Merge remote-tracking branch 'origin/develop' into clokep/psycopg3

69 files changed, 1210 insertions, 416 deletions

diff --git a/.github/workflows/docker.yml b/.github/workflows/docker.yml
index a1793b9010..ebad0d4a98 100644
--- a/.github/workflows/docker.yml
+++ b/.github/workflows/docker.yml
@@ -24,13 +24,13 @@ jobs:
 
       - name: Set up Docker Buildx
         id: buildx
-        uses: docker/setup-buildx-action@v2
+        uses: docker/setup-buildx-action@v3
 
       - name: Inspect builder
         run: docker buildx inspect
 
       - name: Checkout repository
-        uses: actions/checkout@v3
+        uses: actions/checkout@v4
 
       - name: Extract version from pyproject.toml
         # Note: explicitly requesting bash will mean bash is invoked with `-eo pipefail`, see
diff --git a/.github/workflows/docs-pr-netlify.yaml b/.github/workflows/docs-pr-netlify.yaml
index 928bcae8cf..b443cd87d1 100644
--- a/.github/workflows/docs-pr-netlify.yaml
+++ b/.github/workflows/docs-pr-netlify.yaml
@@ -14,7 +14,7 @@ jobs:
       # There's a 'download artifact' action, but it hasn't been updated for the workflow_run action
       # (https://github.com/actions/download-artifact/issues/60) so instead we get this mess:
       - name: 📥 Download artifact
-        uses: dawidd6/action-download-artifact@246dbf436b23d7c49e21a7ab8204ca9ecd1fe615 # v2.27.0
+        uses: dawidd6/action-download-artifact@268677152d06ba59fcec7a7f0b5d961b6ccd7e1e # v2.28.0
         with:
           workflow: docs-pr.yaml
           run_id: ${{ github.event.workflow_run.id }}
diff --git a/.github/workflows/docs-pr.yaml b/.github/workflows/docs-pr.yaml
index 6634f2644e..3704bd66e2 100644
--- a/.github/workflows/docs-pr.yaml
+++ b/.github/workflows/docs-pr.yaml
@@ -12,7 +12,7 @@ jobs:
     name: GitHub Pages
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
 
       - name: Setup mdbook
         uses: peaceiris/actions-mdbook@adeb05db28a0c0004681db83893d56c0388ea9ea # v1.2.0
@@ -39,7 +39,7 @@ jobs:
     name: Check links in documentation
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
 
       - name: Setup mdbook
         uses: peaceiris/actions-mdbook@adeb05db28a0c0004681db83893d56c0388ea9ea # v1.2.0
diff --git a/.github/workflows/docs.yaml b/.github/workflows/docs.yaml
index 2bd0f32566..c7cb2d78e5 100644
--- a/.github/workflows/docs.yaml
+++ b/.github/workflows/docs.yaml
@@ -50,7 +50,7 @@ jobs:
     needs:
       - pre
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
 
       - name: Setup mdbook
         uses: peaceiris/actions-mdbook@adeb05db28a0c0004681db83893d56c0388ea9ea # v1.2.0
@@ -80,7 +80,7 @@ jobs:
     needs:
       - pre
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
 
       - name: "Set up Sphinx"
         uses: matrix-org/setup-python-poetry@v1
diff --git a/.github/workflows/latest_deps.yml b/.github/workflows/latest_deps.yml
index 7b839f59c1..c9ec70abe9 100644
--- a/.github/workflows/latest_deps.yml
+++ b/.github/workflows/latest_deps.yml
@@ -39,7 +39,7 @@ jobs:
     if: needs.check_repo.outputs.should_run_workflow == 'true'
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
       - name: Install Rust
         uses: dtolnay/rust-toolchain@stable
       - uses: Swatinem/rust-cache@v2
@@ -72,7 +72,7 @@ jobs:
             postgres-version: "14"
 
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
 
       - name: Install Rust
         uses: dtolnay/rust-toolchain@stable
@@ -145,7 +145,7 @@ jobs:
       BLACKLIST: ${{ matrix.workers && 'synapse-blacklist-with-workers' }}
 
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
 
       - name: Install Rust
         uses: dtolnay/rust-toolchain@stable
@@ -192,8 +192,8 @@ jobs:
             database: Postgres
 
     steps:
-      - name: Run actions/checkout@v3 for synapse
-        uses: actions/checkout@v3
+      - name: Run actions/checkout@v4 for synapse
+        uses: actions/checkout@v4
         with:
           path: synapse
 
@@ -222,7 +222,7 @@ jobs:
     runs-on: ubuntu-latest
 
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
       - uses: JasonEtco/create-an-issue@e27dddc79c92bc6e4562f268fffa5ed752639abd # v2.9.1
         env:
           GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
diff --git a/.github/workflows/poetry_lockfile.yaml b/.github/workflows/poetry_lockfile.yaml
index ae4d27f2de..4dd0f7d41f 100644
--- a/.github/workflows/poetry_lockfile.yaml
+++ b/.github/workflows/poetry_lockfile.yaml
@@ -16,7 +16,7 @@ jobs:
     name: "Check locked dependencies have sdists"
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
       - uses: actions/setup-python@v4
         with:
           python-version: '3.x'
diff --git a/.github/workflows/push_complement_image.yml b/.github/workflows/push_complement_image.yml
index e994b122cd..6fbd2ed015 100644
--- a/.github/workflows/push_complement_image.yml
+++ b/.github/workflows/push_complement_image.yml
@@ -33,17 +33,17 @@ jobs:
       packages: write
     steps:
       - name: Checkout specific branch (debug build)
-        uses: actions/checkout@v3
+        uses: actions/checkout@v4
         if: github.event_name == 'workflow_dispatch'
         with:
           ref: ${{ inputs.branch }}
       - name: Checkout clean copy of develop (scheduled build)
-        uses: actions/checkout@v3
+        uses: actions/checkout@v4
         if: github.event_name == 'schedule'
         with:
           ref: develop
       - name: Checkout clean copy of master (on-push)
-        uses: actions/checkout@v3
+        uses: actions/checkout@v4
         if: github.event_name == 'push'
         with:
           ref: master
diff --git a/.github/workflows/release-artifacts.yml b/.github/workflows/release-artifacts.yml
index f031127cce..fed3a41586 100644
--- a/.github/workflows/release-artifacts.yml
+++ b/.github/workflows/release-artifacts.yml
@@ -27,7 +27,7 @@ jobs:
     name: "Calculate list of debian distros"
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
       - uses: actions/setup-python@v4
         with:
           python-version: '3.x'
@@ -55,13 +55,13 @@ jobs:
 
     steps:
       - name: Checkout
-        uses: actions/checkout@v3
+        uses: actions/checkout@v4
         with:
           path: src
 
       - name: Set up Docker Buildx
         id: buildx
-        uses: docker/setup-buildx-action@v2
+        uses: docker/setup-buildx-action@v3
         with:
           install: true
 
@@ -121,7 +121,7 @@ jobs:
             arch: aarch64
 
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
 
       - uses: actions/setup-python@v4
         with:
@@ -167,7 +167,7 @@ jobs:
     if: ${{ !startsWith(github.ref, 'refs/pull/') }}
 
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
       - uses: actions/setup-python@v4
         with:
           python-version: '3.10'
diff --git a/.github/workflows/tests.yml b/.github/workflows/tests.yml
index fb117380d0..96750cb6c8 100644
--- a/.github/workflows/tests.yml
+++ b/.github/workflows/tests.yml
@@ -12,12 +12,19 @@ concurrency:
   cancel-in-progress: true
 
 jobs:
+  check-signoff:
+    if: "github.event_name == 'pull_request'"
+    uses: "matrix-org/backend-meta/.github/workflows/sign-off.yml@v2"
+
   # Job to detect what has changed so we don't run e.g. Rust checks on PRs that
   # don't modify Rust code.
   changes:
     runs-on: ubuntu-latest
     outputs:
       rust: ${{ !startsWith(github.ref, 'refs/pull/') || steps.filter.outputs.rust }}
+      trial: ${{ !startsWith(github.ref, 'refs/pull/') || steps.filter.outputs.trial }}
+      integration: ${{ !startsWith(github.ref, 'refs/pull/') || steps.filter.outputs.integration }}
+      linting: ${{ !startsWith(github.ref, 'refs/pull/') || steps.filter.outputs.linting }}
     steps:
     - uses: dorny/paths-filter@v2
       id: filter
@@ -29,11 +36,47 @@ jobs:
             - 'rust/**'
             - 'Cargo.toml'
             - 'Cargo.lock'
+            - '.rustfmt.toml'
+
+          trial:
+            - 'synapse/**'
+            - 'tests/**'
+            - 'rust/**'
+            - 'Cargo.toml'
+            - 'Cargo.lock'
+            - 'pyproject.toml'
+            - 'poetry.lock'
+
+          integration:
+            - 'synapse/**'
+            - 'rust/**'
+            - 'docker/**'
+            - 'Cargo.toml'
+            - 'Cargo.lock'
+            - 'pyproject.toml'
+            - 'poetry.lock'
+            - 'docker/**'
+
+          linting:
+            - 'synapse/**'
+            - 'docker/**'
+            - 'tests/**'
+            - 'scripts-dev/**'
+            - 'contrib/**'
+            - 'synmark/**'
+            - 'stubs/**'
+            - '.ci/**'
+            - 'mypy.ini'
+            - 'pyproject.toml'
+            - 'poetry.lock'
 
   check-sampleconfig:
     runs-on: ubuntu-latest
+    needs: changes
+    if: ${{ needs.changes.outputs.linting == 'true' }}
+
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
       - name: Install Rust
         uses: dtolnay/rust-toolchain@1.61.0
       - uses: Swatinem/rust-cache@v2
@@ -47,8 +90,11 @@ jobs:
 
   check-schema-delta:
     runs-on: ubuntu-latest
+    needs: changes
+    if: ${{ needs.changes.outputs.linting == 'true' }}
+
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
       - uses: actions/setup-python@v4
         with:
           python-version: "3.x"
@@ -58,7 +104,7 @@ jobs:
   check-lockfile:
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
       - uses: actions/setup-python@v4
         with:
           python-version: "3.x"
@@ -66,9 +112,12 @@ jobs:
 
   lint:
     runs-on: ubuntu-latest
+    needs: changes
+    if: ${{ needs.changes.outputs.linting == 'true' }}
+
     steps:
       - name: Checkout repository
-        uses: actions/checkout@v3
+        uses: actions/checkout@v4
 
       - name: Setup Poetry
         uses: matrix-org/setup-python-poetry@v1
@@ -88,9 +137,12 @@ jobs:
   lint-mypy:
     runs-on: ubuntu-latest
     name: Typechecking
+    needs: changes
+    if: ${{ needs.changes.outputs.linting == 'true' }}
+
     steps:
       - name: Checkout repository
-        uses: actions/checkout@v3
+        uses: actions/checkout@v4
 
       - name: Install Rust
         uses: dtolnay/rust-toolchain@1.61.0
@@ -123,7 +175,7 @@ jobs:
   lint-crlf:
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
       - name: Check line endings
         run: scripts-dev/check_line_terminators.sh
 
@@ -131,7 +183,7 @@ jobs:
     if: ${{ (github.base_ref == 'develop'  || contains(github.base_ref, 'release-')) && github.actor != 'dependabot[bot]' }}
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
         with:
           ref: ${{ github.event.pull_request.head.sha }}
           fetch-depth: 0
@@ -145,8 +197,11 @@ jobs:
 
   lint-pydantic:
     runs-on: ubuntu-latest
+    needs: changes
+    if: ${{ needs.changes.outputs.linting == 'true' }}
+
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
         with:
           ref: ${{ github.event.pull_request.head.sha }}
       - name: Install Rust
@@ -164,7 +219,7 @@ jobs:
     if: ${{ needs.changes.outputs.rust == 'true' }}
 
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
 
       - name: Install Rust
         uses: dtolnay/rust-toolchain@1.61.0
@@ -182,7 +237,7 @@ jobs:
     if: ${{ needs.changes.outputs.rust == 'true' }}
 
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
 
       - name: Install Rust
         uses: dtolnay/rust-toolchain@master
@@ -199,7 +254,7 @@ jobs:
     if: ${{ needs.changes.outputs.rust == 'true' }}
 
