Document importance of public_baseurl for delegation and OIDC (#19270)

I just stumbled across the fact that my config used delegation as
recommended by the docs, and hosted Synapse on a subdomain. However my
config never had `public_baseurl` set and worked without issues, until I
just now tried to setup OIDC.

OIDC is initialized by the client instructing to open a URL on the
homeserver, and initially the correct URL is called, but Synapse does
not recognize it without `public_baseurl` being set correctly. After
changing this it immediately started working.

So in order to prevent anybody from making the same mistake, this adds a
small clarifying block in the OIDC docs.

.ci/before_build_wheel.sh

@@ -7,4 +7,4 @@ if command -v yum &> /dev/null; then
 fi
 
 # Install a Rust toolchain
-curl https://sh.rustup.rs -sSf | sh -s -- --default-toolchain 1.82.0 -y --profile minimal
+curl https://sh.rustup.rs -sSf | sh -s -- --default-toolchain stable -y --profile minimal

.ci/scripts/auditwheel_wrapper.py

@@ -1,146 +0,0 @@
-#!/usr/bin/env python
-#
-# This file is licensed under the Affero General Public License (AGPL) version 3.
-#
-# Copyright (C) 2023 New Vector, Ltd
-#
-# This program is free software: you can redistribute it and/or modify
-# it under the terms of the GNU Affero General Public License as
-# published by the Free Software Foundation, either version 3 of the
-# License, or (at your option) any later version.
-#
-# See the GNU Affero General Public License for more details:
-# <https://www.gnu.org/licenses/agpl-3.0.html>.
-#
-# Originally licensed under the Apache License, Version 2.0:
-# <http://www.apache.org/licenses/LICENSE-2.0>.
-#
-# [This file includes modifications made by New Vector Limited]
-#
-#
-
-# Wraps `auditwheel repair` to first check if we're repairing a potentially abi3
-# compatible wheel, if so rename the wheel before repairing it.
-
-import argparse
-import os
-import subprocess
-from zipfile import ZipFile
-
-from packaging.tags import Tag
-from packaging.utils import parse_wheel_filename
-from packaging.version import Version
-
-
-def check_is_abi3_compatible(wheel_file: str) -> None:
-    """Check the contents of the built wheel for any `.so` files that are *not*
-    abi3 compatible.
-    """
-
-    with ZipFile(wheel_file, "r") as wheel:
-        for file in wheel.namelist():
-            if not file.endswith(".so"):
-                continue
-
-            if not file.endswith(".abi3.so"):
-                raise Exception(f"Found non-abi3 lib: {file}")
-
-
-def cpython(wheel_file: str, name: str, version: Version, tag: Tag) -> str:
-    """Replaces the cpython wheel file with a ABI3 compatible wheel"""
-
-    if tag.abi == "abi3":
-        # Nothing to do.
-        return wheel_file
-
-    check_is_abi3_compatible(wheel_file)
-
-    # HACK: it seems that some older versions of pip will consider a wheel marked
-    # as macosx_11_0 as incompatible with Big Sur. I haven't done the full archaeology
-    # here; there are some clues in
-    #     https://github.com/pantsbuild/pants/pull/12857
-    #     https://github.com/pypa/pip/issues/9138
-    #     https://github.com/pypa/packaging/pull/319
-    # Empirically this seems to work, note that macOS 11 and 10.16 are the same,
-    # both versions are valid for backwards compatibility.
-    platform = tag.platform.replace("macosx_11_0", "macosx_10_16")
-    abi3_tag = Tag(tag.interpreter, "abi3", platform)
-
-    dirname = os.path.dirname(wheel_file)
-    new_wheel_file = os.path.join(
-        dirname,
-        f"{name}-{version}-{abi3_tag}.whl",
-    )
-
-    os.rename(wheel_file, new_wheel_file)
-
-    print("Renamed wheel to", new_wheel_file)
-
-    return new_wheel_file
-
-
-def main(wheel_file: str, dest_dir: str, archs: str | None) -> None:
-    """Entry point"""
-
-    # Parse the wheel file name into its parts. Note that `parse_wheel_filename`
-    # normalizes the package name (i.e. it converts matrix_synapse ->
-    # matrix-synapse), which is not what we want.
-    _, version, build, tags = parse_wheel_filename(os.path.basename(wheel_file))
-    name = os.path.basename(wheel_file).split("-")[0]
-
-    if len(tags) != 1:
-        # We expect only a wheel file with only a single tag
-        raise Exception(f"Unexpectedly found multiple tags: {tags}")
-
-    tag = next(iter(tags))
-
-    if build:
-        # We don't use build tags in Synapse
-        raise Exception(f"Unexpected build tag: {build}")
-
-    # If the wheel is for cpython then convert it into an abi3 wheel.
-    if tag.interpreter.startswith("cp"):
-        wheel_file = cpython(wheel_file, name, version, tag)
-
-    # Finally, repair the wheel.
-    if archs is not None:
-        # If we are given archs then we are on macos and need to use
-        # `delocate-listdeps`.
-        subprocess.run(["delocate-listdeps", wheel_file], check=True)
-        subprocess.run(
-            ["delocate-wheel", "--require-archs", archs, "-w", dest_dir, wheel_file],
-            check=True,
-        )
-    else:
-        subprocess.run(["auditwheel", "repair", "-w", dest_dir, wheel_file], check=True)
-
-
-if __name__ == "__main__":
-    parser = argparse.ArgumentParser(description="Tag wheel as abi3 and repair it.")
-
-    parser.add_argument(
-        "--wheel-dir",
-        "-w",
-        metavar="WHEEL_DIR",
-        help="Directory to store delocated wheels",
-        required=True,
-    )
-
-    parser.add_argument(
-        "--require-archs",
-        metavar="archs",
-        default=None,
-    )
-
-    parser.add_argument(
-        "wheel_file",
-        metavar="WHEEL_FILE",
-    )
-
-    args = parser.parse_args()
-
-    wheel_file = args.wheel_file
-    wheel_dir = args.wheel_dir
-    archs = args.require_archs
-
-    main(wheel_file, wheel_dir, archs)

.ci/scripts/prepare_old_deps.sh

@@ -1,39 +0,0 @@
-#!/usr/bin/env bash
-# this script is run by GitHub Actions in a plain `jammy` container; it
-# - installs the minimal system requirements, and poetry;
-# - patches the project definition file to refer to old versions only;
-# - creates a venv with these old versions using poetry; and finally
-# - invokes `trial` to run the tests with old deps.
-
-set -ex
-
-# Prevent virtualenv from auto-updating pip to an incompatible version
-export VIRTUALENV_NO_DOWNLOAD=1
-
-# TODO: in the future, we could use an implementation of
-#   https://github.com/python-poetry/poetry/issues/3527
-#   https://github.com/pypa/pip/issues/8085
-# to select the lowest possible versions, rather than resorting to this sed script.
-
-# Patch the project definitions in-place:
-# - `-E` use extended regex syntax.
-# - Don't modify the line that defines required Python versions.
-# - Replace all lower and tilde bounds with exact bounds.
-# - Replace all caret bounds with exact bounds.
-# - Delete all lines referring to psycopg2 - so no testing of postgres support.
-# - Use pyopenssl 17.0, which is the oldest version that works with
-#   a `cryptography` compiled against OpenSSL 1.1.
-# - Omit systemd: we're not logging to journal here.
-
-sed -i -E '
-  /^\s*requires-python\s*=/b
-  s/[~>]=/==/g
-  s/\^/==/g
-  /psycopg2/d
-  s/pyOpenSSL\s*==\s*16\.0\.0"/pyOpenSSL==17.0.0"/
-  /systemd/d
-' pyproject.toml
-
-echo "::group::Patched pyproject.toml"
-cat pyproject.toml
-echo "::endgroup::"

.github/dependabot.yml

@@ -1,23 +1,92 @@
 version: 2
+# As dependabot is currently only run on a weekly basis, we raise the
+# open-pull-requests-limit to 10 (from the default of 5) to better ensure we
+# don't continuously grow a backlog of updates.
 updates:
   - # "pip" is the correct setting for poetry, per https://docs.github.com/en/code-security/dependabot/dependabot-version-updates/configuration-options-for-the-dependabot.yml-file#package-ecosystem
     package-ecosystem: "pip"
     directory: "/"
+    open-pull-requests-limit: 10
     schedule:
       interval: "weekly"
+    # Group patch updates to packages together into a single PR, as they rarely
+    # if ever contain breaking changes that need to be reviewed separately.
+    # 
+    # Less PRs means a streamlined review process.
+    #
+    # Python packages follow semantic versioning, and tend to only introduce
+    # breaking changes in major version bumps. Thus, we'll group minor and patch
+    # versions together.
+    groups:
+      minor-and-patches:
+        applies-to: version-updates
+        patterns:
+          - "*"
+        update-types:
+          - "minor"
+          - "patch"
+    # Prevent pulling packages that were recently updated to help mitigate
+    # supply chain attacks. 14 days was taken from the recommendation at
+    # https://blog.yossarian.net/2025/11/21/We-should-all-be-using-dependency-cooldowns
+    # where the author noted that 9/10 attacks would have been mitigated by a
+    # two week cooldown.
+    #
+    # The cooldown only applies to general updates; security updates will still
+    # be pulled in as soon as possible.
+    cooldown:
+      default-days: 14
 
   - package-ecosystem: "docker"
     directory: "/docker"
+    open-pull-requests-limit: 10
     schedule:
       interval: "weekly"
+    # For container versions, breaking changes are also typically only introduced in major
+    # package bumps.
+    groups:
+      minor-and-patches:
+        applies-to: version-updates
+        patterns:
+          - "*"
+        update-types:
+          - "minor"
+          - "patch"
+    cooldown:
+      default-days: 14
 
   - package-ecosystem: "github-actions"
     directory: "/"
+    open-pull-requests-limit: 10
     schedule:
       interval: "weekly"
+    # Similarly for GitHub Actions, breaking changes are typically only introduced in major
+    # package bumps.
+    groups:
+      minor-and-patches:
+        applies-to: version-updates
+        patterns:
+          - "*"
+        update-types:
+          - "minor"
+          - "patch"
+    cooldown:
+      default-days: 14
 
   - package-ecosystem: "cargo"
     directory: "/"
+    open-pull-requests-limit: 10
     versioning-strategy: "lockfile-only"
     schedule:
       interval: "weekly"
+    # The Rust ecosystem is special in that breaking changes are often introduced
+    # in minor version bumps, as packages typically stay pre-1.0 for a long time.
+    # Thus we specifically keep minor version bumps separate in their own PRs.
+    groups:
+      patches:
+        applies-to: version-updates
+        patterns:
+          - "*"
+        update-types:
+          - "patch"
+    cooldown:
+      default-days: 14

.github/workflows/docs-pr-netlify.yaml

@@ -1,34 +0,0 @@
-name: Deploy documentation PR preview
-
-on:
-  workflow_run:
-    workflows: [ "Prepare documentation PR preview" ]
-    types:
-      - completed
-
-jobs:
-  netlify:
-    if: github.event.workflow_run.conclusion == 'success' && github.event.workflow_run.event == 'pull_request'
-    runs-on: ubuntu-latest
-    steps:
-      # 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@ac66b43f0e6a346234dd65d4d0c8fbb31cb316e5 # v11
-        with:
-          workflow: docs-pr.yaml
-          run_id: ${{ github.event.workflow_run.id }}
-          name: book
-          path: book
-
-      - name: 📤 Deploy to Netlify
-        uses: matrix-org/netlify-pr-preview@9805cd123fc9a7e421e35340a05e1ebc5dee46b5 # v3
-        with:
-          path: book
-          owner: ${{ github.event.workflow_run.head_repository.owner.login }}
-          branch: ${{ github.event.workflow_run.head_branch }}
-          revision: ${{ github.event.workflow_run.head_sha }}
-          token: ${{ secrets.NETLIFY_AUTH_TOKEN }}
-          site_id: ${{ secrets.NETLIFY_SITE_ID }}
-          desc: Documentation preview
-          deployment_env: PR Documentation Preview

.github/workflows/release-artifacts.yml

@@ -5,7 +5,7 @@ name: Build release artifacts
 on:
   # we build on PRs and develop to (hopefully) get early warning
   # of things breaking (but only build one set of debs). PRs skip
-  # building wheels on macOS & ARM.
+  # building wheels on ARM.
   pull_request:
   push:
     branches: ["develop", "release-*"]

.github/workflows/tests.yml

@@ -452,14 +452,12 @@ jobs:
           python-version: '3.10'
 
       - name: Prepare old deps
-        if: steps.cache-poetry-old-deps.outputs.cache-hit != 'true'
-        run: .ci/scripts/prepare_old_deps.sh
-
-      # Note: we install using `pip` here, not poetry. `poetry install` ignores the
-      # build-system section (https://github.com/python-poetry/poetry/issues/6154), but
-      # we explicitly want to test that you can `pip install` using the oldest version
-      # of poetry-core and setuptools-rust.
-      - run: pip install .[all,test]
+        # Note: we install using `uv` here, not poetry or pip to allow us to test with the
+        # minimum version of all dependencies, both those explicitly specified and those
+        # implicitly brought in by the explicit dependencies. 
+        run: |
+          pip install uv
+          uv pip install --system --resolution=lowest .[all,test]
 
       # We nuke the local copy, as we've installed synapse into the virtualenv
       # (rather than use an editable install, which we no longer support). If we

changelog.d/18402.misc

@@ -0,0 +1 @@
+Group together dependabot update PRs to reduce the review load.

changelog.d/19187.misc

@@ -0,0 +1 @@
+Fix `HomeServer.shutdown()` failing if the homeserver hasn't been setup yet.

changelog.d/19206.bugfix

@@ -0,0 +1 @@
+Fix sliding sync performance slow down for long lived connections.

changelog.d/19212.misc

@@ -0,0 +1 @@
+Respond with useful error codes with `Content-Length` header/s are invalid.

changelog.d/19232.misc

@@ -0,0 +1 @@
+Fix `HomeServer.shutdown()` failing if the homeserver failed to `start`.

changelog.d/19234.misc

@@ -0,0 +1 @@
+Switch the build backend from `poetry-core` to `maturin`.

changelog.d/19253.misc

@@ -0,0 +1 @@
+Raise the limit for concurrently-open non-security @dependabot PRs from 5 to 10.

changelog.d/19254.removal

@@ -0,0 +1 @@
+Remove the "Updates to locked dependencies" section from the changelog due to lack of use and the maintenance burden.

changelog.d/19258.misc

@@ -0,0 +1 @@
+Require 14 days to pass before pulling in general dependency updates to help mitigate upstream supply chain attacks.

changelog.d/19260.feature

@@ -0,0 +1 @@
+Add `memberships` endpoint to the admin API. This is useful for forensics and T&S purpose.

changelog.d/19262.misc

@@ -0,0 +1 @@
+Drop the broken netlify documentation workflow until a new one is implemented.

changelog.d/19267.bugfix

@@ -0,0 +1 @@
+Fix bug where `Duration` was logged incorrectly.

changelog.d/19268.feature

@@ -0,0 +1 @@
+Add an admin API for retrieving a paginated list of quarantined media.

changelog.d/19270.doc

@@ -0,0 +1 @@
+Document the importance of `public_baseurl` when configuring OpenID Connect authentication.

changelog.d/19274.bugfix

@@ -0,0 +1 @@
+Fix bug introduced in 1.143.0 that broke support for versions of `zope-interface` older than 6.2.

changelog.d/19278.misc

@@ -0,0 +1 @@
+Don't include debug logs in `Clock` unless explicitly enabled.

changelog.d/19289.misc

@@ -0,0 +1 @@
+Use `uv` to test olddeps to ensure all transitive dependencies use minimum versions.

changelog.d/19302.misc

@@ -0,0 +1 @@
+Unpin the version of Rust we use to build Synapse wheels (was 1.82.0) now that MacOS support has been dropped.

docs/admin_api/media_admin_api.md

@@ -73,6 +73,33 @@ Response:
 }
 ```
 
+## Listing all quarantined media
+
+This API returns a list of all quarantined media on the server. It is paginated, and can be scoped to either local or
+remote media. Note that the pagination values are also scoped to the request parameters - changing them but keeping the
+same pagination values will result in unexpected results.
+
+Request:
+```http
+GET /_synapse/admin/v1/media/quarantined?from=0&limit=100&kind=local
+```
+
+`from` and `limit` are optional parameters, and default to `0` and `100` respectively. They are the row index and number
+of rows to return - they are not timestamps.
+
+`kind` *MUST* either be `local` or `remote`.
+
+The API returns a JSON body containing MXC URIs for the quarantined media, like the following:
+
+```json
+{
+  "media": [
+    "mxc://localhost/xwvutsrqponmlkjihgfedcba",
+    "mxc://localhost/abcdefghijklmnopqrstuvwx"
+  ]
+}
+```
+
 # Quarantine media
 
 Quarantining media means that it is marked as inaccessible by users. It applies

docs/admin_api/user_admin_api.md

@@ -505,6 +505,55 @@ with a body of:
 }
 ```
 
+## List room memberships of a user
+
+Gets a list of room memberships for a specific `user_id`. This
+endpoint differs from
+[`GET /_synapse/admin/v1/users/<user_id>/joined_rooms`](#list-joined-rooms-of-a-user)
+in that it returns rooms with memberships other than "join".
+
+The API is:
+
+```
+GET /_synapse/admin/v1/users/<user_id>/memberships
+```
+
+A response body like the following is returned:
+
+```json
+    {
+        "memberships": {
+            "!DuGcnbhHGaSZQoNQR:matrix.org": "join",
+            "!ZtSaPCawyWtxfWiIy:matrix.org": "leave",
+        }
+    }
+```
+
+which is a list of room membership states for the given user. This endpoint can
+be used with both local and remote users, with the caveat that the homeserver will
+only be aware of the memberships for rooms that one of its local users has joined.
+
+Remote user memberships may also be out of date if all local users have since left
+a room. The homeserver will thus no longer receive membership updates about it.
+
+The list includes rooms that the user has since left; other membership states (knock,
+invite, etc.) are also possible.
+
+Note that rooms will only disappear from this list if they are
+[purged](./rooms.md#delete-room-api) from the homeserver.
+
+**Parameters**
+
+The following parameters should be set in the URL:
+
+- `user_id` - fully qualified: for example, `@user:server.com`.
+
+**Response**
+
+The following fields are returned in the JSON response body:
+
+- `memberships` - A map of `room_id` (string) to `membership` state (string).
+
 ## List joined rooms of a user
 
 Gets a list of all `room_id` that a specific `user_id` is joined to and is a member of (participating in).

docs/openid.md

@@ -50,6 +50,11 @@ setting in your configuration file.
 See the [configuration manual](usage/configuration/config_documentation.md#oidc_providers) for some sample settings, as well as
 the text below for example configurations for specific providers.
 
+For setups using [`.well-known` delegation](delegate.md), make sure
+[`public_baseurl`](usage/configuration/config_documentation.md#public_baseurl) is set
+appropriately. If unset, Synapse defaults to `https://<server_name>/` which is used in
+the OIDC callback URL.
+
 ## OIDC Back-Channel Logout
 
 Synapse supports receiving [OpenID Connect Back-Channel Logout](https://openid.net/specs/openid-connect-backchannel-1_0.html) notifications.

poetry.lock

@@ -31,7 +31,7 @@ description = "The ultimate Python library in building OAuth and OpenID Connect
 optional = true
 python-versions = ">=3.9"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"jwt\" or extra == \"oidc\""
+markers = "extra == \"oidc\" or extra == \"jwt\" or extra == \"all\""
 files = [
     {file = "authlib-1.6.5-py2.py3-none-any.whl", hash = "sha256:3e0e0507807f842b02175507bdee8957a1d5707fd4afb17c32fb43fee90b6e3a"},
     {file = "authlib-1.6.5.tar.gz", hash = "sha256:6aaf9c79b7cc96c900f0b284061691c5d4e61221640a948fe690b556a6d6d10b"},
@@ -134,14 +134,14 @@ typecheck = ["mypy"]
 
 [[package]]
 name = "bleach"
-version = "6.2.0"
+version = "6.3.0"
 description = "An easy safelist-based HTML-sanitizing tool."
 optional = false
-python-versions = ">=3.9"
+python-versions = ">=3.10"
 groups = ["main", "dev"]
 files = [
-    {file = "bleach-6.2.0-py3-none-any.whl", hash = "sha256:117d9c6097a7c3d22fd578fcd8d35ff1e125df6736f554da4e432fdd63f31e5e"},
-    {file = "bleach-6.2.0.tar.gz", hash = "sha256:123e894118b8a599fd80d3ec1a6d4cc7ce4e5882b1317a7e1ba69b56e95f991f"},
+    {file = "bleach-6.3.0-py3-none-any.whl", hash = "sha256:fe10ec77c93ddf3d13a73b035abaac7a9f5e436513864ccdad516693213c65d6"},
+    {file = "bleach-6.3.0.tar.gz", hash = "sha256:6f3b91b1c0a02bb9a78b5a454c92506aa0fdf197e1d5e114d2e00c6f64306d22"},
 ]
 
 [package.dependencies]
@@ -176,83 +176,100 @@ files = [
 
 [[package]]
 name = "cffi"
-version = "1.17.1"
+version = "2.0.0"
 description = "Foreign Function Interface for Python calling C code."
 optional = false
-python-versions = ">=3.8"
+python-versions = ">=3.9"
 groups = ["main", "dev"]
 files = [
-    {file = "cffi-1.17.1-cp310-cp310-macosx_10_9_x86_64.whl", hash = "sha256:df8b1c11f177bc2313ec4b2d46baec87a5f3e71fc8b45dab2ee7cae86d9aba14"},
-    {file = "cffi-1.17.1-cp310-cp310-macosx_11_0_arm64.whl", hash = "sha256:8f2cdc858323644ab277e9bb925ad72ae0e67f69e804f4898c070998d50b1a67"},
-    {file = "cffi-1.17.1-cp310-cp310-manylinux_2_12_i686.manylinux2010_i686.manylinux_2_17_i686.manylinux2014_i686.whl", hash = "sha256:edae79245293e15384b51f88b00613ba9f7198016a5948b5dddf4917d4d26382"},
-    {file = "cffi-1.17.1-cp310-cp310-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:45398b671ac6d70e67da8e4224a065cec6a93541bb7aebe1b198a61b58c7b702"},
-    {file = "cffi-1.17.1-cp310-cp310-manylinux_2_17_ppc64le.manylinux2014_ppc64le.whl", hash = "sha256:ad9413ccdeda48c5afdae7e4fa2192157e991ff761e7ab8fdd8926f40b160cc3"},
-    {file = "cffi-1.17.1-cp310-cp310-manylinux_2_17_s390x.manylinux2014_s390x.whl", hash = "sha256:5da5719280082ac6bd9aa7becb3938dc9f9cbd57fac7d2871717b1feb0902ab6"},
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 [package.dependencies]
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 [[package]]
 name = "charset-normalizer"
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 ]
 
 [package.dependencies]
-cffi = {version = ">=1.14", markers = "platform_python_implementation != \"PyPy\""}
+cffi = {version = ">=2.0.0", markers = "python_full_version >= \"3.9.0\" and platform_python_implementation != \"PyPy\""}
+typing-extensions = {version = ">=4.13.2", markers = "python_full_version < \"3.11.0\""}
 
 [package.extras]
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 docstest = ["pyenchant (>=3)", "readme-renderer (>=30.0)", "sphinxcontrib-spelling (>=7.3.1)"]
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-pep8test = ["check-sdist ; python_full_version >= \"3.8.0\"", "click (>=8.0.1)", "mypy (>=1.4)", "ruff (>=0.3.6)"]
+nox = ["nox[uv] (>=2024.4.15)"]
+pep8test = ["check-sdist", "click (>=8.0.1)", "mypy (>=1.14)", "ruff (>=0.11.11)"]
 sdist = ["build (>=1.0.0)"]
 ssh = ["bcrypt (>=3.1.5)"]
-test = ["certifi (>=2024)", "cryptography-vectors (==45.0.7)", "pretend (>=0.7)", "pytest (>=7.4.0)", "pytest-benchmark (>=4.0)", "pytest-cov (>=2.10.1)", "pytest-xdist (>=3.5.0)"]
+test = ["certifi (>=2024)", "cryptography-vectors (==46.0.3)", "pretend (>=0.7)", "pytest (>=7.4.0)", "pytest-benchmark (>=4.0)", "pytest-cov (>=2.10.1)", "pytest-xdist (>=3.5.0)"]
 test-randomorder = ["pytest-randomly"]
 
 [[package]]
@@ -446,7 +481,7 @@ description = "XML bomb protection for Python stdlib modules"
 optional = true
 python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"saml2\""
+markers = "extra == \"saml2\" or extra == \"all\""
 files = [
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@@ -471,7 +506,7 @@ description = "XPath 1.0/2.0/3.0/3.1 parsers and selectors for ElementTree and l
 optional = true
 python-versions = ">=3.7"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"saml2\""
+markers = "extra == \"saml2\" or extra == \"all\""
 files = [
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@@ -521,7 +556,7 @@ description = "Python wrapper for hiredis"
 optional = true
 python-versions = ">=3.8"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"redis\""
+markers = "extra == \"redis\" or extra == \"all\""
 files = [
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@@ -844,7 +879,7 @@ description = "Jaeger Python OpenTracing Tracer implementation"
 optional = true
 python-versions = ">=3.7"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"opentracing\""
+markers = "extra == \"opentracing\" or extra == \"all\""
 files = [
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 ]
@@ -982,7 +1017,7 @@ description = "A strictly RFC 4510 conforming LDAP V3 pure Python client library
 optional = true
 python-versions = "*"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"matrix-synapse-ldap3\""
+markers = "extra == \"matrix-synapse-ldap3\" or extra == \"all\""
 files = [
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@@ -991,6 +1026,92 @@ files = [
 [package.dependencies]
 pyasn1 = ">=0.4.6"
 
+[[package]]
+name = "librt"
+version = "0.6.3"
+description = "Mypyc runtime library"
+optional = false
+python-versions = ">=3.9"
+groups = ["dev"]
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 optional = true
 python-versions = ">=3.8"
 groups = ["main"]
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 python-versions = ">=3.7"
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+    {file = "mypy-1.19.0-py3-none-any.whl", hash = "sha256:0c01c99d626380752e527d5ce8e69ffbba2046eb8a060db0329690849cf9b6f9"},
+    {file = "mypy-1.19.0.tar.gz", hash = "sha256:f6b874ca77f733222641e5c46e4711648c4037ea13646fd0cdc814c2eaec2528"},
 ]
 
 [package.dependencies]
+librt = ">=0.6.2"
 mypy_extensions = ">=1.0.0"
 pathspec = ">=0.9.0"
 tomli = {version = ">=1.1.0", markers = "python_version < \"3.11\""}
@@ -1486,18 +1608,18 @@ files = [
 
 [[package]]
 name = "mypy-zope"
-version = "1.0.13"
+version = "1.0.14"
 description = "Plugin for mypy to support zope interfaces"
 optional = false
 python-versions = "*"
 groups = ["dev"]
 files = [
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+    {file = "mypy_zope-1.0.14-py3-none-any.whl", hash = "sha256:8842ade93630421dbec0c9906d6515f6e65c6407ef8b9b2eb7f4f73ae1e8a42a"},
+    {file = "mypy_zope-1.0.14.tar.gz", hash = "sha256:42555ad4703f2e50c912de3ebe0c7197619c3f71864817fabc5385ecea0f8449"},
 ]
 
 [package.dependencies]
-mypy = ">=1.0.0,<1.18.0"
+mypy = ">=1.0.0,<1.20.0"
 "zope.interface" = "*"
 "zope.schema" = "*"
 
@@ -1526,7 +1648,7 @@ description = "OpenTracing API for Python. See documentation at http://opentraci
 optional = true
 python-versions = "*"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"opentracing\""
+markers = "extra == \"opentracing\" or extra == \"all\""
 files = [
     {file = "opentracing-2.4.0.tar.gz", hash = "sha256:a173117e6ef580d55874734d1fa7ecb6f3655160b8b8974a2a1e98e5ec9c840d"},
 ]
@@ -1575,14 +1697,14 @@ files = [
 
 [[package]]
 name = "phonenumbers"
-version = "9.0.18"
+version = "9.0.19"
 description = "Python version of Google's common library for parsing, formatting, storing and validating international phone numbers."
 optional = false
 python-versions = "*"
 groups = ["main"]
 files = [
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+    {file = "phonenumbers-9.0.19.tar.gz", hash = "sha256:e0674e31554362f4d95383558f7aefde738ef2e7bf96d28a10afd3e87d63a65c"},
 ]
 
 [[package]]
@@ -1716,7 +1838,7 @@ description = "psycopg2 - Python-PostgreSQL Database Adapter"
 optional = true
 python-versions = ">=3.9"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"postgres\""
+markers = "extra == \"postgres\" or extra == \"all\""
 files = [
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@@ -1734,7 +1856,7 @@ description = ".. image:: https://travis-ci.org/chtd/psycopg2cffi.svg?branch=mas
 optional = true
 python-versions = "*"
 groups = ["main"]
-markers = "platform_python_implementation == \"PyPy\" and (extra == \"all\" or extra == \"postgres\")"
+markers = "platform_python_implementation == \"PyPy\" and (extra == \"postgres\" or extra == \"all\")"
 files = [
     {file = "psycopg2cffi-2.9.0.tar.gz", hash = "sha256:7e272edcd837de3a1d12b62185eb85c45a19feda9e62fa1b120c54f9e8d35c52"},
 ]
@@ -1750,7 +1872,7 @@ description = "A Simple library to enable psycopg2 compatability"
 optional = true
 python-versions = "*"
 groups = ["main"]
-markers = "platform_python_implementation == \"PyPy\" and (extra == \"all\" or extra == \"postgres\")"
+markers = "platform_python_implementation == \"PyPy\" and (extra == \"postgres\" or extra == \"all\")"
 files = [
     {file = "psycopg2cffi-compat-1.1.tar.gz", hash = "sha256:d25e921748475522b33d13420aad5c2831c743227dc1f1f2585e0fdb5c914e05"},
 ]
@@ -1792,6 +1914,7 @@ description = "C parser in Python"
 optional = false
 python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*"
 groups = ["main", "dev"]
+markers = "implementation_name != \"PyPy\""
 files = [
     {file = "pycparser-2.21-py2.py3-none-any.whl", hash = "sha256:8ee45429555515e1f6b185e78100aea234072576aa43ab53aefcae078162fca9"},
     {file = "pycparser-2.21.tar.gz", hash = "sha256:e644fdec12f7872f86c58ff790da456218b10f863970249516d60a5eaca77206"},
@@ -2031,7 +2154,7 @@ description = "A development tool to measure, monitor and analyze the memory beh
 optional = true
 python-versions = ">=3.6"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"cache-memory\""
+markers = "extra == \"cache-memory\" or extra == \"all\""
 files = [
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@@ -2084,6 +2207,63 @@ typing-extensions = {version = ">=4.9", markers = "python_version < \"3.13\" and
 docs = ["sphinx (!=5.2.0,!=5.2.0.post0,!=7.2.5)", "sphinx_rtd_theme"]
 test = ["pretend", "pytest (>=3.0.1)", "pytest-rerunfailures"]
 
+[[package]]
+name = "pyparsing"
+version = "3.2.5"
+description = "pyparsing - Classes and methods to define and execute parsing grammars"
+optional = false
+python-versions = ">=3.9"
+groups = ["main"]
+files = [
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+    {file = "pyparsing-3.2.5.tar.gz", hash = "sha256:2df8d5b7b2802ef88e8d016a2eb9c7aeaa923529cd251ed0fe4608275d4105b6"},
+]
+
+[package.extras]
+diagrams = ["jinja2", "railroad-diagrams"]
+
+[[package]]
+name = "pyrsistent"
+version = "0.20.0"
+description = "Persistent/Functional/Immutable data structures"
+optional = false
+python-versions = ">=3.8"
+groups = ["main"]
+files = [
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 [[package]]
 name = "pysaml2"
 version = "7.5.0"
@@ -2091,7 +2271,7 @@ description = "Python implementation of SAML Version 2 Standard"
 optional = true
 python-versions = ">=3.9,<4.0"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"saml2\""
+markers = "extra == \"saml2\" or extra == \"all\""
 files = [
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 optional = true
 python-versions = "!=3.0.*,!=3.1.*,!=3.2.*,>=2.7"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"saml2\""
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 files = [
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 [[package]]
 name = "pytz"
-version = "2022.7.1"
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 description = "World timezone definitions, modern and historical"
 optional = true
 python-versions = "*"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"saml2\""
+markers = "extra == \"saml2\" or extra == \"all\""
 files = [
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 [[package]]
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+version = "0.14.6"
 description = "An extremely fast Python linter and code formatter, written in Rust."
 optional = false
 python-versions = ">=3.7"
 groups = ["dev"]
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 ]
 
 [[package]]
@@ -2548,7 +2728,7 @@ description = "Python client for Sentry (https://sentry.io)"
 optional = true
 python-versions = ">=3.6"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"sentry\""
+markers = "extra == \"sentry\" or extra == \"all\""
 files = [
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@@ -2758,7 +2938,7 @@ description = "Tornado IOLoop Backed Concurrent Futures"
 optional = true
 python-versions = "*"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"opentracing\""
+markers = "extra == \"opentracing\" or extra == \"all\""
 files = [
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@@ -2774,7 +2954,7 @@ description = "Python bindings for the Apache Thrift RPC system"
 optional = true
 python-versions = "*"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"opentracing\""
+markers = "extra == \"opentracing\" or extra == \"all\""
 files = [
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 ]
@@ -2847,7 +3027,7 @@ description = "Tornado is a Python web framework and asynchronous networking lib
 optional = true
 python-versions = ">=3.9"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"opentracing\""
+markers = "extra == \"opentracing\" or extra == \"all\""
 files = [
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@@ -2981,7 +3161,7 @@ description = "non-blocking redis client for python"
 optional = true
 python-versions = "*"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"redis\""
+markers = "extra == \"redis\" or extra == \"all\""
 files = [
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@@ -3192,21 +3372,21 @@ files = [
 
