device_id"] = [masquerading_device_id]
         request.requestHeaders.getRawHeaders = mock_getRawHeaders()
         requester = self.get_success(self.auth.get_user_by_req(request))
         self.assertEqual(
@@ -272,7 +270,6 @@ class AuthTestCase(unittest.HomeserverTestCase):
         )
         self.assertEqual(requester.device_id, masquerading_device_id.decode("utf8"))
 
-    @override_config({"experimental_features": {"msc3202_device_masquerading": True}})
     def test_get_user_by_req_appservice_valid_token_invalid_device_id(self) -> None:
         """
         Tests that when an application service passes the device_id URL parameter
@@ -299,7 +296,7 @@ class AuthTestCase(unittest.HomeserverTestCase):
         request.getClientAddress.return_value.host = "127.0.0.1"
         request.args[b"access_token"] = [self.test_token]
         request.args[b"user_id"] = [masquerading_user_id]
-        request.args[b"org.matrix.msc3202.device_id"] = [masquerading_device_id]
+        request.args[b"device_id"] = [masquerading_device_id]
         request.requestHeaders.getRawHeaders = mock_getRawHeaders()
 
         failure = self.get_failure(self.auth.get_user_by_req(request), AuthError)
diff --git a/tests/api/test_filtering.py b/tests/api/test_filtering.py
index d74878a4e1..7742a06b4c 100644
--- a/tests/api/test_filtering.py
+++ b/tests/api/test_filtering.py
@@ -20,7 +20,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import List
 from unittest.mock import patch
 
 import jsonschema
@@ -50,7 +49,7 @@ class FilteringTestCase(unittest.HomeserverTestCase):
 
     def test_errors_on_invalid_filters(self) -> None:
         # See USER_FILTER_SCHEMA for the filter schema.
-        invalid_filters: List[JsonDict] = [
+        invalid_filters: list[JsonDict] = [
             # `account_data` must be a dictionary
             {"account_data": "Hello World"},
             # `event_format` must be "client" or "federation"
@@ -67,7 +66,7 @@ class FilteringTestCase(unittest.HomeserverTestCase):
     def test_ignores_unknown_filter_fields(self) -> None:
         # For forward compatibility, we must ignore unknown filter fields.
         # See USER_FILTER_SCHEMA for the filter schema.
-        filters: List[JsonDict] = [
+        filters: list[JsonDict] = [
             {"org.matrix.msc9999.future_option": True},
             {"presence": {"org.matrix.msc9999.future_option": True}},
             {"room": {"org.matrix.msc9999.future_option": True}},
@@ -78,7 +77,7 @@ class FilteringTestCase(unittest.HomeserverTestCase):
             # Must not raise.
 
     def test_valid_filters(self) -> None:
-        valid_filters: List[JsonDict] = [
+        valid_filters: list[JsonDict] = [
             {
                 "room": {
                     "timeline": {"limit": 20},
@@ -557,7 +556,7 @@ class FilteringTestCase(unittest.HomeserverTestCase):
                 room_id="!foo:bar",
             ),
         ]
-        jsondicts: List[JsonDict] = [{}]
+        jsondicts: list[JsonDict] = [{}]
 
         # For the following tests we patch the datastore method (intead of injecting
         # events). This is a bit cheeky, but tests the logic of _check_event_relations.
@@ -565,7 +564,7 @@ class FilteringTestCase(unittest.HomeserverTestCase):
         # Filter for a particular sender.
         definition = {"related_by_senders": ["@foo:bar"]}
 
-        async def events_have_relations(*args: object, **kwargs: object) -> List[str]:
+        async def events_have_relations(*args: object, **kwargs: object) -> list[str]:
             return ["$with_relation"]
 
         with patch.object(
diff --git a/tests/api/test_ratelimiting.py b/tests/api/test_ratelimiting.py
index 2e45d4e4d2..0ef537841d 100644
--- a/tests/api/test_ratelimiting.py
+++ b/tests/api/test_ratelimiting.py
@@ -1,5 +1,3 @@
-from typing import Optional
-
 from synapse.api.ratelimiting import LimitExceededError, Ratelimiter
 from synapse.appservice import ApplicationService
 from synapse.config.ratelimiting import RatelimitSettings
@@ -228,6 +226,21 @@ class TestRatelimiter(unittest.HomeserverTestCase):
 
         self.assertNotIn("test_id_1", limiter.actions)
 
+    def test_pruning_record_action(self) -> None:
+        """Test that entries added by record_action also get pruned."""
+        limiter = Ratelimiter(
+            store=self.hs.get_datastores().main,
+            clock=self.clock,
+            cfg=RatelimitSettings(key="", per_second=0.1, burst_count=1),
+        )
+        limiter.record_action(None, key="test_id_1", n_actions=1, _time_now_s=0)
+
+        self.assertIn("test_id_1", limiter.actions)
+
+        self.reactor.advance(60)
+
+        self.assertNotIn("test_id_1", limiter.actions)
+
     def test_db_user_override(self) -> None:
         """Test that users that have ratelimiting disabled in the DB aren't
         ratelimited.
@@ -474,7 +487,7 @@ class TestRatelimiter(unittest.HomeserverTestCase):
         # and limiter name.
         async def get_ratelimit_override_for_user(
             user_id: str, limiter_name: str
-        ) -> Optional[RatelimitOverride]:
+        ) -> RatelimitOverride | None:
             if user_id == test_user_id:
                 return RatelimitOverride(
                     per_second=0.1,
diff --git a/tests/app/test_homeserver_shutdown.py b/tests/app/test_homeserver_shutdown.py
new file mode 100644
index 0000000000..f127e5571d
--- /dev/null
+++ b/tests/app/test_homeserver_shutdown.py
@@ -0,0 +1,206 @@
+#
+# This file is licensed under the Affero General Public License (AGPL) version 3.
+#
+# Copyright (C) 2025 New Vector, Ltd
+#
+# This program is free software: you can redistribute it and/or modify
+# it under the terms of the GNU Affero General Public License as
+# published by the Free Software Foundation, either version 3 of the
+# License, or (at your option) any later version.
+#
+# See the GNU Affero General Public License for more details:
+# <https://www.gnu.org/licenses/agpl-3.0.html>.
+#
+# Originally licensed under the Apache License, Version 2.0:
+# <http://www.apache.org/licenses/LICENSE-2.0>.
+#
+# [This file includes modifications made by New Vector Limited]
+#
+#
+
+import gc
+import weakref
+
+from synapse.app.homeserver import SynapseHomeServer
+from synapse.logging.context import LoggingContext
+from synapse.storage.background_updates import UpdaterStatus
+
+from tests.server import (
+    cleanup_test_reactor_system_event_triggers,
+    get_clock,
+    setup_test_homeserver,
+)
+from tests.unittest import HomeserverTestCase, logcontext_clean
+
+
+class HomeserverCleanShutdownTestCase(HomeserverTestCase):
+    def setUp(self) -> None:
+        pass
+
+    # NOTE: ideally we'd have another test to ensure we properly shutdown with
+    # real in-flight HTTP requests since those result in additional resources being
+    # setup that hold strong references to the homeserver.
+    # Mainly, the HTTP channel created by a real TCP connection from client to server
+    # is held open between requests and care needs to be taken in Twisted to ensure it is properly
+    # closed in a timely manner during shutdown. Simulating this behaviour in a unit test
+    # won't be as good as a proper integration test in complement.
+
+    @logcontext_clean
+    def test_clean_homeserver_shutdown(self) -> None:
+        """Ensure the `SynapseHomeServer` can be fully shutdown and garbage collected"""
+        self.reactor, self.clock = get_clock()
+        self.hs = setup_test_homeserver(
+            cleanup_func=self.addCleanup,
+            reactor=self.reactor,
+            homeserver_to_use=SynapseHomeServer,
+            clock=self.clock,
+        )
+        self.wait_for_background_updates()
+
+        hs_ref = weakref.ref(self.hs)
+
+        # Run the reactor so any `callWhenRunning` functions can be cleared out.
+        self.reactor.run()
+        # This would normally happen as part of `HomeServer.shutdown` but the `MemoryReactor`
+        # we use in tests doesn't handle this properly (see doc comment)
+        cleanup_test_reactor_system_event_triggers(self.reactor)
+
+        async def shutdown() -> None:
+            # Use a logcontext just to double-check that we don't mangle the logcontext
+            # during shutdown.
+            with LoggingContext(name="hs_shutdown", server_name=self.hs.hostname):
+                await self.hs.shutdown()
+
+        self.get_success(shutdown())
+
+        # Cleanup the internal reference in our test case
+        del self.hs
+
+        # Force garbage collection.
+        gc.collect()
+
+        # Ensure the `HomeServer` hs been garbage collected by attempting to use the
+        # weakref to it.
+        if hs_ref() is not None:
+            self.fail("HomeServer reference should not be valid at this point")
+
+            # To help debug this test when it fails, it is useful to leverage the
+            # `objgraph` module.
+            # The following code serves as an example of what I have found to be useful
+            # when tracking down references holding the `SynapseHomeServer` in memory:
+            #
+            # all_objects = gc.get_objects()
+            # for obj in all_objects:
+            #     try:
+            #         # These are a subset of types that are typically involved with
+            #         # holding the `HomeServer` in memory. You may want to inspect
+            #         # other types as well.
+            #         if isinstance(obj, DataStore):
+            #             print(sys.getrefcount(obj), "refs to", obj)
+            #             if not isinstance(obj, weakref.ProxyType):
+            #                 db_obj = obj
+            #         if isinstance(obj, SynapseHomeServer):
+            #             print(sys.getrefcount(obj), "refs to", obj)
+            #             if not isinstance(obj, weakref.ProxyType):
+            #                 synapse_hs = obj
+            #         if isinstance(obj, SynapseSite):
+            #             print(sys.getrefcount(obj), "refs to", obj)
+            #             if not isinstance(obj, weakref.ProxyType):
+            #                 sysite = obj
+            #         if isinstance(obj, DatabasePool):
+            #             print(sys.getrefcount(obj), "refs to", obj)
+            #             if not isinstance(obj, weakref.ProxyType):
+            #                 dbpool = obj
+            #     except Exception:
+            #         pass
+            #
+            # print(sys.getrefcount(hs_ref()), "refs to", hs_ref())
+            #
+            # # The following values for `max_depth` and `too_many` have been found to
+            # # render a useful amount of information without taking an overly long time
+            # # to generate the result.
+            # objgraph.show_backrefs(synapse_hs, max_depth=10, too_many=10)
+
+    @logcontext_clean
+    def test_clean_homeserver_shutdown_mid_background_updates(self) -> None:
+        """Ensure the `SynapseHomeServer` can be fully shutdown and garbage collected
+        before background updates have completed"""
+        self.reactor, self.clock = get_clock()
+        self.hs = setup_test_homeserver(
+            cleanup_func=self.addCleanup,
+            reactor=self.reactor,
+            homeserver_to_use=SynapseHomeServer,
+            clock=self.clock,
+        )
+
+        # Pump the background updates by a single iteration, just to ensure any extra
+        # resources it uses have been started.
+        store = weakref.proxy(self.hs.get_datastores().main)
+        self.get_success(store.db_pool.updates.do_next_background_update(False), by=0.1)
+
+        hs_ref = weakref.ref(self.hs)
+
+        # Run the reactor so any `callWhenRunning` functions can be cleared out.
+        self.reactor.run()
+        # This would normally happen as part of `HomeServer.shutdown` but the `MemoryReactor`
+        # we use in tests doesn't handle this properly (see doc comment)
+        cleanup_test_reactor_system_event_triggers(self.reactor)
+
+        # Ensure the background updates are not complete.
+        self.assertNotEqual(store.db_pool.updates.get_status(), UpdaterStatus.COMPLETE)
+
+        async def shutdown() -> None:
+            # Use a logcontext just to double-check that we don't mangle the logcontext
+            # during shutdown.
+            with LoggingContext(name="hs_shutdown", server_name=self.hs.hostname):
+                await self.hs.shutdown()
+
+        self.get_success(shutdown())
+
+        # Cleanup the internal reference in our test case
+        del self.hs
+
+        # Force garbage collection.
+        gc.collect()
+
+        # Ensure the `HomeServer` hs been garbage collected by attempting to use the
+        # weakref to it.
+        if hs_ref() is not None:
+            self.fail("HomeServer reference should not be valid at this point")
+
+            # To help debug this test when it fails, it is useful to leverage the
+            # `objgraph` module.
+            # The following code serves as an example of what I have found to be useful
+            # when tracking down references holding the `SynapseHomeServer` in memory:
+            #
+            # all_objects = gc.get_objects()
+            # for obj in all_objects:
+            #     try:
+            #         # These are a subset of types that are typically involved with
+            #         # holding the `HomeServer` in memory. You may want to inspect
+            #         # other types as well.
+            #         if isinstance(obj, DataStore):
+            #             print(sys.getrefcount(obj), "refs to", obj)
+            #             if not isinstance(obj, weakref.ProxyType):
+            #                 db_obj = obj
+            #         if isinstance(obj, SynapseHomeServer):
+            #             print(sys.getrefcount(obj), "refs to", obj)
+            #             if not isinstance(obj, weakref.ProxyType):
+            #                 synapse_hs = obj
+            #         if isinstance(obj, SynapseSite):
+            #             print(sys.getrefcount(obj), "refs to", obj)
+            #             if not isinstance(obj, weakref.ProxyType):
+            #                 sysite = obj
+            #         if isinstance(obj, DatabasePool):
+            #             print(sys.getrefcount(obj), "refs to", obj)
+            #             if not isinstance(obj, weakref.ProxyType):
+            #                 dbpool = obj
+            #     except Exception:
+            #         pass
+            #
+            # print(sys.getrefcount(hs_ref()), "refs to", hs_ref())
+            #
+            # # The following values for `max_depth` and `too_many` have been found to
+            # # render a useful amount of information without taking an overly long time
+            # # to generate the result.
+            # objgraph.show_backrefs(synapse_hs, max_depth=10, too_many=10)
diff --git a/tests/app/test_homeserver_start.py b/tests/app/test_homeserver_start.py
index 0d257c98aa..36a7170d12 100644
--- a/tests/app/test_homeserver_start.py
+++ b/tests/app/test_homeserver_start.py
@@ -37,7 +37,13 @@ class HomeserverAppStartTestCase(ConfigFileTestCase):
         self.add_lines_to_config(["  main:", "    host: 127.0.0.1", "    port: 1234"])
         # Ensure that starting master process with worker config raises an exception
         with self.assertRaises(ConfigError):
+            # Do a normal homeserver creation and setup
             homeserver_config = synapse.app.homeserver.load_or_generate_config(
                 ["-c", self.config_file]
             )
-            synapse.app.homeserver.setup(homeserver_config)
+            # XXX: The error will be raised at this point
+            hs = synapse.app.homeserver.create_homeserver(homeserver_config)
+            # Continue with the setup. We don't expect this to run because we raised
+            # earlier, but in the future, the code could be refactored to raise the
+            # error in a different place.
+            synapse.app.homeserver.setup(hs)
diff --git a/tests/app/test_openid_listener.py b/tests/app/test_openid_listener.py
index 6ca514d557..6a1a630fe8 100644
--- a/tests/app/test_openid_listener.py
+++ b/tests/app/test_openid_listener.py
@@ -17,7 +17,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import List
 from unittest.mock import Mock, patch
 
 from parameterized import parameterized
@@ -58,7 +57,7 @@ class FederationReaderOpenIDListenerTests(HomeserverTestCase):
             (["openid"], "auth_fail"),
         ]
     )
-    def test_openid_listener(self, names: List[str], expectation: str) -> None:
+    def test_openid_listener(self, names: list[str], expectation: str) -> None:
         """
         Test different openid listener configurations.
 
@@ -106,7 +105,7 @@ class SynapseHomeserverOpenIDListenerTests(HomeserverTestCase):
             (["openid"], "auth_fail"),
         ]
     )
-    def test_openid_listener(self, names: List[str], expectation: str) -> None:
+    def test_openid_listener(self, names: list[str], expectation: str) -> None:
         """
         Test different openid listener configurations.
 
diff --git a/tests/appservice/test_api.py b/tests/appservice/test_api.py
index 085dfd2d1d..bf55f261bb 100644
--- a/tests/appservice/test_api.py
+++ b/tests/appservice/test_api.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Any, List, Mapping, Optional, Sequence, Union
+from typing import Any, Mapping, Sequence
 from unittest.mock import Mock
 
 from twisted.internet.testing import MemoryReactor
@@ -80,8 +80,8 @@ class ApplicationServiceApiTestCase(unittest.HomeserverTestCase):
         async def get_json(
             url: str,
             args: Mapping[Any, Any],
-            headers: Mapping[Union[str, bytes], Sequence[Union[str, bytes]]],
-        ) -> List[JsonDict]:
+            headers: Mapping[str | bytes, Sequence[str | bytes]],
+        ) -> list[JsonDict]:
             # Ensure the access token is passed as a header.
             if not headers or not headers.get(b"Authorization"):
                 raise RuntimeError("Access token not provided")
@@ -154,10 +154,8 @@ class ApplicationServiceApiTestCase(unittest.HomeserverTestCase):
         async def get_json(
             url: str,
             args: Mapping[Any, Any],
-            headers: Optional[
-                Mapping[Union[str, bytes], Sequence[Union[str, bytes]]]
-            ] = None,
-        ) -> List[JsonDict]:
+            headers: Mapping[str | bytes, Sequence[str | bytes]] | None = None,
+        ) -> list[JsonDict]:
             # Ensure the access token is passed as a both a query param and in the headers.
             if not args.get(b"access_token"):
                 raise RuntimeError("Access token should be provided in query params.")
@@ -216,7 +214,7 @@ class ApplicationServiceApiTestCase(unittest.HomeserverTestCase):
         async def post_json_get_json(
             uri: str,
             post_json: Any,
-            headers: Mapping[Union[str, bytes], Sequence[Union[str, bytes]]],
+            headers: Mapping[str | bytes, Sequence[str | bytes]],
         ) -> JsonDict:
             # Ensure the access token is passed as both a header and query arg.
             if not headers.get(b"Authorization"):
diff --git a/tests/appservice/test_scheduler.py b/tests/appservice/test_scheduler.py
index 9498ea1279..3caf006386 100644
--- a/tests/appservice/test_scheduler.py
+++ b/tests/appservice/test_scheduler.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import List, Optional, Sequence, Tuple, cast
+from typing import Sequence
 from unittest.mock import AsyncMock, Mock
 
 from typing_extensions import TypeAlias
@@ -44,13 +44,12 @@ from synapse.types import DeviceListUpdates, JsonDict
 from synapse.util.clock import Clock
 
 from tests import unittest
-
-from ..utils import MockClock
+from tests.server import get_clock
 
 
 class ApplicationServiceSchedulerTransactionCtrlTestCase(unittest.TestCase):
     def setUp(self) -> None:
-        self.clock = MockClock()
+        self.reactor, self.clock = get_clock()
         self.store = Mock()
         self.as_api = Mock()
 
@@ -168,16 +167,18 @@ class ApplicationServiceSchedulerTransactionCtrlTestCase(unittest.TestCase):
         )
 
 
-class ApplicationServiceSchedulerRecovererTestCase(unittest.TestCase):
+class ApplicationServiceSchedulerRecovererTestCase(unittest.HomeserverTestCase):
     def setUp(self) -> None:
-        self.clock = MockClock()
+        super().setUp()
+        self.reactor, self.clock = get_clock()
         self.as_api = Mock()
         self.store = Mock()
         self.service = Mock()
         self.callback = AsyncMock()
         self.recoverer = _Recoverer(
             server_name="test_server",
-            clock=cast(Clock, self.clock),
+            hs=self.hs,
+            clock=self.clock,
             as_api=self.as_api,
             store=self.store,
             service=self.service,
@@ -189,9 +190,7 @@ class ApplicationServiceSchedulerRecovererTestCase(unittest.TestCase):
         # return one txn to send, then no more old txns
         txns = [txn, None]
 
-        def take_txn(
-            *args: object, **kwargs: object
-        ) -> "defer.Deferred[Optional[Mock]]":
+        def take_txn(*args: object, **kwargs: object) -> "defer.Deferred[Mock | None]":
             return defer.succeed(txns.pop(0))
 
         self.store.get_oldest_unsent_txn = Mock(side_effect=take_txn)
@@ -202,7 +201,7 @@ class ApplicationServiceSchedulerRecovererTestCase(unittest.TestCase):
         txn.send = AsyncMock(return_value=True)
         txn.complete = AsyncMock(return_value=None)
         # wait for exp backoff
-        self.clock.advance_time(2)
+        self.reactor.advance(2)
         self.assertEqual(1, txn.send.call_count)
         self.assertEqual(1, txn.complete.call_count)
         # 2 because it needs to get None to know there are no more txns
@@ -215,9 +214,7 @@ class ApplicationServiceSchedulerRecovererTestCase(unittest.TestCase):
         txns = [txn, None]
         pop_txn = False
 
-        def take_txn(
-            *args: object, **kwargs: object
-        ) -> "defer.Deferred[Optional[Mock]]":
+        def take_txn(*args: object, **kwargs: object) -> "defer.Deferred[Mock | None]":
             if pop_txn:
                 return defer.succeed(txns.pop(0))
             else:
@@ -229,21 +226,21 @@ class ApplicationServiceSchedulerRecovererTestCase(unittest.TestCase):
         self.assertEqual(0, self.store.get_oldest_unsent_txn.call_count)
         txn.send = AsyncMock(return_value=False)
         txn.complete = AsyncMock(return_value=None)
-        self.clock.advance_time(2)
+        self.reactor.advance(2)
         self.assertEqual(1, txn.send.call_count)
         self.assertEqual(0, txn.complete.call_count)
         self.assertEqual(0, self.callback.call_count)
-        self.clock.advance_time(4)
+        self.reactor.advance(4)
         self.assertEqual(2, txn.send.call_count)
         self.assertEqual(0, txn.complete.call_count)
         self.assertEqual(0, self.callback.call_count)
-        self.clock.advance_time(8)
+        self.reactor.advance(8)
         self.assertEqual(3, txn.send.call_count)
         self.assertEqual(0, txn.complete.call_count)
         self.assertEqual(0, self.callback.call_count)
         txn.send = AsyncMock(return_value=True)  # successfully send the txn
         pop_txn = True  # returns the txn the first time, then no more.
-        self.clock.advance_time(16)
+        self.reactor.advance(16)
         self.assertEqual(1, txn.send.call_count)  # new mock reset call count
         self.assertEqual(1, txn.complete.call_count)
         self.callback.assert_called_once_with(self.recoverer)
@@ -253,9 +250,7 @@ class ApplicationServiceSchedulerRecovererTestCase(unittest.TestCase):
         txns = [txn, None]
         pop_txn = False
 
-        def take_txn(
-            *args: object, **kwargs: object
-        ) -> "defer.Deferred[Optional[Mock]]":
+        def take_txn(*args: object, **kwargs: object) -> "defer.Deferred[Mock | None]":
             if pop_txn:
                 return defer.succeed(txns.pop(0))
             else:
@@ -268,7 +263,7 @@ class ApplicationServiceSchedulerRecovererTestCase(unittest.TestCase):
         self.assertEqual(0, self.store.get_oldest_unsent_txn.call_count)
         txn.send = AsyncMock(return_value=False)
         txn.complete = AsyncMock(return_value=None)
-        self.clock.advance_time(2)
+        self.reactor.advance(2)
         self.assertEqual(1, txn.send.call_count)
         self.assertEqual(0, txn.complete.call_count)
         self.assertEqual(0, self.callback.call_count)
@@ -287,14 +282,14 @@ class ApplicationServiceSchedulerRecovererTestCase(unittest.TestCase):
 # Corresponds to synapse.appservice.scheduler._TransactionController.send
 TxnCtrlArgs: TypeAlias = """
 defer.Deferred[
-    Tuple[
+    tuple[
         ApplicationService,
         Sequence[EventBase],
-        Optional[List[JsonDict]],
-        Optional[List[JsonDict]],
-        Optional[TransactionOneTimeKeysCount],
-        Optional[TransactionUnusedFallbackKeys],
-        Optional[DeviceListUpdates],
+        list[JsonDict] | None,
+        list[JsonDict] | None,
+        TransactionOneTimeKeysCount | None,
+        TransactionUnusedFallbackKeys | None,
+        DeviceListUpdates | None,
     ]
 ]
 """
diff --git a/tests/config/test_cache.py b/tests/config/test_cache.py
index f56d6044a9..74db2dab08 100644
--- a/tests/config/test_cache.py
+++ b/tests/config/test_cache.py
@@ -24,6 +24,7 @@ from synapse.config.cache import CacheConfig, add_resizable_cache
 from synapse.types import JsonDict
 from synapse.util.caches.lrucache import LruCache
 
+from tests.server import get_clock
 from tests.unittest import TestCase
 
 
@@ -32,6 +33,7 @@ class CacheConfigTests(TestCase):
         # Reset caches before each test since there's global state involved.
         self.config = CacheConfig(RootConfig())
         self.config.reset()
+        _, self.clock = get_clock()
 
     def tearDown(self) -> None:
         # Also reset the caches after each test to leave state pristine.
@@ -75,7 +77,9 @@ class CacheConfigTests(TestCase):
         the default cache size in the interim, and then resized once the config
         is loaded.
         """
-        cache: LruCache = LruCache(max_size=100, server_name="test_server")
+        cache: LruCache = LruCache(
+            max_size=100, clock=self.clock, server_name="test_server"
+        )
 
         add_resizable_cache("foo", cache_resize_callback=cache.set_cache_factor)
         self.assertEqual(cache.max_size, 50)
@@ -96,7 +100,9 @@ class CacheConfigTests(TestCase):
         self.config.read_config(config, config_dir_path="", data_dir_path="")
         self.config.resize_all_caches()
 
-        cache: LruCache = LruCache(max_size=100, server_name="test_server")
+        cache: LruCache = LruCache(
+            max_size=100, clock=self.clock, server_name="test_server"
+        )
         add_resizable_cache("foo", cache_resize_callback=cache.set_cache_factor)
         self.assertEqual(cache.max_size, 200)
 
@@ -106,7 +112,9 @@ class CacheConfigTests(TestCase):
         the default cache size in the interim, and then resized to the new
         default cache size once the config is loaded.
         """
-        cache: LruCache = LruCache(max_size=100, server_name="test_server")
+        cache: LruCache = LruCache(
+            max_size=100, clock=self.clock, server_name="test_server"
+        )
         add_resizable_cache("foo", cache_resize_callback=cache.set_cache_factor)
         self.assertEqual(cache.max_size, 50)
 
@@ -126,7 +134,9 @@ class CacheConfigTests(TestCase):
         self.config.read_config(config, config_dir_path="", data_dir_path="")
         self.config.resize_all_caches()
 
-        cache: LruCache = LruCache(max_size=100, server_name="test_server")
+        cache: LruCache = LruCache(
+            max_size=100, clock=self.clock, server_name="test_server"
+        )
         add_resizable_cache("foo", cache_resize_callback=cache.set_cache_factor)
         self.assertEqual(cache.max_size, 150)
 
@@ -145,15 +155,21 @@ class CacheConfigTests(TestCase):
         self.config.read_config(config, config_dir_path="", data_dir_path="")
         self.config.resize_all_caches()
 
-        cache_a: LruCache = LruCache(max_size=100, server_name="test_server")
+        cache_a: LruCache = LruCache(
+            max_size=100, clock=self.clock, server_name="test_server"
+        )
         add_resizable_cache("*cache_a*", cache_resize_callback=cache_a.set_cache_factor)
         self.assertEqual(cache_a.max_size, 200)
 
-        cache_b: LruCache = LruCache(max_size=100, server_name="test_server")
+        cache_b: LruCache = LruCache(
+            max_size=100, clock=self.clock, server_name="test_server"
+        )
         add_resizable_cache("*Cache_b*", cache_resize_callback=cache_b.set_cache_factor)
         self.assertEqual(cache_b.max_size, 300)
 
-        cache_c: LruCache = LruCache(max_size=100, server_name="test_server")
+        cache_c: LruCache = LruCache(
+            max_size=100, clock=self.clock, server_name="test_server"
+        )
         add_resizable_cache("*cache_c*", cache_resize_callback=cache_c.set_cache_factor)
         self.assertEqual(cache_c.max_size, 200)
 
@@ -168,6 +184,7 @@ class CacheConfigTests(TestCase):
 
         cache: LruCache = LruCache(
             max_size=self.config.event_cache_size,
+            clock=self.clock,
             apply_cache_factor_from_config=False,
             server_name="test_server",
         )
diff --git a/tests/config/test_load.py b/tests/config/test_load.py
index b72365b6e3..c1b787346e 100644
--- a/tests/config/test_load.py
+++ b/tests/config/test_load.py
@@ -99,7 +99,14 @@ class ConfigLoadingFileTestCase(ConfigFileTestCase):
     def test_disable_registration(self) -> None:
         self.generate_config()
         self.add_lines_to_config(
-            ["enable_registration: true", "disable_registration: true"]
+            [
+                "enable_registration: true",
+                "disable_registration: true",
+                # We're not worried about open registration in this test. This test is
+                # focused on making sure that enable/disable_registration properly
+                # override each other.
+                "enable_registration_without_verification: true",
+            ]
         )
         # Check that disable_registration clobbers enable_registration.
         config = HomeServerConfig.load_config("", ["-c", self.config_file])
diff --git a/tests/config/test_oauth_delegation.py b/tests/config/test_oauth_delegation.py
index 833cfe628b..6105ca2b04 100644
--- a/tests/config/test_oauth_delegation.py
+++ b/tests/config/test_oauth_delegation.py
@@ -21,6 +21,7 @@
 
 import os
 import tempfile
+from pathlib import Path
 from unittest.mock import Mock
 
 from synapse.config import ConfigError
@@ -231,7 +232,10 @@ class MSC3861OAuthDelegation(TestCase):
         reactor, clock = get_clock()
         with self.assertRaises(ConfigError):
             setup_test_homeserver(
-                self.addCleanup, reactor=reactor, clock=clock, config=config
+                cleanup_func=self.addCleanup,
+                config=config,
+                reactor=reactor,
+                clock=clock,
             )
 
     def test_jwt_auth_cannot_be_enabled(self) -> None:
@@ -306,7 +310,9 @@ class MasAuthDelegation(TestCase):
     def test_secret_and_secret_path_are_mutually_exclusive(self) -> None:
         with tempfile.NamedTemporaryFile() as f:
             self.config_dict["matrix_authentication_service"]["secret"] = "verysecret"
-            self.config_dict["matrix_authentication_service"]["secret_path"] = f.name
+            self.config_dict["matrix_authentication_service"]["secret_path"] = Path(
+                f.name
+            )
             with self.assertRaises(ConfigError):
                 self.parse_config()
 
@@ -314,13 +320,15 @@ class MasAuthDelegation(TestCase):
         with tempfile.NamedTemporaryFile(buffering=0) as f:
             f.write(b"53C237")
             del self.config_dict["matrix_authentication_service"]["secret"]
-            self.config_dict["matrix_authentication_service"]["secret_path"] = f.name
+            self.config_dict["matrix_authentication_service"]["secret_path"] = Path(
+                f.name
+            )
             config = self.parse_config()
             self.assertEqual(config.mas.secret(), "53C237")
 
     def test_secret_path_must_exist(self) -> None:
         del self.config_dict["matrix_authentication_service"]["secret"]
-        self.config_dict["matrix_authentication_service"]["secret_path"] = (
+        self.config_dict["matrix_authentication_service"]["secret_path"] = Path(
             "/not/a/valid/file"
         )
         with self.assertRaises(ConfigError):
@@ -395,7 +403,10 @@ class MasAuthDelegation(TestCase):
         reactor, clock = get_clock()
         with self.assertRaises(ConfigError):
             setup_test_homeserver(
-                self.addCleanup, reactor=reactor, clock=clock, config=config
+                cleanup_func=self.addCleanup,
+                config=config,
+                reactor=reactor,
+                clock=clock,
             )
 
     @skip_unless(HAS_AUTHLIB, "requires authlib")
diff --git a/tests/config/test_registration_config.py b/tests/config/test_registration_config.py
index a8520c91d1..9eb5323a24 100644
--- a/tests/config/test_registration_config.py
+++ b/tests/config/test_registration_config.py
@@ -19,6 +19,8 @@
 #
 #
 
+import argparse
+
 import synapse.app.homeserver
 from synapse.config import ConfigError
 from synapse.config.homeserver import HomeServerConfig
@@ -99,6 +101,39 @@ class RegistrationConfigTestCase(ConfigFileTestCase):
         )
 
     def test_refuse_to_start_if_open_registration_and_no_verification(self) -> None:
+        """
+        Test that our utilities to start the main Synapse homeserver process refuses
+        to start if we detect open registration.
+        """
+        self.generate_config()
+        self.add_lines_to_config(
+            [
+                " ",
+                "enable_registration: true",
+                "registrations_require_3pid: []",
+                "enable_registration_captcha: false",
+                "registration_requires_token: false",
+            ]
+        )
+
+        # Test that allowing open registration without verification raises an error
+        with self.assertRaises(SystemExit):
+            # Do a normal homeserver creation and setup
+            homeserver_config = synapse.app.homeserver.load_or_generate_config(
+                ["-c", self.config_file]
+            )
+            # XXX: The error will be raised at this point
+            hs = synapse.app.homeserver.create_homeserver(homeserver_config)
+            # Continue with the setup. We don't expect this to run because we raised
+            # earlier, but in the future, the code could be refactored to raise the
+            # error in a different place.
+            synapse.app.homeserver.setup(hs)
+
+    def test_load_config_error_if_open_registration_and_no_verification(self) -> None:
+        """
+        Test that `HomeServerConfig.load_config(...)` raises an exception when we detect open
+        registration.
+        """
         self.generate_config()
         self.add_lines_to_config(
             [
@@ -112,7 +147,57 @@ class RegistrationConfigTestCase(ConfigFileTestCase):
 
         # Test that allowing open registration without verification raises an error
         with self.assertRaises(ConfigError):
-            homeserver_config = synapse.app.homeserver.load_or_generate_config(
-                ["-c", self.config_file]
+            _homeserver_config = HomeServerConfig.load_config(
+                description="test", argv_options=["-c", self.config_file]
+            )
+
+    def test_load_or_generate_config_error_if_open_registration_and_no_verification(
+        self,
+    ) -> None:
+        """
+        Test that `HomeServerConfig.load_or_generate_config(...)` raises an exception when we detect open
+        registration.
+        """
+        self.generate_config()
+        self.add_lines_to_config(
+            [
+                " ",
+                "enable_registration: true",
+                "registrations_require_3pid: []",
+                "enable_registration_captcha: false",
+                "registration_requires_token: false",
+            ]
+        )
+
+        # Test that allowing open registration without verification raises an error
+        with self.assertRaises(ConfigError):
+            _homeserver_config = HomeServerConfig.load_or_generate_config(
+                description="test", argv_options=["-c", self.config_file]
+            )
+
+    def test_load_config_with_parser_error_if_open_registration_and_no_verification(
+        self,
+    ) -> None:
+        """
+        Test that `HomeServerConfig.load_config_with_parser(...)` raises an exception when we detect open
+        registration.
+        """
+        self.generate_config()
+        self.add_lines_to_config(
+            [
+                " ",
+                "enable_registration: true",
+                "registrations_require_3pid: []",
+                "enable_registration_captcha: false",
+                "registration_requires_token: false",
+            ]
+        )
+
+        # Test that allowing open registration without verification raises an error
+        with self.assertRaises(ConfigError):
+            config_parser = argparse.ArgumentParser(description="test")
+            HomeServerConfig.add_arguments_to_parser(config_parser)
+
+            _homeserver_config = HomeServerConfig.load_config_with_parser(
+                parser=config_parser, argv_options=["-c", self.config_file]
             )
-            synapse.app.homeserver.setup(homeserver_config)
diff --git a/tests/config/test_workers.py b/tests/config/test_workers.py
index 3a21975b89..55439a502c 100644
--- a/tests/config/test_workers.py
+++ b/tests/config/test_workers.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Any, Mapping, Optional
+from typing import Any, Mapping
 from unittest.mock import Mock
 
 from immutabledict import immutabledict
@@ -35,7 +35,7 @@ class WorkerDutyConfigTestCase(TestCase):
     def _make_worker_config(
         self,
         worker_app: str,
-        worker_name: Optional[str],
+        worker_name: str | None,
         extras: Mapping[str, Any] = _EMPTY_IMMUTABLEDICT,
     ) -> WorkerConfig:
         root_config = Mock()
diff --git a/tests/config/utils.py b/tests/config/utils.py
index 3cba4ac588..efc63558db 100644
--- a/tests/config/utils.py
+++ b/tests/config/utils.py
@@ -24,7 +24,6 @@ import tempfile
 import unittest
 from contextlib import redirect_stdout
 from io import StringIO
-from typing import List
 
 from synapse.config.homeserver import HomeServerConfig
 
@@ -61,7 +60,7 @@ class ConfigFileTestCase(unittest.TestCase):
         with open(self.config_file, "w") as f:
             f.write("".join(contents))
 
-    def add_lines_to_config(self, lines: List[str]) -> None:
+    def add_lines_to_config(self, lines: list[str]) -> None:
         with open(self.config_file, "a") as f:
             for line in lines:
                 f.write(line + "\n")
diff --git a/tests/crypto/test_keyring.py b/tests/crypto/test_keyring.py
index 93ae24628a..d3e8da97f8 100644
--- a/tests/crypto/test_keyring.py
+++ b/tests/crypto/test_keyring.py
@@ -19,7 +19,7 @@
 #
 #
 import time
-from typing import Any, Dict, List, Optional, cast
+from typing import Any, cast
 from unittest.mock import Mock
 
 import attr
@@ -60,7 +60,7 @@ class MockPerspectiveServer:
         self.server_name = "mock_server"
         self.key = signedjson.key.generate_signing_key("0")
 
-    def get_verify_keys(self) -> Dict[str, str]:
+    def get_verify_keys(self) -> dict[str, str]:
         vk = signedjson.key.get_verify_key(self.key)
         return {"%s:%s" % (vk.alg, vk.version): encode_verify_key_base64(vk)}
 
@@ -87,7 +87,7 @@ class FakeRequest:
 @logcontext_clean
 class KeyringTestCase(unittest.HomeserverTestCase):
     def check_context(
-        self, val: ContextRequest, expected: Optional[ContextRequest]
+        self, val: ContextRequest, expected: ContextRequest | None
     ) -> ContextRequest:
         self.assertEqual(getattr(current_context(), "request", None), expected)
         return val
@@ -107,8 +107,8 @@ class KeyringTestCase(unittest.HomeserverTestCase):
         first_lookup_deferred: "Deferred[None]" = Deferred()
 
         async def first_lookup_fetch(
-            server_name: str, key_ids: List[str], minimum_valid_until_ts: int
-        ) -> Dict[str, FetchKeyResult]:
+            server_name: str, key_ids: list[str], minimum_valid_until_ts: int
+        ) -> dict[str, FetchKeyResult]:
             # self.assertEqual(current_context().request.id, "context_11")
             self.assertEqual(server_name, "server10")
             self.assertEqual(key_ids, [get_key_id(key1)])
@@ -152,8 +152,8 @@ class KeyringTestCase(unittest.HomeserverTestCase):
         # should block rather than start a second call
 
         async def second_lookup_fetch(
-            server_name: str, key_ids: List[str], minimum_valid_until_ts: int
-        ) -> Dict[str, FetchKeyResult]:
+            server_name: str, key_ids: list[str], minimum_valid_until_ts: int
+        ) -> dict[str, FetchKeyResult]:
             # self.assertEqual(current_context().request.id, "context_12")
             return {get_key_id(key1): FetchKeyResult(get_verify_key(key1), 100)}
 
@@ -276,8 +276,8 @@ class KeyringTestCase(unittest.HomeserverTestCase):
 
         # set up a mock fetcher which will return the key
         async def get_keys(
-            server_name: str, key_ids: List[str], minimum_valid_until_ts: int
-        ) -> Dict[str, FetchKeyResult]:
+            server_name: str, key_ids: list[str], minimum_valid_until_ts: int
+        ) -> dict[str, FetchKeyResult]:
             self.assertEqual(server_name, self.hs.hostname)
             self.assertEqual(key_ids, [get_key_id(key2)])
 
@@ -302,8 +302,8 @@ class KeyringTestCase(unittest.HomeserverTestCase):
         key1 = signedjson.key.generate_signing_key("1")
 
         async def get_keys(
-            server_name: str, key_ids: List[str], minimum_valid_until_ts: int
-        ) -> Dict[str, FetchKeyResult]:
+            server_name: str, key_ids: list[str], minimum_valid_until_ts: int
+        ) -> dict[str, FetchKeyResult]:
             # there should only be one request object (with the max validity)
             self.assertEqual(server_name, "server1")
             self.assertEqual(key_ids, [get_key_id(key1)])
@@ -344,16 +344,16 @@ class KeyringTestCase(unittest.HomeserverTestCase):
         key1 = signedjson.key.generate_signing_key("1")
 
         async def get_keys1(
-            server_name: str, key_ids: List[str], minimum_valid_until_ts: int
-        ) -> Dict[str, FetchKeyResult]:
+            server_name: str, key_ids: list[str], minimum_valid_until_ts: int
+        ) -> dict[str, FetchKeyResult]:
             self.assertEqual(server_name, "server1")
             self.assertEqual(key_ids, [get_key_id(key1)])
             self.assertEqual(minimum_valid_until_ts, 1500)
             return {get_key_id(key1): FetchKeyResult(get_verify_key(key1), 800)}
 
         async def get_keys2(
-            server_name: str, key_ids: List[str], minimum_valid_until_ts: int
-        ) -> Dict[str, FetchKeyResult]:
+            server_name: str, key_ids: list[str], minimum_valid_until_ts: int
+        ) -> dict[str, FetchKeyResult]:
             self.assertEqual(server_name, "server1")
             self.assertEqual(key_ids, [get_key_id(key1)])
             self.assertEqual(minimum_valid_until_ts, 1500)
@@ -701,7 +701,7 @@ class PerspectivesKeyFetcherTestCase(unittest.HomeserverTestCase):
                 SERVER_NAME, testkey, VALID_UNTIL_TS
             )
 
-        def get_key_from_perspectives(response: JsonDict) -> Dict[str, FetchKeyResult]:
+        def get_key_from_perspectives(response: JsonDict) -> dict[str, FetchKeyResult]:
             fetcher = PerspectivesKeyFetcher(self.hs)
             self.expect_outgoing_key_query(SERVER_NAME, "key1", response)
             return self.get_success(fetcher.get_keys(SERVER_NAME, ["key1"], 0))
diff --git a/tests/events/test_auto_accept_invites.py b/tests/events/test_auto_accept_invites.py
index fa7ea64105..72ade45758 100644
--- a/tests/events/test_auto_accept_invites.py
+++ b/tests/events/test_auto_accept_invites.py
@@ -19,9 +19,8 @@
 #
 #
 import asyncio
-from asyncio import Future
 from http import HTTPStatus
-from typing import Any, Awaitable, Dict, List, Optional, Tuple, TypeVar, cast
+from typing import Any, TypeVar, cast
 from unittest.mock import Mock
 
 import attr
@@ -526,8 +525,8 @@ def generate_request_key() -> SyncRequestKey:
 def sync_join(
     testcase: HomeserverTestCase,
     user_id: str,
-    since_token: Optional[StreamToken] = None,
-) -> Tuple[List[JoinedSyncResult], StreamToken]:
+    since_token: StreamToken | None = None,
+) -> tuple[list[JoinedSyncResult], StreamToken]:
     """Perform a sync request for the given user and return the user join updates
     they've received, as well as the next_batch token.
 
@@ -765,9 +764,9 @@ class MockEvent:
 
     sender: str
     type: str
-    content: Dict[str, Any]
+    content: dict[str, Any]
     room_id: str = "!someroom"
-    state_key: Optional[str] = None
+    state_key: str | None = None
 
     def is_state(self) -> bool:
         """Checks if the event is a state event by checking if it has a state key."""
@@ -787,29 +786,21 @@ TV = TypeVar("TV")
 
 
 async def make_awaitable(value: T) -> T:
+    """
+    Makes a fresh awaitable, suitable for mocking an `async` function.
+    """
     return value
 
 
-def make_multiple_awaitable(result: TV) -> Awaitable[TV]:
-    """
-    Makes an awaitable, suitable for mocking an `async` function.
-    This uses Futures as they can be awaited multiple times so can be returned
-    to multiple callers.
-    """
-    future: Future[TV] = Future()
-    future.set_result(result)
-    return future
-
-
 def create_module(
-    config_override: Optional[Dict[str, Any]] = None, worker_name: Optional[str] = None
+    config_override: dict[str, Any] | None = None, worker_name: str | None = None
 ) -> InviteAutoAccepter:
     # Create a mock based on the ModuleApi spec, but override some mocked functions
     # because some capabilities are needed for running the tests.
     module_api = Mock(spec=ModuleApi)
     module_api.is_mine.side_effect = lambda a: a.split(":")[1] == "test"
     module_api.worker_name = worker_name
-    module_api.sleep.return_value = make_multiple_awaitable(None)
+    module_api.sleep.return_value = lambda *_args, **_kwargs: make_awaitable(None)
     module_api.get_userinfo_by_id.return_value = UserInfo(
         user_id=UserID.from_string("@user:test"),
         is_admin=False,
diff --git a/tests/events/test_presence_router.py b/tests/events/test_presence_router.py
index 696d9dd6e2..4132050647 100644
--- a/tests/events/test_presence_router.py
+++ b/tests/events/test_presence_router.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Dict, Iterable, List, Optional, Set, Tuple, Union
+from typing import Iterable
 from unittest.mock import AsyncMock, Mock
 
 import attr
@@ -46,7 +46,7 @@ from tests.unittest import (
 
 @attr.s
 class PresenceRouterTestConfig:
-    users_who_should_receive_all_presence = attr.ib(type=List[str], default=[])
+    users_who_should_receive_all_presence = attr.ib(type=list[str], default=[])
 
 
 class LegacyPresenceRouterTestModule:
@@ -56,14 +56,14 @@ class LegacyPresenceRouterTestModule:
 
     async def get_users_for_states(
         self, state_updates: Iterable[UserPresenceState]
-    ) -> Dict[str, Set[UserPresenceState]]:
+    ) -> dict[str, set[UserPresenceState]]:
         users_to_state = {
             user_id: set(state_updates)
             for user_id in self._config.users_who_should_receive_all_presence
         }
         return users_to_state
 
-    async def get_interested_users(self, user_id: str) -> Union[Set[str], str]:
+    async def get_interested_users(self, user_id: str) -> set[str] | str:
         if user_id in self._config.users_who_should_receive_all_presence:
             return PresenceRouter.ALL_USERS
 
@@ -106,14 +106,14 @@ class PresenceRouterTestModule:
 
     async def get_users_for_states(
         self, state_updates: Iterable[UserPresenceState]
-    ) -> Dict[str, Set[UserPresenceState]]:
+    ) -> dict[str, set[UserPresenceState]]:
         users_to_state = {
             user_id: set(state_updates)
             for user_id in self._config.users_who_should_receive_all_presence
         }
         return users_to_state
 
-    async def get_interested_users(self, user_id: str) -> Union[Set[str], str]:
+    async def get_interested_users(self, user_id: str) -> set[str] | str:
         if user_id in self._config.users_who_should_receive_all_presence:
             return PresenceRouter.ALL_USERS
 
@@ -482,7 +482,7 @@ def send_presence_update(
     user_id: str,
     access_token: str,
     presence_state: str,
-    status_message: Optional[str] = None,
+    status_message: str | None = None,
 ) -> JsonDict:
     # Build the presence body
     body = {"presence": presence_state}
@@ -510,8 +510,8 @@ def generate_request_key() -> SyncRequestKey:
 def sync_presence(
     testcase: HomeserverTestCase,
     user_id: str,
-    since_token: Optional[StreamToken] = None,
-) -> Tuple[List[UserPresenceState], StreamToken]:
+    since_token: StreamToken | None = None,
+) -> tuple[list[UserPresenceState], StreamToken]:
     """Perform a sync request for the given user and return the user presence updates
     they've received, as well as the next_batch token.
 
diff --git a/tests/events/test_utils.py b/tests/events/test_utils.py
index c6ebefbf38..9ea015e138 100644
--- a/tests/events/test_utils.py
+++ b/tests/events/test_utils.py
@@ -20,7 +20,7 @@
 #
 
 import unittest as stdlib_unittest
-from typing import Any, List, Mapping, Optional
+from typing import Any, Mapping
 
 import attr
 from parameterized import parameterized
@@ -648,7 +648,7 @@ class SerializeEventTestCase(stdlib_unittest.TestCase):
     def serialize(
         self,
         ev: EventBase,
-        fields: Optional[List[str]],
+        fields: list[str] | None,
         include_admin_metadata: bool = False,
     ) -> JsonDict:
         return serialize_event(
diff --git a/tests/federation/test_federation_catch_up.py b/tests/federation/test_federation_catch_up.py
index 5edb651767..fd1ef043bb 100644
--- a/tests/federation/test_federation_catch_up.py
+++ b/tests/federation/test_federation_catch_up.py
@@ -1,4 +1,4 @@
-from typing import Callable, Collection, List, Optional, Tuple
+from typing import Callable, Collection
 from unittest import mock
 from unittest.mock import AsyncMock, Mock
 
@@ -55,8 +55,8 @@ class FederationCatchUpTestCases(FederatingHomeserverTestCase):
         )
 
         # whenever send_transaction is called, record the pdu data
-        self.pdus: List[JsonDict] = []
-        self.failed_pdus: List[JsonDict] = []
+        self.pdus: list[JsonDict] = []
+        self.failed_pdus: list[JsonDict] = []
         self.is_online = True
         self.federation_transport_client.send_transaction.side_effect = (
             self.record_transaction
@@ -72,7 +72,7 @@ class FederationCatchUpTestCases(FederatingHomeserverTestCase):
         return config
 
     async def record_transaction(
-        self, txn: Transaction, json_cb: Optional[Callable[[], JsonDict]]
+        self, txn: Transaction, json_cb: Callable[[], JsonDict] | None
     ) -> JsonDict:
         if json_cb is None:
             # The tests seem to expect that this method raises in this situation.
@@ -269,7 +269,7 @@ class FederationCatchUpTestCases(FederatingHomeserverTestCase):
 
     def make_fake_destination_queue(
         self, destination: str = "host2"
-    ) -> Tuple[PerDestinationQueue, List[EventBase]]:
+    ) -> tuple[PerDestinationQueue, list[EventBase]]:
         """
         Makes a fake per-destination queue.
         """
@@ -279,8 +279,8 @@ class FederationCatchUpTestCases(FederatingHomeserverTestCase):
 
         async def fake_send(
             destination_tm: str,
-            pending_pdus: List[EventBase],
-            _pending_edus: List[Edu],
+            pending_pdus: list[EventBase],
+            _pending_edus: list[Edu],
         ) -> None:
             assert destination == destination_tm
             results_list.extend(pending_pdus)
diff --git a/tests/federation/test_federation_out_of_band_membership.py b/tests/federation/test_federation_out_of_band_membership.py
index fa4e7c63ba..a1ab72b7a1 100644
--- a/tests/federation/test_federation_out_of_band_membership.py
+++ b/tests/federation/test_federation_out_of_band_membership.py
@@ -23,7 +23,7 @@ import logging
 import time
 import urllib.parse
 from http import HTTPStatus
-from typing import Any, Callable, Optional, Set, Tuple, TypeVar, Union
+from typing import Any, Callable, TypeVar
 from unittest.mock import Mock
 
 import attr
@@ -146,8 +146,8 @@ class OutOfBandMembershipTests(unittest.FederatingHomeserverTestCase):
         self.storage_controllers = hs.get_storage_controllers()
 
     def do_sync(
-        self, sync_body: JsonDict, *, since: Optional[str] = None, tok: str
-    ) -> Tuple[JsonDict, str]:
+        self, sync_body: JsonDict, *, since: str | None = None, tok: str
+    ) -> tuple[JsonDict, str]:
         """Do a sliding sync request with given body.
 
         Asserts the request was successful.
@@ -326,13 +326,13 @@ class OutOfBandMembershipTests(unittest.FederatingHomeserverTestCase):
         async def get_json(
             destination: str,
             path: str,
-            args: Optional[QueryParams] = None,
+            args: QueryParams | None = None,
             retry_on_dns_fail: bool = True,
-            timeout: Optional[int] = None,
+            timeout: int | None = None,
             ignore_backoff: bool = False,
             try_trailing_slash_on_400: bool = False,
-            parser: Optional[ByteParser[T]] = None,
-        ) -> Union[JsonDict, T]:
+            parser: ByteParser[T] | None = None,
+        ) -> JsonDict | T:
             if (
                 path
                 == f"/_matrix/federation/v1/make_join/{urllib.parse.quote_plus(remote_room_id)}/{urllib.parse.quote_plus(local_user1_id)}"
@@ -350,22 +350,22 @@ class OutOfBandMembershipTests(unittest.FederatingHomeserverTestCase):
         self.federation_http_client.get_json.side_effect = get_json
 
         # PDU's that hs1 sent to hs2
-        collected_pdus_from_hs1_federation_send: Set[str] = set()
+        collected_pdus_from_hs1_federation_send: set[str] = set()
 
         async def put_json(
             destination: str,
             path: str,
-            args: Optional[QueryParams] = None,
-            data: Optional[JsonDict] = None,
-            json_data_callback: Optional[Callable[[], JsonDict]] = None,
+            args: QueryParams | None = None,
+            data: JsonDict | None = None,
+            json_data_callback: Callable[[], JsonDict] | None = None,
             long_retries: bool = False,
-            timeout: Optional[int] = None,
+            timeout: int | None = None,
             ignore_backoff: bool = False,
             backoff_on_404: bool = False,
             try_trailing_slash_on_400: bool = False,
-            parser: Optional[ByteParser[T]] = None,
+            parser: ByteParser[T] | None = None,
             backoff_on_all_error_codes: bool = False,
-        ) -> Union[JsonDict, T, SendJoinResponse]:
+        ) -> JsonDict | T | SendJoinResponse:
             if (
                 path.startswith(
                     f"/_matrix/federation/v2/send_join/{urllib.parse.quote_plus(remote_room_id)}/"
@@ -503,22 +503,22 @@ class OutOfBandMembershipTests(unittest.FederatingHomeserverTestCase):
         T = TypeVar("T")
 
         # PDU's that hs1 sent to hs2
-        collected_pdus_from_hs1_federation_send: Set[str] = set()
+        collected_pdus_from_hs1_federation_send: set[str] = set()
 
         async def put_json(
             destination: str,
             path: str,
-            args: Optional[QueryParams] = None,
-            data: Optional[JsonDict] = None,
-            json_data_callback: Optional[Callable[[], JsonDict]] = None,
+            args: QueryParams | None = None,
+            data: JsonDict | None = None,
+            json_data_callback: Callable[[], JsonDict] | None = None,
             long_retries: bool = False,
-            timeout: Optional[int] = None,
+            timeout: int | None = None,
             ignore_backoff: bool = False,
             backoff_on_404: bool = False,
             try_trailing_slash_on_400: bool = False,
-            parser: Optional[ByteParser[T]] = None,
+            parser: ByteParser[T] | None = None,
             backoff_on_all_error_codes: bool = False,
-        ) -> Union[JsonDict, T]:
+        ) -> JsonDict | T:
             if path.startswith("/_matrix/federation/v1/send/") and data is not None:
                 for pdu in data.get("pdus", []):
                     event = event_from_pdu_json(pdu, room_version)
diff --git a/tests/federation/test_federation_sender.py b/tests/federation/test_federation_sender.py
index 27b69a9180..ced98a8b00 100644
--- a/tests/federation/test_federation_sender.py
+++ b/tests/federation/test_federation_sender.py
@@ -17,7 +17,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Callable, FrozenSet, List, Optional, Set
+from typing import Callable
 from unittest.mock import AsyncMock, Mock
 
 from signedjson import key, sign
@@ -435,7 +435,7 @@ class FederationSenderPresenceTestCases(HomeserverTestCase):
 
         # A set of all user presence we see, this should end up matching the
         # number we sent out above.
-        seen_users: Set[str] = set()
+        seen_users: set[str] = set()
 
         for edu in presence_edus:
             presence_states = edu["content"]["push"]
@@ -483,12 +483,12 @@ class FederationSenderDevicesTestCases(HomeserverTestCase):
 
         # stub out `get_rooms_for_user` and `get_current_hosts_in_room` so that the
         # server thinks the user shares a room with `@user2:host2`
-        def get_rooms_for_user(user_id: str) -> "defer.Deferred[FrozenSet[str]]":
+        def get_rooms_for_user(user_id: str) -> "defer.Deferred[frozenset[str]]":
             return defer.succeed(frozenset({test_room_id}))
 
         hs.get_datastores().main.get_rooms_for_user = get_rooms_for_user  # type: ignore[assignment]
 
-        async def get_current_hosts_in_room(room_id: str) -> Set[str]:
+        async def get_current_hosts_in_room(room_id: str) -> set[str]:
             if room_id == test_room_id:
                 return {"host2"}
             else:
@@ -504,13 +504,13 @@ class FederationSenderDevicesTestCases(HomeserverTestCase):
         self.device_handler = device_handler
 
         # whenever send_transaction is called, record the edu data
-        self.edus: List[JsonDict] = []
+        self.edus: list[JsonDict] = []
         self.federation_transport_client.send_transaction.side_effect = (
             self.record_transaction
         )
 
     async def record_transaction(
-        self, txn: Transaction, json_cb: Optional[Callable[[], JsonDict]] = None
+        self, txn: Transaction, json_cb: Callable[[], JsonDict] | None = None
     ) -> JsonDict:
         assert json_cb is not None
         data = json_cb()
@@ -592,7 +592,7 @@ class FederationSenderDevicesTestCases(HomeserverTestCase):
 
         # expect two edus
         self.assertEqual(len(self.edus), 2)
-        stream_id: Optional[int] = None
+        stream_id: int | None = None
         stream_id = self.check_device_update_edu(self.edus.pop(0), u1, "D1", stream_id)
         stream_id = self.check_device_update_edu(self.edus.pop(0), u1, "D2", stream_id)
 
@@ -754,7 +754,7 @@ class FederationSenderDevicesTestCases(HomeserverTestCase):
 
         # for each device, there should be a single update
         self.assertEqual(len(self.edus), 3)
-        stream_id: Optional[int] = None
+        stream_id: int | None = None
         for edu in self.edus:
             self.assertEqual(edu["edu_type"], EduTypes.DEVICE_LIST_UPDATE)
             c = edu["content"]
@@ -876,7 +876,7 @@ class FederationSenderDevicesTestCases(HomeserverTestCase):
         edu: JsonDict,
         user_id: str,
         device_id: str,
-        prev_stream_id: Optional[int],
+        prev_stream_id: int | None,
     ) -> int:
         """Check that the given EDU is an update for the given device
         Returns the stream_id.
diff --git a/tests/federation/test_federation_server.py b/tests/federation/test_federation_server.py
index 509f1f1e82..0d74791290 100644
--- a/tests/federation/test_federation_server.py
+++ b/tests/federation/test_federation_server.py
@@ -20,7 +20,6 @@
 #
 import logging
 from http import HTTPStatus
-from typing import Optional, Union
 from unittest.mock import Mock
 
 from parameterized import parameterized
@@ -192,12 +191,12 @@ class MessageAcceptTests(unittest.FederatingHomeserverTestCase):
         async def post_json(
             destination: str,
             path: str,
-            data: Optional[JsonDict] = None,
+            data: JsonDict | None = None,
             long_retries: bool = False,
-            timeout: Optional[int] = None,
+            timeout: int | None = None,
             ignore_backoff: bool = False,
-            args: Optional[QueryParams] = None,
-        ) -> Union[JsonDict, list]:
+            args: QueryParams | None = None,
+        ) -> JsonDict | list:
             # If it asks us for new missing events, give them NOTHING
             if path.startswith("/_matrix/federation/v1/get_missing_events/"):
                 return {"events": []}
@@ -462,7 +461,7 @@ class SendJoinFederationTests(unittest.FederatingHomeserverTestCase):
         )
         self.assertEqual(r[("m.room.member", joining_user)].membership, "join")
 
-    @override_config({"rc_joins_per_room": {"per_second": 0, "burst_count": 3}})
+    @override_config({"rc_joins_per_room": {"per_second": 0.1, "burst_count": 3}})
     def test_make_join_respects_room_join_rate_limit(self) -> None:
         # In the test setup, two users join the room. Since the rate limiter burst
         # count is 3, a new make_join request to the room should be accepted.
@@ -484,7 +483,7 @@ class SendJoinFederationTests(unittest.FederatingHomeserverTestCase):
         )
         self.assertEqual(channel.code, HTTPStatus.TOO_MANY_REQUESTS, channel.json_body)
 
-    @override_config({"rc_joins_per_room": {"per_second": 0, "burst_count": 3}})
+    @override_config({"rc_joins_per_room": {"per_second": 0.1, "burst_count": 3}})
     def test_send_join_contributes_to_room_join_rate_limit_and_is_limited(self) -> None:
         # Make two make_join requests up front. (These are rate limited, but do not
         # contribute to the rate limit.)
diff --git a/tests/federation/transport/server/test__base.py b/tests/federation/transport/server/test__base.py
index 0e3b41ec4d..3c553e6e40 100644
--- a/tests/federation/transport/server/test__base.py
+++ b/tests/federation/transport/server/test__base.py
@@ -20,7 +20,6 @@
 #
 
 from http import HTTPStatus
-from typing import Dict, List, Tuple
 
 from twisted.web.resource import Resource
 
@@ -52,14 +51,14 @@ class CancellableFederationServlet(BaseFederationServlet):
 
     @cancellable
     async def on_GET(
-        self, origin: str, content: None, query: Dict[bytes, List[bytes]]
-    ) -> Tuple[int, JsonDict]:
+        self, origin: str, content: None, query: dict[bytes, list[bytes]]
+    ) -> tuple[int, JsonDict]:
         await self.clock.sleep(1.0)
         return HTTPStatus.OK, {"result": True}
 
     async def on_POST(
-        self, origin: str, content: JsonDict, query: Dict[bytes, List[bytes]]
-    ) -> Tuple[int, JsonDict]:
+        self, origin: str, content: JsonDict, query: dict[bytes, list[bytes]]
+    ) -> tuple[int, JsonDict]:
         await self.clock.sleep(1.0)
         return HTTPStatus.OK, {"result": True}
 
diff --git a/tests/federation/transport/test_client.py b/tests/federation/transport/test_client.py
index 3d882f99f2..9a6bbabd35 100644
--- a/tests/federation/transport/test_client.py
+++ b/tests/federation/transport/test_client.py
@@ -20,7 +20,6 @@
 #
 
 import json
-from typing import List, Optional
 from unittest.mock import Mock
 
 import ijson.common
@@ -98,7 +97,7 @@ class SendJoinParserTestCase(TestCase):
     def test_servers_in_room(self) -> None:
         """Check that the servers_in_room field is correctly parsed"""
 
-        def parse(response: JsonDict) -> Optional[List[str]]:
+        def parse(response: JsonDict) -> list[str] | None:
             parser = SendJoinParser(RoomVersions.V1, False)
             serialised_response = json.dumps(response).encode()
 
diff --git a/tests/federation/transport/test_knocking.py b/tests/federation/transport/test_knocking.py
index a243938255..ec705676cc 100644
--- a/tests/federation/transport/test_knocking.py
+++ b/tests/federation/transport/test_knocking.py
@@ -19,7 +19,7 @@
 #
 #
 from collections import OrderedDict
-from typing import Any, Dict, List, Optional
+from typing import Any
 
 from twisted.internet.testing import MemoryReactor
 
@@ -161,8 +161,8 @@ class KnockingStrippedStateEventHelperMixin(HomeserverTestCase):
 
     def check_knock_room_state_against_room_state(
         self,
-        knock_room_state: List[Dict],
-        expected_room_state: Dict,
+        knock_room_state: list[dict],
+        expected_room_state: dict,
     ) -> None:
         """Test a list of stripped room state events received over federation against a
         dict of expected state events.
@@ -232,7 +232,7 @@ class FederationKnockingTestCase(
         # Have this homeserver skip event auth checks. This is necessary due to
         # event auth checks ensuring that events were signed by the sender's homeserver.
         async def _check_event_auth(
-            origin: Optional[str], event: EventBase, context: EventContext
+            origin: str | None, event: EventBase, context: EventContext
         ) -> None:
             pass
 
diff --git a/tests/handlers/test_appservice.py b/tests/handlers/test_appservice.py
index 999d7f5e6c..6336edb108 100644
--- a/tests/handlers/test_appservice.py
+++ b/tests/handlers/test_appservice.py
@@ -19,7 +19,14 @@
 #
 #
 
-from typing import Dict, Iterable, List, Optional
+from typing import (
+    TYPE_CHECKING,
+    Any,
+    Awaitable,
+    Callable,
+    Iterable,
+    TypeVar,
+)
 from unittest.mock import AsyncMock, Mock
 
 from parameterized import parameterized
@@ -36,6 +43,7 @@ from synapse.appservice import (
     TransactionUnusedFallbackKeys,
 )
 from synapse.handlers.appservice import ApplicationServicesHandler
+from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.rest.client import login, receipts, register, room, sendtodevice
 from synapse.server import HomeServer
 from synapse.types import (
@@ -49,9 +57,14 @@ from synapse.util.clock import Clock
 from synapse.util.stringutils import random_string
 
 from tests import unittest
+from tests.server import get_clock
 from tests.test_utils import event_injection
 from tests.unittest import override_config
-from tests.utils import MockClock
+
+if TYPE_CHECKING:
+    from typing_extensions import LiteralString
+
+R = TypeVar("R")
 
 
 class AppServiceHandlerTestCase(unittest.TestCase):
@@ -61,14 +74,27 @@ class AppServiceHandlerTestCase(unittest.TestCase):
         self.mock_store = Mock()
         self.mock_as_api = AsyncMock()
         self.mock_scheduler = Mock()
+        self.reactor, self.clock = get_clock()
+
         hs = Mock()
+
+        def test_run_as_background_process(
+            desc: "LiteralString",
+            func: Callable[..., Awaitable[R | None]],
+            *args: Any,
+            **kwargs: Any,
+        ) -> "defer.Deferred[R | None]":
+            # Ignore linter error as this is used only for testing purposes (i.e. outside of Synapse).
+            return run_as_background_process(desc, "test_server", func, *args, **kwargs)  # type: ignore[untracked-background-process]
+
+        hs.run_as_background_process = test_run_as_background_process
         hs.get_datastores.return_value = Mock(main=self.mock_store)
         self.mock_store.get_appservice_last_pos = AsyncMock(return_value=None)
         self.mock_store.set_appservice_last_pos = AsyncMock(return_value=None)
         self.mock_store.set_appservice_stream_type_pos = AsyncMock(return_value=None)
         hs.get_application_service_api.return_value = self.mock_as_api
         hs.get_application_service_scheduler.return_value = self.mock_scheduler
-        hs.get_clock.return_value = MockClock()
+        hs.get_clock.return_value = self.clock
         self.handler = ApplicationServicesHandler(hs)
         self.event_source = hs.get_event_sources()
 
@@ -266,7 +292,7 @@ class AppServiceHandlerTestCase(unittest.TestCase):
 
         async def get_3pe_protocol(
             service: ApplicationService, protocol: str
-        ) -> Optional[JsonDict]:
+        ) -> JsonDict | None:
             if service == service_one:
                 return {
                     "x-protocol-data": 42,
@@ -358,7 +384,7 @@ class AppServiceHandlerTestCase(unittest.TestCase):
         )
 
     def _mkservice(
-        self, is_interested_in_event: bool, protocols: Optional[Iterable] = None
+        self, is_interested_in_event: bool, protocols: Iterable | None = None
     ) -> Mock:
         """
         Create a new mock representing an ApplicationService.
@@ -421,7 +447,7 @@ class ApplicationServicesHandlerSendEventsTestCase(unittest.HomeserverTestCase):
         hs.get_application_service_handler().scheduler.txn_ctrl.send = self.send_mock  # type: ignore[method-assign]
 
         # Mock out application services, and allow defining our own in tests
-        self._services: List[ApplicationService] = []
+        self._services: list[ApplicationService] = []
         self.hs.get_datastores().main.get_app_services = Mock(  # type: ignore[method-assign]
             return_value=self._services
         )
@@ -855,7 +881,7 @@ class ApplicationServicesHandlerSendEventsTestCase(unittest.HomeserverTestCase):
         # Count the total number of to-device messages that were sent out per-service.
         # Ensure that we only sent to-device messages to interested services, and that
         # each interested service received the full count of to-device messages.
-        service_id_to_message_count: Dict[str, int] = {}
+        service_id_to_message_count: dict[str, int] = {}
 
         for call in self.send_mock.call_args_list:
             (
@@ -994,7 +1020,7 @@ class ApplicationServicesHandlerSendEventsTestCase(unittest.HomeserverTestCase):
 
     def _register_application_service(
         self,
-        namespaces: Optional[Dict[str, Iterable[Dict]]] = None,
+        namespaces: dict[str, Iterable[dict]] | None = None,
     ) -> ApplicationService:
         """
         Register a new application service, with the given namespaces of interest.
@@ -1044,7 +1070,7 @@ class ApplicationServicesHandlerDeviceListsTestCase(unittest.HomeserverTestCase)
         hs.get_application_service_api().put_json = self.put_json  # type: ignore[method-assign]
 
         # Mock out application services, and allow defining our own in tests
-        self._services: List[ApplicationService] = []
+        self._services: list[ApplicationService] = []
         self.hs.get_datastores().main.get_app_services = Mock(  # type: ignore[method-assign]
             return_value=self._services
         )
@@ -1289,8 +1315,8 @@ class ApplicationServicesHandlerOtkCountsTestCase(unittest.HomeserverTestCase):
         # Capture what was sent as an AS transaction.
         self.send_mock.assert_called()
         last_args, _last_kwargs = self.send_mock.call_args
-        otks: Optional[TransactionOneTimeKeysCount] = last_args[self.ARG_OTK_COUNTS]
-        unused_fallbacks: Optional[TransactionUnusedFallbackKeys] = last_args[
+        otks: TransactionOneTimeKeysCount | None = last_args[self.ARG_OTK_COUNTS]
+        unused_fallbacks: TransactionUnusedFallbackKeys | None = last_args[
             self.ARG_FALLBACK_KEYS
         ]
 
diff --git a/tests/handlers/test_auth.py b/tests/handlers/test_auth.py
index acefd707f5..648be7e7e7 100644
--- a/tests/handlers/test_auth.py
+++ b/tests/handlers/test_auth.py
@@ -18,7 +18,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Optional
 from unittest.mock import AsyncMock
 
 import pymacaroons
@@ -55,7 +54,7 @@ class AuthTestCase(unittest.HomeserverTestCase):
 
         self.user1 = self.register_user("a_user", "pass")
 
-    def token_login(self, token: str) -> Optional[str]:
+    def token_login(self, token: str) -> str | None:
         body = {
             "type": "m.login.token",
             "token": token,
diff --git a/tests/handlers/test_cas.py b/tests/handlers/test_cas.py
index f677f3be2a..02671fc264 100644
--- a/tests/handlers/test_cas.py
+++ b/tests/handlers/test_cas.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Any, Dict
+from typing import Any
 from unittest.mock import AsyncMock, Mock
 
 from twisted.internet.testing import MemoryReactor
@@ -35,7 +35,7 @@ SERVER_URL = "https://issuer/"
 
 
 class CasHandlerTestCase(HomeserverTestCase):
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         config = super().default_config()
         config["public_baseurl"] = BASE_URL
         cas_config = {
diff --git a/tests/handlers/test_device.py b/tests/handlers/test_device.py
index 5b04da8640..acd37a1c71 100644
--- a/tests/handlers/test_device.py
+++ b/tests/handlers/test_device.py
@@ -20,7 +20,6 @@
 #
 #
 
-from typing import Optional
 from unittest import mock
 
 from twisted.internet.defer import ensureDeferred
@@ -312,8 +311,8 @@ class DeviceTestCase(unittest.HomeserverTestCase):
         user_id: str,
         device_id: str,
         display_name: str,
-        access_token: Optional[str] = None,
-        ip: Optional[str] = None,
+        access_token: str | None = None,
+        ip: str | None = None,
     ) -> None:
         device_id = self.get_success(
             self.handler.check_device_registered(
diff --git a/tests/handlers/test_directory.py b/tests/handlers/test_directory.py
index 45b8f2353a..76b145b92b 100644
--- a/tests/handlers/test_directory.py
+++ b/tests/handlers/test_directory.py
@@ -19,7 +19,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Any, Awaitable, Callable, Dict
+from typing import Any, Awaitable, Callable
 from unittest.mock import AsyncMock, Mock
 
 from twisted.internet.testing import MemoryReactor
@@ -43,7 +43,7 @@ class DirectoryTestCase(unittest.HomeserverTestCase):
         self.mock_federation = AsyncMock()
         self.mock_registry = Mock()
 
-        self.query_handlers: Dict[str, Callable[[dict], Awaitable[JsonDict]]] = {}
+        self.query_handlers: dict[str, Callable[[dict], Awaitable[JsonDict]]] = {}
 
         def register_query_handler(
             query_type: str, handler: Callable[[dict], Awaitable[JsonDict]]
@@ -410,7 +410,7 @@ class TestCreateAliasACL(unittest.HomeserverTestCase):
 
     servlets = [directory.register_servlets, room.register_servlets]
 
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         config = super().default_config()
 
         # Add custom alias creation rules to the config.
@@ -476,7 +476,7 @@ class TestCreatePublishedRoomACL(unittest.HomeserverTestCase):
     data = {"room_alias_name": "unofficial_test"}
     allowed_localpart = "allowed"
 
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         config = super().default_config()
 
         # Add custom room list publication rules to the config.
diff --git a/tests/handlers/test_e2e_keys.py b/tests/handlers/test_e2e_keys.py
index 4f0b1574b3..a4f9d55a13 100644
--- a/tests/handlers/test_e2e_keys.py
+++ b/tests/handlers/test_e2e_keys.py
@@ -20,7 +20,7 @@
 #
 #
 import time
-from typing import Dict, Iterable
+from typing import Iterable
 from unittest import mock
 
 from parameterized import parameterized
@@ -291,7 +291,7 @@ class E2eKeysHandlerTestCase(unittest.HomeserverTestCase):
             (chris, "chris_dev_2", "alg2"): 1,
         }
         # Convert to the format the handler wants.
-        query: Dict[str, Dict[str, Dict[str, int]]] = {}
+        query: dict[str, dict[str, dict[str, int]]] = {}
         for (user_id, device_id, algorithm), count in claims_to_make.items():
             query.setdefault(user_id, {}).setdefault(device_id, {})[algorithm] = count
         claim_res = self.get_success(
@@ -410,7 +410,6 @@ class E2eKeysHandlerTestCase(unittest.HomeserverTestCase):
         device_id = "xyz"
         fallback_key = {"alg1:k1": "fallback_key1"}
         fallback_key2 = {"alg1:k2": "fallback_key2"}
-        fallback_key3 = {"alg1:k2": "fallback_key3"}
         otk = {"alg1:k2": "key2"}
 
         # we shouldn't have any unused fallback keys yet
@@ -531,28 +530,6 @@ class E2eKeysHandlerTestCase(unittest.HomeserverTestCase):
             {"failures": {}, "one_time_keys": {local_user: {device_id: fallback_key2}}},
         )
 
-        # using the unstable prefix should also set the fallback key
-        self.get_success(
-            self.handler.upload_keys_for_user(
-                local_user,
-                device_id,
-                {"org.matrix.msc2732.fallback_keys": fallback_key3},
-            )
-        )
-
-        claim_res = self.get_success(
-            self.handler.claim_one_time_keys(
-                {local_user: {device_id: {"alg1": 1}}},
-                self.requester,
-                timeout=None,
-                always_include_fallback_keys=False,
-            )
-        )
-        self.assertEqual(
-            claim_res,
-            {"failures": {}, "one_time_keys": {local_user: {device_id: fallback_key3}}},
-        )
-
     def test_fallback_key_bulk(self) -> None:
         """Like test_fallback_key, but claims multiple keys in one handler call."""
         alice = f"@alice:{self.hs.hostname}"
@@ -1533,7 +1510,7 @@ class E2eKeysHandlerTestCase(unittest.HomeserverTestCase):
         )
 
         # Setup a response.
-        response: Dict[str, Dict[str, Dict[str, JsonDict]]] = {
+        response: dict[str, dict[str, dict[str, JsonDict]]] = {
             local_user: {device_id_1: {**as_otk, **as_fallback_key}}
         }
         self.appservice_api.claim_client_keys.return_value = (response, [])
diff --git a/tests/handlers/test_e2e_room_keys.py b/tests/handlers/test_e2e_room_keys.py
index 910c24c167..5085a0309b 100644
--- a/tests/handlers/test_e2e_room_keys.py
+++ b/tests/handlers/test_e2e_room_keys.py
@@ -21,7 +21,6 @@
 #
 
 import copy
-from unittest import mock
 
 from twisted.internet.testing import MemoryReactor
 
@@ -50,7 +49,7 @@ room_keys = {
 
 class E2eRoomKeysHandlerTestCase(unittest.HomeserverTestCase):
     def make_homeserver(self, reactor: MemoryReactor, clock: Clock) -> HomeServer:
-        return self.setup_test_homeserver(replication_layer=mock.Mock())
+        return self.setup_test_homeserver()
 
     def prepare(self, reactor: MemoryReactor, clock: Clock, hs: HomeServer) -> None:
         self.handler = hs.get_e2e_room_keys_handler()
diff --git a/tests/handlers/test_federation.py b/tests/handlers/test_federation.py
index c9ece68729..7085531548 100644
--- a/tests/handlers/test_federation.py
+++ b/tests/handlers/test_federation.py
@@ -19,7 +19,7 @@
 #
 #
 import logging
-from typing import Collection, Optional, cast
+from typing import Collection, cast
 from unittest import TestCase
 from unittest.mock import AsyncMock, Mock, patch
 
@@ -689,7 +689,7 @@ class PartialJoinTestCase(unittest.FederatingHomeserverTestCase):
             return is_partial_state
 
         async def sync_partial_state_room(
-            initial_destination: Optional[str],
+            initial_destination: str | None,
             other_destinations: Collection[str],
             room_id: str,
         ) -> None:
@@ -744,7 +744,7 @@ class PartialJoinTestCase(unittest.FederatingHomeserverTestCase):
             return is_partial_state
 
         async def sync_partial_state_room(
-            initial_destination: Optional[str],
+            initial_destination: str | None,
             other_destinations: Collection[str],
             room_id: str,
         ) -> None:
diff --git a/tests/handlers/test_federation_event.py b/tests/handlers/test_federation_event.py
index 5771699a62..3d856b9346 100644
--- a/tests/handlers/test_federation_event.py
+++ b/tests/handlers/test_federation_event.py
@@ -18,7 +18,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Optional
 from unittest import mock
 
 from twisted.internet.testing import MemoryReactor
@@ -183,7 +182,7 @@ class FederationEventHandlerTests(unittest.FederatingHomeserverTestCase):
         else:
 
             async def get_event(
-                destination: str, event_id: str, timeout: Optional[int] = None
+                destination: str, event_id: str, timeout: int | None = None
             ) -> JsonDict:
                 self.assertEqual(destination, self.OTHER_SERVER_NAME)
                 self.assertEqual(event_id, prev_event.event_id)
@@ -585,7 +584,7 @@ class FederationEventHandlerTests(unittest.FederatingHomeserverTestCase):
         room_state_endpoint_requested_count = 0
 
         async def get_event(
-            destination: str, event_id: str, timeout: Optional[int] = None
+            destination: str, event_id: str, timeout: int | None = None
         ) -> None:
             nonlocal event_endpoint_requested_count
             event_endpoint_requested_count += 1
@@ -1115,7 +1114,7 @@ class FederationEventHandlerTests(unittest.FederatingHomeserverTestCase):
         ):
 
             async def get_event(
-                destination: str, event_id: str, timeout: Optional[int] = None
+                destination: str, event_id: str, timeout: int | None = None
             ) -> JsonDict:
                 self.assertEqual(destination, self.OTHER_SERVER_NAME)
                 self.assertEqual(event_id, missing_event.event_id)
diff --git a/tests/handlers/test_message.py b/tests/handlers/test_message.py
index 4262e805e7..6450a90444 100644
--- a/tests/handlers/test_message.py
+++ b/tests/handlers/test_message.py
@@ -19,7 +19,6 @@
 #
 #
 import logging
-from typing import Tuple
 
 from twisted.internet.testing import MemoryReactor
 
@@ -64,7 +63,7 @@ class EventCreationTestCase(unittest.HomeserverTestCase):
 
         self.requester = create_requester(self.user_id, device_id=device_id)
 
-    def _create_and_persist_member_event(self) -> Tuple[EventBase, EventContext]:
+    def _create_and_persist_member_event(self) -> tuple[EventBase, EventContext]:
         # Create a member event we can use as an auth_event
         memberEvent, memberEventContext = self.get_success(
             create_event(
@@ -86,7 +85,7 @@ class EventCreationTestCase(unittest.HomeserverTestCase):
 
     def _create_duplicate_event(
         self, txn_id: str
-    ) -> Tuple[EventBase, UnpersistedEventContextBase]:
+    ) -> tuple[EventBase, UnpersistedEventContextBase]:
         """Create a new event with the given transaction ID. All events produced
         by this method will be considered duplicates.
         """
diff --git a/tests/handlers/test_oauth_delegation.py b/tests/handlers/test_oauth_delegation.py
index 4640f35a1e..c0a197874e 100644
--- a/tests/handlers/test_oauth_delegation.py
+++ b/tests/handlers/test_oauth_delegation.py
@@ -25,7 +25,7 @@ import time
 from http import HTTPStatus
 from http.server import BaseHTTPRequestHandler, HTTPServer
 from io import BytesIO
-from typing import Any, ClassVar, Coroutine, Dict, Generator, Optional, TypeVar, Union
+from typing import Any, ClassVar, Coroutine, Generator, TypeVar, Union
 from unittest.mock import ANY, AsyncMock, Mock
 from urllib.parse import parse_qs
 
@@ -130,7 +130,7 @@ class MSC3861OAuthDelegation(HomeserverTestCase):
         keys.register_servlets,
     ]
 
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         config = super().default_config()
         config["public_baseurl"] = BASE_URL
         config["disable_registration"] = True
@@ -759,7 +759,7 @@ class FakeMasServer(HTTPServer):
     secret: str = "verysecret"
     """The shared secret used to authenticate the introspection endpoint."""
 