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
 
       - name: Install Rust
         uses: dtolnay/rust-toolchain@master
@@ -225,6 +280,7 @@ jobs:
       - check-lockfile
       - lint-clippy
       - lint-rustfmt
+      - check-signoff
     runs-on: ubuntu-latest
     steps:
       - run: "true"
@@ -234,7 +290,7 @@ jobs:
     needs: linting-done
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
       - uses: actions/setup-python@v4
         with:
           python-version: "3.x"
@@ -245,15 +301,17 @@ jobs:
       sytest_test_matrix: ${{ steps.get-matrix.outputs.sytest_test_matrix }}
 
   trial:
-    if: ${{ !cancelled() && !failure() }} # Allow previous steps to be skipped, but not fail
-    needs: calculate-test-jobs
+    if: ${{ !cancelled() && !failure() && needs.changes.outputs.trial == 'true' }} # Allow previous steps to be skipped, but not fail
+    needs:
+      - calculate-test-jobs
+      - changes
     runs-on: ubuntu-latest
     strategy:
       matrix:
         job:  ${{ fromJson(needs.calculate-test-jobs.outputs.trial_test_matrix) }}
 
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
       - run: sudo apt-get -qq install xmlsec1
       - name: Set up PostgreSQL ${{ matrix.job.postgres-version }}
         if: ${{ matrix.job.postgres-version }}
@@ -301,11 +359,13 @@ jobs:
 
   trial-olddeps:
     # Note: sqlite only; no postgres
-    if: ${{ !cancelled() && !failure() }} # Allow previous steps to be skipped, but not fail
-    needs: linting-done
+    if: ${{ !cancelled() && !failure() && needs.changes.outputs.trial == 'true' }} # Allow previous steps to be skipped, but not fail
+    needs:
+      - linting-done
+      - changes
     runs-on: ubuntu-20.04
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
 
       - name: Install Rust
         uses: dtolnay/rust-toolchain@1.61.0
@@ -357,8 +417,10 @@ jobs:
   trial-pypy:
     # Very slow; only run if the branch name includes 'pypy'
     # Note: sqlite only; no postgres. Completely untested since poetry move.
-    if: ${{ contains(github.ref, 'pypy') && !failure() && !cancelled() }}
-    needs: linting-done
+    if: ${{ contains(github.ref, 'pypy') && !failure() && !cancelled() && needs.changes.outputs.trial == 'true' }}
+    needs:
+      - linting-done
+      - changes
     runs-on: ubuntu-latest
     strategy:
       matrix:
@@ -366,7 +428,7 @@ jobs:
         extras: ["all"]
 
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
       # Install libs necessary for PyPy to build binary wheels for dependencies
       - run: sudo apt-get -qq install xmlsec1 libxml2-dev libxslt-dev
       - uses: matrix-org/setup-python-poetry@v1
@@ -389,8 +451,10 @@ jobs:
           || true
 
   sytest:
-    if: ${{ !failure() && !cancelled() }}
-    needs: calculate-test-jobs
+    if: ${{ !failure() && !cancelled() && needs.changes.outputs.integration == 'true' }}
+    needs:
+      - calculate-test-jobs
+      - changes
     runs-on: ubuntu-latest
     container:
       image: matrixdotorg/sytest-synapse:${{ matrix.job.sytest-tag }}
@@ -411,7 +475,7 @@ jobs:
         job: ${{ fromJson(needs.calculate-test-jobs.outputs.sytest_test_matrix) }}
 
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
       - name: Prepare test blacklist
         run: cat sytest-blacklist .ci/worker-blacklist > synapse-blacklist-with-workers
 
@@ -435,8 +499,8 @@ jobs:
             /logs/**/*.log*
 
   export-data:
-    if: ${{ !failure() && !cancelled() }} # Allow previous steps to be skipped, but not fail
-    needs: [linting-done, portdb]
+    if: ${{ !failure() && !cancelled() && needs.changes.outputs.integration == 'true'}} # Allow previous steps to be skipped, but not fail
+    needs: [linting-done, portdb, changes]
     runs-on: ubuntu-latest
     env:
       TOP: ${{ github.workspace }}
@@ -456,7 +520,7 @@ jobs:
           --health-retries 5
 
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
       - run: sudo apt-get -qq install xmlsec1 postgresql-client
       - uses: matrix-org/setup-python-poetry@v1
         with:
@@ -471,8 +535,10 @@ jobs:
 
 
   portdb:
-    if: ${{ !failure() && !cancelled() }} # Allow previous steps to be skipped, but not fail
-    needs: linting-done
+    if: ${{ !failure() && !cancelled() && needs.changes.outputs.integration == 'true'}} # Allow previous steps to be skipped, but not fail
+    needs:
+      - linting-done
+      - changes
     runs-on: ubuntu-latest
     strategy:
       matrix:
@@ -498,7 +564,7 @@ jobs:
           --health-retries 5
 
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
       - name: Add PostgreSQL apt repository
         # We need a version of pg_dump that can handle the version of
         # PostgreSQL being tested against. The Ubuntu package repository lags
@@ -532,8 +598,10 @@ jobs:
             schema_diff
 
   complement:
-    if: "${{ !failure() && !cancelled() }}"
-    needs: linting-done
+    if: "${{ !failure() && !cancelled() && needs.changes.outputs.integration == 'true' }}"
+    needs:
+      - linting-done
+      - changes
     runs-on: ubuntu-latest
 
     strategy:
@@ -550,8 +618,8 @@ jobs:
             database: Postgres
 
     steps:
-      - name: Run actions/checkout@v3 for synapse
-        uses: actions/checkout@v3
+      - name: Run actions/checkout@v4 for synapse
+        uses: actions/checkout@v4
         with:
           path: synapse
 
@@ -581,7 +649,7 @@ jobs:
       - changes
 
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
 
       - name: Install Rust
         uses: dtolnay/rust-toolchain@1.61.0
@@ -599,7 +667,7 @@ jobs:
       - changes
 
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
 
       - name: Install Rust
         uses: dtolnay/rust-toolchain@master
@@ -627,9 +695,16 @@ jobs:
         with:
           needs: ${{ toJSON(needs) }}
 
-          # The newsfile lint may be skipped on non PR builds
-          # Cargo test is skipped if there is no changes on Rust code
+          # Various bits are skipped if there was no applicable changes.
+          # The newsfile and signoff lint may be skipped on non PR builds.
           skippable: |
+            trial
+            trial-olddeps
+            sytest
+            portdb
+            export-data
+            complement
+            check-signoff
             lint-newsfile
             cargo-test
             cargo-bench
diff --git a/.github/workflows/twisted_trunk.yml b/.github/workflows/twisted_trunk.yml
index 7d629a4ed0..062f782e8b 100644
--- a/.github/workflows/twisted_trunk.yml
+++ b/.github/workflows/twisted_trunk.yml
@@ -40,7 +40,7 @@ jobs:
     runs-on: ubuntu-latest
 
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
 
       - name: Install Rust
         uses: dtolnay/rust-toolchain@stable
@@ -64,7 +64,7 @@ jobs:
     runs-on: ubuntu-latest
 
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
       - run: sudo apt-get -qq install xmlsec1
 
       - name: Install Rust
@@ -108,7 +108,7 @@ jobs:
         - ${{ github.workspace }}:/src
 
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
 
       - name: Install Rust
         uses: dtolnay/rust-toolchain@stable
@@ -163,8 +163,8 @@ jobs:
             database: Postgres
 
     steps:
-      - name: Run actions/checkout@v3 for synapse
-        uses: actions/checkout@v3
+      - name: Run actions/checkout@v4 for synapse
+        uses: actions/checkout@v4
         with:
           path: synapse
 
@@ -203,7 +203,7 @@ jobs:
     runs-on: ubuntu-latest
 
     steps:
-      - uses: actions/checkout@v3
+      - uses: actions/checkout@v4
       - uses: JasonEtco/create-an-issue@e27dddc79c92bc6e4562f268fffa5ed752639abd # v2.9.1
         env:
           GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
diff --git a/CHANGES.md b/CHANGES.md
index eb537f9f6a..c1ea40de20 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -1,3 +1,23 @@
+# Synapse 1.93.0 (2023-09-26)
+
+No significant changes since 1.93.0rc1.
+
+
+## Security advisory
+
+The following issues are fixed in 1.93.0 (and RCs).
+
+- [GHSA-4f74-84v3-j9q5](https://github.com/matrix-org/synapse/security/advisories/GHSA-4f74-84v3-j9q5) / [CVE-2023-41335](https://cve.mitre.org/cgi-bin/cvename.cgi?name=CVE-2023-41335) — Low Severity
+
+  Temporary storage of plaintext passwords during password changes.
+
+- [GHSA-7565-cq32-vx2x](https://github.com/matrix-org/synapse/security/advisories/GHSA-7565-cq32-vx2x) / [CVE-2023-42453](https://cve.mitre.org/cgi-bin/cvename.cgi?name=CVE-2023-42453) — Low Severity
+
+  Improper validation of receipts allows forged read receipts.
+
+See the advisories for more details. If you have any questions, email security@matrix.org.
+
+
 # Synapse 1.93.0rc1 (2023-09-19)
 
 ### Features
diff --git a/changelog.d/14745.misc b/changelog.d/14745.misc
new file mode 100644
index 0000000000..eae0501d6b
--- /dev/null
+++ b/changelog.d/14745.misc
@@ -0,0 +1 @@
+Avoid running CI steps when the files they check have not been changed.
\ No newline at end of file
diff --git a/changelog.d/15691.doc b/changelog.d/15691.doc
new file mode 100644
index 0000000000..fe649e1027
--- /dev/null
+++ b/changelog.d/15691.doc
@@ -0,0 +1 @@
+Add developer documentation concerning gradual schema migrations with column alterations.
\ No newline at end of file
diff --git a/changelog.d/16320.doc b/changelog.d/16320.doc
new file mode 100644
index 0000000000..53e42df56f
--- /dev/null
+++ b/changelog.d/16320.doc
@@ -0,0 +1 @@
+Improve documentation of the user directory search algorithm.
diff --git a/changelog.d/16332.misc b/changelog.d/16332.misc
new file mode 100644
index 0000000000..862d547d60
--- /dev/null
+++ b/changelog.d/16332.misc
@@ -0,0 +1 @@
+Added support for pydantic v2 in addition to pydantic v1. Contributed by Maxwell G (@gotmax23).
diff --git a/changelog.d/16348.misc b/changelog.d/16348.misc
new file mode 100644
index 0000000000..846bb048c8
--- /dev/null
+++ b/changelog.d/16348.misc
@@ -0,0 +1 @@
+Get CI to check PRs have been signed-off.
diff --git a/changelog.d/16360.misc b/changelog.d/16360.misc
new file mode 100644
index 0000000000..b32d7b521e
--- /dev/null
+++ b/changelog.d/16360.misc
@@ -0,0 +1 @@
+Cache server ACL checking.
diff --git a/changelog.d/16361.feature b/changelog.d/16361.feature
new file mode 100644
index 0000000000..632fff789b
--- /dev/null
+++ b/changelog.d/16361.feature
@@ -0,0 +1 @@
+Experimental support for [MSC4028](https://github.com/matrix-org/matrix-spec-proposals/pull/4028) to push all encrypted events to clients.
diff --git a/changelog.d/16381.misc b/changelog.d/16381.misc
new file mode 100644
index 0000000000..a454651952
--- /dev/null
+++ b/changelog.d/16381.misc
@@ -0,0 +1 @@
+Improve type hints, and bump types-psycopg2 from 2.9.21.11 to 2.9.21.14.
diff --git a/changelog.d/16382.doc b/changelog.d/16382.doc
new file mode 100644
index 0000000000..2549586310
--- /dev/null
+++ b/changelog.d/16382.doc
@@ -0,0 +1 @@
+Update documentation around message retention policies.
diff --git a/changelog.d/16383.misc b/changelog.d/16383.misc
new file mode 100644
index 0000000000..d8d84cc184
--- /dev/null
+++ b/changelog.d/16383.misc
@@ -0,0 +1 @@
+Improve comments in `StateGroupBackgroundUpdateStore`.
diff --git a/changelog.d/16385.misc b/changelog.d/16385.misc
new file mode 100644
index 0000000000..d439a931d6
--- /dev/null
+++ b/changelog.d/16385.misc
@@ -0,0 +1 @@
+Minor performance improvement when sending presence to federated servers.
diff --git a/changelog.d/16387.misc b/changelog.d/16387.misc
new file mode 100644
index 0000000000..eae0501d6b
--- /dev/null
+++ b/changelog.d/16387.misc
@@ -0,0 +1 @@
+Avoid running CI steps when the files they check have not been changed.
\ No newline at end of file
diff --git a/changelog.d/16394.misc b/changelog.d/16394.misc
new file mode 100644
index 0000000000..ee08c3e024
--- /dev/null
+++ b/changelog.d/16394.misc
@@ -0,0 +1 @@
+Update maturin configuration.
diff --git a/changelog.d/16395.misc b/changelog.d/16395.misc
new file mode 100644
index 0000000000..93ceaeafc9
--- /dev/null
+++ b/changelog.d/16395.misc
@@ -0,0 +1 @@
+Improve type hints.
diff --git a/debian/changelog b/debian/changelog
index 192eedd45c..7be71019b4 100644
--- a/debian/changelog
+++ b/debian/changelog
@@ -1,3 +1,9 @@
+matrix-synapse-py3 (1.93.0) stable; urgency=medium
+
+  * New Synapse release 1.93.0.
+
+ -- Synapse Packaging team <packages@matrix.org>  Tue, 26 Sep 2023 15:54:40 +0100
+
 matrix-synapse-py3 (1.93.0~rc1) stable; urgency=medium
 
   * New synapse release 1.93.0rc1.
diff --git a/docs/development/database_schema.md b/docs/development/database_schema.md
index e231be21dd..675080ae1b 100644
--- a/docs/development/database_schema.md
+++ b/docs/development/database_schema.md
@@ -184,3 +184,160 @@ version `3`, that can only happen with a hash collision, which we basically hope
 will never happen (SHA256 has a massive big key space).
 