 [[package]]
 name = "urllib3"
-version = "2.5.0"
+version = "2.6.0"
 description = "HTTP library with thread-safe connection pooling, file post, and more."
 optional = false
 python-versions = ">=3.9"
 groups = ["main", "dev"]
 files = [
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 ]
 
 [package.extras]
-brotli = ["brotli (>=1.0.9) ; platform_python_implementation == \"CPython\"", "brotlicffi (>=0.8.0) ; platform_python_implementation != \"CPython\""]
+brotli = ["brotli (>=1.2.0) ; platform_python_implementation == \"CPython\"", "brotlicffi (>=1.2.0.0) ; platform_python_implementation != \"CPython\""]
 h2 = ["h2 (>=4,<5)"]
 socks = ["pysocks (>=1.5.6,!=1.5.7,<2.0)"]
-zstd = ["zstandard (>=0.18.0)"]
+zstd = ["backports-zstd (>=1.0.0) ; python_version < \"3.14\""]
 
 [[package]]
 name = "webencodings"
@@ -3227,7 +3407,7 @@ description = "An XML Schema validator and decoder"
 optional = true
 python-versions = ">=3.7"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"saml2\""
+markers = "extra == \"saml2\" or extra == \"all\""
 files = [
     {file = "xmlschema-2.4.0-py3-none-any.whl", hash = "sha256:dc87be0caaa61f42649899189aab2fd8e0d567f2cf548433ba7b79278d231a4a"},
     {file = "xmlschema-2.4.0.tar.gz", hash = "sha256:d74cd0c10866ac609e1ef94a5a69b018ad16e39077bc6393408b40c6babee793"},
@@ -3345,15 +3525,15 @@ docs = ["Sphinx", "repoze.sphinx.autointerface"]
 test = ["zope.i18nmessageid", "zope.testing", "zope.testrunner"]
 
 [extras]
-all = ["authlib", "hiredis", "jaeger-client", "lxml", "matrix-synapse-ldap3", "opentracing", "psycopg2", "psycopg2cffi", "psycopg2cffi-compat", "pympler", "pysaml2", "sentry-sdk", "txredisapi"]
+all = ["authlib", "defusedxml", "hiredis", "jaeger-client", "lxml", "matrix-synapse-ldap3", "opentracing", "psycopg2", "psycopg2cffi", "psycopg2cffi-compat", "pympler", "pysaml2", "pytz", "sentry-sdk", "thrift", "tornado", "txredisapi"]
 cache-memory = ["pympler"]
 jwt = ["authlib"]
 matrix-synapse-ldap3 = ["matrix-synapse-ldap3"]
 oidc = ["authlib"]
-opentracing = ["jaeger-client", "opentracing"]
+opentracing = ["jaeger-client", "opentracing", "thrift", "tornado"]
 postgres = ["psycopg2", "psycopg2cffi", "psycopg2cffi-compat"]
 redis = ["hiredis", "txredisapi"]
-saml2 = ["pysaml2"]
+saml2 = ["defusedxml", "pysaml2", "pytz"]
 sentry = ["sentry-sdk"]
 systemd = ["systemd-python"]
 test = ["idna", "parameterized"]
@@ -3362,4 +3542,4 @@ url-preview = ["lxml"]
 [metadata]
 lock-version = "2.1"
 python-versions = ">=3.10.0,<4.0.0"
-content-hash = "98b9062f48205a3bcc99b43ae665083d360a15d4a208927fa978df9c36fd5315"
+content-hash = "1caa5072f6304122c89377420f993a54f54587f3618ccc8094ec31642264592c"

pyproject.toml

@@ -42,7 +42,8 @@ dependencies = [
     "Twisted[tls]>=21.2.0",
     "treq>=21.5.0",
     # Twisted has required pyopenssl 16.0 since about Twisted 16.6.
-    "pyOpenSSL>=16.0.0",
+    # pyOpenSSL 16.2.0 fixes compatibility with OpenSSL 1.1.0. 
+    "pyOpenSSL>=16.2.0",
     "PyYAML>=5.3",
     "pyasn1>=0.1.9",
     "pyasn1-modules>=0.0.7",
@@ -95,6 +96,25 @@ dependencies = [
 
     # This is used for parsing multipart responses
     "python-multipart>=0.0.9",
+
+    # Transitive dependency constraints
+    # These dependencies aren't directly required by Synapse.
+    # However, in order for Synapse to build, Synapse requires a higher minimum version
+    # for these dependencies than the minimum specified by the direct dependency.
+    # We should periodically check to see if these dependencies are still necessary and
+    # remove any that are no longer required.
+    "cffi>=1.15", # via cryptography
+    "pynacl>=1.3", # via signedjson
+    "pyparsing>=2.4",  # via packaging
+    "pyrsistent>=0.18.0",  # via jsonschema
+    "requests>=2.16.0", # 2.16.0+ no longer vendors urllib3, avoiding Python 3.10+ incompatibility
+    "urllib3>=1.26.5", # via treq; 1.26.5 fixes Python 3.10+ collections.abc compatibility
+    # 5.2 is the current version in Debian oldstable. If we don't care to support that, then 5.4 is
+    # the minimum version from Ubuntu 22.04 and RHEL 9. (as of 2025-12)
+    # When bumping this version to 6.2 or above, refer to https://github.com/element-hq/synapse/pull/19274
+    # for details of Synapse improvements that may be unlocked. Particularly around the use of `|`
+    # syntax with zope interface types.
+    "zope-interface>=5.2", # via twisted
 ]
 
 [project.optional-dependencies]
@@ -104,7 +124,16 @@ postgres = [
     "psycopg2cffi>=2.8;platform_python_implementation == 'PyPy'",
     "psycopg2cffi-compat==1.1;platform_python_implementation == 'PyPy'",
 ]
-saml2 = ["pysaml2>=4.5.0"]
+saml2 = [
+    "pysaml2>=4.5.0",
+
+    # Transitive dependencies from pysaml2
+    # These dependencies aren't directly required by Synapse.
+    # However, in order for Synapse to build, Synapse requires a higher minimum version
+    # for these dependencies than the minimum specified by the direct dependency.
+    "defusedxml>=0.7.1", # via pysaml2
+    "pytz>=2018.3",  # via pysaml2
+]
 oidc = ["authlib>=0.15.1"]
 # systemd-python is necessary for logging to the systemd journal via
 # `systemd.journal.JournalHandler`, as is documented in
@@ -112,15 +141,25 @@ oidc = ["authlib>=0.15.1"]
 systemd = ["systemd-python>=231"]
 url-preview = ["lxml>=4.6.3"]
 sentry = ["sentry-sdk>=0.7.2"]
-opentracing = ["jaeger-client>=4.2.0", "opentracing>=2.2.0"]
+opentracing = [
+    "jaeger-client>=4.2.0",
+    "opentracing>=2.2.0",
+
+    # Transitive dependencies from jaeger-client
+    # These dependencies aren't directly required by Synapse.
+    # However, in order for Synapse to build, Synapse requires a higher minimum version
+    # for these dependencies than the minimum specified by the direct dependency.
+    "thrift>=0.10",  # via jaeger-client
+    "tornado>=6.0",  # via jaeger-client
+]
 jwt = ["authlib"]
 # hiredis is not a *strict* dependency, but it makes things much faster.
 # (if it is not installed, we fall back to slow code.)
-redis = ["txredisapi>=1.4.7", "hiredis"]
+redis = ["txredisapi>=1.4.7", "hiredis>=0.3"]
 # Required to use experimental `caches.track_memory_usage` config option.
-cache-memory = ["pympler"]
+cache-memory = ["pympler>=1.0"]
 # If this is updated, don't forget to update the equivalent lines in
-# tool.poetry.group.dev.dependencies.
+# `dependency-groups.dev` below.
 test = ["parameterized>=0.9.0", "idna>=3.3"]
 
 # The duplication here is awful.
@@ -149,12 +188,22 @@ all = [
     # opentracing
     "jaeger-client>=4.2.0", "opentracing>=2.2.0",
     # redis
-    "txredisapi>=1.4.7", "hiredis",
+    "txredisapi>=1.4.7", "hiredis>=0.3",
     # cache-memory
-    "pympler",
+    # 1.0 added support for python 3.10, our current minimum supported python version
+    "pympler>=1.0",
     # omitted:
     #   - test: it's useful to have this separate from dev deps in the olddeps job
     #   - systemd: this is a system-based requirement
+
+    # Transitive dependencies
+    # These dependencies aren't directly required by Synapse.
+    # However, in order for Synapse to build, Synapse requires a higher minimum version
+    # for these dependencies than the minimum specified by the direct dependency.
+    "defusedxml>=0.7.1", # via pysaml2
+    "pytz>=2018.3",  # via pysaml2
+    "thrift>=0.10",  # via jaeger-client
+    "tornado>=6.0",  # via jaeger-client
 ]
 
 [project.urls]
@@ -177,6 +226,85 @@ synapse_port_db = "synapse._scripts.synapse_port_db:main"
 synapse_review_recent_signups = "synapse._scripts.review_recent_signups:main"
 update_synapse_database = "synapse._scripts.update_synapse_database:main"
 
+[tool.poetry]
+packages = [{ include = "synapse" }]
+
+[tool.poetry.build]
+# Compile our rust module when using `poetry install`. This is still required
+# while using `poetry` as the build frontend. Saves the developer from needing
+# to run both:
+#
+# $ poetry install
+# $ maturin develop
+script = "build_rust.py"
+# Create a `setup.py` file which will call the `build` method in our build
+# script.
+#
+# Our build script currently uses the "old" build method, where we define a
+# `build` method and `setup.py` calls it. Poetry developers have mentioned that
+# this will eventually be removed:
+# https://github.com/matrix-org/synapse/pull/14949#issuecomment-1418001859
+#
+# The new build method is defined here:
+# https://python-poetry.org/docs/building-extension-modules/#maturin-build-script
+# but is still marked as "unstable" at the time of writing. This would also
+# bump our minimum `poetry-core` version to 1.5.0.
+#
+# We can just drop this work-around entirely if migrating away from
+# Poetry, thus there's little motivation to update the build script.
+generate-setup-file = true
+
+# Dependencies used for developing Synapse itself.
+#
+# Hold off on migrating these to `dev-dependencies` (PEP 735) for now until
+# Poetry 2.2.0+, pip 25.1+ are more widely available.
+[tool.poetry.group.dev.dependencies]
+# We pin development dependencies in poetry.lock so that our tests don't start
+# failing on new releases. Keeping lower bounds loose here means that dependabot
+# can bump versions without having to update the content-hash in the lockfile.
+# This helps prevents merge conflicts when running a batch of dependabot updates.
+ruff = "0.14.6"
+
+# Typechecking
+lxml-stubs = ">=0.4.0"
+mypy = "*"
+mypy-zope = "*"
+types-bleach = ">=4.1.0"
+types-jsonschema = ">=3.2.0"
+types-netaddr = ">=0.8.0.6"
+types-opentracing = ">=2.4.2"
+types-Pillow = ">=8.3.4"
+types-psycopg2 = ">=2.9.9"
+types-pyOpenSSL = ">=20.0.7"
+types-PyYAML = ">=5.4.10"
+types-requests = ">=2.26.0"
+types-setuptools = ">=57.4.0"
+
+# Dependencies which are exclusively required by unit test code. This is
+# NOT a list of all modules that are necessary to run the unit tests.
+# Tests assume that all optional dependencies are installed.
+#
+# If this is updated, don't forget to update the equivalent lines in
+# project.optional-dependencies.test.
+parameterized = ">=0.9.0"
+idna = ">=3.3"
+
+# The following are used by the release script
+click = ">=8.1.3"
+# GitPython was == 3.1.14; bumped to 3.1.20, the first release with type hints.
+GitPython = ">=3.1.20"
+markdown-it-py = ">=3.0.0"
+pygithub = ">=1.59"
+# The following are executed as commands by the release script.
+twine = "*"
+# Towncrier min version comes from https://github.com/matrix-org/synapse/pull/3425. Rationale unclear.
+towncrier = ">=18.6.0rc1"
+
+# Used for checking the Poetry lockfile
+tomli = ">=1.2.3"
+
+# Used for checking the schema delta files
+sqlglot = ">=28.0.0"
 
 [tool.towncrier]
     package = "synapse"
@@ -260,15 +388,10 @@ select = [
     "G",
     # pyupgrade
     "UP006",
-    "UP007",
-    "UP045",
 ]
 extend-safe-fixes = [
     # pyupgrade rules compatible with Python >= 3.9
     "UP006",
-    "UP007",
-    # pyupgrade rules compatible with Python >= 3.10
-    "UP045",
     # Allow ruff to automatically fix trailing spaces within a multi-line string/comment.
     "W293"
 ]
@@ -291,88 +414,29 @@ line-ending = "auto"
 [tool.maturin]
 manifest-path = "rust/Cargo.toml"
 module-name = "synapse.synapse_rust"
-
-[tool.poetry]
-packages = [
-    { include = "synapse" },
+python-source = "."
+sdist-include = [
+    "AUTHORS.rst",
+    "book.toml",
+    "changelog.d",
+    "CHANGES.md",
+    "CONTRIBUTING.md",
+    "demo",
+    "docs",
+    "INSTALL.md",
+    "mypy.ini",
+    "scripts-dev",
+    "synmark",
+    "sytest-blacklist",
+    "tests",
+    "UPGRADE.rst",
+    "Cargo.toml",
+    "Cargo.lock",
+    "rust/Cargo.toml",
+    "rust/build.rs",
+    "rust/src/**",
 ]
-include = [
-    { path = "AUTHORS.rst", format = "sdist" },
-    { path = "book.toml", format = "sdist" },
-    { path = "changelog.d", format = "sdist" },
-    { path = "CHANGES.md", format = "sdist" },
-    { path = "CONTRIBUTING.md", format = "sdist" },
-    { path = "demo", format = "sdist" },
-    { path = "docs", format = "sdist" },
-    { path = "INSTALL.md", format = "sdist" },
-    { path = "mypy.ini", format = "sdist" },
-    { path = "scripts-dev", format = "sdist" },
-    { path = "synmark", format="sdist" },
-    { path = "sytest-blacklist", format = "sdist" },
-    { path = "tests", format = "sdist" },
-    { path = "UPGRADE.rst", format = "sdist" },
-    { path = "Cargo.toml", format = "sdist" },
-    { path = "Cargo.lock", format = "sdist" },
-    { path = "rust/Cargo.toml", format = "sdist" },
-    { path = "rust/build.rs", format = "sdist" },
-    { path = "rust/src/**", format = "sdist" },
-]
-exclude = [
-    { path = "synapse/*.so", format = "sdist"}
-]
-
-[tool.poetry.build]
-script = "build_rust.py"
-generate-setup-file = true
-
-[tool.poetry.group.dev.dependencies]
-# We pin development dependencies in poetry.lock so that our tests don't start
-# failing on new releases. Keeping lower bounds loose here means that dependabot
-# can bump versions without having to update the content-hash in the lockfile.
-# This helps prevents merge conflicts when running a batch of dependabot updates.
-ruff = "0.14.5"
-
-# Typechecking
-lxml-stubs = ">=0.4.0"
-mypy = "*"
-mypy-zope = "*"
-types-bleach = ">=4.1.0"
-types-jsonschema = ">=3.2.0"
-types-netaddr = ">=0.8.0.6"
-types-opentracing = ">=2.4.2"
-types-Pillow = ">=8.3.4"
-types-psycopg2 = ">=2.9.9"
-types-pyOpenSSL = ">=20.0.7"
-types-PyYAML = ">=5.4.10"
-types-requests = ">=2.26.0"
-types-setuptools = ">=57.4.0"
-
-# Dependencies which are exclusively required by unit test code. This is
-# NOT a list of all modules that are necessary to run the unit tests.
-# Tests assume that all optional dependencies are installed.
-#
-# If this is updated, don't forget to update the equivalent lines in
-# project.optional-dependencies.test.
-parameterized = ">=0.9.0"
-idna = ">=3.3"
-
-# The following are used by the release script
-click = ">=8.1.3"
-# GitPython was == 3.1.14; bumped to 3.1.20, the first release with type hints.
-GitPython = ">=3.1.20"
-markdown-it-py = ">=3.0.0"
-pygithub = ">=1.59"
-# The following are executed as commands by the release script.
-twine = "*"
-# Towncrier min version comes from https://github.com/matrix-org/synapse/pull/3425. Rationale unclear.
-towncrier = ">=18.6.0rc1"
-
-# Used for checking the Poetry lockfile
-tomli = ">=1.2.3"
-
-# Used for checking the schema delta files
-sqlglot = ">=28.0.0"
-
+sdist-exclude = ["synapse/*.so"]
 
 [build-system]
 # The upper bounds here are defensive, intended to prevent situations like
@@ -381,8 +445,8 @@ sqlglot = ">=28.0.0"
 # runtime errors caused by build system changes.
 # We are happy to raise these upper bounds upon request,
 # provided we check that it's safe to do so (i.e. that CI passes).
-requires = ["poetry-core>=2.0.0,<=2.1.3", "setuptools_rust>=1.3,<=1.11.1"]
-build-backend = "poetry.core.masonry.api"
+requires = ["maturin>=1.0,<2.0"]
+build-backend = "maturin"
 
 
 [tool.cibuildwheel]
@@ -407,9 +471,6 @@ skip = "cp3??t-* *i686* *macosx*"
 enable = "pypy"
 
 # We need a rust compiler.
-#
-# We temporarily pin Rust to 1.82.0 to work around
-# https://github.com/element-hq/synapse/issues/17988
 before-all =  "sh .ci/before_build_wheel.sh"
 environment= { PATH = "$PATH:$HOME/.cargo/bin" }
 
@@ -419,8 +480,3 @@ environment= { PATH = "$PATH:$HOME/.cargo/bin" }
 before-build = "rm -rf {project}/build"
 build-frontend = "build"
 test-command = "python -c 'from synapse.synapse_rust import sum_as_string; print(sum_as_string(1, 2))'"
-
-
-[tool.cibuildwheel.linux]
-# Wrap the repair command to correctly rename the built cpython wheels as ABI3.
-repair-wheel-command = "./.ci/scripts/auditwheel_wrapper.py -w {dest_dir} {wheel}"

scripts-dev/check_schema_delta.py

@@ -14,7 +14,6 @@ import sqlglot.expressions
 
 SCHEMA_FILE_REGEX = re.compile(r"^synapse/storage/schema/(.*)/delta/(.*)/(.*)$")
 
-
 # The base branch we want to check against. We use the main development branch
 # on the assumption that is what we are developing against.
 DEVELOP_BRANCH = "develop"

scripts-dev/release.py

@@ -32,7 +32,7 @@ import time
 import urllib.request
 from os import path
 from tempfile import TemporaryDirectory
-from typing import Any, Match
+from typing import Any
 
 import attr
 import click
@@ -968,10 +968,6 @@ def generate_and_write_changelog(
     new_changes = new_changes.replace(
         "No significant changes.", f"No significant changes since {current_version}."
     )
-    new_changes += build_dependabot_changelog(
-        repo,
-        current_version,
-    )
 
     # Prepend changes to changelog
     with open("CHANGES.md", "r+") as f:
@@ -986,49 +982,5 @@ def generate_and_write_changelog(
         os.remove(filename)
 
 
-def build_dependabot_changelog(repo: Repo, current_version: version.Version) -> str:
-    """Summarise dependabot commits between `current_version` and `release_branch`.
-
-    Returns an empty string if there have been no such commits; otherwise outputs a
-    third-level markdown header followed by an unordered list."""
-    last_release_commit = repo.tag("v" + str(current_version)).commit
-    rev_spec = f"{last_release_commit.hexsha}.."
-    commits = list(git.objects.Commit.iter_items(repo, rev_spec))
-    messages = []
-    for commit in reversed(commits):
-        if commit.author.name == "dependabot[bot]":
-            message: str | bytes = commit.message
-            if isinstance(message, bytes):
-                message = message.decode("utf-8")
-            messages.append(message.split("\n", maxsplit=1)[0])
-
-    if not messages:
-        print(f"No dependabot commits in range {rev_spec}", file=sys.stderr)
-        return ""
-
-    messages.sort()
-
-    def replacer(match: Match[str]) -> str:
-        desc = match.group(1)
-        number = match.group(2)
-        return f"* {desc}. ([\\#{number}](https://github.com/element-hq/synapse/issues/{number}))"
-
-    for i, message in enumerate(messages):
-        messages[i] = re.sub(r"(.*) \(#(\d+)\)$", replacer, message)
-    messages.insert(0, "### Updates to locked dependencies\n")
-    # Add an extra blank line to the bottom of the section
-    messages.append("")
-    return "\n".join(messages)
-
-
-@cli.command()
-@click.argument("since")
-def test_dependabot_changelog(since: str) -> None:
-    """Test building the dependabot changelog.
-
-    Summarises all dependabot commits between the SINCE tag and the current git HEAD."""
-    print(build_dependabot_changelog(git.Repo("."), version.Version(since)))
-
-
 if __name__ == "__main__":
     cli()

synapse/api/constants.py

@@ -29,6 +29,19 @@ from typing import Final
 # the max size of a (canonical-json-encoded) event
 MAX_PDU_SIZE = 65536
 
+# The maximum allowed size of an HTTP request.
+# Other than media uploads, the biggest request we expect to see is a fully-loaded
+# /federation/v1/send request.
+#
+# The main thing in such a request is up to 50 PDUs, and up to 100 EDUs. PDUs are
+# limited to 65536 bytes (possibly slightly more if the sender didn't use canonical
+# json encoding); there is no specced limit to EDUs (see
+# https://github.com/matrix-org/matrix-doc/issues/3121).
+#
+# in short, we somewhat arbitrarily limit requests to 200 * 64K (about 12.5M)
+#
+MAX_REQUEST_SIZE = 200 * MAX_PDU_SIZE
+
 # Max/min size of ints in canonical JSON
 CANONICALJSON_MAX_INT = (2**53) - 1
 CANONICALJSON_MIN_INT = -CANONICALJSON_MAX_INT

synapse/api/errors.py

@@ -856,6 +856,12 @@ class HttpResponseException(CodeMessageException):
         return ProxiedRequestError(self.code, errmsg, errcode, j)
 
 
+class HomeServerNotSetupException(Exception):
+    """
+    Raised when an operation is attempted on the HomeServer before setup() has been called.
+    """
+
+
 class ShadowBanError(Exception):
     """
     Raised when a shadow-banned user attempts to perform an action.

synapse/app/_base.py

@@ -36,12 +36,13 @@ from typing import (
     Awaitable,
     Callable,
     NoReturn,
+    Optional,
     cast,
 )
 from wsgiref.simple_server import WSGIServer
 
 from cryptography.utils import CryptographyDeprecationWarning
-from typing_extensions import ParamSpec
+from typing_extensions import ParamSpec, assert_never
 
 import twisted
 from twisted.internet import defer, error, reactor as _reactor
@@ -59,12 +60,17 @@ from twisted.python.threadpool import ThreadPool
 from twisted.web.resource import Resource
 
 import synapse.util.caches
-from synapse.api.constants import MAX_PDU_SIZE
+from synapse.api.constants import MAX_REQUEST_SIZE
 from synapse.app import check_bind_error
 from synapse.config import ConfigError
 from synapse.config._base import format_config_error
 from synapse.config.homeserver import HomeServerConfig
-from synapse.config.server import ListenerConfig, ManholeConfig, TCPListenerConfig
+from synapse.config.server import (
+    ListenerConfig,
+    ManholeConfig,
+    TCPListenerConfig,
+    UnixListenerConfig,
+)
 from synapse.crypto import context_factory
 from synapse.events.auto_accept_invites import InviteAutoAccepter
 from synapse.events.presence_router import load_legacy_presence_router
@@ -413,13 +419,44 @@ def listen_unix(
     ]
 
 
+class ListenerException(RuntimeError):
+    """
+    An exception raised when we fail to listen with the given `ListenerConfig`.
+
+    Attributes:
+        listener_config: The listener config that caused the exception.
+    """
+
+    def __init__(
+        self,
+        listener_config: ListenerConfig,
+    ):
+        listener_human_name = ""
+        port = ""
+        if isinstance(listener_config, TCPListenerConfig):
+            listener_human_name = "TCP port"
+            port = str(listener_config.port)
+        elif isinstance(listener_config, UnixListenerConfig):
+            listener_human_name = "unix socket"
+            port = listener_config.path
+        else:
+            assert_never(listener_config)
+
+        super().__init__(
+            "Failed to listen on %s (%s) with the given listener config: %s"
+            % (listener_human_name, port, listener_config)
+        )
+
+        self.listener_config = listener_config
+
+
 def listen_http(
     hs: "HomeServer",
     listener_config: ListenerConfig,
     root_resource: Resource,
     version_string: str,
     max_request_body_size: int,
-    context_factory: IOpenSSLContextFactory | None,
+    context_factory: Optional[IOpenSSLContextFactory],
     reactor: ISynapseReactor = reactor,
 ) -> list[Port]:
     """
@@ -447,39 +484,55 @@ def listen_http(
         hs=hs,
     )
 
-    if isinstance(listener_config, TCPListenerConfig):
-        if listener_config.is_tls():
-            # refresh_certificate should have been called before this.
-            assert context_factory is not None
-            ports = listen_ssl(
-                listener_config.bind_addresses,
-                listener_config.port,
-                site,
-                context_factory,
-                reactor=reactor,
+    try:
+        if isinstance(listener_config, TCPListenerConfig):
+            if listener_config.is_tls():
+                # refresh_certificate should have been called before this.
+                assert context_factory is not None
+                ports = listen_ssl(
+                    listener_config.bind_addresses,
+                    listener_config.port,
+                    site,
+                    context_factory,
+                    reactor=reactor,
+                )
+                logger.info(
+                    "Synapse now listening on TCP port %d (TLS)", listener_config.port
+                )
+            else:
+                ports = listen_tcp(
+                    listener_config.bind_addresses,
+                    listener_config.port,
+                    site,
+                    reactor=reactor,
+                )
+                logger.info(
+                    "Synapse now listening on TCP port %d", listener_config.port
+                )
+
+        elif isinstance(listener_config, UnixListenerConfig):
+            ports = listen_unix(
+                listener_config.path, listener_config.mode, site, reactor=reactor
             )
+            # getHost() returns a UNIXAddress which contains an instance variable of 'name'
+            # encoded as a byte string. Decode as utf-8 so pretty.
             logger.info(
-                "Synapse now listening on TCP port %d (TLS)", listener_config.port
+                "Synapse now listening on Unix Socket at: %s",
+                ports[0].getHost().name.decode("utf-8"),
             )
         else:
-            ports = listen_tcp(
-                listener_config.bind_addresses,
-                listener_config.port,
-                site,
-                reactor=reactor,
-            )
-            logger.info("Synapse now listening on TCP port %d", listener_config.port)
-
-    else:
-        ports = listen_unix(
-            listener_config.path, listener_config.mode, site, reactor=reactor
-        )
-        # getHost() returns a UNIXAddress which contains an instance variable of 'name'
-        # encoded as a byte string. Decode as utf-8 so pretty.
-        logger.info(
-            "Synapse now listening on Unix Socket at: %s",
-            ports[0].getHost().name.decode("utf-8"),
-        )
+            assert_never(listener_config)
+    except Exception as exc:
+        # The Twisted interface says that "Users should not call this function
+        # themselves!" but this appears to be the correct/only way handle proper cleanup
+        # of the site when things go wrong. In the normal case, a `Port` is created
+        # which we can call `Port.stopListening()` on to do the same thing (but no
+        # `Port` is created when an error occurs).
+        #
+        # We use `site.stopFactory()` instead of `site.doStop()` as the latter assumes
+        # that `site.doStart()` was called (which won't be the case if an error occurs).
+        site.stopFactory()
+        raise ListenerException(listener_config) from exc
 
     return ports
 
@@ -843,17 +896,8 @@ def sdnotify(state: bytes) -> None:
 def max_request_body_size(config: HomeServerConfig) -> int:
     """Get a suitable maximum size for incoming HTTP requests"""
 
-    # Other than media uploads, the biggest request we expect to see is a fully-loaded
-    # /federation/v1/send request.
-    #
-    # The main thing in such a request is up to 50 PDUs, and up to 100 EDUs. PDUs are
-    # limited to 65536 bytes (possibly slightly more if the sender didn't use canonical
-    # json encoding); there is no specced limit to EDUs (see
-    # https://github.com/matrix-org/matrix-doc/issues/3121).
-    #
-    # in short, we somewhat arbitrarily limit requests to 200 * 64K (about 12.5M)
-    #
-    max_request_size = 200 * MAX_PDU_SIZE
+    # Baseline default for any request that isn't configured in the homeserver config
+    max_request_size = MAX_REQUEST_SIZE
 
     # if we have a media repo enabled, we may need to allow larger uploads than that
     if config.media.can_load_media_repo:

synapse/app/admin_cmd.py

@@ -24,7 +24,7 @@ import logging
 import os
 import sys
 import tempfile
-from typing import Mapping, Sequence
+from typing import Mapping, Optional, Sequence
 
 from twisted.internet import defer, task
 
@@ -291,7 +291,7 @@ def load_config(argv_options: list[str]) -> tuple[HomeServerConfig, argparse.Nam
 
 def create_homeserver(
     config: HomeServerConfig,
-    reactor: ISynapseReactor | None = None,
+    reactor: Optional[ISynapseReactor] = None,
 ) -> AdminCmdServer:
     """
     Create a homeserver instance for the Synapse admin command process.

synapse/app/generic_worker.py

@@ -21,6 +21,7 @@
 #
 import logging
 import sys
+from typing import Optional
 
 from twisted.web.resource import Resource
 
@@ -335,7 +336,7 @@ def load_config(argv_options: list[str]) -> HomeServerConfig:
 
 def create_homeserver(
     config: HomeServerConfig,
-    reactor: ISynapseReactor | None = None,
+    reactor: Optional[ISynapseReactor] = None,
 ) -> GenericWorkerServer:
     """
     Create a homeserver instance for the Synapse worker process.

synapse/app/homeserver.py

@@ -22,7 +22,7 @@
 import logging
 import os
 import sys
-from typing import Iterable
+from typing import Iterable, Optional
 
 from twisted.internet.tcp import Port
 from twisted.web.resource import EncodingResourceWrapper, Resource
@@ -350,7 +350,7 @@ def load_or_generate_config(argv_options: list[str]) -> HomeServerConfig:
 
 def create_homeserver(
     config: HomeServerConfig,
-    reactor: ISynapseReactor | None = None,
+    reactor: Optional[ISynapseReactor] = None,
 ) -> SynapseHomeServer:
     """
     Create a homeserver instance for the Synapse main process.

synapse/crypto/keyring.py

@@ -21,6 +21,7 @@
 
 import abc
 import logging
+from contextlib import ExitStack
 from typing import TYPE_CHECKING, Callable, Iterable
 
 import attr
@@ -150,57 +151,81 @@ class Keyring:
     """
 
     def __init__(
-        self, hs: "HomeServer", key_fetchers: "Iterable[KeyFetcher] | None" = None
+        self,
+        hs: "HomeServer",
+        test_only_key_fetchers: "list[KeyFetcher] | None" = None,
     ):
-        self.server_name = hs.hostname
+        """
+        Args:
+            hs: The HomeServer instance
+            test_only_key_fetchers: Dependency injection for tests only. If provided,
+                these key fetchers will be used instead of the default ones.
+        """
+        # Clean-up to avoid partial initialization leaving behind references.
+        with ExitStack() as exit:
+            self.server_name = hs.hostname
 
-        if key_fetchers is None:
-            # Always fetch keys from the database.
-            mutable_key_fetchers: list[KeyFetcher] = [StoreKeyFetcher(hs)]
-            # Fetch keys from configured trusted key servers, if any exist.
-            key_servers = hs.config.key.key_servers
-            if key_servers:
-                mutable_key_fetchers.append(PerspectivesKeyFetcher(hs))
-            # Finally, fetch keys from the origin server directly.
-            mutable_key_fetchers.append(ServerKeyFetcher(hs))
+            self._key_fetchers: list[KeyFetcher] = []
+            if test_only_key_fetchers is None:
+                # Always fetch keys from the database.
+                store_key_fetcher = StoreKeyFetcher(hs)
+                exit.callback(store_key_fetcher.shutdown)
+                self._key_fetchers.append(store_key_fetcher)
 
-            self._key_fetchers: Iterable[KeyFetcher] = tuple(mutable_key_fetchers)
-        else:
-            self._key_fetchers = key_fetchers
+                # Fetch keys from configured trusted key servers, if any exist.
+                key_servers = hs.config.key.key_servers
+                if key_servers:
+                    perspectives_key_fetcher = PerspectivesKeyFetcher(hs)
+                    exit.callback(perspectives_key_fetcher.shutdown)
+                    self._key_fetchers.append(perspectives_key_fetcher)
 
-        self._fetch_keys_queue: BatchingQueue[
-            _FetchKeyRequest, dict[str, dict[str, FetchKeyResult]]
-        ] = BatchingQueue(
-            name="keyring_server",
-            hs=hs,
-            clock=hs.get_clock(),
-            # The method called to fetch each key
-            process_batch_callback=self._inner_fetch_key_requests,
-        )
+                # Finally, fetch keys from the origin server directly.
+                server_key_fetcher = ServerKeyFetcher(hs)
+                exit.callback(server_key_fetcher.shutdown)
+                self._key_fetchers.append(server_key_fetcher)
+            else:
+                self._key_fetchers = test_only_key_fetchers
 