-    last_token_seen: Optional[str] = None
+    last_token_seen: str | None = None
     """What is the last access token seen by the introspection endpoint."""
 
     calls: int = 0
@@ -834,7 +834,7 @@ class MasAuthDelegation(HomeserverTestCase):
 
         return deferred
 
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         config = super().default_config()
         config["public_baseurl"] = BASE_URL
         config["disable_registration"] = True
@@ -1100,9 +1100,9 @@ class DisabledEndpointsTestCase(HomeserverTestCase):
         admin.register_servlets,
     ]
 
-    config: Dict[str, Any]
+    config: dict[str, Any]
 
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         config = super().default_config()
         config["public_baseurl"] = BASE_URL
         config["disable_registration"] = True
@@ -1110,7 +1110,7 @@ class DisabledEndpointsTestCase(HomeserverTestCase):
         return config
 
     def expect_unauthorized(
-        self, method: str, path: str, content: Union[bytes, str, JsonDict] = ""
+        self, method: str, path: str, content: bytes | str | JsonDict = ""
     ) -> None:
         channel = self.make_request(method, path, content, shorthand=False)
 
@@ -1120,7 +1120,7 @@ class DisabledEndpointsTestCase(HomeserverTestCase):
         self,
         method: str,
         path: str,
-        content: Union[bytes, str, JsonDict] = "",
+        content: bytes | str | JsonDict = "",
         auth: bool = False,
     ) -> None:
         channel = self.make_request(
@@ -1133,7 +1133,7 @@ class DisabledEndpointsTestCase(HomeserverTestCase):
         )
 
     def expect_forbidden(
-        self, method: str, path: str, content: Union[bytes, str, JsonDict] = ""
+        self, method: str, path: str, content: bytes | str | JsonDict = ""
     ) -> None:
         channel = self.make_request(method, path, content)
 
diff --git a/tests/handlers/test_oidc.py b/tests/handlers/test_oidc.py
index 5207382f00..4583afb625 100644
--- a/tests/handlers/test_oidc.py
+++ b/tests/handlers/test_oidc.py
@@ -19,7 +19,7 @@
 #
 #
 import os
-from typing import Any, Awaitable, ContextManager, Dict, Optional, Tuple
+from typing import Any, Awaitable, ContextManager
 from unittest.mock import ANY, AsyncMock, Mock, patch
 from urllib.parse import parse_qs, urlparse
 
@@ -152,7 +152,7 @@ class OidcHandlerTestCase(HomeserverTestCase):
     if not HAS_OIDC:
         skip = "requires OIDC"
 
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         config = super().default_config()
         config["public_baseurl"] = BASE_URL
         return config
@@ -204,7 +204,7 @@ class OidcHandlerTestCase(HomeserverTestCase):
         client_redirect_url: str = "http://client/redirect",
         scope: str = "openid",
         with_sid: bool = False,
-    ) -> Tuple[SynapseRequest, FakeAuthorizationGrant]:
+    ) -> tuple[SynapseRequest, FakeAuthorizationGrant]:
         """Start an authorization request, and get the callback request back."""
         nonce = random_string(10)
         state = random_string(10)
@@ -221,8 +221,8 @@ class OidcHandlerTestCase(HomeserverTestCase):
         return _build_callback_request(code, state, session), grant
 
     def assertRenderedError(
-        self, error: str, error_description: Optional[str] = None
-    ) -> Tuple[Any, ...]:
+        self, error: str, error_description: str | None = None
+    ) -> tuple[Any, ...]:
         self.render_error.assert_called_once()
         args = self.render_error.call_args[0]
         self.assertEqual(args[1], error)
diff --git a/tests/handlers/test_password_providers.py b/tests/handlers/test_password_providers.py
index aa41875063..573ba58c4f 100644
--- a/tests/handlers/test_password_providers.py
+++ b/tests/handlers/test_password_providers.py
@@ -22,7 +22,7 @@
 """Tests for the password_auth_provider interface"""
 
 from http import HTTPStatus
-from typing import Any, Dict, List, Optional, Type, Union
+from typing import Any
 from unittest.mock import AsyncMock, Mock
 
 from twisted.internet.testing import MemoryReactor
@@ -75,7 +75,7 @@ class LegacyCustomAuthProvider:
     def __init__(self, config: None, account_handler: AccountHandler):
         pass
 
-    def get_supported_login_types(self) -> Dict[str, List[str]]:
+    def get_supported_login_types(self) -> dict[str, list[str]]:
         return {"test.login_type": ["test_field"]}
 
     def check_auth(self, *args: str) -> Mock:
@@ -109,7 +109,7 @@ class LegacyPasswordCustomAuthProvider:
     def __init__(self, config: None, account_handler: AccountHandler):
         pass
 
-    def get_supported_login_types(self) -> Dict[str, List[str]]:
+    def get_supported_login_types(self) -> dict[str, list[str]]:
         return {"m.login.password": ["password"], "test.login_type": ["test_field"]}
 
     def check_auth(self, *args: str) -> Mock:
@@ -139,7 +139,7 @@ class PasswordCustomAuthProvider:
         return mock_password_provider.check_password(*args)
 
 
-def legacy_providers_config(*providers: Type[Any]) -> dict:
+def legacy_providers_config(*providers: type[Any]) -> dict:
     """Returns a config dict that will enable the given legacy password auth providers"""
     return {
         "password_providers": [
@@ -149,7 +149,7 @@ def legacy_providers_config(*providers: Type[Any]) -> dict:
     }
 
 
-def providers_config(*providers: Type[Any]) -> dict:
+def providers_config(*providers: type[Any]) -> dict:
     """Returns a config dict that will enable the given modules"""
     return {
         "modules": [
@@ -707,7 +707,7 @@ class PasswordAuthProviderTests(unittest.HomeserverTestCase):
         self.called = False
 
         async def on_logged_out(
-            user_id: str, device_id: Optional[str], access_token: str
+            user_id: str, device_id: str | None, access_token: str
         ) -> None:
             self.called = True
 
@@ -978,7 +978,7 @@ class PasswordAuthProviderTests(unittest.HomeserverTestCase):
         self,
         access_token: str,
         device: str,
-        body: Union[JsonDict, bytes] = b"",
+        body: JsonDict | bytes = b"",
     ) -> FakeChannel:
         """Delete an individual device."""
         channel = self.make_request(
diff --git a/tests/handlers/test_presence.py b/tests/handlers/test_presence.py
index de1bc90c67..44f1e6432d 100644
--- a/tests/handlers/test_presence.py
+++ b/tests/handlers/test_presence.py
@@ -19,7 +19,7 @@
 #
 #
 import itertools
-from typing import Optional, cast
+from typing import cast
 from unittest.mock import Mock, call
 
 from parameterized import parameterized
@@ -1650,7 +1650,7 @@ class PresenceHandlerTestCase(BaseMultiWorkerStreamTestCase):
         self.assertEqual(state.state, PresenceState.ONLINE)
 
     def _set_presencestate_with_status_msg(
-        self, state: str, status_msg: Optional[str]
+        self, state: str, status_msg: str | None
     ) -> None:
         """Set a PresenceState and status_msg and check the result.
 
diff --git a/tests/handlers/test_profile.py b/tests/handlers/test_profile.py
index 73426c7b04..7a7f803ebd 100644
--- a/tests/handlers/test_profile.py
+++ b/tests/handlers/test_profile.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Any, Awaitable, Callable, Dict
+from typing import Any, Awaitable, Callable
 from unittest.mock import AsyncMock, Mock
 
 from parameterized import parameterized
@@ -44,7 +44,7 @@ class ProfileTestCase(unittest.HomeserverTestCase):
         self.mock_federation = AsyncMock()
         self.mock_registry = Mock()
 
-        self.query_handlers: Dict[str, Callable[[dict], Awaitable[JsonDict]]] = {}
+        self.query_handlers: dict[str, Callable[[dict], Awaitable[JsonDict]]] = {}
 
         def register_query_handler(
             query_type: str, handler: Callable[[dict], Awaitable[JsonDict]]
@@ -377,7 +377,7 @@ class ProfileTestCase(unittest.HomeserverTestCase):
             self.get_success(self.handler.check_avatar_size_and_mime_type(remote_mxc))
         )
 
-    def _setup_local_files(self, names_and_props: Dict[str, Dict[str, Any]]) -> None:
+    def _setup_local_files(self, names_and_props: dict[str, dict[str, Any]]) -> None:
         """Stores metadata about files in the database.
 
         Args:
diff --git a/tests/handlers/test_receipts.py b/tests/handlers/test_receipts.py
index 4febccbfcf..bb9e84d644 100644
--- a/tests/handlers/test_receipts.py
+++ b/tests/handlers/test_receipts.py
@@ -20,7 +20,6 @@
 #
 
 from copy import deepcopy
-from typing import List
 
 from twisted.internet.testing import MemoryReactor
 
@@ -334,7 +333,7 @@ class ReceiptsTestCase(unittest.HomeserverTestCase):
         self.assertEqual(events, original_events)
 
     def _test_filters_private(
-        self, events: List[JsonDict], expected_output: List[JsonDict]
+        self, events: list[JsonDict], expected_output: list[JsonDict]
     ) -> None:
         """Tests that the _filter_out_private returns the expected output"""
         filtered_events = self.event_source.filter_out_private_receipts(
diff --git a/tests/handlers/test_register.py b/tests/handlers/test_register.py
index 5e2eb8dee7..0db7f30b1f 100644
--- a/tests/handlers/test_register.py
+++ b/tests/handlers/test_register.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import Any, Collection, List, Optional, Tuple
+from typing import Any, Collection
 from unittest.mock import AsyncMock, Mock
 
 from twisted.internet.testing import MemoryReactor
@@ -63,10 +63,10 @@ class TestSpamChecker:
 
     async def check_registration_for_spam(
         self,
-        email_threepid: Optional[dict],
-        username: Optional[str],
-        request_info: Collection[Tuple[str, str]],
-        auth_provider_id: Optional[str],
+        email_threepid: dict | None,
+        username: str | None,
+        request_info: Collection[tuple[str, str]],
+        auth_provider_id: str | None,
     ) -> RegistrationBehaviour:
         return RegistrationBehaviour.ALLOW
 
@@ -74,10 +74,10 @@ class TestSpamChecker:
 class DenyAll(TestSpamChecker):
     async def check_registration_for_spam(
         self,
-        email_threepid: Optional[dict],
-        username: Optional[str],
-        request_info: Collection[Tuple[str, str]],
-        auth_provider_id: Optional[str],
+        email_threepid: dict | None,
+        username: str | None,
+        request_info: Collection[tuple[str, str]],
+        auth_provider_id: str | None,
     ) -> RegistrationBehaviour:
         return RegistrationBehaviour.DENY
 
@@ -85,10 +85,10 @@ class DenyAll(TestSpamChecker):
 class BanAll(TestSpamChecker):
     async def check_registration_for_spam(
         self,
-        email_threepid: Optional[dict],
-        username: Optional[str],
-        request_info: Collection[Tuple[str, str]],
-        auth_provider_id: Optional[str],
+        email_threepid: dict | None,
+        username: str | None,
+        request_info: Collection[tuple[str, str]],
+        auth_provider_id: str | None,
     ) -> RegistrationBehaviour:
         return RegistrationBehaviour.SHADOW_BAN
 
@@ -96,10 +96,10 @@ class BanAll(TestSpamChecker):
 class BanBadIdPUser(TestSpamChecker):
     async def check_registration_for_spam(
         self,
-        email_threepid: Optional[dict],
-        username: Optional[str],
-        request_info: Collection[Tuple[str, str]],
-        auth_provider_id: Optional[str] = None,
+        email_threepid: dict | None,
+        username: str | None,
+        request_info: Collection[tuple[str, str]],
+        auth_provider_id: str | None = None,
     ) -> RegistrationBehaviour:
         # Reject any user coming from CAS and whose username contains profanity
         if auth_provider_id == "cas" and username and "flimflob" in username:
@@ -113,9 +113,9 @@ class TestLegacyRegistrationSpamChecker:
 
     async def check_registration_for_spam(
         self,
-        email_threepid: Optional[dict],
-        username: Optional[str],
-        request_info: Collection[Tuple[str, str]],
+        email_threepid: dict | None,
+        username: str | None,
+        request_info: Collection[tuple[str, str]],
     ) -> RegistrationBehaviour:
         return RegistrationBehaviour.ALLOW
 
@@ -123,9 +123,9 @@ class TestLegacyRegistrationSpamChecker:
 class LegacyAllowAll(TestLegacyRegistrationSpamChecker):
     async def check_registration_for_spam(
         self,
-        email_threepid: Optional[dict],
-        username: Optional[str],
-        request_info: Collection[Tuple[str, str]],
+        email_threepid: dict | None,
+        username: str | None,
+        request_info: Collection[tuple[str, str]],
     ) -> RegistrationBehaviour:
         return RegistrationBehaviour.ALLOW
 
@@ -133,9 +133,9 @@ class LegacyAllowAll(TestLegacyRegistrationSpamChecker):
 class LegacyDenyAll(TestLegacyRegistrationSpamChecker):
     async def check_registration_for_spam(
         self,
-        email_threepid: Optional[dict],
-        username: Optional[str],
-        request_info: Collection[Tuple[str, str]],
+        email_threepid: dict | None,
+        username: str | None,
+        request_info: Collection[tuple[str, str]],
     ) -> RegistrationBehaviour:
         return RegistrationBehaviour.DENY
 
@@ -777,9 +777,9 @@ class RegistrationTestCase(unittest.HomeserverTestCase):
         self,
         requester: Requester,
         localpart: str,
-        displayname: Optional[str],
-        password_hash: Optional[str] = None,
-    ) -> Tuple[str, str]:
+        displayname: str | None,
+        password_hash: str | None = None,
+    ) -> tuple[str, str]:
         """Creates a new user if the user does not exist,
         else revokes all previous access tokens and generates a new one.
 
@@ -842,7 +842,7 @@ class RemoteAutoJoinTestCase(unittest.HomeserverTestCase):
 
         async def lookup_room_alias(
             *args: Any, **kwargs: Any
-        ) -> Tuple[RoomID, List[str]]:
+        ) -> tuple[RoomID, list[str]]:
             return RoomID.from_string(self.room_id), ["remotetest"]
 
         self.room_member_handler = Mock(spec=["update_membership", "lookup_room_alias"])
diff --git a/tests/handlers/test_room_list.py b/tests/handlers/test_room_list.py
index 45cef09b22..e7c4436d1d 100644
--- a/tests/handlers/test_room_list.py
+++ b/tests/handlers/test_room_list.py
@@ -1,5 +1,4 @@
 from http import HTTPStatus
-from typing import Optional, Set
 
 from synapse.rest import admin
 from synapse.rest.client import directory, login, room
@@ -18,7 +17,7 @@ class RoomListHandlerTestCase(unittest.HomeserverTestCase):
     ]
 
     def _create_published_room(
-        self, tok: str, extra_content: Optional[JsonDict] = None
+        self, tok: str, extra_content: JsonDict | None = None
     ) -> str:
         room_id = self.helper.create_room_as(tok=tok, extra_content=extra_content)
         channel = self.make_request(
@@ -69,7 +68,7 @@ class RoomListHandlerTestCase(unittest.HomeserverTestCase):
                 limit=50, from_federation_origin="test2"
             )
         )
-        room_ids_in_test2_list: Set[str] = {
+        room_ids_in_test2_list: set[str] = {
             entry["room_id"] for entry in room_list["chunk"]
         }
 
@@ -78,7 +77,7 @@ class RoomListHandlerTestCase(unittest.HomeserverTestCase):
                 limit=50, from_federation_origin="test3"
             )
         )
-        room_ids_in_test3_list: Set[str] = {
+        room_ids_in_test3_list: set[str] = {
             entry["room_id"] for entry in room_list["chunk"]
         }
 
diff --git a/tests/handlers/test_room_member.py b/tests/handlers/test_room_member.py
index 92c7c36602..8f9e27603e 100644
--- a/tests/handlers/test_room_member.py
+++ b/tests/handlers/test_room_member.py
@@ -50,7 +50,7 @@ class TestJoinsLimitedByPerRoomRateLimiter(FederatingHomeserverTestCase):
 
         self.intially_unjoined_room_id = f"!example:{self.OTHER_SERVER_NAME}"
 
-    @override_config({"rc_joins_per_room": {"per_second": 0, "burst_count": 2}})
+    @override_config({"rc_joins_per_room": {"per_second": 0.1, "burst_count": 2}})
     def test_local_user_local_joins_contribute_to_limit_and_are_limited(self) -> None:
         # The rate limiter has accumulated one token from Alice's join after the create
         # event.
@@ -76,7 +76,7 @@ class TestJoinsLimitedByPerRoomRateLimiter(FederatingHomeserverTestCase):
             by=0.5,
         )
 
-    @override_config({"rc_joins_per_room": {"per_second": 0, "burst_count": 2}})
+    @override_config({"rc_joins_per_room": {"per_second": 0.1, "burst_count": 2}})
     def test_local_user_profile_edits_dont_contribute_to_limit(self) -> None:
         # The rate limiter has accumulated one token from Alice's join after the create
         # event. Alice should still be able to change her displayname.
@@ -100,7 +100,7 @@ class TestJoinsLimitedByPerRoomRateLimiter(FederatingHomeserverTestCase):
             )
         )
 
-    @override_config({"rc_joins_per_room": {"per_second": 0, "burst_count": 1}})
+    @override_config({"rc_joins_per_room": {"per_second": 0.1, "burst_count": 1}})
     def test_remote_joins_contribute_to_rate_limit(self) -> None:
         # Join once, to fill the rate limiter bucket.
         #
@@ -248,7 +248,7 @@ class TestReplicatedJoinsLimitedByPerRoomRateLimiter(BaseMultiWorkerStreamTestCa
         self.room_id = self.helper.create_room_as(self.alice, tok=self.alice_token)
         self.intially_unjoined_room_id = "!example:otherhs"
 
-    @override_config({"rc_joins_per_room": {"per_second": 0, "burst_count": 2}})
+    @override_config({"rc_joins_per_room": {"per_second": 0.01, "burst_count": 2}})
     def test_local_users_joining_on_another_worker_contribute_to_rate_limit(
         self,
     ) -> None:
diff --git a/tests/handlers/test_room_policy.py b/tests/handlers/test_room_policy.py
index 00da1d942f..ff212ab06e 100644
--- a/tests/handlers/test_room_policy.py
+++ b/tests/handlers/test_room_policy.py
@@ -12,7 +12,6 @@
 # <https://www.gnu.org/licenses/agpl-3.0.html>.
 #
 #
-from typing import Optional
 from unittest import mock
 
 import signedjson
@@ -113,7 +112,7 @@ class RoomPolicyTestCase(unittest.FederatingHomeserverTestCase):
         async def get_policy_recommendation_for_pdu(
             destination: str,
             pdu: EventBase,
-            timeout: Optional[int] = None,
+            timeout: int | None = None,
         ) -> JsonDict:
             self.call_count += 1
             self.assertEqual(destination, self.OTHER_SERVER_NAME)
@@ -128,8 +127,8 @@ class RoomPolicyTestCase(unittest.FederatingHomeserverTestCase):
 
         # Mock policy server actions on signing events
         async def policy_server_signs_event(
-            destination: str, pdu: EventBase, timeout: Optional[int] = None
-        ) -> Optional[JsonDict]:
+            destination: str, pdu: EventBase, timeout: int | None = None
+        ) -> JsonDict | None:
             sigs = compute_event_signature(
                 pdu.room_version,
                 pdu.get_dict(),
@@ -139,8 +138,8 @@ class RoomPolicyTestCase(unittest.FederatingHomeserverTestCase):
             return sigs
 
         async def policy_server_signs_event_with_wrong_key(
-            destination: str, pdu: EventBase, timeout: Optional[int] = None
-        ) -> Optional[JsonDict]:
+            destination: str, pdu: EventBase, timeout: int | None = None
+        ) -> JsonDict | None:
             sk = signedjson.key.generate_signing_key("policy_server")
             sigs = compute_event_signature(
                 pdu.room_version,
@@ -151,13 +150,13 @@ class RoomPolicyTestCase(unittest.FederatingHomeserverTestCase):
             return sigs
 
         async def policy_server_refuses_to_sign_event(
-            destination: str, pdu: EventBase, timeout: Optional[int] = None
-        ) -> Optional[JsonDict]:
+            destination: str, pdu: EventBase, timeout: int | None = None
+        ) -> JsonDict | None:
             return {}
 
         async def policy_server_event_sign_error(
-            destination: str, pdu: EventBase, timeout: Optional[int] = None
-        ) -> Optional[JsonDict]:
+            destination: str, pdu: EventBase, timeout: int | None = None
+        ) -> JsonDict | None:
             return None
 
         self.policy_server_signs_event = policy_server_signs_event
@@ -167,7 +166,7 @@ class RoomPolicyTestCase(unittest.FederatingHomeserverTestCase):
             policy_server_signs_event_with_wrong_key
         )
 
-    def _add_policy_server_to_room(self, public_key: Optional[str] = None) -> None:
+    def _add_policy_server_to_room(self, public_key: str | None = None) -> None:
         # Inject a member event into the room
         policy_user_id = f"@policy:{self.OTHER_SERVER_NAME}"
         self.get_success(
@@ -442,7 +441,7 @@ class RoomPolicyTestCase(unittest.FederatingHomeserverTestCase):
             f"event did not include policy server signature, signature block = {ev.get('signatures', None)}",
         )
 
-    def _fetch_federation_event(self, event_id: str) -> Optional[JsonDict]:
+    def _fetch_federation_event(self, event_id: str) -> JsonDict | None:
         # Request federation events to see the signatures
         channel = self.make_request(
             "POST",
diff --git a/tests/handlers/test_room_summary.py b/tests/handlers/test_room_summary.py
index 00592b9871..ee65cb1afb 100644
--- a/tests/handlers/test_room_summary.py
+++ b/tests/handlers/test_room_summary.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Any, Dict, Iterable, List, Optional, Set, Tuple
+from typing import Any, Iterable
 from unittest import mock
 
 from twisted.internet.defer import ensureDeferred
@@ -49,7 +49,7 @@ from tests.unittest import override_config
 
 
 def _create_event(
-    room_id: str, order: Optional[Any] = None, origin_server_ts: int = 0
+    room_id: str, order: Any | None = None, origin_server_ts: int = 0
 ) -> mock.Mock:
     result = mock.Mock(name=room_id)
     result.room_id = room_id
@@ -60,7 +60,7 @@ def _create_event(
     return result
 
 
-def _order(*events: mock.Mock) -> List[mock.Mock]:
+def _order(*events: mock.Mock) -> list[mock.Mock]:
     return sorted(events, key=_child_events_comparison_key)
 
 
@@ -151,8 +151,8 @@ class SpaceSummaryTestCase(unittest.HomeserverTestCase):
         space_id: str,
         room_id: str,
         token: str,
-        order: Optional[str] = None,
-        via: Optional[List[str]] = None,
+        order: str | None = None,
+        via: list[str] | None = None,
     ) -> None:
         """Add a child room to a space."""
         if via is None:
@@ -170,7 +170,7 @@ class SpaceSummaryTestCase(unittest.HomeserverTestCase):
         )
 
     def _assert_hierarchy(
-        self, result: JsonDict, rooms_and_children: Iterable[Tuple[str, Iterable[str]]]
+        self, result: JsonDict, rooms_and_children: Iterable[tuple[str, Iterable[str]]]
     ) -> None:
         """
         Assert that the expected room IDs are in the response.
@@ -393,7 +393,7 @@ class SpaceSummaryTestCase(unittest.HomeserverTestCase):
         self._assert_hierarchy(result2, [(self.space, [self.room])])
 
     def _create_room_with_join_rule(
-        self, join_rule: str, room_version: Optional[str] = None, **extra_content: Any
+        self, join_rule: str, room_version: str | None = None, **extra_content: Any
     ) -> str:
         """Create a room with the given join rule and add it to the space."""
         room_id = self.helper.create_room_as(
@@ -547,7 +547,7 @@ class SpaceSummaryTestCase(unittest.HomeserverTestCase):
         )
         # The result should have the space and all of the links, plus some of the
         # rooms and a pagination token.
-        expected: List[Tuple[str, Iterable[str]]] = [(self.space, room_ids)]
+        expected: list[tuple[str, Iterable[str]]] = [(self.space, room_ids)]
         expected += [(room_id, ()) for room_id in room_ids[:6]]
         self._assert_hierarchy(result, expected)
         self.assertIn("next_batch", result)
@@ -646,7 +646,7 @@ class SpaceSummaryTestCase(unittest.HomeserverTestCase):
                 create_requester(self.user), self.space, max_depth=0
             )
         )
-        expected: List[Tuple[str, Iterable[str]]] = [(spaces[0], [rooms[0], spaces[1]])]
+        expected: list[tuple[str, Iterable[str]]] = [(spaces[0], [rooms[0], spaces[1]])]
         self._assert_hierarchy(result, expected)
 
         # A single additional layer.
@@ -740,7 +740,7 @@ class SpaceSummaryTestCase(unittest.HomeserverTestCase):
 
         async def summarize_remote_room_hierarchy(
             _self: Any, room: Any, suggested_only: bool
-        ) -> Tuple[Optional[_RoomEntry], Dict[str, JsonDict], Set[str]]:
+        ) -> tuple[_RoomEntry | None, dict[str, JsonDict], set[str]]:
             return requested_room_entry, {subroom: child_room}, set()
 
         # Add a room to the space which is on another server.
@@ -793,7 +793,7 @@ class SpaceSummaryTestCase(unittest.HomeserverTestCase):
 
         async def summarize_remote_room_hierarchy(
             _self: Any, room: Any, suggested_only: bool
-        ) -> Tuple[Optional[_RoomEntry], Dict[str, JsonDict], Set[str]]:
+        ) -> tuple[_RoomEntry | None, dict[str, JsonDict], set[str]]:
             return requested_room_entry, {fed_subroom: child_room}, set()
 
         expected = [
@@ -921,7 +921,7 @@ class SpaceSummaryTestCase(unittest.HomeserverTestCase):
 
         async def summarize_remote_room_hierarchy(
             _self: Any, room: Any, suggested_only: bool
-        ) -> Tuple[Optional[_RoomEntry], Dict[str, JsonDict], Set[str]]:
+        ) -> tuple[_RoomEntry | None, dict[str, JsonDict], set[str]]:
             return subspace_room_entry, dict(children_rooms), set()
 
         # Add a room to the space which is on another server.
@@ -985,7 +985,7 @@ class SpaceSummaryTestCase(unittest.HomeserverTestCase):
 
         async def summarize_remote_room_hierarchy(
             _self: Any, room: Any, suggested_only: bool
-        ) -> Tuple[Optional[_RoomEntry], Dict[str, JsonDict], Set[str]]:
+        ) -> tuple[_RoomEntry | None, dict[str, JsonDict], set[str]]:
             return fed_room_entry, {}, set()
 
         # Add a room to the space which is on another server.
@@ -1120,7 +1120,7 @@ class SpaceSummaryTestCase(unittest.HomeserverTestCase):
 
         async def summarize_remote_room_hierarchy(
             _self: Any, room: Any, suggested_only: bool
-        ) -> Tuple[Optional[_RoomEntry], Dict[str, JsonDict], Set[str]]:
+        ) -> tuple[_RoomEntry | None, dict[str, JsonDict], set[str]]:
             return requested_room_entry, {fed_subroom: child_room}, set()
 
         expected = [
@@ -1233,7 +1233,7 @@ class RoomSummaryTestCase(unittest.HomeserverTestCase):
 
         async def summarize_remote_room_hierarchy(
             _self: Any, room: Any, suggested_only: bool
-        ) -> Tuple[Optional[_RoomEntry], Dict[str, JsonDict], Set[str]]:
+        ) -> tuple[_RoomEntry | None, dict[str, JsonDict], set[str]]:
             return requested_room_entry, {}, set()
 
         with mock.patch(
diff --git a/tests/handlers/test_saml.py b/tests/handlers/test_saml.py
index f7cbf91113..c2aeab5f7e 100644
--- a/tests/handlers/test_saml.py
+++ b/tests/handlers/test_saml.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import Any, Dict, Optional, Set, Tuple
+from typing import Any
 from unittest.mock import AsyncMock, Mock
 
 import attr
@@ -61,7 +61,7 @@ BASE_URL = "https://synapse/"
 class FakeAuthnResponse:
     ava = attr.ib(type=dict)
     assertions = attr.ib(type=list, factory=list)
-    in_response_to = attr.ib(type=Optional[str], default=None)
+    in_response_to = attr.ib(type=(str | None), default=None)
 
 
 class TestMappingProvider:
@@ -73,7 +73,7 @@ class TestMappingProvider:
         return None
 
     @staticmethod
-    def get_saml_attributes(config: None) -> Tuple[Set[str], Set[str]]:
+    def get_saml_attributes(config: None) -> tuple[set[str], set[str]]:
         return {"uid"}, {"displayName"}
 
     def get_remote_user_id(
@@ -102,10 +102,10 @@ class TestRedirectMappingProvider(TestMappingProvider):
 
 
 class SamlHandlerTestCase(HomeserverTestCase):
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         config = super().default_config()
         config["public_baseurl"] = BASE_URL
-        saml_config: Dict[str, Any] = {
+        saml_config: dict[str, Any] = {
             "sp_config": {"metadata": {}},
             # Disable grandfathering.
             "grandfathered_mxid_source_attribute": None,
diff --git a/tests/handlers/test_send_email.py b/tests/handlers/test_send_email.py
index 5f7839c82c..eea88cd136 100644
--- a/tests/handlers/test_send_email.py
+++ b/tests/handlers/test_send_email.py
@@ -20,7 +20,7 @@
 #
 
 
-from typing import Callable, List, Tuple, Type, Union
+from typing import Callable
 from unittest.mock import patch
 
 from zope.interface import implementer
@@ -58,18 +58,18 @@ def TestingESMTPTLSClientFactory(
 class _DummyMessageDelivery:
     def __init__(self) -> None:
         # (recipient, message) tuples
-        self.messages: List[Tuple[smtp.Address, bytes]] = []
+        self.messages: list[tuple[smtp.Address, bytes]] = []
 
     def receivedHeader(
         self,
-        helo: Tuple[bytes, bytes],
+        helo: tuple[bytes, bytes],
         origin: smtp.Address,
-        recipients: List[smtp.User],
+        recipients: list[smtp.User],
     ) -> None:
         return None
 
     def validateFrom(
-        self, helo: Tuple[bytes, bytes], origin: smtp.Address
+        self, helo: tuple[bytes, bytes], origin: smtp.Address
     ) -> smtp.Address:
         return origin
 
@@ -89,7 +89,7 @@ class _DummyMessage:
     def __init__(self, delivery: _DummyMessageDelivery, user: smtp.User):
         self._delivery = delivery
         self._user = user
-        self._buffer: List[bytes] = []
+        self._buffer: list[bytes] = []
 
     def lineReceived(self, line: bytes) -> None:
         self._buffer.append(line)
@@ -104,7 +104,7 @@ class _DummyMessage:
 
 
 class SendEmailHandlerTestCaseIPv4(HomeserverTestCase):
-    ip_class: Union[Type[IPv4Address], Type[IPv6Address]] = IPv4Address
+    ip_class: type[IPv4Address] | type[IPv6Address] = IPv4Address
 
     def setUp(self) -> None:
         super().setUp()
diff --git a/tests/handlers/test_sliding_sync.py b/tests/handlers/test_sliding_sync.py
index 1ffd15cadb..4582906441 100644
--- a/tests/handlers/test_sliding_sync.py
+++ b/tests/handlers/test_sliding_sync.py
@@ -18,7 +18,7 @@
 #
 #
 import logging
-from typing import AbstractSet, Dict, Mapping, Optional, Set, Tuple
+from typing import AbstractSet, Mapping
 from unittest.mock import patch
 
 import attr
@@ -62,7 +62,7 @@ class RoomSyncConfigTestCase(TestCase):
         self,
         actual: RoomSyncConfig,
         expected: RoomSyncConfig,
-        message_prefix: Optional[str] = None,
+        message_prefix: str | None = None,
     ) -> None:
         self.assertEqual(actual.timeline_limit, expected.timeline_limit, message_prefix)
 
@@ -3277,8 +3277,8 @@ class FilterRoomsRelevantForSyncTestCase(HomeserverTestCase):
         self,
         user: UserID,
         to_token: StreamToken,
-        from_token: Optional[StreamToken],
-    ) -> Tuple[Dict[str, RoomsForUserType], AbstractSet[str], AbstractSet[str]]:
+        from_token: StreamToken | None,
+    ) -> tuple[dict[str, RoomsForUserType], AbstractSet[str], AbstractSet[str]]:
         """
         Get the rooms the user should be syncing with
         """
@@ -3614,8 +3614,8 @@ class SortRoomsTestCase(HomeserverTestCase):
         self,
         user: UserID,
         to_token: StreamToken,
-        from_token: Optional[StreamToken],
-    ) -> Tuple[Dict[str, RoomsForUserType], AbstractSet[str], AbstractSet[str]]:
+        from_token: StreamToken | None,
+    ) -> tuple[dict[str, RoomsForUserType], AbstractSet[str], AbstractSet[str]]:
         """
         Get the rooms the user should be syncing with
         """
@@ -3824,14 +3824,14 @@ class SortRoomsTestCase(HomeserverTestCase):
 
 @attr.s(slots=True, auto_attribs=True, frozen=True)
 class RequiredStateChangesTestParameters:
-    previous_required_state_map: Dict[str, Set[str]]
-    request_required_state_map: Dict[str, Set[str]]
+    previous_required_state_map: dict[str, set[str]]
+    request_required_state_map: dict[str, set[str]]
     state_deltas: StateMap[str]
-    expected_with_state_deltas: Tuple[
-        Optional[Mapping[str, AbstractSet[str]]], StateFilter
+    expected_with_state_deltas: tuple[
+        Mapping[str, AbstractSet[str]] | None, StateFilter
     ]
-    expected_without_state_deltas: Tuple[
-        Optional[Mapping[str, AbstractSet[str]]], StateFilter
+    expected_without_state_deltas: tuple[
+        Mapping[str, AbstractSet[str]] | None, StateFilter
     ]
 
 
@@ -4785,7 +4785,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
         self,
         _test_label: str,
         event_type: str,
-        extra_state_keys: Set[str],
+        extra_state_keys: set[str],
     ) -> None:
         """
         Test that we limit the number of state_keys that we remember but always include
diff --git a/tests/handlers/test_sso.py b/tests/handlers/test_sso.py
index b09d0a42f5..95595b8ff9 100644
--- a/tests/handlers/test_sso.py
+++ b/tests/handlers/test_sso.py
@@ -18,7 +18,7 @@
 #
 #
 from http import HTTPStatus
-from typing import BinaryIO, Callable, Dict, List, Optional, Tuple
+from typing import BinaryIO, Callable
 from unittest.mock import Mock
 
 from twisted.internet.testing import MemoryReactor
@@ -117,10 +117,10 @@ class TestSSOHandler(unittest.HomeserverTestCase):
 async def mock_get_file(
     url: str,
     output_stream: BinaryIO,
-    max_size: Optional[int] = None,
-    headers: Optional[RawHeaders] = None,
-    is_allowed_content_type: Optional[Callable[[str], bool]] = None,
-) -> Tuple[int, Dict[bytes, List[bytes]], str, int]:
+    max_size: int | None = None,
+    headers: RawHeaders | None = None,
+    is_allowed_content_type: Callable[[str], bool] | None = None,
+) -> tuple[int, dict[bytes, list[bytes]], str, int]:
     fake_response = FakeResponse(code=404)
     if url == "http://my.server/me.png":
         fake_response = FakeResponse(
diff --git a/tests/handlers/test_stats.py b/tests/handlers/test_stats.py
index abec5c2e39..0072327044 100644
--- a/tests/handlers/test_stats.py
+++ b/tests/handlers/test_stats.py
@@ -18,7 +18,7 @@
 #
 #
 
-from typing import Any, Dict, List, Optional, Tuple, cast
+from typing import Any, cast
 
 from twisted.internet.testing import MemoryReactor
 
@@ -74,9 +74,9 @@ class StatsRoomTests(unittest.HomeserverTestCase):
             )
         )
 
-    async def get_all_room_state(self) -> List[Optional[str]]:
+    async def get_all_room_state(self) -> list[str | None]:
         rows = cast(
-            List[Tuple[Optional[str]]],
+            list[tuple[str | None]],
             await self.store.db_pool.simple_select_list(
                 "room_stats_state", None, retcols=("topic",)
             ),
@@ -85,7 +85,7 @@ class StatsRoomTests(unittest.HomeserverTestCase):
 
     def _get_current_stats(
         self, stats_type: str, stat_id: str
-    ) -> Optional[Dict[str, Any]]:
+    ) -> dict[str, Any] | None:
         table, id_col = stats.TYPE_TO_TABLE[stats_type]
 
         cols = list(stats.ABSOLUTE_STATS_FIELDS[stats_type])
diff --git a/tests/handlers/test_sync.py b/tests/handlers/test_sync.py
index c61788fe90..18ec2ca6b6 100644
--- a/tests/handlers/test_sync.py
+++ b/tests/handlers/test_sync.py
@@ -18,7 +18,7 @@
 #
 #
 from http import HTTPStatus
-from typing import Collection, ContextManager, List, Optional
+from typing import Collection, ContextManager
 from unittest.mock import AsyncMock, Mock, patch
 
 from parameterized import parameterized, parameterized_class
@@ -872,7 +872,7 @@ class SyncTestCase(tests.unittest.HomeserverTestCase):
             # ... And the state should be empty
             self.assertEqual(sync_room_result.state, {})
 
-    def _patch_get_latest_events(self, latest_events: List[str]) -> ContextManager:
+    def _patch_get_latest_events(self, latest_events: list[str]) -> ContextManager:
         """Monkey-patch `get_prev_events_for_room`
 
         Returns a context manager which will replace the implementation of
@@ -893,7 +893,7 @@ class SyncTestCase(tests.unittest.HomeserverTestCase):
         federation_event_handler = self.hs.get_federation_event_handler()
 
         async def _check_event_auth(
-            origin: Optional[str], event: EventBase, context: EventContext
+            origin: str | None, event: EventBase, context: EventContext
         ) -> None:
             pass
 
@@ -902,7 +902,7 @@ class SyncTestCase(tests.unittest.HomeserverTestCase):
 
         async def _check_sigs_and_hash_for_pulled_events_and_fetch(
             dest: str, pdus: Collection[EventBase], room_version: RoomVersion
-        ) -> List[EventBase]:
+        ) -> list[EventBase]:
             return list(pdus)
 
         self.client._check_sigs_and_hash_for_pulled_events_and_fetch = (  # type: ignore[method-assign]
@@ -1117,8 +1117,8 @@ class SyncTestCase(tests.unittest.HomeserverTestCase):
 
 def generate_sync_config(
     user_id: str,
-    device_id: Optional[str] = "device_id",
-    filter_collection: Optional[FilterCollection] = None,
+    device_id: str | None = "device_id",
+    filter_collection: FilterCollection | None = None,
     use_state_after: bool = False,
 ) -> SyncConfig:
     """Generate a sync config (with a unique request key).
diff --git a/tests/handlers/test_typing.py b/tests/handlers/test_typing.py
index 4d2807151e..70557a4a5f 100644
--- a/tests/handlers/test_typing.py
+++ b/tests/handlers/test_typing.py
@@ -21,7 +21,6 @@
 
 
 import json
-from typing import Dict, List, Set
 from unittest.mock import ANY, AsyncMock, Mock, call
 
 from netaddr import IPSet
@@ -79,15 +78,17 @@ class TypingNotificationsTestCase(unittest.HomeserverTestCase):
     ) -> HomeServer:
         # we mock out the keyring so as to skip the authentication check on the
         # federation API call.
-        mock_keyring = Mock(spec=["verify_json_for_server"])
+        mock_keyring = Mock(spec=["verify_json_for_server", "shutdown"])
         mock_keyring.verify_json_for_server = AsyncMock(return_value=True)
+        mock_keyring.shutdown = Mock()
 
         # we mock out the federation client too
         self.mock_federation_client = AsyncMock(spec=["put_json"])
         self.mock_federation_client.put_json.return_value = (200, "OK")
         self.mock_federation_client.agent = MatrixFederationAgent(
             server_name="OUR_STUB_HOMESERVER_NAME",
-            reactor=reactor,
+            reactor=self.reactor,
+            clock=self.clock,
             tls_client_options_factory=None,
             user_agent=b"SynapseInTrialTest/0.0.0",
             ip_allowlist=None,
@@ -96,7 +97,7 @@ class TypingNotificationsTestCase(unittest.HomeserverTestCase):
         )
 
         # the tests assume that we are starting at unix time 1000
-        reactor.pump((1000,))
+        self.reactor.pump((1000,))
 
         self.mock_hs_notifier = Mock()
         hs = self.setup_test_homeserver(
@@ -108,7 +109,7 @@ class TypingNotificationsTestCase(unittest.HomeserverTestCase):
 
         return hs
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         d = super().create_resource_dict()
         d["/_matrix/federation"] = TransportLayerServer(self.hs)
         return d
@@ -141,7 +142,7 @@ class TypingNotificationsTestCase(unittest.HomeserverTestCase):
             return_value=None
         )
 
-        self.room_members: List[UserID] = []
+        self.room_members: list[UserID] = []
 
         async def check_user_in_room(room_id: str, requester: Requester) -> None:
             if requester.user.to_string() not in [
@@ -161,7 +162,7 @@ class TypingNotificationsTestCase(unittest.HomeserverTestCase):
             side_effect=check_host_in_room
         )
 
-        async def get_current_hosts_in_room(room_id: str) -> Set[str]:
+        async def get_current_hosts_in_room(room_id: str) -> set[str]:
             return {member.domain for member in self.room_members}
 
         hs.get_storage_controllers().state.get_current_hosts_in_room = Mock(  # type: ignore[method-assign]
@@ -172,7 +173,7 @@ class TypingNotificationsTestCase(unittest.HomeserverTestCase):
             side_effect=get_current_hosts_in_room
         )
 
-        async def get_users_in_room(room_id: str) -> Set[str]:
+        async def get_users_in_room(room_id: str) -> set[str]:
             return {str(u) for u in self.room_members}
 
         self.datastore.get_users_in_room = Mock(side_effect=get_users_in_room)
diff --git a/tests/handlers/test_user_directory.py b/tests/handlers/test_user_directory.py
index 1ba0be51a2..f50fa1f4a0 100644
--- a/tests/handlers/test_user_directory.py
+++ b/tests/handlers/test_user_directory.py
@@ -17,7 +17,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Any, Tuple
+from typing import Any
 from unittest.mock import AsyncMock, Mock, patch
 from urllib.parse import quote
 
@@ -313,7 +313,7 @@ class UserDirectoryTestCase(unittest.HomeserverTestCase):
 
     def _create_rooms_and_inject_memberships(
         self, creator: str, token: str, joiner: str
-    ) -> Tuple[str, str]:
+    ) -> tuple[str, str]:
         """Create a public and private room as a normal user.
         Then get the `joiner` into those rooms.
         """
diff --git a/tests/http/__init__.py b/tests/http/__init__.py
index 3c20e5e442..b19a484004 100644
--- a/tests/http/__init__.py
+++ b/tests/http/__init__.py
@@ -19,7 +19,6 @@
 #
 import os.path
 import subprocess
-from typing import List
 
 from incremental import Version
 from zope.interface import implementer
@@ -85,7 +84,7 @@ subjectAltName = %(sanentries)s
 """
 
 
-def create_test_cert_file(sanlist: List[bytes]) -> str:
+def create_test_cert_file(sanlist: list[bytes]) -> str:
     """build an x509 certificate file
 
     Args:
@@ -151,7 +150,7 @@ class TestServerTLSConnectionFactory:
     """An SSL connection creator which returns connections which present a certificate
     signed by our test CA."""
 
-    def __init__(self, sanlist: List[bytes]):
+    def __init__(self, sanlist: list[bytes]):
         """
         Args:
             sanlist: a list of subjectAltName values for the cert
@@ -166,7 +165,7 @@ class TestServerTLSConnectionFactory:
 
 
 def wrap_server_factory_for_tls(
-    factory: IProtocolFactory, clock: IReactorTime, sanlist: List[bytes]
+    factory: IProtocolFactory, clock: IReactorTime, sanlist: list[bytes]
 ) -> TLSMemoryBIOFactory:
     """Wrap an existing Protocol Factory with a test TLSMemoryBIOFactory
 
diff --git a/tests/http/federation/test_matrix_federation_agent.py b/tests/http/federation/test_matrix_federation_agent.py
index a5e1b7c284..49ecaa30ff 100644
--- a/tests/http/federation/test_matrix_federation_agent.py
+++ b/tests/http/federation/test_matrix_federation_agent.py
@@ -20,7 +20,7 @@
 import base64
 import logging
 import os
-from typing import Generator, List, Optional, cast
+from typing import Generator, cast
 from unittest.mock import AsyncMock, call, patch
 
 import treq
@@ -65,7 +65,7 @@ from synapse.util.caches.ttlcache import TTLCache
 
 from tests import unittest
 from tests.http import dummy_address, get_test_ca_cert_file, wrap_server_factory_for_tls
-from tests.server import FakeTransport, ThreadedMemoryReactorClock
+from tests.server import FakeTransport, get_clock
 from tests.utils import checked_cast, default_config
 
 logger = logging.getLogger(__name__)
@@ -73,7 +73,7 @@ logger = logging.getLogger(__name__)
 
 class MatrixFederationAgentTests(unittest.TestCase):
     def setUp(self) -> None:
-        self.reactor = ThreadedMemoryReactorClock()
+        self.reactor, self.clock = get_clock()
 
         self.mock_resolver = AsyncMock(spec=SrvResolver)
 
@@ -85,7 +85,7 @@ class MatrixFederationAgentTests(unittest.TestCase):
 
         self.tls_factory = FederationPolicyForHTTPS(config)
 
-        self.well_known_cache: TTLCache[bytes, Optional[bytes]] = TTLCache(
+        self.well_known_cache: TTLCache[bytes, bytes | None] = TTLCache(
             cache_name="test_cache",
             server_name="test_server",
             timer=self.reactor.seconds,
@@ -98,6 +98,7 @@ class MatrixFederationAgentTests(unittest.TestCase):
         self.well_known_resolver = WellKnownResolver(
             server_name="OUR_STUB_HOMESERVER_NAME",
             reactor=self.reactor,
+            clock=self.clock,
             agent=Agent(self.reactor, contextFactory=self.tls_factory),
             user_agent=b"test-agent",
             well_known_cache=self.well_known_cache,
@@ -108,8 +109,8 @@ class MatrixFederationAgentTests(unittest.TestCase):
         self,
         client_factory: IProtocolFactory,
         ssl: bool = True,
-        expected_sni: Optional[bytes] = None,
-        tls_sanlist: Optional[List[bytes]] = None,
+        expected_sni: bytes | None = None,
+        tls_sanlist: list[bytes] | None = None,
     ) -> HTTPChannel:
         """Builds a test server, and completes the outgoing client connection
         Args:
@@ -227,7 +228,7 @@ class MatrixFederationAgentTests(unittest.TestCase):
         client_factory: IProtocolFactory,
         expected_sni: bytes,
         content: bytes,
-        response_headers: Optional[dict] = None,
+        response_headers: dict | None = None,
     ) -> HTTPChannel:
         """Handle an outgoing HTTPs connection: wire it up to a server, check that the
         request is for a .well-known, and send the response.
@@ -256,7 +257,7 @@ class MatrixFederationAgentTests(unittest.TestCase):
         self,
         request: Request,
         content: bytes,
-        headers: Optional[dict] = None,
+        headers: dict | None = None,
     ) -> None:
         """Check that an incoming request looks like a valid .well-known request, and
         send back the response.
@@ -280,6 +281,7 @@ class MatrixFederationAgentTests(unittest.TestCase):
         return MatrixFederationAgent(
             server_name="OUR_STUB_HOMESERVER_NAME",
             reactor=cast(ISynapseReactor, self.reactor),
+            clock=self.clock,
             tls_client_options_factory=self.tls_factory,
             user_agent=b"test-agent",  # Note that this is unused since _well_known_resolver is provided.
             ip_allowlist=IPSet(),
@@ -395,7 +397,7 @@ class MatrixFederationAgentTests(unittest.TestCase):
     def _do_get_via_proxy(
         self,
         expect_proxy_ssl: bool = False,
-        expected_auth_credentials: Optional[bytes] = None,
+        expected_auth_credentials: bytes | None = None,
     ) -> None:
         """Send a https federation request via an agent and check that it is correctly
             received at the proxy and client. The proxy can use either http or https.
@@ -1024,6 +1026,7 @@ class MatrixFederationAgentTests(unittest.TestCase):
         agent = MatrixFederationAgent(
             server_name="OUR_STUB_HOMESERVER_NAME",
             reactor=self.reactor,
+            clock=self.clock,
             tls_client_options_factory=tls_factory,
             user_agent=b"test-agent",  # This is unused since _well_known_resolver is passed below.
             ip_allowlist=IPSet(),
@@ -1033,6 +1036,7 @@ class MatrixFederationAgentTests(unittest.TestCase):
             _well_known_resolver=WellKnownResolver(
                 server_name="OUR_STUB_HOMESERVER_NAME",
                 reactor=cast(ISynapseReactor, self.reactor),
+                clock=self.clock,
                 agent=Agent(self.reactor, contextFactory=tls_factory),
                 user_agent=b"test-agent",
                 well_known_cache=self.well_known_cache,
diff --git a/tests/http/federation/test_srv_resolver.py b/tests/http/federation/test_srv_resolver.py
index 4fd0fb9226..54f3168a01 100644
--- a/tests/http/federation/test_srv_resolver.py
+++ b/tests/http/federation/test_srv_resolver.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Dict, Generator, List, Tuple, cast
+from typing import Generator, cast
 from unittest.mock import Mock
 
 from twisted.internet import defer
@@ -30,7 +30,7 @@ from synapse.http.federation.srv_resolver import Server, SrvResolver
 from synapse.logging.context import LoggingContext, current_context
 
 from tests import unittest
-from tests.utils import MockClock
+from tests.server import get_clock
 
 
 class SrvResolverTestCase(unittest.TestCase):
@@ -44,20 +44,20 @@ class SrvResolverTestCase(unittest.TestCase):
             type=dns.SRV, payload=dns.Record_SRV(target=host_name)
         )
 
-        result_deferred: "Deferred[Tuple[List[dns.RRHeader], None, None]]" = Deferred()
+        result_deferred: "Deferred[tuple[list[dns.RRHeader], None, None]]" = Deferred()
         dns_client_mock.lookupService.return_value = result_deferred
 
-        cache: Dict[bytes, List[Server]] = {}
+        cache: dict[bytes, list[Server]] = {}
         resolver = SrvResolver(dns_client=dns_client_mock, cache=cache)
 
         @defer.inlineCallbacks
-        def do_lookup() -> Generator["Deferred[object]", object, List[Server]]:
+        def do_lookup() -> Generator["Deferred[object]", object, list[Server]]:
             with LoggingContext(
                 name="one",
                 server_name="test_server",
             ) as ctx:
                 resolve_d = resolver.resolve_service(service_name)
-                result: List[Server]
+                result: list[Server]
                 result = yield defer.ensureDeferred(resolve_d)  # type: ignore[assignment]
 
                 # should have restored our context
@@ -95,7 +95,7 @@ class SrvResolverTestCase(unittest.TestCase):
         cache = {service_name: [cast(Server, entry)]}
         resolver = SrvResolver(dns_client=dns_client_mock, cache=cache)
 
-        servers: List[Server]
+        servers: list[Server]
         servers = yield defer.ensureDeferred(resolver.resolve_service(service_name))  # type: ignore[assignment]
 
         dns_client_mock.lookupService.assert_called_once_with(service_name)
@@ -105,7 +105,7 @@ class SrvResolverTestCase(unittest.TestCase):
 
     @defer.inlineCallbacks
     def test_from_cache(self) -> Generator["Deferred[object]", object, None]:
-        clock = MockClock()
+        reactor, clock = get_clock()
 
         dns_client_mock = Mock(spec_set=["lookupService"])
         dns_client_mock.lookupService = Mock(spec_set=[])
@@ -122,7 +122,7 @@ class SrvResolverTestCase(unittest.TestCase):
             dns_client=dns_client_mock, cache=cache, get_time=clock.time
         )
 
-        servers: List[Server]
+        servers: list[Server]
         servers = yield defer.ensureDeferred(resolver.resolve_service(service_name))  # type: ignore[assignment]
 
         self.assertFalse(dns_client_mock.lookupService.called)
@@ -138,7 +138,7 @@ class SrvResolverTestCase(unittest.TestCase):
 
         service_name = b"test_service.example.com"
 
-        cache: Dict[bytes, List[Server]] = {}
+        cache: dict[bytes, list[Server]] = {}
         resolver = SrvResolver(dns_client=dns_client_mock, cache=cache)
 
         with self.assertRaises(error.DNSServerError):
@@ -152,10 +152,10 @@ class SrvResolverTestCase(unittest.TestCase):
 
         service_name = b"test_service.example.com"
 
-        cache: Dict[bytes, List[Server]] = {}
+        cache: dict[bytes, list[Server]] = {}
         resolver = SrvResolver(dns_client=dns_client_mock, cache=cache)
 
-        servers: List[Server]
+        servers: list[Server]
         servers = yield defer.ensureDeferred(resolver.resolve_service(service_name))  # type: ignore[assignment]
 
         self.assertEqual(len(servers), 0)
@@ -167,10 +167,10 @@ class SrvResolverTestCase(unittest.TestCase):
         """
         service_name = b"test_service.example.com"
 
-        lookup_deferred: "Deferred[Tuple[List[dns.RRHeader], None, None]]" = Deferred()
+        lookup_deferred: "Deferred[tuple[list[dns.RRHeader], None, None]]" = Deferred()
         dns_client_mock = Mock()
         dns_client_mock.lookupService.return_value = lookup_deferred
-        cache: Dict[bytes, List[Server]] = {}
+        cache: dict[bytes, list[Server]] = {}
         resolver = SrvResolver(dns_client=dns_client_mock, cache=cache)
 
         # Old versions of Twisted don't have an ensureDeferred in failureResultOf.
@@ -193,10 +193,10 @@ class SrvResolverTestCase(unittest.TestCase):
         """
         service_name = b"test_service.example.com"
 
-        lookup_deferred: "Deferred[Tuple[List[dns.RRHeader], None, None]]" = Deferred()
+        lookup_deferred: "Deferred[tuple[list[dns.RRHeader], None, None]]" = Deferred()
         dns_client_mock = Mock()
         dns_client_mock.lookupService.return_value = lookup_deferred
-        cache: Dict[bytes, List[Server]] = {}
+        cache: dict[bytes, list[Server]] = {}
         resolver = SrvResolver(dns_client=dns_client_mock, cache=cache)
 
         # Old versions of Twisted don't have an ensureDeferred in successResultOf.
diff --git a/tests/http/server/_base.py b/tests/http/server/_base.py
index 8eec4329fe..afa69d1b7b 100644
--- a/tests/http/server/_base.py
+++ b/tests/http/server/_base.py
@@ -26,14 +26,8 @@ from typing import (
     Any,
     Callable,
     ContextManager,
-    Dict,
     Generator,
-    List,
-    Optional,
-    Set,
-    Tuple,
     TypeVar,
-    Union,
 )
 from unittest import mock
 from unittest.mock import Mock
@@ -69,8 +63,8 @@ def test_disconnect(
     reactor: MemoryReactorClock,
     channel: FakeChannel,
     expect_cancellation: bool,
-    expected_body: Union[bytes, JsonDict],
-    expected_code: Optional[int] = None,
+    expected_body: bytes | JsonDict,
+    expected_code: int | None = None,
 ) -> None:
     """Disconnects an in-flight request and checks the response.
 
@@ -150,9 +144,9 @@ def make_request_with_cancellation_test(
     site: Site,
     method: str,
     path: str,
-    content: Union[bytes, str, JsonDict] = b"",
+    content: bytes | str | JsonDict = b"",
     *,
-    token: Optional[str] = None,
+    token: str | None = None,
 ) -> FakeChannel:
     """Performs a request repeatedly, disconnecting at successive `await`s, until
     one completes.
@@ -208,7 +202,7 @@ def make_request_with_cancellation_test(
 
     # The set of previously seen `await`s.
     # Each element is a stringified stack trace.
-    seen_awaits: Set[Tuple[str, ...]] = set()
+    seen_awaits: set[tuple[str, ...]] = set()
 
     _log_for_request(
         0, f"Running make_request_with_cancellation_test for {test_name}..."
@@ -337,7 +331,7 @@ class Deferred__await__Patch:
             deferred_patch.unblock_awaits()
     """
 
-    def __init__(self, seen_awaits: Set[Tuple[str, ...]], request_number: int):
+    def __init__(self, seen_awaits: set[tuple[str, ...]], request_number: int):
         """
         Args:
             seen_awaits: The set of stack traces of `await`s that have been previously
@@ -365,10 +359,10 @@ class Deferred__await__Patch:
         # unresolved `Deferred` and return it out of `Deferred.__await__` /
         # `coroutine.send()`. We have to resolve it later, in case the `await`ing
         # coroutine is part of some shared processing, such as `@cached`.
-        self._to_unblock: Dict[Deferred, Union[object, Failure]] = {}
+        self._to_unblock: dict[Deferred, object | Failure] = {}
 
         # The last stack we logged.
-        self._previous_stack: List[inspect.FrameInfo] = []
+        self._previous_stack: list[inspect.FrameInfo] = []
 
     def patch(self) -> ContextManager[Mock]:
         """Returns a context manager which patches `Deferred.__await__`."""
@@ -507,8 +501,8 @@ def _log_for_request(request_number: int, message: str) -> None:
 
 
 def _log_await_stack(
-    stack: List[inspect.FrameInfo],
-    previous_stack: List[inspect.FrameInfo],
+    stack: list[inspect.FrameInfo],
+    previous_stack: list[inspect.FrameInfo],
     request_number: int,
     note: str,
 ) -> None:
@@ -566,7 +560,7 @@ def _format_stack_frame(frame_info: inspect.FrameInfo) -> str:
     )
 
 
-def _get_stack(skip_frames: int) -> List[inspect.FrameInfo]:
+def _get_stack(skip_frames: int) -> list[inspect.FrameInfo]:
     """Captures the stack for a request.
 
     Skips any twisted frames and stops at `JsonResource.wrapped_async_request_handler`.
@@ -622,6 +616,6 @@ def _get_stack_frame_method_name(frame_info: inspect.FrameInfo) -> str:
     return method_name
 
 
-def _hash_stack(stack: List[inspect.FrameInfo]) -> Tuple[str, ...]:
+def _hash_stack(stack: list[inspect.FrameInfo]) -> tuple[str, ...]:
     """Turns a stack into a hashable value that can be put into a set."""
     return tuple(_format_stack_frame(frame) for frame in stack)
diff --git a/tests/http/test_client.py b/tests/http/test_client.py
index a02f6fc728..5c8c1220e4 100644
--- a/tests/http/test_client.py
+++ b/tests/http/test_client.py
@@ -20,7 +20,6 @@
 #
 
 from io import BytesIO
-from typing import Tuple, Union
 from unittest.mock import Mock
 
 from netaddr import IPSet
@@ -58,8 +57,8 @@ class ReadMultipartResponseTests(TestCase):
     redirect_data = b"\r\n\r\n--6067d4698f8d40a0a794ea7d7379d53a\r\nContent-Type: application/json\r\n\r\n{}\r\n--6067d4698f8d40a0a794ea7d7379d53a\r\nLocation: https://cdn.example.org/ab/c1/2345.txt\r\n\r\n--6067d4698f8d40a0a794ea7d7379d53a--\r\n\r\n"
 
     def _build_multipart_response(
-        self, response_length: Union[int, str], max_length: int
-    ) -> Tuple[
+        self, response_length: int | str, max_length: int
+    ) -> tuple[
         BytesIO,
         "Deferred[MultipartResponse]",
         _MultipartParserProtocol,
@@ -208,8 +207,8 @@ class ReadMultipartResponseTests(TestCase):
 
 class ReadBodyWithMaxSizeTests(TestCase):
     def _build_response(
-        self, length: Union[int, str] = UNKNOWN_LENGTH
-    ) -> Tuple[
+        self, length: int | str = UNKNOWN_LENGTH
+    ) -> tuple[
         BytesIO,
         "Deferred[int]",
         _DiscardBodyWithMaxSizeProtocol,
diff --git a/tests/http/test_matrixfederationclient.py b/tests/http/test_matrixfederationclient.py
index d06ea8c3ab..4792bdc9bc 100644
--- a/tests/http/test_matrixfederationclient.py
+++ b/tests/http/test_matrixfederationclient.py
@@ -18,7 +18,7 @@
 #
 #
 import io
-from typing import Any, Dict, Generator
+from typing import Any, Generator
 from unittest.mock import ANY, Mock, create_autospec
 
 from netaddr import IPSet
@@ -63,10 +63,6 @@ def check_logcontext(context: LoggingContextOrSentinel) -> None:
 
 
 class FederationClientTests(HomeserverTestCase):
-    def make_homeserver(self, reactor: MemoryReactor, clock: Clock) -> HomeServer:
-        hs = self.setup_test_homeserver(reactor=reactor, clock=clock)
-        return hs
-
     def prepare(
         self, reactor: MemoryReactor, clock: Clock, homeserver: HomeServer
     ) -> None:
@@ -418,6 +414,65 @@ class FederationClientTests(HomeserverTestCase):
         self.assertEqual(length, len(data))
         self.assertEqual(output_stream.getvalue(), data)
 
+    @override_config(
+        {
+            "federation": {
+                # Set the timeout to a deterministic value, in case the defaults
+                # change.
+                "client_timeout": "10s",
+            }
+        }
+    )
+    def test_authed_media_timeout_reading_body(self) -> None:
+        """
+        If the HTTP request is connected, but gets no response before being
+        timed out, it'll give a RequestSendFailed with can_retry.
+
+        Regression test for https://github.com/element-hq/synapse/issues/19061
+        """
+        limiter = Ratelimiter(
+            store=self.hs.get_datastores().main,
+            clock=self.clock,
+            cfg=RatelimitSettings(key="", per_second=0.17, burst_count=1048576),
+        )
+
+        output_stream = io.BytesIO()
+
+        d = defer.ensureDeferred(
+            # timeout is set by `client_timeout`, which we override above.
+            self.cl.federation_get_file(
+                "testserv:8008", "path", output_stream, limiter, "127.0.0.1", 10000
+            )
+        )
+
+        self.pump()
+
+        conn = Mock()
+        clients = self.reactor.tcpClients
+        client = clients[0][2].buildProtocol(None)
+        client.makeConnection(conn)
+
+        # Deferred does not have a result
+        self.assertNoResult(d)
+
+        # Send it the HTTP response
+        client.dataReceived(
+            b"HTTP/1.1 200 OK\r\n"
+            b"Server: Fake\r\n"
+            # Set a large content length, prompting the federation client to
+            # wait to receive the rest of the body.
+            b"Content-Length: 1000\r\n"
+            b"Content-Type: multipart/mixed; boundary=6067d4698f8d40a0a794ea7d7379d53a\r\n\r\n"
+        )
+
+        # Push by enough to time it out
+        self.reactor.advance(10.5)
+        f = self.failureResultOf(d)
+
+        self.assertIsInstance(f.value, RequestSendFailed)
+        self.assertTrue(f.value.can_retry)
+        self.assertIsInstance(f.value.inner_exception, defer.TimeoutError)
+
     @parameterized.expand(["get_json", "post_json", "delete_json", "put_json"])
     def test_timeout_reading_body(self, method_name: str) -> None:
         """
@@ -749,7 +804,7 @@ class FederationClientTests(HomeserverTestCase):
 
 
 class FederationClientProxyTests(BaseMultiWorkerStreamTestCase):
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         conf = super().default_config()
         conf["instance_map"] = {
             "main": {"host": "testserv", "port": 8765},
diff --git a/tests/http/test_proxy.py b/tests/http/test_proxy.py
index 7110dcf9f9..59a9b073bc 100644
--- a/tests/http/test_proxy.py
+++ b/tests/http/test_proxy.py
@@ -18,7 +18,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Set
 
 from parameterized import parameterized
 
@@ -64,7 +63,7 @@ class ProxyTests(TestCase):
     def test_parse_connection_header_value(
         self,
         connection_header_value: bytes,
-        expected_extra_headers_to_remove: Set[str],
+        expected_extra_headers_to_remove: set[str],
     ) -> None:
         """
         Tests that the connection header value is parsed correctly
diff --git a/tests/http/test_proxyagent.py b/tests/http/test_proxyagent.py
index 5bc5d18d81..c65115b3e5 100644
--- a/tests/http/test_proxyagent.py
+++ b/tests/http/test_proxyagent.py
@@ -21,7 +21,6 @@
 import base64
 import logging
 import os
-from typing import List, Optional
 from unittest.mock import patch
 
 import treq
@@ -195,7 +194,7 @@ class ProxyParserTests(TestCase):
         expected_scheme: bytes,
         expected_hostname: bytes,
         expected_port: int,
-        expected_credentials: Optional[bytes],
+        expected_credentials: bytes | None,
     ) -> None:
         """
         Tests that a given proxy URL will be broken into the components.
@@ -251,8 +250,8 @@ class ProxyAgentTests(TestCase):
         client_factory: IProtocolFactory,
         server_factory: IProtocolFactory,
         ssl: bool = False,
-        expected_sni: Optional[bytes] = None,
-        tls_sanlist: Optional[List[bytes]] = None,
+        expected_sni: bytes | None = None,
+        tls_sanlist: list[bytes] | None = None,
     ) -> IProtocol:
         """Builds a test server, and completes the outgoing client connection
 
@@ -602,7 +601,7 @@ class ProxyAgentTests(TestCase):
         self,
         proxy_config: ProxyConfig,
         expect_proxy_ssl: bool = False,
-        expected_auth_credentials: Optional[bytes] = None,
+        expected_auth_credentials: bytes | None = None,
     ) -> None:
         """Send a http request via an agent and check that it is correctly received at
             the proxy. The proxy can use either http or https.
@@ -682,7 +681,7 @@ class ProxyAgentTests(TestCase):
         self,
         proxy_config: ProxyConfig,
         expect_proxy_ssl: bool = False,
-        expected_auth_credentials: Optional[bytes] = None,
+        expected_auth_credentials: bytes | None = None,
     ) -> None:
         """Send a https request via an agent and check that it is correctly received at
             the proxy and client. The proxy can use either http or https.
diff --git a/tests/http/test_servlet.py b/tests/http/test_servlet.py
index db39ecf244..5bf8305d05 100644
--- a/tests/http/test_servlet.py
+++ b/tests/http/test_servlet.py
@@ -21,7 +21,6 @@
 import json
 from http import HTTPStatus
 from io import BytesIO
-from typing import Tuple, Union
 from unittest.mock import Mock
 
 from synapse.api.errors import Codes, SynapseError
@@ -40,7 +39,7 @@ from tests import unittest
 from tests.http.server._base import test_disconnect
 
 
-def make_request(content: Union[bytes, JsonDict]) -> Mock:
+def make_request(content: bytes | JsonDict) -> Mock:
     """Make an object that acts enough like a request."""
     request = Mock(spec=["method", "uri", "content"])
 
@@ -108,11 +107,11 @@ class CancellableRestServlet(RestServlet):
         self.clock = hs.get_clock()
 
     @cancellable
-    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await self.clock.sleep(1.0)
         return HTTPStatus.OK, {"result": True}
 
-    async def on_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def on_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await self.clock.sleep(1.0)
         return HTTPStatus.OK, {"result": True}
 
diff --git a/tests/logging/test_opentracing.py b/tests/logging/test_opentracing.py
index 057ca0db45..3aaa743265 100644
--- a/tests/logging/test_opentracing.py
+++ b/tests/logging/test_opentracing.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import Awaitable, Dict, cast
+from typing import Awaitable, cast
 
 from twisted.internet import defer
 from twisted.internet.testing import MemoryReactorClock
@@ -35,20 +35,25 @@ from synapse.logging.opentracing import (
     tag_args,
     trace_with_opname,
 )
+from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.util.clock import Clock
 
-try:
-    import opentracing
-    from opentracing.scope_managers.contextvars import ContextVarsScopeManager
-except ImportError:
-    opentracing = None  # type: ignore
-    ContextVarsScopeManager = None  # type: ignore
+from tests.server import get_clock
 
 try:
     import jaeger_client
 except ImportError:
     jaeger_client = None  # type: ignore
 
+
+try:
+    import opentracing
+
+    from synapse.logging.scopecontextmanager import LogContextScopeManager
+except ImportError:
+    opentracing = None  # type: ignore
+    LogContextScopeManager = None  # type: ignore
+
 import logging
 
 from tests.unittest import TestCase
@@ -56,7 +61,7 @@ from tests.unittest import TestCase
 logger = logging.getLogger(__name__)
 
 
-class TracingScopeTestCase(TestCase):
+class LogContextScopeManagerTestCase(TestCase):
     """
     Test that our tracing machinery works well in a variety of situations (especially
     with Twisted's runtime and deferreds).
@@ -67,7 +72,7 @@ class TracingScopeTestCase(TestCase):
     opentracing backend is Jaeger.
     """
 
-    if opentracing is None:
+    if opentracing is None or LogContextScopeManager is None:
         skip = "Requires opentracing"  # type: ignore[unreachable]
     if jaeger_client is None:
         skip = "Requires jaeger_client"  # type: ignore[unreachable]
@@ -77,9 +82,8 @@ class TracingScopeTestCase(TestCase):
         # global variables that power opentracing. We create our own tracer instance
         # and test with it.
 