 
+## Worked examples of gradual migrations
+
+Some migrations need to be performed gradually. A prime example of this is anything
+which would need to do a large table scan — including adding columns, indices or
+`NOT NULL` constraints to non-empty tables — such a migration should be done as a
+background update where possible, at least on Postgres.
+We can afford to be more relaxed about SQLite databases since they are usually
+used on smaller deployments and SQLite does not support the same concurrent
+DDL operations as Postgres.
+
+We also typically insist on having at least one Synapse version's worth of
+backwards compatibility, so that administrators can roll back Synapse if an upgrade
+did not go smoothly.
+
+This sometimes results in having to plan a migration across multiple versions
+of Synapse.
+
+This section includes an example and may include more in the future.
+
+
+
+### Transforming a column into another one, with `NOT NULL` constraints
+
+This example illustrates how you would introduce a new column, write data into it
+based on data from an old column and then drop the old column.
+
+We are aiming for semantic equivalence to:
+
+```sql
+ALTER TABLE mytable ADD COLUMN new_column INTEGER;
+UPDATE mytable SET new_column = old_column * 100;
+ALTER TABLE mytable ALTER COLUMN new_column ADD CONSTRAINT NOT NULL;
+ALTER TABLE mytable DROP COLUMN old_column;
+```
+
+#### Synapse version `N`
+
+```python
+SCHEMA_VERSION = S
+SCHEMA_COMPAT_VERSION = ... # unimportant at this stage
+```
+
+**Invariants:**
+1. `old_column` is read by Synapse and written to by Synapse.
+
+
+#### Synapse version `N + 1`
+
+```python
+SCHEMA_VERSION = S + 1
+SCHEMA_COMPAT_VERSION = ... # unimportant at this stage
+```
+
+**Changes:**
+1.
+   ```sql
+   ALTER TABLE mytable ADD COLUMN new_column INTEGER;
+   ```
+
+**Invariants:**
+1. `old_column` is read by Synapse and written to by Synapse.
+2. `new_column` is written to by Synapse.
+
+**Notes:**
+1. `new_column` can't have a `NOT NULL NOT VALID` constraint yet, because the previous Synapse version did not write to the new column (since we haven't bumped the `SCHEMA_COMPAT_VERSION` yet, we still need to be compatible with the previous version).
+
+
+#### Synapse version `N + 2`
+
+```python
+SCHEMA_VERSION = S + 2
+SCHEMA_COMPAT_VERSION = S + 1 # this signals that we can't roll back to a time before new_column existed
+```
+
+**Changes:**
+1. On Postgres, add a `NOT VALID` constraint to ensure new rows are compliant. *SQLite does not have such a construct, but it would be unnecessary anyway since there is no way to concurrently perform this migration on SQLite.*
+   ```sql
+   ALTER TABLE mytable ADD CONSTRAINT CHECK new_column_not_null (new_column IS NOT NULL) NOT VALID;
+   ```
+2. Start a background update to perform migration: it should gradually run e.g.
+   ```sql
+   UPDATE mytable SET new_column = old_column * 100 WHERE 0 < mytable_id AND mytable_id <= 5;
+   ```
+   This background update is technically pointless on SQLite, but you must schedule it anyway so that the `portdb` script to migrate to Postgres still works.
+3. Upon completion of the background update, you should run `VALIDATE CONSTRAINT` on Postgres to turn the `NOT VALID` constraint into a valid one.
+   ```sql
+   ALTER TABLE mytable VALIDATE CONSTRAINT new_column_not_null;
+   ```
+   This will take some time but does **NOT** hold an exclusive lock over the table.
+
+**Invariants:**
+1. `old_column` is read by Synapse and written to by Synapse.
+2. `new_column` is written to by Synapse and new rows always have a non-`NULL` value in this field.
+
+
+**Notes:**
+1. If you wish, you can convert the `CHECK (new_column IS NOT NULL)` to a `NOT NULL` constraint free of charge in Postgres by adding the `NOT NULL` constraint and then dropping the `CHECK` constraint, because Postgres can statically verify that the `NOT NULL` constraint is implied by the `CHECK` constraint without performing a table scan.
+2. It might be tempting to make version `N + 2` redundant by moving the background update to `N + 1` and delaying adding the `NOT NULL` constraint to `N + 3`, but that would mean the constraint would always be validated in the foreground in `N + 3`. Whereas if the `N + 2` step is kept, the migration in `N + 3` would be fast in the happy case.
+
+#### Synapse version `N + 3`
+
+```python
+SCHEMA_VERSION = S + 3
+SCHEMA_COMPAT_VERSION = S + 1 # we can't roll back to a time before new_column existed
+```
+
+**Changes:**
+1. (Postgres) Update the table to populate values of `new_column` in case the background update had not completed. Additionally, `VALIDATE CONSTRAINT` to make the check fully valid.
+   ```sql
+   -- you ideally want an index on `new_column` or e.g. `(new_column) WHERE new_column IS NULL` first, or perhaps you can find a way to skip this if the `NOT NULL` constraint has already been validated.
+   UPDATE mytable SET new_column = old_column * 100 WHERE new_column IS NULL;
+
+   -- this is a no-op if it already ran as part of the background update
+   ALTER TABLE mytable VALIDATE CONSTRAINT new_column_not_null;
+   ```
+2. (SQLite) Recreate the table by precisely following [the 12-step procedure for SQLite table schema changes](https://www.sqlite.org/lang_altertable.html#otheralter).
+   During this table rewrite, you should recreate `new_column` as `NOT NULL` and populate any outstanding `NULL` values at the same time.
+   Unfortunately, you can't drop `old_column` yet because it must be present for compatibility with the Postgres schema, as needed by `portdb`.
+   (Otherwise you could do this all in one go with SQLite!)
+
+**Invariants:**
+1. `old_column` is written to by Synapse (but no longer read by Synapse!).
+2. `new_column` is read by Synapse and written to by Synapse. Moreover, all rows have a non-`NULL` value in this field, as guaranteed by a schema constraint.
+
+**Notes:**
+1. We can't drop `old_column` yet, or even stop writing to it, because that would break a rollback to the previous version of Synapse.
+2. Application code can now rely on `new_column` being populated. The remaining steps are only motivated by the wish to clean-up old columns.
+
+
+#### Synapse version `N + 4`
+
+```python
+SCHEMA_VERSION = S + 4
+SCHEMA_COMPAT_VERSION = S + 3 # we can't roll back to a time before new_column was entirely non-NULL
+```
+
+**Invariants:**
+1. `old_column` exists but is not written to or read from by Synapse.
+2. `new_column` is read by Synapse and written to by Synapse. Moreover, all rows have a non-`NULL` value in this field, as guaranteed by a schema constraint.
+
+**Notes:**
+1. We can't drop `old_column` yet because that would break a rollback to the previous version of Synapse. \
+   **TODO:** It may be possible to relax this and drop the column straight away as long as the previous version of Synapse detected a rollback occurred and stopped attempting to write to the column. This could possibly be done by checking whether the database's schema compatibility version was `S + 3`.
+
+
+#### Synapse version `N + 5`
+
+```python
+SCHEMA_VERSION = S + 5
+SCHEMA_COMPAT_VERSION = S + 4 # we can't roll back to a time before old_column was no longer being touched
+```
+
+**Changes:**
+1.
+   ```sql
+   ALTER TABLE mytable DROP COLUMN old_column;
+   ```
diff --git a/docs/message_retention_policies.md b/docs/message_retention_policies.md
index 7f3e5359f1..2746a106b3 100644
--- a/docs/message_retention_policies.md
+++ b/docs/message_retention_policies.md
@@ -8,8 +8,7 @@ and allow server and room admins to configure how long messages should
 be kept in a homeserver's database before being purged from it.
 **Please note that, as this feature isn't part of the Matrix
 specification yet, this implementation is to be considered as
-experimental. There are known bugs which may cause database corruption.
-Proceed with caution.** 
+experimental.**
 
 A message retention policy is mainly defined by its `max_lifetime`
 parameter, which defines how long a message can be kept around after
diff --git a/docs/usage/configuration/config_documentation.md b/docs/usage/configuration/config_documentation.md
index 54315a417e..502cd9f823 100644
--- a/docs/usage/configuration/config_documentation.md
+++ b/docs/usage/configuration/config_documentation.md
@@ -1026,11 +1026,8 @@ which are older than the room's maximum retention period. Synapse will also
 filter events received over federation so that events that should have been
 purged are ignored and not stored again.
 
-The message retention policies feature is disabled by default. Please be advised
-that enabling this feature carries some risk. There are known bugs with the implementation
-which can cause database corruption. Setting retention to delete older history
-is less risky than deleting newer history but in general caution is advised when enabling this
-experimental feature. You can read more about this feature [here](../../message_retention_policies.md).
+The message retention policies feature is disabled by default. You can read more
+about this feature [here](../../message_retention_policies.md).
 
 This setting has the following sub-options:
 * `default_policy`: Default retention policy. If set, Synapse will apply it to rooms that lack the
diff --git a/docs/user_directory.md b/docs/user_directory.md
index c4794b04cf..b33fd2bc2a 100644
--- a/docs/user_directory.md
+++ b/docs/user_directory.md
@@ -1,49 +1,133 @@
-User Directory API Implementation
-=================================
+# User Directory API Implementation
 
-The user directory is currently maintained based on the 'visible' users
-on this particular server - i.e. ones which your account shares a room with, or
-who are present in a publicly viewable room present on the server.
+The user directory is maintained based on users that are 'visible' to the homeserver -
+i.e. ones which are local to the server and ones which any local user shares a
+room with.
 
-The directory info is stored in various tables, which can (typically after
-DB corruption) get stale or out of sync. If this happens, for now the
+The directory info is stored in various tables, which can sometimes get out of
+sync (although this is considered a bug). If this happens, for now the
 solution to fix it is to use the [admin API](usage/administration/admin_api/background_updates.md#run)
 and execute the job `regenerate_directory`. This should then start a background task to
-flush the current tables and regenerate the directory.
+flush the current tables and regenerate the directory. Depending on the size
+of your homeserver (number of users and rooms) this can take a while.
 
-Data model
-----------
+## Data model
 
 There are five relevant tables that collectively form the "user directory".
-Three of them track a master list of all the users we could search for.
-The last two (collectively called the "search tables") track who can
-see who.
+Three of them track a list of all known users. The last two (collectively called
+the "search tables") track which users are visible to each other.
 
 From all of these tables we exclude three types of local user:
-  - support users
-  - appservice users
-  - deactivated users
-
-* `user_directory`. This contains the user_id, display name and avatar we'll
-  return when you search the directory.
-  - Because there's only one directory entry per user, it's important that we only
-    ever put publicly visible names here. Otherwise we might leak a private
+
+- support users
+- appservice users
+- deactivated users
+
+A description of each table follows:
+
+* `user_directory`. This contains the user ID, display name and avatar of each user.
+  - Because there is only one directory entry per user, it is important that it
+    only contain publicly visible information. Otherwise, this will leak the
     nickname or avatar used in a private room.
   - Indexed on rooms. Indexed on users.
 