-        self._is_mine_server_name = hs.is_mine_server_name
+            self._fetch_keys_queue: BatchingQueue[
+                _FetchKeyRequest, dict[str, dict[str, FetchKeyResult]]
+            ] = BatchingQueue(
+                name="keyring_server",
+                hs=hs,
+                clock=hs.get_clock(),
+                # The method called to fetch each key
+                process_batch_callback=self._inner_fetch_key_requests,
+            )
+            exit.callback(self._fetch_keys_queue.shutdown)
 
-        # build a FetchKeyResult for each of our own keys, to shortcircuit the
-        # fetcher.
-        self._local_verify_keys: dict[str, FetchKeyResult] = {}
-        for key_id, key in hs.config.key.old_signing_keys.items():
-            self._local_verify_keys[key_id] = FetchKeyResult(
-                verify_key=key, valid_until_ts=key.expired
+            self._is_mine_server_name = hs.is_mine_server_name
+
+            # build a FetchKeyResult for each of our own keys, to shortcircuit the
+            # fetcher.
+            self._local_verify_keys: dict[str, FetchKeyResult] = {}
+            for key_id, key in hs.config.key.old_signing_keys.items():
+                self._local_verify_keys[key_id] = FetchKeyResult(
+                    verify_key=key, valid_until_ts=key.expired
+                )
+
+            vk = get_verify_key(hs.signing_key)
+            self._local_verify_keys[f"{vk.alg}:{vk.version}"] = FetchKeyResult(
+                verify_key=vk,
+                valid_until_ts=2**63,  # fake future timestamp
             )
 
-        vk = get_verify_key(hs.signing_key)
-        self._local_verify_keys[f"{vk.alg}:{vk.version}"] = FetchKeyResult(
-            verify_key=vk,
-            valid_until_ts=2**63,  # fake future timestamp
-        )
+            # We reached the end of the block which means everything was successful, so
+            # no exit handlers are needed (remove them all).
+            exit.pop_all()
 
     def shutdown(self) -> None:
         """
         Prepares the KeyRing for garbage collection by shutting down it's queues.
         """
         self._fetch_keys_queue.shutdown()
+
         for key_fetcher in self._key_fetchers:
             key_fetcher.shutdown()
+        self._key_fetchers.clear()
 
     async def verify_json_for_server(
         self,
@@ -521,9 +546,21 @@ class StoreKeyFetcher(KeyFetcher):
     """KeyFetcher impl which fetches keys from our data store"""
 
     def __init__(self, hs: "HomeServer"):
-        super().__init__(hs)
+        # Clean-up to avoid partial initialization leaving behind references.
+        with ExitStack() as exit:
+            super().__init__(hs)
+            # `KeyFetcher` keeps a reference to `hs` which we need to clean up if
+            # something goes wrong so we can cleanly shutdown the homeserver.
+            exit.callback(super().shutdown)
 
-        self.store = hs.get_datastores().main
+            # An error can be raised here if someone tried to create a `StoreKeyFetcher`
+            # before the homeserver is fully set up (`HomeServerNotSetupException:
+            # HomeServer.setup must be called before getting datastores`).
+            self.store = hs.get_datastores().main
+
+            # We reached the end of the block which means everything was successful, so
+            # no exit handlers are needed (remove them all).
+            exit.pop_all()
 
     async def _fetch_keys(
         self, keys_to_fetch: list[_FetchKeyRequest]
@@ -543,9 +580,21 @@ class StoreKeyFetcher(KeyFetcher):
 
 class BaseV2KeyFetcher(KeyFetcher):
     def __init__(self, hs: "HomeServer"):
-        super().__init__(hs)
+        # Clean-up to avoid partial initialization leaving behind references.
+        with ExitStack() as exit:
+            super().__init__(hs)
+            # `KeyFetcher` keeps a reference to `hs` which we need to clean up if
+            # something goes wrong so we can cleanly shutdown the homeserver.
+            exit.callback(super().shutdown)
 
-        self.store = hs.get_datastores().main
+            # An error can be raised here if someone tried to create a `StoreKeyFetcher`
+            # before the homeserver is fully set up (`HomeServerNotSetupException:
+            # HomeServer.setup must be called before getting datastores`).
+            self.store = hs.get_datastores().main
+
+            # We reached the end of the block which means everything was successful, so
+            # no exit handlers are needed (remove them all).
+            exit.pop_all()
 
     async def process_v2_response(
         self, from_server: str, response_json: JsonDict, time_added_ms: int

synapse/handlers/delayed_events.py

@@ -13,7 +13,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING
+from typing import TYPE_CHECKING, Optional
 
 from twisted.internet.interfaces import IDelayedCall
 
@@ -74,7 +74,7 @@ class DelayedEventsHandler:
             cfg=self._config.ratelimiting.rc_delayed_event_mgmt,
         )
 
-        self._next_delayed_event_call: IDelayedCall | None = None
+        self._next_delayed_event_call: Optional[IDelayedCall] = None
 
         # The current position in the current_state_delta stream
         self._event_pos: int | None = None

synapse/handlers/message.py

@@ -22,7 +22,7 @@
 import logging
 import random
 from http import HTTPStatus
-from typing import TYPE_CHECKING, Any, Mapping, Sequence
+from typing import TYPE_CHECKING, Any, Mapping, Optional, Sequence
 
 from canonicaljson import encode_canonical_json
 
@@ -111,7 +111,7 @@ class MessageHandler:
 
         # The scheduled call to self._expire_event. None if no call is currently
         # scheduled.
-        self._scheduled_expiry: IDelayedCall | None = None
+        self._scheduled_expiry: Optional[IDelayedCall] = None
 
         if not hs.config.worker.worker_app:
             self.hs.run_as_background_process(

synapse/handlers/room_member.py

@@ -874,7 +874,7 @@ class RoomMemberHandler(metaclass=abc.ABCMeta):
             if target_id == self._server_notices_mxid:
                 raise SynapseError(HTTPStatus.FORBIDDEN, "Cannot invite this user")
 
-            block_invite_result = None
+            block_invite_result: tuple[Codes, dict] | None = None
 
             if (
                 self._server_notices_mxid is not None

synapse/handlers/sliding_sync/__init__.py

@@ -17,6 +17,7 @@ import logging
 from itertools import chain
 from typing import TYPE_CHECKING, AbstractSet, Mapping
 
+import attr
 from prometheus_client import Histogram
 from typing_extensions import assert_never
 
@@ -62,6 +63,7 @@ from synapse.types.handlers.sliding_sync import (
     HaveSentRoomFlag,
     MutablePerConnectionState,
     PerConnectionState,
+    RoomLazyMembershipChanges,
     RoomSyncConfig,
     SlidingSyncConfig,
     SlidingSyncResult,
@@ -106,7 +108,7 @@ class SlidingSyncHandler:
         self.rooms_to_exclude_globally = hs.config.server.rooms_to_exclude_from_sync
         self.is_mine_id = hs.is_mine_id
 
-        self.connection_store = SlidingSyncConnectionStore(self.store)
+        self.connection_store = SlidingSyncConnectionStore(self.clock, self.store)
         self.extensions = SlidingSyncExtensionHandler(hs)
         self.room_lists = SlidingSyncRoomLists(hs)
 
@@ -981,14 +983,15 @@ class SlidingSyncHandler:
         #
         # Calculate the `StateFilter` based on the `required_state` for the room
         required_state_filter = StateFilter.none()
-        # The requested `required_state_map` with the lazy membership expanded and
-        # `$ME` replaced with the user's ID. This allows us to see what membership we've
-        # sent down to the client in the next request.
-        #
-        # Make a copy so we can modify it. Still need to be careful to make a copy of
-        # the state key sets if we want to add/remove from them. We could make a deep
-        # copy but this saves us some work.
-        expanded_required_state_map = dict(room_sync_config.required_state_map)
+
+        # Keep track of which users' state we may need to fetch. We split this
+        # into explicit users and lazy loaded users.
+        explicit_user_state = set()
+        lazy_load_user_ids = set()
+
+        # Whether lazy-loading of room members is enabled.
+        lazy_load_room_members = False
+
         if room_membership_for_user_at_to_token.membership not in (
             Membership.INVITE,
             Membership.KNOCK,
@@ -1036,7 +1039,6 @@ class SlidingSyncHandler:
             else:
                 required_state_types: list[tuple[str, str | None]] = []
                 num_wild_state_keys = 0
-                lazy_load_room_members = False
                 num_others = 0
                 for (
                     state_type,
@@ -1068,43 +1070,60 @@ class SlidingSyncHandler:
                                             timeline_event.state_key
                                         )
 
+                            # The client needs to know the membership of everyone in
+                            # the timeline we're returning.
+                            lazy_load_user_ids.update(timeline_membership)
+
                             # Update the required state filter so we pick up the new
                             # membership
-                            for user_id in timeline_membership:
-                                required_state_types.append(
-                                    (EventTypes.Member, user_id)
-                                )
+                            if limited or initial:
+                                # If the timeline is limited, we only need to
+                                # return the membership changes for people in
+                                # the timeline.
+                                for user_id in timeline_membership:
+                                    required_state_types.append(
+                                        (EventTypes.Member, user_id)
+                                    )
+                            else:
+                                # For non-limited timelines we always return all
+                                # membership changes. This is so that clients
+                                # who have fetched the full membership list
+                                # already can continue to maintain it for
+                                # non-limited syncs.
+                                #
+                                # This assumes that for non-limited syncs there
+                                # won't be many membership changes that wouldn't
+                                # have been included already (this can only
+                                # happen if membership state was rolled back due
+                                # to state resolution anyway).
+                                #
+                                # `None` is a wildcard in the `StateFilter`
+                                required_state_types.append((EventTypes.Member, None))
 
-                            # Add an explicit entry for each user in the timeline
-                            #
-                            # Make a new set or copy of the state key set so we can
-                            # modify it without affecting the original
-                            # `required_state_map`
-                            expanded_required_state_map[EventTypes.Member] = (
-                                expanded_required_state_map.get(
-                                    EventTypes.Member, set()
+                                # Record the extra members we're returning.
+                                lazy_load_user_ids.update(
+                                    state_key
+                                    for event_type, state_key in room_state_delta_id_map
+                                    if event_type == EventTypes.Member
                                 )
-                                | timeline_membership
-                            )
-                        elif state_key == StateValues.ME:
+                        else:
                             num_others += 1
-                            required_state_types.append((state_type, user.to_string()))
+
                             # Replace `$ME` with the user's ID so we can deduplicate
                             # when someone requests the same state with `$ME` or with
                             # their user ID.
-                            #
-                            # Make a new set or copy of the state key set so we can
-                            # modify it without affecting the original
-                            # `required_state_map`
-                            expanded_required_state_map[EventTypes.Member] = (
-                                expanded_required_state_map.get(
-                                    EventTypes.Member, set()
-                                )
-                                | {user.to_string()}
+                            normalized_state_key = state_key
+                            if state_key == StateValues.ME:
+                                normalized_state_key = user.to_string()
+
+                            if state_type == EventTypes.Member:
+                                # Also track explicitly requested member state for
+                                # lazy membership tracking.
+                                explicit_user_state.add(normalized_state_key)
+
+                            required_state_types.append(
+                                (state_type, normalized_state_key)
                             )
-                        else:
-                            num_others += 1
-                            required_state_types.append((state_type, state_key))
 
                 set_tag(
                     SynapseTags.FUNC_ARG_PREFIX
@@ -1122,6 +1141,10 @@ class SlidingSyncHandler:
 
                 required_state_filter = StateFilter.from_types(required_state_types)
 
+        # Remove any explicitly requested user state from the lazy-loaded set,
+        # as we track them separately.
+        lazy_load_user_ids -= explicit_user_state
+
         # We need this base set of info for the response so let's just fetch it along
         # with the `required_state` for the room
         hero_room_state = [
@@ -1149,6 +1172,22 @@ class SlidingSyncHandler:
         # We can return all of the state that was requested if this was the first
         # time we've sent the room down this connection.
         room_state: StateMap[EventBase] = {}
+
+        # Includes the state for the heroes if we need them (may contain other
+        # state as well).
+        hero_membership_state: StateMap[EventBase] = {}
+
+        # By default, we mark all `lazy_load_user_ids` as being sent down
+        # for the first time in this sync. We later check if we sent any of them
+        # down previously and update `returned_user_id_to_last_seen_ts_map` if
+        # we have.
+        returned_user_id_to_last_seen_ts_map = {}
+        if lazy_load_room_members:
+            returned_user_id_to_last_seen_ts_map = dict.fromkeys(lazy_load_user_ids)
+        new_connection_state.room_lazy_membership[room_id] = RoomLazyMembershipChanges(
+            returned_user_id_to_last_seen_ts_map=returned_user_id_to_last_seen_ts_map
+        )
+
         if initial:
             room_state = await self.get_current_state_at(
                 room_id=room_id,
@@ -1156,28 +1195,97 @@ class SlidingSyncHandler:
                 state_filter=state_filter,
                 to_token=to_token,
             )
+
+            # The `room_state` includes the hero membership state if needed.
+            # We'll later filter this down so we don't need to do so here.
+            hero_membership_state = room_state
         else:
+            assert from_token is not None
             assert from_bound is not None
 
             if prev_room_sync_config is not None:
+                # Define `all_required_user_state` as all user state we want, which
+                # is the explicitly requested members, any needed for lazy
+                # loading, and users whose membership has changed.
+                all_required_user_state = explicit_user_state | lazy_load_user_ids
+                for state_type, state_key in room_state_delta_id_map:
+                    if state_type == EventTypes.Member:
+                        all_required_user_state.add(state_key)
+
+                # We need to know what user state we previously sent down the
+                # connection so we can determine what has changed.
+                #
+                # We need to fetch all users whose memberships we may want
+                # to send down this sync. This includes (and matches
+                # `all_required_user_state`):
+                #   1. Explicitly requested user state
+                #   2. Lazy loaded members, i.e. users who appear in the
+                #      timeline.
+                #   3. The users whose membership has changed in the room, i.e.
+                #      in the state deltas.
+                #
+                # This is to correctly handle the cases where a user was
+                # previously sent down as a lazy loaded member:
+                #   - and is now explicitly requested (so shouldn't be sent down
+                #     again); or
+                #   - their membership has changed (so we need to invalidate
+                #     their entry in the lazy loaded table if we don't send the
+                #     change down).
+                if all_required_user_state:
+                    previously_returned_user_to_last_seen = (
+                        await self.store.get_sliding_sync_connection_lazy_members(
+                            connection_position=from_token.connection_position,
+                            room_id=room_id,
+                            user_ids=all_required_user_state,
+                        )
+                    )
+
+                    # Update the room lazy membership changes to track which
+                    # lazy loaded members were needed for this sync. This is so
+                    # that we can correctly track the last time we sent down
+                    # users' membership (and so can evict old membership state
+                    # from the DB tables).
+                    returned_user_id_to_last_seen_ts_map.update(
+                        (user_id, timestamp)
+                        for user_id, timestamp in previously_returned_user_to_last_seen.items()
+                        if user_id in lazy_load_user_ids
+                    )
+                else:
+                    previously_returned_user_to_last_seen = {}
+
                 # Check if there are any changes to the required state config
                 # that we need to handle.
-                changed_required_state_map, added_state_filter = (
-                    _required_state_changes(
-                        user.to_string(),
-                        prev_required_state_map=prev_room_sync_config.required_state_map,
-                        request_required_state_map=expanded_required_state_map,
-                        state_deltas=room_state_delta_id_map,
-                    )
+                changes_return = _required_state_changes(
+                    user.to_string(),
+                    prev_required_state_map=prev_room_sync_config.required_state_map,
+                    request_required_state_map=room_sync_config.required_state_map,
+                    previously_returned_lazy_user_ids=previously_returned_user_to_last_seen.keys(),
+                    request_lazy_load_user_ids=lazy_load_user_ids,
+                    state_deltas=room_state_delta_id_map,
                 )
+                changed_required_state_map = changes_return.changed_required_state_map
 
-                if added_state_filter:
+                new_connection_state.room_lazy_membership[
+                    room_id
+                ].invalidated_user_ids = changes_return.lazy_members_invalidated
+
+                # Add any previously returned explicit memberships to the lazy
+                # loaded table. This happens when a client requested explicit
+                # members and then converted them to lazy loading.
+                for user_id in changes_return.extra_users_to_add_to_lazy_cache:
+                    # We don't know the right timestamp to use here, as we don't
+                    # know the last time we would have sent the membership down.
+                    # So we don't overwrite it if we have a timestamp already,
+                    # and fallback to `None` (which means now) if we don't.
+                    returned_user_id_to_last_seen_ts_map.setdefault(user_id, None)
+
+                if changes_return.added_state_filter:
                     # Some state entries got added, so we pull out the current
                     # state for them. If we don't do this we'd only send down new deltas.
                     state_ids = await self.get_current_state_ids_at(
                         room_id=room_id,
                         room_membership_for_user_at_to_token=room_membership_for_user_at_to_token,
-                        state_filter=added_state_filter,
+                        state_filter=changes_return.added_state_filter,
                         to_token=to_token,
                     )
                     room_state_delta_id_map.update(state_ids)
@@ -1189,6 +1297,7 @@ class SlidingSyncHandler:
 
             # If the membership changed and we have to get heroes, get the remaining
             # heroes from the state
+            hero_membership_state = {}
             if hero_user_ids:
                 hero_membership_state = await self.get_current_state_at(
                     room_id=room_id,
@@ -1196,7 +1305,6 @@ class SlidingSyncHandler:
                     state_filter=StateFilter.from_types(hero_room_state),
                     to_token=to_token,
                 )
-                room_state.update(hero_membership_state)
 
         required_room_state: StateMap[EventBase] = {}
         if required_state_filter != StateFilter.none():
@@ -1219,7 +1327,7 @@ class SlidingSyncHandler:
         # Assemble heroes: extract the info from the state we just fetched
         heroes: list[SlidingSyncResult.RoomResult.StrippedHero] = []
         for hero_user_id in hero_user_ids:
-            member_event = room_state.get((EventTypes.Member, hero_user_id))
+            member_event = hero_membership_state.get((EventTypes.Member, hero_user_id))
             if member_event is not None:
                 heroes.append(
                     SlidingSyncResult.RoomResult.StrippedHero(
@@ -1281,7 +1389,7 @@ class SlidingSyncHandler:
             bump_stamp = 0
 
         room_sync_required_state_map_to_persist: Mapping[str, AbstractSet[str]] = (
-            expanded_required_state_map
+            room_sync_config.required_state_map
         )
         if changed_required_state_map:
             room_sync_required_state_map_to_persist = changed_required_state_map
@@ -1471,13 +1579,37 @@ class SlidingSyncHandler:
             return None
 
 
+@attr.s(auto_attribs=True)
+class _RequiredStateChangesReturn:
+    """Return type for _required_state_changes."""
+
+    changed_required_state_map: Mapping[str, AbstractSet[str]] | None
+    """The updated required state map to store in the room config, or None if
+    there is no change."""
+
+    added_state_filter: StateFilter
+    """The state filter to use to fetch any additional current state that needs
+    to be returned to the client."""
+
+    extra_users_to_add_to_lazy_cache: AbstractSet[str] = frozenset()
+    """The set of user IDs we should add to the lazy members cache that we had
+    previously returned. Handles the case where a user was previously sent down
+    explicitly but is now being lazy loaded."""
+
+    lazy_members_invalidated: AbstractSet[str] = frozenset()
+    """The set of user IDs whose membership has changed but we didn't send down,
+    so we need to invalidate them from the cache."""
+
+
 def _required_state_changes(
     user_id: str,
     *,
     prev_required_state_map: Mapping[str, AbstractSet[str]],
     request_required_state_map: Mapping[str, AbstractSet[str]],
+    previously_returned_lazy_user_ids: AbstractSet[str],
+    request_lazy_load_user_ids: AbstractSet[str],
     state_deltas: StateMap[str],
-) -> tuple[Mapping[str, AbstractSet[str]] | None, StateFilter]:
+) -> _RequiredStateChangesReturn:
     """Calculates the changes between the required state room config from the
     previous requests compared with the current request.
 
@@ -1491,14 +1623,62 @@ def _required_state_changes(
     added, removed and then added again to the required state. In that case we
     only want to re-send that entry down sync if it has changed.
 
-    Returns:
-        A 2-tuple of updated required state config (or None if there is no update)
-        and the state filter to use to fetch extra current state that we need to
-        return.
+    Args:
+        user_id: The user ID of the user making the request.
+        prev_required_state_map: The required state map from the previous
+            request.
+        request_required_state_map: The required state map from the current
+            request.
+        previously_returned_lazy_user_ids: The set of user IDs whose membership
+            we have previously returned to the client due to lazy loading. This
+            is filtered to only include users who have either sent events in the
+            `timeline`, `required_state` or whose membership changed.
+        request_lazy_load_user_ids: The set of user IDs whose lazy-loaded
+            membership is required for this request.
+        state_deltas: The state deltas in the room in the request token range,
+            considering user membership. See `get_current_state_deltas_for_room`
+            for more details.
     """
+
+    # First we find any lazy members that have been invalidated due to state
+    # changes that we are not sending down.
+    lazy_members_invalidated = set()
+    for event_type, state_key in state_deltas:
+        if event_type != EventTypes.Member:
+            continue
+
+        if state_key in request_lazy_load_user_ids:
+            # Because it's part of the `request_lazy_load_user_ids`, we're going to
+            # send this member change down.
+            continue
+
+        if state_key not in previously_returned_lazy_user_ids:
+            # We've not previously returned this member so nothing to
+            # invalidate.
+            continue
+
+        lazy_members_invalidated.add(state_key)
+
     if prev_required_state_map == request_required_state_map:
-        # There has been no change. Return immediately.
-        return None, StateFilter.none()
+        # There has been no change in state, just need to check lazy members.
+        newly_returned_lazy_members = (
+            request_lazy_load_user_ids - previously_returned_lazy_user_ids
+        )
+        if newly_returned_lazy_members:
+            # There are some new lazy members we need to fetch.
+            added_types: list[tuple[str, str | None]] = []
+            for new_user_id in newly_returned_lazy_members:
+                added_types.append((EventTypes.Member, new_user_id))
+
+            added_state_filter = StateFilter.from_types(added_types)
+        else:
+            added_state_filter = StateFilter.none()
+
+        return _RequiredStateChangesReturn(
+            changed_required_state_map=None,
+            added_state_filter=added_state_filter,
+            lazy_members_invalidated=lazy_members_invalidated,
+        )
 
     prev_wildcard = prev_required_state_map.get(StateValues.WILDCARD, set())
     request_wildcard = request_required_state_map.get(StateValues.WILDCARD, set())
@@ -1508,17 +1688,29 @@ def _required_state_changes(
     # already fetching everything, we don't have to fetch anything now that they've
     # narrowed.
     if StateValues.WILDCARD in prev_wildcard:
-        return request_required_state_map, StateFilter.none()
+        return _RequiredStateChangesReturn(
+            changed_required_state_map=request_required_state_map,
+            added_state_filter=StateFilter.none(),
+            lazy_members_invalidated=lazy_members_invalidated,
+        )
 
     # If a event type wildcard has been added or removed we don't try and do
     # anything fancy, and instead always update the effective room required
     # state config to match the request.
     if request_wildcard - prev_wildcard:
         # Some keys were added, so we need to fetch everything
-        return request_required_state_map, StateFilter.all()
+        return _RequiredStateChangesReturn(
+            changed_required_state_map=request_required_state_map,
+            added_state_filter=StateFilter.all(),
+            lazy_members_invalidated=lazy_members_invalidated,
+        )
     if prev_wildcard - request_wildcard:
         # Keys were only removed, so we don't have to fetch everything.
-        return request_required_state_map, StateFilter.none()
+        return _RequiredStateChangesReturn(
+            changed_required_state_map=request_required_state_map,
+            added_state_filter=StateFilter.none(),
+            lazy_members_invalidated=lazy_members_invalidated,
+        )
 
     # Contains updates to the required state map compared with the previous room
     # config. This has the same format as `RoomSyncConfig.required_state`
@@ -1550,6 +1742,17 @@ def _required_state_changes(
             # Nothing *added*, so we skip. Removals happen below.
             continue
 
+        # Handle the special case of adding `$LAZY` membership, where we want to
+        # always record the change to be lazy loading, as we immediately start
+        # using the lazy loading tables so there is no point *not* recording the
+        # change to lazy load in the effective room config.
+        if event_type == EventTypes.Member:
+            old_state_key_lazy = StateValues.LAZY in old_state_keys
+            request_state_key_lazy = StateValues.LAZY in request_state_keys
+            if not old_state_key_lazy and request_state_key_lazy:
+                changes[event_type] = request_state_keys
+                continue
+
         # We only remove state keys from the effective state if they've been
         # removed from the request *and* the state has changed. This ensures
         # that if a client removes and then re-adds a state key, we only send
@@ -1620,9 +1823,31 @@ def _required_state_changes(
                     # LAZY values should also be ignore for event types that are
                     # not membership.
                     pass
+                elif event_type == EventTypes.Member:
+                    if state_key not in previously_returned_lazy_user_ids:
+                        # Only add *explicit* members we haven't previously sent
+                        # down.
+                        added.append((event_type, state_key))
                 else:
                     added.append((event_type, state_key))
 
+    previously_required_state_members = set(
+        prev_required_state_map.get(EventTypes.Member, ())
+    )
+    if StateValues.ME in previously_required_state_members:
+        previously_required_state_members.add(user_id)
+
+    # We also need to pull out any lazy members that are now required but
+    # haven't previously been returned.
+    for required_user_id in (
+        request_lazy_load_user_ids
+        # Remove previously returned users
+        - previously_returned_lazy_user_ids
+        # Exclude previously explicitly requested members.
+        - previously_required_state_members
+    ):
+        added.append((EventTypes.Member, required_user_id))
+
     added_state_filter = StateFilter.from_types(added)
 
     # Figure out what changes we need to apply to the effective required state
@@ -1663,13 +1888,25 @@ def _required_state_changes(
             changes[event_type] = request_state_keys
             continue
 
+        # When handling $LAZY membership, we want to either a) not update the
+        # state or b) update it to match the request. This is to avoid churn of
+        # the effective required state for rooms (we deduplicate required state
+        # between rooms), and because we can store the previously returned
+        # explicit memberships with the lazy loaded memberships.
         if event_type == EventTypes.Member:
             old_state_key_lazy = StateValues.LAZY in old_state_keys
             request_state_key_lazy = StateValues.LAZY in request_state_keys
+            has_lazy = old_state_key_lazy or request_state_key_lazy
 
+            # If a "$LAZY" has been added or removed we always update to match
+            # the request.
             if old_state_key_lazy != request_state_key_lazy:
-                # If a "$LAZY" has been added or removed we always update the effective room
-                # required state config to match the request.
+                changes[event_type] = request_state_keys
+                continue
+
+            # Or if we have lazy membership and there are invalidated
+            # explicit memberships.
+            if has_lazy and invalidated_state_keys:
                 changes[event_type] = request_state_keys
                 continue
 
@@ -1684,6 +1921,28 @@ def _required_state_changes(
         if invalidated_state_keys:
             changes[event_type] = old_state_keys - invalidated_state_keys
 
+    # Check for any explicit membership changes that were removed that we can
+    # add to the lazy members previously returned. This is so that we don't
+    # return a user due to lazy loading if they were previously returned as an
+    # explicit membership.
+    users_to_add_to_lazy_cache: set[str] = set()
+
+    membership_changes = changes.get(EventTypes.Member, set())
+    if membership_changes and StateValues.LAZY in request_state_keys:
+        for state_key in prev_required_state_map.get(EventTypes.Member, set()):
+            if state_key == StateValues.WILDCARD or state_key == StateValues.LAZY:
+                # Ignore non-user IDs.
+                continue
+
+            if state_key == StateValues.ME:
+                # Normalize to proper user ID
+                state_key = user_id
+
+            # We remember the user if they haven't been invalidated
+            if (EventTypes.Member, state_key) not in state_deltas:
+                users_to_add_to_lazy_cache.add(state_key)
+
+    new_required_state_map = None
     if changes:
         # Update the required state config based on the changes.
         new_required_state_map = dict(prev_required_state_map)
@@ -1694,6 +1953,9 @@ def _required_state_changes(
                 # Remove entries with empty state keys.
                 new_required_state_map.pop(event_type, None)
 
-        return new_required_state_map, added_state_filter
-    else:
-        return None, added_state_filter
+    return _RequiredStateChangesReturn(
+        changed_required_state_map=new_required_state_map,
+        added_state_filter=added_state_filter,
+        lazy_members_invalidated=lazy_members_invalidated,
+        extra_users_to_add_to_lazy_cache=users_to_add_to_lazy_cache,
+    )

synapse/handlers/sliding_sync/store.py

@@ -13,7 +13,6 @@
 #
 
 import logging
-from typing import TYPE_CHECKING
 
 import attr
 
@@ -25,9 +24,7 @@ from synapse.types.handlers.sliding_sync import (
     PerConnectionState,
     SlidingSyncConfig,
 )
-
-if TYPE_CHECKING:
-    pass
+from synapse.util.clock import Clock
 
 logger = logging.getLogger(__name__)
 
@@ -61,7 +58,8 @@ class SlidingSyncConnectionStore:
             to mapping of room ID to `HaveSentRoom`.
     """
 
-    store: "DataStore"
+    clock: Clock
+    store: DataStore
 
     async def get_and_clear_connection_positions(
         self,
@@ -101,7 +99,7 @@ class SlidingSyncConnectionStore:
         If there are no changes to the state this may return the same token as
         the existing per-connection state.
         """
-        if not new_connection_state.has_updates():
+        if not new_connection_state.has_updates(self.clock):
             if from_token is not None:
                 return from_token.connection_position
             else:

synapse/handlers/user_directory.py

@@ -21,7 +21,7 @@
 
 import logging
 from http import HTTPStatus
-from typing import TYPE_CHECKING
+from typing import TYPE_CHECKING, Optional
 
 from twisted.internet.interfaces import IDelayedCall
 
@@ -125,7 +125,7 @@ class UserDirectoryHandler(StateDeltasHandler):
         # Guard to ensure we only have one process for refreshing remote profiles
         self._is_refreshing_remote_profiles = False
         # Handle to cancel the `call_later` of `kick_off_remote_profile_refresh_process`
-        self._refresh_remote_profiles_call_later: IDelayedCall | None = None
+        self._refresh_remote_profiles_call_later: Optional[IDelayedCall] = None
 
         # Guard to ensure we only have one process for refreshing remote profiles
         # for the given servers.

synapse/http/client.py

@@ -28,6 +28,7 @@ from typing import (
     BinaryIO,
     Callable,
     Mapping,
+    Optional,
     Protocol,
 )
 
@@ -313,7 +314,7 @@ class BlocklistingAgentWrapper(Agent):
         method: bytes,
         uri: bytes,
         headers: Headers | None = None,
-        bodyProducer: IBodyProducer | None = None,
+        bodyProducer: Optional[IBodyProducer] = None,
     ) -> defer.Deferred:
         h = urllib.parse.urlparse(uri.decode("ascii"))
 
@@ -1033,7 +1034,7 @@ class BodyExceededMaxSize(Exception):
 class _DiscardBodyWithMaxSizeProtocol(protocol.Protocol):
     """A protocol which immediately errors upon receiving data."""
 
-    transport: ITCPTransport | None = None
+    transport: Optional[ITCPTransport] = None
 
     def __init__(self, deferred: defer.Deferred):
         self.deferred = deferred
@@ -1075,7 +1076,7 @@ class _MultipartParserProtocol(protocol.Protocol):
     Protocol to read and parse a MSC3916 multipart/mixed response
     """
 
-    transport: ITCPTransport | None = None
+    transport: Optional[ITCPTransport] = None
 
     def __init__(
         self,
@@ -1188,7 +1189,7 @@ class _MultipartParserProtocol(protocol.Protocol):
 class _ReadBodyWithMaxSizeProtocol(protocol.Protocol):
     """A protocol which reads body to a stream, erroring if the body exceeds a maximum size."""
 