-        scope_manager = ContextVarsScopeManager()
         config = jaeger_client.config.Config(
-            config={}, service_name="test", scope_manager=scope_manager
+            config={}, service_name="test", scope_manager=LogContextScopeManager()
         )
 
         self._reporter = jaeger_client.reporter.InMemoryReporter()
@@ -163,7 +167,9 @@ class TracingScopeTestCase(TestCase):
         # implements `ISynapseThreadlessReactor` (combination of the normal Twisted
         # Reactor/Clock interfaces), via inheritance from
         # `twisted.internet.testing.MemoryReactor` and `twisted.internet.testing.Clock`
-        clock = Clock(
+        # Ignore `multiple-internal-clocks` linter error here since we are creating a `Clock`
+        # for testing purposes.
+        clock = Clock(  # type: ignore[multiple-internal-clocks]
             reactor,  # type: ignore[arg-type]
             server_name="test_server",
         )
@@ -218,142 +224,6 @@ class TracingScopeTestCase(TestCase):
             [scopes[1].span, scopes[2].span, scopes[0].span],
         )
 
-    def test_run_in_background_active_scope_still_available(self) -> None:
-        """
-        Test that tasks running via `run_in_background` still have access to the
-        active tracing scope.
-
-        This is a regression test for a previous Synapse issue where the tracing scope
-        would `__exit__` and close before the `run_in_background` task completed and our
-        own previous custom `_LogContextScope.close(...)` would clear
-        `LoggingContext.scope` preventing further tracing spans from having the correct
-        parent.
-        """
-        reactor = MemoryReactorClock()
-        # type-ignore: mypy-zope doesn't seem to recognise that `MemoryReactorClock`
-        # implements `ISynapseThreadlessReactor` (combination of the normal Twisted
-        # Reactor/Clock interfaces), via inheritance from
-        # `twisted.internet.testing.MemoryReactor` and `twisted.internet.testing.Clock`
-        clock = Clock(
-            reactor,  # type: ignore[arg-type]
-            server_name="test_server",
-        )
-
-        scope_map: Dict[str, opentracing.Scope] = {}
-
-        async def async_task() -> None:
-            root_scope = scope_map["root"]
-            root_context = cast(jaeger_client.SpanContext, root_scope.span.context)
-
-            self.assertEqual(
-                self._tracer.active_span,
-                root_scope.span,
-                "expected to inherit the root tracing scope from where this was run",
-            )
-
-            # Return control back to the reactor thread and wait an arbitrary amount
-            await clock.sleep(4)
-
-            # This is a key part of what we're testing! In a previous version of
-            # Synapse, we would lose the active span at this point.
-            self.assertEqual(
-                self._tracer.active_span,
-                root_scope.span,
-                "expected to still have a root tracing scope/span active",
-            )
-
-            # For complete-ness sake, let's also trace more sub-tasks here and assert
-            # they have the correct span parents as well (root)
-
-            # Start tracing some other sub-task.
-            #
-            # This is a key part of what we're testing! In a previous version of
-            # Synapse, it would have the incorrect span parents.
-            scope = start_active_span(
-                "task1",
-                tracer=self._tracer,
-            )
-            scope_map["task1"] = scope
-
-            # Ensure the span parent is pointing to the root scope
-            context = cast(jaeger_client.SpanContext, scope.span.context)
-            self.assertEqual(
-                context.parent_id,
-                root_context.span_id,
-                "expected task1 parent to be the root span",
-            )
-
-            # Ensure that the active span is our new sub-task now
-            self.assertEqual(self._tracer.active_span, scope.span)
-            # Return control back to the reactor thread and wait an arbitrary amount
-            await clock.sleep(4)
-            # We should still see the active span as the scope wasn't closed yet
-            self.assertEqual(self._tracer.active_span, scope.span)
-            scope.close()
-
-        async def root() -> None:
-            with start_active_span(
-                "root span",
-                tracer=self._tracer,
-                # We will close this off later. We're basically just mimicking the same
-                # pattern for how we handle requests. We pass the span off to the
-                # request for it to finish.
-                finish_on_close=False,
-            ) as root_scope:
-                scope_map["root"] = root_scope
-                self.assertEqual(self._tracer.active_span, root_scope.span)
-
-                # Fire-and-forget a task
-                #
-                # XXX: The root scope context manager will `__exit__` before this task
-                # completes.
-                run_in_background(async_task)
-
-                # Because we used `run_in_background`, the active span should still be
-                # the root.
-                self.assertEqual(self._tracer.active_span, root_scope.span)
-
-            # We shouldn't see any active spans outside of the scope
-            self.assertIsNone(self._tracer.active_span)
-
-        with LoggingContext(name="root context", server_name="test_server"):
-            # Start the test off
-            d_root = defer.ensureDeferred(root())
-
-            # Let the tasks complete
-            reactor.pump((2,) * 8)
-            self.successResultOf(d_root)
-
-            # After we see all of the tasks are done (like a request when it
-            # `_finished_processing`), let's finish our root span
-            scope_map["root"].span.finish()
-
-            # Sanity check again: We shouldn't see any active spans leftover in this
-            # this context.
-            self.assertIsNone(self._tracer.active_span)
-
-        # The spans should be reported in order of their finishing: task 1, task 2,
-        # root.
-        #
-        # We use `assertIncludes` just as an easier way to see if items are missing or
-        # added. We assert the order just below
-        self.assertIncludes(
-            set(self._reporter.get_spans()),
-            {
-                scope_map["task1"].span,
-                scope_map["root"].span,
-            },
-            exact=True,
-        )
-        # This is where we actually assert the correct order
-        self.assertEqual(
-            self._reporter.get_spans(),
-            [
-                scope_map["task1"].span,
-                scope_map["root"].span,
-            ],
-        )
-
     def test_trace_decorator_sync(self) -> None:
         """
         Test whether we can use `@trace_with_opname` (`@trace`) and `@tag_args`
@@ -451,3 +321,203 @@ class TracingScopeTestCase(TestCase):
             [span.operation_name for span in self._reporter.get_spans()],
             ["fixture_awaitable_return_func"],
         )
+
+    async def test_run_as_background_process_standalone(self) -> None:
+        """
+        Test to make sure that the background process work starts its own trace.
+        """
+        reactor, clock = get_clock()
+
+        callback_finished = False
+        active_span_in_callback: jaeger_client.Span | None = None
+
+        async def bg_task() -> None:
+            nonlocal callback_finished, active_span_in_callback
+            try:
+                assert isinstance(self._tracer.active_span, jaeger_client.Span)
+                active_span_in_callback = self._tracer.active_span
+            finally:
+                # When exceptions happen, we still want to mark the callback as finished
+                # so that the test can complete and we see the underlying error.
+                callback_finished = True
+
+        # type-ignore: We ignore because the point is to test the bare function
+        run_as_background_process(  # type: ignore[untracked-background-process]
+            desc="some-bg-task",
+            server_name="test_server",
+            func=bg_task,
+            test_only_tracer=self._tracer,
+        )
+
+        # Now wait for the background process to finish
+        while not callback_finished:
+            await clock.sleep(0)
+
+        self.assertTrue(
+            callback_finished,
+            "Callback never finished which means the test probably didn't wait long enough",
+        )
+
+        self.assertEqual(
+            active_span_in_callback.operation_name if active_span_in_callback else None,
+            "bgproc.some-bg-task",
+            "expected a new span to be started for the background task",
+        )
+
+        # The spans should be reported in order of their finishing.
+        #
+        # We use `assertIncludes` just as an easier way to see if items are missing or
+        # added. We assert the order just below
+        actual_spans = [span.operation_name for span in self._reporter.get_spans()]
+        expected_spans = ["bgproc.some-bg-task"]
+        self.assertIncludes(
+            set(actual_spans),
+            set(expected_spans),
+            exact=True,
+        )
+        # This is where we actually assert the correct order
+        self.assertEqual(
+            actual_spans,
+            expected_spans,
+        )
+
+    async def test_run_as_background_process_cross_link(self) -> None:
+        """
+        Test to make sure that the background process work has its own trace and is
+        disconnected from any currently active trace (like a request). But we still have
+        cross-links between the two traces if there was already an active trace/span when
+        we kicked off the background process.
+        """
+        reactor, clock = get_clock()
+
+        callback_finished = False
+        active_span_in_callback: jaeger_client.Span | None = None
+
+        async def bg_task() -> None:
+            nonlocal callback_finished, active_span_in_callback
+            try:
+                assert isinstance(self._tracer.active_span, jaeger_client.Span)
+                active_span_in_callback = self._tracer.active_span
+            finally:
+                # When exceptions happen, we still want to mark the callback as finished
+                # so that the test can complete and we see the underlying error.
+                callback_finished = True
+
+        with LoggingContext(name="some-request", server_name="test_server"):
+            with start_active_span(
+                "some-request",
+                tracer=self._tracer,
+            ):
+                # type-ignore: We ignore because the point is to test the bare function
+                run_as_background_process(  # type: ignore[untracked-background-process]
+                    desc="some-bg-task",
+                    server_name="test_server",
+                    func=bg_task,
+                    test_only_tracer=self._tracer,
+                )
+
+        # Now wait for the background process to finish
+        while not callback_finished:
+            await clock.sleep(0)
+
+        self.assertTrue(
+            callback_finished,
+            "Callback never finished which means the test probably didn't wait long enough",
+        )
+
+        # We start `bgproc.some-bg-task` and `bgproc_child.some-bg-task` (see
+        # `run_as_background_process` implementation for why). Either is fine but for
+        # now we expect the child as its the innermost one that was started.
+        self.assertEqual(
+            active_span_in_callback.operation_name if active_span_in_callback else None,
+            "bgproc_child.some-bg-task",
+            "expected a new span to be started for the background task",
+        )
+
+        # The spans should be reported in order of their finishing.
+        #
+        # We use `assertIncludes` just as an easier way to see if items are missing or
+        # added. We assert the order just below
+        actual_spans = [span.operation_name for span in self._reporter.get_spans()]
+        expected_spans = [
+            "start_bgproc.some-bg-task",
+            "bgproc_child.some-bg-task",
+            "bgproc.some-bg-task",
+            "some-request",
+        ]
+        self.assertIncludes(
+            set(actual_spans),
+            set(expected_spans),
+            exact=True,
+        )
+        # This is where we actually assert the correct order
+        self.assertEqual(
+            actual_spans,
+            expected_spans,
+        )
+
+        span_map = {span.operation_name: span for span in self._reporter.get_spans()}
+        span_id_to_friendly_name = {
+            span.span_id: span.operation_name for span in self._reporter.get_spans()
+        }
+
+        def get_span_friendly_name(span_id: int | None) -> str:
+            if span_id is None:
+                return "None"
+
+            return span_id_to_friendly_name.get(span_id, f"unknown span {span_id}")
+
+        # Ensure the background process trace/span is disconnected from the request
+        # trace/span.
+        self.assertNotEqual(
+            get_span_friendly_name(span_map["bgproc.some-bg-task"].parent_id),
+            get_span_friendly_name(span_map["some-request"].span_id),
+        )
+
+        # We should see a cross-link in the request trace pointing to the background
+        # process trace.
+        #
+        # Make sure `start_bgproc.some-bg-task` is part of the request trace
+        self.assertEqual(
+            get_span_friendly_name(span_map["start_bgproc.some-bg-task"].parent_id),
+            get_span_friendly_name(span_map["some-request"].span_id),
+        )
+        # And has some references to the background process trace
+        self.assertIncludes(
+            {
+                f"{reference.type}:{get_span_friendly_name(reference.referenced_context.span_id)}"
+                if isinstance(reference.referenced_context, jaeger_client.SpanContext)
+                else f"{reference.type}:None"
+                for reference in (
+                    span_map["start_bgproc.some-bg-task"].references or []
+                )
+            },
+            {
+                f"follows_from:{get_span_friendly_name(span_map['bgproc.some-bg-task'].span_id)}"
+            },
+            exact=True,
+        )
+
+        # We should see a cross-link in the background process trace pointing to the
+        # request trace that kicked off the work.
+        #
+        # Make sure `start_bgproc.some-bg-task` is part of the request trace
+        self.assertEqual(
+            get_span_friendly_name(span_map["bgproc_child.some-bg-task"].parent_id),
+            get_span_friendly_name(span_map["bgproc.some-bg-task"].span_id),
+        )
+        # And has some references to the background process trace
+        self.assertIncludes(
+            {
+                f"{reference.type}:{get_span_friendly_name(reference.referenced_context.span_id)}"
+                if isinstance(reference.referenced_context, jaeger_client.SpanContext)
+                else f"{reference.type}:None"
+                for reference in (
+                    span_map["bgproc_child.some-bg-task"].references or []
+                )
+            },
+            {
+                f"follows_from:{get_span_friendly_name(span_map['some-request'].span_id)}"
+            },
+            exact=True,
+        )
diff --git a/tests/logging/test_remote_handler.py b/tests/logging/test_remote_handler.py
index e0fd12ccf7..534a1fc4ee 100644
--- a/tests/logging/test_remote_handler.py
+++ b/tests/logging/test_remote_handler.py
@@ -18,7 +18,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Tuple
 
 from twisted.internet.protocol import Protocol
 from twisted.internet.testing import AccumulatingProtocol, MemoryReactorClock
@@ -33,7 +32,7 @@ from tests.utils import checked_cast
 
 def connect_logging_client(
     reactor: MemoryReactorClock, client_id: int
-) -> Tuple[Protocol, AccumulatingProtocol]:
+) -> tuple[Protocol, AccumulatingProtocol]:
     # This is essentially tests.server.connect_client, but disabling autoflush on
     # the client transport. This is necessary to avoid an infinite loop due to
     # sending of data via the logging transport causing additional logs to be
diff --git a/tests/media/test_media_retention.py b/tests/media/test_media_retention.py
index aec1adb040..f27a9ed685 100644
--- a/tests/media/test_media_retention.py
+++ b/tests/media/test_media_retention.py
@@ -20,7 +20,7 @@
 #
 
 import io
-from typing import Iterable, Optional
+from typing import Iterable
 
 from matrix_common.types.mxc_uri import MXCUri
 
@@ -37,7 +37,6 @@ from synapse.util.stringutils import (
 
 from tests import unittest
 from tests.unittest import override_config
-from tests.utils import MockClock
 
 
 class MediaRetentionTestCase(unittest.HomeserverTestCase):
@@ -51,12 +50,6 @@ class MediaRetentionTestCase(unittest.HomeserverTestCase):
         admin.register_servlets_for_client_rest_resource,
     ]
 
-    def make_homeserver(self, reactor: MemoryReactor, clock: Clock) -> HomeServer:
-        # We need to be able to test advancing time in the homeserver, so we
-        # replace the test homeserver's default clock with a MockClock, which
-        # supports advancing time.
-        return self.setup_test_homeserver(clock=MockClock())
-
     def prepare(self, reactor: MemoryReactor, clock: Clock, hs: HomeServer) -> None:
         self.remote_server_name = "remote.homeserver"
         self.store = hs.get_datastores().main
@@ -70,9 +63,9 @@ class MediaRetentionTestCase(unittest.HomeserverTestCase):
         media_repository = hs.get_media_repository()
 
         def _create_media_and_set_attributes(
-            last_accessed_ms: Optional[int],
-            is_quarantined: Optional[bool] = False,
-            is_protected: Optional[bool] = False,
+            last_accessed_ms: int | None,
+            is_quarantined: bool | None = False,
+            is_protected: bool | None = False,
         ) -> MXCUri:
             # "Upload" some media to the local media store
             # If the meda
@@ -120,8 +113,8 @@ class MediaRetentionTestCase(unittest.HomeserverTestCase):
 
         def _cache_remote_media_and_set_attributes(
             media_id: str,
-            last_accessed_ms: Optional[int],
-            is_quarantined: Optional[bool] = False,
+            last_accessed_ms: int | None,
+            is_quarantined: bool | None = False,
         ) -> MXCUri:
             # Pretend to cache some remote media
             self.get_success(
diff --git a/tests/media/test_media_storage.py b/tests/media/test_media_storage.py
index 28c4ce676a..e56354e0b3 100644
--- a/tests/media/test_media_storage.py
+++ b/tests/media/test_media_storage.py
@@ -23,7 +23,7 @@ import shutil
 import tempfile
 from binascii import unhexlify
 from io import BytesIO
-from typing import Any, BinaryIO, ClassVar, Dict, List, Literal, Optional, Tuple, Union
+from typing import Any, BinaryIO, ClassVar, Literal
 from unittest.mock import MagicMock, Mock, patch
 from urllib import parse
 
@@ -150,8 +150,8 @@ class TestImage:
     data: bytes
     content_type: bytes
     extension: bytes
-    expected_cropped: Optional[bytes] = None
-    expected_scaled: Optional[bytes] = None
+    expected_cropped: bytes | None = None
+    expected_scaled: bytes | None = None
     expected_found: bool = True
     unable_to_thumbnail: bool = False
     is_inline: bool = True
@@ -297,12 +297,12 @@ class MediaRepoTests(unittest.HomeserverTestCase):
     user_id = "@test:user"
 
     def make_homeserver(self, reactor: MemoryReactor, clock: Clock) -> HomeServer:
-        self.fetches: List[
-            Tuple[
-                "Deferred[Tuple[bytes, Tuple[int, Dict[bytes, List[bytes]]]]]",
+        self.fetches: list[
+            tuple[
+                "Deferred[tuple[bytes, tuple[int, dict[bytes, list[bytes]]]]]",
                 str,
                 str,
-                Optional[QueryParams],
+                QueryParams | None,
             ]
         ] = []
 
@@ -313,16 +313,16 @@ class MediaRepoTests(unittest.HomeserverTestCase):
             download_ratelimiter: Ratelimiter,
             ip_address: Any,
             max_size: int,
-            args: Optional[QueryParams] = None,
+            args: QueryParams | None = None,
             retry_on_dns_fail: bool = True,
             ignore_backoff: bool = False,
             follow_redirects: bool = False,
-        ) -> "Deferred[Tuple[int, Dict[bytes, List[bytes]]]]":
+        ) -> "Deferred[tuple[int, dict[bytes, list[bytes]]]]":
             """A mock for MatrixFederationHttpClient.get_file."""
 
             def write_to(
-                r: Tuple[bytes, Tuple[int, Dict[bytes, List[bytes]]]],
-            ) -> Tuple[int, Dict[bytes, List[bytes]]]:
+                r: tuple[bytes, tuple[int, dict[bytes, list[bytes]]]],
+            ) -> tuple[int, dict[bytes, list[bytes]]]:
                 data, response = r
                 output_stream.write(data)
                 return response
@@ -332,7 +332,7 @@ class MediaRepoTests(unittest.HomeserverTestCase):
                 output_stream.write(f.value.response)
                 return f
 
-            d: Deferred[Tuple[bytes, Tuple[int, Dict[bytes, List[bytes]]]]] = Deferred()
+            d: Deferred[tuple[bytes, tuple[int, dict[bytes, list[bytes]]]]] = Deferred()
             self.fetches.append((d, destination, path, args))
             # Note that this callback changes the value held by d.
             d_after_callback = d.addCallbacks(write_to, write_err)
@@ -370,13 +370,13 @@ class MediaRepoTests(unittest.HomeserverTestCase):
 
         self.media_id = "example.com/12345"
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         resources = super().create_resource_dict()
         resources["/_matrix/media"] = self.hs.get_media_repository_resource()
         return resources
 
     def _req(
-        self, content_disposition: Optional[bytes], include_content_type: bool = True
+        self, content_disposition: bytes | None, include_content_type: bool = True
     ) -> FakeChannel:
         channel = self.make_request(
             "GET",
@@ -654,7 +654,7 @@ class MediaRepoTests(unittest.HomeserverTestCase):
     def _test_thumbnail(
         self,
         method: str,
-        expected_body: Optional[bytes],
+        expected_body: bytes | None,
         expected_found: bool,
         unable_to_thumbnail: bool = False,
     ) -> None:
@@ -860,15 +860,15 @@ class TestSpamCheckerLegacy:
     Uses the legacy Spam-Checker API.
     """
 
-    def __init__(self, config: Dict[str, Any], api: ModuleApi) -> None:
+    def __init__(self, config: dict[str, Any], api: ModuleApi) -> None:
         self.config = config
         self.api = api
 
     @staticmethod
-    def parse_config(config: Dict[str, Any]) -> Dict[str, Any]:
+    def parse_config(config: dict[str, Any]) -> dict[str, Any]:
         return config
 
-    async def check_event_for_spam(self, event: EventBase) -> Union[bool, str]:
+    async def check_event_for_spam(self, event: EventBase) -> bool | str:
         return False  # allow all events
 
     async def user_may_invite(
@@ -911,12 +911,12 @@ class SpamCheckerTestCaseLegacy(unittest.HomeserverTestCase):
 
         load_legacy_spam_checkers(hs)
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         resources = super().create_resource_dict()
         resources["/_matrix/media"] = self.hs.get_media_repository_resource()
         return resources
 
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         config = default_config("test")
 
         config.update(
@@ -965,14 +965,14 @@ class SpamCheckerTestCase(unittest.HomeserverTestCase):
             check_media_file_for_spam=self.check_media_file_for_spam
         )
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         resources = super().create_resource_dict()
         resources["/_matrix/media"] = self.hs.get_media_repository_resource()
         return resources
 
     async def check_media_file_for_spam(
         self, file_wrapper: ReadableFileWrapper, file_info: FileInfo
-    ) -> Union[Codes, Literal["NOT_SPAM"], Tuple[Codes, JsonDict]]:
+    ) -> Codes | Literal["NOT_SPAM"] | tuple[Codes, JsonDict]:
         buf = BytesIO()
         await file_wrapper.write_chunks_to(buf.write)
 
@@ -1028,7 +1028,7 @@ class RemoteDownloadLimiterTestCase(unittest.HomeserverTestCase):
         self.client = hs.get_federation_http_client()
         self.store = hs.get_datastores().main
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         # We need to manually set the resource tree to include media, the
         # default only does `/_matrix/client` APIs.
         return {"/_matrix/media": self.hs.get_media_repository_resource()}
@@ -1259,7 +1259,7 @@ class RemoteDownloadLimiterTestCase(unittest.HomeserverTestCase):
 
 
 def read_body(
-    response: IResponse, stream: ByteWriteable, max_size: Optional[int]
+    response: IResponse, stream: ByteWriteable, max_size: int | None
 ) -> Deferred:
     d: Deferred = defer.Deferred()
     stream.write(SMALL_PNG)
@@ -1280,7 +1280,7 @@ class MediaHashesTestCase(unittest.HomeserverTestCase):
         self.store = hs.get_datastores().main
         self.client = hs.get_federation_http_client()
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         resources = super().create_resource_dict()
         resources["/_matrix/media"] = self.hs.get_media_repository_resource()
         return resources
@@ -1377,7 +1377,7 @@ class MediaRepoSizeModuleCallbackTestCase(unittest.HomeserverTestCase):
             is_user_allowed_to_upload_media_of_size=self.is_user_allowed_to_upload_media_of_size,
         )
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         resources = super().create_resource_dict()
         resources["/_matrix/media"] = self.hs.get_media_repository_resource()
         return resources
diff --git a/tests/metrics/test_metrics.py b/tests/metrics/test_metrics.py
index 832e991730..084eba3a5a 100644
--- a/tests/metrics/test_metrics.py
+++ b/tests/metrics/test_metrics.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Dict, NoReturn, Protocol, Tuple
+from typing import NoReturn, Protocol
 
 from prometheus_client.core import Sample
 
@@ -35,7 +35,7 @@ from synapse.util.caches.deferred_cache import DeferredCache
 from tests import unittest
 
 
-def get_sample_labels_value(sample: Sample) -> Tuple[Dict[str, str], float]:
+def get_sample_labels_value(sample: Sample) -> tuple[dict[str, str], float]:
     """Extract the labels and values of a sample.
 
     prometheus_client 0.5 changed the sample type to a named tuple with more
@@ -54,7 +54,7 @@ def get_sample_labels_value(sample: Sample) -> Tuple[Dict[str, str], float]:
     # Otherwise fall back to treating it as a plain 3 tuple.
     else:
         # In older versions of prometheus_client Sample was a 3-tuple.
-        labels: Dict[str, str]
+        labels: dict[str, str]
         value: float
         _, labels, value = sample  # type: ignore[misc]
         return labels, value
@@ -127,7 +127,7 @@ class TestMauLimit(unittest.TestCase):
 
     def get_metrics_from_gauge(
         self, gauge: InFlightGauge
-    ) -> Dict[str, Dict[Tuple[str, ...], float]]:
+    ) -> dict[str, dict[tuple[str, ...], float]]:
         results = {}
 
         for r in gauge.collect():
@@ -164,7 +164,10 @@ class CacheMetricsTests(unittest.HomeserverTestCase):
         """
         CACHE_NAME = "cache_metrics_test_fgjkbdfg"
         cache: DeferredCache[str, str] = DeferredCache(
-            name=CACHE_NAME, server_name=self.hs.hostname, max_entries=777
+            name=CACHE_NAME,
+            clock=self.hs.get_clock(),
+            server_name=self.hs.hostname,
+            max_entries=777,
         )
 
         metrics_map = get_latest_metrics()
@@ -212,10 +215,10 @@ class CacheMetricsTests(unittest.HomeserverTestCase):
         """
         CACHE_NAME = "cache_metric_multiple_servers_test"
         cache1: DeferredCache[str, str] = DeferredCache(
-            name=CACHE_NAME, server_name="hs1", max_entries=777
+            name=CACHE_NAME, clock=self.clock, server_name="hs1", max_entries=777
         )
         cache2: DeferredCache[str, str] = DeferredCache(
-            name=CACHE_NAME, server_name="hs2", max_entries=777
+            name=CACHE_NAME, clock=self.clock, server_name="hs2", max_entries=777
         )
 
         metrics_map = get_latest_metrics()
@@ -381,7 +384,7 @@ class LaterGaugeTests(unittest.HomeserverTestCase):
         self.assertEqual(hs2_metric_value, "2.0")
 
 
-def get_latest_metrics() -> Dict[str, str]:
+def get_latest_metrics() -> dict[str, str]:
     """
     Collect the latest metrics from the registry and parse them into an easy to use map.
     The key includes the metric name and labels.
diff --git a/tests/module_api/test_api.py b/tests/module_api/test_api.py
index 86f987f292..12c8942bc8 100644
--- a/tests/module_api/test_api.py
+++ b/tests/module_api/test_api.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Any, Dict, Optional
+from typing import Any
 from unittest.mock import AsyncMock, Mock
 
 from twisted.internet import defer
@@ -803,10 +803,10 @@ class ModuleApiTestCase(BaseModuleApiTestCase):
         )
 
         # Setup a callback counting the number of pushers.
-        number_of_pushers_in_callback: Optional[int] = None
+        number_of_pushers_in_callback: int | None = None
 
         async def _on_logged_out_mock(
-            user_id: str, device_id: Optional[str], access_token: str
+            user_id: str, device_id: str | None, access_token: str
         ) -> None:
             nonlocal number_of_pushers_in_callback
             number_of_pushers_in_callback = len(
@@ -839,7 +839,7 @@ class ModuleApiWorkerTestCase(BaseModuleApiTestCase, BaseMultiWorkerStreamTestCa
         presence.register_servlets,
     ]
 
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         conf = super().default_config()
         conf["stream_writers"] = {"presence": ["presence_writer"]}
         conf["instance_map"] = {
diff --git a/tests/module_api/test_spamchecker.py b/tests/module_api/test_spamchecker.py
index d461d6cea2..42ef969ce0 100644
--- a/tests/module_api/test_spamchecker.py
+++ b/tests/module_api/test_spamchecker.py
@@ -12,7 +12,7 @@
 # <https://www.gnu.org/licenses/agpl-3.0.html>.
 #
 #
-from typing import Literal, Union
+from typing import Literal
 
 from twisted.internet.testing import MemoryReactor
 
@@ -59,7 +59,7 @@ class SpamCheckerTestCase(HomeserverTestCase):
 
         async def user_may_create_room(
             user_id: str, room_config: JsonDict
-        ) -> Union[Literal["NOT_SPAM"], Codes]:
+        ) -> Literal["NOT_SPAM"] | Codes:
             self.last_room_config = room_config
             self.last_user_id = user_id
             return "NOT_SPAM"
@@ -82,7 +82,7 @@ class SpamCheckerTestCase(HomeserverTestCase):
 
         async def user_may_create_room(
             user_id: str, room_config: JsonDict
-        ) -> Union[Literal["NOT_SPAM"], Codes]:
+        ) -> Literal["NOT_SPAM"] | Codes:
             self.last_room_config = room_config
             self.last_user_id = user_id
             return "NOT_SPAM"
@@ -117,7 +117,7 @@ class SpamCheckerTestCase(HomeserverTestCase):
 
         async def user_may_create_room(
             user_id: str, room_config: JsonDict
-        ) -> Union[Literal["NOT_SPAM"], Codes]:
+        ) -> Literal["NOT_SPAM"] | Codes:
             self.last_room_config = room_config
             self.last_user_id = user_id
             return "NOT_SPAM"
@@ -156,7 +156,7 @@ class SpamCheckerTestCase(HomeserverTestCase):
 
         async def user_may_create_room(
             user_id: str, room_config: JsonDict
-        ) -> Union[Literal["NOT_SPAM"], Codes]:
+        ) -> Literal["NOT_SPAM"] | Codes:
             self.last_room_config = room_config
             self.last_user_id = user_id
             return Codes.UNAUTHORIZED
@@ -181,7 +181,7 @@ class SpamCheckerTestCase(HomeserverTestCase):
 
         async def user_may_create_room(
             user_id: str,
-        ) -> Union[Literal["NOT_SPAM"], Codes]:
+        ) -> Literal["NOT_SPAM"] | Codes:
             self.last_user_id = user_id
             return "NOT_SPAM"
 
@@ -205,7 +205,7 @@ class SpamCheckerTestCase(HomeserverTestCase):
             event_type: str,
             state_key: str,
             content: JsonDict,
-        ) -> Union[Literal["NOT_SPAM"], Codes]:
+        ) -> Literal["NOT_SPAM"] | Codes:
             self.last_user_id = user_id
             self.last_room_id = room_id
             self.last_event_type = event_type
@@ -255,7 +255,7 @@ class SpamCheckerTestCase(HomeserverTestCase):
             event_type: str,
             state_key: str,
             content: JsonDict,
-        ) -> Union[Literal["NOT_SPAM"], Codes]:
+        ) -> Literal["NOT_SPAM"] | Codes:
             return Codes.FORBIDDEN
 
         self._module_api.register_spam_checker_callbacks(
diff --git a/tests/push/test_bulk_push_rule_evaluator.py b/tests/push/test_bulk_push_rule_evaluator.py
index 560d7234ec..137bbe24b2 100644
--- a/tests/push/test_bulk_push_rule_evaluator.py
+++ b/tests/push/test_bulk_push_rule_evaluator.py
@@ -20,7 +20,7 @@
 #
 
 from http import HTTPStatus
-from typing import Any, Optional
+from typing import Any
 from unittest.mock import AsyncMock, patch
 
 from parameterized import parameterized
@@ -210,7 +210,7 @@ class TestBulkPushRuleEvaluator(HomeserverTestCase):
     def _create_and_process(
         self,
         bulk_evaluator: BulkPushRuleEvaluator,
-        content: Optional[JsonDict] = None,
+        content: JsonDict | None = None,
         type: str = "test",
     ) -> bool:
         """Returns true iff the `mentions` trigger an event push action."""
diff --git a/tests/push/test_email.py b/tests/push/test_email.py
index 26819e2d3c..d3822b8643 100644
--- a/tests/push/test_email.py
+++ b/tests/push/test_email.py
@@ -21,7 +21,7 @@ import email.message
 import importlib.resources as importlib_resources
 import os
 from http import HTTPStatus
-from typing import Any, Dict, List, Sequence, Tuple
+from typing import Any, Sequence
 
 import attr
 from parameterized import parameterized
@@ -83,8 +83,8 @@ class EmailPusherTests(HomeserverTestCase):
 
         hs = self.setup_test_homeserver(config=config)
 
-        # List[Tuple[Deferred, args, kwargs]]
-        self.email_attempts: List[Tuple[Deferred, Sequence, Dict]] = []
+        # list[tuple[Deferred, args, kwargs]]
+        self.email_attempts: list[tuple[Deferred, Sequence, dict]] = []
 
         def sendmail(*args: Any, **kwargs: Any) -> Deferred:
             # This mocks out synapse.reactor.send_email._sendmail.
@@ -510,7 +510,7 @@ class EmailPusherTests(HomeserverTestCase):
         )
         self.assertEqual(len(pushers), 0)
 
-    def _check_for_mail(self) -> Tuple[Sequence, Dict]:
+    def _check_for_mail(self) -> tuple[Sequence, dict]:
         """
         Assert that synapse sent off exactly one email notification.
 
diff --git a/tests/push/test_http.py b/tests/push/test_http.py
index 4c8aae5782..ca2ced01ed 100644
--- a/tests/push/test_http.py
+++ b/tests/push/test_http.py
@@ -17,7 +17,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Any, Dict, List, Tuple
+from typing import Any
 from unittest.mock import Mock
 
 from parameterized import parameterized
@@ -51,7 +51,7 @@ class HTTPPusherTests(HomeserverTestCase):
     hijack_auth = False
 
     def make_homeserver(self, reactor: MemoryReactor, clock: Clock) -> HomeServer:
-        self.push_attempts: List[Tuple[Deferred, str, dict]] = []
+        self.push_attempts: list[tuple[Deferred, str, dict]] = []
 
         m = Mock()
 
@@ -747,7 +747,7 @@ class HTTPPusherTests(HomeserverTestCase):
 
     def _make_user_with_pusher(
         self, username: str, enabled: bool = True
-    ) -> Tuple[str, str]:
+    ) -> tuple[str, str]:
         """Registers a user and creates a pusher for them.
 
         Args:
@@ -925,7 +925,7 @@ class HTTPPusherTests(HomeserverTestCase):
         ret = self.get_success(
             self.hs.get_datastores().main.get_pushers_by({"user_name": user_id})
         )
-        pushers: List[PusherConfig] = list(ret)
+        pushers: list[PusherConfig] = list(ret)
 
         # Check that we still have one pusher, and that the device ID associated with
         # it didn't change.
@@ -1118,7 +1118,7 @@ class HTTPPusherTests(HomeserverTestCase):
         device_id = user_tuple.device_id
 
         # Set the push data dict based on test input parameters
-        push_data: Dict[str, Any] = {
+        push_data: dict[str, Any] = {
             "url": "http://example.com/_matrix/push/v1/notify",
         }
         if disable_badge_count:
diff --git a/tests/push/test_presentable_names.py b/tests/push/test_presentable_names.py
index bd42fc0580..2558f2c0b2 100644
--- a/tests/push/test_presentable_names.py
+++ b/tests/push/test_presentable_names.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import Iterable, List, Optional, Tuple, cast
+from typing import Iterable, cast
 
 from synapse.api.constants import EventTypes, Membership
 from synapse.api.room_versions import RoomVersions
@@ -36,7 +36,7 @@ class MockDataStore:
     (I.e. the state key is used as the event ID.)
     """
 
-    def __init__(self, events: Iterable[Tuple[StateKey, dict]]):
+    def __init__(self, events: Iterable[tuple[StateKey, dict]]):
         """
         Args:
             events: A state map to event contents.
@@ -59,11 +59,11 @@ class MockDataStore:
 
     async def get_event(
         self, event_id: str, allow_none: bool = False
-    ) -> Optional[FrozenEvent]:
+    ) -> FrozenEvent | None:
         assert allow_none, "Mock not configured for allow_none = False"
 
         # Decode the state key from the event ID.
-        state_key = cast(Tuple[str, str], tuple(event_id.split("|", 1)))
+        state_key = cast(tuple[str, str], tuple(event_id.split("|", 1)))
         return self._events.get(state_key)
 
     async def get_events(self, event_ids: Iterable[StateKey]) -> StateMap[EventBase]:
@@ -77,11 +77,11 @@ class PresentableNamesTestCase(unittest.HomeserverTestCase):
 
     def _calculate_room_name(
         self,
-        events: Iterable[Tuple[Tuple[str, str], dict]],
+        events: Iterable[tuple[tuple[str, str], dict]],
         user_id: str = "",
         fallback_to_members: bool = True,
         fallback_to_single_member: bool = True,
-    ) -> Optional[str]:
+    ) -> str | None:
         # Encode the state key into the event ID.
         room_state_ids = {k[0]: "|".join(k[0]) for k in events}
 
@@ -97,7 +97,7 @@ class PresentableNamesTestCase(unittest.HomeserverTestCase):
 
     def test_name(self) -> None:
         """A room name event should be used."""
-        events: List[Tuple[Tuple[str, str], dict]] = [
+        events: list[tuple[tuple[str, str], dict]] = [
             ((EventTypes.Name, ""), {"name": "test-name"}),
         ]
         self.assertEqual("test-name", self._calculate_room_name(events))
@@ -111,7 +111,7 @@ class PresentableNamesTestCase(unittest.HomeserverTestCase):
 
     def test_canonical_alias(self) -> None:
         """An canonical alias should be used."""
-        events: List[Tuple[Tuple[str, str], dict]] = [
+        events: list[tuple[tuple[str, str], dict]] = [
             ((EventTypes.CanonicalAlias, ""), {"alias": "#test-name:test"}),
         ]
         self.assertEqual("#test-name:test", self._calculate_room_name(events))
@@ -125,7 +125,7 @@ class PresentableNamesTestCase(unittest.HomeserverTestCase):
 
     def test_invite(self) -> None:
         """An invite has special behaviour."""
-        events: List[Tuple[Tuple[str, str], dict]] = [
+        events: list[tuple[tuple[str, str], dict]] = [
             ((EventTypes.Member, self.USER_ID), {"membership": Membership.INVITE}),
             ((EventTypes.Member, self.OTHER_USER_ID), {"displayname": "Other User"}),
         ]
@@ -151,7 +151,7 @@ class PresentableNamesTestCase(unittest.HomeserverTestCase):
 
     def test_no_members(self) -> None:
         """Behaviour of an empty room."""
-        events: List[Tuple[Tuple[str, str], dict]] = []
+        events: list[tuple[tuple[str, str], dict]] = []
         self.assertEqual("Empty Room", self._calculate_room_name(events))
 
         # Note that events with invalid (or missing) membership are ignored.
diff --git a/tests/push/test_push_rule_evaluator.py b/tests/push/test_push_rule_evaluator.py
index 718c9614e5..a786d74bf1 100644
--- a/tests/push/test_push_rule_evaluator.py
+++ b/tests/push/test_push_rule_evaluator.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import Any, Dict, List, Optional, Union, cast
+from typing import Any, cast
 
 from twisted.internet.testing import MemoryReactor
 
@@ -60,7 +60,7 @@ class FlattenDictTestCase(unittest.TestCase):
 
     def test_non_string(self) -> None:
         """String, booleans, ints, nulls and list of those should be kept while other items are dropped."""
-        input: Dict[str, Any] = {
+        input: dict[str, Any] = {
             "woo": "woo",
             "foo": True,
             "bar": 1,
@@ -148,7 +148,7 @@ class PushRuleEvaluatorTestCase(unittest.TestCase):
         self,
         content: JsonMapping,
         *,
-        related_events: Optional[JsonDict] = None,
+        related_events: JsonDict | None = None,
         msc4210: bool = False,
         msc4306: bool = False,
     ) -> PushRuleEvaluator:
@@ -165,13 +165,13 @@ class PushRuleEvaluatorTestCase(unittest.TestCase):
         )
         room_member_count = 0
         sender_power_level = 0
-        power_levels: Dict[str, Union[int, Dict[str, int]]] = {}
+        power_levels: dict[str, int | dict[str, int]] = {}
         return PushRuleEvaluator(
             _flatten_dict(event),
             False,
             room_member_count,
             sender_power_level,
-            cast(Dict[str, int], power_levels.get("notifications", {})),
+            cast(dict[str, int], power_levels.get("notifications", {})),
             {} if related_events is None else related_events,
             related_event_match_enabled=True,
             room_version_feature_flags=event.room_version.msc3931_push_features,
@@ -205,13 +205,13 @@ class PushRuleEvaluatorTestCase(unittest.TestCase):
         self.assertTrue(evaluator.matches(condition, "@user:test", "foo bar"))
 
     def _assert_matches(
-        self, condition: JsonDict, content: JsonMapping, msg: Optional[str] = None
+        self, condition: JsonDict, content: JsonMapping, msg: str | None = None
     ) -> None:
         evaluator = self._get_evaluator(content)
         self.assertTrue(evaluator.matches(condition, "@user:test", "display_name"), msg)
 
     def _assert_not_matches(
-        self, condition: JsonDict, content: JsonDict, msg: Optional[str] = None
+        self, condition: JsonDict, content: JsonDict, msg: str | None = None
     ) -> None:
         evaluator = self._get_evaluator(content)
         self.assertFalse(
@@ -588,7 +588,7 @@ class PushRuleEvaluatorTestCase(unittest.TestCase):
         This tests the behaviour of tweaks_for_actions.
         """
 
-        actions: List[Union[Dict[str, str], str]] = [
+        actions: list[dict[str, str] | str] = [
             {"set_tweak": "sound", "value": "default"},
             {"set_tweak": "highlight"},
             "notify",
diff --git a/tests/replication/_base.py b/tests/replication/_base.py
index 36d3213908..b23696668f 100644
--- a/tests/replication/_base.py
+++ b/tests/replication/_base.py
@@ -19,7 +19,7 @@
 #
 import logging
 from collections import defaultdict
-from typing import Any, Dict, List, Optional, Set, Tuple
+from typing import Any
 
 from twisted.internet.address import IPv4Address
 from twisted.internet.protocol import Protocol, connectionDone
@@ -105,10 +105,10 @@ class BaseStreamTestCase(unittest.HomeserverTestCase):
             repl_handler,
         )
 
-        self._client_transport: Optional[FakeTransport] = None
-        self._server_transport: Optional[FakeTransport] = None
+        self._client_transport: FakeTransport | None = None
+        self._server_transport: FakeTransport | None = None
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         d = super().create_resource_dict()
         d["/_synapse/replication"] = ReplicationRestResource(self.hs)
         return d
@@ -173,11 +173,17 @@ class BaseStreamTestCase(unittest.HomeserverTestCase):
 
         # Set up the server side protocol
         server_address = IPv4Address("TCP", host, port)
-        channel = self.site.buildProtocol((host, port))
+        # The type ignore is here because mypy doesn't think the host/port tuple is of
+        # the correct type, even though it is the exact example given for
+        # `twisted.internet.interfaces.IAddress`.
+        # Mypy was happy with the type before we overrode `buildProtocol` in
+        # `SynapseSite`, probably because there was enough inheritance indirection before
+        # withe the argument not having a type associated with it.
+        channel = self.site.buildProtocol((host, port))  # type: ignore[arg-type]
 
         # hook into the channel's request factory so that we can keep a record
         # of the requests
-        requests: List[SynapseRequest] = []
+        requests: list[SynapseRequest] = []
         real_request_factory = channel.requestFactory
 
         def request_factory(*args: Any, **kwargs: Any) -> SynapseRequest:
@@ -185,7 +191,7 @@ class BaseStreamTestCase(unittest.HomeserverTestCase):
             requests.append(request)
             return request
 
-        channel.requestFactory = request_factory
+        channel.requestFactory = request_factory  # type: ignore[method-assign]
 
         # Connect client to server and vice versa.
         client_to_server_transport = FakeTransport(
@@ -208,7 +214,12 @@ class BaseStreamTestCase(unittest.HomeserverTestCase):
         client_to_server_transport.loseConnection()
 
         # there should have been exactly one request
-        self.assertEqual(len(requests), 1)
+        self.assertEqual(
+            len(requests),
+            1,
+            "Expected to handle exactly one HTTP replication request but saw %d - requests=%s"
+            % (len(requests), requests),
+        )
 
         return requests[0]
 
@@ -245,7 +256,7 @@ class BaseMultiWorkerStreamTestCase(unittest.HomeserverTestCase):
         # Redis replication only takes place on Postgres
         skip = "Requires Postgres"
 
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         """
         Overrides the default config to enable Redis.
         Even if the test only uses make_worker_hs, the main process needs Redis
@@ -314,7 +325,7 @@ class BaseMultiWorkerStreamTestCase(unittest.HomeserverTestCase):
         return resource
 
     def make_worker_hs(
-        self, worker_app: str, extra_config: Optional[dict] = None, **kwargs: Any
+        self, worker_app: str, extra_config: dict | None = None, **kwargs: Any
     ) -> HomeServer:
         """Make a new worker HS instance, correctly connecting replication
         stream to the master HS.
@@ -427,7 +438,7 @@ class BaseMultiWorkerStreamTestCase(unittest.HomeserverTestCase):
 
         # Set up the server side protocol
         server_address = IPv4Address("TCP", host, port)
-        channel = self._hs_to_site[hs].buildProtocol((host, port))
+        channel = self._hs_to_site[hs].buildProtocol((host, port))  # type: ignore[arg-type]
 
         # Connect client to server and vice versa.
         client_to_server_transport = FakeTransport(
@@ -480,7 +491,7 @@ class TestReplicationDataHandler(ReplicationDataHandler):
         super().__init__(hs)
 
         # list of received (stream_name, token, row) tuples
-        self.received_rdata_rows: List[Tuple[str, int, Any]] = []
+        self.received_rdata_rows: list[tuple[str, int, Any]] = []
 
     async def on_rdata(
         self, stream_name: str, instance_name: str, token: int, rows: list
@@ -494,7 +505,7 @@ class FakeRedisPubSubServer:
     """A fake Redis server for pub/sub."""
 
     def __init__(self) -> None:
-        self._subscribers_by_channel: Dict[bytes, Set["FakeRedisPubSubProtocol"]] = (
+        self._subscribers_by_channel: dict[bytes, set["FakeRedisPubSubProtocol"]] = (
             defaultdict(set)
         )
 
@@ -523,7 +534,7 @@ class FakeRedisPubSubServer:
 class FakeRedisPubSubProtocol(Protocol):
     """A connection from a client talking to the fake Redis server."""
 
-    transport: Optional[FakeTransport] = None
+    transport: FakeTransport | None = None
 
     def __init__(self, server: FakeRedisPubSubServer):
         self._server = server
diff --git a/tests/replication/http/test__base.py b/tests/replication/http/test__base.py
index 31d3163c01..b757c6428a 100644
--- a/tests/replication/http/test__base.py
+++ b/tests/replication/http/test__base.py
@@ -20,7 +20,6 @@
 #
 
 from http import HTTPStatus
-from typing import Tuple
 
 from twisted.web.server import Request
 
@@ -52,7 +51,7 @@ class CancellableReplicationEndpoint(ReplicationEndpoint):
     @cancellable
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await self.clock.sleep(1.0)
         return HTTPStatus.OK, {"result": True}
 
@@ -73,7 +72,7 @@ class UncancellableReplicationEndpoint(ReplicationEndpoint):
 
     async def _handle_request(  # type: ignore[override]
         self, request: Request, content: JsonDict
-    ) -> Tuple[int, JsonDict]:
+    ) -> tuple[int, JsonDict]:
         await self.clock.sleep(1.0)
         return HTTPStatus.OK, {"result": True}
 
diff --git a/tests/replication/storage/_base.py b/tests/replication/storage/_base.py
index fb99cb2335..7b757e9e9e 100644
--- a/tests/replication/storage/_base.py
+++ b/tests/replication/storage/_base.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import Any, Callable, Iterable, Optional
+from typing import Any, Callable, Iterable
 from unittest.mock import Mock
 
 from twisted.internet.testing import MemoryReactor
@@ -56,8 +56,8 @@ class BaseWorkerStoreTestCase(BaseStreamTestCase):
         self,
         method: str,
         args: Iterable[Any],
-        expected_result: Optional[Any] = None,
-        asserter: Optional[Callable[[Any, Any, Optional[Any]], None]] = None,
+        expected_result: Any | None = None,
+        asserter: Callable[[Any, Any, Any | None], None] | None = None,
     ) -> None:
         if asserter is None:
             asserter = self.assertEqual
diff --git a/tests/replication/storage/test_events.py b/tests/replication/storage/test_events.py
index fce3269005..28bfb8b8ea 100644
--- a/tests/replication/storage/test_events.py
+++ b/tests/replication/storage/test_events.py
@@ -19,7 +19,7 @@
 #
 #
 import logging
-from typing import Any, Iterable, List, Optional, Tuple
+from typing import Any, Iterable
 
 from canonicaljson import encode_canonical_json
 from parameterized import parameterized
@@ -66,7 +66,7 @@ class EventsWorkerStoreTestCase(BaseWorkerStoreTestCase):
         )
 
     def assertEventsEqual(
-        self, first: EventBase, second: EventBase, msg: Optional[Any] = None
+        self, first: EventBase, second: EventBase, msg: Any | None = None
     ) -> None:
         self.assertEqual(
             encode_canonical_json(first.get_pdu_json()),
@@ -241,16 +241,16 @@ class EventsWorkerStoreTestCase(BaseWorkerStoreTestCase):
         sender: str = USER_ID,
         room_id: str = ROOM_ID,
         type: str = "m.room.message",
-        key: Optional[str] = None,
-        internal: Optional[dict] = None,
-        depth: Optional[int] = None,
-        prev_events: Optional[List[Tuple[str, dict]]] = None,
-        auth_events: Optional[List[str]] = None,
-        prev_state: Optional[List[str]] = None,
-        redacts: Optional[str] = None,
+        key: str | None = None,
+        internal: dict | None = None,
+        depth: int | None = None,
+        prev_events: list[tuple[str, dict]] | None = None,
+        auth_events: list[str] | None = None,
+        prev_state: list[str] | None = None,
+        redacts: str | None = None,
         push_actions: Iterable = frozenset(),
         **content: object,
-    ) -> Tuple[EventBase, EventContext]:
+    ) -> tuple[EventBase, EventContext]:
         prev_events = prev_events or []
         auth_events = auth_events or []
         prev_state = prev_state or []
diff --git a/tests/replication/tcp/streams/test_account_data.py b/tests/replication/tcp/streams/test_account_data.py
index 6dea29ae15..d0c189230c 100644
--- a/tests/replication/tcp/streams/test_account_data.py
+++ b/tests/replication/tcp/streams/test_account_data.py
@@ -46,28 +46,39 @@ class AccountDataStreamTestCase(BaseStreamTestCase):
 
         # check we're testing what we think we are: no rows should yet have been
         # received
-        self.assertEqual([], self.test_handler.received_rdata_rows)
+        received_account_data_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == AccountDataStream.NAME
+        ]
+        self.assertEqual([], received_account_data_rows)
 
         # now reconnect to pull the updates
         self.reconnect()
         self.replicate()
 
-        # we should have received all the expected rows in the right order
-        received_rows = self.test_handler.received_rdata_rows
+        # We should have received all the expected rows in the right order
+        #
+        # Filter the updates to only include account data changes
+        received_account_data_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == AccountDataStream.NAME
+        ]
 
         for t in updates:
-            (stream_name, token, row) = received_rows.pop(0)
+            (stream_name, token, row) = received_account_data_rows.pop(0)
             self.assertEqual(stream_name, AccountDataStream.NAME)
             self.assertIsInstance(row, AccountDataStream.AccountDataStreamRow)
             self.assertEqual(row.data_type, t)
             self.assertEqual(row.room_id, "test_room")
 
-        (stream_name, token, row) = received_rows.pop(0)
+        (stream_name, token, row) = received_account_data_rows.pop(0)
         self.assertIsInstance(row, AccountDataStream.AccountDataStreamRow)
         self.assertEqual(row.data_type, "m.global")
         self.assertIsNone(row.room_id)
 
-        self.assertEqual([], received_rows)
+        self.assertEqual([], received_account_data_rows)
 
     def test_update_function_global_account_data_limit(self) -> None:
         """Test replication with many global account data updates"""
@@ -85,32 +96,38 @@ class AccountDataStreamTestCase(BaseStreamTestCase):
             store.add_account_data_to_room("test_user", "test_room", "m.per_room", {})
         )
 
-        # tell the notifier to catch up to avoid duplicate rows.
-        # workaround for https://github.com/matrix-org/synapse/issues/7360
-        # FIXME remove this when the above is fixed
-        self.replicate()
-
         # check we're testing what we think we are: no rows should yet have been
         # received
-        self.assertEqual([], self.test_handler.received_rdata_rows)
+        received_account_data_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == AccountDataStream.NAME
+        ]
+        self.assertEqual([], received_account_data_rows)
 
         # now reconnect to pull the updates
         self.reconnect()
         self.replicate()
 
         # we should have received all the expected rows in the right order
-        received_rows = self.test_handler.received_rdata_rows
+        #
+        # Filter the updates to only include typing changes
+        received_account_data_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == AccountDataStream.NAME
+        ]
 
         for t in updates:
-            (stream_name, token, row) = received_rows.pop(0)
+            (stream_name, token, row) = received_account_data_rows.pop(0)
             self.assertEqual(stream_name, AccountDataStream.NAME)
             self.assertIsInstance(row, AccountDataStream.AccountDataStreamRow)
             self.assertEqual(row.data_type, t)
             self.assertIsNone(row.room_id)
 
-        (stream_name, token, row) = received_rows.pop(0)
+        (stream_name, token, row) = received_account_data_rows.pop(0)
         self.assertIsInstance(row, AccountDataStream.AccountDataStreamRow)
         self.assertEqual(row.data_type, "m.per_room")
         self.assertEqual(row.room_id, "test_room")
 
-        self.assertEqual([], received_rows)
+        self.assertEqual([], received_account_data_rows)
diff --git a/tests/replication/tcp/streams/test_events.py b/tests/replication/tcp/streams/test_events.py
index 782dad39f5..484fd6b6db 100644
--- a/tests/replication/tcp/streams/test_events.py
+++ b/tests/replication/tcp/streams/test_events.py
@@ -18,7 +18,7 @@
 #
 #
 
-from typing import Any, List, Optional
+from typing import Any
 
 from parameterized import parameterized
 
@@ -30,6 +30,7 @@ from synapse.replication.tcp.commands import RdataCommand
 from synapse.replication.tcp.streams._base import _STREAM_UPDATE_TARGET_ROW_COUNT
 from synapse.replication.tcp.streams.events import (
     _MAX_STATE_UPDATES_PER_ROOM,
+    EventsStream,
     EventsStreamAllStateRow,
     EventsStreamCurrentStateRow,
     EventsStreamEventRow,
@@ -82,7 +83,12 @@ class EventsStreamTestCase(BaseStreamTestCase):
 
         # check we're testing what we think we are: no rows should yet have been
         # received
-        self.assertEqual([], self.test_handler.received_rdata_rows)
+        received_event_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == EventsStream.NAME
+        ]
+        self.assertEqual([], received_event_rows)
 
         # now reconnect to pull the updates
         self.reconnect()
@@ -90,31 +96,34 @@ class EventsStreamTestCase(BaseStreamTestCase):
 
         # we should have received all the expected rows in the right order (as
         # well as various cache invalidation updates which we ignore)
-        received_rows = [
-            row for row in self.test_handler.received_rdata_rows if row[0] == "events"
+        #
+        # Filter the updates to only include event changes
+        received_event_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == EventsStream.NAME
         ]
-
         for event in events:
-            stream_name, token, row = received_rows.pop(0)
-            self.assertEqual("events", stream_name)
+            stream_name, token, row = received_event_rows.pop(0)
+            self.assertEqual(EventsStream.NAME, stream_name)
             self.assertIsInstance(row, EventsStreamRow)
             self.assertEqual(row.type, "ev")
             self.assertIsInstance(row.data, EventsStreamEventRow)
             self.assertEqual(row.data.event_id, event.event_id)
 
-        stream_name, token, row = received_rows.pop(0)
+        stream_name, token, row = received_event_rows.pop(0)
         self.assertIsInstance(row, EventsStreamRow)
         self.assertIsInstance(row.data, EventsStreamEventRow)
         self.assertEqual(row.data.event_id, state_event.event_id)
 
-        stream_name, token, row = received_rows.pop(0)
+        stream_name, token, row = received_event_rows.pop(0)
         self.assertEqual("events", stream_name)
         self.assertIsInstance(row, EventsStreamRow)
         self.assertEqual(row.type, "state")
         self.assertIsInstance(row.data, EventsStreamCurrentStateRow)
         self.assertEqual(row.data.event_id, state_event.event_id)
 
-        self.assertEqual([], received_rows)
+        self.assertEqual([], received_event_rows)
 
     @parameterized.expand(
         [(_STREAM_UPDATE_TARGET_ROW_COUNT, False), (_MAX_STATE_UPDATES_PER_ROOM, True)]
@@ -170,9 +179,12 @@ class EventsStreamTestCase(BaseStreamTestCase):
 
         self.replicate()
         # all those events and state changes should have landed
-        self.assertGreaterEqual(
-            len(self.test_handler.received_rdata_rows), 2 * len(events)
-        )
+        received_event_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == EventsStream.NAME
+        ]
+        self.assertGreaterEqual(len(received_event_rows), 2 * len(events))
 
         # disconnect, so that we can stack up the changes
         self.disconnect()
@@ -202,7 +214,12 @@ class EventsStreamTestCase(BaseStreamTestCase):
 
         # check we're testing what we think we are: no rows should yet have been
         # received
-        self.assertEqual([], self.test_handler.received_rdata_rows)
+        received_event_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == EventsStream.NAME
+        ]
+        self.assertEqual([], received_event_rows)
 
         # now reconnect to pull the updates
         self.reconnect()
@@ -218,33 +235,34 @@ class EventsStreamTestCase(BaseStreamTestCase):
         #       of the states that got reverted.
         # - two rows for state2
 
-        received_rows = [
-            row for row in self.test_handler.received_rdata_rows if row[0] == "events"
+        received_event_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == EventsStream.NAME
         ]
-
         # first check the first two rows, which should be the state1 event.
-        stream_name, token, row = received_rows.pop(0)
+        stream_name, token, row = received_event_rows.pop(0)
         self.assertEqual("events", stream_name)
         self.assertIsInstance(row, EventsStreamRow)
         self.assertEqual(row.type, "ev")
         self.assertIsInstance(row.data, EventsStreamEventRow)
         self.assertEqual(row.data.event_id, state1.event_id)
 
-        stream_name, token, row = received_rows.pop(0)
+        stream_name, token, row = received_event_rows.pop(0)
         self.assertIsInstance(row, EventsStreamRow)
         self.assertEqual(row.type, "state")
         self.assertIsInstance(row.data, EventsStreamCurrentStateRow)
         self.assertEqual(row.data.event_id, state1.event_id)
 
         # now the last two rows, which should be the state2 event.
-        stream_name, token, row = received_rows.pop(-2)
+        stream_name, token, row = received_event_rows.pop(-2)
         self.assertEqual("events", stream_name)
         self.assertIsInstance(row, EventsStreamRow)
         self.assertEqual(row.type, "ev")
         self.assertIsInstance(row.data, EventsStreamEventRow)
         self.assertEqual(row.data.event_id, state2.event_id)
 
-        stream_name, token, row = received_rows.pop(-1)
+        stream_name, token, row = received_event_rows.pop(-1)
         self.assertIsInstance(row, EventsStreamRow)
         self.assertEqual(row.type, "state")
         self.assertIsInstance(row.data, EventsStreamCurrentStateRow)
@@ -254,16 +272,16 @@ class EventsStreamTestCase(BaseStreamTestCase):
         if collapse_state_changes:
             # that should leave us with the rows for the PL event, the state changes
             # get collapsed into a single row.
-            self.assertEqual(len(received_rows), 2)
+            self.assertEqual(len(received_event_rows), 2)
 
-            stream_name, token, row = received_rows.pop(0)
+            stream_name, token, row = received_event_rows.pop(0)
             self.assertEqual("events", stream_name)
             self.assertIsInstance(row, EventsStreamRow)
             self.assertEqual(row.type, "ev")
             self.assertIsInstance(row.data, EventsStreamEventRow)
             self.assertEqual(row.data.event_id, pl_event.event_id)
 
-            stream_name, token, row = received_rows.pop(0)
+            stream_name, token, row = received_event_rows.pop(0)
             self.assertIsInstance(row, EventsStreamRow)
             self.assertEqual(row.type, "state-all")
             self.assertIsInstance(row.data, EventsStreamAllStateRow)
@@ -271,9 +289,9 @@ class EventsStreamTestCase(BaseStreamTestCase):
 
         else:
             # that should leave us with the rows for the PL event
-            self.assertEqual(len(received_rows), len(events) + 2)
+            self.assertEqual(len(received_event_rows), len(events) + 2)
 
-            stream_name, token, row = received_rows.pop(0)
+            stream_name, token, row = received_event_rows.pop(0)
             self.assertEqual("events", stream_name)
             self.assertIsInstance(row, EventsStreamRow)
             self.assertEqual(row.type, "ev")
@@ -281,8 +299,8 @@ class EventsStreamTestCase(BaseStreamTestCase):
             self.assertEqual(row.data.event_id, pl_event.event_id)
 
             # the state rows are unsorted
-            state_rows: List[EventsStreamCurrentStateRow] = []
-            for stream_name, _, row in received_rows:
+            state_rows: list[EventsStreamCurrentStateRow] = []
+            for stream_name, _, row in received_event_rows:
                 self.assertEqual("events", stream_name)
                 self.assertIsInstance(row, EventsStreamRow)
                 self.assertEqual(row.type, "state")
@@ -337,7 +355,7 @@ class EventsStreamTestCase(BaseStreamTestCase):
             self.hs.get_datastores().main.get_latest_event_ids_in_room(self.room_id)
         )
 
-        events: List[EventBase] = []
+        events: list[EventBase] = []
         for user in user_ids:
             events.extend(
                 self._inject_state_event(sender=user) for _ in range(STATES_PER_USER)
@@ -346,9 +364,12 @@ class EventsStreamTestCase(BaseStreamTestCase):
         self.replicate()
 
         # all those events and state changes should have landed
-        self.assertGreaterEqual(
-            len(self.test_handler.received_rdata_rows), 2 * len(events)
-        )
+        received_event_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == EventsStream.NAME
+        ]
+        self.assertGreaterEqual(len(received_event_rows), 2 * len(events))
 
         # disconnect, so that we can stack up the changes
         self.disconnect()
@@ -375,7 +396,12 @@ class EventsStreamTestCase(BaseStreamTestCase):
 
         # check we're testing what we think we are: no rows should yet have been
         # received
-        self.assertEqual([], self.test_handler.received_rdata_rows)
+        received_event_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == EventsStream.NAME
+        ]
+        self.assertEqual([], received_event_rows)
 
         # now reconnect to pull the updates
         self.reconnect()
@@ -383,14 +409,16 @@ class EventsStreamTestCase(BaseStreamTestCase):
 
         # we should have received all the expected rows in the right order (as
         # well as various cache invalidation updates which we ignore)
-        received_rows = [
-            row for row in self.test_handler.received_rdata_rows if row[0] == "events"
+        received_event_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == EventsStream.NAME
         ]
-        self.assertGreaterEqual(len(received_rows), len(events))
+        self.assertGreaterEqual(len(received_event_rows), len(events))
         for i in range(NUM_USERS):
             # for each user, we expect the PL event row, followed by state rows for
             # the PL event and each of the states that got reverted.
-            stream_name, token, row = received_rows.pop(0)
+            stream_name, token, row = received_event_rows.pop(0)
             self.assertEqual("events", stream_name)
             self.assertIsInstance(row, EventsStreamRow)
             self.assertEqual(row.type, "ev")
@@ -398,9 +426,9 @@ class EventsStreamTestCase(BaseStreamTestCase):
             self.assertEqual(row.data.event_id, pl_events[i].event_id)
 
             # the state rows are unsorted
-            state_rows: List[EventsStreamCurrentStateRow] = []
+            state_rows: list[EventsStreamCurrentStateRow] = []
             for _ in range(STATES_PER_USER + 1):
-                stream_name, token, row = received_rows.pop(0)
+                stream_name, token, row = received_event_rows.pop(0)
                 self.assertEqual("events", stream_name)
                 self.assertIsInstance(row, EventsStreamRow)
                 self.assertEqual(row.type, "state")
@@ -417,7 +445,7 @@ class EventsStreamTestCase(BaseStreamTestCase):
                 # "None" indicates the state has been deleted
                 self.assertIsNone(sr.event_id)
 
-        self.assertEqual([], received_rows)
+        self.assertEqual([], received_event_rows)
 
     def test_backwards_stream_id(self) -> None:
         """
@@ -432,7 +460,12 @@ class EventsStreamTestCase(BaseStreamTestCase):
 
         # check we're testing what we think we are: no rows should yet have been
         # received
-        self.assertEqual([], self.test_handler.received_rdata_rows)
+        received_event_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == EventsStream.NAME
+        ]
+        self.assertEqual([], received_event_rows)
 
         # now reconnect to pull the updates
         self.reconnect()
@@ -440,14 +473,16 @@ class EventsStreamTestCase(BaseStreamTestCase):
 
         # We should have received the expected single row (as well as various
         # cache invalidation updates which we ignore).
-        received_rows = [
-            row for row in self.test_handler.received_rdata_rows if row[0] == "events"
+        received_event_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == EventsStream.NAME
         ]
 
         # There should be a single received row.
-        self.assertEqual(len(received_rows), 1)
+        self.assertEqual(len(received_event_rows), 1)
 
-        stream_name, token, row = received_rows[0]
+        stream_name, token, row = received_event_rows[0]
         self.assertEqual("events", stream_name)
         self.assertIsInstance(row, EventsStreamRow)
         self.assertEqual(row.type, "ev")
@@ -468,10 +503,12 @@ class EventsStreamTestCase(BaseStreamTestCase):
         )
 
         # No updates have been received (because it was discard as old).
-        received_rows = [
-            row for row in self.test_handler.received_rdata_rows if row[0] == "events"
+        received_event_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == EventsStream.NAME
         ]
-        self.assertEqual(len(received_rows), 0)
+        self.assertEqual(len(received_event_rows), 0)
 
         # Ensure the stream has not gone backwards.
         current_token = worker_events_stream.current_token("master")
@@ -480,7 +517,7 @@ class EventsStreamTestCase(BaseStreamTestCase):
     event_count = 0
 
     def _inject_test_event(
-        self, body: Optional[str] = None, sender: Optional[str] = None, **kwargs: Any
+        self, body: str | None = None, sender: str | None = None, **kwargs: Any
     ) -> EventBase:
         if sender is None:
             sender = self.user_id
@@ -502,9 +539,9 @@ class EventsStreamTestCase(BaseStreamTestCase):
 
     def _inject_state_event(
         self,
-        body: Optional[str] = None,
-        state_key: Optional[str] = None,
-        sender: Optional[str] = None,
+        body: str | None = None,
+        state_key: str | None = None,
+        sender: str | None = None,
     ) -> EventBase:
         if sender is None:
             sender = self.user_id
diff --git a/tests/replication/tcp/streams/test_federation.py b/tests/replication/tcp/streams/test_federation.py
index fd81e0dc17..172968c108 100644
--- a/tests/replication/tcp/streams/test_federation.py
+++ b/tests/replication/tcp/streams/test_federation.py
@@ -38,24 +38,45 @@ class FederationStreamTestCase(BaseStreamTestCase):
         Makes sure that updates sent while we are offline are received later.
         """
         fed_sender = self.hs.get_federation_sender()
-        received_rows = self.test_handler.received_rdata_rows
 
+        # Send an update before we connect
         fed_sender.build_and_send_edu("testdest", "m.test_edu", {"a": "b"})
 
+        # Now reconnect and pull the updates
         self.reconnect()
+        # FIXME: This seems odd, why aren't we calling `self.replicate()` here? but also
+        # doing so, causes other assumptions to fail (multiple HTTP replication attempts
+        # are made).
         self.reactor.advance(0)
 
-        # check we're testing what we think we are: no rows should yet have been
+        # Check we're testing what we think we are: no rows should yet have been
         # received
-        self.assertEqual(received_rows, [])
+        #
+        # Filter the updates to only include typing changes
+        received_federation_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == FederationStream.NAME
+        ]
+        self.assertEqual(received_federation_rows, [])
 
         # We should now see an attempt to connect to the master
         request = self.handle_http_replication_attempt()
-        self.assert_request_is_get_repl_stream_updates(request, "federation")
+        self.assert_request_is_get_repl_stream_updates(request, FederationStream.NAME)
 
         # we should have received an update row
-        stream_name, token, row = received_rows.pop()
-        self.assertEqual(stream_name, "federation")
+        received_federation_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == FederationStream.NAME
+        ]
+        self.assertEqual(
+            len(received_federation_rows),
+            1,
+            "Expected exactly one row for the federation stream",
+        )
+        (stream_name, token, row) = received_federation_rows[0]
+        self.assertEqual(stream_name, FederationStream.NAME)
         self.assertIsInstance(row, FederationStream.FederationStreamRow)
         self.assertEqual(row.type, EduRow.TypeId)
         edurow = EduRow.from_data(row.data)
@@ -63,19 +84,30 @@ class FederationStreamTestCase(BaseStreamTestCase):
         self.assertEqual(edurow.edu.origin, self.hs.hostname)
         self.assertEqual(edurow.edu.destination, "testdest")
         self.assertEqual(edurow.edu.content, {"a": "b"})
-
-        self.assertEqual(received_rows, [])
+        # Clear out the received rows that we've checked so we can check for new ones later
+        self.test_handler.received_rdata_rows.clear()
 
         # additional updates should be transferred without an HTTP hit
         fed_sender.build_and_send_edu("testdest", "m.test1", {"c": "d"})
-        self.reactor.advance(0)
+        # Pull in the updates
+        self.replicate()
+
         # there should be no http hit
         self.assertEqual(len(self.reactor.tcpClients), 0)
-        # ... but we should have a row
-        self.assertEqual(len(received_rows), 1)
 
-        stream_name, token, row = received_rows.pop()
-        self.assertEqual(stream_name, "federation")
+        # ... but we should have a row
+        received_federation_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == FederationStream.NAME
+        ]
+        self.assertEqual(
+            len(received_federation_rows),
+            1,
+            "Expected exactly one row for the federation stream",
+        )
+        (stream_name, token, row) = received_federation_rows[0]
+        self.assertEqual(stream_name, FederationStream.NAME)
         self.assertIsInstance(row, FederationStream.FederationStreamRow)
         self.assertEqual(row.type, EduRow.TypeId)
         edurow = EduRow.from_data(row.data)
diff --git a/tests/replication/tcp/streams/test_receipts.py b/tests/replication/tcp/streams/test_receipts.py
index c2f1f8dc4a..c5332f6b5f 100644
--- a/tests/replication/tcp/streams/test_receipts.py
+++ b/tests/replication/tcp/streams/test_receipts.py
@@ -20,7 +20,6 @@
 
 # type: ignore
 
-from unittest.mock import Mock
 
 from synapse.replication.tcp.streams._base import ReceiptsStream
 
@@ -30,9 +29,6 @@ USER_ID = "@feeling:blue"
 
 
 class ReceiptsStreamTestCase(BaseStreamTestCase):
-    def _build_replication_data_handler(self):
-        return Mock(wraps=super()._build_replication_data_handler())
-
     def test_receipt(self):
         self.reconnect()
 
@@ -50,23 +46,30 @@ class ReceiptsStreamTestCase(BaseStreamTestCase):
         self.replicate()
 
         # there should be one RDATA command
-        self.test_handler.on_rdata.assert_called_once()
-        stream_name, _, token, rdata_rows = self.test_handler.on_rdata.call_args[0]
-        self.assertEqual(stream_name, "receipts")
-        self.assertEqual(1, len(rdata_rows))
-        row: ReceiptsStream.ReceiptsStreamRow = rdata_rows[0]
+        received_receipt_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == ReceiptsStream.NAME
+        ]
+        self.assertEqual(
+            len(received_receipt_rows),
+            1,
+            "Expected exactly one row for the receipts stream",
+        )
+        (stream_name, token, row) = received_receipt_rows[0]
+        self.assertEqual(stream_name, ReceiptsStream.NAME)
         self.assertEqual("!room:blue", row.room_id)
         self.assertEqual("m.read", row.receipt_type)
         self.assertEqual(USER_ID, row.user_id)
         self.assertEqual("$event:blue", row.event_id)
         self.assertIsNone(row.thread_id)
         self.assertEqual({"a": 1}, row.data)
+        # Clear out the received rows that we've checked so we can check for new ones later
+        self.test_handler.received_rdata_rows.clear()
 
         # Now let's disconnect and insert some data.
         self.disconnect()
 
-        self.test_handler.on_rdata.reset_mock()
-
         self.get_success(
             self.hs.get_datastores().main.insert_receipt(
                 "!room2:blue",
@@ -79,20 +82,27 @@ class ReceiptsStreamTestCase(BaseStreamTestCase):
         )
         self.replicate()
 
-        # Nothing should have happened as we are disconnected
-        self.test_handler.on_rdata.assert_not_called()
+        # Not yet connected: no rows should yet have been received
+        self.assertEqual([], self.test_handler.received_rdata_rows)
 
+        # Now reconnect and pull the updates
         self.reconnect()
-        self.pump(0.1)
+        self.replicate()
 
         # We should now have caught up and get the missing data
-        self.test_handler.on_rdata.assert_called_once()
-        stream_name, _, token, rdata_rows = self.test_handler.on_rdata.call_args[0]
-        self.assertEqual(stream_name, "receipts")
+        received_receipt_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == ReceiptsStream.NAME
+        ]
+        self.assertEqual(
+            len(received_receipt_rows),
+            1,
+            "Expected exactly one row for the receipts stream",
+        )
+        (stream_name, token, row) = received_receipt_rows[0]
+        self.assertEqual(stream_name, ReceiptsStream.NAME)
         self.assertEqual(token, 3)
-        self.assertEqual(1, len(rdata_rows))
-
-        row: ReceiptsStream.ReceiptsStreamRow = rdata_rows[0]
         self.assertEqual("!room2:blue", row.room_id)
         self.assertEqual("m.read", row.receipt_type)
         self.assertEqual(USER_ID, row.user_id)
diff --git a/tests/replication/tcp/streams/test_thread_subscriptions.py b/tests/replication/tcp/streams/test_thread_subscriptions.py
index 04e46b9d93..5405316048 100644
--- a/tests/replication/tcp/streams/test_thread_subscriptions.py
+++ b/tests/replication/tcp/streams/test_thread_subscriptions.py
@@ -88,15 +88,15 @@ class ThreadSubscriptionsStreamTestCase(BaseStreamTestCase):
 
         # We should have received all the expected rows in the right order
         # Filter the updates to only include thread subscription changes
-        received_rows = [
-            upd
-            for upd in self.test_handler.received_rdata_rows
-            if upd[0] == ThreadSubscriptionsStream.NAME
+        received_thread_subscription_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == ThreadSubscriptionsStream.NAME
         ]
 
         # Verify all the thread subscription updates
         for thread_id in updates:
-            (stream_name, token, row) = received_rows.pop(0)
+            (stream_name, token, row) = received_thread_subscription_rows.pop(0)
             self.assertEqual(stream_name, ThreadSubscriptionsStream.NAME)
             self.assertIsInstance(row, ThreadSubscriptionsStream.ROW_TYPE)
             self.assertEqual(row.user_id, "@test_user:example.org")
@@ -104,14 +104,14 @@ class ThreadSubscriptionsStreamTestCase(BaseStreamTestCase):
             self.assertEqual(row.event_id, thread_id)
 
         # Verify the last update in the different room
-        (stream_name, token, row) = received_rows.pop(0)
+        (stream_name, token, row) = received_thread_subscription_rows.pop(0)
         self.assertEqual(stream_name, ThreadSubscriptionsStream.NAME)
         self.assertIsInstance(row, ThreadSubscriptionsStream.ROW_TYPE)
         self.assertEqual(row.user_id, "@test_user:example.org")
         self.assertEqual(row.room_id, other_room_id)
         self.assertEqual(row.event_id, other_thread_root_id)
 
-        self.assertEqual([], received_rows)
+        self.assertEqual([], received_thread_subscription_rows)
 
     def test_multiple_users_thread_subscription_updates(self) -> None:
         """Test replication with thread subscription updates for multiple users"""
@@ -138,18 +138,18 @@ class ThreadSubscriptionsStreamTestCase(BaseStreamTestCase):
 
         # We should have received all the expected rows
         # Filter the updates to only include thread subscription changes
-        received_rows = [
-            upd
-            for upd in self.test_handler.received_rdata_rows
-            if upd[0] == ThreadSubscriptionsStream.NAME
+        received_thread_subscription_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == ThreadSubscriptionsStream.NAME
         ]
 
         # Should have one update per user
-        self.assertEqual(len(received_rows), len(users))
+        self.assertEqual(len(received_thread_subscription_rows), len(users))
 
         # Verify all updates
         for i, user_id in enumerate(users):
-            (stream_name, token, row) = received_rows[i]
+            (stream_name, token, row) = received_thread_subscription_rows[i]
             self.assertEqual(stream_name, ThreadSubscriptionsStream.NAME)
             self.assertIsInstance(row, ThreadSubscriptionsStream.ROW_TYPE)
             self.assertEqual(row.user_id, user_id)
diff --git a/tests/replication/tcp/streams/test_to_device.py b/tests/replication/tcp/streams/test_to_device.py
index cb07e93d6b..d6fd9f91ed 100644
--- a/tests/replication/tcp/streams/test_to_device.py
+++ b/tests/replication/tcp/streams/test_to_device.py
@@ -21,7 +21,10 @@
 import logging
 
 import synapse
-from synapse.replication.tcp.streams._base import _STREAM_UPDATE_TARGET_ROW_COUNT
+from synapse.replication.tcp.streams._base import (
+    _STREAM_UPDATE_TARGET_ROW_COUNT,
+    ToDeviceStream,
+)
 from synapse.types import JsonDict
 
 from tests.replication._base import BaseStreamTestCase
@@ -82,7 +85,12 @@ class ToDeviceStreamTestCase(BaseStreamTestCase):
         )
 
         # replication is disconnected so we shouldn't get any updates yet
-        self.assertEqual([], self.test_handler.received_rdata_rows)
+        received_to_device_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == ToDeviceStream.NAME
+        ]
+        self.assertEqual([], received_to_device_rows)
 
         # now reconnect to pull the updates
         self.reconnect()
@@ -90,7 +98,15 @@ class ToDeviceStreamTestCase(BaseStreamTestCase):
 
         # we should receive the fact that we have to_device updates
         # for user1 and user2
-        received_rows = self.test_handler.received_rdata_rows
-        self.assertEqual(len(received_rows), 2)
-        self.assertEqual(received_rows[0][2].entity, user1)
-        self.assertEqual(received_rows[1][2].entity, user2)
+        received_to_device_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == ToDeviceStream.NAME
+        ]
+        self.assertEqual(
+            len(received_to_device_rows),
+            2,
+            "Expected two rows in the to_device stream",
+        )
+        self.assertEqual(received_to_device_rows[0][2].entity, user1)
+        self.assertEqual(received_to_device_rows[1][2].entity, user2)
diff --git a/tests/replication/tcp/streams/test_typing.py b/tests/replication/tcp/streams/test_typing.py
index e2b2299106..df91416b9b 100644
--- a/tests/replication/tcp/streams/test_typing.py
+++ b/tests/replication/tcp/streams/test_typing.py
@@ -19,7 +19,6 @@
 #
 #
 import logging
-from unittest.mock import Mock
 
 from synapse.handlers.typing import RoomMember, TypingWriterHandler
 from synapse.replication.tcp.streams import TypingStream
@@ -27,6 +26,8 @@ from synapse.util.caches.stream_change_cache import StreamChangeCache
 
 from tests.replication._base import BaseStreamTestCase
 
+logger = logging.getLogger(__name__)
+
 USER_ID = "@feeling:blue"
 USER_ID_2 = "@da-ba-dee:blue"
 
@@ -35,10 +36,6 @@ ROOM_ID_2 = "!foo:blue"
 
 
 class TypingStreamTestCase(BaseStreamTestCase):
-    def _build_replication_data_handler(self) -> Mock:
-        self.mock_handler = Mock(wraps=super()._build_replication_data_handler())
-        return self.mock_handler
-
     def test_typing(self) -> None:
         typing = self.hs.get_typing_handler()
         assert isinstance(typing, TypingWriterHandler)
@@ -47,51 +44,74 @@ class TypingStreamTestCase(BaseStreamTestCase):
         # update to fetch.
         typing._push_update(member=RoomMember(ROOM_ID, USER_ID), typing=True)
 
+        # Not yet connected: no rows should yet have been received
+        self.assertEqual([], self.test_handler.received_rdata_rows)
+
+        # Reconnect
         self.reconnect()
 
         typing._push_update(member=RoomMember(ROOM_ID, USER_ID), typing=True)
-
-        self.reactor.advance(0)
+        # Pull in the updates
+        self.replicate()
 
         # We should now see an attempt to connect to the master
         request = self.handle_http_replication_attempt()
-        self.assert_request_is_get_repl_stream_updates(request, "typing")
+        self.assert_request_is_get_repl_stream_updates(request, TypingStream.NAME)
 
-        self.mock_handler.on_rdata.assert_called_once()
-        stream_name, _, token, rdata_rows = self.mock_handler.on_rdata.call_args[0]
-        self.assertEqual(stream_name, "typing")
-        self.assertEqual(1, len(rdata_rows))
-        row: TypingStream.TypingStreamRow = rdata_rows[0]
-        self.assertEqual(ROOM_ID, row.room_id)
-        self.assertEqual([USER_ID], row.user_ids)
+        # Filter the updates to only include typing changes
+        received_typing_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == TypingStream.NAME
+        ]
+        self.assertEqual(
+            len(received_typing_rows),
+            1,
+            "Expected exactly one row for the typing stream",
+        )
+        (stream_name, token, row) = received_typing_rows[0]
+        self.assertEqual(stream_name, TypingStream.NAME)
+        self.assertIsInstance(row, TypingStream.ROW_TYPE)
+        self.assertEqual(row.room_id, ROOM_ID)
+        self.assertEqual(row.user_ids, [USER_ID])
+        # Clear out the received rows that we've checked so we can check for new ones later
+        self.test_handler.received_rdata_rows.clear()
 
         # Now let's disconnect and insert some data.
         self.disconnect()
 
-        self.mock_handler.on_rdata.reset_mock()
-
         typing._push_update(member=RoomMember(ROOM_ID, USER_ID), typing=False)
 
-        self.mock_handler.on_rdata.assert_not_called()
+        # Not yet connected: no rows should yet have been received
+        self.assertEqual([], self.test_handler.received_rdata_rows)
 
+        # Now reconnect and pull the updates
         self.reconnect()
-        self.pump(0.1)
+        self.replicate()
 
         # We should now see an attempt to connect to the master
         request = self.handle_http_replication_attempt()
-        self.assert_request_is_get_repl_stream_updates(request, "typing")
+        self.assert_request_is_get_repl_stream_updates(request, TypingStream.NAME)
 
         # The from token should be the token from the last RDATA we got.
         assert request.args is not None
         self.assertEqual(int(request.args[b"from_token"][0]), token)
 
-        self.mock_handler.on_rdata.assert_called_once()
-        stream_name, _, token, rdata_rows = self.mock_handler.on_rdata.call_args[0]
-        self.assertEqual(stream_name, "typing")
-        self.assertEqual(1, len(rdata_rows))
-        row = rdata_rows[0]
-        self.assertEqual(ROOM_ID, row.room_id)
-        self.assertEqual([], row.user_ids)
+        received_typing_rows = [
+            row
+            for row in self.test_handler.received_rdata_rows
+            if row[0] == TypingStream.NAME
+        ]
+        self.assertEqual(
+            len(received_typing_rows),
+            1,
+            "Expected exactly one row for the typing stream",
+        )
+        (stream_name, token, row) = received_typing_rows[0]
+        self.assertEqual(stream_name, TypingStream.NAME)
+        self.assertIsInstance(row, TypingStream.ROW_TYPE)
+        self.assertEqual(row.room_id, ROOM_ID)
+        self.assertEqual(row.user_ids, [])
 
     def test_reset(self) -> None:
         """
@@ -116,33 +136,47 @@ class TypingStreamTestCase(BaseStreamTestCase):
             # update to fetch.
             typing._push_update(member=RoomMember(ROOM_ID, USER_ID), typing=True)
 
+            # Not yet connected: no rows should yet have been received
+            self.assertEqual([], self.test_handler.received_rdata_rows)
+
+            # Now reconnect to pull the updates
             self.reconnect()
 
             typing._push_update(member=RoomMember(ROOM_ID, USER_ID), typing=True)
-
-            self.reactor.advance(0)
+            # Pull in the updates
+            self.replicate()
 
             # We should now see an attempt to connect to the master
             request = self.handle_http_replication_attempt()
             self.assert_request_is_get_repl_stream_updates(request, "typing")
 
-            self.mock_handler.on_rdata.assert_called_once()
-            stream_name, _, token, rdata_rows = self.mock_handler.on_rdata.call_args[0]
-            self.assertEqual(stream_name, "typing")
-            self.assertEqual(1, len(rdata_rows))
-            row: TypingStream.TypingStreamRow = rdata_rows[0]
-            self.assertEqual(ROOM_ID, row.room_id)
-            self.assertEqual([USER_ID], row.user_ids)
+            received_typing_rows = [
+                row
+                for row in self.test_handler.received_rdata_rows
+                if row[0] == TypingStream.NAME
+            ]
+            self.assertEqual(
+                len(received_typing_rows),
+                1,
+                "Expected exactly one row for the typing stream",
+            )
+            (stream_name, token, row) = received_typing_rows[0]
+            self.assertEqual(stream_name, TypingStream.NAME)
+            self.assertIsInstance(row, TypingStream.ROW_TYPE)
+            self.assertEqual(row.room_id, ROOM_ID)
+            self.assertEqual(row.user_ids, [USER_ID])
 
             # Push the stream forward a bunch so it can be reset.
             for i in range(100):
                 typing._push_update(
                     member=RoomMember(ROOM_ID, "@test%s:blue" % i), typing=True
                 )
-            self.reactor.advance(0)
+            # Pull in the updates
+            self.replicate()
 
             # Disconnect.
             self.disconnect()
+            self.test_handler.received_rdata_rows.clear()
 
             # Reset the typing handler
             self.hs.get_replication_streams()["typing"].last_token = 0
@@ -155,30 +189,34 @@ class TypingStreamTestCase(BaseStreamTestCase):
             )
             typing._reset()
 
-            # Reconnect.
+            # Now reconnect and pull the updates
             self.reconnect()
-            self.pump(0.1)
+            self.replicate()
 
             # We should now see an attempt to connect to the master
             request = self.handle_http_replication_attempt()
             self.assert_request_is_get_repl_stream_updates(request, "typing")
 
-            # Reset the test code.
-            self.mock_handler.on_rdata.reset_mock()
-            self.mock_handler.on_rdata.assert_not_called()
-
             # Push additional data.
             typing._push_update(member=RoomMember(ROOM_ID_2, USER_ID_2), typing=False)
-            self.reactor.advance(0)
-
-            self.mock_handler.on_rdata.assert_called_once()
-            stream_name, _, token, rdata_rows = self.mock_handler.on_rdata.call_args[0]
-            self.assertEqual(stream_name, "typing")
-            self.assertEqual(1, len(rdata_rows))
-            row = rdata_rows[0]
-            self.assertEqual(ROOM_ID_2, row.room_id)
-            self.assertEqual([], row.user_ids)
+            # Pull the updates
+            self.replicate()
 
+            received_typing_rows = [
+                row
+                for row in self.test_handler.received_rdata_rows
+                if row[0] == TypingStream.NAME
+            ]
+            self.assertEqual(
+                len(received_typing_rows),
+                1,
+                "Expected exactly one row for the typing stream",
+            )
+            (stream_name, token, row) = received_typing_rows[0]
+            self.assertEqual(stream_name, TypingStream.NAME)
+            self.assertIsInstance(row, TypingStream.ROW_TYPE)
+            self.assertEqual(row.room_id, ROOM_ID_2)
+            self.assertEqual(row.user_ids, [])
             # The token should have been reset.
             self.assertEqual(token, 1)
         finally:
diff --git a/tests/replication/test_federation_sender_shard.py b/tests/replication/test_federation_sender_shard.py
index 92259f2542..3896e0ce8a 100644
--- a/tests/replication/test_federation_sender_shard.py
+++ b/tests/replication/test_federation_sender_shard.py
@@ -66,10 +66,11 @@ class FederationSenderTestCase(BaseMultiWorkerStreamTestCase):
     def setUp(self) -> None:
         super().setUp()
 
-        reactor, _ = get_clock()
+        reactor, clock = get_clock()
         self.matrix_federation_agent = MatrixFederationAgent(
             server_name="OUR_STUB_HOMESERVER_NAME",
             reactor=reactor,
+            clock=clock,
             tls_client_options_factory=None,
             user_agent=b"SynapseInTrialTest/0.0.0",
             ip_allowlist=None,
diff --git a/tests/replication/test_module_cache_invalidation.py b/tests/replication/test_module_cache_invalidation.py
index 8d5d0cce9a..1cb898673b 100644
--- a/tests/replication/test_module_cache_invalidation.py
+++ b/tests/replication/test_module_cache_invalidation.py
@@ -24,6 +24,7 @@ import synapse
 from synapse.module_api import cached
 
 from tests.replication._base import BaseMultiWorkerStreamTestCase
+from tests.server import get_clock
 
 logger = logging.getLogger(__name__)
 
@@ -36,6 +37,7 @@ KEY = "mykey"
 class TestCache:
     current_value = FIRST_VALUE
     server_name = "test_server"  # nb must be called this for @cached
+    _, clock = get_clock()  # nb must be called this for @cached
 
     @cached()
     async def cached_function(self, user_id: str) -> str:
diff --git a/tests/replication/test_multi_media_repo.py b/tests/replication/test_multi_media_repo.py
index f712ad1fe3..8dbb989850 100644
--- a/tests/replication/test_multi_media_repo.py
+++ b/tests/replication/test_multi_media_repo.py
@@ -20,7 +20,7 @@
 #
 import logging
 import os
-from typing import Any, Optional, Tuple
+from typing import Any
 
 from twisted.internet.protocol import Factory
 from twisted.internet.testing import MemoryReactor
@@ -44,7 +44,7 @@ from tests.unittest import override_config
 
 logger = logging.getLogger(__name__)
 
-test_server_connection_factory: Optional[TestServerTLSConnectionFactory] = None
+test_server_connection_factory: TestServerTLSConnectionFactory | None = None
 
 
 class MediaRepoShardTestCase(BaseMultiWorkerStreamTestCase):
@@ -67,7 +67,7 @@ class MediaRepoShardTestCase(BaseMultiWorkerStreamTestCase):
         return conf
 
     def make_worker_hs(
-        self, worker_app: str, extra_config: Optional[dict] = None, **kwargs: Any
+        self, worker_app: str, extra_config: dict | None = None, **kwargs: Any
     ) -> HomeServer:
         worker_hs = super().make_worker_hs(worker_app, extra_config, **kwargs)
         # Force the media paths onto the replication resource.
@@ -78,7 +78,7 @@ class MediaRepoShardTestCase(BaseMultiWorkerStreamTestCase):
 
     def _get_media_req(
         self, hs: HomeServer, target: str, media_id: str
-    ) -> Tuple[FakeChannel, Request]:
+    ) -> tuple[FakeChannel, Request]:
         """Request some remote media from the given HS by calling the download
         API.
 