 * `user_directory_search`. To be joined to `user_directory`. It contains an extra
-  column that enables full text search based on user ids and display names.
-  Different schemas for SQLite and Postgres with different code paths to match.
+  column that enables full text search based on user IDs and display names.
+  Different schemas for SQLite and Postgres are used.
   - Indexed on the full text search data. Indexed on users.
 
 * `user_directory_stream_pos`. When the initial background update to populate
   the directory is complete, we record a stream position here. This indicates
   that synapse should now listen for room changes and incrementally update
-  the directory where necessary.
+  the directory where necessary. (See [stream positions](development/synapse_architecture/streams.html).)
 
-* `users_in_public_rooms`. Contains associations between users and the public rooms they're in.
-  Used to determine which users are in public rooms and should be publicly visible in the directory.
+* `users_in_public_rooms`. Contains associations between users and the public
+  rooms they're in.  Used to determine which users are in public rooms and should
+  be publicly visible in the directory. Both local and remote users are tracked.
 
 * `users_who_share_private_rooms`. Rows are triples `(L, M, room id)` where `L`
    is a local user and `M` is a local or remote user. `L` and `M` should be
    different, but this isn't enforced by a constraint.
+
+   Note that if two local users share a room then there will be two entries:
+   `(user1, user2, !room_id)` and `(user2, user1, !room_id)`.
+
+## Configuration options
+
+The exact way user search works can be tweaked via some server-level
+[configuration options](usage/configuration/config_documentation.md#user_directory).
+
+The information is not repeated here, but the options are mentioned below.
+
+## Search algorithm
+
+If `search_all_users` is `false`, then results are limited to users who:
+
+1. Are found in the `users_in_public_rooms` table, or
+2. Are found in the `users_who_share_private_rooms` where `L` is the requesting
+   user and `M` is the search result.
+
+Otherwise, if `search_all_users` is `true`, no such limits are placed and all
+users known to the server (matching the search query) will be returned.
+
+By default, locked users are not returned. If `show_locked_users` is `true` then
+no filtering on the locked status of a user is done.
+
+The user provided search term is lowercased and normalized using [NFKC](https://en.wikipedia.org/wiki/Unicode_equivalence#Normalization),
+this treats the string as case-insensitive, canonicalizes different forms of the
+same text, and maps some "roughly equivalent" characters together.
+
+The search term is then split into words:
+
+* If [ICU](https://en.wikipedia.org/wiki/International_Components_for_Unicode) is
+  available, then the system's [default locale](https://unicode-org.github.io/icu/userguide/locale/#default-locales)
+  will be used to break the search term into words. (See the
+  [installation instructions](setup/installation.md) for how to install ICU.)
+* If unavailable, then runs of ASCII characters, numbers, underscores, and hypens
+  are considered words.
+
+The queries for PostgreSQL and SQLite are detailed below, by their overall goal
+is to find matching users, preferring users who are "real" (e.g. not bots,
+not deactivated). It is assumed that real users will have an display name and
+avatar set.
+
+### PostgreSQL
+
+The above words are then transformed into two queries:
+
+1. "exact" which matches the parsed words exactly (using [`to_tsquery`](https://www.postgresql.org/docs/current/textsearch-controls.html#TEXTSEARCH-PARSING-QUERIES));
+2. "prefix" which matches the parsed words as prefixes (using `to_tsquery`).
+
+Results are composed of all rows in the `user_directory_search` table whose information
+matches one (or both) of these queries. Results are ordered by calculating a weighted
+score for each result, higher scores are returned first:
+
+* 4x if a user ID exists.
+* 1.2x if the user has a display name set.
+* 1.2x if the user has an avatar set.
+* 0x-3x by the full text search results using the [`ts_rank_cd` function](https://www.postgresql.org/docs/current/textsearch-controls.html#TEXTSEARCH-RANKING)
+  against the "exact" search query; this has four variables with the following weightings:
+  * `D`: 0.1 for the user ID's domain
+  * `C`: 0.1 for unused
+  * `B`: 0.9 for the user's display name (or an empty string if it is not set)
+  * `A`: 0.1 for the user ID's localpart
+* 0x-1x by the full text search results using the `ts_rank_cd` function against the
+  "prefix" search query. (Using the same weightings as above.)
+* If `prefer_local_users` is `true`, then 2x if the user is local to the homeserver.
+
+Note that `ts_rank_cd` returns a weight between 0 and 1. The initial weighting of
+all results is 1.
+
+### SQLite
+
+Results are composed of all rows in the `user_directory_search` whose information
+matches the query. Results are ordered by the following information, with each
+subsequent column used as a tiebreaker, for each result:
+
+1. By the [`rank`](https://www.sqlite.org/windowfunctions.html#built_in_window_functions)
+   of the full text search results using the [`matchinfo` function](https://www.sqlite.org/fts3.html#matchinfo). Higher
+   ranks are returned first.
+2. If `prefer_local_users` is `true`, then users local to the homeserver are
+   returned first.
+3. Users with a display name set are returned first.
+4. Users with an avatar set are returned first.
diff --git a/poetry.lock b/poetry.lock
index e1b3733c45..bf229349cb 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -12,6 +12,20 @@ files = [
 ]
 
 [[package]]
+name = "annotated-types"
+version = "0.5.0"
+description = "Reusable constraint types to use with typing.Annotated"
+optional = false
+python-versions = ">=3.7"
+files = [
+    {file = "annotated_types-0.5.0-py3-none-any.whl", hash = "sha256:58da39888f92c276ad970249761ebea80ba544b77acddaa1a4d6cf78287d45fd"},
+    {file = "annotated_types-0.5.0.tar.gz", hash = "sha256:47cdc3490d9ac1506ce92c7aaa76c579dc3509ff11e098fc867e5130ab7be802"},
+]
+
+[package.dependencies]
+typing-extensions = {version = ">=4.0.0", markers = "python_version < \"3.9\""}
+
+[[package]]
 name = "astroid"
 version = "2.15.0"
 description = "An abstract syntax tree for Python with inference support."
@@ -457,34 +471,34 @@ files = [
 
 [[package]]
 name = "cryptography"
-version = "41.0.3"
+version = "41.0.4"
 description = "cryptography is a package which provides cryptographic recipes and primitives to Python developers."
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "cryptography-41.0.3-cp37-abi3-macosx_10_12_universal2.whl", hash = "sha256:652627a055cb52a84f8c448185922241dd5217443ca194d5739b44612c5e6507"},
-    {file = "cryptography-41.0.3-cp37-abi3-macosx_10_12_x86_64.whl", hash = "sha256:8f09daa483aedea50d249ef98ed500569841d6498aa9c9f4b0531b9964658922"},
-    {file = "cryptography-41.0.3-cp37-abi3-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:4fd871184321100fb400d759ad0cddddf284c4b696568204d281c902fc7b0d81"},
-    {file = "cryptography-41.0.3-cp37-abi3-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:84537453d57f55a50a5b6835622ee405816999a7113267739a1b4581f83535bd"},
-    {file = "cryptography-41.0.3-cp37-abi3-manylinux_2_28_aarch64.whl", hash = "sha256:3fb248989b6363906827284cd20cca63bb1a757e0a2864d4c1682a985e3dca47"},
-    {file = "cryptography-41.0.3-cp37-abi3-manylinux_2_28_x86_64.whl", hash = "sha256:42cb413e01a5d36da9929baa9d70ca90d90b969269e5a12d39c1e0d475010116"},
-    {file = "cryptography-41.0.3-cp37-abi3-musllinux_1_1_aarch64.whl", hash = "sha256:aeb57c421b34af8f9fe830e1955bf493a86a7996cc1338fe41b30047d16e962c"},
-    {file = "cryptography-41.0.3-cp37-abi3-musllinux_1_1_x86_64.whl", hash = "sha256:6af1c6387c531cd364b72c28daa29232162010d952ceb7e5ca8e2827526aceae"},
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 [package.dependencies]
 gitdb = ">=4.0.1,<5"
 
+[package.extras]
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+
 [[package]]
 name = "hiredis"
 version = "2.2.3"
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+]
+
+[package.dependencies]
+typing-extensions = ">=4.6.0,<4.7.0 || >4.7.0"
 
 [[package]]
 name = "pygithub"
@@ -2075,7 +2170,6 @@ files = [
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     {file = "PyYAML-6.0.1-cp310-cp310-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:ba336e390cd8e4d1739f42dfe9bb83a3cc2e80f567d8805e11b46f4a943f5515"},
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@@ -2083,15 +2177,8 @@ files = [
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     {file = "PyYAML-6.0.1-cp36-cp36m-manylinux_2_17_s390x.manylinux2014_s390x.whl", hash = "sha256:704219a11b772aea0d8ecd7058d0082713c3562b4e271b849ad7dc4a5c90c13c"},
@@ -2108,7 +2195,6 @@ files = [
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     {file = "PyYAML-6.0.1-cp38-cp38-win32.whl", hash = "sha256:184c5108a2aca3c5b3d3bf9395d50893a7ab82a38004c8f61c258d4428e80206"},
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@@ -2116,7 +2202,6 @@ files = [
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     {file = "PyYAML-6.0.1.tar.gz", hash = "sha256:bfdf460b1736c775f2ba9f6a92bca30bc2095067b8a9d77876d1fad6cc3b4a43"},
@@ -2388,13 +2473,13 @@ doc = ["Sphinx", "sphinx-rtd-theme"]
 
 [[package]]
 name = "sentry-sdk"
-version = "1.30.0"
+version = "1.31.0"
 description = "Python client for Sentry (https://sentry.io)"
 optional = true
 python-versions = "*"
 files = [
-    {file = "sentry-sdk-1.30.0.tar.gz", hash = "sha256:7dc873b87e1faf4d00614afd1058bfa1522942f33daef8a59f90de8ed75cd10c"},
-    {file = "sentry_sdk-1.30.0-py2.py3-none-any.whl", hash = "sha256:2e53ad63f96bb9da6570ba2e755c267e529edcf58580a2c0d2a11ef26e1e678b"},
+    {file = "sentry-sdk-1.31.0.tar.gz", hash = "sha256:6de2e88304873484207fed836388e422aeff000609b104c802749fd89d56ba5b"},
+    {file = "sentry_sdk-1.31.0-py2.py3-none-any.whl", hash = "sha256:64a7141005fb775b9db298a30de93e3b83e0ddd1232dc6f36eb38aebc1553291"},
 ]
 
 [package.dependencies]
@@ -2404,10 +2489,12 @@ urllib3 = {version = ">=1.26.11", markers = "python_version >= \"3.6\""}
 [package.extras]
 aiohttp = ["aiohttp (>=3.5)"]
 arq = ["arq (>=0.23)"]
+asyncpg = ["asyncpg (>=0.23)"]
 beam = ["apache-beam (>=2.12)"]
 bottle = ["bottle (>=0.12.13)"]
 celery = ["celery (>=3)"]
 chalice = ["chalice (>=1.16.0)"]
+clickhouse-driver = ["clickhouse-driver (>=0.2.0)"]
 django = ["django (>=1.8)"]
 falcon = ["falcon (>=1.4)"]
 fastapi = ["fastapi (>=0.79.0)"]
@@ -3006,13 +3093,13 @@ files = [
 
 [[package]]
 name = "types-psycopg2"
-version = "2.9.21.11"
+version = "2.9.21.14"
 description = "Typing stubs for psycopg2"
 optional = false
 python-versions = "*"
 files = [
-    {file = "types-psycopg2-2.9.21.11.tar.gz", hash = "sha256:d5077eacf90e61db8c0b8eea2fdc9d4a97d7aaa16865fb4bd7034a7571520b4d"},
-    {file = "types_psycopg2-2.9.21.11-py3-none-any.whl", hash = "sha256:7a323d7744bc8a882fb5a6f63448e903fc70d3dc0d6da9ec1f9c6c4dc10a7102"},
+    {file = "types-psycopg2-2.9.21.14.tar.gz", hash = "sha256:bf73a0ac4da4e278c89bf1b01fc596d5a5ac7a356cfe6ac0249f47b9e259f868"},
+    {file = "types_psycopg2-2.9.21.14-py3-none-any.whl", hash = "sha256:cd9c5350631f3bc6184ec8d48f2ed31d4ea660f89d0fffe78239450782f383c5"},
 ]
 