-    transport: ITCPTransport | None = None
+    transport: Optional[ITCPTransport] = None
 
     def __init__(
         self, stream: ByteWriteable, deferred: defer.Deferred, max_size: int | None

synapse/http/federation/matrix_federation_agent.py

@@ -19,7 +19,7 @@
 #
 import logging
 import urllib.parse
-from typing import Any, Generator
+from typing import Any, Generator, Optional
 from urllib.request import (  # type: ignore[attr-defined]
     proxy_bypass_environment,
 )
@@ -173,7 +173,7 @@ class MatrixFederationAgent:
         method: bytes,
         uri: bytes,
         headers: Headers | None = None,
-        bodyProducer: IBodyProducer | None = None,
+        bodyProducer: Optional[IBodyProducer] = None,
     ) -> Generator[defer.Deferred, Any, IResponse]:
         """
         Args:

synapse/http/matrixfederationclient.py

@@ -33,6 +33,7 @@ from typing import (
     Callable,
     Generic,
     Literal,
+    Optional,
     TextIO,
     TypeVar,
     cast,
@@ -691,7 +692,7 @@ class MatrixFederationHttpClient:
                             destination_bytes, method_bytes, url_to_sign_bytes, json
                         )
                         data = encode_canonical_json(json)
-                        producer: IBodyProducer | None = QuieterFileBodyProducer(
+                        producer: Optional[IBodyProducer] = QuieterFileBodyProducer(
                             BytesIO(data), cooperator=self._cooperator
                         )
                     else:

synapse/http/proxy.py

@@ -22,7 +22,7 @@
 import json
 import logging
 import urllib.parse
-from typing import TYPE_CHECKING, Any, cast
+from typing import TYPE_CHECKING, Any, Optional, cast
 
 from twisted.internet import protocol
 from twisted.internet.interfaces import ITCPTransport
@@ -237,7 +237,7 @@ class _ProxyResponseBody(protocol.Protocol):
     request.
     """
 
-    transport: ITCPTransport | None = None
+    transport: Optional[ITCPTransport] = None
 
     def __init__(self, request: "SynapseRequest") -> None:
         self._request = request

synapse/http/proxyagent.py

@@ -21,7 +21,7 @@
 import logging
 import random
 import re
-from typing import Any, Collection, Sequence, cast
+from typing import Any, Collection, Optional, Sequence, cast
 from urllib.parse import urlparse
 from urllib.request import (  # type: ignore[attr-defined]
     proxy_bypass_environment,
@@ -119,8 +119,8 @@ class ProxyAgent(_AgentBase):
         self,
         *,
         reactor: IReactorCore,
-        proxy_reactor: IReactorCore | None = None,
-        contextFactory: IPolicyForHTTPS | None = None,
+        proxy_reactor: Optional[IReactorCore] = None,
+        contextFactory: Optional[IPolicyForHTTPS] = None,
         connectTimeout: float | None = None,
         bindAddress: bytes | None = None,
         pool: HTTPConnectionPool | None = None,
@@ -175,7 +175,7 @@ class ProxyAgent(_AgentBase):
         self._policy_for_https = contextFactory
         self._reactor = cast(IReactorTime, reactor)
 
-        self._federation_proxy_endpoint: IStreamClientEndpoint | None = None
+        self._federation_proxy_endpoint: Optional[IStreamClientEndpoint] = None
         self._federation_proxy_credentials: ProxyCredentials | None = None
         if federation_proxy_locations:
             assert federation_proxy_credentials is not None, (
@@ -221,7 +221,7 @@ class ProxyAgent(_AgentBase):
         method: bytes,
         uri: bytes,
         headers: Headers | None = None,
-        bodyProducer: IBodyProducer | None = None,
+        bodyProducer: Optional[IBodyProducer] = None,
     ) -> "defer.Deferred[IResponse]":
         """
         Issue a request to the server indicated by the given uri.
@@ -365,11 +365,11 @@ class ProxyAgent(_AgentBase):
 def http_proxy_endpoint(
     proxy: bytes | None,
     reactor: IReactorCore,
-    tls_options_factory: IPolicyForHTTPS | None,
+    tls_options_factory: Optional[IPolicyForHTTPS],
     timeout: float = 30,
     bindAddress: bytes | str | tuple[bytes | str, int] | None = None,
     attemptDelay: float | None = None,
-) -> tuple[IStreamClientEndpoint | None, ProxyCredentials | None]:
+) -> tuple[Optional[IStreamClientEndpoint], ProxyCredentials | None]:
     """Parses an http proxy setting and returns an endpoint for the proxy
 
     Args:

synapse/http/replicationagent.py

@@ -20,6 +20,7 @@
 #
 
 import logging
+from typing import Optional
 
 from zope.interface import implementer
 
@@ -149,7 +150,7 @@ class ReplicationAgent(_AgentBase):
         method: bytes,
         uri: bytes,
         headers: Headers | None = None,
-        bodyProducer: IBodyProducer | None = None,
+        bodyProducer: Optional[IBodyProducer] = None,
     ) -> "defer.Deferred[IResponse]":
         """
         Issue a request to the server indicated by the given uri.

synapse/http/site.py

@@ -19,6 +19,7 @@
 #
 #
 import contextlib
+import json
 import logging
 import time
 from http import HTTPStatus
@@ -36,6 +37,7 @@ from twisted.web.http import HTTPChannel
 from twisted.web.resource import IResource, Resource
 from twisted.web.server import Request
 
+from synapse.api.errors import Codes, SynapseError
 from synapse.config.server import ListenerConfig
 from synapse.http import get_request_user_agent, redact_uri
 from synapse.http.proxy import ProxySite
@@ -59,6 +61,10 @@ logger = logging.getLogger(__name__)
 _next_request_seq = 0
 
 
+class ContentLengthError(SynapseError):
+    """Raised when content-length validation fails."""
+
+
 class SynapseRequest(Request):
     """Class which encapsulates an HTTP request to synapse.
 
@@ -144,36 +150,150 @@ class SynapseRequest(Request):
             self.synapse_site.site_tag,
         )
 
+    def _respond_with_error(self, synapse_error: SynapseError) -> None:
+        """Send an error response and close the connection."""
+        self.setResponseCode(synapse_error.code)
+        error_response_bytes = json.dumps(synapse_error.error_dict(None)).encode()
+
+        self.responseHeaders.setRawHeaders(b"Content-Type", [b"application/json"])
+        self.responseHeaders.setRawHeaders(
+            b"Content-Length", [f"{len(error_response_bytes)}"]
+        )
+        self.write(error_response_bytes)
+        self.loseConnection()
+
+    def _get_content_length_from_headers(self) -> int | None:
+        """Attempts to obtain the `Content-Length` value from the request's headers.
+
+        Returns:
+            Content length as `int` if present. Otherwise `None`.
+
+        Raises:
+            ContentLengthError: if multiple `Content-Length` headers are present or the
+                value is not an `int`.
+        """
+        content_length_headers = self.requestHeaders.getRawHeaders(b"Content-Length")
+        if content_length_headers is None:
+            return None
+
+        # If there are multiple `Content-Length` headers return an error.
+        # We don't want to even try to pick the right one if there are multiple
+        # as we could run into problems similar to request smuggling vulnerabilities
+        # which rely on the mismatch of how different systems interpret information.
+        if len(content_length_headers) != 1:
+            raise ContentLengthError(
+                HTTPStatus.BAD_REQUEST,
+                "Multiple Content-Length headers received",
+                Codes.UNKNOWN,
+            )
+
+        try:
+            return int(content_length_headers[0])
+        except (ValueError, TypeError):
+            raise ContentLengthError(
+                HTTPStatus.BAD_REQUEST,
+                "Content-Length header value is not a valid integer",
+                Codes.UNKNOWN,
+            )
+
+    def _validate_content_length(self) -> None:
+        """Validate Content-Length header and actual content size.
+
+        Raises:
+            ContentLengthError: If validation fails.
+        """
+        # we should have a `content` by now.
+        assert self.content, "_validate_content_length() called before gotLength()"
+        content_length = self._get_content_length_from_headers()
+
+        if content_length is None:
+            return
+
+        actual_content_length = self.content.tell()
+
+        if content_length > self._max_request_body_size:
+            logger.info(
+                "Rejecting request from %s because Content-Length %d exceeds maximum size %d: %s %s",
+                self.client,
+                content_length,
+                self._max_request_body_size,
+                self.get_method(),
+                self.get_redacted_uri(),
+            )
+            raise ContentLengthError(
+                HTTPStatus.REQUEST_ENTITY_TOO_LARGE,
+                f"Request content is too large (>{self._max_request_body_size})",
+                Codes.TOO_LARGE,
+            )
+
+        if content_length != actual_content_length:
+            comparison = (
+                "smaller" if content_length < actual_content_length else "larger"
+            )
+            logger.info(
+                "Rejecting request from %s because Content-Length %d is %s than the request content size %d: %s %s",
+                self.client,
+                content_length,
+                comparison,
+                actual_content_length,
+                self.get_method(),
+                self.get_redacted_uri(),
+            )
+            raise ContentLengthError(
+                HTTPStatus.BAD_REQUEST,
+                f"Rejecting request as the Content-Length header value {content_length} "
+                f"is {comparison} than the actual request content size {actual_content_length}",
+                Codes.UNKNOWN,
+            )
+
     # Twisted machinery: this method is called by the Channel once the full request has
     # been received, to dispatch the request to a resource.
-    #
-    # We're patching Twisted to bail/abort early when we see someone trying to upload
-    # `multipart/form-data` so we can avoid Twisted parsing the entire request body into
-    # in-memory (specific problem of this specific `Content-Type`). This protects us
-    # from an attacker uploading something bigger than the available RAM and crashing
-    # the server with a `MemoryError`, or carefully block just enough resources to cause
-    # all other requests to fail.
-    #
-    # FIXME: This can be removed once we Twisted releases a fix and we update to a
-    # version that is patched
     def requestReceived(self, command: bytes, path: bytes, version: bytes) -> None:
+        # In the case of a Content-Length header being present, and it's value being too
+        # large, throw a proper error to make debugging issues due to overly large requests much
+        # easier. Currently we handle such cases in `handleContentChunk` and abort the
+        # connection without providing a proper HTTP response.
+        #
+        # Attempting to write an HTTP response from within `handleContentChunk` does not
+        # work, so the code here has been added to at least provide a response in the
+        # case of the Content-Length header being present.
+        self.method, self.uri = command, path
+        self.clientproto = version
+
+        try:
+            self._validate_content_length()
+        except ContentLengthError as e:
+            self._respond_with_error(e)
+            return
+
+        # We're patching Twisted to bail/abort early when we see someone trying to upload
+        # `multipart/form-data` so we can avoid Twisted parsing the entire request body into
+        # in-memory (specific problem of this specific `Content-Type`). This protects us
+        # from an attacker uploading something bigger than the available RAM and crashing
+        # the server with a `MemoryError`, or carefully block just enough resources to cause
+        # all other requests to fail.
+        #
+        # FIXME: This can be removed once Twisted releases a fix and we update to a
+        # version that is patched
+        # See: https://github.com/element-hq/synapse/security/advisories/GHSA-rfq8-j7rh-8hf2
         if command == b"POST":
             ctype = self.requestHeaders.getRawHeaders(b"content-type")
             if ctype and b"multipart/form-data" in ctype[0]:
-                self.method, self.uri = command, path
-                self.clientproto = version
+                logger.warning(
+                    "Aborting connection from %s because `content-type: multipart/form-data` is unsupported: %s %s",
+                    self.client,
+                    self.get_method(),
+                    self.get_redacted_uri(),
+                )
+
                 self.code = HTTPStatus.UNSUPPORTED_MEDIA_TYPE.value
                 self.code_message = bytes(
                     HTTPStatus.UNSUPPORTED_MEDIA_TYPE.phrase, "ascii"
                 )
-                self.responseHeaders.setRawHeaders(b"content-length", [b"0"])
 
-                logger.warning(
-                    "Aborting connection from %s because `content-type: multipart/form-data` is unsupported: %s %s",
-                    self.client,
-                    command,
-                    path,
-                )
+                # FIXME: Return a better error response here similar to the
+                # `error_response_json` returned in other code paths here.
+                self.responseHeaders.setRawHeaders(b"Content-Length", [b"0"])
                 self.write(b"")
                 self.loseConnection()
                 return
@@ -815,6 +935,13 @@ class SynapseSite(ProxySite):
                 protocol.transport.loseConnection()
         self.connections.clear()
 
+        # Replace the resource tree with an empty resource to break circular references
+        # to the resource tree which holds a bunch of homeserver references. This is
+        # important if we try to call `hs.shutdown()` after `start` fails. For some
+        # reason, this doesn't seem to be necessary in the normal case where `start`
+        # succeeds and we call `hs.shutdown()` later.
+        self.resource = Resource()
+
     def log(self, request: SynapseRequest) -> None:  # type: ignore[override]
         pass
 

synapse/logging/_remote.py

@@ -25,7 +25,7 @@ import traceback
 from collections import deque
 from ipaddress import IPv4Address, IPv6Address, ip_address
 from math import floor
-from typing import Callable
+from typing import Callable, Optional
 
 import attr
 from zope.interface import implementer
@@ -113,7 +113,7 @@ class RemoteHandler(logging.Handler):
         port: int,
         maximum_buffer: int = 1000,
         level: int = logging.NOTSET,
-        _reactor: IReactorTime | None = None,
+        _reactor: Optional[IReactorTime] = None,
     ):
         super().__init__(level=level)
         self.host = host

synapse/logging/handlers.py

@@ -3,7 +3,7 @@ import time
 from logging import Handler, LogRecord
 from logging.handlers import MemoryHandler
 from threading import Thread
-from typing import cast
+from typing import Optional, cast
 
 from twisted.internet.interfaces import IReactorCore
 
@@ -26,7 +26,7 @@ class PeriodicallyFlushingMemoryHandler(MemoryHandler):
         target: Handler | None = None,
         flushOnClose: bool = True,
         period: float = 5.0,
-        reactor: IReactorCore | None = None,
+        reactor: Optional[IReactorCore] = None,
     ) -> None:
         """
         period: the period between automatic flushes

synapse/media/_base.py

@@ -30,6 +30,7 @@ from typing import (
     Awaitable,
     BinaryIO,
     Generator,
+    Optional,
 )
 
 import attr
@@ -705,7 +706,7 @@ class ThreadedFileSender:
 
         self.file: BinaryIO | None = None
         self.deferred: "Deferred[None]" = Deferred()
-        self.consumer: interfaces.IConsumer | None = None
+        self.consumer: Optional[IConsumer] = None
 
         # Signals if the thread should keep reading/sending data. Set means
         # continue, clear means pause.

synapse/media/media_repository.py

@@ -914,6 +914,7 @@ class MediaRepository:
             filesystem_id=file_id,
             last_access_ts=time_now_ms,
             quarantined_by=None,
+            quarantined_ts=None,
             authenticated=authenticated,
             sha256=sha256writer.hexdigest(),
         )
@@ -1047,6 +1048,7 @@ class MediaRepository:
             filesystem_id=file_id,
             last_access_ts=time_now_ms,
             quarantined_by=None,
+            quarantined_ts=None,
             authenticated=authenticated,
             sha256=sha256writer.hexdigest(),
         )

synapse/push/emailpusher.py

@@ -20,7 +20,7 @@
 #
 
 import logging
-from typing import TYPE_CHECKING
+from typing import TYPE_CHECKING, Optional
 
 from twisted.internet.error import AlreadyCalled, AlreadyCancelled
 from twisted.internet.interfaces import IDelayedCall
@@ -71,7 +71,7 @@ class EmailPusher(Pusher):
         self.server_name = hs.hostname
         self.store = self.hs.get_datastores().main
         self.email = pusher_config.pushkey
-        self.timed_call: IDelayedCall | None = None
+        self.timed_call: Optional[IDelayedCall] = None
         self.throttle_params: dict[str, ThrottleParams] = {}
         self._inited = False
 

synapse/push/httppusher.py

@@ -21,7 +21,7 @@
 import logging
 import random
 import urllib.parse
-from typing import TYPE_CHECKING
+from typing import TYPE_CHECKING, Optional
 
 from prometheus_client import Counter
 
@@ -120,7 +120,7 @@ class HttpPusher(Pusher):
         self.data = pusher_config.data
         self.backoff_delay = HttpPusher.INITIAL_BACKOFF_SEC
         self.failing_since = pusher_config.failing_since
-        self.timed_call: IDelayedCall | None = None
+        self.timed_call: Optional[IDelayedCall] = None
         self._is_processing = False
         self._group_unread_count_by_room = (
             hs.config.push.push_group_unread_count_by_room

synapse/rest/admin/__init__.py

@@ -114,7 +114,8 @@ from synapse.rest.admin.users import (
     UserByThreePid,
     UserInvitesCount,
     UserJoinedRoomCount,
-    UserMembershipRestServlet,
+    UserJoinedRoomsRestServlet,
+    UserMembershipsRestServlet,
     UserRegisterServlet,
     UserReplaceMasterCrossSigningKeyRestServlet,
     UserRestServletV2,
@@ -297,7 +298,8 @@ def register_servlets(hs: "HomeServer", http_server: HttpServer) -> None:
     VersionServlet(hs).register(http_server)
     if not auth_delegated:
         UserAdminServlet(hs).register(http_server)
-    UserMembershipRestServlet(hs).register(http_server)
+    UserJoinedRoomsRestServlet(hs).register(http_server)
+    UserMembershipsRestServlet(hs).register(http_server)
     if not auth_delegated:
         UserTokenRestServlet(hs).register(http_server)
     UserRestServletV2(hs).register(http_server)

synapse/rest/admin/media.py

@@ -293,6 +293,38 @@ class ListMediaInRoom(RestServlet):
         return HTTPStatus.OK, {"local": local_mxcs, "remote": remote_mxcs}
 
 
+class ListQuarantinedMedia(RestServlet):
+    """Lists all quarantined media on the server."""
+
+    PATTERNS = admin_patterns("/media/quarantined$")
+
+    def __init__(self, hs: "HomeServer"):
+        self.store = hs.get_datastores().main
+        self.auth = hs.get_auth()
+
+    async def on_GET(
+        self,
+        request: SynapseRequest,
+    ) -> tuple[int, JsonDict]:
+        await assert_requester_is_admin(self.auth, request)
+
+        start = parse_integer(request, "from", default=0)
+        limit = parse_integer(request, "limit", default=100)
+        local_or_remote = parse_string(request, "kind", required=True)
+
+        if local_or_remote not in ["local", "remote"]:
+            raise SynapseError(
+                HTTPStatus.BAD_REQUEST,
+                "Query parameter `kind` must be either 'local' or 'remote'.",
+            )
+
+        mxcs = await self.store.get_quarantined_media_mxcs(
+            start, limit, local_or_remote == "local"
+        )
+
+        return HTTPStatus.OK, {"media": mxcs}
+
+
 class PurgeMediaCacheRestServlet(RestServlet):
     PATTERNS = admin_patterns("/purge_media_cache$")
 
@@ -532,6 +564,7 @@ def register_servlets_for_media_repo(hs: "HomeServer", http_server: HttpServer)
     ProtectMediaByID(hs).register(http_server)
     UnprotectMediaByID(hs).register(http_server)
     ListMediaInRoom(hs).register(http_server)
+    ListQuarantinedMedia(hs).register(http_server)
     # XXX DeleteMediaByDateSize must be registered before DeleteMediaByID as
     #     their URL routes overlap.
     DeleteMediaByDateSize(hs).register(http_server)

synapse/rest/admin/users.py

@@ -1031,7 +1031,7 @@ class UserAdminServlet(RestServlet):
         return HTTPStatus.OK, {}
 
 
-class UserMembershipRestServlet(RestServlet):
+class UserJoinedRoomsRestServlet(RestServlet):
     """
     Get list of joined room ID's for a user.
     """
@@ -1054,6 +1054,28 @@ class UserMembershipRestServlet(RestServlet):
         return HTTPStatus.OK, rooms_response
 
 
+class UserMembershipsRestServlet(RestServlet):
+    """
+    Get list of room memberships for a user.
+    """
+
+    PATTERNS = admin_patterns("/users/(?P<user_id>[^/]*)/memberships$")
+
+    def __init__(self, hs: "HomeServer"):
+        self.is_mine = hs.is_mine
+        self.auth = hs.get_auth()
+        self.store = hs.get_datastores().main
+
+    async def on_GET(
+        self, request: SynapseRequest, user_id: str
+    ) -> tuple[int, JsonDict]:
+        await assert_requester_is_admin(self.auth, request)
+
+        memberships = await self.store.get_memberships_for_user(user_id)
+
+        return HTTPStatus.OK, {"memberships": memberships}
+
+
 class PushersRestServlet(RestServlet):
     """
     Gets information about all pushers for a specific `user_id`.

synapse/server.py

@@ -34,6 +34,7 @@ from typing import (
     Any,
     Awaitable,
     Callable,
+    Optional,
     TypeVar,
     cast,
 )
@@ -54,6 +55,7 @@ from synapse.api.auth import Auth
 from synapse.api.auth.internal import InternalAuth
 from synapse.api.auth.mas import MasDelegatedAuth
 from synapse.api.auth_blocking import AuthBlocking
+from synapse.api.errors import HomeServerNotSetupException
 from synapse.api.filtering import Filtering
 from synapse.api.ratelimiting import Ratelimiter, RequestRatelimiter
 from synapse.app._base import unregister_sighups
@@ -319,7 +321,7 @@ class HomeServer(metaclass=abc.ABCMeta):
         self,
         hostname: str,
         config: HomeServerConfig,
-        reactor: ISynapseReactor | None = None,
+        reactor: Optional[ISynapseReactor] = None,
     ):
         """
         Args:
@@ -352,7 +354,7 @@ class HomeServer(metaclass=abc.ABCMeta):
         self._module_web_resources_consumed = False
 
         # This attribute is set by the free function `refresh_certificate`.
-        self.tls_server_context_factory: IOpenSSLContextFactory | None = None
+        self.tls_server_context_factory: Optional[IOpenSSLContextFactory] = None
 
         self._is_shutdown = False
         self._async_shutdown_handlers: list[ShutdownInfo] = []
@@ -399,7 +401,7 @@ class HomeServer(metaclass=abc.ABCMeta):
         """
         if self._is_shutdown:
             raise Exception(
-                f"Cannot start background process. HomeServer has been shutdown {len(self._background_processes)} {len(self.get_clock()._looping_calls)} {len(self.get_clock()._call_id_to_delayed_call)}"
+                "Cannot start background process. HomeServer has been shutdown"
             )
 
         # Ignore linter error as this is the one location this should be called.
@@ -466,7 +468,17 @@ class HomeServer(metaclass=abc.ABCMeta):
 
         # TODO: Cleanup replication pieces
 
-        self.get_keyring().shutdown()
+        keyring: Keyring | None = None
+        try:
+            keyring = self.get_keyring()
+        except HomeServerNotSetupException:
+            # If the homeserver wasn't fully setup, keyring won't have existed before
+            # this and will fail to be initialized but it cleans itself up for any
+            # partial initialization problem.
+            pass
+
+        if keyring:
+            keyring.shutdown()
 
         # Cleanup metrics associated with the homeserver
         for later_gauge in all_later_gauges_to_clean_up_on_shutdown.values():
@@ -478,8 +490,12 @@ class HomeServer(metaclass=abc.ABCMeta):
             self.config.server.server_name
         )
 
-        for db in self.get_datastores().databases:
-            db.stop_background_updates()
+        try:
+            for db in self.get_datastores().databases:
+                db.stop_background_updates()
+        except HomeServerNotSetupException:
+            # If the homeserver wasn't fully setup, the datastores won't exist
+            pass
 
         if self.should_send_federation():
             try:
@@ -513,8 +529,12 @@ class HomeServer(metaclass=abc.ABCMeta):
                 pass
         self._background_processes.clear()
 
-        for db in self.get_datastores().databases:
-            db._db_pool.close()
+        try:
+            for db in self.get_datastores().databases:
+                db._db_pool.close()
+        except HomeServerNotSetupException:
+            # If the homeserver wasn't fully setup, the datastores won't exist
+            pass
 
     def register_async_shutdown_handler(
         self,
@@ -677,7 +697,9 @@ class HomeServer(metaclass=abc.ABCMeta):
 
     def get_datastores(self) -> Databases:
         if not self.datastores:
-            raise Exception("HomeServer.setup must be called before getting datastores")
+            raise HomeServerNotSetupException(
+                "HomeServer.setup must be called before getting datastores"
+            )
 
         return self.datastores
 

synapse/storage/databases/main/media_repository.py

@@ -61,6 +61,7 @@ class LocalMedia:
     url_cache: str | None
     last_access_ts: int
     quarantined_by: str | None
+    quarantined_ts: int | None
     safe_from_quarantine: bool
     user_id: str | None
     authenticated: bool | None
@@ -78,6 +79,7 @@ class RemoteMedia:
     created_ts: int
     last_access_ts: int
     quarantined_by: str | None
+    quarantined_ts: int | None
     authenticated: bool | None
     sha256: str | None
 
@@ -243,6 +245,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
                 "user_id",
                 "authenticated",
                 "sha256",
+                "quarantined_ts",
             ),
             allow_none=True,
             desc="get_local_media",
@@ -262,6 +265,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
             user_id=row[8],
             authenticated=row[9],
             sha256=row[10],
+            quarantined_ts=row[11],
         )
 
     async def get_local_media_by_user_paginate(
@@ -319,7 +323,8 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
                     safe_from_quarantine,
                     user_id,
                     authenticated,
-                    sha256
+                    sha256,
+                    quarantined_ts
                 FROM local_media_repository
                 WHERE user_id = ?
                 ORDER BY {order_by_column} {order}, media_id ASC
@@ -345,6 +350,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
                     user_id=row[9],
                     authenticated=row[10],
                     sha256=row[11],
+                    quarantined_ts=row[12],
                 )
                 for row in txn
             ]
@@ -695,6 +701,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
                 "quarantined_by",
                 "authenticated",
                 "sha256",
+                "quarantined_ts",
             ),
             allow_none=True,
             desc="get_cached_remote_media",
@@ -713,6 +720,7 @@ class MediaRepositoryStore(MediaRepositoryBackgroundUpdateStore):
             quarantined_by=row[6],
             authenticated=row[7],
             sha256=row[8],
+            quarantined_ts=row[9],
         )
 
     async def store_cached_remote_media(

synapse/storage/databases/main/room.py

@@ -945,6 +945,50 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
             max_lifetime=max_lifetime,
         )
 
+    async def get_quarantined_media_mxcs(
+        self, index_start: int, index_limit: int, local: bool
+    ) -> list[str]:
+        """Retrieves all the quarantined media MXC URIs starting from the given position,
+        ordered from oldest quarantined timestamp, then alphabetically by media ID
+        (including origin).
+
+        Note that on established servers the "quarantined timestamp" may be zero due to
+        being introduced after the quarantine timestamp field was introduced.
+
+        Args:
+            index_start: The position to start from.
+            index_limit: The maximum number of results to return.
+            local: When true, only local media will be returned. When false, only remote media will be returned.
+
+        Returns:
+            The quarantined media as a list of media IDs.
+        """
+
+        def _get_quarantined_media_mxcs_txn(
+            txn: LoggingTransaction,
+        ) -> list[str]:
+            # We order by quarantined timestamp *and* media ID (including origin, when
+            # known) to ensure the ordering is stable for established servers.
+            if local:
+                sql = "SELECT '' as media_origin, media_id FROM local_media_repository WHERE quarantined_by IS NOT NULL ORDER BY quarantined_ts, media_id ASC LIMIT ? OFFSET ?"
+            else:
+                sql = "SELECT media_origin, media_id FROM remote_media_cache WHERE quarantined_by IS NOT NULL ORDER BY quarantined_ts, media_origin, media_id ASC LIMIT ? OFFSET ?"
+            txn.execute(sql, (index_limit, index_start))
+
+            mxcs = []
+
+            for media_origin, media_id in txn:
+                if local:
+                    media_origin = self.hs.hostname
+                mxcs.append(f"mxc://{media_origin}/{media_id}")
+
+            return mxcs
+
+        return await self.db_pool.runInteraction(
+            "get_quarantined_media_mxcs",
+            _get_quarantined_media_mxcs_txn,
+        )
+
     async def get_media_mxcs_in_room(self, room_id: str) -> tuple[list[str], list[str]]:
         """Retrieves all the local and remote media MXC URIs in a given room
 
@@ -952,7 +996,7 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
             room_id
 
         Returns:
-            The local and remote media as a lists of the media IDs.
+            The local and remote media as lists of the media IDs.
         """
 
         def _get_media_mxcs_in_room_txn(
@@ -1147,6 +1191,10 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
             The total number of media items quarantined
         """
         total_media_quarantined = 0
+        now_ts: int | None = self.clock.time_msec()
+
+        if quarantined_by is None:
+            now_ts = None
 
         # Effectively a legacy path, update any media that was explicitly named.
         if media_ids:
@@ -1155,13 +1203,13 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
             )
             sql = f"""
                 UPDATE local_media_repository
-                SET quarantined_by = ?
+                SET quarantined_by = ?, quarantined_ts = ?
                 WHERE {sql_many_clause_sql}"""
 
             if quarantined_by is not None:
                 sql += " AND safe_from_quarantine = FALSE"
 
-            txn.execute(sql, [quarantined_by] + sql_many_clause_args)
+            txn.execute(sql, [quarantined_by, now_ts] + sql_many_clause_args)
             # Note that a rowcount of -1 can be used to indicate no rows were affected.
             total_media_quarantined += txn.rowcount if txn.rowcount > 0 else 0
 
@@ -1172,13 +1220,13 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
             )
             sql = f"""
                 UPDATE local_media_repository
-                SET quarantined_by = ?
+                SET quarantined_by = ?, quarantined_ts = ?
                 WHERE {sql_many_clause_sql}"""
 
             if quarantined_by is not None:
                 sql += " AND safe_from_quarantine = FALSE"
 
-            txn.execute(sql, [quarantined_by] + sql_many_clause_args)
+            txn.execute(sql, [quarantined_by, now_ts] + sql_many_clause_args)
             total_media_quarantined += txn.rowcount if txn.rowcount > 0 else 0
 
         return total_media_quarantined
@@ -1202,6 +1250,10 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
             The total number of media items quarantined
         """
         total_media_quarantined = 0
+        now_ts: int | None = self.clock.time_msec()
+
+        if quarantined_by is None:
+            now_ts = None
 
         if media:
             sql_in_list_clause, sql_args = make_tuple_in_list_sql_clause(
@@ -1211,10 +1263,10 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
             )
             sql = f"""
                 UPDATE remote_media_cache
-                SET quarantined_by = ?
+                SET quarantined_by = ?, quarantined_ts = ?
                 WHERE {sql_in_list_clause}"""
 
-            txn.execute(sql, [quarantined_by] + sql_args)
+            txn.execute(sql, [quarantined_by, now_ts] + sql_args)
             total_media_quarantined += txn.rowcount if txn.rowcount > 0 else 0
 
         total_media_quarantined = 0
@@ -1224,9 +1276,9 @@ class RoomWorkerStore(CacheInvalidationWorkerStore):
             )
             sql = f"""
                 UPDATE remote_media_cache
-                SET quarantined_by = ?
+                SET quarantined_by = ?, quarantined_ts = ?
                 WHERE {sql_many_clause_sql}"""
-            txn.execute(sql, [quarantined_by] + sql_many_clause_args)
+            txn.execute(sql, [quarantined_by, now_ts] + sql_many_clause_args)
             total_media_quarantined += txn.rowcount if txn.rowcount > 0 else 0
 
         return total_media_quarantined

synapse/storage/databases/main/roommember.py

@@ -747,6 +747,27 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
 
         return frozenset(room_ids)
 
+    async def get_memberships_for_user(self, user_id: str) -> dict[str, str]:
+        """Returns a dict of room_id to membership state for a given user.
+
+        If a remote user only returns rooms this server is currently
+        participating in.
+        """
+
+        rows = cast(
+            list[tuple[str, str]],
+            await self.db_pool.simple_select_list(
+                "current_state_events",
+                keyvalues={
+                    "type": EventTypes.Member,
+                    "state_key": user_id,
+                },
+                retcols=["room_id", "membership"],
+                desc="get_memberships_for_user",
+            ),
+        )
+        return dict(rows)
+
     @cached(max_entries=500000, iterable=True)
     async def get_rooms_for_user(self, user_id: str) -> frozenset[str]:
         """Returns a set of room_ids the user is currently joined to.

synapse/storage/databases/main/sliding_sync.py

@@ -14,7 +14,7 @@
 
 
 import logging
-from typing import TYPE_CHECKING, Mapping, cast
+from typing import TYPE_CHECKING, AbstractSet, Mapping, cast
 
 import attr
 
@@ -26,13 +26,16 @@ from synapse.storage.database import (
     DatabasePool,
     LoggingDatabaseConnection,
     LoggingTransaction,
+    make_in_list_sql_clause,
 )
+from synapse.storage.engines import PostgresEngine
 from synapse.types import MultiWriterStreamToken, RoomStreamToken
 from synapse.types.handlers.sliding_sync import (
     HaveSentRoom,
     HaveSentRoomFlag,
     MutablePerConnectionState,
     PerConnectionState,
+    RoomLazyMembershipChanges,
     RoomStatusMap,
     RoomSyncConfig,
 )
@@ -373,6 +376,13 @@ class SlidingSyncStore(SQLBaseStore):
             value_values=values,
         )
 
+        self._persist_sliding_sync_connection_lazy_members_txn(
+            txn,
+            connection_key,
+            connection_position,
+            per_connection_state.room_lazy_membership,
+        )
+
         return connection_position
 
     @cached(iterable=True, max_entries=100000)
@@ -446,6 +456,23 @@ class SlidingSyncStore(SQLBaseStore):
         """
         txn.execute(sql, (connection_key, connection_position))
 
+        # Move any lazy membership entries for this connection position to have
+        # `NULL` connection position, indicating that it applies to all future
+        # positions on this connection. This is safe because we have deleted all
+        # other (potentially forked) connection positions, and so all future
+        # positions in this connection will be a continuation of the current
+        # position. Thus any lazy membership entries we have sent down will still
+        # be valid.
+        self.db_pool.simple_update_txn(
+            txn,
+            table="sliding_sync_connection_lazy_members",
+            keyvalues={
+                "connection_key": connection_key,
+                "connection_position": connection_position,
+            },
+            updatevalues={"connection_position": None},
+        )
+
         # Fetch and create a mapping from required state ID to the actual
         # required state for the connection.
         rows = self.db_pool.simple_select_list_txn(
@@ -525,8 +552,153 @@ class SlidingSyncStore(SQLBaseStore):
             receipts=RoomStatusMap(receipts),
             account_data=RoomStatusMap(account_data),
             room_configs=room_configs,
+            room_lazy_membership={},
         )
 