@@ -282,7 +282,7 @@ class AuthenticatedMediaRepoShardTestCase(BaseMultiWorkerStreamTestCase):
         return conf
 
     def make_worker_hs(
-        self, worker_app: str, extra_config: Optional[dict] = None, **kwargs: Any
+        self, worker_app: str, extra_config: dict | None = None, **kwargs: Any
     ) -> HomeServer:
         worker_hs = super().make_worker_hs(worker_app, extra_config, **kwargs)
         # Force the media paths onto the replication resource.
@@ -293,7 +293,7 @@ class AuthenticatedMediaRepoShardTestCase(BaseMultiWorkerStreamTestCase):
 
     def _get_media_req(
         self, hs: HomeServer, target: str, media_id: str
-    ) -> Tuple[FakeChannel, Request]:
+    ) -> tuple[FakeChannel, Request]:
         """Request some remote media from the given HS by calling the download
         API.
 
diff --git a/tests/rest/admin/test_admin.py b/tests/rest/admin/test_admin.py
index 2a17389feb..f3740a8e35 100644
--- a/tests/rest/admin/test_admin.py
+++ b/tests/rest/admin/test_admin.py
@@ -20,7 +20,7 @@
 #
 
 import urllib.parse
-from typing import Dict, cast
+from typing import cast
 
 from parameterized import parameterized
 
@@ -65,7 +65,7 @@ class QuarantineMediaTestCase(unittest.HomeserverTestCase):
         room.register_servlets,
     ]
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         resources = super().create_resource_dict()
         resources["/_matrix/media"] = self.hs.get_media_repository_resource()
         return resources
diff --git a/tests/rest/admin/test_event.py b/tests/rest/admin/test_event.py
new file mode 100644
index 0000000000..4494804210
--- /dev/null
+++ b/tests/rest/admin/test_event.py
@@ -0,0 +1,74 @@
+from twisted.internet.testing import MemoryReactor
+
+import synapse.rest.admin
+from synapse.api.errors import Codes
+from synapse.rest.client import login, room
+from synapse.server import HomeServer
+from synapse.util.clock import Clock
+
+from tests import unittest
+
+
+class FetchEventTestCase(unittest.HomeserverTestCase):
+    servlets = [
+        synapse.rest.admin.register_servlets,
+        login.register_servlets,
+        room.register_servlets,
+    ]
+
+    def prepare(self, reactor: MemoryReactor, clock: Clock, hs: HomeServer) -> None:
+        self.admin_user = self.register_user("admin", "pass", admin=True)
+        self.admin_user_tok = self.login("admin", "pass")
+
+        self.other_user = self.register_user("user", "pass")
+        self.other_user_tok = self.login("user", "pass")
+
+        self.room_id1 = self.helper.create_room_as(
+            self.other_user, tok=self.other_user_tok, is_public=True
+        )
+        resp = self.helper.send(self.room_id1, body="Hey now", tok=self.other_user_tok)
+        self.event_id = resp["event_id"]
+
+    def test_no_auth(self) -> None:
+        """
+        Try to get an event without authentication.
+        """
+        channel = self.make_request(
+            "GET",
+            f"/_synapse/admin/v1/fetch_event/{self.event_id}",
+        )
+
+        self.assertEqual(401, channel.code, msg=channel.json_body)
+        self.assertEqual(Codes.MISSING_TOKEN, channel.json_body["errcode"])
+
+    def test_requester_is_not_admin(self) -> None:
+        """
+        If the user is not a server admin, an error 403 is returned.
+        """
+
+        channel = self.make_request(
+            "GET",
+            f"/_synapse/admin/v1/fetch_event/{self.event_id}",
+            access_token=self.other_user_tok,
+        )
+
+        self.assertEqual(403, channel.code, msg=channel.json_body)
+        self.assertEqual(Codes.FORBIDDEN, channel.json_body["errcode"])
+
+    def test_fetch_event(self) -> None:
+        """
+        Test that we can successfully fetch an event
+        """
+        channel = self.make_request(
+            "GET",
+            f"/_synapse/admin/v1/fetch_event/{self.event_id}",
+            access_token=self.admin_user_tok,
+        )
+        self.assertEqual(200, channel.code, msg=channel.json_body)
+        self.assertEqual(
+            channel.json_body["event"]["content"],
+            {"body": "Hey now", "msgtype": "m.text"},
+        )
+        self.assertEqual(channel.json_body["event"]["event_id"], self.event_id)
+        self.assertEqual(channel.json_body["event"]["type"], "m.room.message")
+        self.assertEqual(channel.json_body["event"]["sender"], self.other_user)
diff --git a/tests/rest/admin/test_event_reports.py b/tests/rest/admin/test_event_reports.py
index 28be7fcd97..19d945bb42 100644
--- a/tests/rest/admin/test_event_reports.py
+++ b/tests/rest/admin/test_event_reports.py
@@ -18,7 +18,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import List
 
 from twisted.internet.testing import MemoryReactor
 
@@ -441,7 +440,7 @@ class EventReportsTestCase(unittest.HomeserverTestCase):
         )
         self.assertEqual(200, channel.code, msg=channel.json_body)
 
-    def _check_fields(self, content: List[JsonDict]) -> None:
+    def _check_fields(self, content: list[JsonDict]) -> None:
         """Checks that all attributes are present in an event report"""
         for c in content:
             self.assertIn("id", c)
diff --git a/tests/rest/admin/test_federation.py b/tests/rest/admin/test_federation.py
index d0b57d1faa..561566de76 100644
--- a/tests/rest/admin/test_federation.py
+++ b/tests/rest/admin/test_federation.py
@@ -18,7 +18,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import List, Optional
 
 from parameterized import parameterized
 
@@ -272,9 +271,9 @@ class FederationTestCase(unittest.HomeserverTestCase):
         """Testing order list with parameter `order_by`"""
 
         def _order_test(
-            expected_destination_list: List[str],
-            order_by: Optional[str],
-            dir: Optional[str] = None,
+            expected_destination_list: list[str],
+            order_by: str | None,
+            dir: str | None = None,
         ) -> None:
             """Request the list of destinations in a certain order.
             Assert that order is what we expect
@@ -366,7 +365,7 @@ class FederationTestCase(unittest.HomeserverTestCase):
         """Test that searching for a destination works correctly"""
 
         def _search_test(
-            expected_destination: Optional[str],
+            expected_destination: str | None,
             search_term: str,
         ) -> None:
             """Search for a destination and check that the returned destinationis a match
@@ -484,10 +483,10 @@ class FederationTestCase(unittest.HomeserverTestCase):
     def _create_destination(
         self,
         destination: str,
-        failure_ts: Optional[int] = None,
+        failure_ts: int | None = None,
         retry_last_ts: int = 0,
         retry_interval: int = 0,
-        last_successful_stream_ordering: Optional[int] = None,
+        last_successful_stream_ordering: int | None = None,
     ) -> None:
         """Create one specific destination
 
@@ -521,7 +520,7 @@ class FederationTestCase(unittest.HomeserverTestCase):
             dest = f"sub{i}.example.com"
             self._create_destination(dest, 50, 50, 50, 100)
 
-    def _check_fields(self, content: List[JsonDict]) -> None:
+    def _check_fields(self, content: list[JsonDict]) -> None:
         """Checks that the expected destination attributes are present in content
 
         Args:
@@ -819,8 +818,8 @@ class DestinationMembershipTestCase(unittest.HomeserverTestCase):
     def _create_destination_rooms(
         self,
         number_rooms: int,
-        destination: Optional[str] = None,
-    ) -> List[str]:
+        destination: str | None = None,
+    ) -> list[str]:
         """
         Create the given number of rooms. The given `destination` homeserver will
         be recorded as a participant.
@@ -853,7 +852,7 @@ class DestinationMembershipTestCase(unittest.HomeserverTestCase):
 
         return room_ids
 
-    def _check_fields(self, content: List[JsonDict]) -> None:
+    def _check_fields(self, content: list[JsonDict]) -> None:
         """Checks that the expected room attributes are present in content
 
         Args:
diff --git a/tests/rest/admin/test_jwks.py b/tests/rest/admin/test_jwks.py
index 55b822c4d0..ee5588951b 100644
--- a/tests/rest/admin/test_jwks.py
+++ b/tests/rest/admin/test_jwks.py
@@ -19,7 +19,6 @@
 #
 #
 
-from typing import Dict
 
 from twisted.web.resource import Resource
 
@@ -33,7 +32,7 @@ from tests.utils import HAS_AUTHLIB
 class JWKSTestCase(HomeserverTestCase):
     """Test /_synapse/jwks JWKS data."""
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         d = super().create_resource_dict()
         d.update(build_synapse_client_resource_tree(self.hs))
         return d
diff --git a/tests/rest/admin/test_media.py b/tests/rest/admin/test_media.py
index 86c09634cc..8cc54cc80c 100644
--- a/tests/rest/admin/test_media.py
+++ b/tests/rest/admin/test_media.py
@@ -20,7 +20,6 @@
 #
 #
 import os
-from typing import Dict
 
 from parameterized import parameterized
 
@@ -51,7 +50,7 @@ class _AdminMediaTests(unittest.HomeserverTestCase):
         media.register_servlets,
     ]
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         resources = super().create_resource_dict()
         resources["/_matrix/media"] = self.hs.get_media_repository_resource()
         return resources
diff --git a/tests/rest/admin/test_registration_tokens.py b/tests/rest/admin/test_registration_tokens.py
index 9afe86b724..447e1098e5 100644
--- a/tests/rest/admin/test_registration_tokens.py
+++ b/tests/rest/admin/test_registration_tokens.py
@@ -20,7 +20,6 @@
 #
 import random
 import string
-from typing import Optional
 
 from twisted.internet.testing import MemoryReactor
 
@@ -51,11 +50,11 @@ class ManageRegistrationTokensTestCase(unittest.HomeserverTestCase):
 
     def _new_token(
         self,
-        token: Optional[str] = None,
-        uses_allowed: Optional[int] = None,
+        token: str | None = None,
+        uses_allowed: int | None = None,
         pending: int = 0,
         completed: int = 0,
-        expiry_time: Optional[int] = None,
+        expiry_time: int | None = None,
     ) -> str:
         """Helper function to create a token."""
         if token is None:
diff --git a/tests/rest/admin/test_room.py b/tests/rest/admin/test_room.py
index 30b2de26e4..7daf13ad22 100644
--- a/tests/rest/admin/test_room.py
+++ b/tests/rest/admin/test_room.py
@@ -22,16 +22,14 @@ import json
 import time
 import urllib.parse
 from http import HTTPStatus
-from typing import List, Optional
 from unittest.mock import AsyncMock, Mock
 
 from parameterized import parameterized
 
-from twisted.internet.task import deferLater
 from twisted.internet.testing import MemoryReactor
 
 import synapse.rest.admin
-from synapse.api.constants import EventTypes, Membership, RoomTypes
+from synapse.api.constants import EventContentFields, EventTypes, Membership, RoomTypes
 from synapse.api.errors import Codes
 from synapse.api.room_versions import RoomVersions
 from synapse.handlers.pagination import (
@@ -56,6 +54,308 @@ from tests import unittest
 ONE_HOUR_IN_S = 3600
 
 
+class AdminHierarchyTestCase(unittest.HomeserverTestCase):
+    servlets = [
+        synapse.rest.admin.register_servlets,
+        login.register_servlets,
+        room.register_servlets,
+    ]
+
+    def prepare(self, reactor: MemoryReactor, clock: Clock, hs: HomeServer) -> None:
+        # create some users
+        self.admin_user = self.register_user("admin", "pass", admin=True)
+        self.admin_user_tok = self.login("admin", "pass")
+
+        self.other_user = self.register_user("user", "pass")
+        self.other_user_tok = self.login("user", "pass")
+
+        self.third_user = self.register_user("third_user", "pass")
+        self.third_user_tok = self.login("third_user", "pass")
+
+        # mock out the function which pulls room information in over federation.
+        self._room_summary_handler = hs.get_room_summary_handler()
+        self._room_summary_handler._summarize_remote_room_hierarchy = Mock()  # type: ignore[method-assign]
+
+        # create some rooms with different options
+        self.room_id1 = self.helper.create_room_as(
+            self.other_user,
+            is_public=False,
+            tok=self.other_user_tok,
+            extra_content={"name": "nefarious", "topic": "being bad"},
+        )
+
+        self.room_id2 = self.helper.create_room_as(
+            self.third_user,
+            tok=self.third_user_tok,
+            extra_content={"name": "also nefarious"},
+        )
+
+        self.room_id3 = self.helper.create_room_as(
+            self.admin_user,
+            is_public=False,
+            tok=self.admin_user_tok,
+            extra_content={
+                "name": "not nefarious",
+                "topic": "happy things",
+                "creation_content": {
+                    "additional_creators": [self.other_user, self.third_user]
+                },
+            },
+            room_version="12",
+        )
+
+        self.not_in_space_room_id = self.helper.create_room_as(
+            self.other_user,
+            tok=self.other_user_tok,
+            extra_content={"name": "not related to other rooms"},
+        )
+
+        # create a space room
+        self.space_room_id = self.helper.create_room_as(
+            self.other_user,
+            is_public=True,
+            extra_content={
+                "visibility": "public",
+                "creation_content": {EventContentFields.ROOM_TYPE: RoomTypes.SPACE},
+                "name": "space_room",
+            },
+            tok=self.other_user_tok,
+        )
+
+        # and an unjoined remote room
+        self.remote_room_id = "!remote_room"
+
+        self.room_id_to_human_name_map = {
+            self.room_id1: "room1",
+            self.room_id2: "room2",
+            self.room_id3: "room3",
+            self.not_in_space_room_id: "room4",
+            self.space_room_id: "space_room",
+            self.remote_room_id: "remote_room",
+        }
+
+        # add three of the rooms to space
+        for state_key in [self.room_id1, self.room_id2, self.room_id3]:
+            self.helper.send_state(
+                self.space_room_id,
+                EventTypes.SpaceChild,
+                body={"via": ["local_test_server"]},
+                tok=self.other_user_tok,
+                state_key=state_key,
+            )
+
+        # and add remote room to space - ideally we'd add an actual remote
+        # space with rooms in it but the test framework doesn't currently
+        # support that. Instead we add a room which the server would have to
+        # reach out over federation to get details about and assert that the
+        # federation call was not made
+        self.helper.send_state(
+            self.space_room_id,
+            EventTypes.SpaceChild,
+            body={"via": ["remote_test_server"]},
+            tok=self.other_user_tok,
+            state_key=self.remote_room_id,
+        )
+
+    def test_no_auth(self) -> None:
+        """
+        If the requester does not provide authentication, a 401 is returned
+        """
+
+        channel = self.make_request(
+            "GET",
+            f"/_synapse/admin/v1/rooms/{self.space_room_id}/hierarchy",
+        )
+
+        self.assertEqual(401, channel.code, msg=channel.json_body)
+        self.assertEqual(Codes.MISSING_TOKEN, channel.json_body["errcode"])
+
+    def test_requester_is_no_admin(self) -> None:
+        """
+        If the requester is not a server admin, an error 403 is returned.
+        """
+
+        channel = self.make_request(
+            "GET",
+            f"/_synapse/admin/v1/rooms/{self.space_room_id}/hierarchy",
+            access_token=self.other_user_tok,
+        )
+
+        self.assertEqual(403, channel.code, msg=channel.json_body)
+        self.assertEqual(Codes.FORBIDDEN, channel.json_body["errcode"])
+
+    def test_bad_request(self) -> None:
+        """
+        Test that invalid param values raise an error
+        """
+        channel = self.make_request(
+            "GET",
+            f"/_synapse/admin/v1/rooms/{self.space_room_id}/hierarchy?limit=ten",
+            access_token=self.admin_user_tok,
+        )
+        self.assertEqual(400, channel.code, msg=channel.json_body)
+        self.assertEqual(Codes.INVALID_PARAM, channel.json_body["errcode"])
+
+        channel = self.make_request(
+            "GET",
+            f"/_synapse/admin/v1/rooms/{self.space_room_id}/hierarchy?max_depth=four",
+            access_token=self.admin_user_tok,
+        )
+        self.assertEqual(400, channel.code, msg=channel.json_body)
+        self.assertEqual(Codes.INVALID_PARAM, channel.json_body["errcode"])
+
+    def test_room_summary(self) -> None:
+        """
+        Test that details of room and details of children of room are
+        provided correctly
+        """
+
+        channel = self.make_request(
+            "GET",
+            f"/_synapse/admin/v1/rooms/{self.space_room_id}/hierarchy",
+            access_token=self.admin_user_tok,
+        )
+        self.assertEqual(channel.code, 200, msg=channel.json_body)
+        rooms = channel.json_body["rooms"]
+        self.assertCountEqual(
+            {
+                self.room_id_to_human_name_map.get(
+                    room["room_id"], f"Unknown room: {room['room_id']}"
+                )
+                for room in rooms
+            },
+            {"space_room", "room1", "room2", "room3"},
+        )
+
+        for room_result in rooms:
+            room_id = room_result["room_id"]
+            if room_id == self.room_id1:
+                self.assertEqual(room_result["name"], "nefarious")
+                self.assertEqual(room_result["topic"], "being bad")
+                self.assertEqual(room_result["join_rule"], "invite")
+                self.assertEqual(len(room_result["children_state"]), 0)
+                self.assertEqual(room_result["world_readable"], False)
+                self.assertEqual(room_result["guest_can_join"], True)
+                self.assertEqual(room_result["num_joined_members"], 1)
+            elif room_id == self.room_id2:
+                self.assertEqual(room_result["name"], "also nefarious")
+                self.assertEqual(room_result["join_rule"], "public")
+                self.assertEqual(len(room_result["children_state"]), 0)
+                self.assertEqual(room_result["world_readable"], False)
+                self.assertEqual(room_result["guest_can_join"], False)
+                self.assertEqual(room_result["num_joined_members"], 1)
+            elif room_id == self.room_id3:
+                self.assertEqual(room_result["name"], "not nefarious")
+                self.assertEqual(room_result["join_rule"], "invite")
+                self.assertEqual(room_result["topic"], "happy things")
+                self.assertEqual(len(room_result["children_state"]), 0)
+                self.assertEqual(room_result["world_readable"], False)
+                self.assertEqual(room_result["guest_can_join"], True)
+                self.assertEqual(room_result["num_joined_members"], 1)
+            elif room_id == self.not_in_space_room_id:
+                self.fail("this room should not have been returned")
+            elif room_id == self.space_room_id:
+                self.assertEqual(room_result["join_rule"], "public")
+                self.assertEqual(len(room_result["children_state"]), 4)
+                self.assertEqual(room_result["room_type"], "m.space")
+                self.assertEqual(room_result["world_readable"], False)
+                self.assertEqual(room_result["guest_can_join"], False)
+                self.assertEqual(room_result["num_joined_members"], 1)
+                self.assertEqual(room_result["name"], "space_room")
+            else:
+                self.fail("unknown room returned")
+
+        # Assert that a federation function to look up details about
+        # this room has not been called. We never expect the admin
+        # hierarchy endpoint to reach out over federation.
+        self._room_summary_handler._summarize_remote_room_hierarchy.assert_not_called()  # type: ignore[attr-defined]
+
+    def test_room_summary_pagination(self) -> None:
+        """
+        Test that details of room and details of children of room are provided
+        correctly when paginating
+        """
+
+        channel = self.make_request(
+            "GET",
+            f"/_synapse/admin/v1/rooms/{self.space_room_id}/hierarchy?limit=2",
+            access_token=self.admin_user_tok,
+        )
+        self.assertEqual(channel.code, 200, msg=channel.json_body)
+        rooms = channel.json_body["rooms"]
+        self.assertCountEqual(
+            {
+                self.room_id_to_human_name_map.get(
+                    room["room_id"], f"Unknown room: {room['room_id']}"
+                )
+                for room in rooms
+            },
+            {"space_room", "room1"},
+        )
+        next_batch = channel.json_body["next_batch"]
+
+        channel2 = self.make_request(
+            "GET",
+            f"/_synapse/admin/v1/rooms/{self.space_room_id}/hierarchy?from={next_batch}",
+            access_token=self.admin_user_tok,
+        )
+        self.assertEqual(channel2.code, 200, msg=channel2.json_body)
+        new_rooms = channel2.json_body["rooms"]
+        self.assertCountEqual(
+            {
+                self.room_id_to_human_name_map.get(
+                    room["room_id"], f"Unknown room: {room['room_id']}"
+                )
+                for room in new_rooms
+            },
+            {"room2", "room3"},
+        )
+
+        rooms_to_check = rooms + new_rooms
+        for room_result in rooms_to_check:
+            room_id = room_result["room_id"]
+            if room_id == self.room_id1:
+                self.assertEqual(room_result["name"], "nefarious")
+                self.assertEqual(room_result["topic"], "being bad")
+                self.assertEqual(room_result["join_rule"], "invite")
+                self.assertEqual(len(room_result["children_state"]), 0)
+                self.assertEqual(room_result["world_readable"], False)
+                self.assertEqual(room_result["guest_can_join"], True)
+                self.assertEqual(room_result["num_joined_members"], 1)
+            elif room_id == self.room_id2:
+                self.assertEqual(room_result["name"], "also nefarious")
+                self.assertEqual(room_result["join_rule"], "public")
+                self.assertEqual(len(room_result["children_state"]), 0)
+                self.assertEqual(room_result["world_readable"], False)
+                self.assertEqual(room_result["guest_can_join"], False)
+                self.assertEqual(room_result["num_joined_members"], 1)
+            elif room_id == self.room_id3:
+                self.assertEqual(room_result["name"], "not nefarious")
+                self.assertEqual(room_result["join_rule"], "invite")
+                self.assertEqual(room_result["topic"], "happy things")
+                self.assertEqual(len(room_result["children_state"]), 0)
+                self.assertEqual(room_result["world_readable"], False)
+                self.assertEqual(room_result["guest_can_join"], True)
+                self.assertEqual(room_result["num_joined_members"], 1)
+            elif room_id == self.not_in_space_room_id:
+                self.fail("this room should not have been returned")
+            elif room_id == self.space_room_id:
+                self.assertEqual(room_result["join_rule"], "public")
+                self.assertEqual(len(room_result["children_state"]), 4)
+                self.assertEqual(room_result["room_type"], "m.space")
+                self.assertEqual(room_result["world_readable"], False)
+                self.assertEqual(room_result["guest_can_join"], False)
+                self.assertEqual(room_result["num_joined_members"], 1)
+                self.assertEqual(room_result["name"], "space_room")
+            else:
+                self.fail("unknown room returned")
+
+        # Assert that a federation function to look up details about
+        # this room has not been called. We never expect the admin
+        # hierarchy endpoint to reach out over federation.
+        self._room_summary_handler._summarize_remote_room_hierarchy.assert_not_called()  # type: ignore[attr-defined]
+
+
 class DeleteRoomTestCase(unittest.HomeserverTestCase):
     servlets = [
         synapse.rest.admin.register_servlets,
@@ -861,7 +1161,7 @@ class DeleteRoomV2TestCase(unittest.HomeserverTestCase):
         # Mock PaginationHandler.purge_room to sleep for 100s, so we have time to do a second call
         # before the purge is over. Note that it doesn't purge anymore, but we don't care.
         async def purge_room(room_id: str, force: bool) -> None:
-            await deferLater(self.hs.get_reactor(), 100, lambda: None)
+            await self.hs.get_clock().sleep(100)
 
         self.pagination_handler.purge_room = AsyncMock(side_effect=purge_room)  # type: ignore[method-assign]
 
@@ -1609,7 +1909,7 @@ class RoomTestCase(unittest.HomeserverTestCase):
 
         def _order_test(
             order_type: str,
-            expected_room_list: List[str],
+            expected_room_list: list[str],
             reverse: bool = False,
         ) -> None:
             """Request the list of rooms in a certain order. Assert that order is what
@@ -1773,7 +2073,7 @@ class RoomTestCase(unittest.HomeserverTestCase):
         self._set_canonical_alias(room_id_1, "#Room_Alias1:test", self.admin_user_tok)
 
         def _search_test(
-            expected_room_id: Optional[str],
+            expected_room_id: str | None,
             search_term: str,
             expected_http_code: int = 200,
         ) -> None:
diff --git a/tests/rest/admin/test_scheduled_tasks.py b/tests/rest/admin/test_scheduled_tasks.py
index 16b80e214b..fb275f6d55 100644
--- a/tests/rest/admin/test_scheduled_tasks.py
+++ b/tests/rest/admin/test_scheduled_tasks.py
@@ -13,7 +13,7 @@
 #
 #
 #
-from typing import Mapping, Optional, Tuple
+from typing import Mapping
 
 from twisted.internet.testing import MemoryReactor
 
@@ -42,17 +42,17 @@ class ScheduledTasksAdminApiTestCase(unittest.HomeserverTestCase):
         # create and schedule a few tasks
         async def _test_task(
             task: ScheduledTask,
-        ) -> Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]:
+        ) -> tuple[TaskStatus, JsonMapping | None, str | None]:
             return TaskStatus.ACTIVE, None, None
 
         async def _finished_test_task(
             task: ScheduledTask,
-        ) -> Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]:
+        ) -> tuple[TaskStatus, JsonMapping | None, str | None]:
             return TaskStatus.COMPLETE, None, None
 
         async def _failed_test_task(
             task: ScheduledTask,
-        ) -> Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]:
+        ) -> tuple[TaskStatus, JsonMapping | None, str | None]:
             return TaskStatus.FAILED, None, "Everything failed"
 
         self._task_scheduler.register_action(_test_task, "test_task")
diff --git a/tests/rest/admin/test_server_notice.py b/tests/rest/admin/test_server_notice.py
index ebb6867d7c..5053fea9c9 100644
--- a/tests/rest/admin/test_server_notice.py
+++ b/tests/rest/admin/test_server_notice.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import List, Sequence
+from typing import Sequence
 
 from twisted.internet.testing import MemoryReactor
 
@@ -729,7 +729,7 @@ class ServerNoticeTestCase(unittest.HomeserverTestCase):
 
         return invited_rooms
 
-    def _sync_and_get_messages(self, room_id: str, token: str) -> List[JsonDict]:
+    def _sync_and_get_messages(self, room_id: str, token: str) -> list[JsonDict]:
         """
         Do a sync and get messages of a room.
 
diff --git a/tests/rest/admin/test_statistics.py b/tests/rest/admin/test_statistics.py
index 4026c47a23..3dc7e5dc97 100644
--- a/tests/rest/admin/test_statistics.py
+++ b/tests/rest/admin/test_statistics.py
@@ -19,7 +19,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Dict, List, Optional
 
 from twisted.internet.testing import MemoryReactor
 from twisted.web.resource import Resource
@@ -50,7 +49,7 @@ class UserMediaStatisticsTestCase(unittest.HomeserverTestCase):
 
         self.url = "/_synapse/admin/v1/statistics/users/media"
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         resources = super().create_resource_dict()
         resources["/_matrix/media"] = self.hs.get_media_repository_resource()
         return resources
@@ -485,7 +484,7 @@ class UserMediaStatisticsTestCase(unittest.HomeserverTestCase):
             # Upload some media into the room
             self.helper.upload_media(SMALL_PNG, tok=user_token, expect_code=200)
 
-    def _check_fields(self, content: List[JsonDict]) -> None:
+    def _check_fields(self, content: list[JsonDict]) -> None:
         """Checks that all attributes are present in content
         Args:
             content: List that is checked for content
@@ -497,7 +496,7 @@ class UserMediaStatisticsTestCase(unittest.HomeserverTestCase):
             self.assertIn("media_length", c)
 
     def _order_test(
-        self, order_type: str, expected_user_list: List[str], dir: Optional[str] = None
+        self, order_type: str, expected_user_list: list[str], dir: str | None = None
     ) -> None:
         """Request the list of users in a certain order. Assert that order is what
         we expect
diff --git a/tests/rest/admin/test_user.py b/tests/rest/admin/test_user.py
index ca41cd6c31..6d0584fa63 100644
--- a/tests/rest/admin/test_user.py
+++ b/tests/rest/admin/test_user.py
@@ -27,7 +27,6 @@ import time
 import urllib.parse
 from binascii import unhexlify
 from http import HTTPStatus
-from typing import Dict, List, Optional
 from unittest.mock import AsyncMock, Mock, patch
 
 from parameterized import parameterized, parameterized_class
@@ -643,10 +642,10 @@ class UsersListTestCase(unittest.HomeserverTestCase):
         """Test that searching for a users works correctly"""
 
         def _search_test(
-            expected_user_id: Optional[str],
+            expected_user_id: str | None,
             search_term: str,
-            search_field: Optional[str] = "name",
-            expected_http_code: Optional[int] = 200,
+            search_field: str | None = "name",
+            expected_http_code: int | None = 200,
         ) -> None:
             """Search for a user and check that the returned user's id is a match
 
@@ -1185,7 +1184,7 @@ class UsersListTestCase(unittest.HomeserverTestCase):
         )
 
         def test_user_type(
-            expected_user_ids: List[str], not_user_types: Optional[List[str]] = None
+            expected_user_ids: list[str], not_user_types: list[str] | None = None
         ) -> None:
             """Runs a test for the not_user_types param
             Args:
@@ -1262,7 +1261,7 @@ class UsersListTestCase(unittest.HomeserverTestCase):
         )
 
         def test_user_type(
-            expected_user_ids: List[str], not_user_types: Optional[List[str]] = None
+            expected_user_ids: list[str], not_user_types: list[str] | None = None
         ) -> None:
             """Runs a test for the not_user_types param
             Args:
@@ -1373,9 +1372,9 @@ class UsersListTestCase(unittest.HomeserverTestCase):
 
     def _order_test(
         self,
-        expected_user_list: List[str],
-        order_by: Optional[str],
-        dir: Optional[str] = None,
+        expected_user_list: list[str],
+        order_by: str | None,
+        dir: str | None = None,
     ) -> None:
         """Request the list of users in a certain order. Assert that order is what
         we expect
@@ -1403,7 +1402,7 @@ class UsersListTestCase(unittest.HomeserverTestCase):
         self.assertEqual(expected_user_list, returned_order)
         self._check_fields(channel.json_body["users"])
 
-    def _check_fields(self, content: List[JsonDict]) -> None:
+    def _check_fields(self, content: list[JsonDict]) -> None:
         """Checks that the expected user attributes are present in content
         Args:
             content: List that is checked for content
@@ -3116,7 +3115,7 @@ class UserRestTestCase(unittest.HomeserverTestCase):
         self.assertEqual("@user:test", channel.json_body["name"])
         self.assertTrue(channel.json_body["admin"])
 
-    def set_user_type(self, user_type: Optional[str]) -> None:
+    def set_user_type(self, user_type: str | None) -> None:
         # Set to user_type
         channel = self.make_request(
             "PUT",
@@ -3690,7 +3689,7 @@ class UserMediaRestTestCase(unittest.HomeserverTestCase):
             self.other_user
         )
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         resources = super().create_resource_dict()
         resources["/_matrix/media"] = self.hs.get_media_repository_resource()
         return resources
@@ -4138,7 +4137,7 @@ class UserMediaRestTestCase(unittest.HomeserverTestCase):
             [media2] + sorted([media1, media3]), "safe_from_quarantine", "b"
         )
 
-    def _create_media_for_user(self, user_token: str, number_media: int) -> List[str]:
+    def _create_media_for_user(self, user_token: str, number_media: int) -> list[str]:
         """
         Create a number of media for a specific user
         Args:
@@ -4195,7 +4194,7 @@ class UserMediaRestTestCase(unittest.HomeserverTestCase):
 
         return media_id
 
-    def _check_fields(self, content: List[JsonDict]) -> None:
+    def _check_fields(self, content: list[JsonDict]) -> None:
         """Checks that the expected user attributes are present in content
         Args:
             content: List that is checked for content
@@ -4212,9 +4211,9 @@ class UserMediaRestTestCase(unittest.HomeserverTestCase):
 
     def _order_test(
         self,
-        expected_media_list: List[str],
-        order_by: Optional[str],
-        dir: Optional[str] = None,
+        expected_media_list: list[str],
+        order_by: str | None,
+        dir: str | None = None,
     ) -> None:
         """Request the list of media in a certain order. Assert that order is what
         we expect
diff --git a/tests/rest/admin/test_username_available.py b/tests/rest/admin/test_username_available.py
index b2c1d7ac0a..c3091ce412 100644
--- a/tests/rest/admin/test_username_available.py
+++ b/tests/rest/admin/test_username_available.py
@@ -18,7 +18,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Optional
 
 from twisted.internet.testing import MemoryReactor
 
@@ -44,8 +43,8 @@ class UsernameAvailableTestCase(unittest.HomeserverTestCase):
 
         async def check_username(
             localpart: str,
-            guest_access_token: Optional[str] = None,
-            assigned_user_id: Optional[str] = None,
+            guest_access_token: str | None = None,
+            assigned_user_id: str | None = None,
             inhibit_user_in_use_error: bool = False,
         ) -> None:
             if localpart == "allowed":
diff --git a/tests/rest/client/sliding_sync/test_extension_thread_subscriptions.py b/tests/rest/client/sliding_sync/test_extension_thread_subscriptions.py
index 4e151b9aae..aa251bd78b 100644
--- a/tests/rest/client/sliding_sync/test_extension_thread_subscriptions.py
+++ b/tests/rest/client/sliding_sync/test_extension_thread_subscriptions.py
@@ -13,7 +13,7 @@
 #
 import logging
 from http import HTTPStatus
-from typing import List, Optional, Tuple, cast
+from typing import cast
 
 from twisted.test.proto_helpers import MemoryReactor
 
@@ -358,7 +358,7 @@ class SlidingSyncThreadSubscriptionsExtensionTestCase(SlidingSyncBase):
         using the companion /thread_subscriptions endpoint.
         """
 
-        thread_root_ids: List[str] = []
+        thread_root_ids: list[str] = []
 
         def make_subscription() -> None:
             thread_root_resp = self.helper.send(
@@ -455,7 +455,7 @@ class SlidingSyncThreadSubscriptionsExtensionTestCase(SlidingSyncBase):
 
     def _do_backpaginate(
         self, *, from_tok: str, to_tok: str, limit: int, access_token: str
-    ) -> Tuple[JsonDict, Optional[str]]:
+    ) -> tuple[JsonDict, str | None]:
         channel = self.make_request(
             "GET",
             "/_matrix/client/unstable/io.element.msc4308/thread_subscriptions"
@@ -465,7 +465,7 @@ class SlidingSyncThreadSubscriptionsExtensionTestCase(SlidingSyncBase):
 
         self.assertEqual(channel.code, HTTPStatus.OK, channel.json_body)
         body = channel.json_body
-        return body, cast(Optional[str], body.get("end"))
+        return body, cast(str | None, body.get("end"))
 
     def _subscribe_to_thread(
         self, user_id: str, room_id: str, thread_root_id: str
diff --git a/tests/rest/client/sliding_sync/test_extension_threads.py b/tests/rest/client/sliding_sync/test_extension_threads.py
index eb2d2b4a3e..f4d2204870 100644
--- a/tests/rest/client/sliding_sync/test_extension_threads.py
+++ b/tests/rest/client/sliding_sync/test_extension_threads.py
@@ -19,10 +19,11 @@ import synapse.rest.admin
 from synapse.api.constants import RelationTypes
 from synapse.rest.client import login, relations, room, sync
 from synapse.server import HomeServer
-from synapse.types import JsonDict
+from synapse.types import JsonDict, StreamKeyType
 from synapse.util.clock import Clock
 
 from tests.rest.client.sliding_sync.test_sliding_sync import SlidingSyncBase
+from tests.server import TimedOutException
 
 logger = logging.getLogger(__name__)
 
@@ -134,6 +135,13 @@ class SlidingSyncThreadsExtensionTestCase(SlidingSyncBase):
         # base = self.store.get_max_thread_subscriptions_stream_id()
 
         sync_body = {
+            "lists": {
+                "foo-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [],
+                    "timeline_limit": 0,  # Set to 0, otherwise events will be in timeline, not extension
+                }
+            },
             "extensions": {
                 EXT_NAME: {
                     "enabled": True,
@@ -158,6 +166,13 @@ class SlidingSyncThreadsExtensionTestCase(SlidingSyncBase):
         user1_tok = self.login(user1_id, "pass")
         room_id = self.helper.create_room_as(user1_id, tok=user1_tok)
         sync_body = {
+            "lists": {
+                "foo-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [],
+                    "timeline_limit": 0,
+                }
+            },
             "extensions": {
                 EXT_NAME: {
                     "enabled": True,
@@ -256,6 +271,13 @@ class SlidingSyncThreadsExtensionTestCase(SlidingSyncBase):
 
         # User2 syncs with threads extension enabled
         sync_body = {
+            "lists": {
+                "foo-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [],
+                    "timeline_limit": 0,
+                }
+            },
             "extensions": {
                 EXT_NAME: {
                     "enabled": True,
@@ -273,12 +295,10 @@ class SlidingSyncThreadsExtensionTestCase(SlidingSyncBase):
 
     def test_threads_not_returned_after_leaving_room(self) -> None:
         """
-        Test that thread updates are not returned after a user leaves the room,
-        even if the thread was updated while they were joined.
+        Test that thread updates are properly bounded when a user leaves a room.
 
-        This tests the known limitation: if a thread has multiple updates and the
-        user leaves between them, they won't see any updates (even earlier ones
-        while joined).
+        Users should see thread updates that occurred up to the point they left,
+        but NOT updates that occurred after they left.
         """
         user1_id = self.register_user("user1", "pass")
         user1_tok = self.login(user1_id, "pass")
@@ -296,6 +316,13 @@ class SlidingSyncThreadsExtensionTestCase(SlidingSyncBase):
 
         # Initial sync for user2
         sync_body = {
+            "lists": {
+                "foo-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [],
+                    "timeline_limit": 0,
+                }
+            },
             "extensions": {
                 EXT_NAME: {
                     "enabled": True,
@@ -340,13 +367,33 @@ class SlidingSyncThreadsExtensionTestCase(SlidingSyncBase):
         # User2 incremental sync
         response_body, _ = self.do_sync(sync_body, tok=user2_tok, since=sync_pos)
 
-        # Assert: User2 should NOT see the thread update (they left before latest update)
-        # Note: This also demonstrates that only currently joined rooms are returned - user2
-        # won't see the thread even though there was an update while they were joined (Reply 1)
-        self.assertNotIn(
+        # Assert: User2 SHOULD see Reply 1 (happened while joined) but NOT Reply 2 (after leaving)
+        self.assertIn(
             EXT_NAME,
             response_body["extensions"],
-            "User2 should not see thread updates after leaving the room",
+            "User2 should see thread updates up to the point they left",
+        )
+        self.assertIn(
+            room_id,
+            response_body["extensions"][EXT_NAME]["updates"],
+            "Thread updates should include the room user2 left",
+        )
+        self.assertIn(
+            thread_root,
+            response_body["extensions"][EXT_NAME]["updates"][room_id],
+            "Thread root should be in the updates",
+        )
+
+        # Verify that only a single update was seen (Reply 1) by checking that there's
+        # no prev_batch token. If Reply 2 was also included, there would be multiple
+        # updates and a prev_batch token would be present.
+        thread_update = response_body["extensions"][EXT_NAME]["updates"][room_id][
+            thread_root
+        ]
+        self.assertNotIn(
+            "prev_batch",
+            thread_update,
+            "No prev_batch should be present since only one update (Reply 1) is visible",
         )
 
     def test_threads_with_include_roots_true(self) -> None:
@@ -380,6 +427,13 @@ class SlidingSyncThreadsExtensionTestCase(SlidingSyncBase):
 
         # Sync with include_roots=True
         sync_body = {
+            "lists": {
+                "foo-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [],
+                    "timeline_limit": 0,
+                }
+            },
             "extensions": {
                 EXT_NAME: {
                     "enabled": True,
@@ -434,6 +488,13 @@ class SlidingSyncThreadsExtensionTestCase(SlidingSyncBase):
 
         # Sync with include_roots=False (explicitly)
         sync_body = {
+            "lists": {
+                "foo-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [],
+                    "timeline_limit": 0,
+                }
+            },
             "extensions": {
                 EXT_NAME: {
                     "enabled": True,
@@ -451,6 +512,13 @@ class SlidingSyncThreadsExtensionTestCase(SlidingSyncBase):
 
         # Also test with include_roots omitted (should behave the same)
         sync_body_no_param = {
+            "lists": {
+                "foo-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [],
+                    "timeline_limit": 0,
+                }
+            },
             "extensions": {
                 EXT_NAME: {
                     "enabled": True,
@@ -478,6 +546,13 @@ class SlidingSyncThreadsExtensionTestCase(SlidingSyncBase):
 
         # Initial sync to establish baseline
         sync_body = {
+            "lists": {
+                "foo-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [],
+                    "timeline_limit": 0,
+                }
+            },
             "extensions": {
                 EXT_NAME: {
                     "enabled": True,
@@ -529,6 +604,13 @@ class SlidingSyncThreadsExtensionTestCase(SlidingSyncBase):
 
         # Initial sync to establish baseline
         sync_body = {
+            "lists": {
+                "foo-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [],
+                    "timeline_limit": 0,
+                }
+            },
             "extensions": {
                 EXT_NAME: {
                     "enabled": True,
@@ -668,6 +750,13 @@ class SlidingSyncThreadsExtensionTestCase(SlidingSyncBase):
 
         # Initial sync (no from_token)
         sync_body = {
+            "lists": {
+                "foo-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [],
+                    "timeline_limit": 0,
+                }
+            },
             "extensions": {
                 EXT_NAME: {
                     "enabled": True,
@@ -873,6 +962,13 @@ class SlidingSyncThreadsExtensionTestCase(SlidingSyncBase):
 
         # Do initial sync with threads extension enabled and limit=2
         sync_body = {
+            "lists": {
+                "all-rooms": {
+                    "ranges": [[0, 10]],
+                    "required_state": [],
+                    "timeline_limit": 0,
+                }
+            },
             "extensions": {
                 EXT_NAME: {
                     "enabled": True,
@@ -894,9 +990,10 @@ class SlidingSyncThreadsExtensionTestCase(SlidingSyncBase):
         # Use prev_batch with /thread_updates endpoint to get remaining updates
         # Note: prev_batch should be used as 'from' parameter (upper bound for backward pagination)
         channel = self.make_request(
-            "GET",
+            "POST",
             f"/_matrix/client/unstable/io.element.msc4360/thread_updates?dir=b&from={prev_batch}",
             access_token=user1_tok,
+            content={},
         )
         self.assertEqual(channel.code, 200)
 
@@ -958,6 +1055,13 @@ class SlidingSyncThreadsExtensionTestCase(SlidingSyncBase):
 
         # First sync
         sync_body = {
+            "lists": {
+                "all-rooms": {
+                    "ranges": [[0, 10]],
+                    "required_state": [],
+                    "timeline_limit": 0,
+                }
+            },
             "extensions": {
                 EXT_NAME: {
                     "enabled": True,
@@ -996,6 +1100,13 @@ class SlidingSyncThreadsExtensionTestCase(SlidingSyncBase):
 
         # Second sync with limit=1 to get only some of the new threads
         sync_body_with_limit = {
+            "lists": {
+                "all-rooms": {
+                    "ranges": [[0, 10]],
+                    "required_state": [],
+                    "timeline_limit": 0,
+                }
+            },
             "extensions": {
                 EXT_NAME: {
                     "enabled": True,
@@ -1020,9 +1131,10 @@ class SlidingSyncThreadsExtensionTestCase(SlidingSyncBase):
         # Now use /thread_updates with from=prev_batch and to=pos1
         # This should get the 2 remaining new threads (created after pos1, not returned in second sync)
         channel = self.make_request(
-            "GET",
+            "POST",
             f"/_matrix/client/unstable/io.element.msc4360/thread_updates?dir=b&from={prev_batch}&to={pos1}",
             access_token=user1_tok,
+            content={},
         )
         self.assertEqual(channel.code, 200)
 
@@ -1055,3 +1167,243 @@ class SlidingSyncThreadsExtensionTestCase(SlidingSyncBase):
             all_new_threads,
             "Combined responses should include all new thread updates with no gaps",
         )
+
+    def test_threads_only_from_rooms_in_list(self) -> None:
+        """
+        Test that thread updates are only returned for rooms that are in the
+        sliding sync response, not from all rooms the user is joined to.
+
+        This tests the scenario where a user is joined to multiple rooms but
+        the room list range/limit means only some rooms are in the response.
+        """
+        user1_id = self.register_user("user1", "pass")
+        user1_tok = self.login(user1_id, "pass")
+
+        # Create three rooms
+        room_a_id = self.helper.create_room_as(user1_id, tok=user1_tok)
+        room_b_id = self.helper.create_room_as(user1_id, tok=user1_tok)
+        room_c_id = self.helper.create_room_as(user1_id, tok=user1_tok)
+
+        # Create threads in all three rooms
+        thread_a_root = self.helper.send(room_a_id, body="Thread A", tok=user1_tok)[
+            "event_id"
+        ]
+        thread_b_root = self.helper.send(room_b_id, body="Thread B", tok=user1_tok)[
+            "event_id"
+        ]
+        thread_c_root = self.helper.send(room_c_id, body="Thread C", tok=user1_tok)[
+            "event_id"
+        ]
+
+        # Do an initial sync to get the sync position and see room ordering
+        initial_sync_body = {
+            "lists": {
+                "all-rooms": {
+                    "ranges": [[0, 2]],
+                    "required_state": [],
+                    "timeline_limit": 0,
+                }
+            },
+        }
+        response_body, sync_pos = self.do_sync(initial_sync_body, tok=user1_tok)
+
+        # Add replies to all threads after the initial sync
+        self.helper.send_event(
+            room_a_id,
+            type="m.room.message",
+            content={
+                "msgtype": "m.text",
+                "body": "Reply to A",
+                "m.relates_to": {
+                    "rel_type": RelationTypes.THREAD,
+                    "event_id": thread_a_root,
+                },
+            },
+            tok=user1_tok,
+        )
+        self.helper.send_event(
+            room_b_id,
+            type="m.room.message",
+            content={
+                "msgtype": "m.text",
+                "body": "Reply to B",
+                "m.relates_to": {
+                    "rel_type": RelationTypes.THREAD,
+                    "event_id": thread_b_root,
+                },
+            },
+            tok=user1_tok,
+        )
+        self.helper.send_event(
+            room_c_id,
+            type="m.room.message",
+            content={
+                "msgtype": "m.text",
+                "body": "Reply to C",
+                "m.relates_to": {
+                    "rel_type": RelationTypes.THREAD,
+                    "event_id": thread_c_root,
+                },
+            },
+            tok=user1_tok,
+        )
+
+        # Now do a sync with a limited range that excludes the last room
+        sync_body = {
+            "lists": {
+                "limited-list": {
+                    "ranges": [[0, 1]],  # Only include first 2 rooms
+                    "required_state": [],
+                    "timeline_limit": 0,
+                }
+            },
+            "extensions": {
+                EXT_NAME: {
+                    "enabled": True,
+                }
+            },
+        }
+        response_body, _ = self.do_sync(sync_body, tok=user1_tok, since=sync_pos)
+
+        # Get which rooms were included in this limited response
+        included_rooms = set(
+            response_body["lists"]["limited-list"]["ops"][0]["room_ids"]
+        )
+        excluded_room = ({room_a_id, room_b_id, room_c_id} - included_rooms).pop()
+
+        # Assert: Only threads from rooms in the response should be included
+        thread_updates = response_body["extensions"][EXT_NAME]["updates"]
+
+        # Check that included rooms have thread updates
+        for room_id in included_rooms:
+            self.assertIn(
+                room_id,
+                thread_updates,
+                f"Room {room_id} should have thread updates since it's in the room list",
+            )
+
+        # Check that the excluded room is NOT present
+        self.assertNotIn(
+            excluded_room,
+            thread_updates,
+            f"Room {excluded_room} should NOT have thread updates since it's excluded from the room list",
+        )
+
+    def test_wait_for_new_data(self) -> None:
+        """
+        Test to make sure that the Sliding Sync request waits for new data to arrive.
+
+        (Only applies to incremental syncs with a `timeout` specified)
+        """
+        user1_id = self.register_user("user1", "pass")
+        user1_tok = self.login(user1_id, "pass")
+        user2_id = self.register_user("user2", "pass")
+        user2_tok = self.login(user2_id, "pass")
+
+        room_id = self.helper.create_room_as(user2_id, tok=user2_tok)
+        self.helper.join(room_id, user1_id, tok=user1_tok)
+
+        # Create a thread
+        thread_root = self.helper.send(room_id, body="Thread root", tok=user1_tok)[
+            "event_id"
+        ]
+
+        sync_body = {
+            "lists": {},
+            "room_subscriptions": {
+                room_id: {
+                    "required_state": [],
+                    "timeline_limit": 0,
+                },
+            },
+            "extensions": {
+                EXT_NAME: {
+                    "enabled": True,
+                }
+            },
+        }
+        _, from_token = self.do_sync(sync_body, tok=user1_tok)
+
+        # Make an incremental Sliding Sync request with the threads extension enabled
+        channel = self.make_request(
+            "POST",
+            self.sync_endpoint + f"?timeout=10000&pos={from_token}",
+            content=sync_body,
+            access_token=user1_tok,
+            await_result=False,
+        )
+        # Block for 5 seconds to make sure we are `notifier.wait_for_events(...)`
+        with self.assertRaises(TimedOutException):
+            channel.await_result(timeout_ms=5000)
+        # Send a thread reply to trigger new results
+        self.helper.send_event(
+            room_id,
+            type="m.room.message",
+            content={
+                "msgtype": "m.text",
+                "body": "Reply in thread",
+                "m.relates_to": {
+                    "rel_type": RelationTypes.THREAD,
+                    "event_id": thread_root,
+                },
+            },
+            tok=user2_tok,
+        )
+        # Should respond before the 10 second timeout
+        channel.await_result(timeout_ms=3000)
+        self.assertEqual(channel.code, 200, channel.json_body)
+
+        # We should see the new thread update
+        self.assertIn(
+            thread_root,
+            channel.json_body["extensions"][EXT_NAME]["updates"][room_id],
+        )
+
+    def test_wait_for_new_data_timeout(self) -> None:
+        """
+        Test to make sure that the Sliding Sync request waits for new data to arrive but
+        no data ever arrives so we timeout. We're also making sure that the default data
+        from the threads extension doesn't trigger a false-positive for new data.
+        """
+        user1_id = self.register_user("user1", "pass")
+        user1_tok = self.login(user1_id, "pass")
+
+        sync_body = {
+            "lists": {},
+            "extensions": {
+                EXT_NAME: {
+                    "enabled": True,
+                }
+            },
+        }
+        _, from_token = self.do_sync(sync_body, tok=user1_tok)
+
+        # Make the Sliding Sync request
+        channel = self.make_request(
+            "POST",
+            self.sync_endpoint + f"?timeout=10000&pos={from_token}",
+            content=sync_body,
+            access_token=user1_tok,
+            await_result=False,
+        )
+        # Block for 5 seconds to make sure we are `notifier.wait_for_events(...)`
+        with self.assertRaises(TimedOutException):
+            channel.await_result(timeout_ms=5000)
+        # Wake-up `notifier.wait_for_events(...)` that will cause us test
+        # `SlidingSyncResult.__bool__` for new results.
+        self._bump_notifier_wait_for_events(
+            user1_id, wake_stream_key=StreamKeyType.ACCOUNT_DATA
+        )
+        # Block for a little bit more to ensure we don't see any new results.
+        with self.assertRaises(TimedOutException):
+            channel.await_result(timeout_ms=4000)
+        # Wait for the sync to complete (wait for the rest of the 10 second timeout,
+        # 5000 + 4000 + 1200 > 10000)
+        channel.await_result(timeout_ms=1200)
+        self.assertEqual(channel.code, 200, channel.json_body)
+
+        # Should be no thread updates
+        self.assertNotIn(
+            EXT_NAME,
+            channel.json_body.get("extensions", {}),
+        )
diff --git a/tests/rest/client/sliding_sync/test_extension_to_device.py b/tests/rest/client/sliding_sync/test_extension_to_device.py
index a77b0a2e9f..0b0a65babf 100644
--- a/tests/rest/client/sliding_sync/test_extension_to_device.py
+++ b/tests/rest/client/sliding_sync/test_extension_to_device.py
@@ -12,7 +12,6 @@
 # <https://www.gnu.org/licenses/agpl-3.0.html>.
 #
 import logging
-from typing import List
 
 from parameterized import parameterized_class
 
@@ -59,7 +58,7 @@ class SlidingSyncToDeviceExtensionTestCase(SlidingSyncBase):
         super().prepare(reactor, clock, hs)
 
     def _assert_to_device_response(
-        self, response_body: JsonDict, expected_messages: List[JsonDict]
+        self, response_body: JsonDict, expected_messages: list[JsonDict]
     ) -> str:
         """Assert the sliding sync response was successful and has the expected
         to-device messages.
diff --git a/tests/rest/client/sliding_sync/test_rooms_timeline.py b/tests/rest/client/sliding_sync/test_rooms_timeline.py
index 44a6068c11..bc23776326 100644
--- a/tests/rest/client/sliding_sync/test_rooms_timeline.py
+++ b/tests/rest/client/sliding_sync/test_rooms_timeline.py
@@ -12,7 +12,6 @@
 # <https://www.gnu.org/licenses/agpl-3.0.html>.
 #
 import logging
-from typing import List, Optional
 
 from parameterized import parameterized_class
 
@@ -66,7 +65,7 @@ class SlidingSyncRoomsTimelineTestCase(SlidingSyncBase):
         self,
         actual_items: StrSequence,
         expected_items: StrSequence,
-        message: Optional[str] = None,
+        message: str | None = None,
     ) -> None:
         """
         Like `self.assertListEqual(...)` but with an actually understandable diff message.
@@ -75,14 +74,14 @@ class SlidingSyncRoomsTimelineTestCase(SlidingSyncBase):
         if actual_items == expected_items:
             return
 
-        expected_lines: List[str] = []
+        expected_lines: list[str] = []
         for expected_item in expected_items:
             is_expected_in_actual = expected_item in actual_items
             expected_lines.append(
                 "{}  {}".format(" " if is_expected_in_actual else "?", expected_item)
             )
 
-        actual_lines: List[str] = []
+        actual_lines: list[str] = []
         for actual_item in actual_items:
             is_actual_in_expected = actual_item in expected_items
             actual_lines.append(
@@ -101,9 +100,9 @@ class SlidingSyncRoomsTimelineTestCase(SlidingSyncBase):
         self,
         *,
         room_id: str,
-        actual_event_ids: List[str],
-        expected_event_ids: List[str],
-        message: Optional[str] = None,
+        actual_event_ids: list[str],
+        expected_event_ids: list[str],
+        message: str | None = None,
     ) -> None:
         """
         Like `self.assertListEqual(...)` for event IDs in a room but will give a nicer
diff --git a/tests/rest/client/sliding_sync/test_sliding_sync.py b/tests/rest/client/sliding_sync/test_sliding_sync.py
index 8da5863b3a..c27a712088 100644
--- a/tests/rest/client/sliding_sync/test_sliding_sync.py
+++ b/tests/rest/client/sliding_sync/test_sliding_sync.py
@@ -12,7 +12,7 @@
 # <https://www.gnu.org/licenses/agpl-3.0.html>.
 #
 import logging
-from typing import Any, Dict, Iterable, List, Literal, Optional, Tuple
+from typing import Any, Iterable, Literal
 from unittest.mock import AsyncMock
 
 from parameterized import parameterized, parameterized_class
@@ -81,8 +81,8 @@ class SlidingSyncBase(unittest.HomeserverTestCase):
         return config
 
     def do_sync(
-        self, sync_body: JsonDict, *, since: Optional[str] = None, tok: str
-    ) -> Tuple[JsonDict, str]:
+        self, sync_body: JsonDict, *, since: str | None = None, tok: str
+    ) -> tuple[JsonDict, str]:
         """Do a sliding sync request with given body.
 
         Asserts the request was successful.
@@ -170,7 +170,7 @@ class SlidingSyncBase(unittest.HomeserverTestCase):
         # Scrutinize the account data since it has no concrete type. We're just copying
         # everything into a known type. It should be a mapping from user ID to a list of
         # room IDs. Ignore anything else.
-        new_dm_map: Dict[str, List[str]] = {}
+        new_dm_map: dict[str, list[str]] = {}
         if isinstance(existing_dm_map, dict):
             for user_id, room_ids in existing_dm_map.items():
                 if isinstance(user_id, str) and isinstance(room_ids, list):
@@ -239,8 +239,8 @@ class SlidingSyncBase(unittest.HomeserverTestCase):
     def _create_remote_invite_room_for_user(
         self,
         invitee_user_id: str,
-        unsigned_invite_room_state: Optional[List[StrippedStateEvent]],
-        invite_room_id: Optional[str] = None,
+        unsigned_invite_room_state: list[StrippedStateEvent] | None,
+        invite_room_id: str | None = None,
     ) -> str:
         """
         Create a fake invite for a remote room and persist it.
diff --git a/tests/rest/client/test_account.py b/tests/rest/client/test_account.py
index 773f49dfc9..ffa96c7840 100644
--- a/tests/rest/client/test_account.py
+++ b/tests/rest/client/test_account.py
@@ -23,7 +23,7 @@ import os
 import re
 from email.parser import Parser
 from http import HTTPStatus
-from typing import Any, Dict, List, Optional, Union
+from typing import Any
 from unittest.mock import Mock
 
 from twisted.internet.interfaces import IReactorTCP
@@ -87,7 +87,7 @@ class PasswordResetTestCase(unittest.HomeserverTestCase):
         ) -> None:
             self.email_attempts.append(msg_bytes)
 
-        self.email_attempts: List[bytes] = []
+        self.email_attempts: list[bytes] = []
         hs.get_send_email_handler()._sendmail = sendmail
 
         return hs
@@ -363,7 +363,7 @@ class PasswordResetTestCase(unittest.HomeserverTestCase):
         email: str,
         client_secret: str,
         ip: str = "127.0.0.1",
-        next_link: Optional[str] = None,
+        next_link: str | None = None,
     ) -> str:
         body = {"client_secret": client_secret, "email": email, "send_attempt": 1}
         if next_link is not None:
@@ -384,7 +384,7 @@ class PasswordResetTestCase(unittest.HomeserverTestCase):
 
         return channel.json_body["sid"]
 
-    def _validate_token(self, link: str, next_link: Optional[str] = None) -> None:
+    def _validate_token(self, link: str, next_link: str | None = None) -> None:
         # Remove the host
         path = link.replace("https://example.com", "")
 
@@ -721,7 +721,7 @@ class WhoamiTestCase(unittest.HomeserverTestCase):
         register.register_servlets,
     ]
 
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         config = super().default_config()
         config["allow_guest_access"] = True
         return config
@@ -827,7 +827,7 @@ class ThreepidEmailRestTestCase(unittest.HomeserverTestCase):
         ) -> None:
             self.email_attempts.append(msg_bytes)
 
-        self.email_attempts: List[bytes] = []
+        self.email_attempts: list[bytes] = []
         self.hs.get_send_email_handler()._sendmail = sendmail
 
         return self.hs
@@ -1152,9 +1152,9 @@ class ThreepidEmailRestTestCase(unittest.HomeserverTestCase):
         self,
         email: str,
         client_secret: str,
-        next_link: Optional[str] = None,
+        next_link: str | None = None,
         expect_code: int = HTTPStatus.OK,
-    ) -> Optional[str]:
+    ) -> str | None:
         """Request a validation token to add an email address to a user's account
 
         Args:
@@ -1201,7 +1201,9 @@ class ThreepidEmailRestTestCase(unittest.HomeserverTestCase):
         self.assertEqual(
             HTTPStatus.BAD_REQUEST, channel.code, msg=channel.result["body"]
         )
-        self.assertEqual(expected_errcode, channel.json_body["errcode"])
+        self.assertEqual(
+            expected_errcode, channel.json_body["errcode"], msg=channel.result["body"]
+        )
         self.assertIn(expected_error, channel.json_body["error"])
 
     def _validate_token(self, link: str) -> None:
@@ -1392,10 +1394,10 @@ class AccountStatusTestCase(unittest.HomeserverTestCase):
         async def post_json(
             destination: str,
             path: str,
-            data: Optional[JsonDict] = None,
+            data: JsonDict | None = None,
             *a: Any,
             **kwa: Any,
-        ) -> Union[JsonDict, list]:
+        ) -> JsonDict | list:
             if destination == "remote":
                 return {
                     "account_statuses": {
@@ -1501,11 +1503,11 @@ class AccountStatusTestCase(unittest.HomeserverTestCase):
 
     def _test_status(
         self,
-        users: Optional[List[str]],
+        users: list[str] | None,
         expected_status_code: int = HTTPStatus.OK,
-        expected_statuses: Optional[Dict[str, Dict[str, bool]]] = None,
-        expected_failures: Optional[List[str]] = None,
-        expected_errcode: Optional[str] = None,
+        expected_statuses: dict[str, dict[str, bool]] | None = None,
+        expected_failures: list[str] | None = None,
+        expected_errcode: str | None = None,
     ) -> None:
         """Send a request to the account status endpoint and check that the response
         matches with what's expected.
diff --git a/tests/rest/client/test_auth.py b/tests/rest/client/test_auth.py
index f5b7f95721..ffaf0e5a32 100644
--- a/tests/rest/client/test_auth.py
+++ b/tests/rest/client/test_auth.py
@@ -20,7 +20,7 @@
 #
 import re
 from http import HTTPStatus
-from typing import Any, Dict, List, Optional, Tuple, Union
+from typing import Any
 
 from twisted.internet.defer import succeed
 from twisted.internet.testing import MemoryReactor
@@ -47,7 +47,7 @@ from tests.unittest import override_config, skip_unless
 class DummyRecaptchaChecker(UserInteractiveAuthChecker):
     def __init__(self, hs: HomeServer) -> None:
         super().__init__(hs)
-        self.recaptcha_attempts: List[Tuple[dict, str]] = []
+        self.recaptcha_attempts: list[tuple[dict, str]] = []
 
     def is_enabled(self) -> bool:
         return True
@@ -90,7 +90,7 @@ class FallbackAuthTests(unittest.HomeserverTestCase):
         self,
         session: str,
         expected_post_response: int,
-        post_session: Optional[str] = None,
+        post_session: str | None = None,
     ) -> None:
         """Get and respond to a fallback recaptcha. Returns the second request."""
         if post_session is None:
@@ -178,7 +178,7 @@ class UIAuthTests(unittest.HomeserverTestCase):
         register.register_servlets,
     ]
 
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         config = super().default_config()
 
         # public_baseurl uses an http:// scheme because FakeChannel.isSecure() returns
@@ -195,7 +195,7 @@ class UIAuthTests(unittest.HomeserverTestCase):
 
         return config
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         resource_dict = super().create_resource_dict()
         resource_dict.update(build_synapse_client_resource_tree(self.hs))
         return resource_dict
@@ -220,7 +220,7 @@ class UIAuthTests(unittest.HomeserverTestCase):
         access_token: str,
         device: str,
         expected_response: int,
-        body: Union[bytes, JsonDict] = b"",
+        body: bytes | JsonDict = b"",
     ) -> FakeChannel:
         """Delete an individual device."""
         channel = self.make_request(
@@ -1091,7 +1091,7 @@ class RefreshAuthTests(unittest.HomeserverTestCase):
         was very slow if a lot of refreshes had been performed for the session.
         """
 
-        def _refresh(refresh_token: str) -> Tuple[str, str]:
+        def _refresh(refresh_token: str) -> tuple[str, str]:
             """
             Performs one refresh, returning the next refresh token and access token.
             """
@@ -1172,7 +1172,7 @@ class RefreshAuthTests(unittest.HomeserverTestCase):
 
 def oidc_config(
     id: str, with_localpart_template: bool, **kwargs: Any
-) -> Dict[str, Any]:
+) -> dict[str, Any]:
     """Sample OIDC provider config used in backchannel logout tests.
 
     Args:
@@ -1185,7 +1185,7 @@ def oidc_config(
         A dict suitable for the `oidc_config` or the `oidc_providers[]` parts of
         the HS config
     """
-    config: Dict[str, Any] = {
+    config: dict[str, Any] = {
         "idp_id": id,
         "idp_name": id,
         "issuer": TEST_OIDC_ISSUER,
@@ -1213,7 +1213,7 @@ class OidcBackchannelLogoutTests(unittest.HomeserverTestCase):
         login.register_servlets,
     ]
 
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         config = super().default_config()
 
         # public_baseurl uses an http:// scheme because FakeChannel.isSecure() returns
@@ -1223,7 +1223,7 @@ class OidcBackchannelLogoutTests(unittest.HomeserverTestCase):
 
         return config
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         resource_dict = super().create_resource_dict()
         resource_dict.update(build_synapse_client_resource_tree(self.hs))
         return resource_dict
@@ -1363,7 +1363,7 @@ class OidcBackchannelLogoutTests(unittest.HomeserverTestCase):
         # We should have a user_mapping_session cookie
         cookie_headers = channel.headers.getRawHeaders("Set-Cookie")
         assert cookie_headers
-        cookies: Dict[str, str] = {}
+        cookies: dict[str, str] = {}
         for h in cookie_headers:
             key, value = h.split(";")[0].split("=", maxsplit=1)
             cookies[key] = value
diff --git a/tests/rest/client/test_delayed_events.py b/tests/rest/client/test_delayed_events.py
index 221a4902f2..c67ffc7668 100644
--- a/tests/rest/client/test_delayed_events.py
+++ b/tests/rest/client/test_delayed_events.py
@@ -15,7 +15,6 @@
 """Tests REST events for /delayed_events paths."""
 
 from http import HTTPStatus
-from typing import List
 
 from parameterized import parameterized
 
@@ -574,7 +573,7 @@ class DelayedEventsTestCase(HomeserverTestCase):
         )
         self.assertEqual(setter_expected, content.get(setter_key), content)
 
-    def _get_delayed_events(self) -> List[JsonDict]:
+    def _get_delayed_events(self) -> list[JsonDict]:
         channel = self.make_request(
             "GET",
             PATH_PREFIX,
diff --git a/tests/rest/client/test_devices.py b/tests/rest/client/test_devices.py
index de80b7c186..93dff77d80 100644
--- a/tests/rest/client/test_devices.py
+++ b/tests/rest/client/test_devices.py
@@ -533,16 +533,6 @@ class MSC4190AppserviceDevicesTestCase(unittest.HomeserverTestCase):
         )
         self.assertEqual(channel.code, 200, channel.json_body)
 
-        # On the regular service, that API should not allow for the
-        # creation of new devices.
-        channel = self.make_request(
-            "PUT",
-            "/_matrix/client/v3/devices/AABBCCDD?user_id=@bob:test",
-            content={"display_name": "Bob's device"},
-            access_token=self.pre_msc_service.token,
-        )
-        self.assertEqual(channel.code, 404, channel.json_body)
-
     def test_DELETE_device(self) -> None:
         self.register_appservice_user(
             "alice", self.msc4190_service.token, inhibit_login=True
diff --git a/tests/rest/client/test_keys.py b/tests/rest/client/test_keys.py
index d9a210b616..817edfb8d3 100644
--- a/tests/rest/client/test_keys.py
+++ b/tests/rest/client/test_keys.py
@@ -40,6 +40,147 @@ from tests.unittest import override_config
 from tests.utils import HAS_AUTHLIB
 
 
+class KeyUploadTestCase(unittest.HomeserverTestCase):
+    servlets = [
+        keys.register_servlets,
+        admin.register_servlets_for_client_rest_resource,
+        login.register_servlets,
+    ]
+
+    def test_upload_keys_fails_on_invalid_structure(self) -> None:
+        """Check that we validate the structure of keys upon upload.
+
+        Regression test for https://github.com/element-hq/synapse/pull/17097
+        """
+        self.register_user("alice", "wonderland")
+        alice_token = self.login("alice", "wonderland")
+
+        channel = self.make_request(
+            "POST",
+            "/_matrix/client/v3/keys/upload",
+            {
+                # Error: device_keys must be a dict
+                "device_keys": ["some", "stuff", "weewoo"]
+            },
+            alice_token,
+        )
+        self.assertEqual(channel.code, HTTPStatus.BAD_REQUEST, channel.result)
+        self.assertEqual(
+            channel.json_body["errcode"],
+            Codes.BAD_JSON,
+            channel.result,
+        )
+
+        channel = self.make_request(
+            "POST",
+            "/_matrix/client/v3/keys/upload",
+            {
+                # Error: properties of fallback_keys must be in the form `<algorithm>:<device_id>`
+                "fallback_keys": {"invalid_key": "signature_base64"}
+            },
+            alice_token,
+        )
+        self.assertEqual(channel.code, HTTPStatus.BAD_REQUEST, channel.result)
+        self.assertEqual(
+            channel.json_body["errcode"],
+            Codes.BAD_JSON,
+            channel.result,
+        )
+
+        channel = self.make_request(
+            "POST",
+            "/_matrix/client/v3/keys/upload",
+            {
+                # Same as above, but for one_time_keys
+                "one_time_keys": {"invalid_key": "signature_base64"}
+            },
+            alice_token,
+        )
+        self.assertEqual(channel.code, HTTPStatus.BAD_REQUEST, channel.result)
+        self.assertEqual(
+            channel.json_body["errcode"],
+            Codes.BAD_JSON,
+            channel.result,
+        )
+
+    def test_upload_keys_fails_on_invalid_user_id_or_device_id(self) -> None:
+        """
+        Validate that the requesting user is uploading their own keys and nobody
+        else's.
+        """
+        device_id = "DEVICE_ID"
+        alice_user_id = self.register_user("alice", "wonderland")
+        alice_token = self.login("alice", "wonderland", device_id=device_id)
+
+        channel = self.make_request(
+            "POST",
+            "/_matrix/client/v3/keys/upload",
+            {
+                "device_keys": {
+                    # Included `user_id` does not match requesting user.
+                    "user_id": "@unknown_user:test",
+                    "device_id": device_id,
+                    "algorithms": ["m.olm.curve25519-aes-sha2"],
+                    "keys": {
+                        f"ed25519:{device_id}": "publickey",
+                    },
+                    "signatures": {},
+                }
+            },
+            alice_token,
+        )
+        self.assertEqual(channel.code, HTTPStatus.BAD_REQUEST, channel.result)
+        self.assertEqual(
+            channel.json_body["errcode"],
+            Codes.BAD_JSON,
+            channel.result,
+        )
+
+        channel = self.make_request(
+            "POST",
+            "/_matrix/client/v3/keys/upload",
+            {
+                "device_keys": {
+                    "user_id": alice_user_id,
+                    # Included `device_id` does not match requesting user's.
+                    "device_id": "UNKNOWN_DEVICE_ID",
+                    "algorithms": ["m.olm.curve25519-aes-sha2"],
+                    "keys": {
+                        f"ed25519:{device_id}": "publickey",
+                    },
+                    "signatures": {},
+                }
+            },
+            alice_token,
+        )
+        self.assertEqual(channel.code, HTTPStatus.BAD_REQUEST, channel.result)
+        self.assertEqual(
+            channel.json_body["errcode"],
+            Codes.BAD_JSON,
+            channel.result,
+        )
+
+    def test_upload_keys_succeeds_when_fields_are_explicitly_set_to_null(self) -> None:
+        """
+        This is a regression test for https://github.com/element-hq/synapse/pull/19023.
+        """
+        device_id = "DEVICE_ID"
+        self.register_user("alice", "wonderland")
+        alice_token = self.login("alice", "wonderland", device_id=device_id)
+
+        channel = self.make_request(
+            "POST",
+            "/_matrix/client/v3/keys/upload",
+            {
+                "device_keys": None,
+                "one_time_keys": None,
+                "fallback_keys": None,
+            },
+            alice_token,
+        )
+        self.assertEqual(channel.code, HTTPStatus.OK, channel.result)
+
+
 class KeyQueryTestCase(unittest.HomeserverTestCase):
     servlets = [
         keys.register_servlets,
diff --git a/tests/rest/client/test_login.py b/tests/rest/client/test_login.py
index c54e409a6c..d599351df7 100644
--- a/tests/rest/client/test_login.py
+++ b/tests/rest/client/test_login.py
@@ -25,12 +25,7 @@ from typing import (
     BinaryIO,
     Callable,
     Collection,
-    Dict,
-    List,
     Literal,
-    Optional,
-    Tuple,
-    Union,
 )
 from unittest.mock import Mock
 from urllib.parse import urlencode
@@ -144,14 +139,11 @@ class TestSpamChecker:
     async def check_login_for_spam(
         self,
         user_id: str,
-        device_id: Optional[str],
-        initial_display_name: Optional[str],
-        request_info: Collection[Tuple[Optional[str], str]],
-        auth_provider_id: Optional[str] = None,
-    ) -> Union[
-        Literal["NOT_SPAM"],
-        Tuple["synapse.module_api.errors.Codes", JsonDict],
-    ]:
+        device_id: str | None,
+        initial_display_name: str | None,
+        request_info: Collection[tuple[str | None, str]],
+        auth_provider_id: str | None = None,
+    ) -> Literal["NOT_SPAM"] | tuple["synapse.module_api.errors.Codes", JsonDict]:
         return "NOT_SPAM"
 
 
@@ -168,14 +160,11 @@ class DenyAllSpamChecker:
     async def check_login_for_spam(
         self,
         user_id: str,
-        device_id: Optional[str],
-        initial_display_name: Optional[str],
-        request_info: Collection[Tuple[Optional[str], str]],
-        auth_provider_id: Optional[str] = None,
-    ) -> Union[
-        Literal["NOT_SPAM"],
-        Tuple["synapse.module_api.errors.Codes", JsonDict],
-    ]:
+        device_id: str | None,
+        initial_display_name: str | None,
+        request_info: Collection[tuple[str | None, str]],
+        auth_provider_id: str | None = None,
+    ) -> Literal["NOT_SPAM"] | tuple["synapse.module_api.errors.Codes", JsonDict]:
         # Return an odd set of values to ensure that they get correctly passed
         # to the client.
         return Codes.LIMIT_EXCEEDED, {"extra": "value"}
@@ -633,7 +622,7 @@ class MultiSSOTestCase(unittest.HomeserverTestCase):
         login.register_servlets,
     ]
 
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         config = super().default_config()
 
         config["public_baseurl"] = PUBLIC_BASEURL
@@ -678,7 +667,7 @@ class MultiSSOTestCase(unittest.HomeserverTestCase):
     def prepare(self, reactor: MemoryReactor, clock: Clock, hs: HomeServer) -> None:
         self.login_sso_redirect_url_builder = LoginSSORedirectURIBuilder(hs.config)
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         d = super().create_resource_dict()
         d.update(build_synapse_client_resource_tree(self.hs))
         return d
@@ -730,7 +719,7 @@ class MultiSSOTestCase(unittest.HomeserverTestCase):
         p.close()
 
         # there should be a link for each href
-        returned_idps: List[str] = []
+        returned_idps: list[str] = []
         for link in p.links:
             path, query = link.split("?", 1)
             self.assertEqual(path, "pick_idp")
@@ -891,7 +880,7 @@ class MultiSSOTestCase(unittest.HomeserverTestCase):
         # ... and should have set a cookie including the redirect url
         cookie_headers = channel.headers.getRawHeaders("Set-Cookie")
         assert cookie_headers
-        cookies: Dict[str, str] = {}
+        cookies: dict[str, str] = {}
         for h in cookie_headers:
             key, value = h.split(";")[0].split("=", maxsplit=1)
             cookies[key] = value
@@ -987,7 +976,7 @@ class MultiSSOTestCase(unittest.HomeserverTestCase):
         # it should redirect us to the auth page of the OIDC server
         self.assertEqual(oidc_uri_path, fake_oidc_server.authorization_endpoint)
 
-    def _make_sso_redirect_request(self, idp_prov: Optional[str] = None) -> FakeChannel:
+    def _make_sso_redirect_request(self, idp_prov: str | None = None) -> FakeChannel:
         """Send a request to /_matrix/client/r0/login/sso/redirect
 
         ... possibly specifying an IDP provider
@@ -1179,7 +1168,7 @@ class JWTTestCase(unittest.HomeserverTestCase):
         "algorithm": jwt_algorithm,
     }
 
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         config = super().default_config()
 
         # If jwt_config has been defined (eg via @override_config), don't replace it.
@@ -1188,7 +1177,7 @@ class JWTTestCase(unittest.HomeserverTestCase):
 
         return config
 
-    def jwt_encode(self, payload: Dict[str, Any], secret: str = jwt_secret) -> str:
+    def jwt_encode(self, payload: dict[str, Any], secret: str = jwt_secret) -> str:
         header = {"alg": self.jwt_algorithm}
         result: bytes = jwt.encode(header, payload, secret)
         return result.decode("ascii")
@@ -1426,7 +1415,7 @@ class JWTPubKeyTestCase(unittest.HomeserverTestCase):
         ]
     )
 
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         config = super().default_config()
         config["jwt_config"] = {
             "enabled": True,
@@ -1435,7 +1424,7 @@ class JWTPubKeyTestCase(unittest.HomeserverTestCase):
         }
         return config
 
-    def jwt_encode(self, payload: Dict[str, Any], secret: str = jwt_privatekey) -> str:
+    def jwt_encode(self, payload: dict[str, Any], secret: str = jwt_privatekey) -> str:
         header = {"alg": "RS256"}
         if secret.startswith("-----BEGIN RSA PRIVATE KEY-----"):
             secret = JsonWebKey.import_key(secret, {"kty": "RSA"})
@@ -1630,7 +1619,7 @@ class UsernamePickerTestCase(HomeserverTestCase):
         )
         return hs
 
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         config = super().default_config()
         config["public_baseurl"] = PUBLIC_BASEURL
 
@@ -1649,7 +1638,7 @@ class UsernamePickerTestCase(HomeserverTestCase):
         config["sso"] = {"client_whitelist": ["https://x"]}
         return config
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         d = super().create_resource_dict()
         d.update(build_synapse_client_resource_tree(self.hs))
         return d
@@ -1660,7 +1649,7 @@ class UsernamePickerTestCase(HomeserverTestCase):
         displayname: str,
         email: str,
         picture: str,
-    ) -> Tuple[str, str]:
+    ) -> tuple[str, str]:
         # do the start of the login flow
         channel, _ = self.helper.auth_via_oidc(
             fake_oidc_server,
@@ -1681,7 +1670,7 @@ class UsernamePickerTestCase(HomeserverTestCase):
         self.assertEqual(picker_url, "/_synapse/client/pick_username/account_details")
 
         # ... with a username_mapping_session cookie
-        cookies: Dict[str, str] = {}
+        cookies: dict[str, str] = {}
         channel.extract_cookies(cookies)
         self.assertIn("username_mapping_session", cookies)
         session_id = cookies["username_mapping_session"]
@@ -1891,8 +1880,8 @@ class UsernamePickerTestCase(HomeserverTestCase):
 async def mock_get_file(
     url: str,
     output_stream: BinaryIO,
-    max_size: Optional[int] = None,
-    headers: Optional[RawHeaders] = None,
-    is_allowed_content_type: Optional[Callable[[str], bool]] = None,
-) -> Tuple[int, Dict[bytes, List[bytes]], str, int]:
+    max_size: int | None = None,
+    headers: RawHeaders | None = None,
+    is_allowed_content_type: Callable[[str], bool] | None = None,
+) -> tuple[int, dict[bytes, list[bytes]], str, int]:
     return 0, {b"Content-Type": [b"image/png"]}, "", 200
diff --git a/tests/rest/client/test_matrixrtc.py b/tests/rest/client/test_matrixrtc.py
new file mode 100644
index 0000000000..b5216c7adc
--- /dev/null
+++ b/tests/rest/client/test_matrixrtc.py
@@ -0,0 +1,105 @@
+#
+# This file is licensed under the Affero General Public License (AGPL) version 3.
+#
+# Copyright (C) 2025 New Vector, Ltd
+#
+# This program is free software: you can redistribute it and/or modify
+# it under the terms of the GNU Affero General Public License as
+# published by the Free Software Foundation, either version 3 of the
+# License, or (at your option) any later version.
+#
+# See the GNU Affero General Public License for more details:
+# <https://www.gnu.org/licenses/agpl-3.0.html>.
+#
+# [This file includes modifications made by New Vector Limited]
+#
+#
+
+"""Tests REST events for /rtc/endpoints path."""
+
+from twisted.internet.testing import MemoryReactor
+
+from synapse.rest import admin
+from synapse.rest.client import login, matrixrtc, register, room
+from synapse.server import HomeServer
+from synapse.util.clock import Clock
+
+from tests.unittest import HomeserverTestCase, override_config
+
+PATH_PREFIX = "/_matrix/client/unstable/org.matrix.msc4143"
+RTC_ENDPOINT = {"type": "focusA", "required_field": "theField"}
+LIVEKIT_ENDPOINT = {
+    "type": "livekit",
+    "livekit_service_url": "https://livekit.example.com",
+}
+
+
+class MatrixRtcTestCase(HomeserverTestCase):
+    """Tests /rtc/transports Client-Server REST API."""
+
+    servlets = [
+        admin.register_servlets,
+        room.register_servlets,
+        login.register_servlets,
+        register.register_servlets,
+        matrixrtc.register_servlets,
+    ]
+
+    def prepare(
+        self, reactor: MemoryReactor, clock: Clock, homeserver: HomeServer
+    ) -> None:
+        self.register_user("alice", "password")
+        self._alice_tok = self.login("alice", "password")
+
+    def test_matrixrtc_endpoint_not_enabled(self) -> None:
+        channel = self.make_request(
+            "GET", f"{PATH_PREFIX}/rtc/transports", access_token=self._alice_tok
+        )
+        self.assertEqual(404, channel.code, channel.json_body)
+        self.assertEqual(
+            "M_UNRECOGNIZED", channel.json_body["errcode"], channel.json_body
+        )
+
+    @override_config({"experimental_features": {"msc4143_enabled": True}})
+    def test_matrixrtc_endpoint_requires_authentication(self) -> None:
+        channel = self.make_request("GET", f"{PATH_PREFIX}/rtc/transports")
+        self.assertEqual(401, channel.code, channel.json_body)
+
+    @override_config(
+        {
+            "experimental_features": {"msc4143_enabled": True},
+            "matrix_rtc": {"transports": [RTC_ENDPOINT]},
+        }
+    )
+    def test_matrixrtc_endpoint_contains_expected_transport(self) -> None:
+        channel = self.make_request(
+            "GET", f"{PATH_PREFIX}/rtc/transports", access_token=self._alice_tok
+        )
+        self.assertEqual(200, channel.code, channel.json_body)
+        self.assert_dict({"rtc_transports": [RTC_ENDPOINT]}, channel.json_body)
+
+    @override_config(
+        {
+            "experimental_features": {"msc4143_enabled": True},
+            "matrix_rtc": {"transports": []},
+        }
+    )
+    def test_matrixrtc_endpoint_no_transports_configured(self) -> None:
+        channel = self.make_request(
+            "GET", f"{PATH_PREFIX}/rtc/transports", access_token=self._alice_tok
+        )
+        self.assertEqual(200, channel.code, channel.json_body)
+        self.assert_dict({}, channel.json_body)
+
+    @override_config(
+        {
+            "experimental_features": {"msc4143_enabled": True},
+            "matrix_rtc": {"transports": [LIVEKIT_ENDPOINT]},
+        }
+    )
+    def test_matrixrtc_endpoint_livekit_transport(self) -> None:
+        channel = self.make_request(
+            "GET", f"{PATH_PREFIX}/rtc/transports", access_token=self._alice_tok
+        )
+        self.assertEqual(200, channel.code, channel.json_body)
+        self.assert_dict({"rtc_transports": [LIVEKIT_ENDPOINT]}, channel.json_body)
diff --git a/tests/rest/client/test_media.py b/tests/rest/client/test_media.py
index 91bf94b672..33172f930e 100644
--- a/tests/rest/client/test_media.py
+++ b/tests/rest/client/test_media.py
@@ -24,7 +24,7 @@ import json
 import os
 import re
 import shutil
-from typing import Any, BinaryIO, ClassVar, Dict, List, Optional, Sequence, Tuple, Type
+from typing import Any, BinaryIO, ClassVar, Sequence
 from unittest.mock import MagicMock, Mock, patch
 from urllib import parse
 from urllib.parse import quote, urlencode
@@ -265,7 +265,7 @@ class URLPreviewTests(unittest.HomeserverTestCase):
         assert self.media_repo.url_previewer is not None
         self.url_previewer = self.media_repo.url_previewer
 
-        self.lookups: Dict[str, Any] = {}
+        self.lookups: dict[str, Any] = {}
 
         class Resolver:
             def resolveHostName(
@@ -273,7 +273,7 @@ class URLPreviewTests(unittest.HomeserverTestCase):
                 resolutionReceiver: IResolutionReceiver,
                 hostName: str,
                 portNumber: int = 0,
-                addressTypes: Optional[Sequence[Type[IAddress]]] = None,
+                addressTypes: Sequence[type[IAddress]] | None = None,
                 transportSemantics: str = "TCP",
             ) -> IResolutionReceiver:
                 resolution = HostResolution(hostName)
@@ -1357,7 +1357,7 @@ class URLPreviewTests(unittest.HomeserverTestCase):
         self.assertEqual(body["og:title"], "Test")
         self.assertNotIn("og:image", body)
 
-    def _download_image(self) -> Tuple[str, str]:
+    def _download_image(self) -> tuple[str, str]:
         """Downloads an image into the URL cache.
         Returns:
             A (host, media_id) tuple representing the MXC URI of the image.
@@ -1661,7 +1661,7 @@ class MediaConfigModuleCallbackTestCase(unittest.HomeserverTestCase):
     async def get_media_config_for_user(
         self,
         user_id: str,
-    ) -> Optional[JsonDict]:
+    ) -> JsonDict | None:
         # We echo back the user_id and set a custom upload size.
         return {"m.upload.size": 1024, "user_id": user_id}
 
@@ -1994,12 +1994,12 @@ class DownloadAndThumbnailTestCase(unittest.HomeserverTestCase):
     ]
 
     def make_homeserver(self, reactor: MemoryReactor, clock: Clock) -> HomeServer:
-        self.fetches: List[
-            Tuple[
+        self.fetches: list[
+            tuple[
                 "Deferred[Any]",
                 str,
                 str,
-                Optional[QueryParams],
+                QueryParams | None,
             ]
         ] = []
 
@@ -2010,16 +2010,16 @@ class DownloadAndThumbnailTestCase(unittest.HomeserverTestCase):
             download_ratelimiter: Ratelimiter,
             ip_address: Any,
             max_size: int,
-            args: Optional[QueryParams] = None,
+            args: QueryParams | None = None,
             retry_on_dns_fail: bool = True,
             ignore_backoff: bool = False,
             follow_redirects: bool = False,
-        ) -> "Deferred[Tuple[int, Dict[bytes, List[bytes]], bytes]]":
+        ) -> "Deferred[tuple[int, dict[bytes, list[bytes]], bytes]]":
             """A mock for MatrixFederationHttpClient.federation_get_file."""
 
             def write_to(
-                r: Tuple[bytes, Tuple[int, Dict[bytes, List[bytes]], bytes]],
-            ) -> Tuple[int, Dict[bytes, List[bytes]], bytes]:
+                r: tuple[bytes, tuple[int, dict[bytes, list[bytes]], bytes]],
+            ) -> tuple[int, dict[bytes, list[bytes]], bytes]:
                 data, response = r
                 output_stream.write(data)
                 return response
@@ -2029,7 +2029,7 @@ class DownloadAndThumbnailTestCase(unittest.HomeserverTestCase):
                 output_stream.write(f.value.response)
                 return f
 
-            d: Deferred[Tuple[bytes, Tuple[int, Dict[bytes, List[bytes]], bytes]]] = (
+            d: Deferred[tuple[bytes, tuple[int, dict[bytes, list[bytes]], bytes]]] = (
                 Deferred()
             )
             self.fetches.append((d, destination, path, args))
@@ -2044,16 +2044,16 @@ class DownloadAndThumbnailTestCase(unittest.HomeserverTestCase):
             download_ratelimiter: Ratelimiter,
             ip_address: Any,
             max_size: int,
-            args: Optional[QueryParams] = None,
+            args: QueryParams | None = None,
             retry_on_dns_fail: bool = True,
             ignore_backoff: bool = False,
             follow_redirects: bool = False,
-        ) -> "Deferred[Tuple[int, Dict[bytes, List[bytes]]]]":
+        ) -> "Deferred[tuple[int, dict[bytes, list[bytes]]]]":
             """A mock for MatrixFederationHttpClient.get_file."""
 
             def write_to(
-                r: Tuple[bytes, Tuple[int, Dict[bytes, List[bytes]]]],
-            ) -> Tuple[int, Dict[bytes, List[bytes]]]:
+                r: tuple[bytes, tuple[int, dict[bytes, list[bytes]]]],
+            ) -> tuple[int, dict[bytes, list[bytes]]]:
                 data, response = r
                 output_stream.write(data)
                 return response
@@ -2063,7 +2063,7 @@ class DownloadAndThumbnailTestCase(unittest.HomeserverTestCase):
                 output_stream.write(f.value.response)
                 return f
 
-            d: Deferred[Tuple[bytes, Tuple[int, Dict[bytes, List[bytes]]]]] = Deferred()
+            d: Deferred[tuple[bytes, tuple[int, dict[bytes, list[bytes]]]]] = Deferred()
             self.fetches.append((d, destination, path, args))
             # Note that this callback changes the value held by d.
             d_after_callback = d.addCallbacks(write_to, write_err)
@@ -2107,7 +2107,7 @@ class DownloadAndThumbnailTestCase(unittest.HomeserverTestCase):
         self.tok = self.login("user", "pass")
 
     def _req(
-        self, content_disposition: Optional[bytes], include_content_type: bool = True
+        self, content_disposition: bytes | None, include_content_type: bool = True
     ) -> FakeChannel:
         channel = self.make_request(
             "GET",
@@ -2418,7 +2418,7 @@ class DownloadAndThumbnailTestCase(unittest.HomeserverTestCase):
     def _test_thumbnail(
         self,
         method: str,
-        expected_body: Optional[bytes],
+        expected_body: bytes | None,
         expected_found: bool,
         unable_to_thumbnail: bool = False,
     ) -> None:
@@ -2538,7 +2538,7 @@ configs = [
 
 @parameterized_class(configs)
 class AuthenticatedMediaTestCase(unittest.HomeserverTestCase):
-    extra_config: Dict[str, Any]
+    extra_config: dict[str, Any]
     servlets = [
         media.register_servlets,
         login.register_servlets,
@@ -2576,7 +2576,7 @@ class AuthenticatedMediaTestCase(unittest.HomeserverTestCase):
         self.user = self.register_user("user", "pass")
         self.tok = self.login("user", "pass")
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         resources = super().create_resource_dict()
         resources["/_matrix/media"] = self.hs.get_media_repository_resource()
         return resources
@@ -2895,7 +2895,7 @@ class MediaUploadLimits(unittest.HomeserverTestCase):
         self.user = self.register_user("user", "pass")
         self.tok = self.login("user", "pass")
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         resources = super().create_resource_dict()
         resources["/_matrix/media"] = self.hs.get_media_repository_resource()
         return resources
@@ -3012,7 +3012,7 @@ class MediaUploadLimitsModuleOverrides(unittest.HomeserverTestCase):
     async def _get_media_upload_limits_for_user(
         self,
         user_id: str,
-    ) -> Optional[List[MediaUploadLimit]]:
+    ) -> list[MediaUploadLimit] | None:
         # user1 has custom limits
         if user_id == self.user1:
             # n.b. we return these in increasing duration order and Synapse will need to sort them correctly
@@ -3037,7 +3037,7 @@ class MediaUploadLimitsModuleOverrides(unittest.HomeserverTestCase):
         sent_bytes: int,
         attempted_bytes: int,
     ) -> None:
-        self.last_media_upload_limit_exceeded: Optional[dict[str, object]] = {
+        self.last_media_upload_limit_exceeded: dict[str, object] | None = {
             "user_id": user_id,
             "limit": limit,
             "sent_bytes": sent_bytes,
@@ -3060,7 +3060,7 @@ class MediaUploadLimitsModuleOverrides(unittest.HomeserverTestCase):
             on_media_upload_limit_exceeded=self._on_media_upload_limit_exceeded,
         )
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         resources = super().create_resource_dict()
         resources["/_matrix/media"] = self.hs.get_media_repository_resource()
         return resources
diff --git a/tests/rest/client/test_models.py b/tests/rest/client/test_models.py
index 75479e6235..f297856830 100644
--- a/tests/rest/client/test_models.py
+++ b/tests/rest/client/test_models.py
@@ -21,7 +21,8 @@
 import unittest as stdlib_unittest
 from typing import Literal
 
-from synapse._pydantic_compat import BaseModel, ValidationError
+from pydantic import BaseModel, ValidationError
+
 from synapse.types.rest.client import EmailRequestTokenBody
 
 
@@ -35,16 +36,16 @@ class ThreepidMediumEnumTestCase(stdlib_unittest.TestCase):
         This is arguably more of a test of a class that inherits from str and Enum
         simultaneously.
         """
-        model = self.Model.parse_obj({"medium": "email"})
+        model = self.Model.model_validate({"medium": "email"})
         self.assertEqual(model.medium, "email")
 
     def test_rejects_invalid_medium_value(self) -> None:
         with self.assertRaises(ValidationError):
-            self.Model.parse_obj({"medium": "interpretive_dance"})
+            self.Model.model_validate({"medium": "interpretive_dance"})
 
     def test_rejects_invalid_medium_type(self) -> None:
         with self.assertRaises(ValidationError):
-            self.Model.parse_obj({"medium": 123})
+            self.Model.model_validate({"medium": 123})
 
 
 class EmailRequestTokenBodyTestCase(stdlib_unittest.TestCase):
@@ -56,14 +57,14 @@ class EmailRequestTokenBodyTestCase(stdlib_unittest.TestCase):
 
     def test_token_required_if_id_server_provided(self) -> None:
         with self.assertRaises(ValidationError):
-            EmailRequestTokenBody.parse_obj(
+            EmailRequestTokenBody.model_validate(
                 {
                     **self.base_request,
                     "id_server": "identity.wonderland.com",
                 }
             )
         with self.assertRaises(ValidationError):
-            EmailRequestTokenBody.parse_obj(
+            EmailRequestTokenBody.model_validate(
                 {
                     **self.base_request,
                     "id_server": "identity.wonderland.com",
@@ -73,7 +74,7 @@ class EmailRequestTokenBodyTestCase(stdlib_unittest.TestCase):
 
     def test_token_typechecked_when_id_server_provided(self) -> None:
         with self.assertRaises(ValidationError):
-            EmailRequestTokenBody.parse_obj(
+            EmailRequestTokenBody.model_validate(
                 {
                     **self.base_request,
                     "id_server": "identity.wonderland.com",
diff --git a/tests/rest/client/test_notifications.py b/tests/rest/client/test_notifications.py
index e00152389b..17f8da3e8b 100644
--- a/tests/rest/client/test_notifications.py
+++ b/tests/rest/client/test_notifications.py
@@ -18,7 +18,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import List, Optional, Tuple
 from unittest.mock import AsyncMock, Mock
 
 from twisted.internet.testing import MemoryReactor
@@ -155,8 +154,8 @@ class HTTPPusherTests(HomeserverTestCase):
         self.assertEqual(notification_event_ids, sent_event_ids[2:])
 
     def _request_notifications(
-        self, from_token: Optional[str], limit: int, expected_count: int
-    ) -> Tuple[List[str], str]:
+        self, from_token: str | None, limit: int, expected_count: int
+    ) -> tuple[list[str], str]:
         """
         Make a request to /notifications to get the latest events to be notified about.
 
diff --git a/tests/rest/client/test_profile.py b/tests/rest/client/test_profile.py
index 18b3d3a089..023a376ed1 100644
--- a/tests/rest/client/test_profile.py
+++ b/tests/rest/client/test_profile.py
@@ -24,7 +24,7 @@
 import logging
 import urllib.parse
 from http import HTTPStatus
-from typing import Any, Dict, Optional
+from typing import Any
 
 from canonicaljson import encode_canonical_json
 
@@ -177,7 +177,7 @@ class ProfileTestCase(unittest.HomeserverTestCase):
         )
         self.assertEqual(channel.code, 400, channel.result)
 
-    def _get_displayname(self, name: Optional[str] = None) -> Optional[str]:
+    def _get_displayname(self, name: str | None = None) -> str | None:
         channel = self.make_request(
             "GET", "/profile/%s/displayname" % (name or self.owner,)
         )
@@ -187,7 +187,7 @@ class ProfileTestCase(unittest.HomeserverTestCase):
         # https://github.com/matrix-org/synapse/issues/13137.
         return channel.json_body.get("displayname")
 
-    def _get_avatar_url(self, name: Optional[str] = None) -> Optional[str]:
+    def _get_avatar_url(self, name: str | None = None) -> str | None:
         channel = self.make_request(
             "GET", "/profile/%s/avatar_url" % (name or self.owner,)
         )
@@ -778,7 +778,7 @@ class ProfileTestCase(unittest.HomeserverTestCase):
         self.assertEqual(channel.code, 403, channel.result)
         self.assertEqual(channel.json_body["errcode"], Codes.FORBIDDEN)
 
-    def _setup_local_files(self, names_and_props: Dict[str, Dict[str, Any]]) -> None:
+    def _setup_local_files(self, names_and_props: dict[str, dict[str, Any]]) -> None:
         """Stores metadata about files in the database.
 
         Args:
@@ -846,7 +846,7 @@ class ProfilesRestrictedTestCase(unittest.HomeserverTestCase):
         self.try_fetch_profile(200, self.requester_tok)
 
     def try_fetch_profile(
-        self, expected_code: int, access_token: Optional[str] = None
+        self, expected_code: int, access_token: str | None = None
     ) -> None:
         self.request_profile(expected_code, access_token=access_token)
 
@@ -862,7 +862,7 @@ class ProfilesRestrictedTestCase(unittest.HomeserverTestCase):
         self,
         expected_code: int,
         url_suffix: str = "",
-        access_token: Optional[str] = None,
+        access_token: str | None = None,
     ) -> None:
         channel = self.make_request(
             "GET", self.profile_url + url_suffix, access_token=access_token
diff --git a/tests/rest/client/test_receipts.py b/tests/rest/client/test_receipts.py
index 0c1b631b8e..3a6a869c54 100644
--- a/tests/rest/client/test_receipts.py
+++ b/tests/rest/client/test_receipts.py
@@ -19,7 +19,6 @@
 #
 #
 from http import HTTPStatus
-from typing import Optional
 
 from twisted.internet.testing import MemoryReactor
 
@@ -259,7 +258,7 @@ class ReceiptsTestCase(unittest.HomeserverTestCase):
         self.assertEqual(channel.code, HTTPStatus.BAD_REQUEST)
         self.assertEqual(channel.json_body["errcode"], "M_NOT_JSON", channel.json_body)
 
-    def _get_read_receipt(self) -> Optional[JsonDict]:
+    def _get_read_receipt(self) -> JsonDict | None:
         """Syncs and returns the read receipt."""
 
         # Checks if event is a read receipt
diff --git a/tests/rest/client/test_redactions.py b/tests/rest/client/test_redactions.py
index e3ca108d03..997ca5f9ca 100644
--- a/tests/rest/client/test_redactions.py
+++ b/tests/rest/client/test_redactions.py
@@ -18,7 +18,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import List, Optional
 
 from parameterized import parameterized
 
@@ -85,8 +84,8 @@ class RedactionsTestCase(HomeserverTestCase):
         room_id: str,
         event_id: str,
         expect_code: int = 200,
-        with_relations: Optional[List[str]] = None,
-        content: Optional[JsonDict] = None,
+        with_relations: list[str] | None = None,
+        content: JsonDict | None = None,
     ) -> JsonDict:
         """Helper function to send a redaction event.
 
@@ -104,7 +103,7 @@ class RedactionsTestCase(HomeserverTestCase):
         self.assertEqual(channel.code, expect_code)
         return channel.json_body
 
-    def _sync_room_timeline(self, access_token: str, room_id: str) -> List[JsonDict]:
+    def _sync_room_timeline(self, access_token: str, room_id: str) -> list[JsonDict]:
         channel = self.make_request("GET", "sync", access_token=access_token)
         self.assertEqual(channel.code, 200)
         room_sync = channel.json_body["rooms"]["join"][room_id]
diff --git a/tests/rest/client/test_register.py b/tests/rest/client/test_register.py
index c7c81aa81c..2c0396a3de 100644
--- a/tests/rest/client/test_register.py
+++ b/tests/rest/client/test_register.py
@@ -22,7 +22,7 @@
 import datetime
 import importlib.resources as importlib_resources
 import os
-from typing import Any, Dict, List, Tuple
+from typing import Any
 from unittest.mock import AsyncMock
 
 from twisted.internet.testing import MemoryReactor
@@ -54,7 +54,7 @@ class RegisterRestServletTestCase(unittest.HomeserverTestCase):
     ]
     url = b"/_matrix/client/r0/register"
 
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         config = super().default_config()
         config["allow_guest_access"] = True
         return config
@@ -1032,7 +1032,7 @@ class AccountValidityRenewalByEmailTestCase(unittest.HomeserverTestCase):
         async def sendmail(*args: Any, **kwargs: Any) -> None:
             self.email_attempts.append((args, kwargs))
 
-        self.email_attempts: List[Tuple[Any, Any]] = []
+        self.email_attempts: list[tuple[Any, Any]] = []
         self.hs.get_send_email_handler()._sendmail = sendmail
 
         self.store = self.hs.get_datastores().main
@@ -1146,7 +1146,7 @@ class AccountValidityRenewalByEmailTestCase(unittest.HomeserverTestCase):
 
         self.assertEqual(len(self.email_attempts), 0)
 
-    def create_user(self) -> Tuple[str, str]:
+    def create_user(self) -> tuple[str, str]:
         user_id = self.register_user("kermit", "monkey")
         tok = self.login("kermit", "monkey")
         # We need to manually add an email address otherwise the handler will do
@@ -1250,7 +1250,7 @@ class RegistrationTokenValidityRestServletTestCase(unittest.HomeserverTestCase):
     servlets = [register.register_servlets]
     url = "/_matrix/client/v1/register/m.login.registration_token/validity"
 
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         config = super().default_config()
         config["registration_requires_token"] = True
         return config
diff --git a/tests/rest/client/test_relations.py b/tests/rest/client/test_relations.py
index 21fb86367a..2d8ba77a77 100644
--- a/tests/rest/client/test_relations.py
+++ b/tests/rest/client/test_relations.py
@@ -20,7 +20,7 @@
 #
 
 import urllib.parse
-from typing import Any, Callable, Dict, List, Optional, Tuple
+from typing import Any, Callable
 from unittest.mock import AsyncMock, patch
 
 from twisted.internet.testing import MemoryReactor
@@ -48,7 +48,7 @@ class BaseRelationsTestCase(unittest.HomeserverTestCase):
     ]
     hijack_auth = False
 
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         # We need to enable msc1849 support for aggregations
         config = super().default_config()
 
@@ -69,7 +69,7 @@ class BaseRelationsTestCase(unittest.HomeserverTestCase):
         res = self.helper.send(self.room, body="Hi!", tok=self.user_token)
         self.parent_id = res["event_id"]
 
-    def _create_user(self, localpart: str) -> Tuple[str, str]:
+    def _create_user(self, localpart: str) -> tuple[str, str]:
         user_id = self.register_user(localpart, "abc123")
         access_token = self.login(localpart, "abc123")
 
@@ -79,10 +79,10 @@ class BaseRelationsTestCase(unittest.HomeserverTestCase):
         self,
         relation_type: str,
         event_type: str,
-        key: Optional[str] = None,
-        content: Optional[dict] = None,
-        access_token: Optional[str] = None,
-        parent_id: Optional[str] = None,
+        key: str | None = None,
+        content: dict | None = None,
+        access_token: str | None = None,
+        parent_id: str | None = None,
         expected_response_code: int = 200,
     ) -> FakeChannel:
         """Helper function to send a relation pointing at `self.parent_id`
@@ -123,7 +123,7 @@ class BaseRelationsTestCase(unittest.HomeserverTestCase):
         self.assertEqual(expected_response_code, channel.code, channel.json_body)
         return channel
 
-    def _get_related_events(self) -> List[str]:
+    def _get_related_events(self) -> list[str]:
         """
         Requests /relations on the parent ID and returns a list of event IDs.
         """
@@ -149,7 +149,7 @@ class BaseRelationsTestCase(unittest.HomeserverTestCase):
         self.assertEqual(200, channel.code, channel.json_body)
         return channel.json_body["unsigned"].get("m.relations", {})
 
-    def _find_event_in_chunk(self, events: List[JsonDict]) -> JsonDict:
+    def _find_event_in_chunk(self, events: list[JsonDict]) -> JsonDict:
         """
         Find the parent event in a chunk of events and assert that it has the proper bundled aggregations.
         """
@@ -845,8 +845,8 @@ class RelationPaginationTestCase(BaseRelationsTestCase):
             )
             expected_event_ids.append(channel.json_body["event_id"])
 
-        prev_token: Optional[str] = ""
-        found_event_ids: List[str] = []
+        prev_token: str | None = ""
+        found_event_ids: list[str] = []
         for _ in range(20):
             from_token = ""
             if prev_token:
@@ -1085,7 +1085,7 @@ class BundledAggregationsTestCase(BaseRelationsTestCase):
         relation_type: str,
         assertion_callable: Callable[[JsonDict], None],
         expected_db_txn_for_event: int,
-        access_token: Optional[str] = None,
+        access_token: str | None = None,
     ) -> None:
         """
         Makes requests to various endpoints which should include bundled aggregations
@@ -1484,9 +1484,9 @@ class RelationIgnoredUserTestCase(BaseRelationsTestCase):
     def _test_ignored_user(
         self,
         relation_type: str,
-        allowed_event_ids: List[str],
-        ignored_event_ids: List[str],
-    ) -> Tuple[JsonDict, JsonDict]:
+        allowed_event_ids: list[str],
+        ignored_event_ids: list[str],
+    ) -> tuple[JsonDict, JsonDict]:
         """
         Fetch the relations and ensure they're all there, then ignore user2, and
         repeat.
@@ -1600,7 +1600,7 @@ class RelationRedactionTestCase(BaseRelationsTestCase):
         )
         self.assertEqual(200, channel.code, channel.json_body)
 
-    def _get_threads(self) -> List[Tuple[str, str]]:
+    def _get_threads(self) -> list[tuple[str, str]]:
         """Request the threads in the room and returns a list of thread ID and latest event ID."""
         # Request the threads in the room.
         channel = self.make_request(
@@ -1793,7 +1793,7 @@ class RelationRedactionTestCase(BaseRelationsTestCase):
 
 
 class ThreadsTestCase(BaseRelationsTestCase):
-    def _get_threads(self, body: JsonDict) -> List[Tuple[str, str]]:
+    def _get_threads(self, body: JsonDict) -> list[tuple[str, str]]:
         return [
             (
                 ev["event_id"],
diff --git a/tests/rest/client/test_rendezvous.py b/tests/rest/client/test_rendezvous.py
index 160f852705..dc4f833fa2 100644
--- a/tests/rest/client/test_rendezvous.py
+++ b/tests/rest/client/test_rendezvous.py
@@ -19,7 +19,6 @@
 #
 #
 
-from typing import Dict
 from urllib.parse import urlparse
 
 from twisted.internet.testing import MemoryReactor
@@ -46,7 +45,7 @@ class RendezvousServletTestCase(unittest.HomeserverTestCase):
         self.hs = self.setup_test_homeserver()
         return self.hs
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         return {
             **super().create_resource_dict(),
             "/_synapse/client/rendezvous": MSC4108RendezvousSessionResource(self.hs),
diff --git a/tests/rest/client/test_reporting.py b/tests/rest/client/test_reporting.py
index 0fd02f65a6..96697b96d5 100644
--- a/tests/rest/client/test_reporting.py
+++ b/tests/rest/client/test_reporting.py
@@ -18,7 +18,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Optional
 
 from twisted.internet.testing import MemoryReactor
 
@@ -311,7 +310,7 @@ class ReportUserTestCase(unittest.HomeserverTestCase):
         self.assertEqual(len(rows), 0)
 
     def _assert_status(
-        self, response_status: int, data: JsonDict, user_id: Optional[str] = None
+        self, response_status: int, data: JsonDict, user_id: str | None = None
     ) -> None:
         if user_id is None:
             user_id = self.target_user_id
diff --git a/tests/rest/client/test_retention.py b/tests/rest/client/test_retention.py
index 7a816a66e0..758d62e63b 100644
--- a/tests/rest/client/test_retention.py
+++ b/tests/rest/client/test_retention.py
@@ -17,7 +17,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Any, Dict
+from typing import Any
 from unittest.mock import Mock
 
 from twisted.internet.testing import MemoryReactor
@@ -265,7 +265,7 @@ class RetentionNoDefaultPolicyTestCase(unittest.HomeserverTestCase):
         room.register_servlets,
     ]
 
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         config = super().default_config()
 
         retention_config = {
diff --git a/tests/rest/client/test_rooms.py b/tests/rest/client/test_rooms.py
index feae5f77cd..68e09afc54 100644
--- a/tests/rest/client/test_rooms.py
+++ b/tests/rest/client/test_rooms.py
@@ -25,7 +25,7 @@
 
 import json
 from http import HTTPStatus
-from typing import Any, Dict, Iterable, List, Literal, Optional, Tuple, Union
+from typing import Any, Iterable, Literal
 from unittest.mock import AsyncMock, Mock, call, patch
 from urllib import parse as urlparse
 
@@ -74,7 +74,7 @@ PATH_PREFIX = b"/_matrix/client/api/v1"
 
 
 class RoomBase(unittest.HomeserverTestCase):
-    rmcreator_id: Optional[str] = None
+    rmcreator_id: str | None = None
 
     servlets = [room.register_servlets, room.register_deprecated_servlets]
 
@@ -959,7 +959,7 @@ class RoomsCreateTestCase(RoomBase):
         """Tests that the user_may_join_room spam checker callback is correctly bypassed
         when creating a new room.
 
-        In this test, we use the more recent API in which callbacks return a `Union[Codes, Literal["NOT_SPAM"]]`.
+        In this test, we use the more recent API in which callbacks return a `Codes | Literal["NOT_SPAM"]`.
         """
 
         async def user_may_join_room_codes(
@@ -989,7 +989,7 @@ class RoomsCreateTestCase(RoomBase):
             mxid: str,
             room_id: str,
             is_invite: bool,
-        ) -> Tuple[Codes, dict]:
+        ) -> tuple[Codes, dict]:
             return Codes.INCOMPATIBLE_ROOM_VERSION, {}
 
         join_mock.side_effect = user_may_join_room_tuple
@@ -1002,7 +1002,7 @@ class RoomsCreateTestCase(RoomBase):
         self.assertEqual(channel.code, HTTPStatus.OK, channel.json_body)
         self.assertEqual(join_mock.call_count, 0)
 
-    def _create_basic_room(self) -> Tuple[int, object]:
+    def _create_basic_room(self) -> tuple[int, object]:
         """
         Tries to create a basic room and returns the response code.
         """
@@ -1351,7 +1351,7 @@ class RoomJoinTestCase(RoomBase):
         """
 
         # Register a dummy callback. Make it allow all room joins for now.
-        return_value: Union[Literal["NOT_SPAM"], Tuple[Codes, dict], Codes] = (
+        return_value: Literal["NOT_SPAM"] | tuple[Codes, dict] | Codes = (
             synapse.module_api.NOT_SPAM
         )
 
@@ -1359,7 +1359,7 @@ class RoomJoinTestCase(RoomBase):
             userid: str,
             room_id: str,
             is_invited: bool,
-        ) -> Union[Literal["NOT_SPAM"], Tuple[Codes, dict], Codes]:
+        ) -> Literal["NOT_SPAM"] | tuple[Codes, dict] | Codes:
             return return_value
 
         # `spec` argument is needed for this function mock to have `__qualname__`, which
@@ -1848,20 +1848,20 @@ class RoomMessagesTestCase(RoomBase):
     def test_spam_checker_check_event_for_spam(
         self,
         name: str,
-        value: Union[str, bool, Codes, Tuple[Codes, JsonDict]],
+        value: str | bool | Codes | tuple[Codes, JsonDict],
         expected_code: int,
         expected_fields: dict,
     ) -> None:
         class SpamCheck:
-            mock_return_value: Union[str, bool, Codes, Tuple[Codes, JsonDict], bool] = (
+            mock_return_value: str | bool | Codes | tuple[Codes, JsonDict] | bool = (
                 "NOT_SPAM"
             )
-            mock_content: Optional[JsonDict] = None
+            mock_content: JsonDict | None = None
 
             async def check_event_for_spam(
                 self,
                 event: synapse.events.EventBase,
-            ) -> Union[str, Codes, Tuple[Codes, JsonDict], bool]:
+            ) -> str | Codes | tuple[Codes, JsonDict] | bool:
                 self.mock_content = event.content
                 return self.mock_return_value
 
@@ -1915,7 +1915,7 @@ class RoomPowerLevelOverridesTestCase(RoomBase):
         self.admin_user_id = self.register_user("admin", "pass")
         self.admin_access_token = self.login("admin", "pass")
 
-    def power_levels(self, room_id: str) -> Dict[str, Any]:
+    def power_levels(self, room_id: str) -> dict[str, Any]:
         return self.helper.get_state(
             room_id, "m.room.power_levels", self.admin_access_token
         )
@@ -2076,7 +2076,7 @@ class RoomPowerLevelOverridesInPracticeTestCase(RoomBase):
         # Given the server has config allowing normal users to post my event type
         # And I am a normal member of a room
         # But the room was created with special permissions
-        extra_content: Dict[str, Any] = {
+        extra_content: dict[str, Any] = {
             "power_level_content_override": {"events": {}},
         }
         room_id = self.helper.create_room_as(
@@ -2707,9 +2707,9 @@ class PublicRoomsRoomTypeFilterTestCase(unittest.HomeserverTestCase):
 
     def make_public_rooms_request(
         self,
-        room_types: Optional[List[Union[str, None]]],
-        instance_id: Optional[str] = None,
-    ) -> Tuple[List[Dict[str, Any]], int]:
+        room_types: list[str | None] | None,
+        instance_id: str | None = None,
+    ) -> tuple[list[dict[str, Any]], int]:
         body: JsonDict = {"filter": {PublicRoomsFilterFields.ROOM_TYPES: room_types}}
         if instance_id:
             body["third_party_instance_id"] = "test|test"
@@ -3470,7 +3470,7 @@ class LabelsTestCase(unittest.HomeserverTestCase):
 
 
 class RelationsTestCase(PaginationTestCase):
-    def _filter_messages(self, filter: JsonDict) -> List[str]:
+    def _filter_messages(self, filter: JsonDict) -> list[str]:
         """Make a request to /messages with a filter, returns the chunk of events."""
         from_token = self.get_success(
             self.from_token.to_string(self.hs.get_datastores().main)
@@ -3968,7 +3968,7 @@ class ThreepidInviteTestCase(unittest.HomeserverTestCase):
         """
         Test allowing/blocking threepid invites with a spam-check module.
 
-        In this test, we use the more recent API in which callbacks return a `Union[Codes, Literal["NOT_SPAM"]]`.
+        In this test, we use the more recent API in which callbacks return a `Codes | Literal["NOT_SPAM"]`.
         """
         # Mock a few functions to prevent the test from failing due to failing to talk to
         # a remote IS. We keep the mock for make_and_store_3pid_invite around so we
@@ -4529,10 +4529,10 @@ class MSC4293RedactOnBanKickTestCase(unittest.FederatingHomeserverTestCase):
 
     def _check_redactions(
         self,
-        original_events: List[EventBase],
-        pulled_events: List[JsonDict],
+        original_events: list[EventBase],
+        pulled_events: list[JsonDict],
         expect_redaction: bool,
-        reason: Optional[str] = None,
+        reason: str | None = None,
     ) -> None:
         """
         Checks a set of original events against a second set of the same events, pulled
diff --git a/tests/rest/client/test_sync.py b/tests/rest/client/test_sync.py
index e949bb69e6..fcbf3fd53c 100644
--- a/tests/rest/client/test_sync.py
+++ b/tests/rest/client/test_sync.py
@@ -20,7 +20,6 @@
 #
 import json
 import logging
-from typing import List
 
 from parameterized import parameterized
 
@@ -131,7 +130,7 @@ class SyncFilterTestCase(unittest.HomeserverTestCase):
         self.assertEqual(len(events), 1, [event["content"] for event in events])
         self.assertEqual(events[0]["content"]["body"], "with wrong label", events[0])
 
-    def _test_sync_filter_labels(self, sync_filter: str) -> List[JsonDict]:
+    def _test_sync_filter_labels(self, sync_filter: str) -> list[JsonDict]:
         user_id = self.register_user("kermit", "test")
         tok = self.login("kermit", "test")
 
diff --git a/tests/rest/client/test_third_party_rules.py b/tests/rest/client/test_third_party_rules.py
index 4161faa11f..0d319dff7e 100644
--- a/tests/rest/client/test_third_party_rules.py
+++ b/tests/rest/client/test_third_party_rules.py
@@ -19,7 +19,7 @@
 #
 #
 import threading
-from typing import TYPE_CHECKING, Any, Dict, Optional, Tuple, Union
+from typing import TYPE_CHECKING, Any
 from unittest.mock import AsyncMock, Mock
 
 from twisted.internet.testing import MemoryReactor
@@ -48,7 +48,7 @@ thread_local = threading.local()
 
 
 class LegacyThirdPartyRulesTestModule:
-    def __init__(self, config: Dict, module_api: "ModuleApi") -> None:
+    def __init__(self, config: dict, module_api: "ModuleApi") -> None:
         # keep a record of the "current" rules module, so that the test can patch
         # it if desired.
         thread_local.rules_module = self
@@ -61,16 +61,16 @@ class LegacyThirdPartyRulesTestModule:
 
     async def check_event_allowed(
         self, event: EventBase, state: StateMap[EventBase]
-    ) -> Union[bool, dict]:
+    ) -> bool | dict:
         return True
 
     @staticmethod
-    def parse_config(config: Dict[str, Any]) -> Dict[str, Any]:
+    def parse_config(config: dict[str, Any]) -> dict[str, Any]:
         return config
 
 
 class LegacyDenyNewRooms(LegacyThirdPartyRulesTestModule):
-    def __init__(self, config: Dict, module_api: "ModuleApi") -> None:
+    def __init__(self, config: dict, module_api: "ModuleApi") -> None:
         super().__init__(config, module_api)
 
     async def on_create_room(
@@ -80,7 +80,7 @@ class LegacyDenyNewRooms(LegacyThirdPartyRulesTestModule):
 
 
 class LegacyChangeEvents(LegacyThirdPartyRulesTestModule):
-    def __init__(self, config: Dict, module_api: "ModuleApi") -> None:
+    def __init__(self, config: dict, module_api: "ModuleApi") -> None:
         super().__init__(config, module_api)
 
     async def check_event_allowed(
@@ -150,7 +150,7 @@ class ThirdPartyRulesTestCase(unittest.FederatingHomeserverTestCase):
         # types
         async def check(
             ev: EventBase, state: StateMap[EventBase]
-        ) -> Tuple[bool, Optional[JsonDict]]:
+        ) -> tuple[bool, JsonDict | None]:
             return ev.type != "foo.bar.forbidden", None
 
         callback = Mock(spec=[], side_effect=check)
@@ -195,7 +195,7 @@ class ThirdPartyRulesTestCase(unittest.FederatingHomeserverTestCase):
         """
 
         class NastyHackException(SynapseError):
-            def error_dict(self, config: Optional[HomeServerConfig]) -> JsonDict:
+            def error_dict(self, config: HomeServerConfig | None) -> JsonDict:
                 """
                 This overrides SynapseError's `error_dict` to nastily inject
                 JSON into the error response.
@@ -207,7 +207,7 @@ class ThirdPartyRulesTestCase(unittest.FederatingHomeserverTestCase):
         # add a callback that will raise our hacky exception
         async def check(
             ev: EventBase, state: StateMap[EventBase]
-        ) -> Tuple[bool, Optional[JsonDict]]:
+        ) -> tuple[bool, JsonDict | None]:
             raise NastyHackException(429, "message")
 
         self.hs.get_module_api_callbacks().third_party_event_rules._check_event_allowed_callbacks = [
@@ -235,7 +235,7 @@ class ThirdPartyRulesTestCase(unittest.FederatingHomeserverTestCase):
         # first patch the event checker so that it will try to modify the event
         async def check(
             ev: EventBase, state: StateMap[EventBase]
-        ) -> Tuple[bool, Optional[JsonDict]]:
+        ) -> tuple[bool, JsonDict | None]:
             ev.content = {"x": "y"}
             return True, None
 
@@ -260,7 +260,7 @@ class ThirdPartyRulesTestCase(unittest.FederatingHomeserverTestCase):
         # first patch the event checker so that it will modify the event
         async def check(
             ev: EventBase, state: StateMap[EventBase]
-        ) -> Tuple[bool, Optional[JsonDict]]:
+        ) -> tuple[bool, JsonDict | None]:
             d = ev.get_dict()
             d["content"] = {"x": "y"}
             return True, d
@@ -295,7 +295,7 @@ class ThirdPartyRulesTestCase(unittest.FederatingHomeserverTestCase):
         # first patch the event checker so that it will modify the event
         async def check(
             ev: EventBase, state: StateMap[EventBase]
-        ) -> Tuple[bool, Optional[JsonDict]]:
+        ) -> tuple[bool, JsonDict | None]:
             d = ev.get_dict()
             d["content"] = {
                 "msgtype": "m.text",
@@ -443,7 +443,7 @@ class ThirdPartyRulesTestCase(unittest.FederatingHomeserverTestCase):
         # Define a callback that sends a custom event on power levels update.
         async def test_fn(
             event: EventBase, state_events: StateMap[EventBase]
-        ) -> Tuple[bool, Optional[JsonDict]]:
+        ) -> tuple[bool, JsonDict | None]:
             if event.is_state() and event.type == EventTypes.PowerLevels:
                 await api.create_and_send_event_into_room(
                     {
diff --git a/tests/rest/client/test_thread_subscriptions.py b/tests/rest/client/test_thread_subscriptions.py
index 5aae07ef50..87c477cbb5 100644
--- a/tests/rest/client/test_thread_subscriptions.py
+++ b/tests/rest/client/test_thread_subscriptions.py
@@ -111,7 +111,7 @@ class ThreadSubscriptionsTestCase(unittest.HomeserverTestCase):
             {},
             access_token=self.token,
         )
-        self.assertEqual(channel.code, HTTPStatus.OK)
+        self.assertEqual(channel.code, HTTPStatus.OK, channel.json_body)
 
         # Assert the subscription was saved
         channel = self.make_request(
@@ -119,8 +119,8 @@ class ThreadSubscriptionsTestCase(unittest.HomeserverTestCase):
             f"{PREFIX}/{self.room_id}/thread/{self.root_event_id}/subscription",
             access_token=self.token,
         )
-        self.assertEqual(channel.code, HTTPStatus.OK)
-        self.assertEqual(channel.json_body, {"automatic": False})
+        self.assertEqual(channel.code, HTTPStatus.OK, channel.json_body)
+        self.assertEqual(channel.json_body, {"automatic": False}, channel.json_body)
 
         # Now also register an automatic subscription; it should not
         # override the manual subscription
@@ -130,7 +130,7 @@ class ThreadSubscriptionsTestCase(unittest.HomeserverTestCase):
             {"automatic": self.threaded_events[0]},
             access_token=self.token,
         )
-        self.assertEqual(channel.code, HTTPStatus.OK)
+        self.assertEqual(channel.code, HTTPStatus.OK, channel.json_body)
 
         # Assert the manual subscription was not overridden
         channel = self.make_request(
@@ -138,8 +138,8 @@ class ThreadSubscriptionsTestCase(unittest.HomeserverTestCase):
             f"{PREFIX}/{self.room_id}/thread/{self.root_event_id}/subscription",
             access_token=self.token,
         )
-        self.assertEqual(channel.code, HTTPStatus.OK)
-        self.assertEqual(channel.json_body, {"automatic": False})
+        self.assertEqual(channel.code, HTTPStatus.OK, channel.json_body)
+        self.assertEqual(channel.json_body, {"automatic": False}, channel.json_body)
 
     def test_subscribe_automatic_then_manual(self) -> None:
         """Test subscribing to a thread, first an automatic subscription then a manual subscription.
@@ -160,8 +160,8 @@ class ThreadSubscriptionsTestCase(unittest.HomeserverTestCase):
             f"{PREFIX}/{self.room_id}/thread/{self.root_event_id}/subscription",
             access_token=self.token,
         )
-        self.assertEqual(channel.code, HTTPStatus.OK)
-        self.assertEqual(channel.json_body, {"automatic": True})
+        self.assertEqual(channel.code, HTTPStatus.OK, channel.json_body)
+        self.assertEqual(channel.json_body, {"automatic": True}, channel.json_body)
 
         # Now also register a manual subscription
         channel = self.make_request(
@@ -170,7 +170,7 @@ class ThreadSubscriptionsTestCase(unittest.HomeserverTestCase):
             {},
             access_token=self.token,
         )
-        self.assertEqual(channel.code, HTTPStatus.OK)
+        self.assertEqual(channel.code, HTTPStatus.OK, channel.json_body)
 
         # Assert the manual subscription was not overridden
         channel = self.make_request(
@@ -178,8 +178,8 @@ class ThreadSubscriptionsTestCase(unittest.HomeserverTestCase):
             f"{PREFIX}/{self.room_id}/thread/{self.root_event_id}/subscription",
             access_token=self.token,
         )
-        self.assertEqual(channel.code, HTTPStatus.OK)
-        self.assertEqual(channel.json_body, {"automatic": False})
+        self.assertEqual(channel.code, HTTPStatus.OK, channel.json_body)
+        self.assertEqual(channel.json_body, {"automatic": False}, channel.json_body)
 
     def test_unsubscribe(self) -> None:
         """Test subscribing to a thread, then unsubscribing."""
@@ -191,7 +191,7 @@ class ThreadSubscriptionsTestCase(unittest.HomeserverTestCase):
             },
             access_token=self.token,
         )
-        self.assertEqual(channel.code, HTTPStatus.OK)
+        self.assertEqual(channel.code, HTTPStatus.OK, channel.json_body)
 
         # Assert the subscription was saved
         channel = self.make_request(
@@ -199,23 +199,23 @@ class ThreadSubscriptionsTestCase(unittest.HomeserverTestCase):
             f"{PREFIX}/{self.room_id}/thread/{self.root_event_id}/subscription",
             access_token=self.token,
         )
-        self.assertEqual(channel.code, HTTPStatus.OK)
-        self.assertEqual(channel.json_body, {"automatic": True})
+        self.assertEqual(channel.code, HTTPStatus.OK, channel.json_body)
+        self.assertEqual(channel.json_body, {"automatic": True}, channel.json_body)
 
         channel = self.make_request(
             "DELETE",
             f"{PREFIX}/{self.room_id}/thread/{self.root_event_id}/subscription",
             access_token=self.token,
         )
-        self.assertEqual(channel.code, HTTPStatus.OK)
+        self.assertEqual(channel.code, HTTPStatus.OK, channel.json_body)
 
         channel = self.make_request(
             "GET",
             f"{PREFIX}/{self.room_id}/thread/{self.root_event_id}/subscription",
             access_token=self.token,
         )
-        self.assertEqual(channel.code, HTTPStatus.NOT_FOUND)
-        self.assertEqual(channel.json_body["errcode"], "M_NOT_FOUND")
+        self.assertEqual(channel.code, HTTPStatus.NOT_FOUND, channel.json_body)
+        self.assertEqual(channel.json_body["errcode"], "M_NOT_FOUND", channel.json_body)
 
     def test_set_thread_subscription_nonexistent_thread(self) -> None:
         """Test setting subscription settings for a nonexistent thread."""
@@ -225,8 +225,8 @@ class ThreadSubscriptionsTestCase(unittest.HomeserverTestCase):
             {},
             access_token=self.token,
         )
-        self.assertEqual(channel.code, HTTPStatus.NOT_FOUND)
-        self.assertEqual(channel.json_body["errcode"], "M_NOT_FOUND")
+        self.assertEqual(channel.code, HTTPStatus.NOT_FOUND, channel.json_body)
+        self.assertEqual(channel.json_body["errcode"], "M_NOT_FOUND", channel.json_body)
 
     def test_set_thread_subscription_no_access(self) -> None:
         """Test that a user can't set thread subscription for a thread they can't access."""
@@ -239,8 +239,8 @@ class ThreadSubscriptionsTestCase(unittest.HomeserverTestCase):
             {},
             access_token=no_access_token,
         )
-        self.assertEqual(channel.code, HTTPStatus.NOT_FOUND)
-        self.assertEqual(channel.json_body["errcode"], "M_NOT_FOUND")
+        self.assertEqual(channel.code, HTTPStatus.NOT_FOUND, channel.json_body)
+        self.assertEqual(channel.json_body["errcode"], "M_NOT_FOUND", channel.json_body)
 
     def test_invalid_body(self) -> None:
         """Test that sending invalid subscription settings is rejected."""
@@ -251,7 +251,7 @@ class ThreadSubscriptionsTestCase(unittest.HomeserverTestCase):
             {"automatic": True},
             access_token=self.token,
         )
-        self.assertEqual(channel.code, HTTPStatus.BAD_REQUEST)
+        self.assertEqual(channel.code, HTTPStatus.BAD_REQUEST, channel.json_body)
 
         channel = self.make_request(
             "PUT",
@@ -260,7 +260,7 @@ class ThreadSubscriptionsTestCase(unittest.HomeserverTestCase):
             {"automatic": "$malformedEventId"},
             access_token=self.token,
         )
-        self.assertEqual(channel.code, HTTPStatus.BAD_REQUEST)
+        self.assertEqual(channel.code, HTTPStatus.BAD_REQUEST, channel.json_body)
 
     def test_auto_subscribe_cause_event_not_in_thread(self) -> None:
         """
diff --git a/tests/rest/client/test_thread_updates.py b/tests/rest/client/test_thread_updates.py
index 011f12d28e..fb62b877e7 100644
--- a/tests/rest/client/test_thread_updates.py
+++ b/tests/rest/client/test_thread_updates.py
@@ -56,8 +56,9 @@ class ThreadUpdatesTestCase(unittest.HomeserverTestCase):
 
         # Request thread updates
         channel = self.make_request(
-            "GET",
+            "POST",
             "/_matrix/client/unstable/io.element.msc4360/thread_updates?dir=b",
+            content={},
             access_token=user1_tok,
         )
         self.assertEqual(channel.code, 200, channel.json_body)
@@ -95,9 +96,10 @@ class ThreadUpdatesTestCase(unittest.HomeserverTestCase):
 
         # Request thread updates
         channel = self.make_request(
-            "GET",
+            "POST",
             "/_matrix/client/unstable/io.element.msc4360/thread_updates?dir=b",
             access_token=user1_tok,
+            content={},
         )
         self.assertEqual(channel.code, 200, channel.json_body)
 
@@ -160,9 +162,10 @@ class ThreadUpdatesTestCase(unittest.HomeserverTestCase):
 
         # Request thread updates
         channel = self.make_request(
-            "GET",
+            "POST",
             "/_matrix/client/unstable/io.element.msc4360/thread_updates?dir=b",
             access_token=user1_tok,
+            content={},
         )
         self.assertEqual(channel.code, 200, channel.json_body)
 
@@ -221,9 +224,10 @@ class ThreadUpdatesTestCase(unittest.HomeserverTestCase):
 
         # Request thread updates
         channel = self.make_request(
-            "GET",
+            "POST",
             "/_matrix/client/unstable/io.element.msc4360/thread_updates?dir=b",
             access_token=user1_tok,
+            content={},
         )
         self.assertEqual(channel.code, 200, channel.json_body)
 
@@ -270,9 +274,10 @@ class ThreadUpdatesTestCase(unittest.HomeserverTestCase):
 
         # Request first page with small limit
         channel = self.make_request(
-            "GET",
+            "POST",
             "/_matrix/client/unstable/io.element.msc4360/thread_updates?dir=b&limit=2",
             access_token=user1_tok,
+            content={},
         )
         self.assertEqual(channel.code, 200, channel.json_body)
 
@@ -285,9 +290,10 @@ class ThreadUpdatesTestCase(unittest.HomeserverTestCase):
 
         # Request second page
         channel = self.make_request(
-            "GET",
+            "POST",
             f"/_matrix/client/unstable/io.element.msc4360/thread_updates?dir=b&limit=2&from={next_batch}",
             access_token=user1_tok,
+            content={},
         )
         self.assertEqual(channel.code, 200, channel.json_body)
 
@@ -306,9 +312,10 @@ class ThreadUpdatesTestCase(unittest.HomeserverTestCase):
         next_batch_2 = channel.json_body["next_batch"]
 
         channel = self.make_request(
-            "GET",
+            "POST",
             f"/_matrix/client/unstable/io.element.msc4360/thread_updates?dir=b&limit=2&from={next_batch_2}",
             access_token=user1_tok,
+            content={},
         )
         self.assertEqual(channel.code, 200, channel.json_body)
 
@@ -337,9 +344,10 @@ class ThreadUpdatesTestCase(unittest.HomeserverTestCase):
 
         # Request with forward direction should fail
         channel = self.make_request(
-            "GET",
+            "POST",
             "/_matrix/client/unstable/io.element.msc4360/thread_updates?dir=f",
             access_token=user1_tok,
+            content={},
         )
         self.assertEqual(channel.code, 400)
 
@@ -352,17 +360,19 @@ class ThreadUpdatesTestCase(unittest.HomeserverTestCase):
 
         # Zero limit should fail
         channel = self.make_request(
-            "GET",
+            "POST",
             "/_matrix/client/unstable/io.element.msc4360/thread_updates?dir=b&limit=0",
             access_token=user1_tok,
+            content={},
         )
         self.assertEqual(channel.code, 400)
 
         # Negative limit should fail
         channel = self.make_request(
-            "GET",
+            "POST",
             "/_matrix/client/unstable/io.element.msc4360/thread_updates?dir=b&limit=-5",
             access_token=user1_tok,
+            content={},
         )
         self.assertEqual(channel.code, 400)
 
@@ -375,17 +385,19 @@ class ThreadUpdatesTestCase(unittest.HomeserverTestCase):
 
         # Invalid from token
         channel = self.make_request(
-            "GET",
+            "POST",
             "/_matrix/client/unstable/io.element.msc4360/thread_updates?dir=b&from=invalid_token",
             access_token=user1_tok,
+            content={},
         )
         self.assertEqual(channel.code, 400)
 
         # Invalid to token
         channel = self.make_request(
-            "GET",
+            "POST",
             "/_matrix/client/unstable/io.element.msc4360/thread_updates?dir=b&to=invalid_token",
             access_token=user1_tok,
+            content={},
         )
         self.assertEqual(channel.code, 400)
 
@@ -439,9 +451,10 @@ class ThreadUpdatesTestCase(unittest.HomeserverTestCase):
 
         # Request with limit=1 to get only the latest thread update
         channel = self.make_request(
-            "GET",
+            "POST",
             "/_matrix/client/unstable/io.element.msc4360/thread_updates?dir=b&limit=1",
             access_token=user1_tok,
+            content={},
         )
         self.assertEqual(channel.code, 200)
         self.assertIn("next_batch", channel.json_body)
@@ -455,9 +468,10 @@ class ThreadUpdatesTestCase(unittest.HomeserverTestCase):
         # This should get only the same thread updates as before, not the additional
         # update.
         channel = self.make_request(
-            "GET",
+            "POST",
             f"/_matrix/client/unstable/io.element.msc4360/thread_updates?dir=b&to={next_batch}",
             access_token=user1_tok,
+            content={},
         )
         self.assertEqual(channel.code, 200)
 
@@ -506,9 +520,10 @@ class ThreadUpdatesTestCase(unittest.HomeserverTestCase):
 
         # Request thread updates
         channel = self.make_request(
-            "GET",
+            "POST",
             "/_matrix/client/unstable/io.element.msc4360/thread_updates?dir=b",
             access_token=user1_tok,
+            content={},
         )
         self.assertEqual(channel.code, 200)
 
@@ -584,9 +599,10 @@ class ThreadUpdatesTestCase(unittest.HomeserverTestCase):
 
         # Request thread updates for user1 - should only get room1
         channel = self.make_request(
-            "GET",
+            "POST",
             "/_matrix/client/unstable/io.element.msc4360/thread_updates?dir=b",
             access_token=user1_tok,
+            content={},
         )
         self.assertEqual(channel.code, 200)
 
diff --git a/tests/rest/client/test_transactions.py b/tests/rest/client/test_transactions.py
index 9c9eca5415..64d22d485a 100644
--- a/tests/rest/client/test_transactions.py
+++ b/tests/rest/client/test_transactions.py
@@ -20,7 +20,7 @@
 #
 
 from http import HTTPStatus
-from typing import Any, Generator, Tuple, cast
+from typing import Any, Generator, cast
 from unittest.mock import AsyncMock, Mock, call
 
 from twisted.internet import defer, reactor as _reactor
@@ -29,16 +29,19 @@ from synapse.logging.context import SENTINEL_CONTEXT, LoggingContext, current_co
 from synapse.rest.client.transactions import CLEANUP_PERIOD_MS, HttpTransactionCache
 from synapse.types import ISynapseReactor, JsonDict
 from synapse.util.clock import Clock
+from synapse.util.constants import (
+    MILLISECONDS_PER_SECOND,
+)
 
 from tests import unittest
-from tests.utils import MockClock
+from tests.server import get_clock
 
 reactor = cast(ISynapseReactor, _reactor)
 
 
 class HttpTransactionCacheTestCase(unittest.TestCase):
     def setUp(self) -> None:
-        self.clock = MockClock()
+        self.reactor, self.clock = get_clock()
         self.hs = Mock()
         self.hs.get_clock = Mock(return_value=self.clock)
         self.hs.get_auth = Mock()
@@ -89,9 +92,11 @@ class HttpTransactionCacheTestCase(unittest.TestCase):
         self,
     ) -> Generator["defer.Deferred[Any]", object, None]:
         @defer.inlineCallbacks
-        def cb() -> Generator["defer.Deferred[object]", object, Tuple[int, JsonDict]]:
+        def cb() -> Generator["defer.Deferred[object]", object, tuple[int, JsonDict]]:
+            # Ignore `multiple-internal-clocks` linter error here since we are creating a `Clock`
+            # for testing purposes.
             yield defer.ensureDeferred(
-                Clock(reactor, server_name="test_server").sleep(0)
+                Clock(reactor, server_name="test_server").sleep(0)  # type: ignore[multiple-internal-clocks]
             )
             return 1, {}
 
@@ -119,7 +124,7 @@ class HttpTransactionCacheTestCase(unittest.TestCase):
         """
         called = [False]
 
-        def cb() -> "defer.Deferred[Tuple[int, JsonDict]]":
+        def cb() -> "defer.Deferred[tuple[int, JsonDict]]":
             if called[0]:
                 # return a valid result the second time
                 return defer.succeed(self.mock_http_response)
@@ -151,7 +156,7 @@ class HttpTransactionCacheTestCase(unittest.TestCase):
         """
         called = [False]
 
-        def cb() -> "defer.Deferred[Tuple[int, JsonDict]]":
+        def cb() -> "defer.Deferred[tuple[int, JsonDict]]":
             if called[0]:
                 # return a valid result the second time
                 return defer.succeed(self.mock_http_response)
@@ -180,8 +185,9 @@ class HttpTransactionCacheTestCase(unittest.TestCase):
         yield self.cache.fetch_or_execute_request(
             self.mock_request, self.mock_requester, cb, "an arg"
         )
-        # should NOT have cleaned up yet
-        self.clock.advance_time_msec(CLEANUP_PERIOD_MS / 2)
+        # Advance time just under the cleanup period.
+        # Should NOT have cleaned up yet
+        self.reactor.advance((CLEANUP_PERIOD_MS - 1) / MILLISECONDS_PER_SECOND)
 
         yield self.cache.fetch_or_execute_request(
             self.mock_request, self.mock_requester, cb, "an arg"
@@ -189,7 +195,8 @@ class HttpTransactionCacheTestCase(unittest.TestCase):
         # still using cache
         cb.assert_called_once_with("an arg")
 
-        self.clock.advance_time_msec(CLEANUP_PERIOD_MS)
+        # Advance time just after the cleanup period.
+        self.reactor.advance(2 / MILLISECONDS_PER_SECOND)
 
         yield self.cache.fetch_or_execute_request(
             self.mock_request, self.mock_requester, cb, "an arg"
diff --git a/tests/rest/client/test_upgrade_room.py b/tests/rest/client/test_upgrade_room.py
index da114e505d..ee26492909 100644
--- a/tests/rest/client/test_upgrade_room.py
+++ b/tests/rest/client/test_upgrade_room.py
@@ -18,7 +18,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Optional
 from unittest.mock import patch
 
 from twisted.internet.testing import MemoryReactor
@@ -56,8 +55,8 @@ class UpgradeRoomTest(unittest.HomeserverTestCase):
 
     def _upgrade_room(
         self,
-        token: Optional[str] = None,
-        room_id: Optional[str] = None,
+        token: str | None = None,
+        room_id: str | None = None,
         expire_cache: bool = True,
     ) -> FakeChannel:
         if expire_cache:
diff --git a/tests/rest/client/utils.py b/tests/rest/client/utils.py
index bb214759d9..613c317b8a 100644
--- a/tests/rest/client/utils.py
+++ b/tests/rest/client/utils.py
@@ -30,14 +30,11 @@ from typing import (
     Any,
     AnyStr,
     Callable,
-    Dict,
     Iterable,
     Literal,
     Mapping,
     MutableMapping,
-    Optional,
     Sequence,
-    Tuple,
     overload,
 )
 from urllib.parse import urlencode
@@ -77,42 +74,42 @@ class RestHelper:
     hs: HomeServer
     reactor: MemoryReactorClock
     site: Site
-    auth_user_id: Optional[str]
+    auth_user_id: str | None
 
     @overload
     def create_room_as(
         self,
-        room_creator: Optional[str] = ...,
-        is_public: Optional[bool] = ...,
-        room_version: Optional[str] = ...,
-        tok: Optional[str] = ...,
+        room_creator: str | None = ...,
+        is_public: bool | None = ...,
+        room_version: str | None = ...,
+        tok: str | None = ...,
         expect_code: Literal[200] = ...,
-        extra_content: Optional[Dict] = ...,
-        custom_headers: Optional[Iterable[Tuple[AnyStr, AnyStr]]] = ...,
+        extra_content: dict | None = ...,
+        custom_headers: Iterable[tuple[AnyStr, AnyStr]] | None = ...,
     ) -> str: ...
 
     @overload
     def create_room_as(
         self,
-        room_creator: Optional[str] = ...,
-        is_public: Optional[bool] = ...,
-        room_version: Optional[str] = ...,
-        tok: Optional[str] = ...,
+        room_creator: str | None = ...,
+        is_public: bool | None = ...,
+        room_version: str | None = ...,
+        tok: str | None = ...,
         expect_code: int = ...,
-        extra_content: Optional[Dict] = ...,
-        custom_headers: Optional[Iterable[Tuple[AnyStr, AnyStr]]] = ...,
-    ) -> Optional[str]: ...
+        extra_content: dict | None = ...,
+        custom_headers: Iterable[tuple[AnyStr, AnyStr]] | None = ...,
+    ) -> str | None: ...
 
     def create_room_as(
         self,
-        room_creator: Optional[str] = None,
-        is_public: Optional[bool] = True,
-        room_version: Optional[str] = None,
-        tok: Optional[str] = None,
+        room_creator: str | None = None,
+        is_public: bool | None = True,
+        room_version: str | None = None,
+        tok: str | None = None,
         expect_code: int = HTTPStatus.OK,
-        extra_content: Optional[Dict] = None,
-        custom_headers: Optional[Iterable[Tuple[AnyStr, AnyStr]]] = None,
-    ) -> Optional[str]:
+        extra_content: dict | None = None,
+        custom_headers: Iterable[tuple[AnyStr, AnyStr]] | None = None,
+    ) -> str | None:
         """
         Create a room.
 
@@ -168,11 +165,11 @@ class RestHelper:
     def invite(
         self,
         room: str,
-        src: Optional[str] = None,
-        targ: Optional[str] = None,
+        src: str | None = None,
+        targ: str | None = None,
         expect_code: int = HTTPStatus.OK,
-        tok: Optional[str] = None,
-        extra_data: Optional[dict] = None,
+        tok: str | None = None,
+        extra_data: dict | None = None,
     ) -> JsonDict:
         return self.change_membership(
             room=room,
@@ -189,10 +186,10 @@ class RestHelper:
         room: str,
         user: str,
         expect_code: int = HTTPStatus.OK,
-        tok: Optional[str] = None,
-        appservice_user_id: Optional[str] = None,
-        expect_errcode: Optional[Codes] = None,
-        expect_additional_fields: Optional[dict] = None,
+        tok: str | None = None,
+        appservice_user_id: str | None = None,
+        expect_errcode: Codes | None = None,
+        expect_additional_fields: dict | None = None,
     ) -> JsonDict:
         return self.change_membership(
             room=room,
@@ -208,11 +205,11 @@ class RestHelper:
 
     def knock(
         self,
-        room: Optional[str] = None,
-        user: Optional[str] = None,
-        reason: Optional[str] = None,
+        room: str | None = None,
+        user: str | None = None,
+        reason: str | None = None,
         expect_code: int = HTTPStatus.OK,
-        tok: Optional[str] = None,
+        tok: str | None = None,
     ) -> None:
         temp_id = self.auth_user_id
         self.auth_user_id = user
@@ -243,9 +240,9 @@ class RestHelper:
     def leave(
         self,
         room: str,
-        user: Optional[str] = None,
+        user: str | None = None,
         expect_code: int = HTTPStatus.OK,
-        tok: Optional[str] = None,
+        tok: str | None = None,
     ) -> JsonDict:
         return self.change_membership(
             room=room,
@@ -262,7 +259,7 @@ class RestHelper:
         src: str,
         targ: str,
         expect_code: int = HTTPStatus.OK,
-        tok: Optional[str] = None,
+        tok: str | None = None,
     ) -> JsonDict:
         """A convenience helper: `change_membership` with `membership` preset to "ban"."""
         return self.change_membership(
@@ -277,15 +274,15 @@ class RestHelper:
     def change_membership(
         self,
         room: str,
-        src: Optional[str],
-        targ: Optional[str],
+        src: str | None,
+        targ: str | None,
         membership: str,
-        extra_data: Optional[dict] = None,
-        tok: Optional[str] = None,
-        appservice_user_id: Optional[str] = None,
+        extra_data: dict | None = None,
+        tok: str | None = None,
+        appservice_user_id: str | None = None,
         expect_code: int = HTTPStatus.OK,
-        expect_errcode: Optional[str] = None,
-        expect_additional_fields: Optional[dict] = None,
+        expect_errcode: str | None = None,
+        expect_additional_fields: dict | None = None,
     ) -> JsonDict:
         """
         Send a membership state event into a room.
@@ -310,7 +307,7 @@ class RestHelper:
         self.auth_user_id = src
 
         path = f"/_matrix/client/r0/rooms/{room}/state/m.room.member/{targ}"
-        url_params: Dict[str, str] = {}
+        url_params: dict[str, str] = {}
 
         if tok:
             url_params["access_token"] = tok
@@ -374,11 +371,11 @@ class RestHelper:
     def send(
         self,
         room_id: str,
-        body: Optional[str] = None,
-        txn_id: Optional[str] = None,
-        tok: Optional[str] = None,
+        body: str | None = None,
+        txn_id: str | None = None,
+        tok: str | None = None,
         expect_code: int = HTTPStatus.OK,
-        custom_headers: Optional[Iterable[Tuple[AnyStr, AnyStr]]] = None,
+        custom_headers: Iterable[tuple[AnyStr, AnyStr]] | None = None,
         type: str = "m.room.message",
     ) -> JsonDict:
         if body is None:
@@ -404,7 +401,7 @@ class RestHelper:
             "msgtype": "m.text",
             "body": f"Test event {idx}",
         },
-        tok: Optional[str] = None,
+        tok: str | None = None,
     ) -> Sequence[str]:
         """
         Helper to send a handful of sequential events and return their event IDs as a sequence.
@@ -426,11 +423,11 @@ class RestHelper:
         self,
         room_id: str,
         type: str,
-        content: Optional[dict] = None,
-        txn_id: Optional[str] = None,
-        tok: Optional[str] = None,
+        content: dict | None = None,
+        txn_id: str | None = None,
+        tok: str | None = None,
         expect_code: int = HTTPStatus.OK,
-        custom_headers: Optional[Iterable[Tuple[AnyStr, AnyStr]]] = None,
+        custom_headers: Iterable[tuple[AnyStr, AnyStr]] | None = None,
     ) -> JsonDict:
         if txn_id is None:
             txn_id = "m%s" % (str(time.time()))
@@ -460,7 +457,7 @@ class RestHelper:
         self,
         room_id: str,
         event_id: str,
-        tok: Optional[str] = None,
+        tok: str | None = None,
         expect_code: int = HTTPStatus.OK,
     ) -> JsonDict:
         """Request a specific event from the server.
@@ -497,8 +494,8 @@ class RestHelper:
         self,
         room_id: str,
         event_type: str,
-        body: Optional[Dict[str, Any]],
-        tok: Optional[str],
+        body: dict[str, Any] | None,
+        tok: str | None,
         expect_code: int = HTTPStatus.OK,
         state_key: str = "",
         method: str = "GET",
@@ -575,8 +572,8 @@ class RestHelper:
         self,
         room_id: str,
         event_type: str,
-        body: Dict[str, Any],
-        tok: Optional[str] = None,
+        body: dict[str, Any],
+        tok: str | None = None,
         expect_code: int = HTTPStatus.OK,
         state_key: str = "",
     ) -> JsonDict:
@@ -682,9 +679,9 @@ class RestHelper:
         fake_server: FakeOidcServer,
         remote_user_id: str,
         with_sid: bool = False,
-        idp_id: Optional[str] = None,
+        idp_id: str | None = None,
         expected_status: int = 200,
-    ) -> Tuple[JsonDict, FakeAuthorizationGrant]:
+    ) -> tuple[JsonDict, FakeAuthorizationGrant]:
         """Log in (as a new user) via OIDC
 
         Returns the result of the final token login and the fake authorization grant.
@@ -753,11 +750,11 @@ class RestHelper:
         self,
         fake_server: FakeOidcServer,
         user_info_dict: JsonDict,
-        client_redirect_url: Optional[str] = None,
-        ui_auth_session_id: Optional[str] = None,
+        client_redirect_url: str | None = None,
+        ui_auth_session_id: str | None = None,
         with_sid: bool = False,
-        idp_id: Optional[str] = None,
-    ) -> Tuple[FakeChannel, FakeAuthorizationGrant]:
+        idp_id: str | None = None,
+    ) -> tuple[FakeChannel, FakeAuthorizationGrant]:
         """Perform an OIDC authentication flow via a mock OIDC provider.
 
         This can be used for either login or user-interactive auth.
@@ -790,7 +787,7 @@ class RestHelper:
             went.
         """
 
-        cookies: Dict[str, str] = {}
+        cookies: dict[str, str] = {}
 
         with fake_server.patch_homeserver(hs=self.hs):
             # if we're doing a ui auth, hit the ui auth redirect endpoint
@@ -824,7 +821,7 @@ class RestHelper:
         cookies: Mapping[str, str],
         user_info_dict: JsonDict,
         with_sid: bool = False,
-    ) -> Tuple[FakeChannel, FakeAuthorizationGrant]:
+    ) -> tuple[FakeChannel, FakeAuthorizationGrant]:
         """Mock out an OIDC authentication flow
 
         Assumes that an OIDC auth has been initiated by one of initiate_sso_login or
@@ -880,9 +877,9 @@ class RestHelper:
 
     def initiate_sso_login(
         self,
-        client_redirect_url: Optional[str],
+        client_redirect_url: str | None,
         cookies: MutableMapping[str, str],
-        idp_id: Optional[str] = None,
+        idp_id: str | None = None,
     ) -> str:
         """Make a request to the login-via-sso redirect endpoint, and return the target
 
diff --git a/tests/rest/key/v2/test_remote_key_resource.py b/tests/rest/key/v2/test_remote_key_resource.py
index cf8241438c..aaf39e70e4 100644
--- a/tests/rest/key/v2/test_remote_key_resource.py
+++ b/tests/rest/key/v2/test_remote_key_resource.py
@@ -19,7 +19,7 @@
 #
 #
 from io import BytesIO, StringIO
-from typing import Any, Dict, Optional, Union
+from typing import Any
 from unittest.mock import Mock
 
 import signedjson.key
@@ -67,7 +67,7 @@ class BaseRemoteKeyResourceTestCase(unittest.HomeserverTestCase):
             path: str,
             ignore_backoff: bool = False,
             **kwargs: Any,
-        ) -> Union[JsonDict, list]:
+        ) -> JsonDict | list:
             self.assertTrue(ignore_backoff)
             self.assertEqual(destination, server_name)
             key_id = "%s:%s" % (signing_key.alg, signing_key.version)
@@ -156,7 +156,7 @@ class EndToEndPerspectivesTests(BaseRemoteKeyResourceTestCase):
     endpoint, to check that the two implementations are compatible.
     """
 
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         config = super().default_config()
 
         # replace the signing key with our own
@@ -170,7 +170,7 @@ class EndToEndPerspectivesTests(BaseRemoteKeyResourceTestCase):
     def prepare(self, reactor: MemoryReactor, clock: Clock, hs: HomeServer) -> None:
         # make a second homeserver, configured to use the first one as a key notary
         self.http_client2 = Mock()
-        config = default_config(name="keyclient")
+        config = default_config(server_name="keyclient")
         config["trusted_key_servers"] = [
             {
                 "server_name": self.hs.hostname,
@@ -191,8 +191,8 @@ class EndToEndPerspectivesTests(BaseRemoteKeyResourceTestCase):
         # wire up outbound POST /key/v2/query requests from hs2 so that they
         # will be forwarded to hs1
         async def post_json(
-            destination: str, path: str, data: Optional[JsonDict] = None
-        ) -> Union[JsonDict, list]:
+            destination: str, path: str, data: JsonDict | None = None
+        ) -> JsonDict | list:
             self.assertEqual(destination, self.hs.hostname)
             self.assertEqual(
                 path,
diff --git a/tests/rest/media/test_domain_blocking.py b/tests/rest/media/test_domain_blocking.py
index 9eb0222102..0bdbaa676d 100644
--- a/tests/rest/media/test_domain_blocking.py
+++ b/tests/rest/media/test_domain_blocking.py
@@ -18,7 +18,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Dict
 
 from twisted.internet.testing import MemoryReactor
 from twisted.web.resource import Resource
@@ -65,7 +64,7 @@ class MediaDomainBlockingTests(unittest.HomeserverTestCase):
             )
         )
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         # We need to manually set the resource tree to include media, the
         # default only does `/_matrix/client` APIs.
         return {"/_matrix/media": self.hs.get_media_repository_resource()}
diff --git a/tests/rest/media/test_url_preview.py b/tests/rest/media/test_url_preview.py
index 7c8d2fc998..32e78fc12a 100644
--- a/tests/rest/media/test_url_preview.py
+++ b/tests/rest/media/test_url_preview.py
@@ -22,7 +22,7 @@ import base64
 import json
 import os
 import re
-from typing import Any, Dict, Optional, Sequence, Tuple, Type
+from typing import Any, Sequence
 from urllib.parse import quote, urlencode
 
 from twisted.internet._resolver import HostResolution
@@ -127,7 +127,7 @@ class URLPreviewTests(unittest.HomeserverTestCase):
         assert self.media_repo.url_previewer is not None
         self.url_previewer = self.media_repo.url_previewer
 
-        self.lookups: Dict[str, Any] = {}
+        self.lookups: dict[str, Any] = {}
 
         class Resolver:
             def resolveHostName(
@@ -135,7 +135,7 @@ class URLPreviewTests(unittest.HomeserverTestCase):
                 resolutionReceiver: IResolutionReceiver,
                 hostName: str,
                 portNumber: int = 0,
-                addressTypes: Optional[Sequence[Type[IAddress]]] = None,
+                addressTypes: Sequence[type[IAddress]] | None = None,
                 transportSemantics: str = "TCP",
             ) -> IResolutionReceiver:
                 resolution = HostResolution(hostName)
@@ -150,7 +150,7 @@ class URLPreviewTests(unittest.HomeserverTestCase):
 
         self.reactor.nameResolver = Resolver()  # type: ignore[assignment]
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         """Create a resource tree for the test server
 
         A resource tree is a mapping from path to twisted.web.resource.
@@ -1227,7 +1227,7 @@ class URLPreviewTests(unittest.HomeserverTestCase):
         self.assertEqual(body["og:title"], "Test")
         self.assertNotIn("og:image", body)
 
-    def _download_image(self) -> Tuple[str, str]:
+    def _download_image(self) -> tuple[str, str]:
         """Downloads an image into the URL cache.
         Returns:
             A (host, media_id) tuple representing the MXC URI of the image.
diff --git a/tests/rest/synapse/client/test_federation_whitelist.py b/tests/rest/synapse/client/test_federation_whitelist.py
index f0067a8f2b..c4a990e32c 100644
--- a/tests/rest/synapse/client/test_federation_whitelist.py
+++ b/tests/rest/synapse/client/test_federation_whitelist.py
@@ -11,7 +11,6 @@
 # See the GNU Affero General Public License for more details:
 # <https://www.gnu.org/licenses/agpl-3.0.html>.
 
-from typing import Dict
 
 from twisted.web.resource import Resource
 
@@ -28,7 +27,7 @@ class FederationWhitelistTests(unittest.HomeserverTestCase):
         login.register_servlets,
     ]
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         base = super().create_resource_dict()
         base.update(build_synapse_client_resource_tree(self.hs))
         return base
diff --git a/tests/scripts/test_new_matrix_user.py b/tests/scripts/test_new_matrix_user.py
index cae096e72b..0e697427bb 100644
--- a/tests/scripts/test_new_matrix_user.py
+++ b/tests/scripts/test_new_matrix_user.py
@@ -18,7 +18,6 @@
 #
 #
 
-from typing import List, Optional
 from unittest.mock import Mock, patch
 
 from synapse._scripts.register_new_matrix_user import request_registration
@@ -34,14 +33,14 @@ class RegisterTestCase(TestCase):
         post that MAC.
         """
 
-        def get(url: str, verify: Optional[bool] = None) -> Mock:
+        def get(url: str, verify: bool | None = None) -> Mock:
             r = Mock()
             r.status_code = 200
             r.json = lambda: {"nonce": "a"}
             return r
 
         def post(
-            url: str, json: Optional[JsonDict] = None, verify: Optional[bool] = None
+            url: str, json: JsonDict | None = None, verify: bool | None = None
         ) -> Mock:
             # Make sure we are sent the correct info
             assert json is not None
@@ -60,8 +59,8 @@ class RegisterTestCase(TestCase):
         requests.post = post
 
         # The fake stdout will be written here
-        out: List[str] = []
-        err_code: List[int] = []
+        out: list[str] = []
+        err_code: list[int] = []
 
         with patch("synapse._scripts.register_new_matrix_user.requests", requests):
             request_registration(
@@ -85,7 +84,7 @@ class RegisterTestCase(TestCase):
         If the script fails to fetch a nonce, it throws an error and quits.
         """
 
-        def get(url: str, verify: Optional[bool] = None) -> Mock:
+        def get(url: str, verify: bool | None = None) -> Mock:
             r = Mock()
             r.status_code = 404
             r.reason = "Not Found"
@@ -96,8 +95,8 @@ class RegisterTestCase(TestCase):
         requests.get = get
 
         # The fake stdout will be written here
-        out: List[str] = []
-        err_code: List[int] = []
+        out: list[str] = []
+        err_code: list[int] = []
 
         with patch("synapse._scripts.register_new_matrix_user.requests", requests):
             request_registration(
@@ -123,14 +122,14 @@ class RegisterTestCase(TestCase):
         report an error and quit.
         """
 
-        def get(url: str, verify: Optional[bool] = None) -> Mock:
+        def get(url: str, verify: bool | None = None) -> Mock:
             r = Mock()
             r.status_code = 200
             r.json = lambda: {"nonce": "a"}
             return r
 
         def post(
-            url: str, json: Optional[JsonDict] = None, verify: Optional[bool] = None
+            url: str, json: JsonDict | None = None, verify: bool | None = None
         ) -> Mock:
             # Make sure we are sent the correct info
             assert json is not None
@@ -151,8 +150,8 @@ class RegisterTestCase(TestCase):
         requests.post = post
 
         # The fake stdout will be written here
-        out: List[str] = []
-        err_code: List[int] = []
+        out: list[str] = []
+        err_code: list[int] = []
 
         with patch("synapse._scripts.register_new_matrix_user.requests", requests):
             request_registration(
diff --git a/tests/server.py b/tests/server.py
index 858b41d56d..30337f3e38 100644
--- a/tests/server.py
+++ b/tests/server.py
@@ -28,21 +28,17 @@ import sqlite3
 import time
 import uuid
 import warnings
+import weakref
 from collections import deque
 from io import SEEK_END, BytesIO
 from typing import (
     Any,
     Awaitable,
     Callable,
-    Deque,
-    Dict,
     Iterable,
-    List,
     MutableMapping,
     Optional,
     Sequence,
-    Tuple,
-    Type,
     TypeVar,
     Union,
     cast,
@@ -56,7 +52,7 @@ from zope.interface import implementer
 
 import twisted
 from twisted.enterprise import adbapi
-from twisted.internet import address, tcp, threads, udp
+from twisted.internet import address, defer, tcp, threads, udp
 from twisted.internet._resolver import SimpleResolverComplexifier
 from twisted.internet.address import IPv4Address, IPv6Address
 from twisted.internet.defer import Deferred, fail, maybeDeferred, succeed
@@ -114,7 +110,6 @@ from tests.utils import (
     POSTGRES_USER,
     SQLITE_PERSIST_DB,
     USE_POSTGRES_FOR_TESTS,
-    MockClock,
     default_config,
 )
 
@@ -124,11 +119,11 @@ R = TypeVar("R")
 P = ParamSpec("P")
 
 # the type of thing that can be passed into `make_request` in the headers list
-CustomHeaderType = Tuple[Union[str, bytes], Union[str, bytes]]
+CustomHeaderType = tuple[str | bytes, str | bytes]
 
 # A pre-prepared SQLite DB that is used as a template when creating new SQLite
 # DB each test run. This dramatically speeds up test set up when using SQLite.
-PREPPED_SQLITE_DB_CONN: Optional[LoggingDatabaseConnection] = None
+PREPPED_SQLITE_DB_CONN: LoggingDatabaseConnection | None = None
 
 
 class TimedOutException(Exception):
@@ -151,9 +146,9 @@ class FakeChannel:
     _reactor: MemoryReactorClock
     result: dict = attr.Factory(dict)
     _ip: str = "127.0.0.1"
-    _producer: Optional[Union[IPullProducer, IPushProducer]] = None
-    resource_usage: Optional[ContextResourceUsage] = None
-    _request: Optional[Request] = None
+    _producer: IPullProducer | IPushProducer | None = None
+    resource_usage: ContextResourceUsage | None = None
+    _request: Request | None = None
 
     @property
     def request(self) -> Request:
@@ -172,7 +167,7 @@ class FakeChannel:
         return body
 
     @property
-    def json_list(self) -> List[JsonDict]:
+    def json_list(self) -> list[JsonDict]:
         body = json.loads(self.text_body)
         assert isinstance(body, list)
         return body
@@ -211,7 +206,7 @@ class FakeChannel:
         version: bytes,
         code: bytes,
         reason: bytes,
-        headers: Union[Headers, List[Tuple[bytes, bytes]]],
+        headers: Headers | list[tuple[bytes, bytes]],
     ) -> None:
         self.result["version"] = version
         self.result["code"] = code
@@ -253,7 +248,7 @@ class FakeChannel:
         # TODO This should ensure that the IProducer is an IPushProducer or
         # IPullProducer, unfortunately twisted.protocols.basic.FileSender does
         # implement those, but doesn't declare it.
-        self._producer = cast(Union[IPushProducer, IPullProducer], producer)
+        self._producer = cast(IPushProducer | IPullProducer, producer)
         self.producerStreaming = streaming
 
         def _produce() -> None:
@@ -362,18 +357,18 @@ class FakeSite:
 
 def make_request(
     reactor: MemoryReactorClock,
-    site: Union[Site, FakeSite],
-    method: Union[bytes, str],
-    path: Union[bytes, str],
-    content: Union[bytes, str, JsonDict] = b"",
-    access_token: Optional[str] = None,
-    request: Type[Request] = SynapseRequest,
+    site: Site | FakeSite,
+    method: bytes | str,
+    path: bytes | str,
+    content: bytes | str | JsonDict = b"",
+    access_token: str | None = None,
+    request: type[Request] = SynapseRequest,
     shorthand: bool = True,
-    federation_auth_origin: Optional[bytes] = None,
-    content_type: Optional[bytes] = None,
+    federation_auth_origin: bytes | None = None,
+    content_type: bytes | None = None,
     content_is_form: bool = False,
     await_result: bool = True,
-    custom_headers: Optional[Iterable[CustomHeaderType]] = None,
+    custom_headers: Iterable[CustomHeaderType] | None = None,
     client_ip: str = "127.0.0.1",
 ) -> FakeChannel:
     """
@@ -492,17 +487,17 @@ class ThreadedMemoryReactorClock(MemoryReactorClock):
     def __init__(self) -> None:
         self.threadpool = ThreadPool(self)
 
-        self._tcp_callbacks: Dict[Tuple[str, int], Callable] = {}
-        self._udp: List[udp.Port] = []
-        self.lookups: Dict[str, str] = {}
-        self._thread_callbacks: Deque[Callable[..., R]] = deque()
+        self._tcp_callbacks: dict[tuple[str, int], Callable] = {}
+        self._udp: list[udp.Port] = []
+        self.lookups: dict[str, str] = {}
+        self._thread_callbacks: deque[Callable[..., R]] = deque()
 
         lookups = self.lookups
 
         @implementer(IResolverSimple)
         class FakeResolver:
             def getHostByName(
-                self, name: str, timeout: Optional[Sequence[int]] = None
+                self, name: str, timeout: Sequence[int] | None = None
             ) -> "Deferred[str]":
                 if name not in lookups:
                     return fail(DNSLookupError("OH NO: unknown %s" % (name,)))
@@ -525,6 +520,19 @@ class ThreadedMemoryReactorClock(MemoryReactorClock):
         # overwrite it again.
         self.nameResolver = SimpleResolverComplexifier(FakeResolver())
 
+    def run(self) -> None:
+        """
+        Override the call from `MemoryReactorClock` to add an additional step that
+        cleans up any `whenRunningHooks` that have been called.
+        This is necessary for a clean shutdown to occur as these hooks can hold
+        references to the `SynapseHomeServer`.
+        """
+        super().run()
+
+        # `MemoryReactorClock` never clears the hooks that have already been called.
+        # So manually clear the hooks here after they have been run.
+        self.whenRunningHooks.clear()
+
     def installNameResolver(self, resolver: IHostnameResolver) -> IHostnameResolver:
         raise NotImplementedError()
 
@@ -609,7 +617,7 @@ class ThreadedMemoryReactorClock(MemoryReactorClock):
         port: int,
         factory: ClientFactory,
         timeout: float = 30,
-        bindAddress: Optional[Tuple[str, int]] = None,
+        bindAddress: tuple[str, int] | None = None,
     ) -> IConnector:
         """Fake L{IReactorTCP.connectTCP}."""
 
@@ -650,6 +658,19 @@ class ThreadedMemoryReactorClock(MemoryReactorClock):
             super().advance(0)
 
 
+def cleanup_test_reactor_system_event_triggers(
+    reactor: ThreadedMemoryReactorClock,
+) -> None:
+    """Cleanup any registered system event triggers.
+    The `twisted.internet.test.ThreadedMemoryReactor` does not implement
+    `removeSystemEventTrigger` so won't clean these triggers up on it's own properly.
+    When trying to override `removeSystemEventTrigger` in `ThreadedMemoryReactorClock`
+    in order to implement this functionality, twisted complains about the reactor being
+    unclean and fails some tests.
+    """
+    reactor.triggers.clear()
+
+
 def validate_connector(connector: tcp.Connector, expected_ip: str) -> None:
     """Try to validate the obtained connector as it would happen when
     synapse is running and the conection will be established.
@@ -767,7 +788,7 @@ class ThreadPool:
 
     def callInThreadWithCallback(
         self,
-        onResult: Callable[[bool, Union[Failure, R]], None],
+        onResult: Callable[[bool, Failure | R], None],
         function: Callable[P, R],
         *args: P.args,
         **kwargs: P.kwargs,
@@ -781,14 +802,19 @@ class ThreadPool:
         d: "Deferred[None]" = Deferred()
         d.addCallback(lambda x: function(*args, **kwargs))
         d.addBoth(_)
-        self._reactor.callLater(0, d.callback, True)
+        # mypy ignored here because:
+        #   - this is part of the test infrastructure (outside of Synapse) so tracking
+        #     these calls for for homeserver shutdown doesn't make sense.
+        self._reactor.callLater(0, d.callback, True)  # type: ignore[call-later-not-tracked]
         return d
 
 
-def get_clock() -> Tuple[ThreadedMemoryReactorClock, Clock]:
-    clock = ThreadedMemoryReactorClock()
-    hs_clock = Clock(clock, server_name="test_server")
-    return clock, hs_clock
+def get_clock() -> tuple[ThreadedMemoryReactorClock, Clock]:
+    # Ignore the linter error since this is an expected usage of creating a `Clock` for
+    # testing purposes.
+    reactor = ThreadedMemoryReactorClock()
+    hs_clock = Clock(reactor, server_name="test_server")  # type: ignore[multiple-internal-clocks]
+    return reactor, hs_clock
 
 
 @implementer(ITCPTransport)
@@ -815,17 +841,17 @@ class FakeTransport:
     """Test reactor
     """
 
-    _protocol: Optional[IProtocol] = None
+    _protocol: IProtocol | None = None
     """The Protocol which is producing data for this transport. Optional, but if set
     will get called back for connectionLost() notifications etc.
     """
 
-    _peer_address: Union[IPv4Address, IPv6Address] = attr.Factory(
+    _peer_address: IPv4Address | IPv6Address = attr.Factory(
         lambda: address.IPv4Address("TCP", "127.0.0.1", 5678)
     )
     """The value to be returned by getPeer"""
 
-    _host_address: Union[IPv4Address, IPv6Address] = attr.Factory(
+    _host_address: IPv4Address | IPv6Address = attr.Factory(
         lambda: address.IPv4Address("TCP", "127.0.0.1", 1234)
     )
     """The value to be returned by getHost"""
@@ -834,13 +860,13 @@ class FakeTransport:
     disconnected = False
     connected = True
     buffer: bytes = b""
-    producer: Optional[IPushProducer] = None
+    producer: IPushProducer | None = None
     autoflush: bool = True
 
-    def getPeer(self) -> Union[IPv4Address, IPv6Address]:
+    def getPeer(self) -> IPv4Address | IPv6Address:
         return self._peer_address
 
-    def getHost(self) -> Union[IPv4Address, IPv6Address]:
+    def getHost(self) -> IPv4Address | IPv6Address:
         return self._host_address
 
     def loseConnection(self) -> None:
@@ -899,10 +925,16 @@ class FakeTransport:
             # some implementations of IProducer (for example, FileSender)
             # don't return a deferred.
             d = maybeDeferred(self.producer.resumeProducing)
-            d.addCallback(lambda x: self._reactor.callLater(0.1, _produce))
+            # mypy ignored here because:
+            #   - this is part of the test infrastructure (outside of Synapse) so tracking
+            #     these calls for for homeserver shutdown doesn't make sense.
+            d.addCallback(lambda x: self._reactor.callLater(0.1, _produce))  # type: ignore[call-later-not-tracked,call-overload]
 
         if not streaming:
-            self._reactor.callLater(0.0, _produce)
+            # mypy ignored here because:
+            #   - this is part of the test infrastructure (outside of Synapse) so tracking
+            #     these calls for for homeserver shutdown doesn't make sense.
+            self._reactor.callLater(0.0, _produce)  # type: ignore[call-later-not-tracked]
 
     def write(self, byt: bytes) -> None:
         if self.disconnecting:
@@ -914,13 +946,16 @@ class FakeTransport:
         # TLSMemoryBIOProtocol) get very confused if a read comes back while they are
         # still doing a write. Doing a callLater here breaks the cycle.
         if self.autoflush:
-            self._reactor.callLater(0.0, self.flush)
+            # mypy ignored here because:
+            #   - this is part of the test infrastructure (outside of Synapse) so tracking
+            #     these calls for for homeserver shutdown doesn't make sense.
+            self._reactor.callLater(0.0, self.flush)  # type: ignore[call-later-not-tracked]
 
     def writeSequence(self, seq: Iterable[bytes]) -> None:
         for x in seq:
             self.write(x)
 
-    def flush(self, maxbytes: Optional[int] = None) -> None:
+    def flush(self, maxbytes: int | None = None) -> None:
         if not self.buffer:
             # nothing to do. Don't write empty buffers: it upsets the
             # TLSMemoryBIOProtocol
@@ -944,7 +979,10 @@ class FakeTransport:
 
         self.buffer = self.buffer[len(to_write) :]
         if self.buffer and self.autoflush:
-            self._reactor.callLater(0.0, self.flush)
+            # mypy ignored here because:
+            #   - this is part of the test infrastructure (outside of Synapse) so tracking
+            #     these calls for for homeserver shutdown doesn't make sense.
+            self._reactor.callLater(0.0, self.flush)  # type: ignore[call-later-not-tracked]
 
         if not self.buffer and self.disconnecting:
             logger.info("FakeTransport: Buffer now empty, completing disconnect")
@@ -998,7 +1036,7 @@ class FakeTransport:
 
 def connect_client(
     reactor: ThreadedMemoryReactorClock, client_id: int
-) -> Tuple[IProtocol, AccumulatingProtocol]:
+) -> tuple[IProtocol, AccumulatingProtocol]:
     """
     Connect a client to a fake TCP transport.
 
@@ -1020,12 +1058,14 @@ class TestHomeServer(HomeServer):
 
 
 def setup_test_homeserver(
-    cleanup_func: Callable[[Callable[[], None]], None],
-    name: str = "test",
-    config: Optional[HomeServerConfig] = None,
-    reactor: Optional[ISynapseReactor] = None,
-    homeserver_to_use: Type[HomeServer] = TestHomeServer,
-    **kwargs: Any,
+    *,
+    cleanup_func: Callable[[Callable[[], Optional["Deferred[None]"]]], None],
+    server_name: str = "test",
+    config: HomeServerConfig | None = None,
+    reactor: ISynapseReactor | None = None,
+    homeserver_to_use: type[HomeServer] = TestHomeServer,
+    db_txn_limit: int | None = None,
+    **extra_homeserver_attributes: Any,
 ) -> HomeServer:
     """
     Setup a homeserver suitable for running tests against.  Keyword arguments
@@ -1035,28 +1075,44 @@ def setup_test_homeserver(
 
     Args:
         cleanup_func : The function used to register a cleanup routine for
-                       after the test.
+                       after the test. If the function returns a Deferred, the
+                       test case will wait until the Deferred has fired before
+                       proceeding to the next cleanup function.
+        server_name: Homeserver name
+        config: Homeserver config
+        reactor: Twisted reactor
+        homeserver_to_use: Homeserver class to instantiate.
+        db_txn_limit: Gives the maximum number of database transactions to run per
+            connection before reconnecting. 0 means no limit. If unset, defaults to None
+            here which will default upstream to `0`.
+        **extra_homeserver_attributes: Additional keyword arguments to install as
+            `@cache_in_self` attributes on the homeserver. For example, `clock` will be
+            installed as `hs._clock`.
 
     Calling this method directly is deprecated: you should instead derive from
     HomeserverTestCase.
     """
     if reactor is None:
-        from twisted.internet import reactor as _reactor
-
-        reactor = cast(ISynapseReactor, _reactor)
+        reactor = ThreadedMemoryReactorClock()
 
     if config is None:
-        config = default_config(name, parse=True)
+        config = default_config(server_name, parse=True)
+
+    server_name = config.server.server_name
+    if not isinstance(server_name, str):
+        raise ConfigError("Must be a string", ("server_name",))
+
+    if "clock" not in extra_homeserver_attributes:
+        # Ignore `multiple-internal-clocks` linter error here since we are creating a `Clock`
+        # for testing purposes (i.e. outside of Synapse).
+        extra_homeserver_attributes["clock"] = Clock(reactor, server_name=server_name)  # type: ignore[multiple-internal-clocks]
 
     config.caches.resize_all_caches()
 
-    if "clock" not in kwargs:
-        kwargs["clock"] = MockClock()
-
     if USE_POSTGRES_FOR_TESTS:
         test_db = "synapse_test_%s" % uuid.uuid4().hex
 
-        database_config = {
+        database_config: JsonDict = {
             "name": "psycopg2",
             "args": {
                 "dbname": test_db,
@@ -1088,10 +1144,6 @@ def setup_test_homeserver(
             "args": {"database": test_db_location, "cp_min": 1, "cp_max": 1},
         }
 
-        server_name = config.server.server_name
-        if not isinstance(server_name, str):
-            raise ConfigError("Must be a string", ("server_name",))
-
         # Check if we have set up a DB that we can use as a template.
         global PREPPED_SQLITE_DB_CONN
         if PREPPED_SQLITE_DB_CONN is None:
@@ -1111,8 +1163,8 @@ def setup_test_homeserver(
 
         database_config["_TEST_PREPPED_CONN"] = PREPPED_SQLITE_DB_CONN
 
-    if "db_txn_limit" in kwargs:
-        database_config["txn_limit"] = kwargs["db_txn_limit"]
+    if db_txn_limit is not None:
+        database_config["txn_limit"] = db_txn_limit
 
     database = DatabaseConnectionConfig("master", database_config)
     config.database.databases = [database]
@@ -1139,17 +1191,29 @@ def setup_test_homeserver(
         db_conn.close()
 
     hs = homeserver_to_use(
-        name,
+        server_name,
         config=config,
-        version_string="Synapse/tests",
         reactor=reactor,
     )
 
-    # Register the cleanup hook
-    cleanup_func(hs.cleanup)
+    # Capture the `hs` as a `weakref` here to ensure there is no scenario where uncalled
+    # cleanup functions result in holding the `hs` in memory.
+    cleanup_hs_ref = weakref.ref(hs)
+
+    def shutdown_hs_on_cleanup() -> "Deferred[None]":
+        cleanup_hs = cleanup_hs_ref()
+        deferred: "Deferred[None]" = defer.succeed(None)
+        if cleanup_hs is not None:
+            deferred = defer.ensureDeferred(cleanup_hs.shutdown())
+        return deferred
+
+    # Register the cleanup hook for the homeserver.
+    # A full `hs.shutdown()` is necessary otherwise CI tests will fail while exhibiting
+    # strange behaviours.
+    cleanup_func(shutdown_hs_on_cleanup)
 
     # Install @cache_in_self attributes
-    for key, val in kwargs.items():
+    for key, val in extra_homeserver_attributes.items():
         setattr(hs, "_" + key, val)
 
     # Mock TLS
@@ -1175,14 +1239,18 @@ def setup_test_homeserver(
     hs.get_datastores().main.USE_DEDICATED_DB_THREADS_FOR_EVENT_FETCHING = False
 
     if USE_POSTGRES_FOR_TESTS:
-        database_pool = hs.get_datastores().databases[0]
+        # Capture the `database_pool` as a `weakref` here to ensure there is no scenario where uncalled
+        # cleanup functions result in holding the `hs` in memory.
+        database_pool = weakref.ref(hs.get_datastores().databases[0])
 
         # We need to do cleanup on PostgreSQL
         def cleanup() -> None:
             import psycopg2
 
             # Close all the db pools
-            database_pool._db_pool.close()
+            db_pool = database_pool()
+            if db_pool is not None:
+                db_pool._db_pool.close()
 
             dropped = False
 
diff --git a/tests/server_notices/test_resource_limits_server_notices.py b/tests/server_notices/test_resource_limits_server_notices.py
index dd38528a7d..a0c5582496 100644
--- a/tests/server_notices/test_resource_limits_server_notices.py
+++ b/tests/server_notices/test_resource_limits_server_notices.py
@@ -17,7 +17,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Tuple
 from unittest.mock import AsyncMock, Mock
 
 from twisted.internet.testing import MemoryReactor
@@ -363,7 +362,7 @@ class TestResourceLimitsServerNoticesWithRealRooms(unittest.HomeserverTestCase):
 
         self.assertTrue(notice_in_room, "No server notice in room")
 
-    def _trigger_notice_and_join(self) -> Tuple[str, str, str]:
+    def _trigger_notice_and_join(self) -> tuple[str, str, str]:
         """Creates enough active users to hit the MAU limit and trigger a system notice
         about it, then joins the system notices room with one of the users created.
 
diff --git a/tests/state/test_v2.py b/tests/state/test_v2.py
index b4f2b98cc4..7db710846d 100644
--- a/tests/state/test_v2.py
+++ b/tests/state/test_v2.py
@@ -21,13 +21,8 @@
 import itertools
 from typing import (
     Collection,
-    Dict,
     Iterable,
-    List,
     Mapping,
-    Optional,
-    Set,
-    Tuple,
     TypeVar,
 )
 
@@ -83,7 +78,7 @@ class FakeEvent:
         id: str,
         sender: str,
         type: str,
-        state_key: Optional[str],
+        state_key: str | None,
         content: Mapping[str, object],
     ):
         self.node_id = id
@@ -94,7 +89,7 @@ class FakeEvent:
         self.content = content
         self.room_id = ROOM_ID
 
-    def to_event(self, auth_events: List[str], prev_events: List[str]) -> EventBase:
+    def to_event(self, auth_events: list[str], prev_events: list[str]) -> EventBase:
         """Given the auth_events and prev_events, convert to a Frozen Event
 
         Args:
@@ -461,9 +456,9 @@ class StateTestCase(unittest.TestCase):
 
     def do_check(
         self,
-        events: List[FakeEvent],
-        edges: List[List[str]],
-        expected_state_ids: List[str],
+        events: list[FakeEvent],
+        edges: list[list[str]],
+        expected_state_ids: list[str],
     ) -> None:
         """Take a list of events and edges and calculate the state of the
         graph at END, and asserts it matches `expected_state_ids`
@@ -476,9 +471,9 @@ class StateTestCase(unittest.TestCase):
                 the keys that haven't changed since START).
         """
         # We want to sort the events into topological order for processing.
-        graph: Dict[str, Set[str]] = {}
+        graph: dict[str, set[str]] = {}
 
-        fake_event_map: Dict[str, FakeEvent] = {}
+        fake_event_map: dict[str, FakeEvent] = {}
 
         for ev in itertools.chain(INITIAL_EVENTS, events):
             graph[ev.node_id] = set()
@@ -491,8 +486,8 @@ class StateTestCase(unittest.TestCase):
             for a, b in pairwise(edge_list):
                 graph[a].add(b)
 
-        event_map: Dict[str, EventBase] = {}
-        state_at_event: Dict[str, StateMap[str]] = {}
+        event_map: dict[str, EventBase] = {}
+        state_at_event: dict[str, StateMap[str]] = {}
 
         # We copy the map as the sort consumes the graph
         graph_copy = {k: set(v) for k, v in graph.items()}
@@ -529,7 +524,7 @@ class StateTestCase(unittest.TestCase):
             #    EventBuilder. But this is Hard because the relevant attributes are
             #    DictProperty[T] descriptors on EventBase but normal Ts on FakeEvent.
             # 2. Define a `GenericEvent` Protocol describing `FakeEvent` only, and
-            #    change this function to accept Union[Event, EventBase, EventBuilder].
+            #    change this function to accept Event | EventBase | EventBuilder.
             #    This seems reasonable to me, but mypy isn't happy. I think that's
             #    a mypy bug, see https://github.com/python/mypy/issues/5570
             # Instead, resort to a type-ignore.
@@ -568,7 +563,7 @@ class StateTestCase(unittest.TestCase):
 
 class LexicographicalTestCase(unittest.TestCase):
     def test_simple(self) -> None:
-        graph: Dict[str, Set[str]] = {
+        graph: dict[str, set[str]] = {
             "l": {"o"},
             "m": {"n", "o"},
             "n": {"o"},
@@ -1020,7 +1015,7 @@ class AuthChainDifferenceTestCase(unittest.TestCase):
 T = TypeVar("T")
 
 
-def pairwise(iterable: Iterable[T]) -> Iterable[Tuple[T, T]]:
+def pairwise(iterable: Iterable[T]) -> Iterable[tuple[T, T]]:
     "s -> (s0,s1), (s1,s2), (s2, s3), ..."
     a, b = itertools.tee(iterable)
     next(b, None)
@@ -1029,11 +1024,11 @@ def pairwise(iterable: Iterable[T]) -> Iterable[Tuple[T, T]]:
 
 @attr.s
 class TestStateResolutionStore:
-    event_map: Dict[str, EventBase] = attr.ib()
+    event_map: dict[str, EventBase] = attr.ib()
 
     def get_events(
         self, event_ids: Collection[str], allow_rejected: bool = False
-    ) -> "defer.Deferred[Dict[str, EventBase]]":
+    ) -> "defer.Deferred[dict[str, EventBase]]":
         """Get events from the database
 
         Args:
@@ -1048,7 +1043,7 @@ class TestStateResolutionStore:
             {eid: self.event_map[eid] for eid in event_ids if eid in self.event_map}
         )
 
-    def _get_auth_chain(self, event_ids: Iterable[str]) -> List[str]:
+    def _get_auth_chain(self, event_ids: Iterable[str]) -> list[str]:
         """Gets the full auth chain for a set of events (including rejected
         events).
 
@@ -1085,9 +1080,9 @@ class TestStateResolutionStore:
     def get_auth_chain_difference(
         self,
         room_id: str,
-        auth_sets: List[Set[str]],
-        conflicted_state: Optional[Set[str]],
-        additional_backwards_reachable_conflicted_events: Optional[Set[str]],
+        auth_sets: list[set[str]],
+        conflicted_state: set[str] | None,
+        additional_backwards_reachable_conflicted_events: set[str] | None,
     ) -> "defer.Deferred[StateDifference]":
         chains = [frozenset(self._get_auth_chain(a)) for a in auth_sets]
 
diff --git a/tests/state/test_v21.py b/tests/state/test_v21.py
index ff1715d4f7..b17773fb56 100644
--- a/tests/state/test_v21.py
+++ b/tests/state/test_v21.py
@@ -18,7 +18,7 @@
 #
 #
 import itertools
-from typing import Dict, List, Optional, Sequence, Set
+from typing import Sequence
 
 from twisted.internet import defer
 from twisted.test.proto_helpers import MemoryReactor
@@ -357,11 +357,11 @@ class StateResV21TestCase(unittest.HomeserverTestCase):
         self,
         room_id: str,
         state_maps: Sequence[StateMap[str]],
-        event_map: Optional[Dict[str, EventBase]],
+        event_map: dict[str, EventBase] | None,
         state_res_store: StateResolutionStoreInterface,
-    ) -> Set[str]:
+    ) -> set[str]:
         _, conflicted_state = _seperate(state_maps)
-        conflicted_set: Optional[Set[str]] = set(
+        conflicted_set: set[str] | None = set(
             itertools.chain.from_iterable(conflicted_state.values())
         )
         if event_map is None:
@@ -377,7 +377,7 @@ class StateResV21TestCase(unittest.HomeserverTestCase):
     def get_resolution_and_verify_expected(
         self,
         state_maps: Sequence[StateMap[str]],
-        events: List[EventBase],
+        events: list[EventBase],
         expected: StateMap[str],
     ) -> None:
         room_id = events[0].room_id
@@ -458,7 +458,7 @@ class StateResV21TestCase(unittest.HomeserverTestCase):
             resolve_and_check()
 
     def persist_event(
-        self, event: EventBase, state: Optional[StateMap[str]] = None
+        self, event: EventBase, state: StateMap[str] | None = None
     ) -> None:
         """Persist the event, with optional state"""
         context = self.get_success(
@@ -473,12 +473,12 @@ class StateResV21TestCase(unittest.HomeserverTestCase):
     def create_event(
         self,
         event_type: str,
-        state_key: Optional[str],
+        state_key: str | None,
         sender: str,
-        content: Dict,
-        auth_events: List[str],
-        prev_events: Optional[List[str]] = None,
-        room_id: Optional[str] = None,
+        content: dict,
+        auth_events: list[str],
+        prev_events: list[str] | None = None,
+        room_id: str | None = None,
     ) -> EventBase:
         """Short-hand for event_from_pdu_json for fields we typically care about.
         Tests can override by just calling event_from_pdu_json directly."""
diff --git a/tests/storage/databases/main/test_end_to_end_keys.py b/tests/storage/databases/main/test_end_to_end_keys.py
index d0dd8f866b..d21dac6024 100644
--- a/tests/storage/databases/main/test_end_to_end_keys.py
+++ b/tests/storage/databases/main/test_end_to_end_keys.py
@@ -18,7 +18,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import List, Optional, Tuple
 
 from twisted.internet.testing import MemoryReactor
 
@@ -99,7 +98,7 @@ class EndToEndKeyWorkerStoreTestCase(HomeserverTestCase):
 
         def check_timestamp_column(
             txn: LoggingTransaction,
-        ) -> List[Tuple[JsonDict, Optional[int]]]:
+        ) -> list[tuple[JsonDict, int | None]]:
             """Fetch all rows for Alice's keys."""
             txn.execute(
                 """
diff --git a/tests/storage/databases/main/test_events_worker.py b/tests/storage/databases/main/test_events_worker.py
index a7c6bdd9b4..c786271c09 100644
--- a/tests/storage/databases/main/test_events_worker.py
+++ b/tests/storage/databases/main/test_events_worker.py
@@ -20,7 +20,7 @@
 #
 import json
 from contextlib import contextmanager
-from typing import Generator, List, Set, Tuple
+from typing import Generator
 from unittest import mock
 
 from twisted.enterprise.adbapi import ConnectionPool
@@ -60,7 +60,7 @@ class HaveSeenEventsTestCase(unittest.HomeserverTestCase):
         self.token = self.login(self.user, "pass")
         self.room_id = self.helper.create_room_as(self.user, tok=self.token)
 
-        self.event_ids: List[str] = []
+        self.event_ids: list[str] = []
         for i in range(3):
             event = self.get_success(
                 inject_event(
@@ -316,7 +316,7 @@ class GetEventsTestCase(unittest.HomeserverTestCase):
 
         room_id = self.helper.create_room_as(user_id, tok=user_tok)
 
-        event_ids: Set[str] = set()
+        event_ids: set[str] = set()
         for i in range(num_events):
             event = self.get_success(
                 inject_event(
@@ -371,7 +371,7 @@ class DatabaseOutageTestCase(unittest.HomeserverTestCase):
             )
         )
 
-        self.event_ids: List[str] = []
+        self.event_ids: list[str] = []
         for idx in range(1, 21):  # Stream ordering starts at 1.
             event_json = {
                 "type": f"test {idx}",
@@ -504,7 +504,7 @@ class GetEventCancellationTestCase(unittest.HomeserverTestCase):
     def blocking_get_event_calls(
         self,
     ) -> Generator[
-        Tuple["Deferred[None]", "Deferred[None]", "Deferred[None]"], None, None
+        tuple["Deferred[None]", "Deferred[None]", "Deferred[None]"], None, None
     ]:
         """Starts two concurrent `get_event` calls for the same event.
 
diff --git a/tests/storage/databases/main/test_receipts.py b/tests/storage/databases/main/test_receipts.py
index d084f5c2ba..be29e0a7f4 100644
--- a/tests/storage/databases/main/test_receipts.py
+++ b/tests/storage/databases/main/test_receipts.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import Any, Dict, Optional, Sequence, Tuple
+from typing import Any, Sequence
 
 from twisted.internet.testing import MemoryReactor
 
@@ -51,8 +51,8 @@ class ReceiptsBackgroundUpdateStoreTestCase(HomeserverTestCase):
         update_name: str,
         index_name: str,
         table: str,
-        receipts: Dict[Tuple[str, str, str], Sequence[Dict[str, Any]]],
-        expected_unique_receipts: Dict[Tuple[str, str, str], Optional[Dict[str, Any]]],
+        receipts: dict[tuple[str, str, str], Sequence[dict[str, Any]]],
+        expected_unique_receipts: dict[tuple[str, str, str], dict[str, Any] | None],
     ) -> None:
         """Test that the background update to uniqueify non-thread receipts in
         the given receipts table works properly.
diff --git a/tests/storage/test__base.py b/tests/storage/test__base.py
index 5e773a5545..5602531880 100644
--- a/tests/storage/test__base.py
+++ b/tests/storage/test__base.py
@@ -20,7 +20,7 @@
 #
 
 import secrets
-from typing import Generator, List, Tuple, cast
+from typing import Generator, cast
 
 from twisted.internet.testing import MemoryReactor
 
@@ -52,9 +52,9 @@ class UpdateUpsertManyTests(unittest.HomeserverTestCase):
             )
         )
 
-    def _dump_table_to_tuple(self) -> Generator[Tuple[int, str, str], None, None]:
+    def _dump_table_to_tuple(self) -> Generator[tuple[int, str, str], None, None]:
         yield from cast(
-            List[Tuple[int, str, str]],
+            list[tuple[int, str, str]],
             self.get_success(
                 self.storage.db_pool.simple_select_list(
                     self.table_name, None, ["id, username, value"]
diff --git a/tests/storage/test_account_data.py b/tests/storage/test_account_data.py
index 13c4be988e..c91aad097d 100644
--- a/tests/storage/test_account_data.py
+++ b/tests/storage/test_account_data.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import Iterable, Optional, Set
+from typing import Iterable
 
 from twisted.internet.testing import MemoryReactor
 
@@ -37,7 +37,7 @@ class IgnoredUsersTestCase(unittest.HomeserverTestCase):
         self.user = "@user:test"
 
     def _update_ignore_list(
-        self, *ignored_user_ids: Iterable[str], ignorer_user_id: Optional[str] = None
+        self, *ignored_user_ids: Iterable[str], ignorer_user_id: str | None = None
     ) -> None:
         """Update the account data to block the given users."""
         if ignorer_user_id is None:
@@ -52,7 +52,7 @@ class IgnoredUsersTestCase(unittest.HomeserverTestCase):
         )
 
     def assert_ignorers(
-        self, ignored_user_id: str, expected_ignorer_user_ids: Set[str]
+        self, ignored_user_id: str, expected_ignorer_user_ids: set[str]
     ) -> None:
         self.assertEqual(
             self.get_success(self.store.ignored_by(ignored_user_id)),
@@ -60,7 +60,7 @@ class IgnoredUsersTestCase(unittest.HomeserverTestCase):
         )
 
     def assert_ignored(
-        self, ignorer_user_id: str, expected_ignored_user_ids: Set[str]
+        self, ignorer_user_id: str, expected_ignored_user_ids: set[str]
     ) -> None:
         self.assertEqual(
             self.get_success(self.store.ignored_users(ignorer_user_id)),
@@ -167,7 +167,7 @@ class IgnoredUsersTestCase(unittest.HomeserverTestCase):
         """Test that ignoring users updates the latest stream ID for the ignored
         user list account data."""
 
-        def get_latest_ignore_streampos(user_id: str) -> Optional[int]:
+        def get_latest_ignore_streampos(user_id: str) -> int | None:
             return self.get_success(
                 self.store.get_latest_stream_id_for_global_account_data_by_type_for_user(
                     user_id, AccountDataTypes.IGNORED_USER_LIST
diff --git a/tests/storage/test_appservice.py b/tests/storage/test_appservice.py
index b4df92c7a1..4b9d069d6a 100644
--- a/tests/storage/test_appservice.py
+++ b/tests/storage/test_appservice.py
@@ -21,7 +21,7 @@
 import json
 import os
 import tempfile
-from typing import List, cast
+from typing import cast
 from unittest.mock import AsyncMock, Mock
 
 import yaml
@@ -48,7 +48,7 @@ class ApplicationServiceStoreTestCase(unittest.HomeserverTestCase):
     def setUp(self) -> None:
         super().setUp()
 
-        self.as_yaml_files: List[str] = []
+        self.as_yaml_files: list[str] = []
 
         self.hs.config.appservice.app_service_config_files = self.as_yaml_files
         self.hs.config.caches.event_cache_size = 1
@@ -123,7 +123,7 @@ class ApplicationServiceStoreTestCase(unittest.HomeserverTestCase):
 class ApplicationServiceTransactionStoreTestCase(unittest.HomeserverTestCase):
     def setUp(self) -> None:
         super().setUp()
-        self.as_yaml_files: List[str] = []
+        self.as_yaml_files: list[str] = []
 
         self.hs.config.appservice.app_service_config_files = self.as_yaml_files
         self.hs.config.caches.event_cache_size = 1
@@ -180,7 +180,7 @@ class ApplicationServiceTransactionStoreTestCase(unittest.HomeserverTestCase):
         )
 
     def _insert_txn(
-        self, as_id: str, txn_id: int, events: List[Mock]
+        self, as_id: str, txn_id: int, events: list[Mock]
     ) -> "defer.Deferred[None]":
         return self.db_pool.runOperation(
             self.engine.convert_param_style(
@@ -277,7 +277,7 @@ class ApplicationServiceTransactionStoreTestCase(unittest.HomeserverTestCase):
         self,
     ) -> None:
         service = Mock(id=self.as_list[0]["id"])
-        events = cast(List[EventBase], [Mock(event_id="e1"), Mock(event_id="e2")])
+        events = cast(list[EventBase], [Mock(event_id="e1"), Mock(event_id="e2")])
         txn = self.get_success(
             defer.ensureDeferred(
                 self.store.create_appservice_txn(
diff --git a/tests/storage/test_background_update.py b/tests/storage/test_background_update.py
index cf63b50c2f..3505423691 100644
--- a/tests/storage/test_background_update.py
+++ b/tests/storage/test_background_update.py
@@ -19,7 +19,7 @@
 #
 #
 import logging
-from typing import List, Tuple, cast
+from typing import cast
 from unittest.mock import AsyncMock, Mock
 
 import yaml
@@ -535,7 +535,7 @@ class BackgroundUpdateValidateConstraintTestCase(unittest.HomeserverTestCase):
 
         # Check the correct values are in the new table.
         rows = cast(
-            List[Tuple[int, int]],
+            list[tuple[int, int]],
             self.get_success(
                 self.store.db_pool.simple_select_list(
                     table="test_constraint",
@@ -652,7 +652,7 @@ class BackgroundUpdateValidateConstraintTestCase(unittest.HomeserverTestCase):
 
         # Check the correct values are in the new table.
         rows = cast(
-            List[Tuple[int, int]],
+            list[tuple[int, int]],
             self.get_success(
                 self.store.db_pool.simple_select_list(
                     table="test_constraint",
diff --git a/tests/storage/test_base.py b/tests/storage/test_base.py
index 11313fc933..577229c119 100644
--- a/tests/storage/test_base.py
+++ b/tests/storage/test_base.py
@@ -86,7 +86,7 @@ class SQLBaseStoreTestCase(unittest.TestCase):
 
         conn_pool.runWithConnection = runWithConnection
 
-        config = default_config(name="test", parse=True)
+        config = default_config(server_name="test", parse=True)
         hs = TestHomeServer("test", config=config)
 
         if USE_POSTGRES_FOR_TESTS:
diff --git a/tests/storage/test_client_ips.py b/tests/storage/test_client_ips.py
index 1cd97a9dd7..bd68f2aaa1 100644
--- a/tests/storage/test_client_ips.py
+++ b/tests/storage/test_client_ips.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import Any, Dict, List, Optional, Tuple, cast
+from typing import Any, cast
 from unittest.mock import AsyncMock
 
 from parameterized import parameterized
@@ -104,7 +104,7 @@ class ClientIpStoreTestCase(unittest.HomeserverTestCase):
         self.pump(0)
 
         result = cast(
-            List[Tuple[str, str, str, Optional[str], int]],
+            list[tuple[str, str, str, str | None, int]],
             self.get_success(
                 self.store.db_pool.simple_select_list(
                     table="user_ips",
@@ -135,7 +135,7 @@ class ClientIpStoreTestCase(unittest.HomeserverTestCase):
         self.pump(0)
 
         result = cast(
-            List[Tuple[str, str, str, Optional[str], int]],
+            list[tuple[str, str, str, str | None, int]],
             self.get_success(
                 self.store.db_pool.simple_select_list(
                     table="user_ips",
@@ -184,7 +184,7 @@ class ClientIpStoreTestCase(unittest.HomeserverTestCase):
         else:
             # Check that the new IP and user agent has not been stored yet
             db_result = cast(
-                List[Tuple[str, Optional[str], Optional[str], str, Optional[int]]],
+                list[tuple[str, str | None, str | None, str, int | None]],
                 self.get_success(
                     self.store.db_pool.simple_select_list(
                         table="devices",
@@ -266,7 +266,7 @@ class ClientIpStoreTestCase(unittest.HomeserverTestCase):
 
         # Check that the new IP and user agent has not been stored yet
         db_result = cast(
-            List[Tuple[str, Optional[str], Optional[str], str, Optional[int]]],
+            list[tuple[str, str | None, str | None, str, int | None]],
             self.get_success(
                 self.store.db_pool.simple_select_list(
                     table="devices",
@@ -381,7 +381,7 @@ class ClientIpStoreTestCase(unittest.HomeserverTestCase):
 
         # Check that the new IP and user agent has not been stored yet
         db_result = cast(
-            List[Tuple[str, str, str, int]],
+            list[tuple[str, str, str, int]],
             self.get_success(
                 self.store.db_pool.simple_select_list(
                     table="user_ips",
@@ -589,7 +589,7 @@ class ClientIpStoreTestCase(unittest.HomeserverTestCase):
 
         # We should see that in the DB
         result = cast(
-            List[Tuple[str, str, str, Optional[str], int]],
+            list[tuple[str, str, str, str | None, int]],
             self.get_success(
                 self.store.db_pool.simple_select_list(
                     table="user_ips",
@@ -616,7 +616,7 @@ class ClientIpStoreTestCase(unittest.HomeserverTestCase):
 
         # We should get no results.
         result = cast(
-            List[Tuple[str, str, str, Optional[str], int]],
+            list[tuple[str, str, str, str | None, int]],
             self.get_success(
                 self.store.db_pool.simple_select_list(
                     table="user_ips",
@@ -695,7 +695,7 @@ class ClientIpStoreTestCase(unittest.HomeserverTestCase):
 
         # We should see that in the DB
         result = cast(
-            List[Tuple[str, str, str, Optional[str], int]],
+            list[tuple[str, str, str, str | None, int]],
             self.get_success(
                 self.store.db_pool.simple_select_list(
                     table="user_ips",
@@ -745,9 +745,9 @@ class ClientIpAuthTestCase(unittest.HomeserverTestCase):
 
     def _runtest(
         self,
-        headers: Dict[bytes, bytes],
+        headers: dict[bytes, bytes],
         expected_ip: str,
-        make_request_args: Dict[str, Any],
+        make_request_args: dict[str, Any],
     ) -> None:
         device_id = "bleb"
 
diff --git a/tests/storage/test_database.py b/tests/storage/test_database.py
index fd6963bb82..ffcff3363f 100644
--- a/tests/storage/test_database.py
+++ b/tests/storage/test_database.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import Callable, Tuple
+from typing import Callable
 from unittest.mock import Mock, call
 
 from twisted.internet import defer
@@ -149,7 +149,7 @@ class CallbacksTestCase(unittest.HomeserverTestCase):
 
     def _run_interaction(
         self, func: Callable[[LoggingTransaction], object]
-    ) -> Tuple[Mock, Mock]:
+    ) -> tuple[Mock, Mock]:
         """Run the given function in a database transaction, with callbacks registered.
 
         Args:
diff --git a/tests/storage/test_devices.py b/tests/storage/test_devices.py
index bd6fcd8eeb..1d1979e19f 100644
--- a/tests/storage/test_devices.py
+++ b/tests/storage/test_devices.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import Collection, List, Tuple
+from typing import Collection
 
 from twisted.internet.testing import MemoryReactor
 
@@ -44,7 +44,7 @@ class DeviceStoreTestCase(HomeserverTestCase):
         config["federation_sender_instances"] = ["master"]
         return config
 
-    def add_device_change(self, user_id: str, device_ids: List[str], host: str) -> None:
+    def add_device_change(self, user_id: str, device_ids: list[str], host: str) -> None:
         """Add a device list change for the given device to
         `device_lists_outbound_pokes` table.
         """
@@ -306,7 +306,7 @@ class DeviceStoreTestCase(HomeserverTestCase):
     def _check_devices_in_updates(
         self,
         expected_device_ids: Collection[str],
-        device_updates: List[Tuple[str, JsonDict]],
+        device_updates: list[tuple[str, JsonDict]],
     ) -> None:
         """Check that an specific device ids exist in a list of device update EDUs"""
         self.assertEqual(len(device_updates), len(expected_device_ids))
diff --git a/tests/storage/test_event_chain.py b/tests/storage/test_event_chain.py
index fe9bb7bcca..175a5ffc78 100644
--- a/tests/storage/test_event_chain.py
+++ b/tests/storage/test_event_chain.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import Dict, List, Set, Tuple, cast
+from typing import cast
 
 from parameterized import parameterized
 
@@ -420,7 +420,7 @@ class EventChainStoreTestCase(HomeserverTestCase):
 
     def persist(
         self,
-        events: List[EventBase],
+        events: list[EventBase],
     ) -> None:
         """Persist the given events and check that the links generated match
         those given.
@@ -464,11 +464,11 @@ class EventChainStoreTestCase(HomeserverTestCase):
         )
 
     def fetch_chains(
-        self, events: List[EventBase]
-    ) -> Tuple[Dict[str, Tuple[int, int]], _LinkMap]:
+        self, events: list[EventBase]
+    ) -> tuple[dict[str, tuple[int, int]], _LinkMap]:
         # Fetch the map from event ID -> (chain ID, sequence number)
         rows = cast(
-            List[Tuple[str, int, int]],
+            list[tuple[str, int, int]],
             self.get_success(
                 self.store.db_pool.simple_select_many_batch(
                     table="event_auth_chains",
@@ -487,7 +487,7 @@ class EventChainStoreTestCase(HomeserverTestCase):
 
         # Fetch all the links and pass them to the _LinkMap.
         auth_chain_rows = cast(
-            List[Tuple[int, int, int, int]],
+            list[tuple[int, int, int, int]],
             self.get_success(
                 self.store.db_pool.simple_select_many_batch(
                     table="event_auth_chain_links",
@@ -575,7 +575,7 @@ class EventChainBackgroundUpdateTestCase(HomeserverTestCase):
         self.token = self.login("foo", "pass")
         self.requester = create_requester(self.user_id)
 
-    def _generate_room(self) -> Tuple[str, List[Set[str]]]:
+    def _generate_room(self) -> tuple[str, list[set[str]]]:
         """Insert a room without a chain cover index."""
         room_id = self.helper.create_room_as(self.user_id, tok=self.token)
 
diff --git a/tests/storage/test_event_federation.py b/tests/storage/test_event_federation.py
index ee9cf3687f..508f82de4f 100644
--- a/tests/storage/test_event_federation.py
+++ b/tests/storage/test_event_federation.py
@@ -21,16 +21,10 @@
 import datetime
 from typing import (
     Collection,
-    Dict,
-    FrozenSet,
     Iterable,
-    List,
     Mapping,
     NamedTuple,
-    Set,
-    Tuple,
     TypeVar,
-    Union,
     cast,
 )
 
@@ -74,7 +68,7 @@ import tests.utils
 #     |   |
 #     K   J
 
-AUTH_GRAPH: Dict[str, List[str]] = {
+AUTH_GRAPH: dict[str, list[str]] = {
     "a": ["e"],
     "b": ["e"],
     "c": ["g", "i"],
@@ -108,7 +102,7 @@ T = TypeVar("T")
 def get_all_topologically_sorted_orders(
     nodes: Iterable[T],
     graph: Mapping[T, Collection[T]],
-) -> List[List[T]]:
+) -> list[list[T]]:
     """Given a set of nodes and a graph, return all possible topological
     orderings.
     """
@@ -117,7 +111,7 @@ def get_all_topologically_sorted_orders(
     # we have a choice over which node to consider next.
 
     degree_map = dict.fromkeys(nodes, 0)
-    reverse_graph: Dict[T, Set[T]] = {}
+    reverse_graph: dict[T, set[T]] = {}
 
     for node, edges in graph.items():
         if node not in degree_map:
@@ -138,10 +132,10 @@ def get_all_topologically_sorted_orders(
 
 
 def _get_all_topologically_sorted_orders_inner(
-    reverse_graph: Dict[T, Set[T]],
-    zero_degree: List[T],
-    degree_map: Dict[T, int],
-) -> List[List[T]]:
+    reverse_graph: dict[T, set[T]],
+    zero_degree: list[T],
+    degree_map: dict[T, int],
+) -> list[list[T]]:
     new_paths = []
 
     # Rather than only choosing *one* item from the list of nodes with zero
@@ -175,7 +169,7 @@ def _get_all_topologically_sorted_orders_inner(
 def get_all_topologically_consistent_subsets(
     nodes: Iterable[T],
     graph: Mapping[T, Collection[T]],
-) -> Set[FrozenSet[T]]:
+) -> set[frozenset[T]]:
     """Get all subsets of the graph where if node N is in the subgraph, then all
     nodes that can reach that node (i.e. for all X there exists a path X -> N)
     are in the subgraph.
@@ -195,7 +189,7 @@ def get_all_topologically_consistent_subsets(
 @attr.s(auto_attribs=True, frozen=True, slots=True)
 class _BackfillSetupInfo:
     room_id: str
-    depth_map: Dict[str, int]
+    depth_map: dict[str, int]
 
 
 class EventFederationWorkerStoreTestCase(tests.unittest.HomeserverTestCase):
@@ -573,7 +567,7 @@ class EventFederationWorkerStoreTestCase(tests.unittest.HomeserverTestCase):
         #     |   |
         #     K   J
 
-        auth_graph: Dict[str, List[str]] = {
+        auth_graph: dict[str, list[str]] = {
             "a": ["e"],
             "b": ["e"],
             "c": ["g", "i"],
@@ -756,11 +750,11 @@ class EventFederationWorkerStoreTestCase(tests.unittest.HomeserverTestCase):
             seq_num: int
 
         class TestLink(NamedTuple):
-            origin_chain_and_seq: Tuple[int, int]
-            target_chain_and_seq: Tuple[int, int]
+            origin_chain_and_seq: tuple[int, int]
+            target_chain_and_seq: tuple[int, int]
 
         # Map to chain IDs / seq nums
-        nodes: List[TestNode] = [
+        nodes: list[TestNode] = [
             TestNode("A1", 1, 1),
             TestNode("A2", 1, 2),
             TestNode("A3", 1, 3),
@@ -779,7 +773,7 @@ class EventFederationWorkerStoreTestCase(tests.unittest.HomeserverTestCase):
             TestNode("G1", 7, 1),
             TestNode("G2", 7, 2),
         ]
-        links: List[TestLink] = [
+        links: list[TestLink] = [
             TestLink((2, 1), (1, 2)),  # B1 -> A2
             TestLink((3, 1), (2, 2)),  # C1 -> B2
             TestLink((4, 1), (3, 1)),  # D1 -> C1
@@ -818,9 +812,9 @@ class EventFederationWorkerStoreTestCase(tests.unittest.HomeserverTestCase):
         # Define the test cases
         class TestCase(NamedTuple):
             name: str
-            conflicted: Set[str]
-            additional_backwards_reachable: Set[str]
-            want_conflicted_subgraph: Set[str]
+            conflicted: set[str]
+            additional_backwards_reachable: set[str]
+            want_conflicted_subgraph: set[str]
 
         # Reminder:
         # A1 <- A2 <- A3
@@ -936,7 +930,7 @@ class EventFederationWorkerStoreTestCase(tests.unittest.HomeserverTestCase):
 
         room_id = "some_room_id"
 
-        def prev_event_format(prev_event_id: str) -> Union[Tuple[str, dict], str]:
+        def prev_event_format(prev_event_id: str) -> tuple[str, dict] | str:
             """Account for differences in prev_events format across room versions"""
             if room_version.event_format == EventFormatVersions.ROOM_V1_V2:
                 return prev_event_id, {}
@@ -1034,7 +1028,7 @@ class EventFederationWorkerStoreTestCase(tests.unittest.HomeserverTestCase):
         #    |
         #    5 (newest)
 
-        event_graph: Dict[str, List[str]] = {
+        event_graph: dict[str, list[str]] = {
             "1": [],
             "2": ["1"],
             "3": ["2", "A"],
@@ -1050,7 +1044,7 @@ class EventFederationWorkerStoreTestCase(tests.unittest.HomeserverTestCase):
             "b6": ["3"],
         }
 
-        depth_map: Dict[str, int] = {
+        depth_map: dict[str, int] = {
             "1": 1,
             "2": 2,
             "b1": 3,
@@ -1070,7 +1064,7 @@ class EventFederationWorkerStoreTestCase(tests.unittest.HomeserverTestCase):
         # The rest are events in the room but not backfilled tet.
         our_server_events = {"5", "4", "B", "3", "A"}
 
-        complete_event_dict_map: Dict[str, JsonDict] = {}
+        complete_event_dict_map: dict[str, JsonDict] = {}
         stream_ordering = 0
         for event_id, prev_event_ids in event_graph.items():
             depth = depth_map[event_id]
@@ -1425,14 +1419,14 @@ class EventFederationWorkerStoreTestCase(tests.unittest.HomeserverTestCase):
 class FakeEvent:
     event_id: str
     room_id: str
-    auth_events: List[str]
+    auth_events: list[str]
 
     type = "foo"
     state_key = "foo"
 
     internal_metadata = EventInternalMetadata({})
 
-    def auth_event_ids(self) -> List[str]:
+    def auth_event_ids(self) -> list[str]:
         return self.auth_events
 
     def is_state(self) -> bool:
diff --git a/tests/storage/test_event_push_actions.py b/tests/storage/test_event_push_actions.py
index 30ba1ad94a..d5ed947094 100644
--- a/tests/storage/test_event_push_actions.py
+++ b/tests/storage/test_event_push_actions.py
@@ -19,7 +19,6 @@
 #
 #
 
-from typing import Optional, Tuple
 
 from twisted.internet.testing import MemoryReactor
 
@@ -47,7 +46,7 @@ class EventPushActionsStoreTestCase(HomeserverTestCase):
         assert persist_events_store is not None
         self.persist_events_store = persist_events_store
 
-    def _create_users_and_room(self) -> Tuple[str, str, str, str, str]:
+    def _create_users_and_room(self) -> tuple[str, str, str, str, str]:
         """
         Creates two users and a shared room.
 
@@ -345,9 +344,7 @@ class EventPushActionsStoreTestCase(HomeserverTestCase):
                 aggregate_counts[room_id], notif_count + thread_notif_count
             )
 
-        def _create_event(
-            highlight: bool = False, thread_id: Optional[str] = None
-        ) -> str:
+        def _create_event(highlight: bool = False, thread_id: str | None = None) -> str:
             content: JsonDict = {
                 "msgtype": "m.text",
                 "body": user_id if highlight else "msg",
@@ -527,9 +524,7 @@ class EventPushActionsStoreTestCase(HomeserverTestCase):
                 aggregate_counts[room_id], notif_count + thread_notif_count
             )
 
-        def _create_event(
-            highlight: bool = False, thread_id: Optional[str] = None
-        ) -> str:
+        def _create_event(highlight: bool = False, thread_id: str | None = None) -> str:
             content: JsonDict = {
                 "msgtype": "m.text",
                 "body": user_id if highlight else "msg",
@@ -553,7 +548,7 @@ class EventPushActionsStoreTestCase(HomeserverTestCase):
         def _rotate() -> None:
             self.get_success(self.store._rotate_notifs())
 
-        def _mark_read(event_id: str, thread_id: Optional[str] = None) -> None:
+        def _mark_read(event_id: str, thread_id: str | None = None) -> None:
             self.get_success(
                 self.store.insert_receipt(
                     room_id,
diff --git a/tests/storage/test_events.py b/tests/storage/test_events.py
index 25a380e325..7d1c96f97f 100644
--- a/tests/storage/test_events.py
+++ b/tests/storage/test_events.py
@@ -20,7 +20,6 @@
 #
 
 import logging
-from typing import Dict, List, Optional
 
 from twisted.internet.testing import MemoryReactor
 
@@ -54,7 +53,7 @@ class EventsTestCase(HomeserverTestCase):
     def test_get_senders_for_event_ids(self) -> None:
         """Tests the `get_senders_for_event_ids` storage function."""
 
-        users_and_tokens: Dict[str, str] = {}
+        users_and_tokens: dict[str, str] = {}
         for localpart_suffix in range(10):
             localpart = f"user_{localpart_suffix}"
             user_id = self.register_user(localpart, "rabbit")
@@ -70,7 +69,7 @@ class EventsTestCase(HomeserverTestCase):
         room_id = self.helper.create_room_as(
             room_creator_user_id, tok=room_creator_token
         )
-        event_ids_to_senders: Dict[str, str] = {}
+        event_ids_to_senders: dict[str, str] = {}
         for user_id, token in users_and_tokens.items():
             if user_id == room_creator_user_id:
                 continue
@@ -168,7 +167,7 @@ class ExtremPruneTestCase(HomeserverTestCase):
         self.assert_extremities([self.remote_event_1.event_id])
 
     def persist_event(
-        self, event: EventBase, state: Optional[StateMap[str]] = None
+        self, event: EventBase, state: StateMap[str] | None = None
     ) -> None:
         """Persist the event, with optional state"""
         context = self.get_success(
@@ -180,7 +179,7 @@ class ExtremPruneTestCase(HomeserverTestCase):
         )
         self.get_success(self._persistence.persist_event(event, context))
 
-    def assert_extremities(self, expected_extremities: List[str]) -> None:
+    def assert_extremities(self, expected_extremities: list[str]) -> None:
         """Assert the current extremities for the room"""
         extremities = self.get_success(
             self.store.get_prev_events_for_room(self.room_id)
diff --git a/tests/storage/test_events_bg_updates.py b/tests/storage/test_events_bg_updates.py
index a1375aa4ac..d1a794c5a1 100644
--- a/tests/storage/test_events_bg_updates.py
+++ b/tests/storage/test_events_bg_updates.py
@@ -13,7 +13,6 @@
 #
 #
 
-from typing import Dict
 
 from twisted.internet.testing import MemoryReactor
 
@@ -48,7 +47,7 @@ class TestFixupMaxDepthCapBgUpdate(HomeserverTestCase):
             )
         )
 
-    def create_room(self, room_version: RoomVersion) -> Dict[str, int]:
+    def create_room(self, room_version: RoomVersion) -> dict[str, int]:
         """Create a room with a known room version and insert events.
 
         Returns the set of event IDs that exceed MAX_DEPTH and
@@ -67,7 +66,7 @@ class TestFixupMaxDepthCapBgUpdate(HomeserverTestCase):
         )
 
         # Insert events with some depths exceeding MAX_DEPTH
-        event_id_to_depth: Dict[str, int] = {}
+        event_id_to_depth: dict[str, int] = {}
         for depth in range(MAX_DEPTH - 5, MAX_DEPTH + 5):
             event_id = f"$event{depth}:example.com"
             event_id_to_depth[event_id] = depth
diff --git a/tests/storage/test_id_generators.py b/tests/storage/test_id_generators.py
index 4c1311a00e..051c5de44d 100644
--- a/tests/storage/test_id_generators.py
+++ b/tests/storage/test_id_generators.py
@@ -18,7 +18,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Dict, List, Optional
 
 from twisted.internet.testing import MemoryReactor
 
@@ -43,12 +42,12 @@ from tests.utils import USE_POSTGRES_FOR_TESTS
 
 class MultiWriterIdGeneratorBase(HomeserverTestCase):
     positive: bool = True
-    tables: List[str] = ["foobar"]
+    tables: list[str] = ["foobar"]
 
     def prepare(self, reactor: MemoryReactor, clock: Clock, hs: HomeServer) -> None:
         self.store = hs.get_datastores().main
         self.db_pool: DatabasePool = self.store.db_pool
-        self.instances: Dict[str, MultiWriterIdGenerator] = {}
+        self.instances: dict[str, MultiWriterIdGenerator] = {}
 
         self.get_success(self.db_pool.runInteraction("_setup_db", self._setup_db))
 
@@ -76,7 +75,7 @@ class MultiWriterIdGeneratorBase(HomeserverTestCase):
     def _create_id_generator(
         self,
         instance_name: str = "master",
-        writers: Optional[List[str]] = None,
+        writers: list[str] | None = None,
     ) -> MultiWriterIdGenerator:
         def _create(conn: LoggingDatabaseConnection) -> MultiWriterIdGenerator:
             return MultiWriterIdGenerator(
@@ -113,7 +112,7 @@ class MultiWriterIdGeneratorBase(HomeserverTestCase):
             self._replicate(instance_name)
 
     def _insert_row(
-        self, instance_name: str, stream_id: int, table: Optional[str] = None
+        self, instance_name: str, stream_id: int, table: str | None = None
     ) -> None:
         """Insert one row as the given instance with given stream_id."""
 
@@ -144,7 +143,7 @@ class MultiWriterIdGeneratorBase(HomeserverTestCase):
         self,
         instance_name: str,
         number: int,
-        table: Optional[str] = None,
+        table: str | None = None,
         update_stream_table: bool = True,
     ) -> None:
         """Insert N rows as the given instance, inserting with stream IDs pulled
diff --git a/tests/storage/test_monthly_active_users.py b/tests/storage/test_monthly_active_users.py
index e684c6c161..4f97d89f78 100644
--- a/tests/storage/test_monthly_active_users.py
+++ b/tests/storage/test_monthly_active_users.py
@@ -17,7 +17,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Any, Dict, List
+from typing import Any
 from unittest.mock import AsyncMock
 
 from twisted.internet.testing import MemoryReactor
@@ -32,7 +32,7 @@ from tests.unittest import default_config, override_config
 FORTY_DAYS = 40 * 24 * 60 * 60
 
 
-def gen_3pids(count: int) -> List[Dict[str, Any]]:
+def gen_3pids(count: int) -> list[dict[str, Any]]:
     """Generate `count` threepids as a list."""
     return [
         {"medium": "email", "address": "user%i@matrix.org" % i} for i in range(count)
@@ -40,7 +40,7 @@ def gen_3pids(count: int) -> List[Dict[str, Any]]:
 
 
 class MonthlyActiveUsersTestCase(unittest.HomeserverTestCase):
-    def default_config(self) -> Dict[str, Any]:
+    def default_config(self) -> dict[str, Any]:
         config = default_config("test")
 
         config.update({"limit_usage_by_mau": True, "max_mau_value": 50})
@@ -101,7 +101,7 @@ class MonthlyActiveUsersTestCase(unittest.HomeserverTestCase):
 
         # Test each of the registered users is marked as active
         timestamp = self.get_success(self.store.user_last_seen_monthly_active(user1))
-        # Mypy notes that one shouldn't compare Optional[int] to 0 with assertGreater.
+        # Mypy notes that one shouldn't compare int | None to 0 with assertGreater.
         # Check that timestamp really is an int.
         assert timestamp is not None
         self.assertGreater(timestamp, 0)
@@ -110,13 +110,13 @@ class MonthlyActiveUsersTestCase(unittest.HomeserverTestCase):
         self.assertGreater(timestamp, 0)
 
         # Test that users with reserved 3pids are not removed from the MAU table
-        # XXX some of this is redundant. poking things into the config shouldn't
-        # work, and in any case it's not obvious what we expect to happen when
-        # we advance the reactor.
-        self.hs.config.server.max_mau_value = 0
+        #
+        # The `start_phone_stats_home()` looping call will cause us to run
+        # `reap_monthly_active_users` after the time has advanced
         self.reactor.advance(FORTY_DAYS)
-        self.hs.config.server.max_mau_value = 5
 
+        # I guess we call this one more time for good measure? Perhaps because
+        # previously, the phone home stats weren't running in tests?
         self.get_success(self.store.reap_monthly_active_users())
 
         active_count = self.get_success(self.store.get_monthly_active_count())
diff --git a/tests/storage/test_receipts.py b/tests/storage/test_receipts.py
index 10ded391f4..27875dcebb 100644
--- a/tests/storage/test_receipts.py
+++ b/tests/storage/test_receipts.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import Collection, Optional
+from typing import Collection
 
 from twisted.internet.testing import MemoryReactor
 
@@ -101,8 +101,8 @@ class ReceiptTestCase(HomeserverTestCase):
         )
 
     def get_last_unthreaded_receipt(
-        self, receipt_types: Collection[str], room_id: Optional[str] = None
-    ) -> Optional[str]:
+        self, receipt_types: Collection[str], room_id: str | None = None
+    ) -> str | None:
         """
         Fetch the event ID for the latest unthreaded receipt in the test room for the test user.
 
diff --git a/tests/storage/test_redaction.py b/tests/storage/test_redaction.py
index 7565376a59..92eb99f1d5 100644
--- a/tests/storage/test_redaction.py
+++ b/tests/storage/test_redaction.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import List, Optional, cast
+from typing import cast
 
 from canonicaljson import json
 
@@ -67,7 +67,7 @@ class RedactionTestCase(unittest.HomeserverTestCase):
         room: RoomID,
         user: UserID,
         membership: str,
-        extra_content: Optional[JsonDict] = None,
+        extra_content: JsonDict | None = None,
     ) -> EventBase:
         content = {"membership": membership}
         content.update(extra_content or {})
@@ -247,9 +247,9 @@ class RedactionTestCase(unittest.HomeserverTestCase):
 
             async def build(
                 self,
-                prev_event_ids: List[str],
-                auth_event_ids: Optional[List[str]],
-                depth: Optional[int] = None,
+                prev_event_ids: list[str],
+                auth_event_ids: list[str] | None,
+                depth: int | None = None,
             ) -> EventBase:
                 built_event = await self._base_builder.build(
                     prev_event_ids=prev_event_ids, auth_event_ids=auth_event_ids
diff --git a/tests/storage/test_rollback_worker.py b/tests/storage/test_rollback_worker.py
index f61eb2e319..125c4499b0 100644
--- a/tests/storage/test_rollback_worker.py
+++ b/tests/storage/test_rollback_worker.py
@@ -18,7 +18,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import List
 from unittest import mock
 
 from twisted.internet.testing import MemoryReactor
@@ -34,7 +33,7 @@ from synapse.util.clock import Clock
 from tests.unittest import HomeserverTestCase
 
 
-def fake_listdir(filepath: str) -> List[str]:
+def fake_listdir(filepath: str) -> list[str]:
     """
     A fake implementation of os.listdir which we can use to mock out the filesystem.
 
diff --git a/tests/storage/test_room_search.py b/tests/storage/test_room_search.py
index e530e59fa6..2c0ef19e9e 100644
--- a/tests/storage/test_room_search.py
+++ b/tests/storage/test_room_search.py
@@ -19,7 +19,6 @@
 #
 #
 
-from typing import List, Tuple
 from unittest.case import SkipTest
 
 from twisted.internet.testing import MemoryReactor
@@ -317,7 +316,7 @@ class MessageSearchTest(HomeserverTestCase):
             )
 
     def _check_test_cases(
-        self, store: DataStore, cases: List[Tuple[str, bool]]
+        self, store: DataStore, cases: list[tuple[str, bool]]
     ) -> None:
         # Run all the test cases versus search_msgs
         for query, expect_to_contain in cases:
diff --git a/tests/storage/test_roommember.py b/tests/storage/test_roommember.py
index b8933d957b..f8d64e8ce6 100644
--- a/tests/storage/test_roommember.py
+++ b/tests/storage/test_roommember.py
@@ -20,7 +20,7 @@
 #
 #
 import logging
-from typing import List, Optional, Tuple, cast
+from typing import cast
 
 from twisted.internet.testing import MemoryReactor
 
@@ -133,7 +133,7 @@ class RoomMemberStoreTestCase(unittest.HomeserverTestCase):
         room = self.helper.create_room_as(self.u_alice, tok=self.t_alice)
 
         res = cast(
-            List[Tuple[Optional[str], str]],
+            list[tuple[str | None, str]],
             self.get_success(
                 self.store.db_pool.simple_select_list(
                     "room_memberships",
@@ -165,7 +165,7 @@ class RoomMemberStoreTestCase(unittest.HomeserverTestCase):
         )
 
         res2 = cast(
-            List[Tuple[Optional[str], str]],
+            list[tuple[str | None, str]],
             self.get_success(
                 self.store.db_pool.simple_select_list(
                     "room_memberships",
@@ -408,9 +408,9 @@ class RoomSummaryTestCase(unittest.HomeserverTestCase):
     def _assert_member_summary(
         self,
         actual_member_summary: MemberSummary,
-        expected_member_list: List[str],
+        expected_member_list: list[str],
         *,
-        expected_member_count: Optional[int] = None,
+        expected_member_count: int | None = None,
     ) -> None:
         """
         Assert that the `MemberSummary` object has the expected members.
diff --git a/tests/storage/test_sliding_sync_tables.py b/tests/storage/test_sliding_sync_tables.py
index f0df166bab..db31348a8c 100644
--- a/tests/storage/test_sliding_sync_tables.py
+++ b/tests/storage/test_sliding_sync_tables.py
@@ -18,7 +18,7 @@
 #
 #
 import logging
-from typing import Dict, List, Optional, Tuple, cast
+from typing import cast
 
 import attr
 from parameterized import parameterized
@@ -55,12 +55,12 @@ class _SlidingSyncJoinedRoomResult:
     # `event.internal_metadata.stream_ordering` is marked optional because it only
     # exists for persisted events but in the context of these tests, we're only working
     # with persisted events and we're making comparisons so we will find any mismatch.
-    event_stream_ordering: Optional[int]
-    bump_stamp: Optional[int]
-    room_type: Optional[str]
-    room_name: Optional[str]
+    event_stream_ordering: int | None
+    bump_stamp: int | None
+    room_type: str | None
+    room_name: str | None
     is_encrypted: bool
-    tombstone_successor_room_id: Optional[str]
+    tombstone_successor_room_id: str | None
 
 
 @attr.s(slots=True, frozen=True, auto_attribs=True)
@@ -75,12 +75,12 @@ class _SlidingSyncMembershipSnapshotResult:
     # `event.internal_metadata.stream_ordering` is marked optional because it only
     # exists for persisted events but in the context of these tests, we're only working
     # with persisted events and we're making comparisons so we will find any mismatch.
-    event_stream_ordering: Optional[int]
+    event_stream_ordering: int | None
     has_known_state: bool
-    room_type: Optional[str]
-    room_name: Optional[str]
+    room_type: str | None
+    room_name: str | None
     is_encrypted: bool
-    tombstone_successor_room_id: Optional[str]
+    tombstone_successor_room_id: str | None
     # Make this default to "not forgotten" because it doesn't apply to many tests and we
     # don't want to force all of the tests to deal with it.
     forgotten: bool = False
@@ -112,7 +112,7 @@ class SlidingSyncTablesTestCaseBase(HomeserverTestCase):
 
         self.state_handler = self.hs.get_state_handler()
 
-    def _get_sliding_sync_joined_rooms(self) -> Dict[str, _SlidingSyncJoinedRoomResult]:
+    def _get_sliding_sync_joined_rooms(self) -> dict[str, _SlidingSyncJoinedRoomResult]:
         """
         Return the rows from the `sliding_sync_joined_rooms` table.
 
@@ -120,7 +120,7 @@ class SlidingSyncTablesTestCaseBase(HomeserverTestCase):
             Mapping from room_id to _SlidingSyncJoinedRoomResult.
         """
         rows = cast(
-            List[Tuple[str, int, int, str, str, bool, str]],
+            list[tuple[str, int, int, str, str, bool, str]],
             self.get_success(
                 self.store.db_pool.simple_select_list(
                     "sliding_sync_joined_rooms",
@@ -153,7 +153,7 @@ class SlidingSyncTablesTestCaseBase(HomeserverTestCase):
 
     def _get_sliding_sync_membership_snapshots(
         self,
-    ) -> Dict[Tuple[str, str], _SlidingSyncMembershipSnapshotResult]:
+    ) -> dict[tuple[str, str], _SlidingSyncMembershipSnapshotResult]:
         """
         Return the rows from the `sliding_sync_membership_snapshots` table.
 
@@ -161,7 +161,7 @@ class SlidingSyncTablesTestCaseBase(HomeserverTestCase):
             Mapping from the (room_id, user_id) to _SlidingSyncMembershipSnapshotResult.
         """
         rows = cast(
-            List[Tuple[str, str, str, str, str, int, int, bool, str, str, bool, str]],
+            list[tuple[str, str, str, str, str, int, int, bool, str, str, bool, str]],
             self.get_success(
                 self.store.db_pool.simple_select_list(
                     "sliding_sync_membership_snapshots",
@@ -207,8 +207,8 @@ class SlidingSyncTablesTestCaseBase(HomeserverTestCase):
     def _create_remote_invite_room_for_user(
         self,
         invitee_user_id: str,
-        unsigned_invite_room_state: Optional[List[StrippedStateEvent]],
-    ) -> Tuple[str, EventBase]:
+        unsigned_invite_room_state: list[StrippedStateEvent] | None,
+    ) -> tuple[str, EventBase]:
         """
         Create a fake invite for a remote room and persist it.
 
@@ -2246,7 +2246,7 @@ class SlidingSyncTablesTestCase(SlidingSyncTablesTestCaseBase):
         ]
     )
     def test_non_join_remote_invite_no_stripped_state(
-        self, _description: str, stripped_state: Optional[List[StrippedStateEvent]]
+        self, _description: str, stripped_state: list[StrippedStateEvent] | None
     ) -> None:
         """
         Test remote invite with no stripped state provided shows up in
diff --git a/tests/storage/test_state.py b/tests/storage/test_state.py
index bf6da71549..8e821c6d18 100644
--- a/tests/storage/test_state.py
+++ b/tests/storage/test_state.py
@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import List, Tuple, cast
+from typing import cast
 
 from immutabledict import immutabledict
 
@@ -593,7 +593,7 @@ class StateStoreTestCase(HomeserverTestCase):
 
         # check that only state events are in state_groups, and all state events are in state_groups
         res = cast(
-            List[Tuple[str]],
+            list[tuple[str]],
             self.get_success(
                 self.store.db_pool.simple_select_list(
                     table="state_groups",
@@ -618,7 +618,7 @@ class StateStoreTestCase(HomeserverTestCase):
         for event, context in processed_events_and_context:
             if event.is_state():
                 state = cast(
-                    List[Tuple[str, str]],
+                    list[tuple[str, str]],
                     self.get_success(
                         self.store.db_pool.simple_select_list(
                             table="state_groups_state",
@@ -631,7 +631,7 @@ class StateStoreTestCase(HomeserverTestCase):
                 self.assertEqual(event.state_key, state[0][1])
 
                 groups = cast(
-                    List[Tuple[str]],
+                    list[tuple[str]],
                     self.get_success(
                         self.store.db_pool.simple_select_list(
                             table="state_group_edges",
diff --git a/tests/storage/test_stream.py b/tests/storage/test_stream.py
index 0777c254c0..d51fa1f8ba 100644
--- a/tests/storage/test_stream.py
+++ b/tests/storage/test_stream.py
@@ -20,7 +20,6 @@
 #
 
 import logging
-from typing import List, Tuple
 from unittest.mock import AsyncMock, patch
 
 from immutabledict import immutabledict
@@ -150,7 +149,7 @@ class PaginationTestCase(HomeserverTestCase):
         )
         self.event_id_none = res["event_id"]
 
-    def _filter_messages(self, filter: JsonDict) -> List[str]:
+    def _filter_messages(self, filter: JsonDict) -> list[str]:
         """Make a request to /messages with a filter, returns the chunk of events."""
 
         events, next_key, _ = self.get_success(
@@ -324,7 +323,7 @@ class GetLastEventInRoomBeforeStreamOrderingTestCase(HomeserverTestCase):
 
     def _send_event_on_instance(
         self, instance_name: str, room_id: str, access_token: str
-    ) -> Tuple[JsonDict, PersistedEventPosition]:
+    ) -> tuple[JsonDict, PersistedEventPosition]:
         """
         Send an event in a room and mimic that it was persisted by a specific
         instance/worker.
diff --git a/tests/storage/test_thread_subscriptions.py b/tests/storage/test_thread_subscriptions.py
index 3f78308e45..ec6f8c5bfb 100644
--- a/tests/storage/test_thread_subscriptions.py
+++ b/tests/storage/test_thread_subscriptions.py
@@ -12,7 +12,6 @@
 # <https://www.gnu.org/licenses/agpl-3.0.html>.
 #
 
-from typing import Optional, Union
 
 from twisted.internet.testing import MemoryReactor
 
@@ -102,10 +101,10 @@ class ThreadSubscriptionsTestCase(unittest.HomeserverTestCase):
         self,
         thread_root_id: str,
         *,
-        automatic_event_orderings: Optional[EventOrderings],
-        room_id: Optional[str] = None,
-        user_id: Optional[str] = None,
-    ) -> Optional[Union[int, AutomaticSubscriptionConflicted]]:
+        automatic_event_orderings: EventOrderings | None,
+        room_id: str | None = None,
+        user_id: str | None = None,
+    ) -> int | AutomaticSubscriptionConflicted | None:
         if user_id is None:
             user_id = self.user_id
 
@@ -124,9 +123,9 @@ class ThreadSubscriptionsTestCase(unittest.HomeserverTestCase):
     def _unsubscribe(
         self,
         thread_root_id: str,
-        room_id: Optional[str] = None,
-        user_id: Optional[str] = None,
-    ) -> Optional[int]:
+        room_id: str | None = None,
+        user_id: str | None = None,
+    ) -> int | None:
         if user_id is None:
             user_id = self.user_id
 
diff --git a/tests/storage/test_user_directory.py b/tests/storage/test_user_directory.py
index 26e045135e..7b4acd985c 100644
--- a/tests/storage/test_user_directory.py
+++ b/tests/storage/test_user_directory.py
@@ -19,7 +19,7 @@
 #
 #
 import re
-from typing import Any, Dict, List, Optional, Set, Tuple, cast
+from typing import Any, cast
 from unittest import mock
 from unittest.mock import Mock, patch
 
@@ -56,21 +56,21 @@ class GetUserDirectoryTables:
     def __init__(self, store: DataStore):
         self.store = store
 
-    async def get_users_in_public_rooms(self) -> Set[Tuple[str, str]]:
+    async def get_users_in_public_rooms(self) -> set[tuple[str, str]]:
         """Fetch the entire `users_in_public_rooms` table.
 
         Returns a list of tuples (user_id, room_id) where room_id is public and
         contains the user with the given id.
         """
         r = cast(
-            List[Tuple[str, str]],
+            list[tuple[str, str]],
             await self.store.db_pool.simple_select_list(
                 "users_in_public_rooms", None, ("user_id", "room_id")
             ),
         )
         return set(r)
 
-    async def get_users_who_share_private_rooms(self) -> Set[Tuple[str, str, str]]:
+    async def get_users_who_share_private_rooms(self) -> set[tuple[str, str, str]]:
         """Fetch the entire `users_who_share_private_rooms` table.
 
         Returns a set of tuples (user_id, other_user_id, room_id) corresponding
@@ -78,7 +78,7 @@ class GetUserDirectoryTables:
         """
 
         rows = cast(
-            List[Tuple[str, str, str]],
+            list[tuple[str, str, str]],
             await self.store.db_pool.simple_select_list(
                 "users_who_share_private_rooms",
                 None,
@@ -87,13 +87,13 @@ class GetUserDirectoryTables:
         )
         return set(rows)
 
-    async def get_users_in_user_directory(self) -> Set[str]:
+    async def get_users_in_user_directory(self) -> set[str]:
         """Fetch the set of users in the `user_directory` table.
 
         This is useful when checking we've correctly excluded users from the directory.
         """
         result = cast(
-            List[Tuple[str]],
+            list[tuple[str]],
             await self.store.db_pool.simple_select_list(
                 "user_directory",
                 None,
@@ -102,7 +102,7 @@ class GetUserDirectoryTables:
         )
         return {row[0] for row in result}
 
-    async def get_profiles_in_user_directory(self) -> Dict[str, ProfileInfo]:
+    async def get_profiles_in_user_directory(self) -> dict[str, ProfileInfo]:
         """Fetch users and their profiles from the `user_directory` table.
 
         This is useful when we want to inspect display names and avatars.
@@ -110,7 +110,7 @@ class GetUserDirectoryTables:
         thing missing is an unused room_id column.
         """
         rows = cast(
-            List[Tuple[str, Optional[str], Optional[str]]],
+            list[tuple[str, str | None, str | None]],
             await self.store.db_pool.simple_select_list(
                 "user_directory",
                 None,
@@ -124,7 +124,7 @@ class GetUserDirectoryTables:
 
     async def get_tables(
         self,
-    ) -> Tuple[Set[str], Set[Tuple[str, str]], Set[Tuple[str, str, str]]]:
+    ) -> tuple[set[str], set[tuple[str, str]], set[tuple[str, str, str]]]:
         """Multiple tests want to inspect these tables, so expose them together."""
         return (
             await self.get_users_in_user_directory(),
@@ -277,7 +277,7 @@ class UserDirectoryInitialPopulationTestcase(HomeserverTestCase):
 
     def _create_rooms_and_inject_memberships(
         self, creator: str, token: str, joiner: str
-    ) -> Tuple[str, str]:
+    ) -> tuple[str, str]:
         """Create a public and private room as a normal user.
         Then get the `joiner` into those rooms.
         """
diff --git a/tests/storage/util/test_partial_state_events_tracker.py b/tests/storage/util/test_partial_state_events_tracker.py
index 1e5663f137..026bc58180 100644
--- a/tests/storage/util/test_partial_state_events_tracker.py
+++ b/tests/storage/util/test_partial_state_events_tracker.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import Collection, Dict
+from typing import Collection
 from unittest import mock
 
 from twisted.internet.defer import CancelledError, ensureDeferred
@@ -35,9 +35,9 @@ from tests.unittest import TestCase
 class PartialStateEventsTrackerTestCase(TestCase):
     def setUp(self) -> None:
         # the results to be returned by the mocked get_partial_state_events
-        self._events_dict: Dict[str, bool] = {}
+        self._events_dict: dict[str, bool] = {}
 
-        async def get_partial_state_events(events: Collection[str]) -> Dict[str, bool]:
+        async def get_partial_state_events(events: Collection[str]) -> dict[str, bool]:
             return {e: self._events_dict[e] for e in events}
 
         self.mock_store = mock.Mock(spec_set=["get_partial_state_events"])
@@ -73,7 +73,7 @@ class PartialStateEventsTrackerTestCase(TestCase):
         # registration of the listener, it should not block.
         self._events_dict = {"event1": True, "event2": False}
 
-        async def get_partial_state_events(events: Collection[str]) -> Dict[str, bool]:
+        async def get_partial_state_events(events: Collection[str]) -> dict[str, bool]:
             res = {e: self._events_dict[e] for e in events}
             # change the result for next time
             self._events_dict = {"event1": False, "event2": False}
@@ -91,13 +91,13 @@ class PartialStateEventsTrackerTestCase(TestCase):
 
         self._events_dict = {"event1": True, "event2": False}
 
-        async def get_partial_state_events1(events: Collection[str]) -> Dict[str, bool]:
+        async def get_partial_state_events1(events: Collection[str]) -> dict[str, bool]:
             self.mock_store.get_partial_state_events.side_effect = (
                 get_partial_state_events2
             )
             return {e: self._events_dict[e] for e in events}
 
-        async def get_partial_state_events2(events: Collection[str]) -> Dict[str, bool]:
+        async def get_partial_state_events2(events: Collection[str]) -> dict[str, bool]:
             self.tracker.notify_un_partial_stated("event1")
             self._events_dict["event1"] = False
             return {e: self._events_dict[e] for e in events}
diff --git a/tests/synapse_rust/__init__.py b/tests/synapse_rust/__init__.py
new file mode 100644
index 0000000000..e056679fd5
--- /dev/null
+++ b/tests/synapse_rust/__init__.py
@@ -0,0 +1,11 @@
+# This file is licensed under the Affero General Public License (AGPL) version 3.
+#
+# Copyright (C) 2025 New Vector, Ltd
+#
+# This program is free software: you can redistribute it and/or modify
+# it under the terms of the GNU Affero General Public License as
+# published by the Free Software Foundation, either version 3 of the
+# License, or (at your option) any later version.
+#
+# See the GNU Affero General Public License for more details:
+# <https://www.gnu.org/licenses/agpl-3.0.html>.
diff --git a/tests/synapse_rust/test_http_client.py b/tests/synapse_rust/test_http_client.py
new file mode 100644
index 0000000000..032eab77e8
--- /dev/null
+++ b/tests/synapse_rust/test_http_client.py
@@ -0,0 +1,225 @@
+# This file is licensed under the Affero General Public License (AGPL) version 3.
+#
+# Copyright (C) 2025 New Vector, Ltd
+#
+# This program is free software: you can redistribute it and/or modify
+# it under the terms of the GNU Affero General Public License as
+# published by the Free Software Foundation, either version 3 of the
+# License, or (at your option) any later version.
+#
+# See the GNU Affero General Public License for more details:
+# <https://www.gnu.org/licenses/agpl-3.0.html>.
+
+import json
+import logging
+import threading
+import time
+from http.server import BaseHTTPRequestHandler, HTTPServer
+from typing import Any, Coroutine, Generator, TypeVar, Union
+
+from twisted.internet.defer import Deferred, ensureDeferred
+from twisted.internet.testing import MemoryReactor
+
+from synapse.logging.context import (
+    LoggingContext,
+    PreserveLoggingContext,
+    _Sentinel,
+    current_context,
+    run_in_background,
+)
+from synapse.server import HomeServer
+from synapse.synapse_rust.http_client import HttpClient
+from synapse.util.clock import Clock
+from synapse.util.json import json_decoder
+
+from tests.unittest import HomeserverTestCase
+
+logger = logging.getLogger(__name__)
+
+T = TypeVar("T")
+
+
+class StubRequestHandler(BaseHTTPRequestHandler):
+    server: "StubServer"
+
+    def do_GET(self) -> None:
+        self.server.calls += 1
+
+        self.send_response(200)
+        self.send_header("Content-Type", "application/json")
+        self.end_headers()
+        self.wfile.write(json.dumps({"ok": True}).encode("utf-8"))
+
+    def log_message(self, format: str, *args: Any) -> None:
+        # Don't log anything; by default, the server logs to stderr
+        pass
+
+
+class StubServer(HTTPServer):
+    """A stub HTTP server that we can send requests to for testing.
+
+    This opens a real HTTP server on a random port, on a separate thread.
+    """
+
+    calls: int = 0
+    """How many times has the endpoint been requested."""
+
+    _thread: threading.Thread
+
+    def __init__(self) -> None:
+        super().__init__(("127.0.0.1", 0), StubRequestHandler)
+
+        self._thread = threading.Thread(
+            target=self.serve_forever,
+            name="StubServer",
+            kwargs={"poll_interval": 0.01},
+            daemon=True,
+        )
+        self._thread.start()
+
+    def shutdown(self) -> None:
+        super().shutdown()
+        self._thread.join()
+
+    @property
+    def endpoint(self) -> str:
+        return f"http://127.0.0.1:{self.server_port}/"
+
+
+class HttpClientTestCase(HomeserverTestCase):
+    def make_homeserver(self, reactor: MemoryReactor, clock: Clock) -> HomeServer:
+        hs = self.setup_test_homeserver()
+
+        # XXX: We must create the Rust HTTP client before we call `reactor.run()` below.
+        # Twisted's `MemoryReactor` doesn't invoke `callWhenRunning` callbacks if it's
+        # already running and we rely on that to start the Tokio thread pool in Rust. In
+        # the future, this may not matter, see https://github.com/twisted/twisted/pull/12514
+        self._http_client = hs.get_proxied_http_client()
+        self._rust_http_client = HttpClient(
+            reactor=hs.get_reactor(),
+            user_agent=self._http_client.user_agent.decode("utf8"),
+        )
+
+        # This triggers the server startup hooks, which starts the Tokio thread pool
+        reactor.run()
+
+        return hs
+
+    def prepare(self, reactor: MemoryReactor, clock: Clock, hs: HomeServer) -> None:
+        self.server = StubServer()
+
+    def tearDown(self) -> None:
+        # MemoryReactor doesn't trigger the shutdown phases, and we want the
+        # Tokio thread pool to be stopped
+        # XXX: This logic should probably get moved somewhere else
+        shutdown_triggers = self.reactor.triggers.get("shutdown", {})
+        for phase in ["before", "during", "after"]:
+            triggers = shutdown_triggers.get(phase, [])
+            for callbable, args, kwargs in triggers:
+                callbable(*args, **kwargs)
+
+    def till_deferred_has_result(
+        self,
+        awaitable: Union[
+            "Coroutine[Deferred[Any], Any, T]",
+            "Generator[Deferred[Any], Any, T]",
+            "Deferred[T]",
+        ],
+    ) -> "Deferred[T]":
+        """Wait until a deferred has a result.
+
+        This is useful because the Rust HTTP client will resolve the deferred
+        using reactor.callFromThread, which are only run when we call
+        reactor.advance.
+        """
+        deferred = ensureDeferred(awaitable)
+        tries = 0
+        while not deferred.called:
+            time.sleep(0.1)
+            self.reactor.advance(0)
+            tries += 1
+            if tries > 100:
+                raise Exception("Timed out waiting for deferred to resolve")
+
+        return deferred
+
+    def _check_current_logcontext(self, expected_logcontext_string: str) -> None:
+        context = current_context()
+        assert isinstance(context, LoggingContext) or isinstance(context, _Sentinel), (
+            f"Expected LoggingContext({expected_logcontext_string}) but saw {context}"
+        )
+        self.assertEqual(
+            str(context),
+            expected_logcontext_string,
+            f"Expected LoggingContext({expected_logcontext_string}) but saw {context}",
+        )
+
+    def test_request_response(self) -> None:
+        """
+        Test to make sure we can make a basic request and get the expected
+        response.
+        """
+
+        async def do_request() -> None:
+            resp_body = await self._rust_http_client.get(
+                url=self.server.endpoint,
+                response_limit=1 * 1024 * 1024,
+            )
+            raw_response = json_decoder.decode(resp_body.decode("utf-8"))
+            self.assertEqual(raw_response, {"ok": True})
+
+        self.get_success(self.till_deferred_has_result(do_request()))
+        self.assertEqual(self.server.calls, 1)
+
+    async def test_logging_context(self) -> None:
+        """
+        Test to make sure the `LoggingContext` (logcontext) is handled correctly
+        when making requests.
+        """
+        # Sanity check that we start in the sentinel context
+        self._check_current_logcontext("sentinel")
+
+        callback_finished = False
+
+        async def do_request() -> None:
+            nonlocal callback_finished
+            try:
+                # Should have the same logcontext as the caller
+                self._check_current_logcontext("foo")
+
+                with LoggingContext(name="competing", server_name="test_server"):
+                    # Make the actual request
+                    await self._rust_http_client.get(
+                        url=self.server.endpoint,
+                        response_limit=1 * 1024 * 1024,
+                    )
+                    self._check_current_logcontext("competing")
+
+                # Back to the caller's context outside of the `LoggingContext` block
+                self._check_current_logcontext("foo")
+            finally:
+                # When exceptions happen, we still want to mark the callback as finished
+                # so that the test can complete and we see the underlying error.
+                callback_finished = True
+
+        with LoggingContext(name="foo", server_name="test_server"):
+            # Fire off the function, but don't wait on it.
+            run_in_background(do_request)
+
+            # Now wait for the function under test to have run
+            with PreserveLoggingContext():
+                while not callback_finished:
+                    # await self.hs.get_clock().sleep(0)
+                    time.sleep(0.1)
+                    self.reactor.advance(0)
+
+            # check that the logcontext is left in a sane state.
+            self._check_current_logcontext("foo")
+
+        self.assertTrue(
+            callback_finished,
+            "Callback never finished which means the test probably didn't wait long enough",
+        )
+
+        # Back to the sentinel context
+        self._check_current_logcontext("sentinel")
diff --git a/tests/test_distributor.py b/tests/test_distributor.py
index 19dafe64ed..2dd26833c8 100644
--- a/tests/test_distributor.py
+++ b/tests/test_distributor.py
@@ -26,9 +26,10 @@ from synapse.util.distributor import Distributor
 from . import unittest
 
 
-class DistributorTestCase(unittest.TestCase):
+class DistributorTestCase(unittest.HomeserverTestCase):
     def setUp(self) -> None:
-        self.dist = Distributor(server_name="test_server")
+        super().setUp()
+        self.dist = Distributor(hs=self.hs)
 
     def test_signal_dispatch(self) -> None:
         self.dist.declare("alert")
diff --git a/tests/test_event_auth.py b/tests/test_event_auth.py
index f12402f5f2..934a2fd307 100644
--- a/tests/test_event_auth.py
+++ b/tests/test_event_auth.py
@@ -20,7 +20,7 @@
 #
 
 import unittest
-from typing import Any, Collection, Dict, Iterable, List, Optional
+from typing import Any, Collection, Iterable
 
 from parameterized import parameterized
 
@@ -39,7 +39,7 @@ class _StubEventSourceStore:
     """A stub implementation of the EventSourceStore"""
 
     def __init__(self) -> None:
-        self._store: Dict[str, EventBase] = {}
+        self._store: dict[str, EventBase] = {}
 
     def add_event(self, event: EventBase) -> None:
         self._store[event.event_id] = event
@@ -54,7 +54,7 @@ class _StubEventSourceStore:
         redact_behaviour: EventRedactBehaviour,
         get_prev_content: bool = False,
         allow_rejected: bool = False,
-    ) -> Dict[str, EventBase]:
+    ) -> dict[str, EventBase]:
         assert allow_rejected
         assert not get_prev_content
         assert redact_behaviour == EventRedactBehaviour.as_is
@@ -745,7 +745,7 @@ class EventAuthTestCase(unittest.TestCase):
         test_room_v10_rejects_string_power_levels above handles the string case.
         """
 
-        def create_event(pl_event_content: Dict[str, Any]) -> EventBase:
+        def create_event(pl_event_content: dict[str, Any]) -> EventBase:
             return make_event_from_dict(
                 {
                     "room_id": TEST_ROOM_ID,
@@ -759,7 +759,7 @@ class EventAuthTestCase(unittest.TestCase):
                 room_version=RoomVersions.V10,
             )
 
-        contents: Iterable[Dict[str, Any]] = [
+        contents: Iterable[dict[str, Any]] = [
             {"notifications": {"room": None}},
             {"users": {"@alice:wonderland": []}},
             {"users_default": {}},
@@ -797,8 +797,8 @@ def _member_event(
     room_version: RoomVersion,
     user_id: str,
     membership: str,
-    sender: Optional[str] = None,
-    additional_content: Optional[dict] = None,
+    sender: str | None = None,
+    additional_content: dict | None = None,
 ) -> EventBase:
     return make_event_from_dict(
         {
@@ -818,7 +818,7 @@ def _member_event(
 def _join_event(
     room_version: RoomVersion,
     user_id: str,
-    additional_content: Optional[dict] = None,
+    additional_content: dict | None = None,
 ) -> EventBase:
     return _member_event(
         room_version,
@@ -861,7 +861,7 @@ def _alias_event(room_version: RoomVersion, sender: str, **kwargs: Any) -> Event
 
 def _build_auth_dict_for_room_version(
     room_version: RoomVersion, auth_events: Iterable[EventBase]
-) -> List:
+) -> list:
     if room_version.event_format == EventFormatVersions.ROOM_V1_V2:
         return [(e.event_id, "not_used") for e in auth_events]
     else:
@@ -871,7 +871,7 @@ def _build_auth_dict_for_room_version(
 def _random_state_event(
     room_version: RoomVersion,
     sender: str,
-    auth_events: Optional[Iterable[EventBase]] = None,
+    auth_events: Iterable[EventBase] | None = None,
 ) -> EventBase:
     if auth_events is None:
         auth_events = []
diff --git a/tests/test_mau.py b/tests/test_mau.py
index fa98242bf7..2d5c4c5d1c 100644
--- a/tests/test_mau.py
+++ b/tests/test_mau.py
@@ -20,8 +20,6 @@
 
 """Tests REST events for /rooms paths."""
 
-from typing import List, Optional
-
 from twisted.internet.testing import MemoryReactor
 
 from synapse.api.constants import APP_SERVICE_REGISTRATION_TYPE, LoginType
@@ -249,7 +247,7 @@ class TestMauLimit(unittest.HomeserverTestCase):
         }
     )
     def test_as_trial_days(self) -> None:
-        user_tokens: List[str] = []
+        user_tokens: list[str] = []
 
         def advance_time_and_sync() -> None:
             self.reactor.advance(24 * 60 * 61)
@@ -313,7 +311,7 @@ class TestMauLimit(unittest.HomeserverTestCase):
         )
 
     def create_user(
-        self, localpart: str, token: Optional[str] = None, appservice: bool = False
+        self, localpart: str, token: str | None = None, appservice: bool = False
     ) -> str:
         request_data = {
             "username": localpart,
diff --git a/tests/test_phone_home.py b/tests/test_phone_home.py
index ab21a5dde4..1d450f8251 100644
--- a/tests/test_phone_home.py
+++ b/tests/test_phone_home.py
@@ -75,7 +75,7 @@ class CommonMetricsTestCase(HomeserverTestCase):
 
     def prepare(self, reactor: MemoryReactor, clock: Clock, hs: HomeServer) -> None:
         self.metrics_manager = hs.get_common_usage_metrics_manager()
-        self.get_success(self.metrics_manager.setup())
+        self.metrics_manager.setup()
 
     def test_dau(self) -> None:
         """Tests that the daily active users count is correctly updated."""
diff --git a/tests/test_server.py b/tests/test_server.py
index 69efceafe8..2df6bdfa44 100644
--- a/tests/test_server.py
+++ b/tests/test_server.py
@@ -20,7 +20,7 @@
 
 import re
 from http import HTTPStatus
-from typing import Awaitable, Callable, Dict, NoReturn, Optional, Tuple
+from typing import Awaitable, Callable, NoReturn
 
 from twisted.internet.defer import Deferred
 from twisted.web.resource import Resource
@@ -55,9 +55,9 @@ class JsonResourceTests(unittest.TestCase):
         reactor, clock = get_clock()
         self.reactor = reactor
         self.homeserver = setup_test_homeserver(
-            self.addCleanup,
-            clock=clock,
+            cleanup_func=self.addCleanup,
             reactor=self.reactor,
+            clock=clock,
         )
 
     def test_handler_for_request(self) -> None:
@@ -70,7 +70,7 @@ class JsonResourceTests(unittest.TestCase):
 
         def _callback(
             request: SynapseRequest, **kwargs: object
-        ) -> Tuple[int, Dict[str, object]]:
+        ) -> tuple[int, dict[str, object]]:
             got_kwargs.update(kwargs)
             return 200, kwargs
 
@@ -192,7 +192,7 @@ class JsonResourceTests(unittest.TestCase):
 
         def _callback(
             request: SynapseRequest, **kwargs: object
-        ) -> Tuple[int, Dict[str, object]]:
+        ) -> tuple[int, dict[str, object]]:
             return 200, {"result": True}
 
         res = JsonResource(self.homeserver)
@@ -217,9 +217,9 @@ class OptionsResourceTests(unittest.TestCase):
         reactor, clock = get_clock()
         self.reactor = reactor
         self.homeserver = setup_test_homeserver(
-            self.addCleanup,
-            clock=clock,
+            cleanup_func=self.addCleanup,
             reactor=self.reactor,
+            clock=clock,
         )
 
         class DummyResource(Resource):
@@ -236,17 +236,17 @@ class OptionsResourceTests(unittest.TestCase):
         """Create a request from the method/path and return a channel with the response."""
         # Create a site and query for the resource.
         site = SynapseSite(
-            "test",
-            "site_tag",
-            parse_listener_def(
+            logger_name="test",
+            site_tag="site_tag",
+            config=parse_listener_def(
                 0,
                 {
                     "type": "http",
                     "port": 0,
                 },
             ),
-            self.resource,
-            "1.0",
+            resource=self.resource,
+            server_version_string="1",
             max_request_body_size=4096,
             reactor=self.reactor,
             hs=self.homeserver,
@@ -309,7 +309,7 @@ class OptionsResourceTests(unittest.TestCase):
 
 class WrapHtmlRequestHandlerTests(unittest.TestCase):
     class TestResource(DirectServeHtmlResource):
-        callback: Optional[Callable[..., Awaitable[None]]]
+        callback: Callable[..., Awaitable[None]] | None
 
         async def _async_render_GET(self, request: SynapseRequest) -> None:
             assert self.callback is not None
@@ -405,11 +405,11 @@ class CancellableDirectServeJsonResource(DirectServeJsonResource):
         self.clock = clock
 
     @cancellable
-    async def _async_render_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def _async_render_GET(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await self.clock.sleep(1.0)
         return HTTPStatus.OK, {"result": True}
 
-    async def _async_render_POST(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
+    async def _async_render_POST(self, request: SynapseRequest) -> tuple[int, JsonDict]:
         await self.clock.sleep(1.0)
         return HTTPStatus.OK, {"result": True}
 
@@ -422,11 +422,11 @@ class CancellableDirectServeHtmlResource(DirectServeHtmlResource):
         self.clock = clock
 
     @cancellable
-    async def _async_render_GET(self, request: SynapseRequest) -> Tuple[int, bytes]:
+    async def _async_render_GET(self, request: SynapseRequest) -> tuple[int, bytes]:
         await self.clock.sleep(1.0)
         return HTTPStatus.OK, b"ok"
 
-    async def _async_render_POST(self, request: SynapseRequest) -> Tuple[int, bytes]:
+    async def _async_render_POST(self, request: SynapseRequest) -> tuple[int, bytes]:
         await self.clock.sleep(1.0)
         return HTTPStatus.OK, b"ok"
 
diff --git a/tests/test_state.py b/tests/test_state.py
index 16446c16bc..7df95ebf8b 100644
--- a/tests/test_state.py
+++ b/tests/test_state.py
@@ -21,15 +21,9 @@
 from typing import (
     Any,
     Collection,
-    Dict,
     Generator,
     Iterable,
     Iterator,
-    List,
-    Optional,
-    Set,
-    Tuple,
-    cast,
 )
 from unittest.mock import AsyncMock, Mock
 
@@ -43,23 +37,22 @@ from synapse.events.snapshot import EventContext
 from synapse.state import StateHandler, StateResolutionHandler, _make_state_cache_entry
 from synapse.types import MutableStateMap, StateMap
 from synapse.types.state import StateFilter
-from synapse.util.clock import Clock
 from synapse.util.macaroons import MacaroonGenerator
 
 from tests import unittest
-
-from .utils import MockClock, default_config
+from tests.server import get_clock
+from tests.utils import default_config
 
 _next_event_id = 1000
 
 
 def create_event(
-    name: Optional[str] = None,
-    type: Optional[str] = None,
-    state_key: Optional[str] = None,
+    name: str | None = None,
+    type: str | None = None,
+    state_key: str | None = None,
     depth: int = 2,
-    event_id: Optional[str] = None,
-    prev_events: Optional[List[Tuple[str, dict]]] = None,
+    event_id: str | None = None,
+    prev_events: list[tuple[str, dict]] | None = None,
     **kwargs: Any,
 ) -> EventBase:
     global _next_event_id
@@ -93,16 +86,16 @@ def create_event(
 
 class _DummyStore:
     def __init__(self) -> None:
-        self._event_to_state_group: Dict[str, int] = {}
-        self._group_to_state: Dict[int, MutableStateMap[str]] = {}
+        self._event_to_state_group: dict[str, int] = {}
+        self._group_to_state: dict[int, MutableStateMap[str]] = {}
 
-        self._event_id_to_event: Dict[str, EventBase] = {}
+        self._event_id_to_event: dict[str, EventBase] = {}
 
         self._next_group = 1
 
     async def get_state_groups_ids(
         self, room_id: str, event_ids: Collection[str]
-    ) -> Dict[int, MutableStateMap[str]]:
+    ) -> dict[int, MutableStateMap[str]]:
         groups = {}
         for event_id in event_ids:
             group = self._event_to_state_group.get(event_id)
@@ -112,7 +105,7 @@ class _DummyStore:
         return groups
 
     async def get_state_ids_for_group(
-        self, state_group: int, state_filter: Optional[StateFilter] = None
+        self, state_group: int, state_filter: StateFilter | None = None
     ) -> MutableStateMap[str]:
         return self._group_to_state[state_group]
 
@@ -120,9 +113,9 @@ class _DummyStore:
         self,
         event_id: str,
         room_id: str,
-        prev_group: Optional[int],
-        delta_ids: Optional[StateMap[str]],
-        current_state_ids: Optional[StateMap[str]],
+        prev_group: int | None,
+        delta_ids: StateMap[str] | None,
+        current_state_ids: StateMap[str] | None,
     ) -> int:
         state_group = self._next_group
         self._next_group += 1
@@ -139,7 +132,7 @@ class _DummyStore:
 
     async def get_events(
         self, event_ids: Collection[str], **kwargs: Any
-    ) -> Dict[str, EventBase]:
+    ) -> dict[str, EventBase]:
         return {
             e_id: self._event_id_to_event[e_id]
             for e_id in event_ids
@@ -148,12 +141,12 @@ class _DummyStore:
 
     async def get_partial_state_events(
         self, event_ids: Collection[str]
-    ) -> Dict[str, bool]:
+    ) -> dict[str, bool]:
         return dict.fromkeys(event_ids, False)
 
     async def get_state_group_delta(
         self, name: str
-    ) -> Tuple[Optional[int], Optional[StateMap[str]]]:
+    ) -> tuple[int | None, StateMap[str] | None]:
         return None, None
 
     def register_events(self, events: Iterable[EventBase]) -> None:
@@ -172,7 +165,7 @@ class _DummyStore:
 
     async def get_state_group_for_events(
         self, event_ids: Collection[str], await_full_state: bool = True
-    ) -> Dict[str, int]:
+    ) -> dict[str, int]:
         res = {}
         for event in event_ids:
             res[event] = self._event_to_state_group[event]
@@ -180,7 +173,7 @@ class _DummyStore:
 
     async def get_state_for_groups(
         self, groups: Collection[int]
-    ) -> Dict[int, MutableStateMap[str]]:
+    ) -> dict[int, MutableStateMap[str]]:
         res = {}
         for group in groups:
             state = self._group_to_state[group]
@@ -195,15 +188,15 @@ class DictObj(dict):
 
 
 class Graph:
-    def __init__(self, nodes: Dict[str, DictObj], edges: Dict[str, List[str]]):
-        events: Dict[str, EventBase] = {}
-        clobbered: Set[str] = set()
+    def __init__(self, nodes: dict[str, DictObj], edges: dict[str, list[str]]):
+        events: dict[str, EventBase] = {}
+        clobbered: set[str] = set()
 
         for event_id, fields in nodes.items():
             refs = edges.get(event_id)
             if refs:
                 clobbered.difference_update(refs)
-                prev_events: List[Tuple[str, dict]] = [(r, {}) for r in refs]
+                prev_events: list[tuple[str, dict]] = [(r, {}) for r in refs]
             else:
                 prev_events = []
 
@@ -248,7 +241,7 @@ class StateTestCase(unittest.TestCase):
                 "hostname",
             ]
         )
-        clock = cast(Clock, MockClock())
+        reactor, clock = get_clock()
         hs.config = default_config("tesths", True)
         hs.get_datastores.return_value = Mock(
             main=self.dummy_store,
@@ -283,7 +276,7 @@ class StateTestCase(unittest.TestCase):
 
         self.dummy_store.register_events(graph.walk())
 
-        context_store: Dict[str, EventContext] = {}
+        context_store: dict[str, EventContext] = {}
 
         for event in graph.walk():
             context = yield defer.ensureDeferred(
@@ -330,7 +323,7 @@ class StateTestCase(unittest.TestCase):
 
         self.dummy_store.register_events(graph.walk())
 
-        context_store: Dict[str, EventContext] = {}
+        context_store: dict[str, EventContext] = {}
 
         for event in graph.walk():
             context = yield defer.ensureDeferred(
@@ -391,7 +384,7 @@ class StateTestCase(unittest.TestCase):
 
         self.dummy_store.register_events(graph.walk())
 
-        context_store: Dict[str, EventContext] = {}
+        context_store: dict[str, EventContext] = {}
 
         for event in graph.walk():
             context = yield defer.ensureDeferred(
@@ -469,7 +462,7 @@ class StateTestCase(unittest.TestCase):
 
         self.dummy_store.register_events(graph.walk())
 
-        context_store: Dict[str, EventContext] = {}
+        context_store: dict[str, EventContext] = {}
 
         for event in graph.walk():
             context = yield defer.ensureDeferred(
@@ -492,7 +485,7 @@ class StateTestCase(unittest.TestCase):
         self.assertEqual(ctx_d.state_group_before_event, ctx_d.state_group)
 
     def _add_depths(
-        self, nodes: Dict[str, DictObj], edges: Dict[str, List[str]]
+        self, nodes: dict[str, DictObj], edges: dict[str, list[str]]
     ) -> None:
         def _get_depth(ev: str) -> int:
             node = nodes[ev]
diff --git a/tests/test_test_utils.py b/tests/test_test_utils.py
deleted file mode 100644
index c52f963a7e..0000000000
--- a/tests/test_test_utils.py
+++ /dev/null
@@ -1,79 +0,0 @@
-#
-# This file is licensed under the Affero General Public License (AGPL) version 3.
-#
-# Copyright 2014-2016 OpenMarket Ltd
-# Copyright (C) 2023 New Vector, Ltd
-#
-# This program is free software: you can redistribute it and/or modify
-# it under the terms of the GNU Affero General Public License as
-# published by the Free Software Foundation, either version 3 of the
-# License, or (at your option) any later version.
-#
-# See the GNU Affero General Public License for more details:
-# <https://www.gnu.org/licenses/agpl-3.0.html>.
-#
-# Originally licensed under the Apache License, Version 2.0:
-# <http://www.apache.org/licenses/LICENSE-2.0>.
-#
-# [This file includes modifications made by New Vector Limited]
-#
-#
-
-from tests import unittest
-from tests.utils import MockClock
-
-
-class MockClockTestCase(unittest.TestCase):
-    def setUp(self) -> None:
-        self.clock = MockClock()
-
-    def test_advance_time(self) -> None:
-        start_time = self.clock.time()
-
-        self.clock.advance_time(20)
-
-        self.assertEqual(20, self.clock.time() - start_time)
-
-    def test_later(self) -> None:
-        invoked = [0, 0]
-
-        def _cb0() -> None:
-            invoked[0] = 1
-
-        self.clock.call_later(10, _cb0)
-
-        def _cb1() -> None:
-            invoked[1] = 1
-
-        self.clock.call_later(20, _cb1)
-
-        self.assertFalse(invoked[0])
-
-        self.clock.advance_time(15)
-
-        self.assertTrue(invoked[0])
-        self.assertFalse(invoked[1])
-
-        self.clock.advance_time(5)
-
-        self.assertTrue(invoked[1])
-
-    def test_cancel_later(self) -> None:
-        invoked = [0, 0]
-
-        def _cb0() -> None:
-            invoked[0] = 1
-
-        t0 = self.clock.call_later(10, _cb0)
-
-        def _cb1() -> None:
-            invoked[1] = 1
-
-        self.clock.call_later(20, _cb1)
-
-        self.clock.cancel_call_later(t0)
-
-        self.clock.advance_time(30)
-
-        self.assertFalse(invoked[0])
-        self.assertTrue(invoked[1])
diff --git a/tests/test_types.py b/tests/test_types.py
index 0c08bc8ecc..1802f0fae3 100644
--- a/tests/test_types.py
+++ b/tests/test_types.py
@@ -19,7 +19,6 @@
 #
 #
 
-from typing import Type
 from unittest import skipUnless
 
 from immutabledict import immutabledict
@@ -152,7 +151,7 @@ class MapUsernameTestCase(unittest.TestCase):
 class MultiWriterTokenTestCase(unittest.HomeserverTestCase):
     """Tests for the different types of multi writer tokens."""
 
-    token_type: Type[AbstractMultiWriterStreamToken]
+    token_type: type[AbstractMultiWriterStreamToken]
 
     def test_basic_token(self) -> None:
         """Test that a simple stream token can be serialized and unserialized"""
diff --git a/tests/test_utils/__init__.py b/tests/test_utils/__init__.py
index 3e6fd03600..0df5a4e6c3 100644
--- a/tests/test_utils/__init__.py
+++ b/tests/test_utils/__init__.py
@@ -28,7 +28,7 @@ import json
 import sys
 import warnings
 from binascii import unhexlify
-from typing import TYPE_CHECKING, Awaitable, Callable, Tuple, TypeVar
+from typing import TYPE_CHECKING, Awaitable, Callable, TypeVar
 
 import attr
 import zope.interface
@@ -102,7 +102,7 @@ class FakeResponse:  # type: ignore[misc]
     attribute, and didn't support deliverBody until recently.
     """
 
-    version: Tuple[bytes, int, int] = (b"HTTP", 1, 1)
+    version: tuple[bytes, int, int] = (b"HTTP", 1, 1)
 
     # HTTP response code
     code: int = 200
diff --git a/tests/test_utils/event_injection.py b/tests/test_utils/event_injection.py
index c1eaf9a575..a90fc5884d 100644
--- a/tests/test_utils/event_injection.py
+++ b/tests/test_utils/event_injection.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Any, List, Optional, Tuple
+from typing import Any
 
 import synapse.server
 from synapse.api.constants import EventTypes
@@ -36,8 +36,8 @@ async def inject_member_event(
     room_id: str,
     sender: str,
     membership: str,
-    target: Optional[str] = None,
-    extra_content: Optional[dict] = None,
+    target: str | None = None,
+    extra_content: dict | None = None,
     **kwargs: Any,
 ) -> EventBase:
     """Inject a membership event into a room."""
@@ -61,8 +61,8 @@ async def inject_member_event(
 
 async def inject_event(
     hs: synapse.server.HomeServer,
-    room_version: Optional[str] = None,
-    prev_event_ids: Optional[List[str]] = None,
+    room_version: str | None = None,
+    prev_event_ids: list[str] | None = None,
     **kwargs: Any,
 ) -> EventBase:
     """Inject a generic event into a room
@@ -86,10 +86,10 @@ async def inject_event(
 
 async def create_event(
     hs: synapse.server.HomeServer,
-    room_version: Optional[str] = None,
-    prev_event_ids: Optional[List[str]] = None,
+    room_version: str | None = None,
+    prev_event_ids: list[str] | None = None,
     **kwargs: Any,
-) -> Tuple[EventBase, EventContext]:
+) -> tuple[EventBase, EventContext]:
     if room_version is None:
         room_version = await hs.get_datastores().main.get_room_version_id(
             kwargs["room_id"]
diff --git a/tests/test_utils/html_parsers.py b/tests/test_utils/html_parsers.py
index a0f39cb130..a9a4b98df2 100644
--- a/tests/test_utils/html_parsers.py
+++ b/tests/test_utils/html_parsers.py
@@ -20,7 +20,7 @@
 #
 
 from html.parser import HTMLParser
-from typing import Dict, Iterable, List, NoReturn, Optional, Tuple
+from typing import Iterable, NoReturn
 
 
 class TestHtmlParser(HTMLParser):
@@ -30,16 +30,16 @@ class TestHtmlParser(HTMLParser):
         super().__init__()
 
         # a list of links found in the doc
-        self.links: List[str] = []
+        self.links: list[str] = []
 
         # the values of any hidden <input>s: map from name to value
-        self.hiddens: Dict[str, Optional[str]] = {}
+        self.hiddens: dict[str, str | None] = {}
 
         # the values of any radio buttons: map from name to list of values
-        self.radios: Dict[str, List[Optional[str]]] = {}
+        self.radios: dict[str, list[str | None]] = {}
 
     def handle_starttag(
-        self, tag: str, attrs: Iterable[Tuple[str, Optional[str]]]
+        self, tag: str, attrs: Iterable[tuple[str, str | None]]
     ) -> None:
         attr_dict = dict(attrs)
         if tag == "a":
diff --git a/tests/test_utils/oidc.py b/tests/test_utils/oidc.py
index f2de8bded5..837a04077c 100644
--- a/tests/test_utils/oidc.py
+++ b/tests/test_utils/oidc.py
@@ -23,7 +23,7 @@
 import base64
 import json
 from hashlib import sha256
-from typing import Any, ContextManager, Dict, List, Optional, Tuple
+from typing import Any, ContextManager
 from unittest.mock import Mock, patch
 from urllib.parse import parse_qs
 
@@ -45,8 +45,8 @@ class FakeAuthorizationGrant:
     client_id: str
     redirect_uri: str
     scope: str
-    nonce: Optional[str]
-    sid: Optional[str]
+    nonce: str | None
+    sid: str | None
 
 
 class FakeOidcServer:
@@ -75,16 +75,16 @@ class FakeOidcServer:
         self.post_token_handler = Mock(side_effect=self._post_token_handler)
 
         # A code -> grant mapping
-        self._authorization_grants: Dict[str, FakeAuthorizationGrant] = {}
+        self._authorization_grants: dict[str, FakeAuthorizationGrant] = {}
         # An access token -> grant mapping
-        self._sessions: Dict[str, FakeAuthorizationGrant] = {}
+        self._sessions: dict[str, FakeAuthorizationGrant] = {}
 
         # We generate here an ECDSA key with the P-256 curve (ES256 algorithm) used for
         # signing JWTs. ECDSA keys are really quick to generate compared to RSA.
         self._key = ECKey.generate_key(crv="P-256", is_private=True)
         self._jwks = KeySet([ECKey.import_key(self._key.as_pem(is_private=False))])
 
-        self._id_token_overrides: Dict[str, Any] = {}
+        self._id_token_overrides: dict[str, Any] = {}
 
     def reset_mocks(self) -> None:
         self.request.reset_mock()
@@ -140,7 +140,7 @@ class FakeOidcServer:
     def get_jwks(self) -> dict:
         return self._jwks.as_dict()
 
-    def get_userinfo(self, access_token: str) -> Optional[dict]:
+    def get_userinfo(self, access_token: str) -> dict | None:
         """Given an access token, get the userinfo of the associated session."""
         session = self._sessions.get(access_token, None)
         if session is None:
@@ -220,9 +220,9 @@ class FakeOidcServer:
         scope: str,
         redirect_uri: str,
         userinfo: dict,
-        nonce: Optional[str] = None,
+        nonce: str | None = None,
         with_sid: bool = False,
-    ) -> Tuple[str, FakeAuthorizationGrant]:
+    ) -> tuple[str, FakeAuthorizationGrant]:
         """Start an authorization request, and get back the code to use on the authorization endpoint."""
         code = random_string(10)
         sid = None
@@ -242,7 +242,7 @@ class FakeOidcServer:
 
         return code, grant
 
-    def exchange_code(self, code: str) -> Optional[Dict[str, Any]]:
+    def exchange_code(self, code: str) -> dict[str, Any] | None:
         grant = self._authorization_grants.pop(code, None)
         if grant is None:
             return None
@@ -269,7 +269,7 @@ class FakeOidcServer:
         metadata: bool = False,
         token: bool = False,
         userinfo: bool = False,
-    ) -> ContextManager[Dict[str, Mock]]:
+    ) -> ContextManager[dict[str, Mock]]:
         """A context which makes a set of endpoints return a 500 error.
 
         Args:
@@ -296,11 +296,11 @@ class FakeOidcServer:
         self,
         method: str,
         uri: str,
-        data: Optional[bytes] = None,
-        headers: Optional[Headers] = None,
+        data: bytes | None = None,
+        headers: Headers | None = None,
     ) -> IResponse:
         """The override of the SimpleHttpClient#request() method"""
-        access_token: Optional[str] = None
+        access_token: str | None = None
 
         if headers is None:
             headers = Headers()
@@ -346,7 +346,7 @@ class FakeOidcServer:
         """Handles requests to the OIDC well-known document."""
         return FakeResponse.json(payload=self.get_metadata())
 
-    def _get_userinfo_handler(self, access_token: Optional[str]) -> IResponse:
+    def _get_userinfo_handler(self, access_token: str | None) -> IResponse:
         """Handles requests to the userinfo endpoint."""
         if access_token is None:
             return FakeResponse(code=401)
@@ -356,7 +356,7 @@ class FakeOidcServer:
 
         return FakeResponse.json(payload=user_info)
 
-    def _post_token_handler(self, params: Dict[str, List[str]]) -> IResponse:
+    def _post_token_handler(self, params: dict[str, list[str]]) -> IResponse:
         """Handles requests to the token endpoint."""
         code = params.get("code", [])
 
diff --git a/tests/test_visibility.py b/tests/test_visibility.py
index 9a8cad6454..06598c29de 100644
--- a/tests/test_visibility.py
+++ b/tests/test_visibility.py
@@ -18,7 +18,6 @@
 #
 #
 import logging
-from typing import Optional
 from unittest.mock import patch
 
 from twisted.test.proto_helpers import MemoryReactor
@@ -693,9 +692,9 @@ async def inject_message_event(
     hs: HomeServer,
     room_id: str,
     sender: str,
-    body: Optional[str] = "testytest",
-    soft_failed: Optional[bool] = False,
-    policy_server_spammy: Optional[bool] = False,
+    body: str | None = "testytest",
+    soft_failed: bool | None = False,
+    policy_server_spammy: bool | None = False,
 ) -> EventBase:
     return await inject_event(
         hs,
diff --git a/tests/unittest.py b/tests/unittest.py
index 8be4e635a5..7ea29364db 100644
--- a/tests/unittest.py
+++ b/tests/unittest.py
@@ -33,18 +33,12 @@ from typing import (
     Awaitable,
     Callable,
     ClassVar,
-    Dict,
     Generic,
     Iterable,
-    List,
     Mapping,
     NoReturn,
-    Optional,
     Protocol,
-    Tuple,
-    Type,
     TypeVar,
-    Union,
 )
 from unittest.mock import Mock, patch
 
@@ -80,7 +74,7 @@ from synapse.logging.context import (
 from synapse.rest import RegisterServletsFunc
 from synapse.server import HomeServer
 from synapse.storage.keys import FetchKeyResult
-from synapse.types import JsonDict, Requester, UserID, create_requester
+from synapse.types import ISynapseReactor, JsonDict, Requester, UserID, create_requester
 from synapse.util.clock import Clock
 from synapse.util.httpresourcetree import create_resource_tree
 
@@ -99,6 +93,8 @@ from tests.utils import checked_cast, default_config, setupdb
 setupdb()
 setup_logging()
 
+logger = logging.getLogger(__name__)
+
 TV = TypeVar("TV")
 _ExcType = TypeVar("_ExcType", bound=BaseException, covariant=True)
 
@@ -135,7 +131,7 @@ def around(target: TV) -> Callable[[Callable[Concatenate[S, P], R]], None]:
     return _around
 
 
-_TConfig = TypeVar("_TConfig", Config, RootConfig)
+_TConfig = TypeVar("_TConfig", Config, HomeServerConfig)
 
 
 def deepcopy_config(config: _TConfig) -> _TConfig:
@@ -161,13 +157,13 @@ def deepcopy_config(config: _TConfig) -> _TConfig:
 
 
 @functools.lru_cache(maxsize=8)
-def _parse_config_dict(config: str) -> RootConfig:
+def _parse_config_dict(config: str) -> HomeServerConfig:
     config_obj = HomeServerConfig()
     config_obj.parse_config_dict(json.loads(config), "", "")
     return config_obj
 
 
-def make_homeserver_config_obj(config: Dict[str, Any]) -> RootConfig:
+def make_homeserver_config_obj(config: dict[str, Any]) -> HomeServerConfig:
     """Creates a :class:`HomeServerConfig` instance with the given configuration dict.
 
     This is equivalent to::
@@ -248,7 +244,7 @@ class TestCase(unittest.TestCase):
 
             return ret
 
-    def assertObjectHasAttributes(self, attrs: Dict[str, object], obj: object) -> None:
+    def assertObjectHasAttributes(self, attrs: dict[str, object], obj: object) -> None:
         """Asserts that the given object has each of the attributes given, and
         that the value of each matches according to assertEqual."""
         for key in attrs.keys():
@@ -276,7 +272,7 @@ class TestCase(unittest.TestCase):
         actual_items: AbstractSet[TV],
         expected_items: AbstractSet[TV],
         exact: bool = False,
-        message: Optional[str] = None,
+        message: str | None = None,
     ) -> None:
         """
         Assert that all of the `expected_items` are included in the `actual_items`.
@@ -297,14 +293,14 @@ class TestCase(unittest.TestCase):
         elif not exact and actual_items >= expected_items:
             return
 
-        expected_lines: List[str] = []
+        expected_lines: list[str] = []
         for expected_item in expected_items:
             is_expected_in_actual = expected_item in actual_items
             expected_lines.append(
                 "{}  {}".format(" " if is_expected_in_actual else "?", expected_item)
             )
 
-        actual_lines: List[str] = []
+        actual_lines: list[str] = []
         for actual_item in actual_items:
             is_actual_in_expected = actual_item in expected_items
             actual_lines.append(
@@ -343,6 +339,9 @@ def logcontext_clean(target: TV) -> TV:
     """
 
     def logcontext_error(msg: str) -> NoReturn:
+        # Log so we can still see it in the logs like normal
+        logger.warning(msg)
+        # But also fail the test
         raise AssertionError("logcontext error: %s" % (msg))
 
     patcher = patch("synapse.logging.context.logcontext_error", new=logcontext_error)
@@ -377,7 +376,7 @@ class HomeserverTestCase(TestCase):
 
     hijack_auth: ClassVar[bool] = True
     needs_threadpool: ClassVar[bool] = False
-    servlets: ClassVar[List[RegisterServletsFunc]] = []
+    servlets: ClassVar[list[RegisterServletsFunc]] = []
 
     def __init__(self, methodName: str):
         super().__init__(methodName)
@@ -392,8 +391,8 @@ class HomeserverTestCase(TestCase):
         hijacking the authentication system to return a fixed user, and then
         calling the prepare function.
         """
+        # We need to share the reactor between the homeserver and all of our test utils.
         self.reactor, self.clock = get_clock()
-        self._hs_args = {"clock": self.clock, "reactor": self.reactor}
         self.hs = self.make_homeserver(self.reactor, self.clock)
 
         self.hs.get_datastores().main.tests_allow_no_chain_cover_index = False
@@ -511,7 +510,7 @@ class HomeserverTestCase(TestCase):
 
         Function to be overridden in subclasses.
         """
-        hs = self.setup_test_homeserver()
+        hs = self.setup_test_homeserver(reactor=reactor, clock=clock)
         return hs
 
     def create_test_resource(self) -> Resource:
@@ -525,7 +524,7 @@ class HomeserverTestCase(TestCase):
         create_resource_tree(self.create_resource_dict(), root_resource)
         return root_resource
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         """Create a resource tree for the test server
 
         A resource tree is a mapping from path to twisted.web.resource.
@@ -572,17 +571,17 @@ class HomeserverTestCase(TestCase):
 
     def make_request(
         self,
-        method: Union[bytes, str],
-        path: Union[bytes, str],
-        content: Union[bytes, str, JsonDict] = b"",
-        access_token: Optional[str] = None,
-        request: Type[Request] = SynapseRequest,
+        method: bytes | str,
+        path: bytes | str,
+        content: bytes | str | JsonDict = b"",
+        access_token: str | None = None,
+        request: type[Request] = SynapseRequest,
         shorthand: bool = True,
-        federation_auth_origin: Optional[bytes] = None,
-        content_type: Optional[bytes] = None,
+        federation_auth_origin: bytes | None = None,
+        content_type: bytes | None = None,
         content_is_form: bool = False,
         await_result: bool = True,
-        custom_headers: Optional[Iterable[CustomHeaderType]] = None,
+        custom_headers: Iterable[CustomHeaderType] | None = None,
         client_ip: str = "127.0.0.1",
     ) -> FakeChannel:
         """
@@ -634,7 +633,12 @@ class HomeserverTestCase(TestCase):
         )
 
     def setup_test_homeserver(
-        self, server_name: Optional[str] = None, **kwargs: Any
+        self,
+        server_name: str | None = None,
+        config: JsonDict | None = None,
+        reactor: ISynapseReactor | None = None,
+        clock: Clock | None = None,
+        **extra_homeserver_attributes: Any,
     ) -> HomeServer:
         """
         Set up the test homeserver, meant to be called by the overridable
@@ -647,12 +651,15 @@ class HomeserverTestCase(TestCase):
         Returns:
             synapse.server.HomeServer
         """
-        kwargs = dict(kwargs)
-        kwargs.update(self._hs_args)
-        if "config" not in kwargs:
+        if config is None:
             config = self.default_config()
-        else:
-            config = kwargs["config"]
+
+        # The sane default is to use the same reactor and clock as our other test utils
+        if reactor is None:
+            reactor = self.reactor
+
+        if clock is None:
+            clock = self.clock
 
         # The server name can be specified using either the `name` argument or a config
         # override. The `name` argument takes precedence over any config overrides.
@@ -661,19 +668,24 @@ class HomeserverTestCase(TestCase):
 
         # Parse the config from a config dict into a HomeServerConfig
         config_obj = make_homeserver_config_obj(config)
-        kwargs["config"] = config_obj
 
         # The server name in the config is now `name`, if provided, or the `server_name`
         # from a config override, or the default of "test". Whichever it is, we
         # construct a homeserver with a matching name.
         server_name = config_obj.server.server_name
-        kwargs["name"] = server_name
 
         async def run_bg_updates() -> None:
             with LoggingContext(name="run_bg_updates", server_name=server_name):
                 self.get_success(stor.db_pool.updates.run_background_updates(False))
 
-        hs = setup_test_homeserver(self.addCleanup, **kwargs)
+        hs = setup_test_homeserver(
+            cleanup_func=self.addCleanup,
+            server_name=server_name,
+            config=config_obj,
+            reactor=reactor,
+            clock=clock,
+            **extra_homeserver_attributes,
+        )
         stor = hs.get_datastores().main
 
         # Run the database background updates, when running against "master".
@@ -694,7 +706,7 @@ class HomeserverTestCase(TestCase):
         return self.successResultOf(deferred)
 
     def get_failure(
-        self, d: Awaitable[Any], exc: Type[_ExcType], by: float = 0.0
+        self, d: Awaitable[Any], exc: type[_ExcType], by: float = 0.0
     ) -> _TypedFailure[_ExcType]:
         """
         Run a Deferred and get a Failure from it. The failure must be of the type `exc`.
@@ -732,8 +744,8 @@ class HomeserverTestCase(TestCase):
         self,
         username: str,
         password: str,
-        admin: Optional[bool] = False,
-        displayname: Optional[str] = None,
+        admin: bool | None = False,
+        displayname: str | None = None,
     ) -> str:
         """
         Register a user. Requires the Admin API be registered.
@@ -784,7 +796,7 @@ class HomeserverTestCase(TestCase):
         username: str,
         appservice_token: str,
         inhibit_login: bool = False,
-    ) -> Tuple[str, Optional[str]]:
+    ) -> tuple[str, str | None]:
         """Register an appservice user as an application service.
         Requires the client-facing registration API be registered.
 
@@ -815,9 +827,9 @@ class HomeserverTestCase(TestCase):
         self,
         username: str,
         password: str,
-        device_id: Optional[str] = None,
-        additional_request_fields: Optional[Dict[str, str]] = None,
-        custom_headers: Optional[Iterable[CustomHeaderType]] = None,
+        device_id: str | None = None,
+        additional_request_fields: dict[str, str] | None = None,
+        custom_headers: Iterable[CustomHeaderType] | None = None,
     ) -> str:
         """
         Log in a user, and get an access token. Requires the Login API be registered.
@@ -856,7 +868,7 @@ class HomeserverTestCase(TestCase):
         room_id: str,
         user: UserID,
         soft_failed: bool = False,
-        prev_event_ids: Optional[List[str]] = None,
+        prev_event_ids: list[str] | None = None,
     ) -> str:
         """
         Create and send an event.
@@ -948,7 +960,7 @@ class FederatingHomeserverTestCase(HomeserverTestCase):
             )
         )
 
-    def create_resource_dict(self) -> Dict[str, Resource]:
+    def create_resource_dict(self) -> dict[str, Resource]:
         d = super().create_resource_dict()
         d["/_matrix/federation"] = TransportLayerServer(self.hs)
         return d
@@ -957,9 +969,9 @@ class FederatingHomeserverTestCase(HomeserverTestCase):
         self,
         method: str,
         path: str,
-        content: Optional[JsonDict] = None,
+        content: JsonDict | None = None,
         await_result: bool = True,
-        custom_headers: Optional[Iterable[CustomHeaderType]] = None,
+        custom_headers: Iterable[CustomHeaderType] | None = None,
         client_ip: str = "127.0.0.1",
     ) -> FakeChannel:
         """Make an inbound signed federation request to this server
@@ -1024,7 +1036,7 @@ def _auth_header_for_request(
     signing_key: signedjson.key.SigningKey,
     method: str,
     path: str,
-    content: Optional[JsonDict],
+    content: JsonDict | None,
 ) -> str:
     """Build a suitable Authorization header for an outgoing federation request"""
     request_description: JsonDict = {
diff --git a/tests/util/caches/test_deferred_cache.py b/tests/util/caches/test_deferred_cache.py
index 7017d6d70a..fc01a2f5e9 100644
--- a/tests/util/caches/test_deferred_cache.py
+++ b/tests/util/caches/test_deferred_cache.py
@@ -20,26 +20,31 @@
 #
 
 from functools import partial
-from typing import List, Tuple
 
 from twisted.internet import defer
 
 from synapse.util.caches.deferred_cache import DeferredCache
 
+from tests.server import get_clock
 from tests.unittest import TestCase
 
 
 class DeferredCacheTestCase(TestCase):
+    def setUp(self) -> None:
+        super().setUp()
+
+        _, self.clock = get_clock()
+
     def test_empty(self) -> None:
         cache: DeferredCache[str, int] = DeferredCache(
-            name="test", server_name="test_server"
+            name="test", clock=self.clock, server_name="test_server"
         )
         with self.assertRaises(KeyError):
             cache.get("foo")
 
     def test_hit(self) -> None:
         cache: DeferredCache[str, int] = DeferredCache(
-            name="test", server_name="test_server"
+            name="test", clock=self.clock, server_name="test_server"
         )
         cache.prefill("foo", 123)
 
@@ -47,7 +52,7 @@ class DeferredCacheTestCase(TestCase):
 
     def test_hit_deferred(self) -> None:
         cache: DeferredCache[str, int] = DeferredCache(
-            name="test", server_name="test_server"
+            name="test", clock=self.clock, server_name="test_server"
         )
         origin_d: "defer.Deferred[int]" = defer.Deferred()
         set_d = cache.set("k1", origin_d)
@@ -72,7 +77,7 @@ class DeferredCacheTestCase(TestCase):
     def test_callbacks(self) -> None:
         """Invalidation callbacks are called at the right time"""
         cache: DeferredCache[str, int] = DeferredCache(
-            name="test", server_name="test_server"
+            name="test", clock=self.clock, server_name="test_server"
         )
         callbacks = set()
 
@@ -107,7 +112,7 @@ class DeferredCacheTestCase(TestCase):
 
     def test_set_fail(self) -> None:
         cache: DeferredCache[str, int] = DeferredCache(
-            name="test", server_name="test_server"
+            name="test", clock=self.clock, server_name="test_server"
         )
         callbacks = set()
 
@@ -146,7 +151,7 @@ class DeferredCacheTestCase(TestCase):
 
     def test_get_immediate(self) -> None:
         cache: DeferredCache[str, int] = DeferredCache(
-            name="test", server_name="test_server"
+            name="test", clock=self.clock, server_name="test_server"
         )
         d1: "defer.Deferred[int]" = defer.Deferred()
         cache.set("key1", d1)
@@ -163,8 +168,8 @@ class DeferredCacheTestCase(TestCase):
         self.assertEqual(v, 2)
 
     def test_invalidate(self) -> None:
-        cache: DeferredCache[Tuple[str], int] = DeferredCache(
-            name="test", server_name="test_server"
+        cache: DeferredCache[tuple[str], int] = DeferredCache(
+            name="test", clock=self.clock, server_name="test_server"
         )
         cache.prefill(("foo",), 123)
         cache.invalidate(("foo",))
@@ -174,7 +179,7 @@ class DeferredCacheTestCase(TestCase):
 
     def test_invalidate_all(self) -> None:
         cache: DeferredCache[str, str] = DeferredCache(
-            name="testcache", server_name="test_server"
+            name="testcache", clock=self.clock, server_name="test_server"
         )
 
         callback_record = [False, False]
@@ -220,6 +225,7 @@ class DeferredCacheTestCase(TestCase):
     def test_eviction(self) -> None:
         cache: DeferredCache[int, str] = DeferredCache(
             name="test",
+            clock=self.clock,
             server_name="test_server",
             max_entries=2,
             apply_cache_factor_from_config=False,
@@ -238,6 +244,7 @@ class DeferredCacheTestCase(TestCase):
     def test_eviction_lru(self) -> None:
         cache: DeferredCache[int, str] = DeferredCache(
             name="test",
+            clock=self.clock,
             server_name="test_server",
             max_entries=2,
             apply_cache_factor_from_config=False,
@@ -258,8 +265,9 @@ class DeferredCacheTestCase(TestCase):
         cache.get(3)
 
     def test_eviction_iterable(self) -> None:
-        cache: DeferredCache[int, List[str]] = DeferredCache(
+        cache: DeferredCache[int, list[str]] = DeferredCache(
             name="test",
+            clock=self.clock,
             server_name="test_server",
             max_entries=3,
             apply_cache_factor_from_config=False,
diff --git a/tests/util/caches/test_descriptors.py b/tests/util/caches/test_descriptors.py
index 3eb502f902..3fab6c4c57 100644
--- a/tests/util/caches/test_descriptors.py
+++ b/tests/util/caches/test_descriptors.py
@@ -23,12 +23,8 @@ from typing import (
     Any,
     Generator,
     Iterable,
-    List,
     Mapping,
     NoReturn,
-    Optional,
-    Set,
-    Tuple,
     cast,
 )
 from unittest import mock
@@ -49,6 +45,7 @@ from synapse.util.caches import descriptors
 from synapse.util.caches.descriptors import _CacheContext, cached, cachedList
 
 from tests import unittest
+from tests.server import get_clock
 from tests.test_utils import get_awaitable_result
 
 logger = logging.getLogger(__name__)
@@ -56,7 +53,10 @@ logger = logging.getLogger(__name__)
 
 def run_on_reactor() -> "Deferred[int]":
     d: "Deferred[int]" = Deferred()
-    cast(IReactorTime, reactor).callLater(0, d.callback, 0)
+    # mypy ignored here because:
+    #   - this is part of the test infrastructure (outside of Synapse) so tracking
+    #     these calls for for homeserver shutdown doesn't make sense.
+    cast(IReactorTime, reactor).callLater(0, d.callback, 0)  # type: ignore[call-later-not-tracked]
     return make_deferred_yieldable(d)
 
 
@@ -67,6 +67,7 @@ class DescriptorTestCase(unittest.TestCase):
             def __init__(self) -> None:
                 self.mock = mock.Mock()
                 self.server_name = "test_server"
+                _, self.clock = get_clock()  # nb must be called this for @cached
 
             @descriptors.cached()
             def fn(self, arg1: int, arg2: int) -> str:
@@ -102,6 +103,7 @@ class DescriptorTestCase(unittest.TestCase):
             def __init__(self) -> None:
                 self.mock = mock.Mock()
                 self.server_name = "test_server"
+                _, self.clock = get_clock()  # nb must be called this for @cached
 
             @descriptors.cached(num_args=1)
             def fn(self, arg1: int, arg2: int) -> str:
@@ -148,6 +150,7 @@ class DescriptorTestCase(unittest.TestCase):
             def __init__(self) -> None:
                 self.mock = mock.Mock()
                 self.server_name = "test_server"
+                _, self.clock = get_clock()  # nb must be called this for @cached
 
         obj = Cls()
         obj.mock.return_value = "fish"
@@ -179,6 +182,7 @@ class DescriptorTestCase(unittest.TestCase):
             def __init__(self) -> None:
                 self.mock = mock.Mock()
                 self.server_name = "test_server"
+                _, self.clock = get_clock()  # nb must be called this for @cached
 
             @descriptors.cached()
             def fn(self, arg1: int, kwarg1: int = 2) -> str:
@@ -214,6 +218,7 @@ class DescriptorTestCase(unittest.TestCase):
 
         class Cls:
             server_name = "test_server"  # nb must be called this for @cached
+            _, clock = get_clock()  # nb must be called this for @cached
 
             @cached()
             def fn(self, arg1: int) -> NoReturn:
@@ -236,9 +241,10 @@ class DescriptorTestCase(unittest.TestCase):
         """The wrapped function returns a failure"""
 
         class Cls:
-            result: Optional[Deferred] = None
+            result: Deferred | None = None
             call_count = 0
             server_name = "test_server"  # nb must be called this for @cached
+            _, clock = get_clock()  # nb must be called this for @cached
 
             @cached()
             def fn(self, arg1: int) -> Deferred:
@@ -247,7 +253,7 @@ class DescriptorTestCase(unittest.TestCase):
                 return self.result
 
         obj = Cls()
-        callbacks: Set[str] = set()
+        callbacks: set[str] = set()
 
         # set off an asynchronous request
         origin_d: Deferred = Deferred()
@@ -293,6 +299,7 @@ class DescriptorTestCase(unittest.TestCase):
 
         class Cls:
             server_name = "test_server"
+            _, clock = get_clock()  # nb must be called this for @cached
 
             @descriptors.cached()
             def fn(self, arg1: int) -> "Deferred[int]":
@@ -337,6 +344,7 @@ class DescriptorTestCase(unittest.TestCase):
 
         class Cls:
             server_name = "test_server"
+            _, clock = get_clock()  # nb must be called this for @cached
 
             @descriptors.cached()
             def fn(self, arg1: int) -> Deferred:
@@ -381,6 +389,7 @@ class DescriptorTestCase(unittest.TestCase):
             def __init__(self) -> None:
                 self.mock = mock.Mock()
                 self.server_name = "test_server"
+                _, self.clock = get_clock()  # nb must be called this for @cached
 
             @descriptors.cached()
             def fn(self, arg1: int, arg2: int = 2, arg3: int = 3) -> str:
@@ -419,9 +428,10 @@ class DescriptorTestCase(unittest.TestCase):
             def __init__(self) -> None:
                 self.mock = mock.Mock()
                 self.server_name = "test_server"
+                _, self.clock = get_clock()  # nb must be called this for @cached
 
             @descriptors.cached(iterable=True)
-            def fn(self, arg1: int, arg2: int) -> Tuple[str, ...]:
+            def fn(self, arg1: int, arg2: int) -> tuple[str, ...]:
                 return self.mock(arg1, arg2)
 
         obj = Cls()
@@ -453,6 +463,7 @@ class DescriptorTestCase(unittest.TestCase):
 
         class Cls:
             server_name = "test_server"
+            _, clock = get_clock()  # nb must be called this for @cached
 
             @descriptors.cached(iterable=True)
             def fn(self, arg1: int) -> NoReturn:
@@ -476,6 +487,7 @@ class DescriptorTestCase(unittest.TestCase):
 
         class Cls:
             server_name = "test_server"  # nb must be called this for @cached
+            _, clock = get_clock()  # nb must be called this for @cached
 
             @cached(cache_context=True)
             async def func1(self, key: str, cache_context: _CacheContext) -> int:
@@ -504,6 +516,7 @@ class DescriptorTestCase(unittest.TestCase):
 
         class Cls:
             server_name = "test_server"
+            _, clock = get_clock()  # nb must be called this for @cached
 
             @cached()
             async def fn(self, arg1: int) -> str:
@@ -537,6 +550,7 @@ class DescriptorTestCase(unittest.TestCase):
         class Cls:
             inner_context_was_finished = False
             server_name = "test_server"  # nb must be called this for @cached
+            _, clock = get_clock()  # nb must be called this for @cached
 
             @cached()
             async def fn(self, arg1: int) -> str:
@@ -583,6 +597,7 @@ class CacheDecoratorTestCase(unittest.HomeserverTestCase):
     def test_passthrough(self) -> Generator["Deferred[Any]", object, None]:
         class A:
             server_name = "test_server"  # nb must be called this for @cached
+            _, clock = get_clock()  # nb must be called this for @cached
 
             @cached()
             def func(self, key: str) -> str:
@@ -599,6 +614,7 @@ class CacheDecoratorTestCase(unittest.HomeserverTestCase):
 
         class A:
             server_name = "test_server"  # nb must be called this for @cached
+            _, clock = get_clock()  # nb must be called this for @cached
 
             @cached()
             def func(self, key: str) -> str:
@@ -619,6 +635,7 @@ class CacheDecoratorTestCase(unittest.HomeserverTestCase):
 
         class A:
             server_name = "test_server"  # nb must be called this for @cached
+            _, clock = get_clock()  # nb must be called this for @cached
 
             @cached()
             def func(self, key: str) -> str:
@@ -639,6 +656,7 @@ class CacheDecoratorTestCase(unittest.HomeserverTestCase):
     def test_invalidate_missing(self) -> None:
         class A:
             server_name = "test_server"  # nb must be called this for @cached
+            _, clock = get_clock()  # nb must be called this for @cached
 
             @cached()
             def func(self, key: str) -> str:
@@ -652,6 +670,7 @@ class CacheDecoratorTestCase(unittest.HomeserverTestCase):
 
         class A:
             server_name = "test_server"  # nb must be called this for @cached
+            _, clock = get_clock()  # nb must be called this for @cached
 
             @cached(max_entries=10)
             def func(self, key: int) -> int:
@@ -681,6 +700,7 @@ class CacheDecoratorTestCase(unittest.HomeserverTestCase):
 
         class A:
             server_name = "test_server"  # nb must be called this for @cached
+            _, clock = get_clock()  # nb must be called this for @cached
 
             @cached()
             def func(self, key: str) -> "Deferred[int]":
@@ -701,6 +721,7 @@ class CacheDecoratorTestCase(unittest.HomeserverTestCase):
 
         class A:
             server_name = "test_server"  # nb must be called this for @cached
+            _, clock = get_clock()  # nb must be called this for @cached
 
             @cached()
             def func(self, key: str) -> str:
@@ -736,6 +757,7 @@ class CacheDecoratorTestCase(unittest.HomeserverTestCase):
 
         class A:
             server_name = "test_server"  # nb must be called this for @cached
+            _, clock = get_clock()  # nb must be called this for @cached
 
             @cached(max_entries=2)
             def func(self, key: str) -> str:
@@ -775,6 +797,7 @@ class CacheDecoratorTestCase(unittest.HomeserverTestCase):
 
         class A:
             server_name = "test_server"  # nb must be called this for @cached
+            _, clock = get_clock()  # nb must be called this for @cached
 
             @cached()
             def func(self, key: str) -> str:
@@ -824,6 +847,7 @@ class CachedListDescriptorTestCase(unittest.TestCase):
             def __init__(self) -> None:
                 self.mock = mock.Mock()
                 self.server_name = "test_server"
+                _, self.clock = get_clock()  # nb must be called this for @cached
 
             @descriptors.cached()
             def fn(self, arg1: int, arg2: int) -> None:
@@ -890,13 +914,14 @@ class CachedListDescriptorTestCase(unittest.TestCase):
             def __init__(self) -> None:
                 self.mock = mock.Mock()
                 self.server_name = "test_server"
+                _, self.clock = get_clock()  # nb must be called this for @cached
 
             @descriptors.cached()
             def fn(self, arg1: int) -> None:
                 pass
 
             @descriptors.cachedList(cached_method_name="fn", list_name="args1")
-            def list_fn(self, args1: List[int]) -> "Deferred[Mapping[int, str]]":
+            def list_fn(self, args1: list[int]) -> "Deferred[Mapping[int, str]]":
                 return self.mock(args1)
 
         obj = Cls()
@@ -934,13 +959,14 @@ class CachedListDescriptorTestCase(unittest.TestCase):
             def __init__(self) -> None:
                 self.mock = mock.Mock()
                 self.server_name = "test_server"
+                _, self.clock = get_clock()  # nb must be called this for @cached
 
             @descriptors.cached()
             def fn(self, arg1: int, arg2: int) -> None:
                 pass
 
             @descriptors.cachedList(cached_method_name="fn", list_name="args1")
-            async def list_fn(self, args1: List[int], arg2: int) -> Mapping[int, str]:
+            async def list_fn(self, args1: list[int], arg2: int) -> Mapping[int, str]:
                 # we want this to behave like an asynchronous function
                 await run_on_reactor()
                 return self.mock(args1, arg2)
@@ -975,13 +1001,14 @@ class CachedListDescriptorTestCase(unittest.TestCase):
 
         class Cls:
             server_name = "test_server"  # nb must be called this for @cached
+            _, clock = get_clock()  # nb must be called this for @cached
 
             @cached()
             def fn(self, arg1: int) -> None:
                 pass
 
             @cachedList(cached_method_name="fn", list_name="args")
-            async def list_fn(self, args: List[int]) -> Mapping[int, str]:
+            async def list_fn(self, args: list[int]) -> Mapping[int, str]:
                 await complete_lookup
                 return {arg: str(arg) for arg in args}
 
@@ -1011,13 +1038,14 @@ class CachedListDescriptorTestCase(unittest.TestCase):
         class Cls:
             inner_context_was_finished = False
             server_name = "test_server"  # nb must be called this for @cached
+            _, clock = get_clock()  # nb must be called this for @cached
 
             @cached()
             def fn(self, arg1: int) -> None:
                 pass
 
             @cachedList(cached_method_name="fn", list_name="args")
-            async def list_fn(self, args: List[int]) -> Mapping[int, str]:
+            async def list_fn(self, args: list[int]) -> Mapping[int, str]:
                 await make_deferred_yieldable(complete_lookup)
                 self.inner_context_was_finished = current_context().finished
                 return {arg: str(arg) for arg in args}
@@ -1055,6 +1083,7 @@ class CachedListDescriptorTestCase(unittest.TestCase):
 
         class Cls:
             server_name = "test_server"
+            _, clock = get_clock()  # nb must be called this for @cached
 
             @descriptors.cached(tree=True)
             def fn(self, room_id: str, event_id: str) -> None:
@@ -1064,7 +1093,7 @@ class CachedListDescriptorTestCase(unittest.TestCase):
             # of arguments as the underlying cached function, just with one of
             # the arguments being an iterable
             @descriptors.cachedList(cached_method_name="fn", list_name="keys")
-            def list_fn(self, keys: Iterable[Tuple[str, str]]) -> None:
+            def list_fn(self, keys: Iterable[tuple[str, str]]) -> None:
                 pass
 
             # Corrected syntax ✅
diff --git a/tests/util/test_async_helpers.py b/tests/util/test_async_helpers.py
index 54f7b55511..a6b7ddf485 100644
--- a/tests/util/test_async_helpers.py
+++ b/tests/util/test_async_helpers.py
@@ -19,13 +19,12 @@
 #
 import logging
 import traceback
-from typing import Any, Coroutine, List, NoReturn, Optional, Tuple, TypeVar
+from typing import Any, Coroutine, NoReturn, TypeVar
 
 from parameterized import parameterized_class
 
 from twisted.internet import defer
 from twisted.internet.defer import CancelledError, Deferred, ensureDeferred
-from twisted.internet.task import Clock
 from twisted.python.failure import Failure
 
 from synapse.logging.context import (
@@ -46,7 +45,7 @@ from synapse.util.async_helpers import (
 )
 
 from tests.server import get_clock
-from tests.unittest import TestCase
+from tests.unittest import TestCase, logcontext_clean
 
 logger = logging.getLogger(__name__)
 
@@ -72,7 +71,7 @@ class ObservableDeferredTest(TestCase):
         observer1.addBoth(check_called_first)
 
         # store the results
-        results: List[Optional[int]] = [None, None]
+        results: list[int | None] = [None, None]
 
         def check_val(res: int, idx: int) -> int:
             results[idx] = res
@@ -103,7 +102,7 @@ class ObservableDeferredTest(TestCase):
         observer1.addBoth(check_called_first)
 
         # store the results
-        results: List[Optional[Failure]] = [None, None]
+        results: list[Failure | None] = [None, None]
 
         def check_failure(res: Failure, idx: int) -> None:
             results[idx] = res
@@ -152,7 +151,7 @@ class ObservableDeferredTest(TestCase):
 
 class TimeoutDeferredTest(TestCase):
     def setUp(self) -> None:
-        self.clock = Clock()
+        self.reactor, self.clock = get_clock()
 
     def test_times_out(self) -> None:
         """Basic test case that checks that the original deferred is cancelled and that
@@ -165,12 +164,16 @@ class TimeoutDeferredTest(TestCase):
             cancelled = True
 
         non_completing_d: Deferred = Deferred(canceller)
-        timing_out_d = timeout_deferred(non_completing_d, 1.0, self.clock)
+        timing_out_d = timeout_deferred(
+            deferred=non_completing_d,
+            timeout=1.0,
+            clock=self.clock,
+        )
 
         self.assertNoResult(timing_out_d)
         self.assertFalse(cancelled, "deferred was cancelled prematurely")
 
-        self.clock.pump((1.0,))
+        self.reactor.pump((1.0,))
 
         self.assertTrue(cancelled, "deferred was not cancelled by timeout")
         self.failureResultOf(timing_out_d, defer.TimeoutError)
@@ -183,15 +186,24 @@ class TimeoutDeferredTest(TestCase):
             raise Exception("can't cancel this deferred")
 
         non_completing_d: Deferred = Deferred(canceller)
-        timing_out_d = timeout_deferred(non_completing_d, 1.0, self.clock)
+        timing_out_d = timeout_deferred(
+            deferred=non_completing_d,
+            timeout=1.0,
+            clock=self.clock,
+        )
 
         self.assertNoResult(timing_out_d)
 
-        self.clock.pump((1.0,))
+        self.reactor.pump((1.0,))
 
         self.failureResultOf(timing_out_d, defer.TimeoutError)
 
-    async def test_logcontext_is_preserved_on_cancellation(self) -> None:
+    @logcontext_clean
+    async def test_logcontext_is_preserved_on_timeout_cancellation(self) -> None:
+        """
+        Test that the logcontext is preserved when we timeout and the deferred is
+        cancelled.
+        """
         # Sanity check that we start in the sentinel context
         self.assertEqual(current_context(), SENTINEL_CONTEXT)
 
@@ -227,7 +239,7 @@ class TimeoutDeferredTest(TestCase):
             timing_out_d = timeout_deferred(
                 deferred=incomplete_d,
                 timeout=1.0,
-                reactor=self.clock,
+                clock=self.clock,
             )
             self.assertNoResult(timing_out_d)
             # We should still be in the logcontext we started in
@@ -243,7 +255,7 @@ class TimeoutDeferredTest(TestCase):
             # we're pumping the reactor in the block and return us back to our current
             # logcontext after the block.
             with PreserveLoggingContext():
-                self.clock.pump(
+                self.reactor.pump(
                     # We only need to pump `1.0` (seconds) as we set
                     # `timeout_deferred(timeout=1.0)` above
                     (1.0,)
@@ -263,8 +275,67 @@ class TimeoutDeferredTest(TestCase):
         # Back to the sentinel context
         self.assertEqual(current_context(), SENTINEL_CONTEXT)
 
+    @logcontext_clean
+    async def test_logcontext_is_not_lost_when_awaiting_on_timeout_cancellation(
+        self,
+    ) -> None:
+        """
+        Test that the logcontext isn't lost when we `await make_deferred_yieldable(...)`
+        the deferred to complete/timeout and it times out.
+        """
 
-class _TestException(Exception):
+        # Sanity check that we start in the sentinel context
+        self.assertEqual(current_context(), SENTINEL_CONTEXT)
+
+        # Create a deferred which we will never complete
+        incomplete_d: Deferred = Deferred()
+
+        async def competing_task() -> None:
+            with LoggingContext(
+                name="competing", server_name="test_server"
+            ) as context_competing:
+                timing_out_d = timeout_deferred(
+                    deferred=incomplete_d,
+                    timeout=1.0,
+                    clock=self.clock,
+                )
+                self.assertNoResult(timing_out_d)
+                # We should still be in the logcontext we started in
+                self.assertIs(current_context(), context_competing)
+
+                # Mimic the normal use case to wait for the work to complete or timeout.
+                #
+                # In this specific test, we expect the deferred to timeout and raise an
+                # exception at this point.
+                await make_deferred_yieldable(timing_out_d)
+
+                self.fail(
+                    "We should not make it to this point as the `timing_out_d` should have been cancelled"
+                )
+
+        d = defer.ensureDeferred(competing_task())
+
+        # Still in the sentinel context
+        self.assertEqual(current_context(), SENTINEL_CONTEXT)
+
+        # Pump until we trigger the timeout
+        self.reactor.pump(
+            # We only need to pump `1.0` (seconds) as we set
+            # `timeout_deferred(timeout=1.0)` above
+            (1.0,)
+        )
+
+        # Still in the sentinel context
+        self.assertEqual(current_context(), SENTINEL_CONTEXT)
+
+        # We expect a failure due to the timeout
+        self.failureResultOf(d, defer.TimeoutError)
+
+        # Back to the sentinel context at the end of the day
+        self.assertEqual(current_context(), SENTINEL_CONTEXT)
+
+
+class _TestException(Exception):  #
     pass
 
 
@@ -560,8 +631,8 @@ class AwakenableSleeperTests(TestCase):
     "Tests AwakenableSleeper"
 
     def test_sleep(self) -> None:
-        reactor, _ = get_clock()
-        sleeper = AwakenableSleeper(reactor)
+        reactor, clock = get_clock()
+        sleeper = AwakenableSleeper(clock)
 
         d = defer.ensureDeferred(sleeper.sleep("name", 1000))
 
@@ -575,8 +646,8 @@ class AwakenableSleeperTests(TestCase):
         self.assertTrue(d.called)
 
     def test_explicit_wake(self) -> None:
-        reactor, _ = get_clock()
-        sleeper = AwakenableSleeper(reactor)
+        reactor, clock = get_clock()
+        sleeper = AwakenableSleeper(clock)
 
         d = defer.ensureDeferred(sleeper.sleep("name", 1000))
 
@@ -592,8 +663,8 @@ class AwakenableSleeperTests(TestCase):
         reactor.advance(0.6)
 
     def test_multiple_sleepers_timeout(self) -> None:
-        reactor, _ = get_clock()
-        sleeper = AwakenableSleeper(reactor)
+        reactor, clock = get_clock()
+        sleeper = AwakenableSleeper(clock)
 
         d1 = defer.ensureDeferred(sleeper.sleep("name", 1000))
 
@@ -612,8 +683,8 @@ class AwakenableSleeperTests(TestCase):
         self.assertTrue(d2.called)
 
     def test_multiple_sleepers_wake(self) -> None:
-        reactor, _ = get_clock()
-        sleeper = AwakenableSleeper(reactor)
+        reactor, clock = get_clock()
+        sleeper = AwakenableSleeper(clock)
 
         d1 = defer.ensureDeferred(sleeper.sleep("name", 1000))
 
@@ -637,7 +708,7 @@ class AwakenableSleeperTests(TestCase):
 class GatherCoroutineTests(TestCase):
     """Tests for `gather_optional_coroutines`"""
 
-    def make_coroutine(self) -> Tuple[Coroutine[Any, Any, T], "defer.Deferred[T]"]:
+    def make_coroutine(self) -> tuple[Coroutine[Any, Any, T], "defer.Deferred[T]"]:
         """Returns a coroutine and a deferred that it is waiting on to resolve"""
 
         d: "defer.Deferred[T]" = defer.Deferred()
diff --git a/tests/util/test_background_queue.py b/tests/util/test_background_queue.py
new file mode 100644
index 0000000000..901b014845
--- /dev/null
+++ b/tests/util/test_background_queue.py
@@ -0,0 +1,117 @@
+#
+# This file is licensed under the Affero General Public License (AGPL) version 3.
+#
+# Copyright (C) 2025 Element Creations Ltd
+#
+# This program is free software: you can redistribute it and/or modify
+# it under the terms of the GNU Affero General Public License as
+# published by the Free Software Foundation, either version 3 of the
+# License, or (at your option) any later version.
+#
+# See the GNU Affero General Public License for more details:
+# <https://www.gnu.org/licenses/agpl-3.0.html>.
+#
+
+
+from unittest.mock import Mock
+
+from twisted.internet.defer import Deferred
+from twisted.internet.testing import MemoryReactor
+
+from synapse.logging.context import PreserveLoggingContext, make_deferred_yieldable
+from synapse.server import HomeServer
+from synapse.util.background_queue import BackgroundQueue
+from synapse.util.clock import Clock
+
+from tests.unittest import HomeserverTestCase, logcontext_clean
+
+
+class BackgroundQueueTests(HomeserverTestCase):
+    def prepare(
+        self, reactor: MemoryReactor, clock: Clock, homeserver: HomeServer
+    ) -> None:
+        self._process_item_mock = Mock(spec_set=[])
+
+        self.queue = BackgroundQueue[int](
+            hs=homeserver,
+            name="test_queue",
+            callback=self._process_item_mock,
+            timeout_ms=1000,
+        )
+
+    @logcontext_clean
+    def test_simple_call(self) -> None:
+        """Test that items added to the queue are processed."""
+        # Register a deferred to be the return value of the callback.
+        callback_result_deferred: Deferred[None] = Deferred()
+        self._process_item_mock.side_effect = lambda _: make_deferred_yieldable(
+            callback_result_deferred
+        )
+
+        # Adding an item should cause the callback to be invoked.
+        self.queue.add(1)
+
+        self._process_item_mock.assert_called_once_with(1)
+        self._process_item_mock.reset_mock()
+
+        # Adding another item should not cause the callback to be invoked again
+        # until the previous one has completed.
+        self.queue.add(2)
+        self._process_item_mock.assert_not_called()
+
+        # Once the first callback completes, the second item should be
+        # processed.
+        with PreserveLoggingContext():
+            callback_result_deferred.callback(None)
+        self._process_item_mock.assert_called_once_with(2)
+
+    @logcontext_clean
+    def test_timeout(self) -> None:
+        """Test that the background process wakes up if its idle, and that it
+        times out after being idle."""
+
+        # Register a deferred to be the return value of the callback.
+        callback_result_deferred: Deferred[None] = Deferred()
+        self._process_item_mock.side_effect = lambda _: make_deferred_yieldable(
+            callback_result_deferred
+        )
+
+        # Adding an item should cause the callback to be invoked.
+        self.queue.add(1)
+
+        self._process_item_mock.assert_called_once_with(1)
+        self._process_item_mock.reset_mock()
+
+        # Let the callback complete.
+        with PreserveLoggingContext():
+            callback_result_deferred.callback(None)
+
+        # Advance the clock by less than the timeout, and add another item.
+        self.reactor.advance(0.5)
+        self.assertIsNotNone(self.queue._wakeup_event)
+        self.queue.add(2)
+
+        # The callback should be invoked again.
+        callback_result_deferred = Deferred()
+        self._process_item_mock.side_effect = lambda _: make_deferred_yieldable(
+            callback_result_deferred
+        )
+        self._process_item_mock.assert_called_once_with(2)
+        self._process_item_mock.reset_mock()
+
+        # Let the callback complete.
+        with PreserveLoggingContext():
+            callback_result_deferred.callback(None)
+
+        # Advance the clock by more than the timeout.
+        self.reactor.advance(1.5)
+
+        # The background process should have exited, we check this by checking
+        # the internal wakeup event has been removed.
+        self.assertIsNone(self.queue._wakeup_event)
+
+        # Add another item. This should cause a new background process to be
+        # started.
+        self.queue.add(3)
+
+        self._process_item_mock.assert_called_once_with(3)
diff --git a/tests/util/test_batching_queue.py b/tests/util/test_batching_queue.py
index 532582cf87..30b07dc6ad 100644
--- a/tests/util/test_batching_queue.py
+++ b/tests/util/test_batching_queue.py
@@ -18,7 +18,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import List, Tuple
 
 from prometheus_client import Gauge
 
@@ -32,13 +31,12 @@ from synapse.util.batching_queue import (
     number_queued,
 )
 
-from tests.server import get_clock
-from tests.unittest import TestCase
+from tests.unittest import HomeserverTestCase
 
 
-class BatchingQueueTestCase(TestCase):
+class BatchingQueueTestCase(HomeserverTestCase):
     def setUp(self) -> None:
-        self.clock, hs_clock = get_clock()
+        super().setUp()
 
         # We ensure that we remove any existing metrics for "test_queue".
         try:
@@ -48,15 +46,15 @@ class BatchingQueueTestCase(TestCase):
         except KeyError:
             pass
 
-        self._pending_calls: List[Tuple[List[str], defer.Deferred]] = []
+        self._pending_calls: list[tuple[list[str], defer.Deferred]] = []
         self.queue: BatchingQueue[str, str] = BatchingQueue(
             name="test_queue",
-            server_name="test_server",
-            clock=hs_clock,
+            hs=self.hs,
+            clock=self.clock,
             process_batch_callback=self._process_queue,
         )
 
-    async def _process_queue(self, values: List[str]) -> str:
+    async def _process_queue(self, values: list[str]) -> str:
         d: "defer.Deferred[str]" = defer.Deferred()
         self._pending_calls.append((values, d))
         return await make_deferred_yieldable(d)
@@ -108,7 +106,7 @@ class BatchingQueueTestCase(TestCase):
         self.assertFalse(queue_d.called)
 
         # We should see a call to `_process_queue` after a reactor tick.
-        self.clock.pump([0])
+        self.reactor.pump([0])
 
         self.assertEqual(len(self._pending_calls), 1)
         self.assertEqual(self._pending_calls[0][0], ["foo"])
@@ -134,7 +132,7 @@ class BatchingQueueTestCase(TestCase):
 
         self._assert_metrics(queued=2, keys=1, in_flight=2)
 
-        self.clock.pump([0])
+        self.reactor.pump([0])
 
         # We should see only *one* call to `_process_queue`
         self.assertEqual(len(self._pending_calls), 1)
@@ -158,7 +156,7 @@ class BatchingQueueTestCase(TestCase):
         self.assertFalse(self._pending_calls)
 
         queue_d1 = defer.ensureDeferred(self.queue.add_to_queue("foo1"))
-        self.clock.pump([0])
+        self.reactor.pump([0])
 
         self.assertEqual(len(self._pending_calls), 1)
 
@@ -185,7 +183,7 @@ class BatchingQueueTestCase(TestCase):
         self._assert_metrics(queued=2, keys=1, in_flight=2)
 
         # We should now see a second call to `_process_queue`
-        self.clock.pump([0])
+        self.reactor.pump([0])
         self.assertEqual(len(self._pending_calls), 1)
         self.assertEqual(self._pending_calls[0][0], ["foo2", "foo3"])
         self.assertFalse(queue_d2.called)
@@ -206,9 +204,9 @@ class BatchingQueueTestCase(TestCase):
         self.assertFalse(self._pending_calls)
 
         queue_d1 = defer.ensureDeferred(self.queue.add_to_queue("foo1", key=1))
-        self.clock.pump([0])
+        self.reactor.pump([0])
         queue_d2 = defer.ensureDeferred(self.queue.add_to_queue("foo2", key=2))
-        self.clock.pump([0])
+        self.reactor.pump([0])
 
         # We queue up another item with key=2 to check that we will keep taking
         # things off the queue.
@@ -240,7 +238,7 @@ class BatchingQueueTestCase(TestCase):
         self.assertFalse(queue_d3.called)
 
         # We should now see a call `_pending_calls` for `foo3`
-        self.clock.pump([0])
+        self.reactor.pump([0])
         self.assertEqual(len(self._pending_calls), 1)
         self.assertEqual(self._pending_calls[0][0], ["foo3"])
         self.assertFalse(queue_d3.called)
diff --git a/tests/util/test_check_dependencies.py b/tests/util/test_check_dependencies.py
index c052ba2b75..b7a23dcd9d 100644
--- a/tests/util/test_check_dependencies.py
+++ b/tests/util/test_check_dependencies.py
@@ -22,9 +22,11 @@
 from contextlib import contextmanager
 from os import PathLike
 from pathlib import Path
-from typing import Generator, Optional, Union
+from typing import Generator, cast
 from unittest.mock import patch
 
+from packaging.markers import default_environment as packaging_default_environment
+
 from synapse.util.check_dependencies import (
     DependencyException,
     check_requirements,
@@ -42,7 +44,7 @@ class DummyDistribution(metadata.Distribution):
     def version(self) -> str:
         return self._version
 
-    def locate_file(self, path: Union[str, PathLike]) -> Path:
+    def locate_file(self, path: str | PathLike) -> Path:
         raise NotImplementedError()
 
     def read_text(self, filename: str) -> None:
@@ -61,7 +63,7 @@ distribution_with_no_version = DummyDistribution(None)  # type: ignore[arg-type]
 class TestDependencyChecker(TestCase):
     @contextmanager
     def mock_installed_package(
-        self, distribution: Optional[DummyDistribution]
+        self, distribution: DummyDistribution | None
     ) -> Generator[None, None, None]:
         """Pretend that looking up any package yields the given `distribution`.
 
@@ -80,6 +82,22 @@ class TestDependencyChecker(TestCase):
         ):
             yield
 
+    @contextmanager
+    def mock_python_version(self, version: str) -> Generator[None, None, None]:
+        """Override the marker environment to report the supplied `python_version`."""
+
+        def fake_default_environment() -> dict[str, str]:
+            env = cast(dict[str, str], dict(packaging_default_environment()))
+            env["python_version"] = version
+            env["python_full_version"] = f"{version}.0"
+            return env
+
+        with patch(
+            "synapse.util.check_dependencies.default_environment",
+            side_effect=fake_default_environment,
+        ):
+            yield
+
     def test_mandatory_dependency(self) -> None:
         """Complain if a required package is missing or old."""
         with patch(
@@ -191,3 +209,35 @@ class TestDependencyChecker(TestCase):
             with self.mock_installed_package(old):
                 # We also ignore old versions of setuptools_rust
                 check_requirements()
+
+    def test_python_version_markers_respected(self) -> None:
+        """
+        Tests that python_version markers are properly respected.
+
+        Specifically that older versions of dependencies can be installed in
+        environments with older Python versions.
+        """
+        requirements = [
+            "pydantic ~= 2.8; python_version < '3.14'",
+            "pydantic ~= 2.12; python_version >= '3.14'",
+        ]
+
+        with patch(
+            "synapse.util.check_dependencies.metadata.requires",
+            return_value=requirements,
+        ):
+            with self.mock_python_version("3.9"):
+                with self.mock_installed_package(DummyDistribution("2.12.3")):
+                    check_requirements()
+                with self.mock_installed_package(DummyDistribution("2.8.1")):
+                    check_requirements()
+                with self.mock_installed_package(DummyDistribution("2.7.0")):
+                    self.assertRaises(DependencyException, check_requirements)
+
+            with self.mock_python_version("3.14"):
+                with self.mock_installed_package(DummyDistribution("2.12.3")):
+                    check_requirements()
+                with self.mock_installed_package(DummyDistribution("2.8.1")):
+                    self.assertRaises(DependencyException, check_requirements)
+                with self.mock_installed_package(DummyDistribution("2.7.0")):
+                    self.assertRaises(DependencyException, check_requirements)
diff --git a/tests/util/test_dict_cache.py b/tests/util/test_dict_cache.py
index 246e18fd15..16e096a4b2 100644
--- a/tests/util/test_dict_cache.py
+++ b/tests/util/test_dict_cache.py
@@ -23,12 +23,14 @@
 from synapse.util.caches.dictionary_cache import DictionaryCache
 
 from tests import unittest
+from tests.server import get_clock
 
 
 class DictCacheTestCase(unittest.TestCase):
     def setUp(self) -> None:
+        _, clock = get_clock()
         self.cache: DictionaryCache[str, str, str] = DictionaryCache(
-            name="foobar", server_name="test_server", max_entries=10
+            name="foobar", clock=clock, server_name="test_server", max_entries=10
         )
 
     def test_simple_cache_hit_full(self) -> None:
diff --git a/tests/util/test_expiring_cache.py b/tests/util/test_expiring_cache.py
index bfcc6cd12f..8964359a6e 100644
--- a/tests/util/test_expiring_cache.py
+++ b/tests/util/test_expiring_cache.py
@@ -19,23 +19,22 @@
 #
 #
 
-from typing import List, cast
 
 from synapse.util.caches.expiringcache import ExpiringCache
-from synapse.util.clock import Clock
 
-from tests.utils import MockClock
+from tests.server import get_clock
 
 from .. import unittest
 
 
 class ExpiringCacheTestCase(unittest.HomeserverTestCase):
     def test_get_set(self) -> None:
-        clock = MockClock()
+        reactor, clock = get_clock()
         cache: ExpiringCache[str, str] = ExpiringCache(
             cache_name="test",
             server_name="testserver",
-            clock=cast(Clock, clock),
+            hs=self.hs,
+            clock=clock,
             max_len=1,
         )
 
@@ -44,11 +43,12 @@ class ExpiringCacheTestCase(unittest.HomeserverTestCase):
         self.assertEqual(cache["key"], "value")
 
     def test_eviction(self) -> None:
-        clock = MockClock()
+        reactor, clock = get_clock()
         cache: ExpiringCache[str, str] = ExpiringCache(
             cache_name="test",
             server_name="testserver",
-            clock=cast(Clock, clock),
+            hs=self.hs,
+            clock=clock,
             max_len=2,
         )
 
@@ -63,11 +63,12 @@ class ExpiringCacheTestCase(unittest.HomeserverTestCase):
         self.assertEqual(cache.get("key3"), "value3")
 
     def test_iterable_eviction(self) -> None:
-        clock = MockClock()
-        cache: ExpiringCache[str, List[int]] = ExpiringCache(
+        reactor, clock = get_clock()
+        cache: ExpiringCache[str, list[int]] = ExpiringCache(
             cache_name="test",
             server_name="testserver",
-            clock=cast(Clock, clock),
+            hs=self.hs,
+            clock=clock,
             max_len=5,
             iterable=True,
         )
@@ -87,25 +88,26 @@ class ExpiringCacheTestCase(unittest.HomeserverTestCase):
         self.assertEqual(cache.get("key4"), [6, 7])
 
     def test_time_eviction(self) -> None:
-        clock = MockClock()
+        reactor, clock = get_clock()
         cache: ExpiringCache[str, int] = ExpiringCache(
             cache_name="test",
             server_name="testserver",
-            clock=cast(Clock, clock),
+            hs=self.hs,
+            clock=clock,
             expiry_ms=1000,
         )
 
         cache["key"] = 1
-        clock.advance_time(0.5)
+        reactor.advance(0.5)
         cache["key2"] = 2
 
         self.assertEqual(cache.get("key"), 1)
         self.assertEqual(cache.get("key2"), 2)
 
-        clock.advance_time(0.9)
+        reactor.advance(0.9)
         self.assertEqual(cache.get("key"), None)
         self.assertEqual(cache.get("key2"), 2)
 
-        clock.advance_time(1)
+        reactor.advance(1)
         self.assertEqual(cache.get("key"), None)
         self.assertEqual(cache.get("key2"), None)
diff --git a/tests/util/test_file_consumer.py b/tests/util/test_file_consumer.py
index ab0143e605..e6d54ddb8d 100644
--- a/tests/util/test_file_consumer.py
+++ b/tests/util/test_file_consumer.py
@@ -20,7 +20,7 @@
 
 import threading
 from io import BytesIO
-from typing import BinaryIO, Generator, Optional, cast
+from typing import BinaryIO, Generator, cast
 from unittest.mock import NonCallableMock
 
 from zope.interface import implementer
@@ -127,7 +127,7 @@ class FileConsumerTests(unittest.TestCase):
 @implementer(IPullProducer)
 class DummyPullProducer:
     def __init__(self) -> None:
-        self.consumer: Optional[BackgroundFileConsumer] = None
+        self.consumer: BackgroundFileConsumer | None = None
         self.deferred: "defer.Deferred[object]" = defer.Deferred()
 
     def resumeProducing(self) -> None:
@@ -159,7 +159,7 @@ class BlockingBytesWrite:
         self.closed = False
         self.write_lock = threading.Lock()
 
-        self._notify_write_deferred: Optional[defer.Deferred] = None
+        self._notify_write_deferred: defer.Deferred | None = None
         self._number_of_writes = 0
 
     def write(self, write_bytes: bytes) -> None:
diff --git a/tests/util/test_itertools.py b/tests/util/test_itertools.py
index 7a593cc683..016389d49b 100644
--- a/tests/util/test_itertools.py
+++ b/tests/util/test_itertools.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Dict, Iterable, List, Sequence
+from typing import Iterable, Sequence
 
 from synapse.util.iterutils import (
     chunk_seq,
@@ -67,13 +67,13 @@ class SortTopologically(TestCase):
     def test_empty(self) -> None:
         "Test that an empty graph works correctly"
 
-        graph: Dict[int, List[int]] = {}
+        graph: dict[int, list[int]] = {}
         self.assertEqual(list(sorted_topologically([], graph)), [])
 
     def test_handle_empty_graph(self) -> None:
         "Test that a graph where a node doesn't have an entry is treated as empty"
 
-        graph: Dict[int, List[int]] = {}
+        graph: dict[int, list[int]] = {}
 
         # For disconnected nodes the output is simply sorted.
         self.assertEqual(list(sorted_topologically([1, 2], graph)), [1, 2])
@@ -81,7 +81,7 @@ class SortTopologically(TestCase):
     def test_disconnected(self) -> None:
         "Test that a graph with no edges work"
 
-        graph: Dict[int, List[int]] = {1: [], 2: []}
+        graph: dict[int, list[int]] = {1: [], 2: []}
 
         # For disconnected nodes the output is simply sorted.
         self.assertEqual(list(sorted_topologically([1, 2], graph)), [1, 2])
@@ -89,19 +89,19 @@ class SortTopologically(TestCase):
     def test_linear(self) -> None:
         "Test that a simple `4 -> 3 -> 2 -> 1` graph works"
 
-        graph: Dict[int, List[int]] = {1: [], 2: [1], 3: [2], 4: [3]}
+        graph: dict[int, list[int]] = {1: [], 2: [1], 3: [2], 4: [3]}
 
         self.assertEqual(list(sorted_topologically([4, 3, 2, 1], graph)), [1, 2, 3, 4])
 
     def test_subset(self) -> None:
         "Test that only sorting a subset of the graph works"
-        graph: Dict[int, List[int]] = {1: [], 2: [1], 3: [2], 4: [3]}
+        graph: dict[int, list[int]] = {1: [], 2: [1], 3: [2], 4: [3]}
 
         self.assertEqual(list(sorted_topologically([4, 3], graph)), [3, 4])
 
     def test_fork(self) -> None:
         "Test that a forked graph works"
-        graph: Dict[int, List[int]] = {1: [], 2: [1], 3: [1], 4: [2, 3]}
+        graph: dict[int, list[int]] = {1: [], 2: [1], 3: [1], 4: [2, 3]}
 
         # Valid orderings are `[1, 3, 2, 4]` or `[1, 2, 3, 4]`, but we should
         # always get the same one.
@@ -109,13 +109,13 @@ class SortTopologically(TestCase):
 
     def test_duplicates(self) -> None:
         "Test that a graph with duplicate edges work"
-        graph: Dict[int, List[int]] = {1: [], 2: [1, 1], 3: [2, 2], 4: [3]}
+        graph: dict[int, list[int]] = {1: [], 2: [1, 1], 3: [2, 2], 4: [3]}
 
         self.assertEqual(list(sorted_topologically([4, 3, 2, 1], graph)), [1, 2, 3, 4])
 
     def test_multiple_paths(self) -> None:
         "Test that a graph with multiple paths between two nodes work"
-        graph: Dict[int, List[int]] = {1: [], 2: [1], 3: [2], 4: [3, 2, 1]}
+        graph: dict[int, list[int]] = {1: [], 2: [1], 3: [2], 4: [3, 2, 1]}
 
         self.assertEqual(list(sorted_topologically([4, 3, 2, 1], graph)), [1, 2, 3, 4])
 
@@ -126,13 +126,13 @@ class SortTopologicallyBatched(TestCase):
     def test_empty(self) -> None:
         "Test that an empty graph works correctly"
 
-        graph: Dict[int, List[int]] = {}
+        graph: dict[int, list[int]] = {}
         self.assertEqual(list(sorted_topologically_batched([], graph)), [])
 
     def test_handle_empty_graph(self) -> None:
         "Test that a graph where a node doesn't have an entry is treated as empty"
 
-        graph: Dict[int, List[int]] = {}
+        graph: dict[int, list[int]] = {}
 
         # For disconnected nodes the output is simply sorted.
         self.assertEqual(list(sorted_topologically_batched([1, 2], graph)), [[1, 2]])
@@ -140,7 +140,7 @@ class SortTopologicallyBatched(TestCase):
     def test_disconnected(self) -> None:
         "Test that a graph with no edges work"
 
-        graph: Dict[int, List[int]] = {1: [], 2: []}
+        graph: dict[int, list[int]] = {1: [], 2: []}
 
         # For disconnected nodes the output is simply sorted.
         self.assertEqual(list(sorted_topologically_batched([1, 2], graph)), [[1, 2]])
@@ -148,7 +148,7 @@ class SortTopologicallyBatched(TestCase):
     def test_linear(self) -> None:
         "Test that a simple `4 -> 3 -> 2 -> 1` graph works"
 
-        graph: Dict[int, List[int]] = {1: [], 2: [1], 3: [2], 4: [3]}
+        graph: dict[int, list[int]] = {1: [], 2: [1], 3: [2], 4: [3]}
 
         self.assertEqual(
             list(sorted_topologically_batched([4, 3, 2, 1], graph)),
@@ -157,13 +157,13 @@ class SortTopologicallyBatched(TestCase):
 
     def test_subset(self) -> None:
         "Test that only sorting a subset of the graph works"
-        graph: Dict[int, List[int]] = {1: [], 2: [1], 3: [2], 4: [3]}
+        graph: dict[int, list[int]] = {1: [], 2: [1], 3: [2], 4: [3]}
 
         self.assertEqual(list(sorted_topologically_batched([4, 3], graph)), [[3], [4]])
 
     def test_fork(self) -> None:
         "Test that a forked graph works"
-        graph: Dict[int, List[int]] = {1: [], 2: [1], 3: [1], 4: [2, 3]}
+        graph: dict[int, list[int]] = {1: [], 2: [1], 3: [1], 4: [2, 3]}
 
         # Valid orderings are `[1, 3, 2, 4]` or `[1, 2, 3, 4]`, but we should
         # always get the same one.
@@ -173,7 +173,7 @@ class SortTopologicallyBatched(TestCase):
 
     def test_duplicates(self) -> None:
         "Test that a graph with duplicate edges work"
-        graph: Dict[int, List[int]] = {1: [], 2: [1, 1], 3: [2, 2], 4: [3]}
+        graph: dict[int, list[int]] = {1: [], 2: [1, 1], 3: [2, 2], 4: [3]}
 
         self.assertEqual(
             list(sorted_topologically_batched([4, 3, 2, 1], graph)),
@@ -182,7 +182,7 @@ class SortTopologicallyBatched(TestCase):
 
     def test_multiple_paths(self) -> None:
         "Test that a graph with multiple paths between two nodes work"
-        graph: Dict[int, List[int]] = {1: [], 2: [1], 3: [2], 4: [3, 2, 1]}
+        graph: dict[int, list[int]] = {1: [], 2: [1], 3: [2], 4: [3, 2, 1]}
 
         self.assertEqual(
             list(sorted_topologically_batched([4, 3, 2, 1], graph)),
diff --git a/tests/util/test_linearizer.py b/tests/util/test_linearizer.py
index 722ce79dcc..b2a631d747 100644
--- a/tests/util/test_linearizer.py
+++ b/tests/util/test_linearizer.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import Hashable, Protocol, Tuple
+from typing import Hashable, Protocol
 
 from twisted.internet import defer
 from twisted.internet.defer import CancelledError, Deferred
@@ -43,7 +43,7 @@ class LinearizerTestCase(unittest.TestCase):
 
     def _start_task(
         self, linearizer: Linearizer, key: Hashable
-    ) -> Tuple["Deferred[None]", "Deferred[None]", UnblockFunction]:
+    ) -> tuple["Deferred[None]", "Deferred[None]", UnblockFunction]:
         """Starts a task which acquires the linearizer lock, blocks, then completes.
 
         Args:
diff --git a/tests/util/test_logcontext.py b/tests/util/test_logcontext.py
index 966ea31f1a..ca805bb20a 100644
--- a/tests/util/test_logcontext.py
+++ b/tests/util/test_logcontext.py
@@ -66,7 +66,8 @@ class LoggingContextTestCase(unittest.TestCase):
         """
         Test `Clock.sleep`
         """
-        clock = Clock(reactor, server_name="test_server")
+        # Ignore linter error since we are creating a `Clock` for testing purposes.
+        clock = Clock(reactor, server_name="test_server")  # type: ignore[multiple-internal-clocks]
 
         # Sanity check that we start in the sentinel context
         self._check_test_key("sentinel")
@@ -90,7 +91,7 @@ class LoggingContextTestCase(unittest.TestCase):
                 # so that the test can complete and we see the underlying error.
                 callback_finished = True
 
-        reactor.callLater(0, lambda: defer.ensureDeferred(competing_callback()))
+        reactor.callLater(0, lambda: defer.ensureDeferred(competing_callback()))  # type: ignore[call-later-not-tracked]
 
         with LoggingContext(name="foo", server_name="test_server"):
             await clock.sleep(0)
@@ -111,7 +112,8 @@ class LoggingContextTestCase(unittest.TestCase):
         """
         Test `Clock.looping_call`
         """
-        clock = Clock(reactor, server_name="test_server")
+        # Ignore linter error since we are creating a `Clock` for testing purposes.
+        clock = Clock(reactor, server_name="test_server")  # type: ignore[multiple-internal-clocks]
 
         # Sanity check that we start in the sentinel context
         self._check_test_key("sentinel")
@@ -161,7 +163,8 @@ class LoggingContextTestCase(unittest.TestCase):
         """
         Test `Clock.looping_call_now`
         """
-        clock = Clock(reactor, server_name="test_server")
+        # Ignore linter error since we are creating a `Clock` for testing purposes.
+        clock = Clock(reactor, server_name="test_server")  # type: ignore[multiple-internal-clocks]
 
         # Sanity check that we start in the sentinel context
         self._check_test_key("sentinel")
@@ -209,7 +212,8 @@ class LoggingContextTestCase(unittest.TestCase):
         """
         Test `Clock.call_later`
         """
-        clock = Clock(reactor, server_name="test_server")
+        # Ignore linter error since we are creating a `Clock` for testing purposes.
+        clock = Clock(reactor, server_name="test_server")  # type: ignore[multiple-internal-clocks]
 
         # Sanity check that we start in the sentinel context
         self._check_test_key("sentinel")
@@ -261,7 +265,8 @@ class LoggingContextTestCase(unittest.TestCase):
         `d.callback(None)` without anything else. See the *Deferred callbacks* section
         of docs/log_contexts.md for more details.
         """
-        clock = Clock(reactor, server_name="test_server")
+        # Ignore linter error since we are creating a `Clock` for testing purposes.
+        clock = Clock(reactor, server_name="test_server")  # type: ignore[multiple-internal-clocks]
 
         # Sanity check that we start in the sentinel context
         self._check_test_key("sentinel")
@@ -318,7 +323,8 @@ class LoggingContextTestCase(unittest.TestCase):
         `d.callback(None)` without anything else. See the *Deferred callbacks* section
         of docs/log_contexts.md for more details.
         """
-        clock = Clock(reactor, server_name="test_server")
+        # Ignore linter error since we are creating a `Clock` for testing purposes.
+        clock = Clock(reactor, server_name="test_server")  # type: ignore[multiple-internal-clocks]
 
         # Sanity check that we start in the sentinel context
         self._check_test_key("sentinel")
@@ -379,7 +385,8 @@ class LoggingContextTestCase(unittest.TestCase):
         `d.callback(None)` without anything else. See the *Deferred callbacks* section
         of docs/log_contexts.md for more details.
         """
-        clock = Clock(reactor, server_name="test_server")
+        # Ignore linter error since we are creating a `Clock` for testing purposes.
+        clock = Clock(reactor, server_name="test_server")  # type: ignore[multiple-internal-clocks]
 
         # Sanity check that we start in the sentinel context
         self._check_test_key("sentinel")
@@ -450,7 +457,8 @@ class LoggingContextTestCase(unittest.TestCase):
         self._check_test_key("sentinel")
 
     async def _test_run_in_background(self, function: Callable[[], object]) -> None:
-        clock = Clock(reactor, server_name="test_server")
+        # Ignore linter error since we are creating a `Clock` for testing purposes.
+        clock = Clock(reactor, server_name="test_server")  # type: ignore[multiple-internal-clocks]
 
         # Sanity check that we start in the sentinel context
         self._check_test_key("sentinel")
@@ -492,7 +500,8 @@ class LoggingContextTestCase(unittest.TestCase):
     @logcontext_clean
     async def test_run_in_background_with_blocking_fn(self) -> None:
         async def blocking_function() -> None:
-            await Clock(reactor, server_name="test_server").sleep(0)
+            # Ignore linter error since we are creating a `Clock` for testing purposes.
+            await Clock(reactor, server_name="test_server").sleep(0)  # type: ignore[multiple-internal-clocks]
 
         await self._test_run_in_background(blocking_function)
 
@@ -525,7 +534,8 @@ class LoggingContextTestCase(unittest.TestCase):
 
         async def testfunc() -> None:
             self._check_test_key("foo")
-            d = defer.ensureDeferred(Clock(reactor, server_name="test_server").sleep(0))
+            # Ignore linter error since we are creating a `Clock` for testing purposes.
+            d = defer.ensureDeferred(Clock(reactor, server_name="test_server").sleep(0))  # type: ignore[multiple-internal-clocks]
             self.assertIs(current_context(), SENTINEL_CONTEXT)
             await d
             self._check_test_key("foo")
@@ -554,7 +564,8 @@ class LoggingContextTestCase(unittest.TestCase):
 
         This will stress the logic around incomplete deferreds in `run_coroutine_in_background`.
         """
-        clock = Clock(reactor, server_name="test_server")
+        # Ignore linter error since we are creating a `Clock` for testing purposes.
+        clock = Clock(reactor, server_name="test_server")  # type: ignore[multiple-internal-clocks]
 
         # Sanity check that we start in the sentinel context
         self._check_test_key("sentinel")
@@ -645,7 +656,7 @@ class LoggingContextTestCase(unittest.TestCase):
         # the synapse rules.
         def blocking_function() -> defer.Deferred:
             d: defer.Deferred = defer.Deferred()
-            reactor.callLater(0, d.callback, None)
+            reactor.callLater(0, d.callback, None)  # type: ignore[call-later-not-tracked]
             return d
 
         sentinel_context = current_context()
@@ -692,7 +703,7 @@ def _chained_deferred_function() -> defer.Deferred:
 
     def cb(res: object) -> defer.Deferred:
         d2: defer.Deferred = defer.Deferred()
-        reactor.callLater(0, d2.callback, res)
+        reactor.callLater(0, d2.callback, res)  # type: ignore[call-later-not-tracked]
         return d2
 
     d.addCallback(cb)
diff --git a/tests/util/test_lrucache.py b/tests/util/test_lrucache.py
index 4d37ad0975..dcbfcfa2e4 100644
--- a/tests/util/test_lrucache.py
+++ b/tests/util/test_lrucache.py
@@ -20,7 +20,6 @@
 #
 
 
-from typing import List, Tuple
 from unittest.mock import Mock, patch
 
 from synapse.metrics.jemalloc import JemallocStats
@@ -29,18 +28,28 @@ from synapse.util.caches.lrucache import LruCache, setup_expire_lru_cache_entrie
 from synapse.util.caches.treecache import TreeCache
 
 from tests import unittest
+from tests.server import get_clock
 from tests.unittest import override_config
 
 
 class LruCacheTestCase(unittest.HomeserverTestCase):
+    def setUp(self) -> None:
+        super().setUp()
+
+        _, self.clock = get_clock()
+
     def test_get_set(self) -> None:
-        cache: LruCache[str, str] = LruCache(max_size=1, server_name="test_server")
+        cache: LruCache[str, str] = LruCache(
+            max_size=1, clock=self.clock, server_name="test_server"
+        )
         cache["key"] = "value"
         self.assertEqual(cache.get("key"), "value")
         self.assertEqual(cache["key"], "value")
 
     def test_eviction(self) -> None:
-        cache: LruCache[int, int] = LruCache(max_size=2, server_name="test_server")
+        cache: LruCache[int, int] = LruCache(
+            max_size=2, clock=self.clock, server_name="test_server"
+        )
         cache[1] = 1
         cache[2] = 2
 
@@ -54,7 +63,9 @@ class LruCacheTestCase(unittest.HomeserverTestCase):
         self.assertEqual(cache.get(3), 3)
 
     def test_setdefault(self) -> None:
-        cache: LruCache[str, int] = LruCache(max_size=1, server_name="test_server")
+        cache: LruCache[str, int] = LruCache(
+            max_size=1, clock=self.clock, server_name="test_server"
+        )
         self.assertEqual(cache.setdefault("key", 1), 1)
         self.assertEqual(cache.get("key"), 1)
         self.assertEqual(cache.setdefault("key", 2), 1)
@@ -63,15 +74,20 @@ class LruCacheTestCase(unittest.HomeserverTestCase):
         self.assertEqual(cache.get("key"), 2)
 
     def test_pop(self) -> None:
-        cache: LruCache[str, int] = LruCache(max_size=1, server_name="test_server")
+        cache: LruCache[str, int] = LruCache(
+            max_size=1, clock=self.clock, server_name="test_server"
+        )
         cache["key"] = 1
         self.assertEqual(cache.pop("key"), 1)
         self.assertEqual(cache.pop("key"), None)
 
     def test_del_multi(self) -> None:
         # The type here isn't quite correct as they don't handle TreeCache well.
-        cache: LruCache[Tuple[str, str], str] = LruCache(
-            max_size=4, cache_type=TreeCache, server_name="test_server"
+        cache: LruCache[tuple[str, str], str] = LruCache(
+            max_size=4,
+            clock=self.clock,
+            cache_type=TreeCache,
+            server_name="test_server",
         )
         cache[("animal", "cat")] = "mew"
         cache[("animal", "dog")] = "woof"
@@ -91,7 +107,9 @@ class LruCacheTestCase(unittest.HomeserverTestCase):
         # Man from del_multi say "Yes".
 
     def test_clear(self) -> None:
-        cache: LruCache[str, int] = LruCache(max_size=1, server_name="test_server")
+        cache: LruCache[str, int] = LruCache(
+            max_size=1, clock=self.clock, server_name="test_server"
+        )
         cache["key"] = 1
         cache.clear()
         self.assertEqual(len(cache), 0)
@@ -99,7 +117,10 @@ class LruCacheTestCase(unittest.HomeserverTestCase):
     @override_config({"caches": {"per_cache_factors": {"mycache": 10}}})
     def test_special_size(self) -> None:
         cache: LruCache = LruCache(
-            max_size=10, server_name="test_server", cache_name="mycache"
+            max_size=10,
+            clock=self.clock,
+            server_name="test_server",
+            cache_name="mycache",
         )
         self.assertEqual(cache.max_size, 100)
 
@@ -107,7 +128,9 @@ class LruCacheTestCase(unittest.HomeserverTestCase):
 class LruCacheCallbacksTestCase(unittest.HomeserverTestCase):
     def test_get(self) -> None:
         m = Mock()
-        cache: LruCache[str, str] = LruCache(max_size=1, server_name="test_server")
+        cache: LruCache[str, str] = LruCache(
+            max_size=1, clock=self.clock, server_name="test_server"
+        )
 
         cache.set("key", "value")
         self.assertFalse(m.called)
@@ -126,7 +149,9 @@ class LruCacheCallbacksTestCase(unittest.HomeserverTestCase):
 
     def test_multi_get(self) -> None:
         m = Mock()
-        cache: LruCache[str, str] = LruCache(max_size=1, server_name="test_server")
+        cache: LruCache[str, str] = LruCache(
+            max_size=1, clock=self.clock, server_name="test_server"
+        )
 
         cache.set("key", "value")
         self.assertFalse(m.called)
@@ -145,7 +170,9 @@ class LruCacheCallbacksTestCase(unittest.HomeserverTestCase):
 
     def test_set(self) -> None:
         m = Mock()
-        cache: LruCache[str, str] = LruCache(max_size=1, server_name="test_server")
+        cache: LruCache[str, str] = LruCache(
+            max_size=1, clock=self.clock, server_name="test_server"
+        )
 
         cache.set("key", "value", callbacks=[m])
         self.assertFalse(m.called)
@@ -161,7 +188,9 @@ class LruCacheCallbacksTestCase(unittest.HomeserverTestCase):
 
     def test_pop(self) -> None:
         m = Mock()
-        cache: LruCache[str, str] = LruCache(max_size=1, server_name="test_server")
+        cache: LruCache[str, str] = LruCache(
+            max_size=1, clock=self.clock, server_name="test_server"
+        )
 
         cache.set("key", "value", callbacks=[m])
         self.assertFalse(m.called)
@@ -181,8 +210,11 @@ class LruCacheCallbacksTestCase(unittest.HomeserverTestCase):
         m3 = Mock()
         m4 = Mock()
         # The type here isn't quite correct as they don't handle TreeCache well.
-        cache: LruCache[Tuple[str, str], str] = LruCache(
-            max_size=4, cache_type=TreeCache, server_name="test_server"
+        cache: LruCache[tuple[str, str], str] = LruCache(
+            max_size=4,
+            clock=self.clock,
+            cache_type=TreeCache,
+            server_name="test_server",
         )
 
         cache.set(("a", "1"), "value", callbacks=[m1])
@@ -205,7 +237,9 @@ class LruCacheCallbacksTestCase(unittest.HomeserverTestCase):
     def test_clear(self) -> None:
         m1 = Mock()
         m2 = Mock()
-        cache: LruCache[str, str] = LruCache(max_size=5, server_name="test_server")
+        cache: LruCache[str, str] = LruCache(
+            max_size=5, clock=self.clock, server_name="test_server"
+        )
 
         cache.set("key1", "value", callbacks=[m1])
         cache.set("key2", "value", callbacks=[m2])
@@ -222,7 +256,9 @@ class LruCacheCallbacksTestCase(unittest.HomeserverTestCase):
         m1 = Mock(name="m1")
         m2 = Mock(name="m2")
         m3 = Mock(name="m3")
-        cache: LruCache[str, str] = LruCache(max_size=2, server_name="test_server")
+        cache: LruCache[str, str] = LruCache(
+            max_size=2, clock=self.clock, server_name="test_server"
+        )
 
         cache.set("key1", "value", callbacks=[m1])
         cache.set("key2", "value", callbacks=[m2])
@@ -258,8 +294,8 @@ class LruCacheCallbacksTestCase(unittest.HomeserverTestCase):
 
 class LruCacheSizedTestCase(unittest.HomeserverTestCase):
     def test_evict(self) -> None:
-        cache: LruCache[str, List[int]] = LruCache(
-            max_size=5, size_callback=len, server_name="test_server"
+        cache: LruCache[str, list[int]] = LruCache(
+            max_size=5, clock=self.clock, size_callback=len, server_name="test_server"
         )
         cache["key1"] = [0]
         cache["key2"] = [1, 2]
@@ -283,8 +319,11 @@ class LruCacheSizedTestCase(unittest.HomeserverTestCase):
 
     def test_zero_size_drop_from_cache(self) -> None:
         """Test that `drop_from_cache` works correctly with 0-sized entries."""
-        cache: LruCache[str, List[int]] = LruCache(
-            max_size=5, size_callback=lambda x: 0, server_name="test_server"
+        cache: LruCache[str, list[int]] = LruCache(
+            max_size=5,
+            clock=self.clock,
+            size_callback=lambda x: 0,
+            server_name="test_server",
         )
         cache["key1"] = []
 
@@ -402,7 +441,10 @@ class MemoryEvictionTestCase(unittest.HomeserverTestCase):
 class ExtraIndexLruCacheTestCase(unittest.HomeserverTestCase):
     def test_invalidate_simple(self) -> None:
         cache: LruCache[str, int] = LruCache(
-            max_size=10, server_name="test_server", extra_index_cb=lambda k, v: str(v)
+            max_size=10,
+            clock=self.hs.get_clock(),
+            server_name="test_server",
+            extra_index_cb=lambda k, v: str(v),
         )
         cache["key1"] = 1
         cache["key2"] = 2
@@ -417,7 +459,10 @@ class ExtraIndexLruCacheTestCase(unittest.HomeserverTestCase):
 
     def test_invalidate_multi(self) -> None:
         cache: LruCache[str, int] = LruCache(
-            max_size=10, server_name="test_server", extra_index_cb=lambda k, v: str(v)
+            max_size=10,
+            clock=self.hs.get_clock(),
+            server_name="test_server",
+            extra_index_cb=lambda k, v: str(v),
         )
         cache["key1"] = 1
         cache["key2"] = 1
diff --git a/tests/util/test_mutable_overlay_mapping.py b/tests/util/test_mutable_overlay_mapping.py
index a7335fca73..ed738919e4 100644
--- a/tests/util/test_mutable_overlay_mapping.py
+++ b/tests/util/test_mutable_overlay_mapping.py
@@ -13,7 +13,6 @@
 #
 
 import unittest
-from typing import Dict
 
 from synapse.util import MutableOverlayMapping
 
@@ -24,7 +23,7 @@ class TestMutableOverlayMapping(unittest.TestCase):
     def test_init(self) -> None:
         """Test initialization with different input types."""
         # Test with empty dict
-        empty_dict: Dict[str, int] = {}
+        empty_dict: dict[str, int] = {}
         mapping = MutableOverlayMapping(empty_dict)
         self.assertEqual(len(mapping), 0)
 
diff --git a/tests/util/test_ratelimitutils.py b/tests/util/test_ratelimitutils.py
index 20281d04fe..d3b123c778 100644
--- a/tests/util/test_ratelimitutils.py
+++ b/tests/util/test_ratelimitutils.py
@@ -18,7 +18,6 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Optional
 
 from twisted.internet import defer
 from twisted.internet.defer import Deferred
@@ -139,7 +138,7 @@ def _await_resolution(reactor: ThreadedMemoryReactorClock, d: Deferred) -> float
     return (reactor.seconds() - start_time) * 1000
 
 
-def build_rc_config(settings: Optional[dict] = None) -> FederationRatelimitSettings:
+def build_rc_config(settings: dict | None = None) -> FederationRatelimitSettings:
     config_dict = default_config("test")
     config_dict.update(settings or {})
     config = HomeServerConfig()
diff --git a/tests/util/test_retryutils.py b/tests/util/test_retryutils.py
index 82baff5883..593be93ea3 100644
--- a/tests/util/test_retryutils.py
+++ b/tests/util/test_retryutils.py
@@ -35,6 +35,7 @@ class RetryLimiterTestCase(HomeserverTestCase):
             get_retry_limiter(
                 destination="test_dest",
                 our_server_name=self.hs.hostname,
+                hs=self.hs,
                 clock=self.clock,
                 store=store,
             )
@@ -57,6 +58,7 @@ class RetryLimiterTestCase(HomeserverTestCase):
             get_retry_limiter(
                 destination="test_dest",
                 our_server_name=self.hs.hostname,
+                hs=self.hs,
                 clock=self.clock,
                 store=store,
             )
@@ -89,6 +91,7 @@ class RetryLimiterTestCase(HomeserverTestCase):
             get_retry_limiter(
                 destination="test_dest",
                 our_server_name=self.hs.hostname,
+                hs=self.hs,
                 clock=self.clock,
                 store=store,
             ),
@@ -104,6 +107,7 @@ class RetryLimiterTestCase(HomeserverTestCase):
             get_retry_limiter(
                 destination="test_dest",
                 our_server_name=self.hs.hostname,
+                hs=self.hs,
                 clock=self.clock,
                 store=store,
             )
@@ -139,6 +143,7 @@ class RetryLimiterTestCase(HomeserverTestCase):
             get_retry_limiter(
                 destination="test_dest",
                 our_server_name=self.hs.hostname,
+                hs=self.hs,
                 clock=self.clock,
                 store=store,
             )
@@ -165,6 +170,7 @@ class RetryLimiterTestCase(HomeserverTestCase):
             get_retry_limiter(
                 destination="test_dest",
                 our_server_name=self.hs.hostname,
+                hs=self.hs,
                 clock=self.clock,
                 store=store,
                 notifier=notifier,
@@ -238,6 +244,7 @@ class RetryLimiterTestCase(HomeserverTestCase):
             get_retry_limiter(
                 destination="test_dest",
                 our_server_name=self.hs.hostname,
+                hs=self.hs,
                 clock=self.clock,
                 store=store,
             )
@@ -261,6 +268,7 @@ class RetryLimiterTestCase(HomeserverTestCase):
             get_retry_limiter(
                 destination="test_dest",
                 our_server_name=self.hs.hostname,
+                hs=self.hs,
                 clock=self.clock,
                 store=store,
             ),
@@ -273,6 +281,7 @@ class RetryLimiterTestCase(HomeserverTestCase):
             get_retry_limiter(
                 destination="test_dest",
                 our_server_name=self.hs.hostname,
+                hs=self.hs,
                 clock=self.clock,
                 store=store,
             )
@@ -297,6 +306,7 @@ class RetryLimiterTestCase(HomeserverTestCase):
             get_retry_limiter(
                 destination="test_dest",
                 our_server_name=self.hs.hostname,
+                hs=self.hs,
                 clock=self.clock,
                 store=store,
             ),
diff --git a/tests/util/test_rwlock.py b/tests/util/test_rwlock.py
index 12f821d684..36771188ae 100644
--- a/tests/util/test_rwlock.py
+++ b/tests/util/test_rwlock.py
@@ -19,7 +19,7 @@
 #
 #
 
-from typing import AsyncContextManager, Callable, Sequence, Tuple
+from typing import AsyncContextManager, Callable, Sequence
 
 from twisted.internet import defer
 from twisted.internet.defer import CancelledError, Deferred
@@ -35,7 +35,7 @@ class ReadWriteLockTestCase(unittest.TestCase):
         read_or_write: Callable[[str], AsyncContextManager],
         key: str,
         return_value: str,
-    ) -> Tuple["Deferred[str]", "Deferred[None]", "Deferred[None]"]:
+    ) -> tuple["Deferred[str]", "Deferred[None]", "Deferred[None]"]:
         """Starts a reader or writer which acquires the lock, blocks, then completes.
 
         Args:
@@ -67,7 +67,7 @@ class ReadWriteLockTestCase(unittest.TestCase):
 
     def _start_blocking_reader(
         self, rwlock: ReadWriteLock, key: str, return_value: str
-    ) -> Tuple["Deferred[str]", "Deferred[None]", "Deferred[None]"]:
+    ) -> tuple["Deferred[str]", "Deferred[None]", "Deferred[None]"]:
         """Starts a reader which acquires the lock, blocks, then releases the lock.
 
         See the docstring for `_start_reader_or_writer` for details about the arguments
@@ -77,7 +77,7 @@ class ReadWriteLockTestCase(unittest.TestCase):
 
     def _start_blocking_writer(
         self, rwlock: ReadWriteLock, key: str, return_value: str
-    ) -> Tuple["Deferred[str]", "Deferred[None]", "Deferred[None]"]:
+    ) -> tuple["Deferred[str]", "Deferred[None]", "Deferred[None]"]:
         """Starts a writer which acquires the lock, blocks, then releases the lock.
 
         See the docstring for `_start_reader_or_writer` for details about the arguments
@@ -87,7 +87,7 @@ class ReadWriteLockTestCase(unittest.TestCase):
 
     def _start_nonblocking_reader(
         self, rwlock: ReadWriteLock, key: str, return_value: str
-    ) -> Tuple["Deferred[str]", "Deferred[None]"]:
+    ) -> tuple["Deferred[str]", "Deferred[None]"]:
         """Starts a reader which acquires the lock, then releases it immediately.
 
         See the docstring for `_start_reader_or_writer` for details about the arguments.
@@ -106,7 +106,7 @@ class ReadWriteLockTestCase(unittest.TestCase):
 
     def _start_nonblocking_writer(
         self, rwlock: ReadWriteLock, key: str, return_value: str
-    ) -> Tuple["Deferred[str]", "Deferred[None]"]:
+    ) -> tuple["Deferred[str]", "Deferred[None]"]:
         """Starts a writer which acquires the lock, then releases it immediately.
 
         See the docstring for `_start_reader_or_writer` for details about the arguments.
diff --git a/tests/util/test_task_scheduler.py b/tests/util/test_task_scheduler.py
index e97f0ed611..e33ded8a7f 100644
--- a/tests/util/test_task_scheduler.py
+++ b/tests/util/test_task_scheduler.py
@@ -18,11 +18,11 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import List, Optional, Tuple
 
-from twisted.internet.task import deferLater
+from twisted.internet.defer import Deferred
 from twisted.internet.testing import MemoryReactor
 
+from synapse.logging.context import make_deferred_yieldable
 from synapse.server import HomeServer
 from synapse.types import JsonMapping, ScheduledTask, TaskStatus
 from synapse.util.clock import Clock
@@ -42,7 +42,7 @@ class TestTaskScheduler(HomeserverTestCase):
 
     async def _test_task(
         self, task: ScheduledTask
-    ) -> Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]:
+    ) -> tuple[TaskStatus, JsonMapping | None, str | None]:
         # This test task will copy the parameters to the result
         result = None
         if task.params:
@@ -85,9 +85,9 @@ class TestTaskScheduler(HomeserverTestCase):
 
     async def _sleeping_task(
         self, task: ScheduledTask
-    ) -> Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]:
+    ) -> tuple[TaskStatus, JsonMapping | None, str | None]:
         # Sleep for a second
-        await deferLater(self.reactor, 1, lambda: None)
+        await self.hs.get_clock().sleep(1)
         return TaskStatus.COMPLETE, None, None
 
     def test_schedule_lot_of_tasks(self) -> None:
@@ -103,7 +103,7 @@ class TestTaskScheduler(HomeserverTestCase):
                 )
             )
 
-        def get_tasks_of_status(status: TaskStatus) -> List[ScheduledTask]:
+        def get_tasks_of_status(status: TaskStatus) -> list[ScheduledTask]:
             tasks = (
                 self.get_success(self.task_scheduler.get_task(task_id))
                 for task_id in task_ids
@@ -151,7 +151,7 @@ class TestTaskScheduler(HomeserverTestCase):
 
     async def _raising_task(
         self, task: ScheduledTask
-    ) -> Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]:
+    ) -> tuple[TaskStatus, JsonMapping | None, str | None]:
         raise Exception("raising")
 
     def test_schedule_raising_task(self) -> None:
@@ -165,13 +165,15 @@ class TestTaskScheduler(HomeserverTestCase):
 
     async def _resumable_task(
         self, task: ScheduledTask
-    ) -> Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]:
+    ) -> tuple[TaskStatus, JsonMapping | None, str | None]:
         if task.result and "in_progress" in task.result:
             return TaskStatus.COMPLETE, {"success": True}, None
         else:
             await self.task_scheduler.update_task(task.id, result={"in_progress": True})
+            # Create a deferred which we will never complete
+            incomplete_d: Deferred = Deferred()
             # Await forever to simulate an aborted task because of a restart
-            await deferLater(self.reactor, 2**16, lambda: None)
+            await make_deferred_yieldable(incomplete_d)
             # This should never been called
             return TaskStatus.ACTIVE, None, None
 
@@ -201,7 +203,7 @@ class TestTaskSchedulerWithBackgroundWorker(BaseMultiWorkerStreamTestCase):
 
     async def _test_task(
         self, task: ScheduledTask
-    ) -> Tuple[TaskStatus, Optional[JsonMapping], Optional[str]]:
+    ) -> tuple[TaskStatus, JsonMapping | None, str | None]:
         return (TaskStatus.COMPLETE, None, None)
 
     @override_config({"run_background_tasks_on": "worker1"})
diff --git a/tests/utils.py b/tests/utils.py
index d1b66d4159..4052c9a4fb 100644
--- a/tests/utils.py
+++ b/tests/utils.py
@@ -24,27 +24,15 @@ import os
 import signal
 from types import FrameType, TracebackType
 from typing import (
-    Any,
-    Callable,
-    Dict,
-    List,
     Literal,
-    Optional,
-    Tuple,
-    Type,
     TypeVar,
-    Union,
     overload,
 )
 
-import attr
-from typing_extensions import ParamSpec
-
 from synapse.api.constants import EventTypes
 from synapse.api.room_versions import RoomVersions
 from synapse.config.homeserver import HomeServerConfig
 from synapse.config.server import DEFAULT_ROOM_VERSION
-from synapse.logging.context import current_context, set_current_context
 from synapse.server import HomeServer
 from synapse.storage.database import LoggingDatabaseConnection
 from synapse.storage.engines import create_engine
@@ -140,21 +128,27 @@ def setupdb() -> None:
 
 
 @overload
-def default_config(name: str, parse: Literal[False] = ...) -> Dict[str, object]: ...
+def default_config(
+    server_name: str, parse: Literal[False] = ...
+) -> dict[str, object]: ...
 
 
 @overload
-def default_config(name: str, parse: Literal[True]) -> HomeServerConfig: ...
+def default_config(server_name: str, parse: Literal[True]) -> HomeServerConfig: ...
 
 
 def default_config(
-    name: str, parse: bool = False
-) -> Union[Dict[str, object], HomeServerConfig]:
+    server_name: str, parse: bool = False
+) -> dict[str, object] | HomeServerConfig:
     """
     Create a reasonable test config.
+
+    Args:
+        server_name: homeserver name
+        parse: TODO
     """
     config_dict = {
-        "server_name": name,
+        "server_name": server_name,
         # Setting this to an empty list turns off federation sending.
         "federation_sender_instances": [],
         "media_store_path": "media",
@@ -247,101 +241,6 @@ def mock_getRawHeaders(headers=None):  # type: ignore[no-untyped-def]
     return getRawHeaders
 
 
-P = ParamSpec("P")
-
-
-@attr.s(slots=True, auto_attribs=True)
-class Timer:
-    absolute_time: float
-    callback: Callable[[], None]
-    expired: bool
-
-
-# TODO: Make this generic over a ParamSpec?
-@attr.s(slots=True, auto_attribs=True)
-class Looper:
-    func: Callable[..., Any]
-    interval: float  # seconds
-    last: float
-    args: Tuple[object, ...]
-    kwargs: Dict[str, object]
-
-
-class MockClock:
-    now = 1000.0
-
-    def __init__(self) -> None:
-        # Timers in no particular order
-        self.timers: List[Timer] = []
-        self.loopers: List[Looper] = []
-
-    def time(self) -> float:
-        return self.now
-
-    def time_msec(self) -> int:
-        return int(self.time() * 1000)
-
-    def call_later(
-        self,
-        delay: float,
-        callback: Callable[P, object],
-        *args: P.args,
-        **kwargs: P.kwargs,
-    ) -> Timer:
-        ctx = current_context()
-
-        def wrapped_callback() -> None:
-            set_current_context(ctx)
-            callback(*args, **kwargs)
-
-        t = Timer(self.now + delay, wrapped_callback, False)
-        self.timers.append(t)
-
-        return t
-
-    def looping_call(
-        self,
-        function: Callable[P, object],
-        interval: float,
-        *args: P.args,
-        **kwargs: P.kwargs,
-    ) -> None:
-        self.loopers.append(Looper(function, interval / 1000.0, self.now, args, kwargs))
-
-    def cancel_call_later(self, timer: Timer, ignore_errs: bool = False) -> None:
-        if timer.expired:
-            if not ignore_errs:
-                raise Exception("Cannot cancel an expired timer")
-
-        timer.expired = True
-        self.timers = [t for t in self.timers if t != timer]
-
-    # For unit testing
-    def advance_time(self, secs: float) -> None:
-        self.now += secs
-
-        timers = self.timers
-        self.timers = []
-
-        for t in timers:
-            if t.expired:
-                raise Exception("Timer already expired")
-
-            if self.now >= t.absolute_time:
-                t.expired = True
-                t.callback()
-            else:
-                self.timers.append(t)
-
-        for looped in self.loopers:
-            if looped.last + looped.interval < self.now:
-                looped.func(*looped.args, **looped.kwargs)
-                looped.last = self.now
-
-    def advance_time_msec(self, ms: float) -> None:
-        self.advance_time(ms / 1000.0)
-
-
 async def create_room(hs: HomeServer, room_id: str, creator_id: str) -> None:
     """Creates and persist a creation event for the given room"""
 
@@ -380,7 +279,7 @@ async def create_room(hs: HomeServer, room_id: str, creator_id: str) -> None:
 T = TypeVar("T")
 
 
-def checked_cast(type: Type[T], x: object) -> T:
+def checked_cast(type: type[T], x: object) -> T:
     """A version of typing.cast that is checked at runtime.
 
     We have our own function for this for two reasons:
@@ -419,13 +318,13 @@ class test_timeout:
     ```
     """
 
-    def __init__(self, seconds: int, error_message: Optional[str] = None) -> None:
+    def __init__(self, seconds: int, error_message: str | None = None) -> None:
         self.error_message = f"Test timed out after {seconds}s"
         if error_message is not None:
             self.error_message += f": {error_message}"
         self.seconds = seconds
 
-    def handle_timeout(self, signum: int, frame: Optional[FrameType]) -> None:
+    def handle_timeout(self, signum: int, frame: FrameType | None) -> None:
         raise TestTimeout(self.error_message)
 
     def __enter__(self) -> None:
@@ -434,8 +333,8 @@ class test_timeout:
 
     def __exit__(
         self,
-        exc_type: Optional[Type[BaseException]],
-        exc_val: Optional[BaseException],
-        exc_tb: Optional[TracebackType],
+        exc_type: type[BaseException] | None,
+        exc_val: BaseException | None,
+        exc_tb: TracebackType | None,
     ) -> None:
         signal.alarm(0)
diff --git a/tox.ini b/tox.ini
index a506b5034d..a0e397bbbf 100644
--- a/tox.ini
+++ b/tox.ini
@@ -1,5 +1,5 @@
 [tox]
-envlist = py39, py310, py311, py312, py313
+envlist = py310, py311, py312, py313
 
 # we require tox>=2.3.2 for the fix to https://github.com/tox-dev/tox/issues/208
 minversion = 2.3.2