 [[package]]
@@ -3347,4 +3434,4 @@ user-search = ["pyicu"]
 [metadata]
 lock-version = "2.0"
 python-versions = "^3.8.0"
-content-hash = "104f108b3c966be05e17cf9975b4061942b354fe9a57cbf7372371fd56b1bf24"
+content-hash = "364c309486e9d93d4da8a1a3784d5ecd7d2a9734cf84dcd4a991f2cd54f0b5b5"
diff --git a/pyproject.toml b/pyproject.toml
index f69336a73f..5fb64479a1 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -92,10 +92,11 @@ skip_gitignore = true
 
 [tool.maturin]
 manifest-path = "rust/Cargo.toml"
+module-name = "synapse.synapse_rust"
 
 [tool.poetry]
 name = "matrix-synapse"
-version = "1.93.0rc1"
+version = "1.93.0"
 description = "Homeserver for the Matrix decentralised comms protocol"
 authors = ["Matrix.org Team and Contributors <packages@matrix.org>"]
 license = "Apache-2.0"
@@ -209,11 +210,11 @@ cryptography = ">=3.4.7"
 # ijson 3.1.4 fixes a bug with "." in property names
 ijson = ">=3.1.4"
 matrix-common = "^1.3.0"
-# We need packaging.requirements.Requirement, added in 16.1.
-packaging = ">=16.1"
-# This is the most recent version of Pydantic with available on common distros.
-# We are currently incompatible with >=2.0.0: (https://github.com/matrix-org/synapse/issues/15858)
-pydantic = "^1.7.4"
+# 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"
 
 # This is for building the rust components during "poetry install", which
 # currently ignores the `build-system.requires` directive (c.f.
@@ -321,6 +322,8 @@ all = [
 isort = ">=5.10.1"
 black = ">=22.7.0"
 ruff = "0.0.290"
+# Type checking only works with the pydantic.v1 compat module from pydantic v2
+pydantic = "^2"
 
 # Typechecking
 lxml-stubs = ">=0.4.0"
diff --git a/rust/Cargo.toml b/rust/Cargo.toml
index 16917136db..26403d58cc 100644
--- a/rust/Cargo.toml
+++ b/rust/Cargo.toml
@@ -15,6 +15,8 @@ name = "synapse"
 # tests/benchmarks.
 crate-type = ["lib", "cdylib"]
 
+# This is deprecated, see tool.maturin in pyproject.toml.
+# It is left here for compatibilty with maturin < 0.15.
 [package.metadata.maturin]
 # This is where we tell maturin where to place the built library.
 name = "synapse.synapse_rust"
diff --git a/rust/benches/evaluator.rs b/rust/benches/evaluator.rs
index 14071105a0..6e1eab2a3b 100644
--- a/rust/benches/evaluator.rs
+++ b/rust/benches/evaluator.rs
@@ -197,6 +197,7 @@ fn bench_eval_message(b: &mut Bencher) {
         false,
         false,
         false,
+        false,
     );
 
     b.iter(|| eval.run(&rules, Some("bob"), Some("person")));
diff --git a/rust/src/acl/mod.rs b/rust/src/acl/mod.rs
new file mode 100644
index 0000000000..071f2b7732
--- /dev/null
+++ b/rust/src/acl/mod.rs
@@ -0,0 +1,102 @@
+// Copyright 2023 The Matrix.org Foundation C.I.C.
+//
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+//! An implementation of Matrix server ACL rules.
+
+use std::net::Ipv4Addr;
+use std::str::FromStr;
+
+use anyhow::Error;
+use pyo3::prelude::*;
+use regex::Regex;
+
+use crate::push::utils::{glob_to_regex, GlobMatchType};
+
+/// Called when registering modules with python.
+pub fn register_module(py: Python<'_>, m: &PyModule) -> PyResult<()> {
+    let child_module = PyModule::new(py, "acl")?;
+    child_module.add_class::<ServerAclEvaluator>()?;
+
+    m.add_submodule(child_module)?;
+
+    // We need to manually add the module to sys.modules to make `from
+    // synapse.synapse_rust import acl` work.
+    py.import("sys")?
+        .getattr("modules")?
+        .set_item("synapse.synapse_rust.acl", child_module)?;
+
+    Ok(())
+}
+
+#[derive(Debug, Clone)]
+#[pyclass(frozen)]
+pub struct ServerAclEvaluator {
+    allow_ip_literals: bool,
+    allow: Vec<Regex>,
+    deny: Vec<Regex>,
+}
+
+#[pymethods]
+impl ServerAclEvaluator {
+    #[new]
+    pub fn py_new(
+        allow_ip_literals: bool,
+        allow: Vec<&str>,
+        deny: Vec<&str>,
+    ) -> Result<Self, Error> {
+        let allow = allow
+            .iter()
+            .map(|s| glob_to_regex(s, GlobMatchType::Whole))
+            .collect::<Result<_, _>>()?;
+        let deny = deny
+            .iter()
+            .map(|s| glob_to_regex(s, GlobMatchType::Whole))
+            .collect::<Result<_, _>>()?;
+
+        Ok(ServerAclEvaluator {
+            allow_ip_literals,
+            allow,
+            deny,
+        })
+    }
+
+    pub fn server_matches_acl_event(&self, server_name: &str) -> bool {
+        // first of all, check if literal IPs are blocked, and if so, whether the
+        // server name is a literal IP
+        if !self.allow_ip_literals {
+            // check for ipv6 literals. These start with '['.
+            if server_name.starts_with('[') {
+                return false;
+            }
+
+            // check for ipv4 literals. We can just lift the routine from std::net.
+            if Ipv4Addr::from_str(server_name).is_ok() {
+                return false;
+            }
+        }
+
+        // next, check the deny list
+        if self.deny.iter().any(|e| e.is_match(server_name)) {
+            return false;
+        }
+
+        // then the allow list.
+        if self.allow.iter().any(|e| e.is_match(server_name)) {
+            return true;
+        }
+
+        // everything else should be rejected.
+        false
+    }
+}
diff --git a/rust/src/lib.rs b/rust/src/lib.rs
index ce67f58611..c44c09bda7 100644
--- a/rust/src/lib.rs
+++ b/rust/src/lib.rs
@@ -2,6 +2,7 @@ use lazy_static::lazy_static;
 use pyo3::prelude::*;
 use pyo3_log::ResetHandle;
 
+pub mod acl;
 pub mod push;
 
 lazy_static! {
@@ -38,6 +39,7 @@ fn synapse_rust(py: Python<'_>, m: &PyModule) -> PyResult<()> {
     m.add_function(wrap_pyfunction!(get_rust_file_digest, m)?)?;
     m.add_function(wrap_pyfunction!(reset_logging_config, m)?)?;
 
+    acl::register_module(py, m)?;
     push::register_module(py, m)?;
 
     Ok(())
diff --git a/rust/src/push/base_rules.rs b/rust/src/push/base_rules.rs
index 59fd27665a..cebc2c079b 100644
--- a/rust/src/push/base_rules.rs
+++ b/rust/src/push/base_rules.rs
@@ -64,6 +64,19 @@ pub const BASE_PREPEND_OVERRIDE_RULES: &[PushRule] = &[PushRule {
 
 pub const BASE_APPEND_OVERRIDE_RULES: &[PushRule] = &[
     PushRule {
+        rule_id: Cow::Borrowed("global/override/.org.matrix.msc4028.encrypted_event"),
+        priority_class: 5,
+        conditions: Cow::Borrowed(&[Condition::Known(KnownCondition::EventMatch(
+            EventMatchCondition {
+                key: Cow::Borrowed("type"),
+                pattern: Cow::Borrowed("m.room.encrypted"),
+            },
+        ))]),
+        actions: Cow::Borrowed(&[Action::Notify]),
+        default: true,
+        default_enabled: false,
+    },
+    PushRule {
         rule_id: Cow::Borrowed("global/override/.m.rule.suppress_notices"),
         priority_class: 5,
         conditions: Cow::Borrowed(&[Condition::Known(KnownCondition::EventMatch(
diff --git a/rust/src/push/evaluator.rs b/rust/src/push/evaluator.rs
index 5b9bf9b26a..48e670478b 100644
--- a/rust/src/push/evaluator.rs
+++ b/rust/src/push/evaluator.rs
@@ -564,7 +564,7 @@ fn test_requires_room_version_supports_condition() {
     };
     let rules = PushRules::new(vec![custom_rule]);
     result = evaluator.run(
-        &FilteredPushRules::py_new(rules, BTreeMap::new(), true, false, true),
+        &FilteredPushRules::py_new(rules, BTreeMap::new(), true, false, true, false),
         None,
         None,
     );
diff --git a/rust/src/push/mod.rs b/rust/src/push/mod.rs
index 8e91f506cc..5e1e8e1abb 100644
--- a/rust/src/push/mod.rs
+++ b/rust/src/push/mod.rs
@@ -527,6 +527,7 @@ pub struct FilteredPushRules {
     msc1767_enabled: bool,
     msc3381_polls_enabled: bool,
     msc3664_enabled: bool,
+    msc4028_push_encrypted_events: bool,
 }
 
 #[pymethods]
@@ -538,6 +539,7 @@ impl FilteredPushRules {
         msc1767_enabled: bool,
         msc3381_polls_enabled: bool,
         msc3664_enabled: bool,
+        msc4028_push_encrypted_events: bool,
     ) -> Self {
         Self {
             push_rules,
@@ -545,6 +547,7 @@ impl FilteredPushRules {
             msc1767_enabled,
             msc3381_polls_enabled,
             msc3664_enabled,
+            msc4028_push_encrypted_events,
         }
     }
 
@@ -581,6 +584,12 @@ impl FilteredPushRules {
                     return false;
                 }
 
+                if !self.msc4028_push_encrypted_events
+                    && rule.rule_id == "global/override/.org.matrix.msc4028.encrypted_event"
+                {
+                    return false;
+                }
+
                 true
             })
             .map(|r| {
diff --git a/scripts-dev/check_pydantic_models.py b/scripts-dev/check_pydantic_models.py
index 9f2b7ded5b..d1cfc9a85c 100755
--- a/scripts-dev/check_pydantic_models.py
+++ b/scripts-dev/check_pydantic_models.py
@@ -36,11 +36,41 @@ import textwrap
 import traceback
 import unittest.mock
 from contextlib import contextmanager
-from typing import Any, Callable, Dict, Generator, List, Set, Type, TypeVar
+from typing import (
+    TYPE_CHECKING,
+    Any,
+    Callable,
+    Dict,
+    Generator,
+    List,
+    Set,
+    Type,
+    TypeVar,
+)
 
 from parameterized import parameterized
-from pydantic import BaseModel as PydanticBaseModel, conbytes, confloat, conint, constr
-from pydantic.typing import get_args
+
+from synapse._pydantic_compat import HAS_PYDANTIC_V2
+
+if TYPE_CHECKING or HAS_PYDANTIC_V2:
+    from pydantic.v1 import (
+        BaseModel as PydanticBaseModel,
+        conbytes,
+        confloat,
+        conint,
+        constr,
+    )
+    from pydantic.v1.typing import get_args
+else:
+    from pydantic import (
+        BaseModel as PydanticBaseModel,
+        conbytes,
+        confloat,
+        conint,
+        constr,
+    )
+    from pydantic.typing import get_args
+
 from typing_extensions import ParamSpec
 
 logger = logging.getLogger(__name__)
@@ -251,7 +281,10 @@ class TestConstrainedTypesPatch(unittest.TestCase):
         with monkeypatch_pydantic(), self.assertRaises(ModelCheckerException):
             run_test_snippet(
                 """
-                from pydantic import constr
+                try:
+                    from pydantic.v1 import constr
+                except ImportError:
+                    from pydantic import constr
                 constr()
                 """
             )
@@ -269,7 +302,10 @@ class TestConstrainedTypesPatch(unittest.TestCase):
         with monkeypatch_pydantic(), self.assertRaises(ModelCheckerException):
             run_test_snippet(
                 """
-                from pydantic import *
+                try:
+                    from pydantic.v1 import *
+                except ImportError:
+                    from pydantic import *
                 constr()
                 """
             )
@@ -278,7 +314,10 @@ class TestConstrainedTypesPatch(unittest.TestCase):
         with monkeypatch_pydantic(), self.assertRaises(ModelCheckerException):
             run_test_snippet(
                 """
-                from pydantic.types import constr
+                try:
+                    from pydantic.v1.types import constr
+                except ImportError:
+                    from pydantic.types import constr
                 constr()
                 """
             )
@@ -287,8 +326,11 @@ class TestConstrainedTypesPatch(unittest.TestCase):
         with monkeypatch_pydantic(), self.assertRaises(ModelCheckerException):
             run_test_snippet(
                 """
-                import pydantic.types
-                pydantic.types.constr()
+                try:
+                    from pydantic.v1 import types as pydantic_types
+                except ImportError:
+                    from pydantic import types as pydantic_types
+                pydantic_types.constr()
                 """
             )
 
@@ -296,7 +338,10 @@ class TestConstrainedTypesPatch(unittest.TestCase):
         with monkeypatch_pydantic(), self.assertRaises(ModelCheckerException):
             run_test_snippet(
                 """
-                from pydantic import constr
+                try:
+                    from pydantic.v1 import constr
+                except ImportError:
+                    from pydantic import constr
                 constr(min_length=10)
                 """
             )
@@ -305,7 +350,10 @@ class TestConstrainedTypesPatch(unittest.TestCase):
         with monkeypatch_pydantic(), self.assertRaises(ModelCheckerException):
             run_test_snippet(
                 """
-                from pydantic import constr
+                try:
+                    from pydantic.v1 import constr
+                except ImportError:
+                    from pydantic import constr
                 constr(strict=False)
                 """
             )
@@ -314,7 +362,10 @@ class TestConstrainedTypesPatch(unittest.TestCase):
         with monkeypatch_pydantic():
             run_test_snippet(
                 """
-                from pydantic import constr
+                try:
+                    from pydantic.v1 import constr
+                except ImportError:
+                    from pydantic import constr
                 constr(strict=True)
                 """
             )
@@ -323,7 +374,10 @@ class TestConstrainedTypesPatch(unittest.TestCase):
         with monkeypatch_pydantic(), self.assertRaises(ModelCheckerException):
             run_test_snippet(
                 """
-                from pydantic import constr
+                try:
+                    from pydantic.v1 import constr
+                except ImportError:
+                    from pydantic import constr
                 x: constr()
                 """
             )
@@ -332,7 +386,10 @@ class TestConstrainedTypesPatch(unittest.TestCase):
         with monkeypatch_pydantic(), self.assertRaises(ModelCheckerException):
             run_test_snippet(
                 """
-                from pydantic import BaseModel, conint
+                try:
+                    from pydantic.v1 import BaseModel, conint
+                except ImportError:
+                    from pydantic import BaseModel, conint
                 class C:
                     x: conint()
                 """
@@ -361,7 +418,10 @@ class TestFieldTypeInspection(unittest.TestCase):
             run_test_snippet(
                 f"""
                 from typing import *
-                from pydantic import *
+                try:
+                    from pydantic.v1 import *
+                except ImportError:
+                    from pydantic import *
                 class C(BaseModel):
                     f: {annotation}
                 """
@@ -388,7 +448,10 @@ class TestFieldTypeInspection(unittest.TestCase):
             run_test_snippet(
                 f"""
                 from typing import *
-                from pydantic import *
+                try:
+                    from pydantic.v1 import *
+                except ImportError:
+                    from pydantic import *
                 class C(BaseModel):
                     f: {annotation}
                 """
@@ -398,7 +461,10 @@ class TestFieldTypeInspection(unittest.TestCase):
         with monkeypatch_pydantic(), self.assertRaises(ModelCheckerException):
             run_test_snippet(
                 """
-                from pydantic.main import BaseModel
+                try:
+                    from pydantic.v1.main import BaseModel
+                except ImportError:
+                    from pydantic.main import BaseModel
                 class C(BaseModel):
                     f: str
                 """
diff --git a/stubs/synapse/synapse_rust/acl.pyi b/stubs/synapse/synapse_rust/acl.pyi
new file mode 100644
index 0000000000..e03989b627
--- /dev/null
+++ b/stubs/synapse/synapse_rust/acl.pyi
@@ -0,0 +1,21 @@
+# Copyright 2023 The Matrix.org Foundation C.I.C.
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# 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]
+    ) -> None: ...
+    def server_matches_acl_event(self, server_name: str) -> bool: ...
diff --git a/stubs/synapse/synapse_rust/push.pyi b/stubs/synapse/synapse_rust/push.pyi
index 1f432d4ecf..25259ce91d 100644
--- a/stubs/synapse/synapse_rust/push.pyi
+++ b/stubs/synapse/synapse_rust/push.pyi
@@ -46,6 +46,7 @@ class FilteredPushRules:
         msc1767_enabled: bool,
         msc3381_polls_enabled: bool,
         msc3664_enabled: bool,
+        msc4028_push_encrypted_events: bool,
     ): ...
     def rules(self) -> Collection[Tuple[PushRule, bool]]: ...
 
diff --git a/synapse/_pydantic_compat.py b/synapse/_pydantic_compat.py
new file mode 100644
index 0000000000..ddff72afa1
--- /dev/null
+++ b/synapse/_pydantic_compat.py
@@ -0,0 +1,26 @@
+# Copyright 2023 Maxwell G <maxwell@gtmx.me>
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+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
+
+__all__ = ("HAS_PYDANTIC_V2",)
diff --git a/synapse/config/_util.py b/synapse/config/_util.py
index acccca413b..746838eee3 100644
--- a/synapse/config/_util.py
+++ b/synapse/config/_util.py
@@ -11,10 +11,16 @@
 # WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
 # See the License for the specific language governing permissions and
 # limitations under the License.
-from typing import Any, Dict, Type, TypeVar
+from typing import TYPE_CHECKING, Any, Dict, Type, TypeVar
 
 import jsonschema
-from pydantic import BaseModel, ValidationError, parse_obj_as
+
+from synapse._pydantic_compat import HAS_PYDANTIC_V2
+
+if TYPE_CHECKING or HAS_PYDANTIC_V2:
+    from pydantic.v1 import BaseModel, ValidationError, parse_obj_as
+else:
+    from pydantic import BaseModel, ValidationError, parse_obj_as
 
 from synapse.config._base import ConfigError
 from synapse.types import JsonDict, StrSequence
diff --git a/synapse/config/experimental.py b/synapse/config/experimental.py
index cabe0d4397..9f830e7094 100644
--- a/synapse/config/experimental.py
+++ b/synapse/config/experimental.py
@@ -415,3 +415,7 @@ class ExperimentalConfig(Config):
         LimitExceededError.include_retry_after_header = experimental.get(
             "msc4041_enabled", False
         )
+
+        self.msc4028_push_encrypted_events = experimental.get(
+            "msc4028_push_encrypted_events", False
+        )
diff --git a/synapse/config/workers.py b/synapse/config/workers.py
index 6567fb6bb0..f1766088fc 100644
--- a/synapse/config/workers.py
+++ b/synapse/config/workers.py
@@ -15,10 +15,16 @@
 
 import argparse
 import logging
-from typing import Any, Dict, List, Optional, Union
+from typing import TYPE_CHECKING, Any, Dict, List, Optional, Union
 
 import attr
-from pydantic import BaseModel, Extra, StrictBool, StrictInt, StrictStr
+
+from synapse._pydantic_compat import HAS_PYDANTIC_V2
+
+if TYPE_CHECKING or HAS_PYDANTIC_V2:
+    from pydantic.v1 import BaseModel, Extra, StrictBool, StrictInt, StrictStr
+else:
+    from pydantic import BaseModel, Extra, StrictBool, StrictInt, StrictStr
 
 from synapse.config._base import (
     Config,
diff --git a/synapse/events/validator.py b/synapse/events/validator.py
index 5da50cb0d2..83d9fb5813 100644
--- a/synapse/events/validator.py
+++ b/synapse/events/validator.py
@@ -12,10 +12,16 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 import collections.abc
-from typing import List, Type, Union, cast
+from typing import TYPE_CHECKING, List, Type, Union, cast
 
 import jsonschema
-from pydantic import Field, StrictBool, StrictStr
+
+from synapse._pydantic_compat import HAS_PYDANTIC_V2
+
+if TYPE_CHECKING or HAS_PYDANTIC_V2:
+    from pydantic.v1 import Field, StrictBool, StrictStr
+else:
+    from pydantic import Field, StrictBool, StrictStr
 
 from synapse.api.constants import (
     MAX_ALIAS_LENGTH,
@@ -33,9 +39,9 @@ from synapse.events.utils import (
     CANONICALJSON_MIN_INT,
     validate_canonicaljson,
 )
-from synapse.federation.federation_server import server_matches_acl_event
 from synapse.http.servlet import validate_json_object
 from synapse.rest.models import RequestBodyModel
+from synapse.storage.controllers.state import server_acl_evaluator_from_event
 from synapse.types import EventID, JsonDict, RoomID, StrCollection, UserID
 
 
@@ -100,7 +106,10 @@ class EventValidator:
             self._validate_retention(event)
 
         elif event.type == EventTypes.ServerACL:
-            if not server_matches_acl_event(config.server.server_name, event):
+            server_acl_evaluator = server_acl_evaluator_from_event(event)
+            if not server_acl_evaluator.server_matches_acl_event(
+                config.server.server_name
+            ):
                 raise SynapseError(
                     400, "Can't create an ACL event that denies the local server"
                 )
diff --git a/synapse/federation/federation_server.py b/synapse/federation/federation_server.py
index f9915e5a3f..ec8e770430 100644
--- a/synapse/federation/federation_server.py
+++ b/synapse/federation/federation_server.py
@@ -29,10 +29,8 @@ from typing import (
     Union,
 )
 
-from matrix_common.regex import glob_to_regex
 from prometheus_client import Counter, Gauge, Histogram
 
-from twisted.internet.abstract import isIPAddress
 from twisted.python import failure
 
 from synapse.api.constants import (
@@ -1324,75 +1322,13 @@ class FederationServer(FederationBase):
         Raises:
             AuthError if the server does not match the ACL
         """
-        acl_event = await self._storage_controllers.state.get_current_state_event(
-            room_id, EventTypes.ServerACL, ""
+        server_acl_evaluator = (
+            await self._storage_controllers.state.get_server_acl_for_room(room_id)
         )
-        if not acl_event or server_matches_acl_event(server_name, acl_event):
-            return
-
-        raise AuthError(code=403, msg="Server is banned from room")
-
-
-def server_matches_acl_event(server_name: str, acl_event: EventBase) -> bool:
-    """Check if the given server is allowed by the ACL event
-
-    Args:
-        server_name: name of server, without any port part
-        acl_event: m.room.server_acl event
-
-    Returns:
-        True if this server is allowed by the ACLs
-    """
-    logger.debug("Checking %s against acl %s", server_name, acl_event.content)
-
-    # first of all, check if literal IPs are blocked, and if so, whether the
-    # server name is a literal IP
-    allow_ip_literals = acl_event.content.get("allow_ip_literals", True)
-    if not isinstance(allow_ip_literals, bool):
-        logger.warning("Ignoring non-bool allow_ip_literals flag")
-        allow_ip_literals = True
-    if not allow_ip_literals:
-        # check for ipv6 literals. These start with '['.
-        if server_name[0] == "[":
-            return False
-
-        # check for ipv4 literals. We can just lift the routine from twisted.
-        if isIPAddress(server_name):
-            return False
-
-    # next,  check the deny list
-    deny = acl_event.content.get("deny", [])
-    if not isinstance(deny, (list, tuple)):
-        logger.warning("Ignoring non-list deny ACL %s", deny)
-        deny = []
-    for e in deny:
-        if _acl_entry_matches(server_name, e):
-            # logger.info("%s matched deny rule %s", server_name, e)
-            return False
-
-    # then the allow list.
-    allow = acl_event.content.get("allow", [])
-    if not isinstance(allow, (list, tuple)):
-        logger.warning("Ignoring non-list allow ACL %s", allow)
-        allow = []
-    for e in allow:
-        if _acl_entry_matches(server_name, e):
-            # logger.info("%s matched allow rule %s", server_name, e)
-            return True
-
-    # everything else should be rejected.
-    # logger.info("%s fell through", server_name)
-    return False
-
-
-def _acl_entry_matches(server_name: str, acl_entry: Any) -> bool:
-    if not isinstance(acl_entry, str):
-        logger.warning(
-            "Ignoring non-str ACL entry '%s' (is %s)", acl_entry, type(acl_entry)
-        )
-        return False
-    regex = glob_to_regex(acl_entry)
-    return bool(regex.match(server_name))
+        if server_acl_evaluator and not server_acl_evaluator.server_matches_acl_event(
+            server_name
+        ):
+            raise AuthError(code=403, msg="Server is banned from room")
 
 
 class FederationHandlerRegistry:
diff --git a/synapse/handlers/federation_event.py b/synapse/handlers/federation_event.py
index 7c62cdfaef..0cc8e990d9 100644
--- a/synapse/handlers/federation_event.py
+++ b/synapse/handlers/federation_event.py
@@ -2342,6 +2342,12 @@ class FederationEventHandler:
             # TODO retrieve the previous state, and exclude join -> join transitions
             self._notifier.notify_user_joined_room(event.event_id, event.room_id)
 
+        # If this is a server ACL event, clear the cache in the storage controller.
+        if event.type == EventTypes.ServerACL:
+            self._state_storage_controller.get_server_acl_for_room.invalidate(
+                (event.room_id,)
+            )
+
     def _sanity_check_event(self, ev: EventBase) -> None:
         """
         Do some early sanity checks of a received event
diff --git a/synapse/handlers/message.py b/synapse/handlers/message.py
index c036578a3d..44dbbf81dd 100644
--- a/synapse/handlers/message.py
+++ b/synapse/handlers/message.py
@@ -1730,6 +1730,11 @@ class EventCreationHandler:
                         event.event_id, event.room_id
                     )
 
+            if event.type == EventTypes.ServerACL:
+                self._storage_controllers.state.get_server_acl_for_room.invalidate(
+                    (event.room_id,)
+                )
+
             await self._maybe_kick_guest_users(event, context)
 
             if event.type == EventTypes.CanonicalAlias:
diff --git a/synapse/handlers/presence.py b/synapse/handlers/presence.py
index 375c7d0901..7c7cda3e95 100644
--- a/synapse/handlers/presence.py
+++ b/synapse/handlers/presence.py
@@ -401,9 +401,9 @@ class BasePresenceHandler(abc.ABC):
             states,
         )
 
-        for destination, host_states in hosts_to_states.items():
+        for destinations, host_states in hosts_to_states:
             await self._federation.send_presence_to_destinations(
-                host_states, [destination]
+                host_states, destinations
             )
 
     async def send_full_presence_to_users(self, user_ids: StrCollection) -> None:
@@ -1000,9 +1000,9 @@ class PresenceHandler(BasePresenceHandler):
                     list(to_federation_ping.values()),
                 )
 
-                for destination, states in hosts_to_states.items():
+                for destinations, states in hosts_to_states:
                     await self._federation_queue.send_presence_to_destinations(
-                        states, [destination]
+                        states, destinations
                     )
 
     @wrap_as_background_process("handle_presence_timeouts")
@@ -2276,7 +2276,7 @@ async def get_interested_remotes(
     store: DataStore,
     presence_router: PresenceRouter,
     states: List[UserPresenceState],
-) -> Dict[str, Set[UserPresenceState]]:
+) -> List[Tuple[StrCollection, Collection[UserPresenceState]]]:
     """Given a list of presence states figure out which remote servers
     should be sent which.
 
@@ -2290,23 +2290,26 @@ async def get_interested_remotes(
     Returns:
         A map from destinations to presence states to send to that destination.
     """
-    hosts_and_states: Dict[str, Set[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.
-    room_ids_to_states, users_to_states = await get_interested_parties(
-        store, presence_router, states
-    )
+    for state in states:
+        room_ids = await store.get_rooms_for_user(state.user_id)
+        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)
+        hosts_and_states.append((hosts, [state]))
 
-    for room_id, states in room_ids_to_states.items():
-        hosts = await store.get_current_hosts_in_room(room_id)
-        for host in hosts:
-            hosts_and_states.setdefault(host, set()).update(states)
+    # Ask a presence routing module for any additional parties if one
+    # is loaded.
+    router_users_to_states = await presence_router.get_users_for_states(states)
 
-    for user_id, states in users_to_states.items():
+    for user_id, user_states in router_users_to_states.items():
         host = get_domain_from_id(user_id)
-        hosts_and_states.setdefault(host, set()).update(states)
+        hosts_and_states.append(([host], user_states))
 
     return hosts_and_states
 
diff --git a/synapse/http/servlet.py b/synapse/http/servlet.py
index 5d79d31579..d9d5655c95 100644
--- a/synapse/http/servlet.py
+++ b/synapse/http/servlet.py
@@ -28,8 +28,15 @@ from typing import (
     overload,
 )
 
-from pydantic import BaseModel, MissingError, PydanticValueError, ValidationError
-from pydantic.error_wrappers import ErrorWrapper
+from synapse._pydantic_compat import HAS_PYDANTIC_V2
+
+if TYPE_CHECKING or HAS_PYDANTIC_V2:
+    from pydantic.v1 import BaseModel, MissingError, PydanticValueError, ValidationError
+    from pydantic.v1.error_wrappers import ErrorWrapper
+else:
+    from pydantic import BaseModel, MissingError, PydanticValueError, ValidationError
+    from pydantic.error_wrappers import ErrorWrapper
+
 from typing_extensions import Literal
 
 from twisted.web.server import Request
diff --git a/synapse/replication/tcp/client.py b/synapse/replication/tcp/client.py
index ca8a76f77c..1c7946522a 100644
--- a/synapse/replication/tcp/client.py
+++ b/synapse/replication/tcp/client.py
@@ -205,6 +205,12 @@ class ReplicationDataHandler:
                     self.notifier.notify_user_joined_room(
                         row.data.event_id, row.data.room_id
                     )
+
+                # If this is a server ACL event, clear the cache in the storage controller.
+                if row.data.type == EventTypes.ServerACL:
+                    self._state_storage_controller.get_server_acl_for_room.invalidate(
+                        (row.data.room_id,)
+                    )
         elif stream_name == UnPartialStatedRoomStream.NAME:
             for row in rows:
                 assert isinstance(row, UnPartialStatedRoomStreamRow)
diff --git a/synapse/rest/client/account.py b/synapse/rest/client/account.py
index 49cd0805fd..e74a87af4d 100644
--- a/synapse/rest/client/account.py
+++ b/synapse/rest/client/account.py
@@ -18,7 +18,12 @@ import random
 from typing import TYPE_CHECKING, List, Optional, Tuple
 from urllib.parse import urlparse
 
-from pydantic import StrictBool, StrictStr, constr
+from synapse._pydantic_compat import HAS_PYDANTIC_V2
+
+if TYPE_CHECKING or HAS_PYDANTIC_V2:
+    from pydantic.v1 import StrictBool, StrictStr, constr
+else:
+    from pydantic import StrictBool, StrictStr, constr
 from typing_extensions import Literal
 
 from twisted.web.server import Request
diff --git a/synapse/rest/client/devices.py b/synapse/rest/client/devices.py
index 925f037743..80ae937921 100644
--- a/synapse/rest/client/devices.py
+++ b/synapse/rest/client/devices.py
@@ -17,7 +17,12 @@ import logging
 from http import HTTPStatus
 from typing import TYPE_CHECKING, List, Optional, Tuple
 
-from pydantic import Extra, StrictStr
+from synapse._pydantic_compat import HAS_PYDANTIC_V2
+
+if TYPE_CHECKING or HAS_PYDANTIC_V2:
+    from pydantic.v1 import Extra, StrictStr
+else:
+    from pydantic import Extra, StrictStr
 
 from synapse.api import errors
 from synapse.api.errors import NotFoundError, SynapseError, UnrecognizedRequestError
diff --git a/synapse/rest/client/directory.py b/synapse/rest/client/directory.py
index 570bb52747..82944ca711 100644
--- a/synapse/rest/client/directory.py
+++ b/synapse/rest/client/directory.py
@@ -15,7 +15,13 @@
 import logging
 from typing import TYPE_CHECKING, List, Optional, Tuple
 
-from pydantic import StrictStr
+from synapse._pydantic_compat import HAS_PYDANTIC_V2
+
+if TYPE_CHECKING or HAS_PYDANTIC_V2:
+    from pydantic.v1 import StrictStr
+else:
+    from pydantic import StrictStr
+
 from typing_extensions import Literal
 
 from twisted.web.server import Request
diff --git a/synapse/rest/client/models.py b/synapse/rest/client/models.py
index 3d7940b0fc..880f79473c 100644
--- a/synapse/rest/client/models.py
+++ b/synapse/rest/client/models.py
@@ -13,7 +13,12 @@
 # limitations under the License.
 from typing import TYPE_CHECKING, Dict, Optional
 
-from pydantic import Extra, StrictInt, StrictStr, constr, validator
+from synapse._pydantic_compat import HAS_PYDANTIC_V2
+
+if TYPE_CHECKING or HAS_PYDANTIC_V2:
+    from pydantic.v1 import Extra, StrictInt, StrictStr, constr, validator
+else:
+    from pydantic import Extra, StrictInt, StrictStr, constr, validator
 
 from synapse.rest.models import RequestBodyModel
 from synapse.util.threepids import validate_email
diff --git a/synapse/rest/key/v2/remote_key_resource.py b/synapse/rest/key/v2/remote_key_resource.py
index 0aaa838d04..48c47058db 100644
--- a/synapse/rest/key/v2/remote_key_resource.py
+++ b/synapse/rest/key/v2/remote_key_resource.py
@@ -16,7 +16,13 @@ import logging
 import re
 from typing import TYPE_CHECKING, Dict, Mapping, Optional, Set, Tuple
 
-from pydantic import Extra, StrictInt, StrictStr
+from synapse._pydantic_compat import HAS_PYDANTIC_V2
+
+if TYPE_CHECKING or HAS_PYDANTIC_V2:
+    from pydantic.v1 import Extra, StrictInt, StrictStr
+else:
+    from pydantic import StrictInt, StrictStr, Extra
+
 from signedjson.sign import sign_json
 
 from twisted.web.server import Request
diff --git a/synapse/rest/models.py b/synapse/rest/models.py
index d47de5c19e..de354a2135 100644
--- a/synapse/rest/models.py
+++ b/synapse/rest/models.py
@@ -11,7 +11,14 @@
 # WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
 # See the License for the specific language governing permissions and
 # limitations under the License.
-from pydantic import BaseModel, Extra
+from typing import TYPE_CHECKING
+
+from synapse._pydantic_compat import HAS_PYDANTIC_V2
+
+if TYPE_CHECKING or HAS_PYDANTIC_V2:
+    from pydantic.v1 import BaseModel, Extra
+else:
+    from pydantic import BaseModel, Extra
 
 
 class RequestBodyModel(BaseModel):
diff --git a/synapse/state/v2.py b/synapse/state/v2.py
index 1752f95db8..b2e63aed1e 100644
--- a/synapse/state/v2.py
+++ b/synapse/state/v2.py
@@ -23,7 +23,6 @@ from typing import (
     Generator,
     Iterable,
     List,
-    Mapping,
     Optional,
     Sequence,
     Set,
@@ -269,7 +268,7 @@ async def _get_power_level_for_sender(
 
 async def _get_auth_chain_difference(
     room_id: str,
-    state_sets: Sequence[Mapping[Any, str]],
+    state_sets: Sequence[StateMap[str]],
     unpersisted_events: Dict[str, EventBase],
     state_res_store: StateResolutionStore,
 ) -> Set[str]:
@@ -405,7 +404,7 @@ def _seperate(
 
     # mypy doesn't understand that discarding None above means that conflicted
     # state is StateMap[Set[str]], not StateMap[Set[Optional[Str]]].
-    return unconflicted_state, conflicted_state  # type: ignore
+    return unconflicted_state, conflicted_state  # type: ignore[return-value]
 
 
 def _is_power_event(event: EventBase) -> bool:
diff --git a/synapse/storage/background_updates.py b/synapse/storage/background_updates.py
index 58d83ade88..b66347a79f 100644
--- a/synapse/storage/background_updates.py
+++ b/synapse/storage/background_updates.py
@@ -31,8 +31,8 @@ from typing import (
 )
 
 import attr
-from pydantic import BaseModel
 
+from synapse._pydantic_compat import HAS_PYDANTIC_V2
 from synapse.metrics.background_process_metrics import run_as_background_process
 from synapse.storage.engines import PostgresEngine
 from synapse.storage.types import Connection, Cursor
@@ -41,6 +41,11 @@ from synapse.util import Clock, json_encoder
 
 from . import engines
 
+if TYPE_CHECKING or HAS_PYDANTIC_V2:
+    from pydantic.v1 import BaseModel
+else:
+    from pydantic import BaseModel
+
 if TYPE_CHECKING:
     from synapse.server import HomeServer
     from synapse.storage.database import (
diff --git a/synapse/storage/controllers/state.py b/synapse/storage/controllers/state.py
index 10d219c045..46957723a1 100644
--- a/synapse/storage/controllers/state.py
+++ b/synapse/storage/controllers/state.py
@@ -37,6 +37,7 @@ from synapse.storage.util.partial_state_events_tracker import (
     PartialCurrentStateTracker,
     PartialStateEventsTracker,
 )
+from synapse.synapse_rust.acl import ServerAclEvaluator
 from synapse.types import MutableStateMap, StateMap, get_domain_from_id
 from synapse.types.state import StateFilter
 from synapse.util.async_helpers import Linearizer
@@ -501,6 +502,31 @@ class StateStorageController:
 
         return event.content.get("alias")
 
+    @cached()
+    async def get_server_acl_for_room(
+        self, room_id: str
+    ) -> Optional[ServerAclEvaluator]:
+        """Get the server ACL evaluator for room, if any
+
+        This does up-front parsing of the content to ignore bad data and pre-compile
+        regular expressions.
+
+        Args:
+            room_id: The room ID
+
+        Returns:
+            The server ACL evaluator, if any
+        """
+
+        acl_event = await self.get_current_state_event(
+            room_id, EventTypes.ServerACL, ""
+        )
+
+        if not acl_event:
+            return None
+
+        return server_acl_evaluator_from_event(acl_event)
+
     @trace
     @tag_args
     async def get_current_state_deltas(
@@ -760,3 +786,36 @@ class StateStorageController:
                 cache.state_group = object()
 
         return frozenset(cache.hosts_to_joined_users)
+
+
+def server_acl_evaluator_from_event(acl_event: EventBase) -> "ServerAclEvaluator":
+    """
+    Create a ServerAclEvaluator from a m.room.server_acl event's content.
+
+    This does up-front parsing of the content to ignore bad data. It then creates
+    the ServerAclEvaluator which will pre-compile regular expressions from the globs.
+    """
+
+    # first of all, parse if literal IPs are blocked.
+    allow_ip_literals = acl_event.content.get("allow_ip_literals", True)
+    if not isinstance(allow_ip_literals, bool):
+        logger.warning("Ignoring non-bool allow_ip_literals flag")
+        allow_ip_literals = True
+
+    # next, parse the deny list by ignoring any non-strings.
+    deny = acl_event.content.get("deny", [])
+    if not isinstance(deny, (list, tuple)):
+        logger.warning("Ignoring non-list deny ACL %s", deny)
+        deny = []
+    else:
+        deny = [s for s in deny if isinstance(s, str)]
+
+    # then the allow list.
+    allow = acl_event.content.get("allow", [])
+    if not isinstance(allow, (list, tuple)):
+        logger.warning("Ignoring non-list allow ACL %s", allow)
+        allow = []
+    else:
+        allow = [s for s in allow if isinstance(s, str)]
+
+    return ServerAclEvaluator(allow_ip_literals, allow, deny)
diff --git a/synapse/storage/database.py b/synapse/storage/database.py
index dc5bf4d482..3295ebc74d 100644
--- a/synapse/storage/database.py
+++ b/synapse/storage/database.py
@@ -367,19 +367,7 @@ class LoggingTransaction:
     @property
     def description(
         self,
-    ) -> Optional[
-        Sequence[
-            Tuple[
-                str,
-                Optional[Any],
-                Optional[int],
-                Optional[int],
-                Optional[int],
-                Optional[int],
-                Optional[int],
-            ]
-        ]
-    ]:
+    ) -> Optional[Sequence[Any]]:
         return self.txn.description
 
     def execute_batch(self, sql: str, args: Iterable[Iterable[Any]]) -> None:
diff --git a/synapse/storage/databases/main/push_rule.py b/synapse/storage/databases/main/push_rule.py
index af69944008..923166974c 100644
--- a/synapse/storage/databases/main/push_rule.py
+++ b/synapse/storage/databases/main/push_rule.py
@@ -88,6 +88,7 @@ def _load_rules(
         msc1767_enabled=experimental_config.msc1767_enabled,
         msc3664_enabled=experimental_config.msc3664_enabled,
         msc3381_polls_enabled=experimental_config.msc3381_polls_enabled,
+        msc4028_push_encrypted_events=experimental_config.msc4028_push_encrypted_events,
     )
 
     return filtered_rules
diff --git a/synapse/storage/databases/state/bg_updates.py b/synapse/storage/databases/state/bg_updates.py
index a532626602..d2e942cbd3 100644
--- a/synapse/storage/databases/state/bg_updates.py
+++ b/synapse/storage/databases/state/bg_updates.py
@@ -94,6 +94,18 @@ class StateGroupBackgroundUpdateStore(SQLBaseStore):
         groups: List[int],
         state_filter: Optional[StateFilter] = None,
     ) -> Mapping[int, StateMap[str]]:
+        """
+        Given a number of state groups, fetch the latest state for each group.
+
+        Args:
+            txn: The transaction object.
+            groups: The given state groups that you want to fetch the latest state for.
+            state_filter: The state filter to apply the state we fetch state from the database.
+
+        Returns:
+            Map from state_group to a StateMap at that point.
+        """
+
         state_filter = state_filter or StateFilter.all()
 
         results: Dict[int, MutableStateMap[str]] = {group: {} for group in groups}
@@ -206,8 +218,10 @@ class StateGroupBackgroundUpdateStore(SQLBaseStore):
             if where_clause:
                 where_clause = " AND (%s)" % (where_clause,)
 
-            # 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)
+            # XXX: We could `WITH RECURSIVE` here since it's supported on SQLite 3.8.3
+            # or higher and our minimum supported version is greater than that.
+            #
+            # We just haven't put in the time to refactor this.
             for group in groups:
                 next_group: Optional[int] = group
 
diff --git a/synapse/storage/types.py b/synapse/storage/types.py
index 540f046338..1d9f510784 100644
--- a/synapse/storage/types.py
+++ b/synapse/storage/types.py
@@ -54,6 +54,9 @@ class Cursor(Protocol):
     def description(
         self,
     ) -> Optional[Sequence[Any]]:
+        # 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.
         ...
 
     @property
diff --git a/tests/federation/test_federation_server.py b/tests/federation/test_federation_server.py
index 5c850d1843..1831a5b47a 100644
--- a/tests/federation/test_federation_server.py
+++ b/tests/federation/test_federation_server.py
@@ -22,10 +22,10 @@ from twisted.test.proto_helpers import MemoryReactor
 from synapse.api.room_versions import KNOWN_ROOM_VERSIONS
 from synapse.config.server import DEFAULT_ROOM_VERSION
 from synapse.events import EventBase, make_event_from_dict
-from synapse.federation.federation_server import server_matches_acl_event
 from synapse.rest import admin
 from synapse.rest.client import login, room
 from synapse.server import HomeServer
+from synapse.storage.controllers.state import server_acl_evaluator_from_event
 from synapse.types import JsonDict
 from synapse.util import Clock
 
@@ -67,37 +67,46 @@ class ServerACLsTestCase(unittest.TestCase):
         e = _create_acl_event({"allow": ["*"], "deny": ["evil.com"]})
         logging.info("ACL event: %s", e.content)
 
-        self.assertFalse(server_matches_acl_event("evil.com", e))
-        self.assertFalse(server_matches_acl_event("EVIL.COM", e))
+        server_acl_evalutor = server_acl_evaluator_from_event(e)
 
-        self.assertTrue(server_matches_acl_event("evil.com.au", e))
-        self.assertTrue(server_matches_acl_event("honestly.not.evil.com", e))
+        self.assertFalse(server_acl_evalutor.server_matches_acl_event("evil.com"))
+        self.assertFalse(server_acl_evalutor.server_matches_acl_event("EVIL.COM"))
+
+        self.assertTrue(server_acl_evalutor.server_matches_acl_event("evil.com.au"))
+        self.assertTrue(
+            server_acl_evalutor.server_matches_acl_event("honestly.not.evil.com")
+        )
 
     def test_block_ip_literals(self) -> None:
         e = _create_acl_event({"allow_ip_literals": False, "allow": ["*"]})
         logging.info("ACL event: %s", e.content)
 
-        self.assertFalse(server_matches_acl_event("1.2.3.4", e))
-        self.assertTrue(server_matches_acl_event("1a.2.3.4", e))
-        self.assertFalse(server_matches_acl_event("[1:2::]", e))
-        self.assertTrue(server_matches_acl_event("1:2:3:4", e))
+        server_acl_evalutor = server_acl_evaluator_from_event(e)
+
+        self.assertFalse(server_acl_evalutor.server_matches_acl_event("1.2.3.4"))
+        self.assertTrue(server_acl_evalutor.server_matches_acl_event("1a.2.3.4"))
+        self.assertFalse(server_acl_evalutor.server_matches_acl_event("[1:2::]"))
+        self.assertTrue(server_acl_evalutor.server_matches_acl_event("1:2:3:4"))
 
     def test_wildcard_matching(self) -> None:
         e = _create_acl_event({"allow": ["good*.com"]})
+
+        server_acl_evalutor = server_acl_evaluator_from_event(e)
+
         self.assertTrue(
-            server_matches_acl_event("good.com", e),
+            server_acl_evalutor.server_matches_acl_event("good.com"),
             "* matches 0 characters",
         )
         self.assertTrue(
-            server_matches_acl_event("GOOD.COM", e),
+            server_acl_evalutor.server_matches_acl_event("GOOD.COM"),
             "pattern is case-insensitive",
         )
         self.assertTrue(
-            server_matches_acl_event("good.aa.com", e),
+            server_acl_evalutor.server_matches_acl_event("good.aa.com"),
             "* matches several characters, including '.'",
         )
         self.assertFalse(
-            server_matches_acl_event("ishgood.com", e),
+            server_acl_evalutor.server_matches_acl_event("ishgood.com"),
             "pattern does not allow prefixes",
         )
 
diff --git a/tests/rest/client/test_models.py b/tests/rest/client/test_models.py
index 0b8fcb0c47..524ea6047e 100644
--- a/tests/rest/client/test_models.py
+++ b/tests/rest/client/test_models.py
@@ -12,12 +12,18 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 import unittest as stdlib_unittest
+from typing import TYPE_CHECKING
 
-from pydantic import BaseModel, ValidationError
 from typing_extensions import Literal
 
+from synapse._pydantic_compat import HAS_PYDANTIC_V2
 from synapse.rest.client.models import EmailRequestTokenBody
 
+if TYPE_CHECKING or HAS_PYDANTIC_V2:
+    from pydantic.v1 import BaseModel, ValidationError
+else:
+    from pydantic import BaseModel, ValidationError
+
 
 class ThreepidMediumEnumTestCase(stdlib_unittest.TestCase):
     class Model(BaseModel):
diff --git a/tests/state/test_v2.py b/tests/state/test_v2.py
index 2e3f2318d9..6a2f7584f6 100644
--- a/tests/state/test_v2.py
+++ b/tests/state/test_v2.py
@@ -719,7 +719,10 @@ class AuthChainDifferenceTestCase(unittest.TestCase):
         persisted_events = {a.event_id: a, b.event_id: b}
         unpersited_events = {c.event_id: c}
 
-        state_sets = [{"a": a.event_id, "b": b.event_id}, {"c": c.event_id}]
+        state_sets = [
+            {("a", ""): a.event_id, ("b", ""): b.event_id},
+            {("c", ""): c.event_id},
+        ]
 
         store = TestStateResolutionStore(persisted_events)
 
@@ -774,8 +777,8 @@ class AuthChainDifferenceTestCase(unittest.TestCase):
         unpersited_events = {c.event_id: c, d.event_id: d}
 
         state_sets = [
-            {"a": a.event_id, "b": b.event_id},
-            {"c": c.event_id, "d": d.event_id},
+            {("a", ""): a.event_id, ("b", ""): b.event_id},
+            {("c", ""): c.event_id, ("d", ""): d.event_id},
         ]
 
         store = TestStateResolutionStore(persisted_events)
@@ -841,8 +844,8 @@ class AuthChainDifferenceTestCase(unittest.TestCase):
         unpersited_events = {c.event_id: c, d.event_id: d, e.event_id: e}
 
         state_sets = [
-            {"a": a.event_id, "b": b.event_id, "e": e.event_id},
-            {"c": c.event_id, "d": d.event_id},
+            {("a", ""): a.event_id, ("b", ""): b.event_id, ("e", ""): e.event_id},
+            {("c", ""): c.event_id, ("d", ""): d.event_id},
         ]
 
         store = TestStateResolutionStore(persisted_events)