+    async def get_sliding_sync_connection_lazy_members(
+        self,
+        connection_position: int,
+        room_id: str,
+        user_ids: AbstractSet[str],
+    ) -> Mapping[str, int]:
+        """Get which user IDs in the room we have previously sent lazy
+        membership for.
+
+        Args:
+            connection_position: The sliding sync connection position.
+            room_id: The room ID to get lazy members for.
+            user_ids: The user IDs to check whether we've previously sent
+                because of lazy membership.
+
+        Returns:
+            The mapping of user IDs to the last seen timestamp for those user
+            IDs. Only includes user IDs that we have previously sent lazy
+            membership for, and so may be a subset of the `user_ids` passed in.
+        """
+
+        def get_sliding_sync_connection_lazy_members_txn(
+            txn: LoggingTransaction,
+        ) -> Mapping[str, int]:
+            user_clause, user_args = make_in_list_sql_clause(
+                txn.database_engine, "user_id", user_ids
+            )
+
+            # Fetch all the lazy membership entries for the given connection,
+            # room and user IDs. We don't have the `connection_key` here, so we
+            # join against `sliding_sync_connection_positions` to get it.
+            #
+            # Beware that there are two `connection_position` columns in the
+            # query which are different, the one in
+            # `sliding_sync_connection_positions` is the one we match to get the
+            # connection_key, whereas the one in
+            # `sliding_sync_connection_lazy_members` is what we filter against
+            # (it may be null or the same as the one passed in).
+            #
+            # FIXME: We should pass in `connection_key` here to avoid the join.
+            # We don't do this currently as the caller doesn't have it handy.
+            sql = f"""
+                SELECT user_id, members.connection_position, last_seen_ts
+                FROM sliding_sync_connection_lazy_members AS members
+                INNER JOIN sliding_sync_connection_positions AS pos USING (connection_key)
+                WHERE pos.connection_position = ? AND room_id = ? AND {user_clause}
+            """
+
+            txn.execute(sql, (connection_position, room_id, *user_args))
+
+            # Filter out any cache entries that only apply to forked connection
+            # positions. Entries with `NULL` `connection_position` apply to all
+            # positions on the connection.
+            return {
+                user_id: last_seen_ts
+                for user_id, db_connection_position, last_seen_ts in txn
+                if db_connection_position == connection_position
+                or db_connection_position is None
+            }
+
+        return await self.db_pool.runInteraction(
+            "get_sliding_sync_connection_lazy_members",
+            get_sliding_sync_connection_lazy_members_txn,
+            db_autocommit=True,  # Avoid transaction for single read
+        )
+
+    def _persist_sliding_sync_connection_lazy_members_txn(
+        self,
+        txn: LoggingTransaction,
+        connection_key: int,
+        new_connection_position: int,
+        all_changes: dict[str, RoomLazyMembershipChanges],
+    ) -> None:
+        """Persist that we have sent lazy membership for the given user IDs."""
+
+        now = self.clock.time_msec()
+
+        # Figure out which cache entries to add or update.
+        #
+        # These are either a) new entries we've never sent before (i.e. with a
+        # None last_seen_ts), or b) where the `last_seen_ts` is old enough that
+        # we want to update it.
+        #
+        # We don't update the timestamp every time to avoid hammering the DB
+        # with writes, and we don't need the timestamp to be precise. It is used
+        # to evict old entries that haven't been used in a while.
+        to_update: list[tuple[str, str]] = []
+        for room_id, room_changes in all_changes.items():
+            user_ids_to_update = room_changes.get_returned_user_ids_to_update(
+                self.clock
+            )
+            to_update.extend((room_id, user_id) for user_id in user_ids_to_update)
+
+        if to_update:
+            # Upsert the new/updated entries.
+            #
+            # Ignore conflicts where the existing entry has a different
+            # connection position (i.e. from a forked connection position). This
+            # may mean that we lose some updates, but that's acceptable as this
+            # is a cache and its fine for it to *not* include rows. (Downstream
+            # this will cause us to maybe send a few extra lazy members down
+            # sync, but we're allowed to send extra members).
+            sql = """
+                INSERT INTO sliding_sync_connection_lazy_members
+                (connection_key, connection_position, room_id, user_id, last_seen_ts)
+                VALUES {value_placeholder}
+                ON CONFLICT (connection_key, room_id, user_id)
+                DO UPDATE SET last_seen_ts = EXCLUDED.last_seen_ts
+                WHERE sliding_sync_connection_lazy_members.connection_position IS NULL
+                    OR sliding_sync_connection_lazy_members.connection_position = EXCLUDED.connection_position
+            """
+
+            args = [
+                (connection_key, new_connection_position, room_id, user_id, now)
+                for room_id, user_id in to_update
+            ]
+
+            if isinstance(self.database_engine, PostgresEngine):
+                sql = sql.format(value_placeholder="?")
+                txn.execute_values(sql, args, fetch=False)
+            else:
+                sql = sql.format(value_placeholder="(?, ?, ?, ?, ?)")
+                txn.execute_batch(sql, args)
+
+        # Remove any invalidated entries.
+        to_remove: list[tuple[str, str]] = []
+        for room_id, room_changes in all_changes.items():
+            for user_id in room_changes.invalidated_user_ids:
+                to_remove.append((room_id, user_id))
+
+        if to_remove:
+            # We don't try and match on connection position here: it's fine to
+            # remove it from all forks. This is a cache so it's fine to expire
+            # arbitrary entries, the worst that happens is we send a few extra
+            # lazy members down sync.
+            self.db_pool.simple_delete_many_batch_txn(
+                txn,
+                table="sliding_sync_connection_lazy_members",
+                keys=("connection_key", "room_id", "user_id"),
+                values=[
+                    (connection_key, room_id, user_id) for room_id, user_id in to_remove
+                ],
+            )
+
     @wrap_as_background_process("delete_old_sliding_sync_connections")
     async def delete_old_sliding_sync_connections(self) -> None:
         """Delete sliding sync connections that have not been used for a long time."""
@@ -564,6 +736,10 @@ class PerConnectionStateDB:
 
     room_configs: Mapping[str, "RoomSyncConfig"]
 
+    room_lazy_membership: dict[str, RoomLazyMembershipChanges]
+    """Lazy membership changes to persist alongside this state. Only used
+    when persisting."""
+
     @staticmethod
     async def from_state(
         per_connection_state: "MutablePerConnectionState", store: "DataStore"
@@ -618,6 +794,7 @@ class PerConnectionStateDB:
             receipts=RoomStatusMap(receipts),
             account_data=RoomStatusMap(account_data),
             room_configs=per_connection_state.room_configs.maps[0],
+            room_lazy_membership=per_connection_state.room_lazy_membership,
         )
 
     async def to_state(self, store: "DataStore") -> "PerConnectionState":

synapse/storage/databases/main/state.py

@@ -983,7 +983,7 @@ class StateMapWrapper(dict[StateKey, str]):
             raise Exception("State map was filtered and doesn't include: %s", key)
         return super().__getitem__(key)
 
-    @overload  # type: ignore[override]
+    @overload
     def get(self, key: StateKey, default: None = None, /) -> str | None: ...
     @overload
     def get(self, key: StateKey, default: str, /) -> str: ...

synapse/storage/schema/main/delta/93/02_sliding_sync_members.sql

@@ -0,0 +1,60 @@
+--
+-- This file is licensed under the Affero General Public License (AGPL) version 3.
+--
+-- Copyright (C) 2025 Element Creations Ltd
+--
+-- This program is free software: you can redistribute it and/or modify
+-- it under the terms of the GNU Affero General Public License as
+-- published by the Free Software Foundation, either version 3 of the
+-- License, or (at your option) any later version.
+--
+-- See the GNU Affero General Public License for more details:
+-- <https://www.gnu.org/licenses/agpl-3.0.html>.
+
+
+-- Tracks which member states have been sent to the client for lazy-loaded
+-- members in sliding sync. This is a *cache* as it doesn't matter if we send
+-- down members we've previously sent down, i.e. it's safe to delete any rows.
+--
+-- We could have tracked these as part of the
+-- `sliding_sync_connection_required_state` table, but that would bloat that
+-- table significantly as most rooms will have lazy-loaded members. We want to
+-- keep that table small as we always pull out all rows for the connection for
+-- every request, so storing lots of data there would be bad for performance. To
+-- keep that table small we also deduplicate the requested state across
+-- different rooms, which if we stored lazy members there would prevent.
+--
+-- We track a *rough* `last_seen_ts` for each user in each room which indicates
+-- when we last would've sent their member state to the client. `last_seen_ts`
+-- is used so that we can remove members which haven't been seen for a while to
+-- save space. This is a *rough* timestamp as we don't want to update the
+-- timestamp every time to avoid hammering the DB with writes, and we don't need
+-- the timestamp to be precise (as it is used to evict old entries that haven't
+-- been used in a while).
+--
+-- Care must be taken when handling "forked" positions, i.e. we have responded
+-- to a request with a position and then get another different request using the
+-- previous position as a base. We track this by including a
+-- `connection_position` for newly inserted rows. When we advance the position
+-- we set this to NULL for all rows which were present at that position, and
+-- delete all other rows. When reading rows we can then filter out any rows
+-- which have a non-NULL `connection_position` which is not the current
+-- position.
+--
+-- I.e. `connection_position` is NULL for rows which are valid for *all*
+-- positions on the connection, and is non-NULL for rows which are only valid
+-- for a specific position.
+--
+-- When invalidating rows, we can just delete them. Technically this could
+-- invalidate for a forked position, but this is acceptable as equivalent to a
+-- cache eviction.
+CREATE TABLE sliding_sync_connection_lazy_members (
+    connection_key BIGINT NOT NULL REFERENCES sliding_sync_connections(connection_key) ON DELETE CASCADE,
+    connection_position BIGINT REFERENCES sliding_sync_connection_positions(connection_position) ON DELETE CASCADE,
+    room_id TEXT NOT NULL,
+    user_id TEXT NOT NULL,
+    last_seen_ts BIGINT NOT NULL
+);
+
+CREATE UNIQUE INDEX sliding_sync_connection_lazy_members_idx ON sliding_sync_connection_lazy_members (connection_key, room_id, user_id);
+CREATE INDEX sliding_sync_connection_lazy_members_pos_idx ON sliding_sync_connection_lazy_members (connection_key, connection_position) WHERE connection_position IS NOT NULL;

synapse/storage/schema/main/delta/93/04_add_quarantined_ts_to_media.sql

@@ -0,0 +1,27 @@
+--
+-- This file is licensed under the Affero General Public License (AGPL) version 3.
+--
+-- Copyright (C) 2025 Element Creations, Ltd
+--
+-- This program is free software: you can redistribute it and/or modify
+-- it under the terms of the GNU Affero General Public License as
+-- published by the Free Software Foundation, either version 3 of the
+-- License, or (at your option) any later version.
+--
+-- See the GNU Affero General Public License for more details:
+-- <https://www.gnu.org/licenses/agpl-3.0.html>.
+
+-- Add a timestamp for when the sliding sync connection position was last used,
+-- only updated with a small granularity.
+--
+-- This should be NOT NULL, but we need to consider existing rows. In future we
+-- may want to either backfill this or delete all rows with a NULL value (and
+-- then make it NOT NULL).
+ALTER TABLE local_media_repository ADD COLUMN quarantined_ts BIGINT;
+ALTER TABLE remote_media_cache ADD COLUMN quarantined_ts BIGINT;
+
+UPDATE local_media_repository SET quarantined_ts = 0 WHERE quarantined_by IS NOT NULL;
+UPDATE remote_media_cache SET quarantined_ts = 0 WHERE quarantined_by IS NOT NULL;
+
+-- Note: We *probably* should have an index on quarantined_ts, but we're going
+-- to try to defer that to a future migration after seeing the performance impact.

synapse/types/handlers/sliding_sync.py

@@ -49,12 +49,21 @@ from synapse.types import (
     UserID,
 )
 from synapse.types.rest.client import SlidingSyncBody
+from synapse.util.clock import Clock
+from synapse.util.duration import Duration
 
 if TYPE_CHECKING:
     from synapse.handlers.relations import BundledAggregations
 
 logger = logging.getLogger(__name__)
 
+# How often to update the last seen timestamp for lazy members.
+#
+# We don't update the timestamp every time to avoid hammering the DB with
+# writes, and we don't need the timestamp to be precise (as it is used to evict
+# old entries that haven't been used in a while).
+LAZY_MEMBERS_UPDATE_INTERVAL = Duration(hours=1)
+
 
 class SlidingSyncConfig(SlidingSyncBody):
     """
@@ -891,6 +900,69 @@ class PerConnectionState:
         return len(self.rooms) + len(self.receipts) + len(self.room_configs)
 
 
+@attr.s(auto_attribs=True)
+class RoomLazyMembershipChanges:
+    """Changes to lazily-loaded room memberships for a given room."""
+
+    returned_user_id_to_last_seen_ts_map: Mapping[str, int | None] = attr.Factory(dict)
+    """Map from user ID to timestamp for users whose membership we have lazily
+    loaded in this room an request. The timestamp indicates the time we
+    previously needed the membership, or None if we sent it down for the first
+    time in this request.
+
+    We track a *rough* `last_seen_ts` for each user in each room which indicates
+    when we last would've sent their member state to the client. This is used so
+    that we can remove members which haven't been seen for a while to save
+    space.
+
+    Note: this will include users whose membership we would have sent down but
+    didn't due to us having previously sent them.
+    """
+
+    invalidated_user_ids: AbstractSet[str] = attr.Factory(set)
+    """Set of user IDs whose latest membership we have *not* sent down"""
+
+    def get_returned_user_ids_to_update(self, clock: Clock) -> StrCollection:
+        """Get the user IDs whose last seen timestamp we need to update in the
+        database.
+
+        This is a subset of user IDs in `returned_user_id_to_last_seen_ts_map`,
+        whose timestamp is either None (first time we've sent them) or older
+        than `LAZY_MEMBERS_UPDATE_INTERVAL`.
+
+        We only update the timestamp in the database every so often to avoid
+        hammering the DB with writes. We don't need the timestamp to be precise,
+        as the timestamp is used to evict old entries that haven't been used in
+        a while.
+        """
+
+        now_ms = clock.time_msec()
+        return [
+            user_id
+            for user_id, last_seen_ts in self.returned_user_id_to_last_seen_ts_map.items()
+            if last_seen_ts is None
+            or now_ms - last_seen_ts >= LAZY_MEMBERS_UPDATE_INTERVAL.as_millis()
+        ]
+
+    def has_updates(self, clock: Clock) -> bool:
+        """Check if there are any updates to the lazy membership changes.
+
+        Called to check if we need to persist changes to the lazy membership
+        state for the room. We want to avoid persisting the state if there are
+        no changes, to avoid unnecessary writes (and cache misses due to new
+        connection position).
+        """
+
+        # We consider there to be updates if there are any invalidated user
+        # IDs...
+        if self.invalidated_user_ids:
+            return True
+
+        # ...or if any of the returned user IDs need their last seen timestamp
+        # updating in the database.
+        return bool(self.get_returned_user_ids_to_update(clock))
+
+
 @attr.s(auto_attribs=True)
 class MutablePerConnectionState(PerConnectionState):
     """A mutable version of `PerConnectionState`"""
@@ -903,12 +975,28 @@ class MutablePerConnectionState(PerConnectionState):
 
     room_configs: typing.ChainMap[str, RoomSyncConfig]
 
-    def has_updates(self) -> bool:
+    # A map from room ID to the lazily-loaded memberships needed for the
+    # request in that room.
+    room_lazy_membership: dict[str, RoomLazyMembershipChanges] = attr.Factory(dict)
+
+    def has_updates(self, clock: Clock) -> bool:
+        """Check if there are any updates to the per-connection state that need
+        persisting.
+
+        It is important that we don't spuriously do persistence, as that will
+        always generate a new connection position which will invalidate some of
+        the caches. It doesn't need to be perfect, but we should avoid always
+        generating new connection positions when doing lazy loading
+        """
         return (
             bool(self.rooms.get_updates())
             or bool(self.receipts.get_updates())
             or bool(self.account_data.get_updates())
             or bool(self.get_room_config_updates())
+            or any(
+                change.has_updates(clock)
+                for change in self.room_lazy_membership.values()
+            )
         )
 
     def get_room_config_updates(self) -> Mapping[str, RoomSyncConfig]:

synapse/util/clock.py

@@ -29,6 +29,7 @@ from twisted.internet.interfaces import IDelayedCall
 from twisted.internet.task import LoopingCall
 
 from synapse.logging import context
+from synapse.logging.loggers import ExplicitlyConfiguredLogger
 from synapse.types import ISynapseThreadlessReactor
 from synapse.util import log_failure
 from synapse.util.duration import Duration
@@ -39,6 +40,25 @@ P = ParamSpec("P")
 
 logger = logging.getLogger(__name__)
 
+original_logger_class = logging.getLoggerClass()
+logging.setLoggerClass(ExplicitlyConfiguredLogger)
+clock_debug_logger = logging.getLogger("synapse.util.clock.debug")
+"""
+A logger for debugging what is scheduling calls.
+
+Ideally, these wouldn't be gated behind an `ExplicitlyConfiguredLogger` as including logs
+from this logger would be helpful to track when things are being scheduled. However, for
+these logs to be meaningful, they need to include a stack trace to show what initiated the
+call in the first place.
+
+Since the stack traces can create a lot of noise and make the logs hard to read (unless you're
+specifically debugging scheduling issues) we want users to opt-in to seeing these logs. To enable
+this, they must explicitly set `synapse.util.clock.debug` in the logging configuration. Note that
+this setting won't inherit the log level from the parent logger.
+"""
+# Restore the original logger class
+logging.setLoggerClass(original_logger_class)
+
 
 class Clock:
     """
@@ -174,7 +194,7 @@ class Clock:
             looping_call_context_string = "looping_call_now"
 
         def wrapped_f(*args: P.args, **kwargs: P.kwargs) -> Deferred:
-            logger.debug(
+            clock_debug_logger.debug(
                 "%s(%s): Executing callback", looping_call_context_string, instance_id
             )
 
@@ -222,7 +242,7 @@ class Clock:
         d.addErrback(log_failure, "Looping call died", consumeErrors=False)
         self._looping_calls.append(call)
 
-        logger.debug(
+        clock_debug_logger.debug(
             "%s(%s): Scheduled looping call every %sms later",
             looping_call_context_string,
             instance_id,
@@ -283,7 +303,7 @@ class Clock:
             raise Exception("Cannot start delayed call. Clock has been shutdown")
 
         def wrapped_callback(*args: Any, **kwargs: Any) -> None:
-            logger.debug("call_later(%s): Executing callback", call_id)
+            clock_debug_logger.debug("call_later(%s): Executing callback", call_id)
 
             assert context.current_context() is context.SENTINEL_CONTEXT, (
                 "Expected `call_later` callback from the reactor to start with the sentinel logcontext "
@@ -327,7 +347,7 @@ class Clock:
             delay.as_secs(), wrapped_callback, *args, **kwargs
         )  # type: ignore[call-later-not-tracked]
 
-        logger.debug(
+        clock_debug_logger.debug(
             "call_later(%s): Scheduled call for %ss later (tracked for shutdown: %s)",
             call_id,
             delay,
@@ -347,7 +367,7 @@ class Clock:
         self, wrapped_call: "DelayedCallWrapper", ignore_errs: bool = False
     ) -> None:
         try:
-            logger.debug(
+            clock_debug_logger.debug(
                 "cancel_call_later: cancelling scheduled call %s", wrapped_call.call_id
             )
             wrapped_call.delayed_call.cancel()
@@ -367,7 +387,7 @@ class Clock:
         # will result in the call removing itself from the map mid-iteration.
         for call_id, call in list(self._call_id_to_delayed_call.items()):
             try:
-                logger.debug(
+                clock_debug_logger.debug(
                     "cancel_all_delayed_calls: cancelling scheduled call %s", call_id
                 )
                 call.cancel()
@@ -396,7 +416,9 @@ class Clock:
         instance_id = random_string_insecure_fast(5)
 
         def wrapped_callback(*args: Any, **kwargs: Any) -> None:
-            logger.debug("call_when_running(%s): Executing callback", instance_id)
+            clock_debug_logger.debug(
+                "call_when_running(%s): Executing callback", instance_id
+            )
 
             # Since this callback can be invoked immediately if the reactor is already
             # running, we can't always assume that we're running in the sentinel
@@ -436,7 +458,7 @@ class Clock:
         # callWhenRunning should be called.
         self._reactor.callWhenRunning(wrapped_callback, *args, **kwargs)  # type: ignore[prefer-synapse-clock-call-when-running]
 
-        logger.debug(
+        clock_debug_logger.debug(
             "call_when_running(%s): Scheduled call",
             instance_id,
             # Find out who is scheduling the call which makes it easy to follow in the
@@ -472,7 +494,7 @@ class Clock:
         instance_id = random_string_insecure_fast(5)
 
         def wrapped_callback(*args: Any, **kwargs: Any) -> None:
-            logger.debug(
+            clock_debug_logger.debug(
                 "add_system_event_trigger(%s): Executing %s %s callback",
                 instance_id,
                 phase,
@@ -509,7 +531,7 @@ class Clock:
                 # logcontext to the reactor
                 context.run_in_background(callback, *args, **kwargs)
 
-        logger.debug(
+        clock_debug_logger.debug(
             "add_system_event_trigger(%s) for %s %s",
             instance_id,
             phase,

synapse/util/file_consumer.py

@@ -19,7 +19,7 @@
 #
 
 import queue
-from typing import Any, BinaryIO, cast
+from typing import Any, BinaryIO, Optional, Union, cast
 
 from twisted.internet import threads
 from twisted.internet.defer import Deferred
@@ -50,7 +50,7 @@ class BackgroundFileConsumer:
         self._reactor: ISynapseReactor = reactor
 
         # Producer we're registered with
-        self._producer: IPushProducer | IPullProducer | None = None
+        self._producer: Optional[Union[IPushProducer, IPullProducer]] = None
 
         # True if PushProducer, false if PullProducer
         self.streaming = False
@@ -72,7 +72,7 @@ class BackgroundFileConsumer:
         self._write_exception: Exception | None = None
 
     def registerProducer(
-        self, producer: IPushProducer | IPullProducer, streaming: bool
+        self, producer: Union[IPushProducer, IPullProducer], streaming: bool
     ) -> None:
         """Part of IConsumer interface
 

synapse/util/iterutils.py

@@ -22,6 +22,7 @@
 import heapq
 from itertools import islice
 from typing import (
+    Any,
     Callable,
     Collection,
     Generator,
@@ -33,7 +34,7 @@ from typing import (
     TypeVar,
 )
 
-T = TypeVar("T")
+T = TypeVar("T", bound=Any)
 S = TypeVar("S", bound="_SelfSlice")
 
 

tests/app/test_homeserver_shutdown.py

@@ -19,7 +19,10 @@
 #
 
 import gc
+import sys
 import weakref
+from typing import Any
+from unittest.mock import patch
 
 from synapse.app.homeserver import SynapseHomeServer
 from synapse.logging.context import LoggingContext
@@ -81,45 +84,12 @@ class HomeserverCleanShutdownTestCase(HomeserverTestCase):
 
         # Ensure the `HomeServer` hs been garbage collected by attempting to use the
         # weakref to it.
-        if hs_ref() is not None:
-            self.fail("HomeServer reference should not be valid at this point")
-
-            # To help debug this test when it fails, it is useful to leverage the
-            # `objgraph` module.
-            # The following code serves as an example of what I have found to be useful
-            # when tracking down references holding the `SynapseHomeServer` in memory:
-            #
-            # all_objects = gc.get_objects()
-            # for obj in all_objects:
-            #     try:
-            #         # These are a subset of types that are typically involved with
-            #         # holding the `HomeServer` in memory. You may want to inspect
-            #         # other types as well.
-            #         if isinstance(obj, DataStore):
-            #             print(sys.getrefcount(obj), "refs to", obj)
-            #             if not isinstance(obj, weakref.ProxyType):
-            #                 db_obj = obj
-            #         if isinstance(obj, SynapseHomeServer):
-            #             print(sys.getrefcount(obj), "refs to", obj)
-            #             if not isinstance(obj, weakref.ProxyType):
-            #                 synapse_hs = obj
-            #         if isinstance(obj, SynapseSite):
-            #             print(sys.getrefcount(obj), "refs to", obj)
-            #             if not isinstance(obj, weakref.ProxyType):
-            #                 sysite = obj
-            #         if isinstance(obj, DatabasePool):
-            #             print(sys.getrefcount(obj), "refs to", obj)
-            #             if not isinstance(obj, weakref.ProxyType):
-            #                 dbpool = obj
-            #     except Exception:
-            #         pass
-            #
-            # print(sys.getrefcount(hs_ref()), "refs to", hs_ref())
-            #
-            # # The following values for `max_depth` and `too_many` have been found to
-            # # render a useful amount of information without taking an overly long time
-            # # to generate the result.
-            # objgraph.show_backrefs(synapse_hs, max_depth=10, too_many=10)
+        hs_after_shutdown = hs_ref()
+        if hs_after_shutdown is not None:
+            self.fail(
+                "HomeServer reference should not be valid at this point "
+                f"{get_memory_debug_info_for_object(hs_after_shutdown)}",
+            )
 
     @logcontext_clean
     def test_clean_homeserver_shutdown_mid_background_updates(self) -> None:
@@ -165,42 +135,137 @@ class HomeserverCleanShutdownTestCase(HomeserverTestCase):
 
         # Ensure the `HomeServer` hs been garbage collected by attempting to use the
         # weakref to it.
-        if hs_ref() is not None:
-            self.fail("HomeServer reference should not be valid at this point")
+        hs_after_shutdown = hs_ref()
+        if hs_after_shutdown is not None:
+            self.fail(
+                "HomeServer reference should not be valid at this point "
+                f"{get_memory_debug_info_for_object(hs_after_shutdown)}",
+            )
 
-            # To help debug this test when it fails, it is useful to leverage the
-            # `objgraph` module.
-            # The following code serves as an example of what I have found to be useful
-            # when tracking down references holding the `SynapseHomeServer` in memory:
-            #
-            # all_objects = gc.get_objects()
-            # for obj in all_objects:
-            #     try:
-            #         # These are a subset of types that are typically involved with
-            #         # holding the `HomeServer` in memory. You may want to inspect
-            #         # other types as well.
-            #         if isinstance(obj, DataStore):
-            #             print(sys.getrefcount(obj), "refs to", obj)
-            #             if not isinstance(obj, weakref.ProxyType):
-            #                 db_obj = obj
-            #         if isinstance(obj, SynapseHomeServer):
-            #             print(sys.getrefcount(obj), "refs to", obj)
-            #             if not isinstance(obj, weakref.ProxyType):
-            #                 synapse_hs = obj
-            #         if isinstance(obj, SynapseSite):
-            #             print(sys.getrefcount(obj), "refs to", obj)
-            #             if not isinstance(obj, weakref.ProxyType):
-            #                 sysite = obj
-            #         if isinstance(obj, DatabasePool):
-            #             print(sys.getrefcount(obj), "refs to", obj)
-            #             if not isinstance(obj, weakref.ProxyType):
-            #                 dbpool = obj
-            #     except Exception:
-            #         pass
-            #
-            # print(sys.getrefcount(hs_ref()), "refs to", hs_ref())
-            #
-            # # The following values for `max_depth` and `too_many` have been found to
-            # # render a useful amount of information without taking an overly long time
-            # # to generate the result.
-            # objgraph.show_backrefs(synapse_hs, max_depth=10, too_many=10)
+    @logcontext_clean
+    def test_clean_homeserver_shutdown_when_failed_to_setup(self) -> None:
+        """
+        Ensure the `SynapseHomeServer` can be fully shutdown and garbage collected if it
+        fails to be `setup`.
+        """
+        self.reactor, self.clock = get_clock()
+
+        # Patch `hs.setup()` to do nothing, so that the homeserver is not fully setup.
+        with patch.object(SynapseHomeServer, "setup", return_value=None) as mock_setup:
+            # Patch out the call to `start_test_homeserver` since we want access to the
+            # homeserver even before the server is setup (let alone started)
+            with patch("tests.server.start_test_homeserver", return_value=None):
+                self.hs = setup_test_homeserver(
+                    cleanup_func=self.addCleanup,
+                    reactor=self.reactor,
+                    homeserver_to_use=SynapseHomeServer,
+                    clock=self.clock,
+                )
+            # Sanity check that we patched the correct method (make sure it was the
+            # thing that was called)
+            mock_setup.assert_called_once_with()
+
+        hs_ref = weakref.ref(self.hs)
+
+        # Run the reactor so any `callWhenRunning` functions can be cleared out.
+        self.reactor.run()
+        # This would normally happen as part of `HomeServer.shutdown` but the `MemoryReactor`
+        # we use in tests doesn't handle this properly (see doc comment)
+        cleanup_test_reactor_system_event_triggers(self.reactor)
+
+        async def shutdown() -> None:
+            # Use a logcontext just to double-check that we don't mangle the logcontext
+            # during shutdown.
+            with LoggingContext(name="hs_shutdown", server_name=self.hs.hostname):
+                await self.hs.shutdown()
+
+        self.get_success(shutdown())
+
+        # Cleanup the internal reference in our test case
+        del self.hs
+
+        # Force garbage collection.
+        gc.collect()
+
+        # Ensure the `HomeServer` hs been garbage collected by attempting to use the
+        # weakref to it.
+        hs_after_shutdown = hs_ref()
+        if hs_after_shutdown is not None:
+            self.fail(
+                "HomeServer reference should not be valid at this point "
+                f"{get_memory_debug_info_for_object(hs_after_shutdown)}",
+            )
+
+
+def get_memory_debug_info_for_object(object: Any) -> dict[str, Any]:
+    """
+    Gathers some useful information to make it easier to figure out why the `object` is
+    still in memory.
+
+    Args:
+        object: The object to gather debug information for.
+    """
+    debug: dict[str, Any] = {}
+    if object is not None:
+        # The simplest tracing we can do is show the reference count for the object.
+        debug["reference_count"] = sys.getrefcount(object)
+
+        # Find the list of objects that directly refer to the object.
+        #
+        # Note: The `ref_count` can be >0 but `referrers` can be empty because
+        # the all of the objects were frozen. Look at the
+        # `frozen_object_count` to detect this scenario.
+        referrers = gc.get_referrers(object)
+        debug["gc_referrer_count"] = len(referrers)
+        debug["gc_referrers"] = referrers
+
+        # We don't expect to see frozen objects in normal operation of the
+        # `multi_synapse` shard.
+        #
+        # We can see frozen objects if you forget to `freeze=False` when
+        # starting the `SynapseHomeServer`. Frozen objects mean they are
+        # never considered for garbage collection. If the
+        # `SynapseHomeServer` (or anything that references the homeserver)
+        # is frozen, the homeserver can never be garbage collected and will
+        # linger in memory forever.
+        freeze_count = gc.get_freeze_count()
+        debug["gc_global_frozen_object_count"] = freeze_count
+
+    # To help debug this test when it fails, it is useful to leverage the
+    # `objgraph` module.
+    # The following code serves as an example of what I have found to be useful
+    # when tracking down references holding the `SynapseHomeServer` in memory:
+    #
+    # all_objects = gc.get_objects()
+    # for obj in all_objects:
+    #     try:
+    #         # These are a subset of types that are typically involved with
+    #         # holding the `HomeServer` in memory. You may want to inspect
+    #         # other types as well.
+    #         if isinstance(obj, DataStore):
+    #             print(sys.getrefcount(obj), "refs to", obj)
+    #             if not isinstance(obj, weakref.ProxyType):
+    #                 db_obj = obj
+    #         if isinstance(obj, SynapseHomeServer):
+    #             print(sys.getrefcount(obj), "refs to", obj)
+    #             if not isinstance(obj, weakref.ProxyType):
+    #                 synapse_hs = obj
+    #         if isinstance(obj, SynapseSite):
+    #             print(sys.getrefcount(obj), "refs to", obj)
+    #             if not isinstance(obj, weakref.ProxyType):
+    #                 sysite = obj
+    #         if isinstance(obj, DatabasePool):
+    #             print(sys.getrefcount(obj), "refs to", obj)
+    #             if not isinstance(obj, weakref.ProxyType):
+    #                 dbpool = obj
+    #     except Exception:
+    #         pass
+    #
+    # print(sys.getrefcount(hs_ref()), "refs to", hs_ref())
+    #
+    # # The following values for `max_depth` and `too_many` have been found to
+    # # render a useful amount of information without taking an overly long time
+    # # to generate the result.
+    # objgraph.show_backrefs(synapse_hs, max_depth=10, too_many=10)
+
+    return debug

tests/crypto/test_keyring.py

@@ -95,7 +95,12 @@ class KeyringTestCase(unittest.HomeserverTestCase):
     def test_verify_json_objects_for_server_awaits_previous_requests(self) -> None:
         mock_fetcher = Mock()
         mock_fetcher.get_keys = Mock()
-        kr = keyring.Keyring(self.hs, key_fetchers=(mock_fetcher,))
+        kr = keyring.Keyring(
+            self.hs,
+            test_only_key_fetchers=[
+                mock_fetcher,
+            ],
+        )
 
         # a signed object that we are going to try to validate
         key1 = signedjson.key.generate_signing_key("1")
@@ -286,7 +291,7 @@ class KeyringTestCase(unittest.HomeserverTestCase):
         mock_fetcher = Mock()
         mock_fetcher.get_keys = Mock(side_effect=get_keys)
         kr = keyring.Keyring(
-            self.hs, key_fetchers=(StoreKeyFetcher(self.hs), mock_fetcher)
+            self.hs, test_only_key_fetchers=[StoreKeyFetcher(self.hs), mock_fetcher]
         )
 
         # sign the json
@@ -313,7 +318,7 @@ class KeyringTestCase(unittest.HomeserverTestCase):
 
         mock_fetcher = Mock()
         mock_fetcher.get_keys = Mock(side_effect=get_keys)
-        kr = keyring.Keyring(self.hs, key_fetchers=(mock_fetcher,))
+        kr = keyring.Keyring(self.hs, test_only_key_fetchers=[mock_fetcher])
 
         json1: JsonDict = {}
         signedjson.sign.sign_json(json1, "server1", key1)
@@ -363,7 +368,9 @@ class KeyringTestCase(unittest.HomeserverTestCase):
         mock_fetcher1.get_keys = Mock(side_effect=get_keys1)
         mock_fetcher2 = Mock()
         mock_fetcher2.get_keys = Mock(side_effect=get_keys2)
-        kr = keyring.Keyring(self.hs, key_fetchers=(mock_fetcher1, mock_fetcher2))
+        kr = keyring.Keyring(
+            self.hs, test_only_key_fetchers=[mock_fetcher1, mock_fetcher2]
+        )
 
         json1: JsonDict = {}
         signedjson.sign.sign_json(json1, "server1", key1)

tests/handlers/test_sliding_sync.py

@@ -18,7 +18,7 @@
 #
 #
 import logging
-from typing import AbstractSet, Mapping
+from typing import AbstractSet
 from unittest.mock import patch
 
 import attr
@@ -38,13 +38,17 @@ from synapse.handlers.sliding_sync import (
     RoomSyncConfig,
     StateValues,
     _required_state_changes,
+    _RequiredStateChangesReturn,
 )
 from synapse.rest import admin
 from synapse.rest.client import knock, login, room
 from synapse.server import HomeServer
 from synapse.storage.util.id_generators import MultiWriterIdGenerator
 from synapse.types import JsonDict, StateMap, StreamToken, UserID, create_requester
-from synapse.types.handlers.sliding_sync import PerConnectionState, SlidingSyncConfig
+from synapse.types.handlers.sliding_sync import (
+    PerConnectionState,
+    SlidingSyncConfig,
+)
 from synapse.types.state import StateFilter
 from synapse.util.clock import Clock
 
@@ -3827,12 +3831,11 @@ class RequiredStateChangesTestParameters:
     previous_required_state_map: dict[str, set[str]]
     request_required_state_map: dict[str, set[str]]
     state_deltas: StateMap[str]
-    expected_with_state_deltas: tuple[
-        Mapping[str, AbstractSet[str]] | None, StateFilter
-    ]
-    expected_without_state_deltas: tuple[
-        Mapping[str, AbstractSet[str]] | None, StateFilter
-    ]
+    expected_with_state_deltas: _RequiredStateChangesReturn
+    expected_without_state_deltas: _RequiredStateChangesReturn
+
+    previously_returned_lazy_user_ids: AbstractSet[str] = frozenset()
+    request_lazy_load_user_ids: AbstractSet[str] = frozenset()
 
 
 class RequiredStateChangesTestCase(unittest.TestCase):
@@ -3848,8 +3851,12 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                     request_required_state_map={"type1": {"state_key"}},
                     state_deltas={("type1", "state_key"): "$event_id"},
                     # No changes
-                    expected_with_state_deltas=(None, StateFilter.none()),
-                    expected_without_state_deltas=(None, StateFilter.none()),
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
+                        None, StateFilter.none()
+                    ),
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
+                        None, StateFilter.none()
+                    ),
                 ),
             ),
             (
@@ -3862,14 +3869,14 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                         "type2": {"state_key"},
                     },
                     state_deltas={("type2", "state_key"): "$event_id"},
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         # We've added a type so we should persist the changed required state
                         # config.
                         {"type1": {"state_key"}, "type2": {"state_key"}},
                         # We should see the new type added
                         StateFilter.from_types([("type2", "state_key")]),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         {"type1": {"state_key"}, "type2": {"state_key"}},
                         StateFilter.from_types([("type2", "state_key")]),
                     ),
@@ -3885,7 +3892,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                         "type2": {"state_key"},
                     },
                     state_deltas={("type2", "state_key"): "$event_id"},
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         # We've added a type so we should persist the changed required state
                         # config.
                         {"type1": {"state_key"}, "type2": {"state_key"}},
@@ -3894,7 +3901,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                             [("type1", "state_key"), ("type2", "state_key")]
                         ),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         {"type1": {"state_key"}, "type2": {"state_key"}},
                         StateFilter.from_types(
                             [("type1", "state_key"), ("type2", "state_key")]
@@ -3909,14 +3916,14 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                     previous_required_state_map={"type": {"state_key1"}},
                     request_required_state_map={"type": {"state_key1", "state_key2"}},
                     state_deltas={("type", "state_key2"): "$event_id"},
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         # We've added a key so we should persist the changed required state
                         # config.
                         {"type": {"state_key1", "state_key2"}},
                         # We should see the new state_keys added
                         StateFilter.from_types([("type", "state_key2")]),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         {"type": {"state_key1", "state_key2"}},
                         StateFilter.from_types([("type", "state_key2")]),
                     ),
@@ -3929,7 +3936,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                     previous_required_state_map={"type": {"state_key1"}},
                     request_required_state_map={"type": {"state_key2", "state_key3"}},
                     state_deltas={("type", "state_key2"): "$event_id"},
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         # We've added a key so we should persist the changed required state
                         # config.
                         #
@@ -3940,7 +3947,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                             [("type", "state_key2"), ("type", "state_key3")]
                         ),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         {"type": {"state_key1", "state_key2", "state_key3"}},
                         StateFilter.from_types(
                             [("type", "state_key2"), ("type", "state_key3")]
@@ -3964,7 +3971,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                     },
                     request_required_state_map={"type1": {"state_key"}},
                     state_deltas={("type2", "state_key"): "$event_id"},
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         # Remove `type2` since there's been a change to that state,
                         # (persist the change to required state). That way next time,
                         # they request `type2`, we see that we haven't sent it before
@@ -3975,7 +3982,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                         # less state now
                         StateFilter.none(),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         # `type2` is no longer requested but since that state hasn't
                         # changed, nothing should change (we should still keep track
                         # that we've sent `type2` before).
@@ -3998,7 +4005,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                     },
                     request_required_state_map={},
                     state_deltas={("type2", "state_key"): "$event_id"},
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         # Remove `type2` since there's been a change to that state,
                         # (persist the change to required state). That way next time,
                         # they request `type2`, we see that we haven't sent it before
@@ -4009,7 +4016,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                         # less state now
                         StateFilter.none(),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         # `type2` is no longer requested but since that state hasn't
                         # changed, nothing should change (we should still keep track
                         # that we've sent `type2` before).
@@ -4029,7 +4036,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                     previous_required_state_map={"type": {"state_key1", "state_key2"}},
                     request_required_state_map={"type": {"state_key1"}},
                     state_deltas={("type", "state_key2"): "$event_id"},
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         # Remove `(type, state_key2)` since there's been a change
                         # to that state (persist the change to required state).
                         # That way next time, they request `(type, state_key2)`, we see
@@ -4041,7 +4048,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                         # less state now
                         StateFilter.none(),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         # `(type, state_key2)` is no longer requested but since that
                         # state hasn't changed, nothing should change (we should still
                         # keep track that we've sent `(type, state_key1)` and `(type,
@@ -4073,11 +4080,11 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                         ("other_type", "state_key"): "$event_id",
                     },
                     # We've added a wildcard, so we persist the change and request everything
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         {"type1": {"state_key2"}, StateValues.WILDCARD: {"state_key"}},
                         StateFilter.all(),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         {"type1": {"state_key2"}, StateValues.WILDCARD: {"state_key"}},
                         StateFilter.all(),
                     ),
@@ -4103,13 +4110,13 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                         ("other_type", "state_key"): "$event_id",
                     },
                     # We've removed a type wildcard, so we persist the change but don't request anything
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         {"type1": {"state_key2"}},
                         # We don't need to request anything more if they are requesting
                         # less state now
                         StateFilter.none(),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         {"type1": {"state_key2"}},
                         # We don't need to request anything more if they are requesting
                         # less state now
@@ -4129,11 +4136,11 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                     state_deltas={("type2", "state_key"): "$event_id"},
                     # We've added a wildcard state_key, so we persist the change and
                     # request all of the state for that type
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         {"type1": {"state_key"}, "type2": {StateValues.WILDCARD}},
                         StateFilter.from_types([("type2", None)]),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         {"type1": {"state_key"}, "type2": {StateValues.WILDCARD}},
                         StateFilter.from_types([("type2", None)]),
                     ),
@@ -4151,7 +4158,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                     state_deltas={("type2", "state_key"): "$event_id"},
                     # We've removed a state_key wildcard, so we persist the change and
                     # request nothing
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         {"type1": {"state_key"}},
                         # We don't need to request anything more if they are requesting
                         # less state now
@@ -4160,7 +4167,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                     # We've removed a state_key wildcard but there have been no matching
                     # state changes, so no changes needed, just persist the
                     # `request_required_state_map` as-is.
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         None,
                         # We don't need to request anything more if they are requesting
                         # less state now
@@ -4180,7 +4187,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                     },
                     request_required_state_map={"type1": {"state_key1"}},
                     state_deltas={("type1", "state_key3"): "$event_id"},
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         # We've removed some state keys from the type, but only state_key3 was
                         # changed so only that one should be removed.
                         {"type1": {"state_key1", "state_key2"}},
@@ -4188,7 +4195,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                         # less state now
                         StateFilter.none(),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         # No changes needed, just persist the
                         # `request_required_state_map` as-is
                         None,
@@ -4207,14 +4214,14 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                     previous_required_state_map={},
                     request_required_state_map={"type1": {StateValues.ME}},
                     state_deltas={("type1", "@user:test"): "$event_id"},
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         # We've added a type so we should persist the changed required state
                         # config.
                         {"type1": {StateValues.ME}},
                         # We should see the new state_keys added
                         StateFilter.from_types([("type1", "@user:test")]),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         {"type1": {StateValues.ME}},
                         StateFilter.from_types([("type1", "@user:test")]),
                     ),
@@ -4229,7 +4236,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                     previous_required_state_map={"type1": {StateValues.ME}},
                     request_required_state_map={},
                     state_deltas={("type1", "@user:test"): "$event_id"},
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         # Remove `type1` since there's been a change to that state,
                         # (persist the change to required state). That way next time,
                         # they request `type1`, we see that we haven't sent it before
@@ -4240,7 +4247,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                         # less state now
                         StateFilter.none(),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         # `type1` is no longer requested but since that state hasn't
                         # changed, nothing should change (we should still keep track
                         # that we've sent `type1` before).
@@ -4260,14 +4267,14 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                     previous_required_state_map={},
                     request_required_state_map={"type1": {"@user:test"}},
                     state_deltas={("type1", "@user:test"): "$event_id"},
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         # We've added a type so we should persist the changed required state
                         # config.
                         {"type1": {"@user:test"}},
                         # We should see the new state_keys added
                         StateFilter.from_types([("type1", "@user:test")]),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         {"type1": {"@user:test"}},
                         StateFilter.from_types([("type1", "@user:test")]),
                     ),
@@ -4282,7 +4289,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                     previous_required_state_map={"type1": {"@user:test"}},
                     request_required_state_map={},
                     state_deltas={("type1", "@user:test"): "$event_id"},
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         # Remove `type1` since there's been a change to that state,
                         # (persist the change to required state). That way next time,
                         # they request `type1`, we see that we haven't sent it before
@@ -4293,7 +4300,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                         # less state now
                         StateFilter.none(),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         # `type1` is no longer requested but since that state hasn't
                         # changed, nothing should change (we should still keep track
                         # that we've sent `type1` before).
@@ -4313,13 +4320,13 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                     previous_required_state_map={},
                     request_required_state_map={EventTypes.Member: {StateValues.LAZY}},
                     state_deltas={(EventTypes.Member, "@user:test"): "$event_id"},
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         # If a "$LAZY" has been added or removed we always update the
                         # required state to what was requested for simplicity.
                         {EventTypes.Member: {StateValues.LAZY}},
                         StateFilter.none(),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         {EventTypes.Member: {StateValues.LAZY}},
                         StateFilter.none(),
                     ),
@@ -4334,7 +4341,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                     previous_required_state_map={EventTypes.Member: {StateValues.LAZY}},
                     request_required_state_map={},
                     state_deltas={(EventTypes.Member, "@user:test"): "$event_id"},
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         # If a "$LAZY" has been added or removed we always update the
                         # required state to what was requested for simplicity.
                         {},
@@ -4342,7 +4349,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                         # less state now
                         StateFilter.none(),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         # `EventTypes.Member` is no longer requested but since that
                         # state hasn't changed, nothing should change (we should still
                         # keep track that we've sent `EventTypes.Member` before).
@@ -4361,41 +4368,40 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                 we're sending down another response without any timeline events.
                 """,
                 RequiredStateChangesTestParameters(
-                    previous_required_state_map={
-                        EventTypes.Member: {
-                            StateValues.LAZY,
-                            "@user2:test",
-                            "@user3:test",
-                        }
-                    },
+                    previous_required_state_map={EventTypes.Member: {StateValues.LAZY}},
                     request_required_state_map={EventTypes.Member: {StateValues.LAZY}},
+                    previously_returned_lazy_user_ids={"@user2:test", "@user3:test"},
+                    request_lazy_load_user_ids=set(),
                     state_deltas={(EventTypes.Member, "@user2:test"): "$event_id"},
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
+                        # The `request_required_state_map` hasn't changed
+                        None,
+                        # We don't need to request anything more if they are requesting
+                        # less state now
+                        StateFilter.none(),
+                        # Previous request did not include any explicit members,
+                        # so there is no extra users to add to the lazy cache.
+                        extra_users_to_add_to_lazy_cache=frozenset(),
                         # Remove "@user2:test" since that state has changed and is no
                         # longer being requested anymore. Since something was removed,
                         # we should persist the changed to required state. That way next
                         # time, they request "@user2:test", we see that we haven't sent
                         # it before and send the new state. (we should still keep track
                         # that we've sent specific `EventTypes.Member` before)
-                        {
-                            EventTypes.Member: {
-                                StateValues.LAZY,
-                                "@user3:test",
-                            }
-                        },
-                        # We don't need to request anything more if they are requesting
-                        # less state now
-                        StateFilter.none(),
+                        lazy_members_invalidated={"@user2:test"},
                     ),
-                    expected_without_state_deltas=(
-                        # We're not requesting any specific `EventTypes.Member` now but
-                        # since that state hasn't changed, nothing should change (we
-                        # should still keep track that we've sent specific
-                        # `EventTypes.Member` before).
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
+                        # The `request_required_state_map` hasn't changed
                         None,
                         # We don't need to request anything more if they are requesting
                         # less state now
                         StateFilter.none(),
+                        # Previous request did not include any explicit members,
+                        # so there is no extra users to add to the lazy cache.
+                        extra_users_to_add_to_lazy_cache=frozenset(),
+                        # Nothing should change (we should still keep track that
+                        # we've sent specific `EventTypes.Member` before).
+                        lazy_members_invalidated=frozenset(),
                     ),
                 ),
             ),
@@ -4407,50 +4413,37 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                 we're sending down another response with a new event from user4.
                 """,
                 RequiredStateChangesTestParameters(
-                    previous_required_state_map={
-                        EventTypes.Member: {
-                            StateValues.LAZY,
-                            "@user2:test",
-                            "@user3:test",
-                        }
-                    },
-                    request_required_state_map={
-                        EventTypes.Member: {StateValues.LAZY, "@user4:test"}
-                    },
+                    previous_required_state_map={EventTypes.Member: {StateValues.LAZY}},
+                    request_required_state_map={EventTypes.Member: {StateValues.LAZY}},
+                    previously_returned_lazy_user_ids={"@user2:test", "@user3:test"},
+                    request_lazy_load_user_ids={"@user4:test"},
                     state_deltas={(EventTypes.Member, "@user2:test"): "$event_id"},
-                    expected_with_state_deltas=(
-                        # Since "@user4:test" was added, we should persist the changed
-                        # required state config.
-                        #
-                        # Also remove "@user2:test" since that state has changed and is no
-                        # longer being requested anymore. Since something was removed,
-                        # we also should persist the changed to required state. That way next
-                        # time, they request "@user2:test", we see that we haven't sent
-                        # it before and send the new state. (we should still keep track
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
+                        # The `request_required_state_map` hasn't changed
+                        None,
+                        # We should see the new state_keys added
+                        StateFilter.from_types([(EventTypes.Member, "@user4:test")]),
+                        # Previous request did not include any explicit members,
+                        # so there is no extra users to add to the lazy cache.
+                        extra_users_to_add_to_lazy_cache=frozenset(),
+                        # Remove "@user2:test" since that state has changed and
+                        # is no longer being requested anymore. Since something
+                        # was removed, we also should persist the changed to
+                        # required state. That way next time, they request
+                        # "@user2:test", we see that we haven't sent it before
+                        # and send the new state. (we should still keep track
                         # that we've sent specific `EventTypes.Member` before)
-                        {
-                            EventTypes.Member: {
-                                StateValues.LAZY,
-                                "@user3:test",
-                                "@user4:test",
-                            }
-                        },
-                        # We should see the new state_keys added
-                        StateFilter.from_types([(EventTypes.Member, "@user4:test")]),
+                        lazy_members_invalidated={"@user2:test"},
                     ),
-                    expected_without_state_deltas=(
-                        # Since "@user4:test" was added, we should persist the changed
-                        # required state config.
-                        {
-                            EventTypes.Member: {
-                                StateValues.LAZY,
-                                "@user2:test",
-                                "@user3:test",
-                                "@user4:test",
-                            }
-                        },
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
+                        # The `request_required_state_map` hasn't changed
+                        None,
                         # We should see the new state_keys added
                         StateFilter.from_types([(EventTypes.Member, "@user4:test")]),
+                        # Previous request did not include any explicit members,
+                        # so there is no extra users to add to the lazy cache.
+                        extra_users_to_add_to_lazy_cache=frozenset(),
+                        lazy_members_invalidated=frozenset(),
                     ),
                 ),
             ),
@@ -4464,40 +4457,81 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                         EventTypes.Member: {"@user2:test", "@user3:test"}
                     },
                     request_required_state_map={EventTypes.Member: {StateValues.LAZY}},
+                    previously_returned_lazy_user_ids=frozenset(),
+                    request_lazy_load_user_ids=frozenset(),
                     state_deltas={(EventTypes.Member, "@user2:test"): "$event_id"},
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         # Since `StateValues.LAZY` was added, we should persist the
                         # changed required state config.
-                        #
-                        # Also remove "@user2:test" since that state has changed and is no
-                        # longer being requested anymore. Since something was removed,
-                        # we also should persist the changed to required state. That way next
-                        # time, they request "@user2:test", we see that we haven't sent
-                        # it before and send the new state. (we should still keep track
-                        # that we've sent specific `EventTypes.Member` before)
-                        {
-                            EventTypes.Member: {
-                                StateValues.LAZY,
-                                "@user3:test",
-                            }
-                        },
-                        # We don't need to request anything more if they are requesting
-                        # less state now
+                        {EventTypes.Member: {StateValues.LAZY}},
+                        # No users are being lazy loaded, so nothing to request.
                         StateFilter.none(),
+                        # Remember the fact that we've sent @user3 down before,
+                        # but not @user2 as that has been invalidated.
+                        extra_users_to_add_to_lazy_cache={"@user3:test"},
+                        # Nothing to invalidate as there are no existing lazy members.
+                        lazy_members_invalidated=frozenset(),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         # Since `StateValues.LAZY` was added, we should persist the
                         # changed required state config.
-                        {
-                            EventTypes.Member: {
-                                StateValues.LAZY,
-                                "@user2:test",
-                                "@user3:test",
-                            }
-                        },
-                        # We don't need to request anything more if they are requesting
-                        # less state now
+                        {EventTypes.Member: {StateValues.LAZY}},
+                        # No users are being lazy loaded, so nothing to request.
                         StateFilter.none(),
+                        # Remember the fact that we've sent the users down before.
+                        extra_users_to_add_to_lazy_cache={"@user2:test", "@user3:test"},
+                        # Nothing to invalidate as there are no existing lazy members.
+                        lazy_members_invalidated=frozenset(),
+                    ),
+                ),
+            ),
+            (
+                "state_key_expand_lazy_keep_previous_memberships_need_previous_sent",
+                """
+                Test expanding the `required_state` to lazy-loading room
+                members. If a previously explicit membership is requested then
+                we should not send it again (as it was already sent before).
+                """,
+                RequiredStateChangesTestParameters(
+                    previous_required_state_map={
+                        EventTypes.Member: {"@user2:test", "@user3:test"}
+                    },
+                    request_required_state_map={EventTypes.Member: {StateValues.LAZY}},
+                    previously_returned_lazy_user_ids=frozenset(),
+                    request_lazy_load_user_ids={"@user3:test"},
+                    state_deltas={(EventTypes.Member, "@user2:test"): "$event_id"},
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
+                        # Since `StateValues.LAZY` was added, we should persist the
+                        # changed required state config.
+                        {EventTypes.Member: {StateValues.LAZY}},
+                        # We have already sent @user3 down before.
+                        #
+                        # `@user3:test` is required for lazy loading, but we've
+                        # already sent it down before (due to it being in
+                        # `previous_required_state_map`), so we don't need to
+                        # request it again.
+                        StateFilter.none(),
+                        # Remember the fact that we've sent @user3 down before,
+                        # but not @user2 as that has been invalidated.
+                        extra_users_to_add_to_lazy_cache={"@user3:test"},
+                        # Nothing to invalidate as there are no existing lazy members.
+                        lazy_members_invalidated=frozenset(),
+                    ),
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
+                        # Since `StateValues.LAZY` was added, we should persist the
+                        # changed required state config.
+                        {EventTypes.Member: {StateValues.LAZY}},
+                        # We have already sent @user3 down before.
+                        #
+                        # `@user3:test` is required for lazy loading, but we've
+                        # already sent it down before (due to it being in
+                        # `previous_required_state_map`), so we don't need to
+                        # request it again.
+                        StateFilter.none(),
+                        # Remember the fact that we've sent the users down before.
+                        extra_users_to_add_to_lazy_cache={"@user2:test", "@user3:test"},
+                        # Nothing to invalidate as there are no existing lazy members.
+                        lazy_members_invalidated=frozenset(),
                     ),
                 ),
             ),
@@ -4507,36 +4541,33 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                 Test retracting the `required_state` to no longer lazy-loading room members.
                 """,
                 RequiredStateChangesTestParameters(
-                    previous_required_state_map={
-                        EventTypes.Member: {
-                            StateValues.LAZY,
-                            "@user2:test",
-                            "@user3:test",
-                        }
-                    },
+                    previous_required_state_map={EventTypes.Member: {StateValues.LAZY}},
                     request_required_state_map={},
+                    previously_returned_lazy_user_ids={"@user2:test", "@user3:test"},
+                    request_lazy_load_user_ids=set(),
                     state_deltas={(EventTypes.Member, "@user2:test"): "$event_id"},
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         # Remove `EventTypes.Member` since there's been a change to that
-                        # state, (persist the change to required state). That way next
-                        # time, they request `EventTypes.Member`, we see that we haven't
-                        # sent it before and send the new state. (if we were tracking
-                        # that we sent any other state, we should still keep track
-                        # that).
-                        #
-                        # This acts the same as the `simple_remove_type` test. It's
-                        # possible that we could remember the specific `state_keys` that
-                        # we have sent down before but this currently just acts the same
-                        # as if a whole `type` was removed. Perhaps it's good that we
-                        # "garbage collect" and forget what we've sent before for a
-                        # given `type`  when the client stops caring about a certain
-                        # `type`.
+                        # state, (persist the change to required state).
                         {},
                         # We don't need to request anything more if they are requesting
                         # less state now
                         StateFilter.none(),
+                        # Previous request did not include any explicit members,
+                        # so there is no extra users to add to the lazy cache.
+                        extra_users_to_add_to_lazy_cache=frozenset(),
+                        # Explicitly remove the now invalidated @user2:test
+                        # membership.
+                        #
+                        # We don't invalidate @user3:test as that membership
+                        # hasn't changed. We continue to store the existing lazy
+                        # members since they might be useful for future
+                        # requests. (Alternatively, we could invalidate all
+                        # members in the room when the client stops lazy
+                        # loading, but we opt to keep track of them).
+                        lazy_members_invalidated={"@user2:test"},
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         # `EventTypes.Member` is no longer requested but since that
                         # state hasn't changed, nothing should change (we should still
                         # keep track that we've sent `EventTypes.Member` before).
@@ -4544,13 +4575,20 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                         # We don't need to request anything more if they are requesting
                         # less state now
                         StateFilter.none(),
+                        # Previous request did not include any explicit members,
+                        # so there is no extra users to add to the lazy cache.
+                        extra_users_to_add_to_lazy_cache=frozenset(),
+                        # Nothing has been invalidated.
+                        lazy_members_invalidated=frozenset(),
                     ),
                 ),
             ),
             (
-                "state_key_retract_lazy_keep_previous_memberships_with_new_memberships",
+                "state_key_retract_lazy_keep_previous_explicit_memberships",
                 """
-                Test retracting the `required_state` to no longer lazy-loading room members.
+                Test removing explicit memberships from the `required_state`
+                when lazy-loading room members tracks previously sent
+                memberships.
                 """,
                 RequiredStateChangesTestParameters(
                     previous_required_state_map={
@@ -4560,39 +4598,144 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                             "@user3:test",
                         }
                     },
-                    request_required_state_map={EventTypes.Member: {"@user4:test"}},
+                    request_required_state_map={EventTypes.Member: {StateValues.LAZY}},
+                    previously_returned_lazy_user_ids=frozenset(),
+                    request_lazy_load_user_ids={"@user3:test"},
                     state_deltas={(EventTypes.Member, "@user2:test"): "$event_id"},
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
+                        # Since an explicit membership was removed, we record
+                        # the new required state config and move them to lazy
+                        # members.
+                        {EventTypes.Member: {StateValues.LAZY}},
+                        # We have already sent @user3 down before.
+                        #
+                        # `@user3:test` is required for lazy loading, but we've
+                        # already sent it down before (due to it being in
+                        # `previous_required_state_map`), so we don't need to
+                        # request it again.
+                        StateFilter.none(),
+                        # Remember the fact that we've sent @user3 down before,
+                        # but not @user2 as that has been invalidated.
+                        extra_users_to_add_to_lazy_cache={"@user3:test"},
+                        # Nothing to invalidate as there are no existing lazy members.
+                        lazy_members_invalidated=frozenset(),
+                    ),
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
+                        # While some explicit memberships were removed, there were no
+                        # state changes, so we don't need to persist the new required
+                        # state config yet.
+                        None,
+                        # We have already sent @user3 down before.
+                        #
+                        # `@user3:test` is required for lazy loading, but we've
+                        # already sent it down before (due to it being in
+                        # `previous_required_state_map`), so we don't need to
+                        # request it again.
+                        StateFilter.none(),
+                        # Remember the fact that we've sent the users down before.
+                        extra_users_to_add_to_lazy_cache=frozenset(),
+                        # Nothing to invalidate as there are no existing lazy members.
+                        lazy_members_invalidated=frozenset(),
+                    ),
+                ),
+            ),
+            (
+                "state_key_retract_lazy_keep_previous_explicit_me_memberships",
+                """
+                Test removing explicit $ME memberships from the `required_state`
+                when lazy-loading room members tracks previously sent
+                memberships.
+                """,
+                RequiredStateChangesTestParameters(
+                    previous_required_state_map={
+                        EventTypes.Member: {
+                            StateValues.LAZY,
+                            StateValues.ME,
+                            "@user2:test",
+                        }
+                    },
+                    request_required_state_map={EventTypes.Member: {StateValues.LAZY}},
+                    previously_returned_lazy_user_ids=frozenset(),
+                    request_lazy_load_user_ids={"@user:test"},
+                    state_deltas={(EventTypes.Member, "@user2:test"): "$event_id"},
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
+                        # Since an explicit membership was removed, we record
+                        # the new required state config and move them to lazy
+                        # members.
+                        {EventTypes.Member: {StateValues.LAZY}},
+                        # We have already sent @user down before.
+                        #
+                        # `@user:test` is required for lazy loading, but we've
+                        # already sent it down before (due to `StateValues.ME`
+                        # being in `previous_required_state_map`), so we don't
+                        # need to request it again.
+                        StateFilter.none(),
+                        # Remember the fact that we've sent @user down before,
+                        # but not @user2 as that has been invalidated.
+                        extra_users_to_add_to_lazy_cache={"@user:test"},
+                        # Nothing to invalidate as there are no existing lazy members.
+                        lazy_members_invalidated=frozenset(),
+                    ),
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
+                        # While some explicit memberships were removed, there were no
+                        # state changes, so we don't need to persist the new required
+                        # state config yet.
+                        None,
+                        # We have already sent @user down before.
+                        #
+                        # `@user:test` is required for lazy loading, but we've
+                        # already sent it down before (due to `StateValues.ME`
+                        # being in `previous_required_state_map`), so we don't
+                        # need to request it again.
+                        StateFilter.none(),
+                        # No relevant state has changed and we don't persist the
+                        # changed required_state_map, so we don't yet move the
+                        # $ME state to the lazy cache.
+                        extra_users_to_add_to_lazy_cache=frozenset(),
+                        # Nothing to invalidate as there are no existing lazy members.
+                        lazy_members_invalidated=frozenset(),
+                    ),
+                ),
+            ),
+            (
+                "state_key_retract_lazy_keep_previous_memberships_with_new_memberships",
+                """
+                Test retracting the `required_state` to no longer lazy-loading room members.
+                """,
+                RequiredStateChangesTestParameters(
+                    previous_required_state_map={EventTypes.Member: {StateValues.LAZY}},
+                    request_required_state_map={EventTypes.Member: {"@user4:test"}},
+                    previously_returned_lazy_user_ids={"@user2:test", "@user3:test"},
+                    request_lazy_load_user_ids=frozenset(),
+                    state_deltas={(EventTypes.Member, "@user2:test"): "$event_id"},
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         # Since "@user4:test" was added, we should persist the changed
                         # required state config.
-                        #
+                        {EventTypes.Member: {"@user4:test"}},
+                        # We should see the new state_keys added
+                        StateFilter.from_types([(EventTypes.Member, "@user4:test")]),
+                        # Previous request did not include any explicit members,
+                        # so there is no extra users to add to the lazy cache.
+                        extra_users_to_add_to_lazy_cache=frozenset(),
                         # Also remove "@user2:test" since that state has changed and is no
                         # longer being requested anymore. Since something was removed,
                         # we also should persist the changed to required state. That way next
                         # time, they request "@user2:test", we see that we haven't sent
                         # it before and send the new state. (we should still keep track
                         # that we've sent specific `EventTypes.Member` before)
-                        {
-                            EventTypes.Member: {
-                                "@user3:test",
-                                "@user4:test",
-                            }
-                        },
-                        # We should see the new state_keys added
-                        StateFilter.from_types([(EventTypes.Member, "@user4:test")]),
+                        lazy_members_invalidated={"@user2:test"},
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         # Since "@user4:test" was added, we should persist the changed
                         # required state config.
-                        {
-                            EventTypes.Member: {
-                                "@user2:test",
-                                "@user3:test",
-                                "@user4:test",
-                            }
-                        },
+                        {EventTypes.Member: {"@user4:test"}},
                         # We should see the new state_keys added
                         StateFilter.from_types([(EventTypes.Member, "@user4:test")]),
+                        # Previous request did not include any explicit members,
+                        # so there is no extra users to add to the lazy cache.
+                        extra_users_to_add_to_lazy_cache=frozenset(),
+                        # We don't invalidate user2 as they haven't changed
+                        lazy_members_invalidated=frozenset(),
                     ),
                 ),
             ),
@@ -4613,7 +4756,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                     # room required state config to match the request. And since we we're previously
                     # already fetching everything, we don't have to fetch anything now that they've
                     # narrowed.
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         {
                             StateValues.WILDCARD: {
                                 "state_key1",
@@ -4623,7 +4766,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                         },
                         StateFilter.none(),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         {
                             StateValues.WILDCARD: {
                                 "state_key1",
@@ -4649,11 +4792,11 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                     },
                     state_deltas={("type1", "state_key1"): "$event_id"},
                     # We've added a wildcard, so we persist the change and request everything
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         {StateValues.WILDCARD: {StateValues.WILDCARD}},
                         StateFilter.all(),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         {StateValues.WILDCARD: {StateValues.WILDCARD}},
                         StateFilter.all(),
                     ),
@@ -4673,7 +4816,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                     # request. And since we we're previously already fetching
                     # everything, we don't have to fetch anything now that they've
                     # narrowed.
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         {
                             "type1": {
                                 "state_key1",
@@ -4683,7 +4826,7 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                         },
                         StateFilter.none(),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         {
                             "type1": {
                                 "state_key1",
@@ -4708,11 +4851,11 @@ class RequiredStateChangesTestCase(unittest.TestCase):
                     # update the effective room required state config to match the
                     # request. And we need to request all of the state for that type
                     # because we previously, only sent down a few keys.
-                    expected_with_state_deltas=(
+                    expected_with_state_deltas=_RequiredStateChangesReturn(
                         {"type1": {StateValues.WILDCARD, "state_key2", "state_key3"}},
                         StateFilter.from_types([("type1", None)]),
                     ),
-                    expected_without_state_deltas=(
+                    expected_without_state_deltas=_RequiredStateChangesReturn(
                         {
                             "type1": {
                                 StateValues.WILDCARD,
@@ -4734,42 +4877,66 @@ class RequiredStateChangesTestCase(unittest.TestCase):
         test_parameters: RequiredStateChangesTestParameters,
     ) -> None:
         # Without `state_deltas`
-        changed_required_state_map, added_state_filter = _required_state_changes(
+        state_changes = _required_state_changes(
             user_id="@user:test",
             prev_required_state_map=test_parameters.previous_required_state_map,
             request_required_state_map=test_parameters.request_required_state_map,
+            previously_returned_lazy_user_ids=test_parameters.previously_returned_lazy_user_ids,
+            request_lazy_load_user_ids=test_parameters.request_lazy_load_user_ids,
             state_deltas={},
         )
 
         self.assertEqual(
-            changed_required_state_map,
-            test_parameters.expected_without_state_deltas[0],
+            state_changes.changed_required_state_map,
+            test_parameters.expected_without_state_deltas.changed_required_state_map,
             "changed_required_state_map does not match (without state_deltas)",
         )
         self.assertEqual(
-            added_state_filter,
-            test_parameters.expected_without_state_deltas[1],
+            state_changes.added_state_filter,
+            test_parameters.expected_without_state_deltas.added_state_filter,
             "added_state_filter does not match (without state_deltas)",
         )
+        self.assertEqual(
+            state_changes.lazy_members_invalidated,
+            test_parameters.expected_without_state_deltas.lazy_members_invalidated,
+            "lazy_members_invalidated does not match (without state_deltas)",
+        )
+        self.assertEqual(
+            state_changes.extra_users_to_add_to_lazy_cache,
+            test_parameters.expected_without_state_deltas.extra_users_to_add_to_lazy_cache,
+            "lazy_members_previously_returned does not match (without state_deltas)",
+        )
 
         # With `state_deltas`
-        changed_required_state_map, added_state_filter = _required_state_changes(
+        state_changes = _required_state_changes(
             user_id="@user:test",
             prev_required_state_map=test_parameters.previous_required_state_map,
             request_required_state_map=test_parameters.request_required_state_map,
+            previously_returned_lazy_user_ids=test_parameters.previously_returned_lazy_user_ids,
+            request_lazy_load_user_ids=test_parameters.request_lazy_load_user_ids,
             state_deltas=test_parameters.state_deltas,
         )
 
         self.assertEqual(
-            changed_required_state_map,
-            test_parameters.expected_with_state_deltas[0],
+            state_changes.changed_required_state_map,
+            test_parameters.expected_with_state_deltas.changed_required_state_map,
             "changed_required_state_map does not match (with state_deltas)",
         )
         self.assertEqual(
-            added_state_filter,
-            test_parameters.expected_with_state_deltas[1],
+            state_changes.added_state_filter,
+            test_parameters.expected_with_state_deltas.added_state_filter,
             "added_state_filter does not match (with state_deltas)",
         )
+        self.assertEqual(
+            state_changes.lazy_members_invalidated,
+            test_parameters.expected_with_state_deltas.lazy_members_invalidated,
+            "lazy_members_invalidated does not match (with state_deltas)",
+        )
+        self.assertEqual(
+            state_changes.extra_users_to_add_to_lazy_cache,
+            test_parameters.expected_with_state_deltas.extra_users_to_add_to_lazy_cache,
+            "lazy_members_previously_returned does not match (with state_deltas)",
+        )
 
     @parameterized.expand(
         [
@@ -4805,12 +4972,16 @@ class RequiredStateChangesTestCase(unittest.TestCase):
         }
 
         # (function under test)
-        changed_required_state_map, added_state_filter = _required_state_changes(
+        state_changes = _required_state_changes(
             user_id="@user:test",
             prev_required_state_map=previous_required_state_map,
             request_required_state_map=request_required_state_map,
+            previously_returned_lazy_user_ids=frozenset(),
+            request_lazy_load_user_ids=frozenset(),
             state_deltas={},
         )
+        changed_required_state_map = state_changes.changed_required_state_map
+
         assert changed_required_state_map is not None
 
         # We should only remember up to the maximum number of state keys
@@ -4874,12 +5045,16 @@ class RequiredStateChangesTestCase(unittest.TestCase):
         )
 
         # (function under test)
-        changed_required_state_map, added_state_filter = _required_state_changes(
+        state_changes = _required_state_changes(
             user_id="@user:test",
             prev_required_state_map=previous_required_state_map,
             request_required_state_map=request_required_state_map,
+            previously_returned_lazy_user_ids=frozenset(),
+            request_lazy_load_user_ids=frozenset(),
             state_deltas={},
         )
+        changed_required_state_map = state_changes.changed_required_state_map
+
         assert changed_required_state_map is not None
 
         # Should include all of the requested state

tests/http/test_site.py

@@ -22,6 +22,7 @@
 from twisted.internet.address import IPv6Address
 from twisted.internet.testing import MemoryReactor, StringTransport
 
+from synapse.app._base import max_request_body_size
 from synapse.app.homeserver import SynapseHomeServer
 from synapse.server import HomeServer
 from synapse.util.clock import Clock
@@ -143,3 +144,104 @@ class SynapseRequestTestCase(HomeserverTestCase):
 
         # we should get a 415
         self.assertRegex(transport.value().decode(), r"^HTTP/1\.1 415 ")
+
+    def test_content_length_too_large(self) -> None:
+        """HTTP requests with Content-Length exceeding max size should be rejected with 413"""
+        self.hs.start_listening()
+
+        # find the HTTP server which is configured to listen on port 0
+        (port, factory, _backlog, interface) = self.reactor.tcpServers[0]
+        self.assertEqual(interface, "::")
+        self.assertEqual(port, 0)
+
+        # complete the connection and wire it up to a fake transport
+        client_address = IPv6Address("TCP", "::1", 2345)
+        protocol = factory.buildProtocol(client_address)
+        transport = StringTransport()
+        protocol.makeConnection(transport)
+
+        # Send a request with Content-Length header that exceeds the limit.
+        # Default max is 50MB (from media max_upload_size), so send something larger.
+        oversized_length = 1 + max_request_body_size(self.hs.config)
+        protocol.dataReceived(
+            b"POST / HTTP/1.1\r\n"
+            b"Connection: close\r\n"
+            b"Content-Length: " + str(oversized_length).encode() + b"\r\n"
+            b"\r\n"
+            b"" + b"x" * oversized_length + b"\r\n"
+            b"\r\n"
+        )
+
+        # Advance the reactor to process the request
+        while not transport.disconnecting:
+            self.reactor.advance(1)
+
+        # We should get a 413 Content Too Large
+        response = transport.value().decode()
+        self.assertRegex(response, r"^HTTP/1\.1 413 ")
+        self.assertSubstring("M_TOO_LARGE", response)
+
+    def test_too_many_content_length_headers(self) -> None:
+        """HTTP requests with multiple Content-Length headers should be rejected with 400"""
+        self.hs.start_listening()
+
+        # find the HTTP server which is configured to listen on port 0
+        (port, factory, _backlog, interface) = self.reactor.tcpServers[0]
+        self.assertEqual(interface, "::")
+        self.assertEqual(port, 0)
+
+        # complete the connection and wire it up to a fake transport
+        client_address = IPv6Address("TCP", "::1", 2345)
+        protocol = factory.buildProtocol(client_address)
+        transport = StringTransport()
+        protocol.makeConnection(transport)
+
+        protocol.dataReceived(
+            b"POST / HTTP/1.1\r\n"
+            b"Connection: close\r\n"
+            b"Content-Length: " + str(5).encode() + b"\r\n"
+            b"Content-Length: " + str(5).encode() + b"\r\n"
+            b"\r\n"
+            b"" + b"xxxxx" + b"\r\n"
+            b"\r\n"
+        )
+
+        # Advance the reactor to process the request
+        while not transport.disconnecting:
+            self.reactor.advance(1)
+
+        # We should get a 400
+        response = transport.value().decode()
+        self.assertRegex(response, r"^HTTP/1\.1 400 ")
+
+    def test_invalid_content_length_headers(self) -> None:
+        """HTTP requests with invalid Content-Length header should be rejected with 400"""
+        self.hs.start_listening()
+
+        # find the HTTP server which is configured to listen on port 0
+        (port, factory, _backlog, interface) = self.reactor.tcpServers[0]
+        self.assertEqual(interface, "::")
+        self.assertEqual(port, 0)
+
+        # complete the connection and wire it up to a fake transport
+        client_address = IPv6Address("TCP", "::1", 2345)
+        protocol = factory.buildProtocol(client_address)
+        transport = StringTransport()
+        protocol.makeConnection(transport)
+
+        protocol.dataReceived(
+            b"POST / HTTP/1.1\r\n"
+            b"Connection: close\r\n"
+            b"Content-Length: eight\r\n"
+            b"\r\n"
+            b"" + b"xxxxx" + b"\r\n"
+            b"\r\n"
+        )
+
+        # Advance the reactor to process the request
+        while not transport.disconnecting:
+            self.reactor.advance(1)
+
+        # We should get a 400
+        response = transport.value().decode()
+        self.assertRegex(response, r"^HTTP/1\.1 400 ")

tests/rest/admin/test_device.py

@@ -26,7 +26,7 @@ from twisted.internet.testing import MemoryReactor
 
 import synapse.rest.admin
 from synapse.api.errors import Codes
-from synapse.handlers.device import DeviceWriterHandler
+from synapse.handlers.device import MAX_DEVICE_DISPLAY_NAME_LEN, DeviceWriterHandler
 from synapse.rest.client import devices, login
 from synapse.server import HomeServer
 from synapse.util.clock import Clock
@@ -175,10 +175,7 @@ class DeviceRestTestCase(unittest.HomeserverTestCase):
         )
 
         # Request to update a device display name with a new value that is longer than allowed.
-        update = {
-            "display_name": "a"
-            * (synapse.handlers.device.MAX_DEVICE_DISPLAY_NAME_LEN + 1)
-        }
+        update = {"display_name": "a" * (MAX_DEVICE_DISPLAY_NAME_LEN + 1)}
 
         channel = self.make_request(
             "PUT",

tests/rest/admin/test_media.py

@@ -756,6 +756,112 @@ class DeleteMediaByDateSizeTestCase(_AdminMediaTests):
             self.assertFalse(os.path.exists(local_path))
 
 
+class ListQuarantinedMediaTestCase(_AdminMediaTests):
+    def prepare(self, reactor: MemoryReactor, clock: Clock, hs: HomeServer) -> None:
+        self.store = hs.get_datastores().main
+        self.server_name = hs.hostname
+
+    @parameterized.expand(["local", "remote"])
+    def test_no_auth(self, kind: str) -> None:
+        """
+        Try to list quarantined media without authentication.
+        """
+
+        channel = self.make_request(
+            "GET",
+            "/_synapse/admin/v1/media/quarantined?kind=%s" % (kind,),
+        )
+
+        self.assertEqual(401, channel.code, msg=channel.json_body)
+        self.assertEqual(Codes.MISSING_TOKEN, channel.json_body["errcode"])
+
+    @parameterized.expand(["local", "remote"])
+    def test_requester_is_not_admin(self, kind: str) -> None:
+        """
+        If the user is not a server admin, an error is returned.
+        """
+        self.other_user = self.register_user("user", "pass")
+        self.other_user_token = self.login("user", "pass")
+
+        channel = self.make_request(
+            "GET",
+            "/_synapse/admin/v1/media/quarantined?kind=%s" % (kind,),
+            access_token=self.other_user_token,
+        )
+
+        self.assertEqual(403, channel.code, msg=channel.json_body)
+        self.assertEqual(Codes.FORBIDDEN, channel.json_body["errcode"])
+
+    def test_list_quarantined_media(self) -> None:
+        """
+        Ensure we actually get results for each page. We can't really test that
+        remote media is quarantined, but we can test that local media is.
+        """
+        self.admin_user = self.register_user("admin", "pass", admin=True)
+        self.admin_user_tok = self.login("admin", "pass")
+
+        def _upload() -> str:
+            return self.helper.upload_media(
+                SMALL_PNG, tok=self.admin_user_tok, expect_code=200
+            )["content_uri"][6:].split("/")[1]  # Cut off 'mxc://' and domain
+
+        self.media_id_1 = _upload()
+        self.media_id_2 = _upload()
+        self.media_id_3 = _upload()
+
+        def _quarantine(media_id: str) -> None:
+            channel = self.make_request(
+                "POST",
+                "/_synapse/admin/v1/media/quarantine/%s/%s"
+                % (
+                    self.server_name,
+                    media_id,
+                ),
+                access_token=self.admin_user_tok,
+            )
+            self.assertEqual(200, channel.code, msg=channel.json_body)
+
+        _quarantine(self.media_id_1)
+        _quarantine(self.media_id_2)
+        _quarantine(self.media_id_3)
+
+        # Page 1
+        channel = self.make_request(
+            "GET",
+            "/_synapse/admin/v1/media/quarantined?kind=local&from=0&limit=1",
+            access_token=self.admin_user_tok,
+        )
+        self.assertEqual(200, channel.code, msg=channel.json_body)
+        self.assertEqual(1, len(channel.json_body["media"]))
+
+        # Page 2
+        channel = self.make_request(
+            "GET",
+            "/_synapse/admin/v1/media/quarantined?kind=local&from=1&limit=1",
+            access_token=self.admin_user_tok,
+        )
+        self.assertEqual(200, channel.code, msg=channel.json_body)
+        self.assertEqual(1, len(channel.json_body["media"]))
+
+        # Page 3
+        channel = self.make_request(
+            "GET",
+            "/_synapse/admin/v1/media/quarantined?kind=local&from=2&limit=1",
+            access_token=self.admin_user_tok,
+        )
+        self.assertEqual(200, channel.code, msg=channel.json_body)
+        self.assertEqual(1, len(channel.json_body["media"]))
+
+        # Page 4 (no media)
+        channel = self.make_request(
+            "GET",
+            "/_synapse/admin/v1/media/quarantined?kind=local&from=3&limit=1",
+            access_token=self.admin_user_tok,
+        )
+        self.assertEqual(200, channel.code, msg=channel.json_body)
+        self.assertEqual(0, len(channel.json_body["media"]))
+
+
 class QuarantineMediaByIDTestCase(_AdminMediaTests):
     def upload_media_and_return_media_id(self, data: bytes) -> str:
         # Upload some media into the room

tests/rest/admin/test_room.py

@@ -2976,6 +2976,120 @@ class JoinAliasRoomTestCase(unittest.HomeserverTestCase):
         self.assertEqual(200, channel.code, msg=channel.json_body)
         self.assertEqual(private_room_id, channel.json_body["joined_rooms"][0])
 
+    def test_joined_rooms(self) -> None:
+        """
+        Test joined_rooms admin endpoint.
+        """
+
+        channel = self.make_request(
+            "POST",
+            f"/_matrix/client/v3/join/{self.public_room_id}",
+            content={"user_id": self.second_user_id},
+            access_token=self.second_tok,
+        )
+
+        self.assertEqual(200, channel.code, msg=channel.json_body)
+        self.assertEqual(self.public_room_id, channel.json_body["room_id"])
+
+        channel = self.make_request(
+            "GET",
+            f"/_synapse/admin/v1/users/{self.second_user_id}/joined_rooms",
+            access_token=self.admin_user_tok,
+        )
+        self.assertEqual(200, channel.code, msg=channel.json_body)
+        self.assertEqual(self.public_room_id, channel.json_body["joined_rooms"][0])
+
+    def test_memberships(self) -> None:
+        """
+        Test user memberships admin endpoint.
+        """
+
+        channel = self.make_request(
+            "POST",
+            f"/_matrix/client/v3/join/{self.public_room_id}",
+            content={"user_id": self.second_user_id},
+            access_token=self.second_tok,
+        )
+        self.assertEqual(200, channel.code, msg=channel.json_body)
+
+        other_room_id = self.helper.create_room_as(
+            self.admin_user, tok=self.admin_user_tok
+        )
+
+        channel = self.make_request(
+            "POST",
+            f"/_matrix/client/v3/join/{other_room_id}",
+            content={"user_id": self.second_user_id},
+            access_token=self.second_tok,
+        )
+        self.assertEqual(200, channel.code, msg=channel.json_body)
+
+        channel = self.make_request(
+            "GET",
+            f"/_synapse/admin/v1/users/{self.second_user_id}/memberships",
+            access_token=self.admin_user_tok,
+        )
+
+        self.assertEqual(200, channel.code, msg=channel.json_body)
+        self.assertEqual(
+            {
+                "memberships": {
+                    self.public_room_id: Membership.JOIN,
+                    other_room_id: Membership.JOIN,
+                }
+            },
+            channel.json_body,
+        )
+
+        channel = self.make_request(
+            "POST",
+            f"/_matrix/client/v3/rooms/{other_room_id}/leave",
+            content={"user_id": self.second_user_id},
+            access_token=self.second_tok,
+        )
+        self.assertEqual(200, channel.code, msg=channel.json_body)
+
+        invited_room_id = self.helper.create_room_as(
+            self.admin_user, tok=self.admin_user_tok
+        )
+        channel = self.make_request(
+            "POST",
+            f"/_matrix/client/v3/rooms/{invited_room_id}/invite",
+            content={"user_id": self.second_user_id},
+            access_token=self.admin_user_tok,
+        )
+        self.assertEqual(200, channel.code, msg=channel.json_body)
+
+        banned_room_id = self.helper.create_room_as(
+            self.admin_user, tok=self.admin_user_tok
+        )
+        channel = self.make_request(
+            "POST",
+            f"/_matrix/client/v3/rooms/{banned_room_id}/ban",
+            content={"user_id": self.second_user_id},
+            access_token=self.admin_user_tok,
+        )
+        self.assertEqual(200, channel.code, msg=channel.json_body)
+
+        channel = self.make_request(
+            "GET",
+            f"/_synapse/admin/v1/users/{self.second_user_id}/memberships",
+            access_token=self.admin_user_tok,
+        )
+
+        self.assertEqual(200, channel.code, msg=channel.json_body)
+        self.assertEqual(
+            {
+                "memberships": {
+                    self.public_room_id: Membership.JOIN,
+                    other_room_id: Membership.LEAVE,
+                    invited_room_id: Membership.INVITE,
+                    banned_room_id: Membership.BAN,
+                }
+            },
+            channel.json_body,
+        )
+
     def test_context_as_non_admin(self) -> None:
         """
         Test that, without being admin, one cannot use the context admin API

tests/rest/client/sliding_sync/test_lists_filters.py

@@ -690,7 +690,7 @@ class SlidingSyncFiltersTestCase(SlidingSyncBase):
         user1_tok = self.login(user1_id, "pass")
 
         # Create a remote invite room without any `unsigned.invite_room_state`
-        _remote_invite_room_id = self._create_remote_invite_room_for_user(
+        _remote_invite_room_id, _ = self._create_remote_invite_room_for_user(
             user1_id, None
         )
 
@@ -760,7 +760,7 @@ class SlidingSyncFiltersTestCase(SlidingSyncBase):
 
         # Create a remote invite room with some `unsigned.invite_room_state`
         # indicating that the room is encrypted.
-        remote_invite_room_id = self._create_remote_invite_room_for_user(
+        remote_invite_room_id, _ = self._create_remote_invite_room_for_user(
             user1_id,
             [
                 StrippedStateEvent(
@@ -849,7 +849,7 @@ class SlidingSyncFiltersTestCase(SlidingSyncBase):
 
         # Create a remote invite room with some `unsigned.invite_room_state`
         # but don't set any room encryption event.
-        remote_invite_room_id = self._create_remote_invite_room_for_user(
+        remote_invite_room_id, _ = self._create_remote_invite_room_for_user(
             user1_id,
             [
                 StrippedStateEvent(
@@ -1484,7 +1484,7 @@ class SlidingSyncFiltersTestCase(SlidingSyncBase):
         user1_tok = self.login(user1_id, "pass")
 
         # Create a remote invite room without any `unsigned.invite_room_state`
-        _remote_invite_room_id = self._create_remote_invite_room_for_user(
+        _remote_invite_room_id, _ = self._create_remote_invite_room_for_user(
             user1_id, None
         )
 
@@ -1554,7 +1554,7 @@ class SlidingSyncFiltersTestCase(SlidingSyncBase):
 
         # Create a remote invite room with some `unsigned.invite_room_state` indicating
         # that it is a space room
-        remote_invite_room_id = self._create_remote_invite_room_for_user(
+        remote_invite_room_id, _ = self._create_remote_invite_room_for_user(
             user1_id,
             [
                 StrippedStateEvent(
@@ -1637,7 +1637,7 @@ class SlidingSyncFiltersTestCase(SlidingSyncBase):
 
         # Create a remote invite room with some `unsigned.invite_room_state`
         # but the create event does not specify a room type (normal room)
-        remote_invite_room_id = self._create_remote_invite_room_for_user(
+        remote_invite_room_id, _ = self._create_remote_invite_room_for_user(
             user1_id,
             [
                 StrippedStateEvent(

tests/rest/client/sliding_sync/test_rooms_required_state.py

@@ -23,6 +23,7 @@ from synapse.api.constants import EventContentFields, EventTypes, JoinRules, Mem
 from synapse.handlers.sliding_sync import StateValues
 from synapse.rest.client import knock, login, room, sync
 from synapse.server import HomeServer
+from synapse.storage.databases.main.events import DeltaState, SlidingSyncTableChanges
 from synapse.util.clock import Clock
 
 from tests.rest.client.sliding_sync.test_sliding_sync import SlidingSyncBase
@@ -642,11 +643,6 @@ class SlidingSyncRoomsRequiredStateTestCase(SlidingSyncBase):
         self._assertRequiredStateIncludes(
             response_body["rooms"][room_id1]["required_state"],
             {
-                # This appears because *some* membership in the room changed and the
-                # heroes are recalculated and is thrown in because we have it. But this
-                # is technically optional and not needed because we've already seen user2
-                # in the last sync (and their membership hasn't changed).
-                state_map[(EventTypes.Member, user2_id)],
                 # Appears because there is a message in the timeline from this user
                 state_map[(EventTypes.Member, user4_id)],
                 # Appears because there is a membership event in the timeline from this user
@@ -841,6 +837,437 @@ class SlidingSyncRoomsRequiredStateTestCase(SlidingSyncBase):
             exact=True,
         )
 
+    def test_lazy_loading_room_members_limited_sync(self) -> None:
+        """Test that when using lazy loading for room members and a limited sync
+        missing a membership change, we include the membership change next time
+        said user says something.
+        """
+
+        user1_id = self.register_user("user1", "pass")
+        user1_tok = self.login(user1_id, "pass")
+        user2_id = self.register_user("user2", "pass")
+        user2_tok = self.login(user2_id, "pass")
+
+        room_id1 = self.helper.create_room_as(user2_id, tok=user2_tok)
+        self.helper.join(room_id1, user1_id, tok=user1_tok)
+
+        # Send a message from each user to the room so that both memberships are sent down.
+        self.helper.send(room_id1, "1", tok=user1_tok)
+        self.helper.send(room_id1, "2", tok=user2_tok)
+
+        # Make a first sync with lazy loading for the room members to establish
+        # a position
+        sync_body = {
+            "lists": {
+                "foo-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [
+                        [EventTypes.Member, StateValues.LAZY],
+                    ],
+                    "timeline_limit": 2,
+                }
+            }
+        }
+        response_body, from_token = self.do_sync(sync_body, tok=user1_tok)
+
+        # We should see both membership events in required_state
+        state_map = self.get_success(
+            self.storage_controllers.state.get_current_state(room_id1)
+        )
+        self._assertRequiredStateIncludes(
+            response_body["rooms"][room_id1]["required_state"],
+            {
+                state_map[(EventTypes.Member, user1_id)],
+                state_map[(EventTypes.Member, user2_id)],
+            },
+            exact=True,
+        )
+
+        # User2 changes their display name (causing a membership change)
+        self.helper.send_state(
+            room_id1,
+            event_type=EventTypes.Member,
+            state_key=user2_id,
+            body={
+                EventContentFields.MEMBERSHIP: Membership.JOIN,
+                EventContentFields.MEMBERSHIP_DISPLAYNAME: "New Name",
+            },
+            tok=user2_tok,
+        )
+
+        # Send a couple of messages to the room to push out the membership change
+        self.helper.send(room_id1, "3", tok=user1_tok)
+        self.helper.send(room_id1, "4", tok=user1_tok)
+
+        # Make an incremental Sliding Sync request
+        response_body, from_token = self.do_sync(
+            sync_body, since=from_token, tok=user1_tok
+        )
+
+        # The membership change should *not* be included yet as user2 doesn't
+        # have any events in the timeline.
+        self._assertRequiredStateIncludes(
+            response_body["rooms"][room_id1].get("required_state", []),
+            set(),
+            exact=True,
+        )
+
+        # Now user2 sends a message to the room
+        self.helper.send(room_id1, "5", tok=user2_tok)
+
+        # Make another incremental Sliding Sync request
+        response_body, from_token = self.do_sync(
+            sync_body, since=from_token, tok=user1_tok
+        )
+
+        # The membership change should now be included as user2 has an event
+        # in the timeline.
+        state_map = self.get_success(
+            self.storage_controllers.state.get_current_state(room_id1)
+        )
+        self._assertRequiredStateIncludes(
+            response_body["rooms"][room_id1].get("required_state", []),
+            {
+                state_map[(EventTypes.Member, user2_id)],
+            },
+            exact=True,
+        )
+
+    def test_lazy_loading_room_members_across_multiple_rooms(self) -> None:
+        """Test that lazy loading room members are tracked per-room correctly."""
+
+        user1_id = self.register_user("user1", "pass")
+        user1_tok = self.login(user1_id, "pass")
+        user2_id = self.register_user("user2", "pass")
+        user2_tok = self.login(user2_id, "pass")
+
+        # Create two rooms with both users in them and send a message in each
+        room_id1 = self.helper.create_room_as(user2_id, tok=user2_tok)
+        self.helper.join(room_id1, user1_id, tok=user1_tok)
+        self.helper.send(room_id1, "room1-msg1", tok=user2_tok)
+
+        room_id2 = self.helper.create_room_as(user2_id, tok=user2_tok)
+        self.helper.join(room_id2, user1_id, tok=user1_tok)
+        self.helper.send(room_id2, "room2-msg1", tok=user2_tok)
+
+        # Make a sync with lazy loading for the room members to establish
+        # a position
+        sync_body = {
+            "lists": {
+                "foo-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [
+                        [EventTypes.Member, StateValues.LAZY],
+                    ],
+                    "timeline_limit": 1,
+                }
+            }
+        }
+        response_body, from_token = self.do_sync(sync_body, tok=user1_tok)
+
+        # We expect to see only user2's membership in both rooms
+        state_map = self.get_success(
+            self.storage_controllers.state.get_current_state(room_id1)
+        )
+        self._assertRequiredStateIncludes(
+            response_body["rooms"][room_id1]["required_state"],
+            {
+                state_map[(EventTypes.Member, user2_id)],
+            },
+            exact=True,
+        )
+
+        # Send a message in room1 from user1
+        self.helper.send(room_id1, "room1-msg2", tok=user1_tok)
+
+        # Make an incremental Sliding Sync request and check that we get user1's
+        # membership.
+        response_body, from_token = self.do_sync(
+            sync_body, since=from_token, tok=user1_tok
+        )
+
+        state_map = self.get_success(
+            self.storage_controllers.state.get_current_state(room_id1)
+        )
+        self._assertRequiredStateIncludes(
+            response_body["rooms"][room_id1]["required_state"],
+            {
+                state_map[(EventTypes.Member, user1_id)],
+            },
+            exact=True,
+        )
+
+        # Send a message in room2 from user1
+        self.helper.send(room_id2, "room2-msg2", tok=user1_tok)
+
+        # Make an incremental Sliding Sync request and check that we get user1's
+        # membership.
+        response_body, from_token = self.do_sync(
+            sync_body, since=from_token, tok=user1_tok
+        )
+        state_map = self.get_success(
+            self.storage_controllers.state.get_current_state(room_id2)
+        )
+        self._assertRequiredStateIncludes(
+            response_body["rooms"][room_id2]["required_state"],
+            {
+                state_map[(EventTypes.Member, user1_id)],
+            },
+            exact=True,
+        )
+
+    def test_lazy_loading_room_members_across_multiple_connections(self) -> None:
+        """Test that lazy loading room members are tracked per-connection
+        correctly.
+
+        This catches bugs where if a membership got sent down one connection,
+        it would incorrectly assume it was sent down another connection.
+        """
+
+        user1_id = self.register_user("user1", "pass")
+        user1_tok = self.login(user1_id, "pass")
+        user2_id = self.register_user("user2", "pass")
+        user2_tok = self.login(user2_id, "pass")
+
+        room_id1 = self.helper.create_room_as(user2_id, tok=user2_tok)
+        self.helper.join(room_id1, user1_id, tok=user1_tok)
+
+        self.helper.send(room_id1, "1", tok=user2_tok)
+
+        # Make a sync with lazy loading for the room members to establish
+        # a position
+        sync_body1 = {
+            "conn_id": "first-connection",
+            "lists": {
+                "foo-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [
+                        [EventTypes.Member, StateValues.LAZY],
+                    ],
+                    "timeline_limit": 1,
+                }
+            },
+        }
+        response_body, from_token1 = self.do_sync(sync_body1, tok=user1_tok)
+
+        # We expect to see only user2's membership in the room
+        state_map = self.get_success(
+            self.storage_controllers.state.get_current_state(room_id1)
+        )
+        self._assertRequiredStateIncludes(
+            response_body["rooms"][room_id1]["required_state"],
+            {
+                state_map[(EventTypes.Member, user2_id)],
+            },
+            exact=True,
+        )
+
+        # Now make a new connection
+        sync_body2 = {
+            "conn_id": "second-connection",
+            "lists": {
+                "foo-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [
+                        [EventTypes.Member, StateValues.LAZY],
+                    ],
+                    "timeline_limit": 1,
+                }
+            },
+        }
+        response_body, from_token2 = self.do_sync(sync_body2, tok=user1_tok)
+
+        # We should see user2's membership as this is a new connection
+        self._assertRequiredStateIncludes(
+            response_body["rooms"][room_id1]["required_state"],
+            {
+                state_map[(EventTypes.Member, user2_id)],
+            },
+            exact=True,
+        )
+
+        # If we send a message from user1 and sync again on the first connection,
+        # we should get user1's membership
+        self.helper.send(room_id1, "2", tok=user1_tok)
+        response_body, from_token1 = self.do_sync(
+            sync_body1, since=from_token1, tok=user1_tok
+        )
+        self._assertRequiredStateIncludes(
+            response_body["rooms"][room_id1]["required_state"],
+            {
+                state_map[(EventTypes.Member, user1_id)],
+            },
+            exact=True,
+        )
+
+        # We sync again on the first connection to "ack" the position. This
+        # triggers the `sliding_sync_connection_lazy_members` to set its
+        # connection_position to null.
+        self.do_sync(sync_body1, since=from_token1, tok=user1_tok)
+
+        # If we sync again on the second connection, we should also get user1's
+        # membership
+        response_body, _ = self.do_sync(sync_body2, since=from_token2, tok=user1_tok)
+        self._assertRequiredStateIncludes(
+            response_body["rooms"][room_id1]["required_state"],
+            {
+                state_map[(EventTypes.Member, user1_id)],
+            },
+            exact=True,
+        )
+
+    def test_lazy_loading_room_members_forked_position(self) -> None:
+        """Test that lazy loading room members are tracked correctly when a
+        connection position is reused"""
+
+        user1_id = self.register_user("user1", "pass")
+        user1_tok = self.login(user1_id, "pass")
+        user2_id = self.register_user("user2", "pass")
+        user2_tok = self.login(user2_id, "pass")
+
+        room_id1 = self.helper.create_room_as(user2_id, tok=user2_tok)
+        self.helper.join(room_id1, user1_id, tok=user1_tok)
+
+        self.helper.send(room_id1, "1", tok=user2_tok)
+
+        # Make a sync with lazy loading for the room members to establish
+        # a position
+        sync_body = {
+            "lists": {
+                "foo-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [
+                        [EventTypes.Member, StateValues.LAZY],
+                    ],
+                    "timeline_limit": 1,
+                }
+            }
+        }
+        response_body, from_token = self.do_sync(sync_body, tok=user1_tok)
+
+        # We expect to see only user2's membership in the room
+        state_map = self.get_success(
+            self.storage_controllers.state.get_current_state(room_id1)
+        )
+        self._assertRequiredStateIncludes(
+            response_body["rooms"][room_id1]["required_state"],
+            {
+                state_map[(EventTypes.Member, user2_id)],
+            },
+            exact=True,
+        )
+
+        # Send a message in room1 from user1
+        self.helper.send(room_id1, "2", tok=user1_tok)
+
+        # Make an incremental Sliding Sync request and check that we get user1's
+        # membership.
+        response_body, _ = self.do_sync(sync_body, since=from_token, tok=user1_tok)
+        state_map = self.get_success(
+            self.storage_controllers.state.get_current_state(room_id1)
+        )
+        self._assertRequiredStateIncludes(
+            response_body["rooms"][room_id1]["required_state"],
+            {
+                state_map[(EventTypes.Member, user1_id)],
+            },
+            exact=True,
+        )
+
+        # Now, reuse the original position and check we still get user1's
+        # membership.
+        response_body, _ = self.do_sync(sync_body, since=from_token, tok=user1_tok)
+        state_map = self.get_success(
+            self.storage_controllers.state.get_current_state(room_id1)
+        )
+        self._assertRequiredStateIncludes(
+            response_body["rooms"][room_id1]["required_state"],
+            {
+                state_map[(EventTypes.Member, user1_id)],
+            },
+            exact=True,
+        )
+
+    def test_lazy_loading_room_members_explicit_membership_removed(self) -> None:
+        """Test the case where we requested explicit memberships and then later
+        changed to lazy loading."""
+
+        user1_id = self.register_user("user1", "pass")
+        user1_tok = self.login(user1_id, "pass")
+        user2_id = self.register_user("user2", "pass")
+        user2_tok = self.login(user2_id, "pass")
+
+        room_id1 = self.helper.create_room_as(user2_id, tok=user2_tok)
+        self.helper.join(room_id1, user1_id, tok=user1_tok)
+
+        self.helper.send(room_id1, "1", tok=user2_tok)
+
+        # Make a sync with lazy loading for the room members to establish
+        # a position
+        sync_body = {
+            "lists": {
+                "foo-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [
+                        [EventTypes.Member, StateValues.ME],
+                    ],
+                    "timeline_limit": 1,
+                }
+            }
+        }
+        response_body, from_token = self.do_sync(sync_body, tok=user1_tok)
+
+        # We expect to see only user1's membership in the room
+        state_map = self.get_success(
+            self.storage_controllers.state.get_current_state(room_id1)
+        )
+        self._assertRequiredStateIncludes(
+            response_body["rooms"][room_id1]["required_state"],
+            {
+                state_map[(EventTypes.Member, user1_id)],
+            },
+            exact=True,
+        )
+
+        # Now change to lazy loading...
+        sync_body["lists"]["foo-list"]["required_state"] = [
+            [EventTypes.Member, StateValues.LAZY],
+        ]
+
+        # Send a message in room1 from user2
+        self.helper.send(room_id1, "2", tok=user2_tok)
+        response_body, from_token = self.do_sync(
+            sync_body, since=from_token, tok=user1_tok
+        )
+
+        # We should see user2's membership as it's in the timeline
+        state_map = self.get_success(
+            self.storage_controllers.state.get_current_state(room_id1)
+        )
+        self._assertRequiredStateIncludes(
+            response_body["rooms"][room_id1]["required_state"],
+            {
+                state_map[(EventTypes.Member, user2_id)],
+            },
+            exact=True,
+        )
+
+        # Now send a message in room1 from user1
+        self.helper.send(room_id1, "3", tok=user1_tok)
+
+        response_body, _ = self.do_sync(sync_body, since=from_token, tok=user1_tok)
+
+        # We should not see any memberships as we've already seen user1's
+        # membership.
+        state_map = self.get_success(
+            self.storage_controllers.state.get_current_state(room_id1)
+        )
+        self._assertRequiredStateIncludes(
+            response_body["rooms"][room_id1].get("required_state", []),
+            [],
+            exact=True,
+        )
+
     def test_rooms_required_state_me(self) -> None:
         """
         Test `rooms.required_state` correctly handles $ME.
@@ -1686,3 +2113,135 @@ class SlidingSyncRoomsRequiredStateTestCase(SlidingSyncBase):
         # We should not see the room name again, as we have already sent that
         # down.
         self.assertIsNone(response_body["rooms"][room_id1].get("required_state"))
+
+    def test_lazy_loading_room_members_state_reset_non_limited_timeline(self) -> None:
+        """Test that when using lazy-loaded members, if a membership state is
+        reset to a previous state and the sync is not limited, then we send down
+        the state reset.
+
+        Regression test as previously we only returned membership relevant to
+        the timeline and so did not tell clients about state resets for
+        users who did not send any timeline events.
+        """
+
+        user1_id = self.register_user("user1", "pass")
+        user1_tok = self.login(user1_id, "pass")
+        user2_id = self.register_user("user2", "pass")
+        user2_tok = self.login(user2_id, "pass")
+
+        room_id = self.helper.create_room_as(user2_id, tok=user2_tok, is_public=True)
+        content = self.helper.join(room_id, user1_id, tok=user1_tok)
+        first_event_id = content["event_id"]
+
+        # Send a message so that the user1 membership comes down sync (because we're lazy-loading room members)
+        self.helper.send(room_id, "msg", tok=user1_tok)
+
+        sync_body = {
+            "lists": {
+                "foo-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [
+                        [EventTypes.Member, StateValues.LAZY],
+                    ],
+                    "timeline_limit": 1,
+                }
+            }
+        }
+        response_body, from_token = self.do_sync(sync_body, tok=user1_tok)
+
+        # Check that user1 is returned
+        state_map = self.get_success(
+            self.storage_controllers.state.get_current_state(room_id)
+        )
+        self._assertRequiredStateIncludes(
+            response_body["rooms"][room_id]["required_state"],
+            {
+                state_map[(EventTypes.Member, user1_id)],
+            },
+            exact=True,
+        )
+
+        # user1 changes their display name
+        content = self.helper.send_state(
+            room_id,
+            EventTypes.Member,
+            body={"membership": "join", "displayname": "New display name"},
+            state_key=user1_id,
+            tok=user1_tok,
+        )
+        second_event_id = content["event_id"]
+
+        response_body, from_token = self.do_sync(
+            sync_body, since=from_token, tok=user1_tok
+        )
+
+        # We should see the updated membership state
+        state_map = self.get_success(
+            self.storage_controllers.state.get_current_state(room_id)
+        )
+        self._assertRequiredStateIncludes(
+            response_body["rooms"][room_id]["required_state"],
+            {
+                state_map[(EventTypes.Member, user1_id)],
+            },
+            exact=True,
+        )
+        self.assertEqual(
+            response_body["rooms"][room_id]["required_state"][0]["event_id"],
+            second_event_id,
+        )
+
+        # Now, fake a reset the membership state to the first event
+        persist_event_store = self.hs.get_datastores().persist_events
+        assert persist_event_store is not None
+
+        self.get_success(
+            persist_event_store.update_current_state(
+                room_id,
+                DeltaState(
+                    to_insert={(EventTypes.Member, user1_id): first_event_id},
+                    to_delete=[],
+                ),
+                # We don't need to worry about sliding sync changes for this test
+                SlidingSyncTableChanges(
+                    room_id=room_id,
+                    joined_room_bump_stamp_to_fully_insert=None,
+                    joined_room_updates={},
+                    membership_snapshot_shared_insert_values={},
+                    to_insert_membership_snapshots=[],
+                    to_delete_membership_snapshots=[],
+                ),
+            )
+        )
+
+        # Send a message from *user2* so that user1 wouldn't normally get
+        # synced.
+        self.helper.send(room_id, "msg2", tok=user2_tok)
+
+        response_body, from_token = self.do_sync(
+            sync_body, since=from_token, tok=user1_tok
+        )
+
+        # This should be a non-limited sync as there is only one timeline event
+        # (<= `timeline_limit). This is important as we're specifically testing the non-`limited`
+        # timeline scenario. And for reference, we don't send down state resets
+        # on limited timelines when using lazy loaded memberships.
+        self.assertFalse(
+            response_body["rooms"][room_id].get("limited", False),
+            "Expected a non-limited timeline",
+        )
+
+        # We should see the reset membership state of user1
+        state_map = self.get_success(
+            self.storage_controllers.state.get_current_state(room_id)
+        )
+        self._assertRequiredStateIncludes(
+            response_body["rooms"][room_id]["required_state"],
+            {
+                state_map[(EventTypes.Member, user1_id)],
+            },
+        )
+        self.assertEqual(
+            response_body["rooms"][room_id]["required_state"][0]["event_id"],
+            first_event_id,
+        )

tests/rest/client/sliding_sync/test_sliding_sync.py

@@ -257,7 +257,7 @@ class SlidingSyncBase(unittest.HomeserverTestCase):
         invitee_user_id: str,
         unsigned_invite_room_state: list[StrippedStateEvent] | None,
         invite_room_id: str | None = None,
-    ) -> str:
+    ) -> tuple[str, EventBase]:
         """
         Create a fake invite for a remote room and persist it.
 
@@ -323,11 +323,13 @@ class SlidingSyncBase(unittest.HomeserverTestCase):
         context = EventContext.for_outlier(self.hs.get_storage_controllers())
         persist_controller = self.hs.get_storage_controllers().persistence
         assert persist_controller is not None
-        self.get_success(persist_controller.persist_event(invite_event, context))
+        persisted_event, _, _ = self.get_success(
+            persist_controller.persist_event(invite_event, context)
+        )
 
         self._remote_invite_count += 1
 
-        return invite_room_id
+        return invite_room_id, persisted_event
 
     def _bump_notifier_wait_for_events(
         self,
@@ -763,7 +765,7 @@ class SlidingSyncTestCase(SlidingSyncBase):
         user1_tok = self.login(user1_id, "pass")
 
         # Create a remote room invite (out-of-band membership)
-        room_id = self._create_remote_invite_room_for_user(user1_id, None)
+        room_id, _ = self._create_remote_invite_room_for_user(user1_id, None)
 
         # Make the Sliding Sync request
         sync_body = {

tests/rest/client/test_login.py

@@ -1728,9 +1728,6 @@ class UsernamePickerTestCase(HomeserverTestCase):
             content_is_form=True,
             custom_headers=[
                 ("Cookie", "username_mapping_session=" + session_id),
-                # old versions of twisted don't do form-parsing without a valid
-                # content-length header.
-                ("Content-Length", str(len(content))),
             ],
         )
         self.assertEqual(chan.code, 302, chan.result)
@@ -1818,9 +1815,6 @@ class UsernamePickerTestCase(HomeserverTestCase):
             content_is_form=True,
             custom_headers=[
                 ("Cookie", "username_mapping_session=" + session_id),
-                # old versions of twisted don't do form-parsing without a valid
-                # content-length header.
-                ("Content-Length", str(len(content))),
             ],
         )
         self.assertEqual(chan.code, 302, chan.result)

tests/rest/client/test_media.py

@@ -2590,7 +2590,6 @@ class AuthenticatedMediaTestCase(unittest.HomeserverTestCase):
             self.tok,
             shorthand=False,
             content_type=b"image/png",
-            custom_headers=[("Content-Length", str(67))],
         )
         self.assertEqual(channel.code, 200)
         res = channel.json_body.get("content_uri")
@@ -2750,7 +2749,6 @@ class AuthenticatedMediaTestCase(unittest.HomeserverTestCase):
             self.tok,
             shorthand=False,
             content_type=b"image/png",
-            custom_headers=[("Content-Length", str(67))],
         )
         self.assertEqual(channel.code, 200)
         res = channel.json_body.get("content_uri")
@@ -2909,7 +2907,6 @@ class MediaUploadLimits(unittest.HomeserverTestCase):
             access_token=self.tok,
             shorthand=False,
             content_type=b"text/plain",
-            custom_headers=[("Content-Length", str(size))],
         )
 
     def test_upload_under_limit(self) -> None:
@@ -3074,7 +3071,6 @@ class MediaUploadLimitsModuleOverrides(unittest.HomeserverTestCase):
             access_token=tok,
             shorthand=False,
             content_type=b"text/plain",
-            custom_headers=[("Content-Length", str(size))],
         )
 
     def test_upload_under_limit(self) -> None:

tests/rest/client/utils.py

@@ -612,7 +612,6 @@ class RestHelper:
             filename: The filename of the media to be uploaded
             expect_code: The return code to expect from attempting to upload the media
         """
-        image_length = len(image_data)
         path = "/_matrix/media/r0/upload?filename=%s" % (filename,)
         channel = make_request(
             self.reactor,
@@ -621,7 +620,6 @@ class RestHelper:
             path,
             content=image_data,
             access_token=tok,
-            custom_headers=[("Content-Length", str(image_length))],
         )
 
         assert channel.code == expect_code, "Expected: %d, got: %d, resp: %r" % (

tests/server.py

@@ -81,6 +81,7 @@ from twisted.web.http_headers import Headers
 from twisted.web.resource import IResource
 from twisted.web.server import Request, Site
 
+from synapse.api.constants import MAX_REQUEST_SIZE
 from synapse.config.database import DatabaseConnectionConfig
 from synapse.config.homeserver import HomeServerConfig
 from synapse.events.auto_accept_invites import InviteAutoAccepter
@@ -146,7 +147,7 @@ class FakeChannel:
     _reactor: MemoryReactorClock
     result: dict = attr.Factory(dict)
     _ip: str = "127.0.0.1"
-    _producer: IPullProducer | IPushProducer | None = None
+    _producer: Optional[Union[IPullProducer, IPushProducer]] = None
     resource_usage: ContextResourceUsage | None = None
     _request: Request | None = None
 
@@ -241,14 +242,13 @@ class FakeChannel:
 
     def loseConnection(self) -> None:
         self.unregisterProducer()
-        self.transport.loseConnection()
 
     # Type ignore: mypy doesn't like the fact that producer isn't an IProducer.
     def registerProducer(self, producer: IProducer, streaming: bool) -> None:
         # TODO This should ensure that the IProducer is an IPushProducer or
         # IPullProducer, unfortunately twisted.protocols.basic.FileSender does
         # implement those, but doesn't declare it.
-        self._producer = cast(IPushProducer | IPullProducer, producer)
+        self._producer = cast(Union[IPushProducer, IPullProducer], producer)
         self.producerStreaming = streaming
 
         def _produce() -> None:
@@ -428,18 +428,29 @@ def make_request(
 
     channel = FakeChannel(site, reactor, ip=client_ip)
 
-    req = request(channel, site, our_server_name="test_server")
+    req = request(
+        channel,
+        site,
+        our_server_name="test_server",
+        max_request_body_size=MAX_REQUEST_SIZE,
+    )
     channel.request = req
 
     req.content = BytesIO(content)
     # Twisted expects to be at the end of the content when parsing the request.
     req.content.seek(0, SEEK_END)
 
-    # Old version of Twisted (<20.3.0) have issues with parsing x-www-form-urlencoded
-    # bodies if the Content-Length header is missing
-    req.requestHeaders.addRawHeader(
-        b"Content-Length", str(len(content)).encode("ascii")
-    )
+    # If `Content-Length` was passed in as a custom header, don't automatically add it
+    # here.
+    if custom_headers is None or not any(
+        (k if isinstance(k, bytes) else k.encode("ascii")) == b"Content-Length"
+        for k, _ in custom_headers
+    ):
+        # Old version of Twisted (<20.3.0) have issues with parsing x-www-form-urlencoded
+        # bodies if the Content-Length header is missing
+        req.requestHeaders.addRawHeader(
+            b"Content-Length", str(len(content)).encode("ascii")
+        )
 
     if access_token:
         req.requestHeaders.addRawHeader(
@@ -841,7 +852,7 @@ class FakeTransport:
     """Test reactor
     """
 
-    _protocol: IProtocol | None = None
+    _protocol: Optional[IProtocol] = None
     """The Protocol which is producing data for this transport. Optional, but if set
     will get called back for connectionLost() notifications etc.
     """
@@ -860,7 +871,7 @@ class FakeTransport:
     disconnected = False
     connected = True
     buffer: bytes = b""
-    producer: IPushProducer | None = None
+    producer: Optional[IPushProducer] = None
     autoflush: bool = True
 
     def getPeer(self) -> IPv4Address | IPv6Address:
@@ -1062,7 +1073,7 @@ def setup_test_homeserver(
     cleanup_func: Callable[[Callable[[], Optional["Deferred[None]"]]], None],
     server_name: str = "test",
     config: HomeServerConfig | None = None,
-    reactor: ISynapseReactor | None = None,
+    reactor: Optional[ISynapseReactor] = None,
     homeserver_to_use: type[HomeServer] = TestHomeServer,
     db_txn_limit: int | None = None,
     **extra_homeserver_attributes: Any,
@@ -1074,10 +1085,10 @@ def setup_test_homeserver(
     If no datastore is supplied, one is created and given to the homeserver.
 
     Args:
-        cleanup_func : The function used to register a cleanup routine for
-                       after the test. If the function returns a Deferred, the
-                       test case will wait until the Deferred has fired before
-                       proceeding to the next cleanup function.
+        cleanup_func: The function used to register a cleanup routine for
+            after the test. If the function returns a Deferred, the
+            test case will wait until the Deferred has fired before
+            proceeding to the next cleanup function.
         server_name: Homeserver name
         config: Homeserver config
         reactor: Twisted reactor
@@ -1190,68 +1201,9 @@ def setup_test_homeserver(
         cur.close()
         db_conn.close()
 
-    hs = homeserver_to_use(
-        server_name,
-        config=config,
-        reactor=reactor,
-    )
-
-    # Capture the `hs` as a `weakref` here to ensure there is no scenario where uncalled
-    # cleanup functions result in holding the `hs` in memory.
-    cleanup_hs_ref = weakref.ref(hs)
-
-    def shutdown_hs_on_cleanup() -> "Deferred[None]":
-        cleanup_hs = cleanup_hs_ref()
-        deferred: "Deferred[None]" = defer.succeed(None)
-        if cleanup_hs is not None:
-            deferred = defer.ensureDeferred(cleanup_hs.shutdown())
-        return deferred
-
-    # Register the cleanup hook for the homeserver.
-    # A full `hs.shutdown()` is necessary otherwise CI tests will fail while exhibiting
-    # strange behaviours.
-    cleanup_func(shutdown_hs_on_cleanup)
-
-    # Install @cache_in_self attributes
-    for key, val in extra_homeserver_attributes.items():
-        setattr(hs, "_" + key, val)
-
-    # Mock TLS
-    hs.tls_server_context_factory = Mock()
-
-    # Patch `make_pool` before initialising the database, to make database transactions
-    # synchronous for testing.
-    with patch("synapse.storage.database.make_pool", side_effect=make_fake_db_pool):
-        hs.setup()
-
-    # Register background tasks required by this server. This must be done
-    # somewhat manually due to the background tasks not being registered
-    # unless handlers are instantiated.
-    #
-    # Since, we don't have to worry about `daemonize` (forking the process) in tests, we
-    # can just start the background tasks straight away after `hs.setup`. (compare this
-    # with where we call `hs.start_background_tasks()` outside of the test environment).
-    if hs.config.worker.run_background_tasks:
-        hs.start_background_tasks()
-
-    # Since we've changed the databases to run DB transactions on the same
-    # thread, we need to stop the event fetcher hogging that one thread.
-    hs.get_datastores().main.USE_DEDICATED_DB_THREADS_FOR_EVENT_FETCHING = False
-
-    if USE_POSTGRES_FOR_TESTS:
-        # Capture the `database_pool` as a `weakref` here to ensure there is no scenario where uncalled
-        # cleanup functions result in holding the `hs` in memory.
-        database_pool = weakref.ref(hs.get_datastores().databases[0])
-
-        # We need to do cleanup on PostgreSQL
         def cleanup() -> None:
             import psycopg2
 
-            # Close all the db pools
-            db_pool = database_pool()
-            if db_pool is not None:
-                db_pool._db_pool.close()
-
             dropped = False
 
             # Drop the test database
@@ -1296,6 +1248,96 @@ def setup_test_homeserver(
             # Register the cleanup hook
             cleanup_func(cleanup)
 
+    hs = homeserver_to_use(
+        server_name,
+        config=config,
+        reactor=reactor,
+    )
+
+    # Capture the `hs` as a `weakref` here to ensure there is no scenario where uncalled
+    # cleanup functions result in holding the `hs` in memory.
+    cleanup_hs_ref = weakref.ref(hs)
+
+    def shutdown_hs_on_cleanup() -> "Deferred[None]":
+        cleanup_hs = cleanup_hs_ref()
+        deferred: "Deferred[None]" = defer.succeed(None)
+        if cleanup_hs is not None:
+            deferred = defer.ensureDeferred(cleanup_hs.shutdown())
+        return deferred
+
+    # Register the cleanup hook for the homeserver.
+    # A full `hs.shutdown()` is necessary otherwise CI tests will fail while exhibiting
+    # strange behaviours.
+    cleanup_func(shutdown_hs_on_cleanup)
+
+    # Install @cache_in_self attributes
+    for key, val in extra_homeserver_attributes.items():
+        setattr(hs, "_" + key, val)
+
+    # Mock TLS
+    hs.tls_server_context_factory = Mock()
+
+    # Patch `make_pool` before initialising the database, to make database transactions
+    # synchronous for testing.
+    with patch("synapse.storage.database.make_pool", side_effect=make_fake_db_pool):
+        hs.setup()
+
+    # Ideally, setup/start would be separated but since this is historically used
+    # throughout tests, we keep the existing behavior for now. We probably just need to
+    # rename this function.
+    start_test_homeserver(hs=hs, cleanup_func=cleanup_func, reactor=reactor)
+
+    return hs
+
+
+def start_test_homeserver(
+    *,
+    hs: HomeServer,
+    cleanup_func: Callable[[Callable[[], Optional["Deferred[None]"]]], None],
+    reactor: ISynapseReactor,
+) -> None:
+    """
+    Start a homeserver for testing.
+
+    Args:
+        hs: The homeserver to start.
+        cleanup_func: The function used to register a cleanup routine for
+            after the test. If the function returns a Deferred, the
+            test case will wait until the Deferred has fired before
+            proceeding to the next cleanup function.
+        reactor: Twisted reactor
+    """
+
+    # Register background tasks required by this server. This must be done
+    # somewhat manually due to the background tasks not being registered
+    # unless handlers are instantiated.
+    #
+    # Since, we don't have to worry about `daemonize` (forking the process) in tests, we
+    # can just start the background tasks straight away after `hs.setup`. (compare this
+    # with where we call `hs.start_background_tasks()` outside of the test environment).
+    if hs.config.worker.run_background_tasks:
+        hs.start_background_tasks()
+
+    # Since we've changed the databases to run DB transactions on the same
+    # thread, we need to stop the event fetcher hogging that one thread.
+    hs.get_datastores().main.USE_DEDICATED_DB_THREADS_FOR_EVENT_FETCHING = False
+
+    if USE_POSTGRES_FOR_TESTS:
+        # Capture the `database_pool` as a `weakref` here to ensure there is no scenario where uncalled
+        # cleanup functions result in holding the `hs` in memory.
+        database_pool = weakref.ref(hs.get_datastores().databases[0])
+
+        # We need to do cleanup on PostgreSQL
+        def cleanup() -> None:
+            # Close all the db pools
+            db_pool = database_pool()
+            if db_pool is not None:
+                db_pool._db_pool.close()
+
+        if not LEAVE_DB:
+            # Register the cleanup hook
+            cleanup_func(cleanup)
+
     # bcrypt is far too slow to be doing in unit tests
     # Need to let the HS build an auth handler and then mess with it
     # because AuthHandler's constructor requires the HS, so we can't make one
@@ -1330,5 +1372,3 @@ def setup_test_homeserver(
     load_legacy_third_party_event_rules(hs)
     load_legacy_presence_router(hs)
     load_legacy_password_auth_providers(hs)
-
-    return hs

tests/storage/test_sliding_sync_tables.py

@@ -30,19 +30,23 @@ from synapse.api.room_versions import RoomVersions
 from synapse.events import EventBase, StrippedStateEvent, make_event_from_dict
 from synapse.events.snapshot import EventContext
 from synapse.rest import admin
-from synapse.rest.client import login, room
+from synapse.rest.client import login, room, sync
 from synapse.server import HomeServer
 from synapse.storage.databases.main.events import DeltaState
 from synapse.storage.databases.main.events_bg_updates import (
     _resolve_stale_data_in_sliding_sync_joined_rooms_table,
     _resolve_stale_data_in_sliding_sync_membership_snapshots_table,
 )
-from synapse.types import create_requester
+from synapse.types import SlidingSyncStreamToken, create_requester
+from synapse.types.handlers.sliding_sync import (
+    LAZY_MEMBERS_UPDATE_INTERVAL,
+    StateValues,
+)
 from synapse.types.storage import _BackgroundUpdates
 from synapse.util.clock import Clock
 
+from tests.rest.client.sliding_sync.test_sliding_sync import SlidingSyncBase
 from tests.test_utils.event_injection import create_event
-from tests.unittest import HomeserverTestCase
 
 logger = logging.getLogger(__name__)
 
@@ -86,7 +90,7 @@ class _SlidingSyncMembershipSnapshotResult:
     forgotten: bool = False
 
 
-class SlidingSyncTablesTestCaseBase(HomeserverTestCase):
+class SlidingSyncTablesTestCaseBase(SlidingSyncBase):
     """
     Helpers to deal with testing that the
     `sliding_sync_joined_rooms`/`sliding_sync_membership_snapshots` database tables are
@@ -97,6 +101,7 @@ class SlidingSyncTablesTestCaseBase(HomeserverTestCase):
         admin.register_servlets,
         login.register_servlets,
         room.register_servlets,
+        sync.register_servlets,
     ]
 
     def prepare(self, reactor: MemoryReactor, clock: Clock, hs: HomeServer) -> None:
@@ -202,78 +207,6 @@ class SlidingSyncTablesTestCaseBase(HomeserverTestCase):
             for row in rows
         }
 
-    _remote_invite_count: int = 0
-
-    def _create_remote_invite_room_for_user(
-        self,
-        invitee_user_id: str,
-        unsigned_invite_room_state: list[StrippedStateEvent] | None,
-    ) -> tuple[str, EventBase]:
-        """
-        Create a fake invite for a remote room and persist it.
-
-        We don't have any state for these kind of rooms and can only rely on the
-        stripped state included in the unsigned portion of the invite event to identify
-        the room.
-
-        Args:
-            invitee_user_id: The person being invited
-            unsigned_invite_room_state: List of stripped state events to assist the
-                receiver in identifying the room.
-
-        Returns:
-            The room ID of the remote invite room and the persisted remote invite event.
-        """
-        invite_room_id = f"!test_room{self._remote_invite_count}:remote_server"
-
-        invite_event_dict = {
-            "room_id": invite_room_id,
-            "sender": "@inviter:remote_server",
-            "state_key": invitee_user_id,
-            "depth": 1,
-            "origin_server_ts": 1,
-            "type": EventTypes.Member,
-            "content": {"membership": Membership.INVITE},
-            "auth_events": [],
-            "prev_events": [],
-        }
-        if unsigned_invite_room_state is not None:
-            serialized_stripped_state_events = []
-            for stripped_event in unsigned_invite_room_state:
-                serialized_stripped_state_events.append(
-                    {
-                        "type": stripped_event.type,
-                        "state_key": stripped_event.state_key,
-                        "sender": stripped_event.sender,
-                        "content": stripped_event.content,
-                    }
-                )
-
-            invite_event_dict["unsigned"] = {
-                "invite_room_state": serialized_stripped_state_events
-            }
-
-        invite_event = make_event_from_dict(
-            invite_event_dict,
-            room_version=RoomVersions.V10,
-        )
-        invite_event.internal_metadata.outlier = True
-        invite_event.internal_metadata.out_of_band_membership = True
-
-        self.get_success(
-            self.store.maybe_store_room_on_outlier_membership(
-                room_id=invite_room_id, room_version=invite_event.room_version
-            )
-        )
-        context = EventContext.for_outlier(self.hs.get_storage_controllers())
-        persisted_event, _, _ = self.get_success(
-            self.persist_controller.persist_event(invite_event, context)
-        )
-
-        self._remote_invite_count += 1
-
-        return invite_room_id, persisted_event
-
     def _retract_remote_invite_for_user(
         self,
         user_id: str,
@@ -3052,6 +2985,141 @@ class SlidingSyncTablesTestCase(SlidingSyncTablesTestCaseBase):
             exact=True,
         )
 
+    def test_lazy_loading_room_members_last_seen_ts(self) -> None:
+        """Test that the `last_seen_ts` column in
+        `sliding_sync_connection_lazy_members` is correctly kept up to date.
+
+        We expect that it only gets updated every
+        `LAZY_MEMBERS_UPDATE_INTERVAL`, rather than on every sync.
+        """
+
+        user1_id = self.register_user("user1", "pass")
+        user1_tok = self.login(user1_id, "pass")
+        user2_id = self.register_user("user2", "pass")
+        user2_tok = self.login(user2_id, "pass")
+
+        room_id = self.helper.create_room_as(user2_id, tok=user2_tok, is_public=True)
+        self.helper.join(room_id, user1_id, tok=user1_tok)
+
+        # Send a message so that user1 comes down sync.
+        self.helper.send(room_id, "msg", tok=user1_tok)
+
+        sync_body = {
+            "lists": {
+                "foo-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [
+                        [EventTypes.Member, StateValues.LAZY],
+                    ],
+                    "timeline_limit": 1,
+                }
+            }
+        }
+        response_body, from_token = self.do_sync(sync_body, tok=user1_tok)
+
+        # Check that user1 is returned
+        state_map = self.get_success(
+            self.storage_controllers.state.get_current_state(room_id)
+        )
+        self._assertRequiredStateIncludes(
+            response_body["rooms"][room_id]["required_state"],
+            {
+                state_map[(EventTypes.Member, user1_id)],
+            },
+            exact=True,
+        )
+
+        # Check that we have an entry in sliding_sync_connection_lazy_members
+        connection_pos1 = self.get_success(
+            SlidingSyncStreamToken.from_string(self.store, from_token)
+        ).connection_position
+        lazy_member_entries = self.get_success(
+            self.store.get_sliding_sync_connection_lazy_members(
+                connection_pos1, room_id, {user1_id}
+            )
+        )
+        self.assertIn(user1_id, lazy_member_entries)
+
+        prev_timestamp = lazy_member_entries[user1_id]
+
+        # If user1 sends a message then we consider it for lazy loading. We have
+        # previously returned it so we don't send the state down again, but it
+        # is still eligible for updating the timestamp. Since we last updated
+        # the timestamp within the last `LAZY_MEMBERS_UPDATE_INTERVAL`, we do not
+        # update it.
+        self.helper.send(room_id, "msg2", tok=user1_tok)
+
+        response_body, from_token = self.do_sync(
+            sync_body, since=from_token, tok=user1_tok
+        )
+
+        # We expect the required_state map to be empty as nothing has changed.
+        state_map = self.get_success(
+            self.storage_controllers.state.get_current_state(room_id)
+        )
+        self._assertRequiredStateIncludes(
+            response_body["rooms"][room_id].get("required_state", []),
+            {},
+            exact=True,
+        )
+
+        connection_pos2 = self.get_success(
+            SlidingSyncStreamToken.from_string(self.store, from_token)
+        ).connection_position
+
+        lazy_member_entries = self.get_success(
+            self.store.get_sliding_sync_connection_lazy_members(
+                connection_pos2, room_id, {user1_id}
+            )
+        )
+
+        # The timestamp should be unchanged.
+        self.assertEqual(lazy_member_entries[user1_id], prev_timestamp)
+
+        # Now advance the time by `LAZY_MEMBERS_UPDATE_INTERVAL` so that we
+        # would update the timestamp.
+        self.reactor.advance(LAZY_MEMBERS_UPDATE_INTERVAL.as_secs())
+
+        # Send a message from user2
+        self.helper.send(room_id, "msg3", tok=user2_tok)
+
+        response_body, from_token = self.do_sync(
+            sync_body, since=from_token, tok=user1_tok
+        )
+
+        connection_pos3 = self.get_success(
+            SlidingSyncStreamToken.from_string(self.store, from_token)
+        ).connection_position
+
+        lazy_member_entries = self.get_success(
+            self.store.get_sliding_sync_connection_lazy_members(
+                connection_pos3, room_id, {user1_id}
+            )
+        )
+
+        # The timestamp for user1 should be unchanged, as they were not sent down.
+        self.assertEqual(lazy_member_entries[user1_id], prev_timestamp)
+
+        # Now if user1 sends a message, then the timestamp should be updated as
+        # its been over `LAZY_MEMBERS_UPDATE_INTERVAL` since we last updated it.
+        # (Even though we don't send the state down again).
+        self.helper.send(room_id, "msg4", tok=user1_tok)
+
+        response_body, from_token = self.do_sync(
+            sync_body, since=from_token, tok=user1_tok
+        )
+        connection_pos4 = self.get_success(
+            SlidingSyncStreamToken.from_string(self.store, from_token)
+        ).connection_position
+
+        lazy_member_entries = self.get_success(
+            self.store.get_sliding_sync_connection_lazy_members(
+                connection_pos4, room_id, {user1_id}
+            )
+        )
+        # The timestamp for user1 should be updated.
+        self.assertGreater(lazy_member_entries[user1_id], prev_timestamp)
+
 
 class SlidingSyncTablesBackgroundUpdatesTestCase(SlidingSyncTablesTestCaseBase):
     """

tests/test_server.py

@@ -212,6 +212,66 @@ class JsonResourceTests(unittest.TestCase):
         self.assertEqual(channel.code, 200)
         self.assertNotIn("body", channel.result)
 
+    def test_content_larger_than_content_length(self) -> None:
+        """
+        HTTP requests with content size exceeding Content-Length should be rejected with 400.
+        """
+
+        def _callback(
+            request: SynapseRequest, **kwargs: object
+        ) -> tuple[int, JsonDict]:
+            return 200, {}
+
+        res = JsonResource(self.homeserver)
+        res.register_paths(
+            "POST", [re.compile("^/_matrix/foo$")], _callback, "test_servlet"
+        )
+
+        channel = make_request(
+            self.reactor,
+            FakeSite(res, self.reactor),
+            b"POST",
+            b"/_matrix/foo",
+            {},
+            # Set the `Content-Length` value to be smaller than the actual content size
+            custom_headers=[("Content-Length", "1")],
+            # The request should disconnect early so don't await the result
+            await_result=False,
+        )
+
+        self.reactor.advance(0.1)
+        self.assertEqual(channel.code, 400)
+
+    def test_content_smaller_than_content_length(self) -> None:
+        """
+        HTTP requests with content size smaller than Content-Length should be rejected with 400.
+        """
+
+        def _callback(
+            request: SynapseRequest, **kwargs: object
+        ) -> tuple[int, JsonDict]:
+            return 200, {}
+
+        res = JsonResource(self.homeserver)
+        res.register_paths(
+            "POST", [re.compile("^/_matrix/foo$")], _callback, "test_servlet"
+        )
+
+        channel = make_request(
+            self.reactor,
+            FakeSite(res, self.reactor),
+            b"POST",
+            b"/_matrix/foo",
+            {},
+            # Set the `Content-Length` value to be larger than the actual content size
+            custom_headers=[("Content-Length", "10")],
+            # The request should disconnect early so don't await the result
+            await_result=False,
+        )
+
+        self.reactor.advance(0.1)
+        self.assertEqual(channel.code, 400)
+
 
 class OptionsResourceTests(unittest.TestCase):
     def setUp(self) -> None:

tests/unittest.py

@@ -37,6 +37,7 @@ from typing import (
     Iterable,
     Mapping,
     NoReturn,
+    Optional,
     Protocol,
     TypeVar,
 )
@@ -636,7 +637,7 @@ class HomeserverTestCase(TestCase):
         self,
         server_name: str | None = None,
         config: JsonDict | None = None,
-        reactor: ISynapseReactor | None = None,
+        reactor: Optional[ISynapseReactor] = None,
         clock: Clock | None = None,
         **extra_homeserver_attributes: Any,
     ) -> HomeServer: