Merge remote-tracking branch 'upstream/release-v1.114'

2024-10-01 01:36:05 -04:00 · 2024-08-20 17:02:34 +03:00 · 2024-08-20 17:02:34 +03:00 · 58d466f3c9
commit 58d466f3c9
parent f3b332a585 a8e313836d
55 changed files with 3071 additions and 1305 deletions
--- a/.github/workflows/docker.yml
+++ b/.github/workflows/docker.yml
@ -30,7 +30,7 @@ jobs:
        run: docker buildx inspect

      - name: Install Cosign
-        uses: sigstore/cosign-installer@v3.5.0
+        uses: sigstore/cosign-installer@v3.6.0

      - name: Checkout repository
        uses: actions/checkout@v4
--- a/CHANGES.md
+++ b/CHANGES.md
@ -1,3 +1,57 @@
+# Synapse 1.114.0rc1 (2024-08-20)
+
+### Features
+
+- Add a flag to `/versions`, `org.matrix.simplified_msc3575`, to indicate whether experimental sliding sync support has been enabled. ([\#17571](https://github.com/element-hq/synapse/issues/17571))
+- Handle changes in `timeline_limit` in experimental sliding sync. ([\#17579](https://github.com/element-hq/synapse/issues/17579))
+- Correctly track read receipts that should be sent down in experimental sliding sync. ([\#17575](https://github.com/element-hq/synapse/issues/17575), [\#17589](https://github.com/element-hq/synapse/issues/17589), [\#17592](https://github.com/element-hq/synapse/issues/17592))
+
+### Bugfixes
+
+- Start handlers for new media endpoints when media resource configured. ([\#17483](https://github.com/element-hq/synapse/issues/17483))
+- Fix timeline ordering (using `stream_ordering` instead of topological ordering) in experimental [MSC3575](https://github.com/matrix-org/matrix-spec-proposals/pull/3575) Sliding Sync `/sync` endpoint. ([\#17510](https://github.com/element-hq/synapse/issues/17510))
+- Fix experimental sliding sync implementation to remember any updates in rooms that were not sent down immediately. ([\#17535](https://github.com/element-hq/synapse/issues/17535))
+- Better exclude partially stated rooms if we must await full state in experimental [MSC3575](https://github.com/matrix-org/matrix-spec-proposals/pull/3575) Sliding Sync `/sync` endpoint. ([\#17538](https://github.com/element-hq/synapse/issues/17538))
+- Handle lower-case http headers in `_Mulitpart_Parser_Protocol`. ([\#17545](https://github.com/element-hq/synapse/issues/17545))
+- Fix fetching federation signing keys from servers that omit `old_verify_keys`. Contributed by @tulir @ Beeper. ([\#17568](https://github.com/element-hq/synapse/issues/17568))
+- Fix bug where we would respond with an error when a remote server asked for media that had a length of 0, using the new multipart federation media endpoint. ([\#17570](https://github.com/element-hq/synapse/issues/17570))
+
+### Improved Documentation
+
+- Clarify default behaviour of the
+  [`auto_accept_invites.worker_to_run_on`](https://element-hq.github.io/synapse/develop/usage/configuration/config_documentation.html#auto-accept-invites)
+  option. ([\#17515](https://github.com/element-hq/synapse/issues/17515))
+- Improve docstrings for profile methods. ([\#17559](https://github.com/element-hq/synapse/issues/17559))
+
+### Internal Changes
+
+- Add more tracing to experimental [MSC3575](https://github.com/matrix-org/matrix-spec-proposals/pull/3575) Sliding Sync `/sync` endpoint. ([\#17514](https://github.com/element-hq/synapse/issues/17514))
+- Fixup comment in sliding sync implementation. ([\#17531](https://github.com/element-hq/synapse/issues/17531))
+- Replace override of deprecated method `HTTPAdapter.get_connection` with `get_connection_with_tls_context`. ([\#17536](https://github.com/element-hq/synapse/issues/17536))
+- Fix performance of device lists in `/key/changes` and sliding sync. ([\#17537](https://github.com/element-hq/synapse/issues/17537), [\#17548](https://github.com/element-hq/synapse/issues/17548))
+- Bump setuptools from 67.6.0 to 72.1.0. ([\#17542](https://github.com/element-hq/synapse/issues/17542))
+- Add a utility function for generating random event IDs. ([\#17557](https://github.com/element-hq/synapse/issues/17557))
+- Speed up responding to media requests. ([\#17558](https://github.com/element-hq/synapse/issues/17558), [\#17561](https://github.com/element-hq/synapse/issues/17561), [\#17564](https://github.com/element-hq/synapse/issues/17564), [\#17566](https://github.com/element-hq/synapse/issues/17566), [\#17567](https://github.com/element-hq/synapse/issues/17567), [\#17569](https://github.com/element-hq/synapse/issues/17569))
+- Test github token before running release script steps. ([\#17562](https://github.com/element-hq/synapse/issues/17562))
+- Reduce log spam of multipart files. ([\#17563](https://github.com/element-hq/synapse/issues/17563))
+- Refactor per-connection state in experimental sliding sync handler. ([\#17574](https://github.com/element-hq/synapse/issues/17574))
+- Add histogram metrics for sliding sync processing time. ([\#17593](https://github.com/element-hq/synapse/issues/17593))
+
+
+
+### Updates to locked dependencies
+
+* Bump bytes from 1.6.1 to 1.7.1. ([\#17526](https://github.com/element-hq/synapse/issues/17526))
+* Bump lxml from 5.2.2 to 5.3.0. ([\#17550](https://github.com/element-hq/synapse/issues/17550))
+* Bump phonenumbers from 8.13.42 to 8.13.43. ([\#17551](https://github.com/element-hq/synapse/issues/17551))
+* Bump regex from 1.10.5 to 1.10.6. ([\#17527](https://github.com/element-hq/synapse/issues/17527))
+* Bump sentry-sdk from 2.10.0 to 2.12.0. ([\#17553](https://github.com/element-hq/synapse/issues/17553))
+* Bump serde from 1.0.204 to 1.0.206. ([\#17556](https://github.com/element-hq/synapse/issues/17556))
+* Bump serde_json from 1.0.122 to 1.0.124. ([\#17555](https://github.com/element-hq/synapse/issues/17555))
+* Bump sigstore/cosign-installer from 3.5.0 to 3.6.0. ([\#17549](https://github.com/element-hq/synapse/issues/17549))
+* Bump types-pyyaml from 6.0.12.20240311 to 6.0.12.20240808. ([\#17552](https://github.com/element-hq/synapse/issues/17552))
+* Bump types-requests from 2.31.0.20240406 to 2.32.0.20240712. ([\#17524](https://github.com/element-hq/synapse/issues/17524))
+
 # Synapse 1.113.0 (2024-08-13)

 No significant changes since 1.113.0rc1.
--- a/Cargo.lock
+++ b/Cargo.lock
@ -67,9 +67,9 @@ checksum = "79296716171880943b8470b5f8d03aa55eb2e645a4874bdbb28adb49162e012c"

 [[package]]
 name = "bytes"
-version = "1.6.1"
+version = "1.7.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "a12916984aab3fa6e39d655a33e09c0071eb36d6ab3aea5c2d78551f1df6d952"
+checksum = "8318a53db07bb3f8dca91a600466bdb3f2eaadeedfdbcf02e1accbad9271ba50"

 [[package]]
 name = "cfg-if"
@ -444,9 +444,9 @@ dependencies = [

 [[package]]
 name = "regex"
-version = "1.10.5"
+version = "1.10.6"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b91213439dad192326a0d7c6ee3955910425f441d7038e0d6933b0aec5c4517f"
+checksum = "4219d74c6b67a3654a9fbebc4b419e22126d13d2f3c4a07ee0cb61ff79a79619"
 dependencies = [
 "aho-corasick",
 "memchr",
@ -485,18 +485,18 @@ checksum = "94143f37725109f92c262ed2cf5e59bce7498c01bcc1502d7b9afe439a4e9f49"

 [[package]]
 name = "serde"
-version = "1.0.204"
+version = "1.0.206"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "bc76f558e0cbb2a839d37354c575f1dc3fdc6546b5be373ba43d95f231bf7c12"
+checksum = "5b3e4cd94123dd520a128bcd11e34d9e9e423e7e3e50425cb1b4b1e3549d0284"
 dependencies = [
 "serde_derive",
 ]

 [[package]]
 name = "serde_derive"
-version = "1.0.204"
+version = "1.0.206"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "e0cd7e117be63d3c3678776753929474f3b04a43a080c744d6b0ae2a8c28e222"
+checksum = "fabfb6138d2383ea8208cf98ccf69cdfb1aff4088460681d84189aa259762f97"
 dependencies = [
 "proc-macro2",
 "quote",
@ -505,9 +505,9 @@ dependencies = [

 [[package]]
 name = "serde_json"
-version = "1.0.122"
+version = "1.0.124"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "784b6203951c57ff748476b126ccb5e8e2959a5c19e5c617ab1956be3dbc68da"
+checksum = "66ad62847a56b3dba58cc891acd13884b9c61138d330c0d7b6181713d4fce38d"
 dependencies = [
 "itoa",
 "memchr",
--- a/debian/changelog
+++ b/debian/changelog
@ -1,3 +1,9 @@
+matrix-synapse-py3 (1.114.0~rc1) stable; urgency=medium
+
+  * New synapse release 1.114.0rc1.
+
+ -- Synapse Packaging team <packages@matrix.org>  Tue, 20 Aug 2024 12:55:28 +0000
+
 matrix-synapse-py3 (1.113.0) stable; urgency=medium

  * New Synapse release 1.113.0.
--- a/docs/development/room-dag-concepts.md
+++ b/docs/development/room-dag-concepts.md
@ -21,8 +21,10 @@ incrementing integer, but backfilled events start with `stream_ordering=-1` and

 ---

- - `/sync` returns things in the order they arrive at the server (`stream_ordering`).
- - `/messages` (and `/backfill` in the federation API) return them in the order determined by the event graph `(topological_ordering, stream_ordering)`.
+ - Incremental `/sync?since=xxx` returns things in the order they arrive at the server
+   (`stream_ordering`).
+ - Initial `/sync`, `/messages` (and `/backfill` in the federation API) return them in
+   the order determined by the event graph `(topological_ordering, stream_ordering)`.

 The general idea is that, if you're following a room in real-time (i.e.
 `/sync`), you probably want to see the messages as they arrive at your server,
--- a/docs/usage/configuration/config_documentation.md
+++ b/docs/usage/configuration/config_documentation.md
@ -4685,7 +4685,9 @@ This setting has the following sub-options:
 * `only_for_direct_messages`: Whether invites should be automatically accepted for all room types, or only
   for direct messages. Defaults to false.
 * `only_from_local_users`: Whether to only automatically accept invites from users on this homeserver. Defaults to false.
-* `worker_to_run_on`: Which worker to run this module on. This must match the "worker_name".
+* `worker_to_run_on`: Which worker to run this module on. This must match 
+  the "worker_name". If not set or `null`, invites will be accepted on the
+  main process.

 NOTE: Care should be taken not to enable this setting if the `synapse_auto_accept_invite` module is enabled and installed.
 The two modules will compete to perform the same task and may result in undesired behaviour. For example, multiple join
--- a/poetry.lock
+++ b/poetry.lock
@ -998,153 +998,149 @@ pyasn1 = ">=0.4.6"

 [[package]]
 name = "lxml"
-version = "5.2.2"
+version = "5.3.0"
 description = "Powerful and Pythonic XML processing library combining libxml2/libxslt with the ElementTree API."
 optional = true
 python-versions = ">=3.6"
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    {file = "PyYAML-6.0.1-cp39-cp39-win_amd64.whl", hash = "sha256:510c9deebc5c0225e8c96813043e62b680ba2f9c50a08d3724c7f28a747d1486"},
    {file = "PyYAML-6.0.1.tar.gz", hash = "sha256:bfdf460b1736c775f2ba9f6a92bca30bc2095067b8a9d77876d1fad6cc3b4a43"},
@ -2418,13 +2403,13 @@ doc = ["Sphinx", "sphinx-rtd-theme"]

 [[package]]
 name = "sentry-sdk"
-version = "2.10.0"
+version = "2.12.0"
 description = "Python client for Sentry (https://sentry.io)"
 optional = true
 python-versions = ">=3.6"
 files = [
-    {file = "sentry_sdk-2.10.0-py2.py3-none-any.whl", hash = "sha256:87b3d413c87d8e7f816cc9334bff255a83d8b577db2b22042651c30c19c09190"},
-    {file = "sentry_sdk-2.10.0.tar.gz", hash = "sha256:545fcc6e36c335faa6d6cda84669b6e17025f31efbf3b2211ec14efe008b75d1"},
+    {file = "sentry_sdk-2.12.0-py2.py3-none-any.whl", hash = "sha256:7a8d5163d2ba5c5f4464628c6b68f85e86972f7c636acc78aed45c61b98b7a5e"},
+    {file = "sentry_sdk-2.12.0.tar.gz", hash = "sha256:8763840497b817d44c49b3fe3f5f7388d083f2337ffedf008b2cdb63b5c86dc6"},
 ]

 [package.dependencies]
@ -2454,7 +2439,7 @@ langchain = ["langchain (>=0.0.210)"]
 loguru = ["loguru (>=0.5)"]
 openai = ["openai (>=1.0.0)", "tiktoken (>=0.3.0)"]
 opentelemetry = ["opentelemetry-distro (>=0.35b0)"]
-opentelemetry-experimental = ["opentelemetry-instrumentation-aio-pika (==0.46b0)", "opentelemetry-instrumentation-aiohttp-client (==0.46b0)", "opentelemetry-instrumentation-aiopg (==0.46b0)", "opentelemetry-instrumentation-asgi (==0.46b0)", "opentelemetry-instrumentation-asyncio (==0.46b0)", "opentelemetry-instrumentation-asyncpg (==0.46b0)", "opentelemetry-instrumentation-aws-lambda (==0.46b0)", "opentelemetry-instrumentation-boto (==0.46b0)", "opentelemetry-instrumentation-boto3sqs (==0.46b0)", "opentelemetry-instrumentation-botocore (==0.46b0)", "opentelemetry-instrumentation-cassandra (==0.46b0)", "opentelemetry-instrumentation-celery (==0.46b0)", "opentelemetry-instrumentation-confluent-kafka (==0.46b0)", "opentelemetry-instrumentation-dbapi (==0.46b0)", "opentelemetry-instrumentation-django (==0.46b0)", "opentelemetry-instrumentation-elasticsearch (==0.46b0)", "opentelemetry-instrumentation-falcon (==0.46b0)", "opentelemetry-instrumentation-fastapi (==0.46b0)", "opentelemetry-instrumentation-flask (==0.46b0)", "opentelemetry-instrumentation-grpc (==0.46b0)", "opentelemetry-instrumentation-httpx (==0.46b0)", "opentelemetry-instrumentation-jinja2 (==0.46b0)", "opentelemetry-instrumentation-kafka-python (==0.46b0)", "opentelemetry-instrumentation-logging (==0.46b0)", "opentelemetry-instrumentation-mysql (==0.46b0)", "opentelemetry-instrumentation-mysqlclient (==0.46b0)", "opentelemetry-instrumentation-pika (==0.46b0)", "opentelemetry-instrumentation-psycopg (==0.46b0)", "opentelemetry-instrumentation-psycopg2 (==0.46b0)", "opentelemetry-instrumentation-pymemcache (==0.46b0)", "opentelemetry-instrumentation-pymongo (==0.46b0)", "opentelemetry-instrumentation-pymysql (==0.46b0)", "opentelemetry-instrumentation-pyramid (==0.46b0)", "opentelemetry-instrumentation-redis (==0.46b0)", "opentelemetry-instrumentation-remoulade (==0.46b0)", "opentelemetry-instrumentation-requests (==0.46b0)", "opentelemetry-instrumentation-sklearn (==0.46b0)", "opentelemetry-instrumentation-sqlalchemy (==0.46b0)", "opentelemetry-instrumentation-sqlite3 (==0.46b0)", "opentelemetry-instrumentation-starlette (==0.46b0)", "opentelemetry-instrumentation-system-metrics (==0.46b0)", "opentelemetry-instrumentation-threading (==0.46b0)", "opentelemetry-instrumentation-tornado (==0.46b0)", "opentelemetry-instrumentation-tortoiseorm (==0.46b0)", "opentelemetry-instrumentation-urllib (==0.46b0)", "opentelemetry-instrumentation-urllib3 (==0.46b0)", "opentelemetry-instrumentation-wsgi (==0.46b0)"]
+opentelemetry-experimental = ["opentelemetry-distro"]
 pure-eval = ["asttokens", "executing", "pure-eval"]
 pymongo = ["pymongo (>=3.1)"]
 pyspark = ["pyspark (>=2.4.4)"]
@ -2492,19 +2477,19 @@ tests = ["coverage[toml] (>=5.0.2)", "pytest"]

 [[package]]
 name = "setuptools"
-version = "67.6.0"
+version = "72.1.0"
 description = "Easily download, build, install, upgrade, and uninstall Python packages"
 optional = false
-python-versions = ">=3.7"
+python-versions = ">=3.8"
 files = [
-    {file = "setuptools-67.6.0-py3-none-any.whl", hash = "sha256:b78aaa36f6b90a074c1fa651168723acbf45d14cb1196b6f02c0fd07f17623b2"},
-    {file = "setuptools-67.6.0.tar.gz", hash = "sha256:2ee892cd5f29f3373097f5a814697e397cf3ce313616df0af11231e2ad118077"},
+    {file = "setuptools-72.1.0-py3-none-any.whl", hash = "sha256:5a03e1860cf56bb6ef48ce186b0e557fdba433237481a9a625176c2831be15d1"},
+    {file = "setuptools-72.1.0.tar.gz", hash = "sha256:8d243eff56d095e5817f796ede6ae32941278f542e0f941867cc05ae52b162ec"},
 ]

 [package.extras]
-docs = ["furo", "jaraco.packaging (>=9)", "jaraco.tidelift (>=1.4)", "pygments-github-lexers (==0.0.5)", "rst.linker (>=1.9)", "sphinx (>=3.5)", "sphinx-favicon", "sphinx-hoverxref (<2)", "sphinx-inline-tabs", "sphinx-lint", "sphinx-notfound-page (==0.8.3)", "sphinx-reredirects", "sphinxcontrib-towncrier"]
-testing = ["build[virtualenv]", "filelock (>=3.4.0)", "flake8 (<5)", "flake8-2020", "ini2toml[lite] (>=0.9)", "jaraco.envs (>=2.2)", "jaraco.path (>=3.2.0)", "pip (>=19.1)", "pip-run (>=8.8)", "pytest (>=6)", "pytest-black (>=0.3.7)", "pytest-checkdocs (>=2.4)", "pytest-cov", "pytest-enabler (>=1.3)", "pytest-flake8", "pytest-mypy (>=0.9.1)", "pytest-perf", "pytest-timeout", "pytest-xdist", "tomli-w (>=1.0.0)", "virtualenv (>=13.0.0)", "wheel"]
-testing-integration = ["build[virtualenv]", "filelock (>=3.4.0)", "jaraco.envs (>=2.2)", "jaraco.path (>=3.2.0)", "pytest", "pytest-enabler", "pytest-xdist", "tomli", "virtualenv (>=13.0.0)", "wheel"]
+core = ["importlib-metadata (>=6)", "importlib-resources (>=5.10.2)", "jaraco.text (>=3.7)", "more-itertools (>=8.8)", "ordered-set (>=3.1.1)", "packaging (>=24)", "platformdirs (>=2.6.2)", "tomli (>=2.0.1)", "wheel (>=0.43.0)"]
+doc = ["furo", "jaraco.packaging (>=9.3)", "jaraco.tidelift (>=1.4)", "pygments-github-lexers (==0.0.5)", "pyproject-hooks (!=1.1)", "rst.linker (>=1.9)", "sphinx (>=3.5)", "sphinx-favicon", "sphinx-inline-tabs", "sphinx-lint", "sphinx-notfound-page (>=1,<2)", "sphinx-reredirects", "sphinxcontrib-towncrier"]
+test = ["build[virtualenv] (>=1.0.3)", "filelock (>=3.4.0)", "importlib-metadata", "ini2toml[lite] (>=0.14)", "jaraco.develop (>=7.21)", "jaraco.envs (>=2.2)", "jaraco.path (>=3.2.0)", "jaraco.test", "mypy (==1.11.*)", "packaging (>=23.2)", "pip (>=19.1)", "pyproject-hooks (!=1.1)", "pytest (>=6,!=8.1.*)", "pytest-checkdocs (>=2.4)", "pytest-cov", "pytest-enabler (>=2.2)", "pytest-home (>=0.5)", "pytest-mypy", "pytest-perf", "pytest-ruff (<0.4)", "pytest-ruff (>=0.2.1)", "pytest-ruff (>=0.3.2)", "pytest-subprocess", "pytest-timeout", "pytest-xdist (>=3)", "tomli", "tomli-w (>=1.0.0)", "virtualenv (>=13.0.0)", "wheel"]

 [[package]]
 name = "setuptools-rust"
@ -2890,24 +2875,24 @@ types-cffi = "*"

 [[package]]
 name = "types-pyyaml"
-version = "6.0.12.20240311"
+version = "6.0.12.20240808"
 description = "Typing stubs for PyYAML"
 optional = false
 python-versions = ">=3.8"
 files = [
-    {file = "types-PyYAML-6.0.12.20240311.tar.gz", hash = "sha256:a9e0f0f88dc835739b0c1ca51ee90d04ca2a897a71af79de9aec5f38cb0a5342"},
-    {file = "types_PyYAML-6.0.12.20240311-py3-none-any.whl", hash = "sha256:b845b06a1c7e54b8e5b4c683043de0d9caf205e7434b3edc678ff2411979b8f6"},
+    {file = "types-PyYAML-6.0.12.20240808.tar.gz", hash = "sha256:b8f76ddbd7f65440a8bda5526a9607e4c7a322dc2f8e1a8c405644f9a6f4b9af"},
+    {file = "types_PyYAML-6.0.12.20240808-py3-none-any.whl", hash = "sha256:deda34c5c655265fc517b546c902aa6eed2ef8d3e921e4765fe606fe2afe8d35"},
 ]

 [[package]]
 name = "types-requests"
-version = "2.31.0.20240406"
+version = "2.32.0.20240712"
 description = "Typing stubs for requests"
 optional = false
 python-versions = ">=3.8"
 files = [
-    {file = "types-requests-2.31.0.20240406.tar.gz", hash = "sha256:4428df33c5503945c74b3f42e82b181e86ec7b724620419a2966e2de604ce1a1"},
-    {file = "types_requests-2.31.0.20240406-py3-none-any.whl", hash = "sha256:6216cdac377c6b9a040ac1c0404f7284bd13199c0e1bb235f4324627e8898cf5"},
+    {file = "types-requests-2.32.0.20240712.tar.gz", hash = "sha256:90c079ff05e549f6bf50e02e910210b98b8ff1ebdd18e19c873cd237737c1358"},
+    {file = "types_requests-2.32.0.20240712-py3-none-any.whl", hash = "sha256:f754283e152c752e46e70942fa2a146b5bc70393522257bb85bd1ef7e019dcc3"},
 ]

 [package.dependencies]
--- a/pyproject.toml
+++ b/pyproject.toml
@ -97,7 +97,7 @@ module-name = "synapse.synapse_rust"

 [tool.poetry]
 name = "matrix-synapse"
-version = "1.113.0"
+version = "1.114.0rc1"
 description = "Homeserver for the Matrix decentralised comms protocol"
 authors = ["Matrix.org Team and Contributors <packages@matrix.org>"]
 license = "AGPL-3.0-or-later"
--- a/requirements.txt
+++ b/requirements.txt
@ -438,149 +438,145 @@ jsonschema-specifications==2023.6.1 ; python_version >= "3.8" and python_full_ve
 jsonschema==4.23.0 ; python_version >= "3.8" and python_full_version < "4.0.0" \
    --hash=sha256:d71497fef26351a33265337fa77ffeb82423f3ea21283cd9467bb03999266bc4 \
    --hash=sha256:fbadb6f8b144a8f8cf9f0b89ba94501d143e50411a1278633f56a7acf7fd5566
-lxml==5.2.2 ; python_full_version >= "3.8.0" and python_full_version < "4.0.0" \
-    --hash=sha256:02437fb7308386867c8b7b0e5bc4cd4b04548b1c5d089ffb8e7b31009b961dc3 \
-    --hash=sha256:02f6a8eb6512fdc2fd4ca10a49c341c4e109aa6e9448cc4859af5b949622715a \
-    --hash=sha256:05f8757b03208c3f50097761be2dea0aba02e94f0dc7023ed73a7bb14ff11eb0 \
-    --hash=sha256:06668e39e1f3c065349c51ac27ae430719d7806c026fec462e5693b08b95696b \
-    --hash=sha256:07542787f86112d46d07d4f3c4e7c760282011b354d012dc4141cc12a68cef5f \
-    --hash=sha256:08ea0f606808354eb8f2dfaac095963cb25d9d28e27edcc375d7b30ab01abbf6 \
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+    --hash=sha256:9c52100e2c2dbb0649b90467935c4b0de5528833c76a35ea1a2691ec9f1ee7a1 \
+    --hash=sha256:9e41506fec7a7f9405b14aa2d5c8abbb4dbbd09d88f9496958b6d00cb4d45330 \
+    --hash=sha256:9e4b47ac0f5e749cfc618efdf4726269441014ae1d5583e047b452a32e221920 \
+    --hash=sha256:9fb81d2824dff4f2e297a276297e9031f46d2682cafc484f49de182aa5e5df99 \
+    --hash=sha256:a0eabd0a81625049c5df745209dc7fcef6e2aea7793e5f003ba363610aa0a3ff \
+    --hash=sha256:a3d819eb6f9b8677f57f9664265d0a10dd6551d227afb4af2b9cd7bdc2ccbf18 \
+    --hash=sha256:a87de7dd873bf9a792bf1e58b1c3887b9264036629a5bf2d2e6579fe8e73edff \
+    --hash=sha256:aa617107a410245b8660028a7483b68e7914304a6d4882b5ff3d2d3eb5948d8c \
+    --hash=sha256:aac0bbd3e8dd2d9c45ceb82249e8bdd3ac99131a32b4d35c8af3cc9db1657179 \
+    --hash=sha256:ab6dd83b970dc97c2d10bc71aa925b84788c7c05de30241b9e96f9b6d9ea3080 \
+    --hash=sha256:ace2c2326a319a0bb8a8b0e5b570c764962e95818de9f259ce814ee666603f19 \
+    --hash=sha256:ae5fe5c4b525aa82b8076c1a59d642c17b6e8739ecf852522c6321852178119d \
+    --hash=sha256:b11a5d918a6216e521c715b02749240fb07ae5a1fefd4b7bf12f833bc8b4fe70 \
+    --hash=sha256:b1c8c20847b9f34e98080da785bb2336ea982e7f913eed5809e5a3c872900f32 \
+    --hash=sha256:b369d3db3c22ed14c75ccd5af429086f166a19627e84a8fdade3f8f31426e52a \
+    --hash=sha256:b710bc2b8292966b23a6a0121f7a6c51d45d2347edcc75f016ac123b8054d3f2 \
+    --hash=sha256:bd96517ef76c8654446fc3db9242d019a1bb5fe8b751ba414765d59f99210b79 \
+    --hash=sha256:c00f323cc00576df6165cc9d21a4c21285fa6b9989c5c39830c3903dc4303ef3 \
+    --hash=sha256:c162b216070f280fa7da844531169be0baf9ccb17263cf5a8bf876fcd3117fa5 \
+    --hash=sha256:c1a69e58a6bb2de65902051d57fde951febad631a20a64572677a1052690482f \
+    --hash=sha256:c1f794c02903c2824fccce5b20c339a1a14b114e83b306ff11b597c5f71a1c8d \
+    --hash=sha256:c24037349665434f375645fa9d1f5304800cec574d0310f618490c871fd902b3 \
+    --hash=sha256:c300306673aa0f3ed5ed9372b21867690a17dba38c68c44b287437c362ce486b \
+    --hash=sha256:c56a1d43b2f9ee4786e4658c7903f05da35b923fb53c11025712562d5cc02753 \
+    --hash=sha256:c6379f35350b655fd817cd0d6cbeef7f265f3ae5fedb1caae2eb442bbeae9ab9 \
+    --hash=sha256:c802e1c2ed9f0c06a65bc4ed0189d000ada8049312cfeab6ca635e39c9608957 \
+    --hash=sha256:cb83f8a875b3d9b458cada4f880fa498646874ba4011dc974e071a0a84a1b033 \
+    --hash=sha256:cf120cce539453ae086eacc0130a324e7026113510efa83ab42ef3fcfccac7fb \
+    --hash=sha256:dd36439be765e2dde7660212b5275641edbc813e7b24668831a5c8ac91180656 \
+    --hash=sha256:dd5350b55f9fecddc51385463a4f67a5da829bc741e38cf689f38ec9023f54ab \
+    --hash=sha256:df5c7333167b9674aa8ae1d4008fa4bc17a313cc490b2cca27838bbdcc6bb15b \
+    --hash=sha256:e63601ad5cd8f860aa99d109889b5ac34de571c7ee902d6812d5d9ddcc77fa7d \
+    --hash=sha256:e92ce66cd919d18d14b3856906a61d3f6b6a8500e0794142338da644260595cd \
+    --hash=sha256:e99f5507401436fdcc85036a2e7dc2e28d962550afe1cbfc07c40e454256a859 \
+    --hash=sha256:ea2e2f6f801696ad7de8aec061044d6c8c0dd4037608c7cab38a9a4d316bfb11 \
+    --hash=sha256:eafa2c8658f4e560b098fe9fc54539f86528651f61849b22111a9b107d18910c \
+    --hash=sha256:ecd4ad8453ac17bc7ba3868371bffb46f628161ad0eefbd0a855d2c8c32dd81a \
+    --hash=sha256:ee70d08fd60c9565ba8190f41a46a54096afa0eeb8f76bd66f2c25d3b1b83005 \
+    --hash=sha256:eec1bb8cdbba2925bedc887bc0609a80e599c75b12d87ae42ac23fd199445654 \
+    --hash=sha256:ef0c1fe22171dd7c7c27147f2e9c3e86f8bdf473fed75f16b0c2e84a5030ce80 \
+    --hash=sha256:f2901429da1e645ce548bf9171784c0f74f0718c3f6150ce166be39e4dd66c3e \
+    --hash=sha256:f422a209d2455c56849442ae42f25dbaaba1c6c3f501d58761c619c7836642ec \
+    --hash=sha256:f65e5120863c2b266dbcc927b306c5b78e502c71edf3295dfcb9501ec96e5fc7 \
+    --hash=sha256:f7d4a670107d75dfe5ad080bed6c341d18c4442f9378c9f58e5851e86eb79965 \
+    --hash=sha256:f914c03e6a31deb632e2daa881fe198461f4d06e57ac3d0e05bbcab8eae01945 \
+    --hash=sha256:fb66442c2546446944437df74379e9cf9e9db353e61301d1a0e26482f43f0dd8
 markupsafe==2.1.2 ; python_full_version >= "3.8.0" and python_full_version < "4.0.0" \
    --hash=sha256:0576fe974b40a400449768941d5d0858cc624e3249dfd1e0c33674e5c7ca7aed \
    --hash=sha256:085fd3201e7b12809f9e6e9bc1e5c96a368c8523fad5afb02afe3c051ae4afcc \
@ -701,9 +697,9 @@ packaging==24.1 ; python_version >= "3.8" and python_full_version < "4.0.0" \
 parameterized==0.9.0 ; python_full_version >= "3.8.0" and python_full_version < "4.0.0" \
    --hash=sha256:4e0758e3d41bea3bbd05ec14fc2c24736723f243b28d702081aef438c9372b1b \
    --hash=sha256:7fc905272cefa4f364c1a3429cbbe9c0f98b793988efb5bf90aac80f08db09b1
-phonenumbers==8.13.42 ; python_full_version >= "3.8.0" and python_full_version < "4.0.0" \
-    --hash=sha256:18acc22ee03116d27b26e990f53806a1770a3e05f05e1620bc09ad187f889456 \
-    --hash=sha256:7137904f2db3b991701e853174ce8e1cb8f540b8bfdf27617540de04c0b7bed5
+phonenumbers==8.13.43 ; python_full_version >= "3.8.0" and python_full_version < "4.0.0" \
+    --hash=sha256:339e521403fe4dd9c664dbbeb2fe434f9ea5c81e54c0fdfadbaeb53b26a76c27 \
+    --hash=sha256:35b904e4a79226eee027fbb467a9aa6f1ab9ffc3c09c91bf14b885c154936726
 pillow==10.4.0 ; python_version >= "3.8" and python_full_version < "4.0.0" \
    --hash=sha256:02a2be69f9c9b8c1e97cf2713e789d4e398c751ecfd9967c18d0ce304efbf885 \
    --hash=sha256:030abdbe43ee02e0de642aee345efa443740aa4d828bfe8e2eb11922ea6a21ea \
@ -932,9 +928,7 @@ python-multipart==0.0.9 ; python_version >= "3.8" and python_full_version < "4.0
    --hash=sha256:03f54688c663f1b7977105f021043b0793151e4cb1c1a9d4a11fc13d622c4026 \
    --hash=sha256:97ca7b8ea7b05f977dc3849c3ba99d51689822fab725c3703af7c866a0c2b215
 pyyaml==6.0.1 ; python_full_version >= "3.8.0" and python_full_version < "4.0.0" \
-    --hash=sha256:04ac92ad1925b2cff1db0cfebffb6ffc43457495c9b3c39d3fcae417d7125dc5 \
    --hash=sha256:062582fca9fabdd2c8b54a3ef1c978d786e0f6b3a1510e0ac93ef59e0ddae2bc \
-    --hash=sha256:0d3304d8c0adc42be59c5f8a4d9e3d7379e6955ad754aa9d6ab7a398b59dd1df \
    --hash=sha256:1635fd110e8d85d55237ab316b5b011de701ea0f29d07611174a1b42f1444741 \
    --hash=sha256:184c5108a2aca3c5b3d3bf9395d50893a7ab82a38004c8f61c258d4428e80206 \
    --hash=sha256:18aeb1bf9a78867dc38b259769503436b7c72f7a1f1f4c93ff9a17de54319b27 \
@ -942,10 +936,7 @@ pyyaml==6.0.1 ; python_full_version >= "3.8.0" and python_full_version < "4.0.0"
    --hash=sha256:1e2722cc9fbb45d9b87631ac70924c11d3a401b2d7f410cc0e3bbf249f2dca62 \
    --hash=sha256:1fe35611261b29bd1de0070f0b2f47cb6ff71fa6595c077e42bd0c419fa27b98 \
    --hash=sha256:28c119d996beec18c05208a8bd78cbe4007878c6dd15091efb73a30e90539696 \
-    --hash=sha256:326c013efe8048858a6d312ddd31d56e468118ad4cdeda36c719bf5bb6192290 \
-    --hash=sha256:40df9b996c2b73138957fe23a16a4f0ba614f4c0efce1e9406a184b6d07fa3a9 \
    --hash=sha256:42f8152b8dbc4fe7d96729ec2b99c7097d656dc1213a3229ca5383f973a5ed6d \
-    --hash=sha256:49a183be227561de579b4a36efbb21b3eab9651dd81b1858589f796549873dd6 \
    --hash=sha256:4fb147e7a67ef577a588a0e2c17b6db51dda102c71de36f8549b6816a96e1867 \
    --hash=sha256:50550eb667afee136e9a77d6dc71ae76a44df8b3e51e41b77f6de2932bfe0f47 \
    --hash=sha256:510c9deebc5c0225e8c96813043e62b680ba2f9c50a08d3724c7f28a747d1486 \
@ -953,15 +944,11 @@ pyyaml==6.0.1 ; python_full_version >= "3.8.0" and python_full_version < "4.0.0"
    --hash=sha256:596106435fa6ad000c2991a98fa58eeb8656ef2325d7e158344fb33864ed87e3 \
    --hash=sha256:6965a7bc3cf88e5a1c3bd2e0b5c22f8d677dc88a455344035f03399034eb3007 \
    --hash=sha256:69b023b2b4daa7548bcfbd4aa3da05b3a74b772db9e23b982788168117739938 \
-    --hash=sha256:6c22bec3fbe2524cde73d7ada88f6566758a8f7227bfbf93a408a9d86bcc12a0 \
    --hash=sha256:704219a11b772aea0d8ecd7058d0082713c3562b4e271b849ad7dc4a5c90c13c \
    --hash=sha256:7e07cbde391ba96ab58e532ff4803f79c4129397514e1413a7dc761ccd755735 \
    --hash=sha256:81e0b275a9ecc9c0c0c07b4b90ba548307583c125f54d5b6946cfee6360c733d \
-    --hash=sha256:855fb52b0dc35af121542a76b9a84f8d1cd886ea97c84703eaa6d88e37a2ad28 \
-    --hash=sha256:8d4e9c88387b0f5c7d5f281e55304de64cf7f9c0021a3525bd3b1c542da3b0e4 \
    --hash=sha256:9046c58c4395dff28dd494285c82ba00b546adfc7ef001486fbf0324bc174fba \
    --hash=sha256:9eb6caa9a297fc2c2fb8862bc5370d0303ddba53ba97e71f08023b6cd73d16a8 \
-    --hash=sha256:a08c6f0fe150303c1c6b71ebcd7213c2858041a7e01975da3a99aed1e7a378ef \
    --hash=sha256:a0cd17c15d3bb3fa06978b4e8958dcdc6e0174ccea823003a106c7d4d7899ac5 \
    --hash=sha256:afd7e57eddb1a54f0f1a974bc4391af8bcce0b444685d936840f125cf046d5bd \
    --hash=sha256:b1275ad35a5d18c62a7220633c913e1b42d44b46ee12554e5fd39c70a243d6a3 \
@ -974,9 +961,7 @@ pyyaml==6.0.1 ; python_full_version >= "3.8.0" and python_full_version < "4.0.0"
    --hash=sha256:bfdf460b1736c775f2ba9f6a92bca30bc2095067b8a9d77876d1fad6cc3b4a43 \
    --hash=sha256:c8098ddcc2a85b61647b2590f825f3db38891662cfc2fc776415143f599bb859 \
    --hash=sha256:d2b04aac4d386b172d5b9692e2d2da8de7bfb6c387fa4f801fbf6fb2e6ba4673 \
-    --hash=sha256:d483d2cdf104e7c9fa60c544d92981f12ad66a457afae824d146093b8c294c54 \
    --hash=sha256:d858aa552c999bc8a8d57426ed01e40bef403cd8ccdd0fc5f6f04a00414cac2a \
-    --hash=sha256:e7d73685e87afe9f3b36c799222440d6cf362062f78be1013661b00c5c6f678b \
    --hash=sha256:f003ed9ad21d6a4713f0a9b5a7a0a79e08dd0f221aff4525a2be4c346ee60aab \
    --hash=sha256:f22ac1c3cac4dbc50079e965eba2c1058622631e526bd9afd45fedd49ba781fa \
    --hash=sha256:faca3bdcf85b2fc05d06ff3fbc1f83e1391b3e724afa3feba7d13eeab355484c \
@ -1096,9 +1081,9 @@ service-identity==24.1.0 ; python_version >= "3.8" and python_full_version < "4.
 setuptools-rust==1.8.1 ; python_version >= "3.8" and python_full_version < "4.0.0" \
    --hash=sha256:94b1dd5d5308b3138d5b933c3a2b55e6d6927d1a22632e509fcea9ddd0f7e486 \
    --hash=sha256:b5324493949ccd6aa0c03890c5f6b5f02de4512e3ac1697d02e9a6c02b18aa8e
-setuptools==67.6.0 ; python_version >= "3.8" and python_full_version < "4.0.0" \
-    --hash=sha256:2ee892cd5f29f3373097f5a814697e397cf3ce313616df0af11231e2ad118077 \
-    --hash=sha256:b78aaa36f6b90a074c1fa651168723acbf45d14cb1196b6f02c0fd07f17623b2
+setuptools==72.1.0 ; python_version >= "3.8" and python_full_version < "4.0.0" \
+    --hash=sha256:5a03e1860cf56bb6ef48ce186b0e557fdba433237481a9a625176c2831be15d1 \
+    --hash=sha256:8d243eff56d095e5817f796ede6ae32941278f542e0f941867cc05ae52b162ec
 signedjson==1.1.4 ; python_full_version >= "3.8.0" and python_full_version < "4.0.0" \
    --hash=sha256:45569ec54241c65d2403fe3faf7169be5322547706a231e884ca2b427f23d228 \
    --hash=sha256:cd91c56af53f169ef032c62e9c4a3292dc158866933318d0592e3462db3d6492
--- a/scripts-dev/federation_client.py
+++ b/scripts-dev/federation_client.py
@ -43,7 +43,7 @@ import argparse
 import base64
 import json
 import sys
-from typing import Any, Dict, Optional, Tuple
+from typing import Any, Dict, Mapping, Optional, Tuple, Union
 from urllib import parse as urlparse

 import requests
@ -75,7 +75,7 @@ def encode_canonical_json(value: object) -> bytes:
        value,
        # Encode code-points outside of ASCII as UTF-8 rather than \u escapes
        ensure_ascii=False,
-        # Remove unecessary white space.
+        # Remove unnecessary white space.
        separators=(",", ":"),
        # Sort the keys of dictionaries.
        sort_keys=True,
@ -298,12 +298,23 @@ class MatrixConnectionAdapter(HTTPAdapter):

        return super().send(request, *args, **kwargs)

-    def get_connection(
-        self, url: str, proxies: Optional[Dict[str, str]] = None
+    def get_connection_with_tls_context(
+        self,
+        request: PreparedRequest,
+        verify: Optional[Union[bool, str]],
+        proxies: Optional[Mapping[str, str]] = None,
+        cert: Optional[Union[Tuple[str, str], str]] = None,
    ) -> HTTPConnectionPool:
-        # overrides the get_connection() method in the base class
-        parsed = urlparse.urlsplit(url)
-        (host, port, ssl_server_name) = self._lookup(parsed.netloc)
+        # overrides the get_connection_with_tls_context() method in the base class
+        parsed = urlparse.urlsplit(request.url)
+
+        # Extract the server name from the request URL, and ensure it's a str.
+        hostname = parsed.netloc
+        if isinstance(hostname, bytes):
+            hostname = hostname.decode("utf-8")
+        assert isinstance(hostname, str)
+
+        (host, port, ssl_server_name) = self._lookup(hostname)
        print(
            f"Connecting to {host}:{port} with SNI {ssl_server_name}", file=sys.stderr
        )
--- a/scripts-dev/release.py
+++ b/scripts-dev/release.py
@ -324,6 +324,11 @@ def tag(gh_token: Optional[str]) -> None:
 def _tag(gh_token: Optional[str]) -> None:
    """Tags the release and generates a draft GitHub release"""

+    if gh_token:
+        # Test that the GH Token is valid before continuing.
+        gh = Github(gh_token)
+        gh.get_user()
+
    # Make sure we're in a git repo.
    repo = get_repo_and_check_clean_checkout()

@ -418,6 +423,11 @@ def publish(gh_token: str) -> None:
 def _publish(gh_token: str) -> None:
    """Publish release on GitHub."""

+    if gh_token:
+        # Test that the GH Token is valid before continuing.
+        gh = Github(gh_token)
+        gh.get_user()
+
    # Make sure we're in a git repo.
    get_repo_and_check_clean_checkout()

@ -460,6 +470,11 @@ def upload(gh_token: Optional[str]) -> None:
 def _upload(gh_token: Optional[str]) -> None:
    """Upload release to pypi."""

+    if gh_token:
+        # Test that the GH Token is valid before continuing.
+        gh = Github(gh_token)
+        gh.get_user()
+
    current_version = get_package_version()
    tag_name = f"v{current_version}"

@ -555,6 +570,11 @@ def wait_for_actions(gh_token: Optional[str]) -> None:


 def _wait_for_actions(gh_token: Optional[str]) -> None:
+    if gh_token:
+        # Test that the GH Token is valid before continuing.
+        gh = Github(gh_token)
+        gh.get_user()
+
    # Find out the version and tag name.
    current_version = get_package_version()
    tag_name = f"v{current_version}"
@ -711,6 +731,11 @@ Ask the designated people to do the blog and tweets."""
@cli.command()
@click.option("--gh-token", envvar=["GH_TOKEN", "GITHUB_TOKEN"], required=True)
 def full(gh_token: str) -> None:
+    if gh_token:
+        # Test that the GH Token is valid before continuing.
+        gh = Github(gh_token)
+        gh.get_user()
+
    click.echo("1. If this is a security release, read the security wiki page.")
    click.echo("2. Check for any release blockers before proceeding.")
    click.echo("    https://github.com/element-hq/synapse/labels/X-Release-Blocker")
--- a/synapse/api/errors.py
+++ b/synapse/api/errors.py
@ -128,7 +128,7 @@ class Codes(str, Enum):
    # MSC2677
    DUPLICATE_ANNOTATION = "M_DUPLICATE_ANNOTATION"

-    # MSC3575 we are telling the client they need to reset their sliding sync
+    # MSC3575 we are telling the client they need to expire their sliding sync
    # connection.
    UNKNOWN_POS = "M_UNKNOWN_POS"

--- a/synapse/app/generic_worker.py
+++ b/synapse/app/generic_worker.py
@ -206,6 +206,21 @@ class GenericWorkerServer(HomeServer):
                                "/_synapse/admin": admin_resource,
                            }
                        )
+
+                        if "federation" not in res.names:
+                            # Only load the federation media resource separately if federation
+                            # resource is not specified since federation resource includes media
+                            # resource.
+                            resources[FEDERATION_PREFIX] = TransportLayerServer(
+                                self, servlet_groups=["media"]
+                            )
+                        if "client" not in res.names:
+                            # Only load the client media resource separately if client
+                            # resource is not specified since client resource includes media
+                            # resource.
+                            resources[CLIENT_API_PREFIX] = ClientRestResource(
+                                self, servlet_groups=["media"]
+                            )
                    else:
                        logger.warning(
                            "A 'media' listener is configured but the media"
--- a/synapse/app/homeserver.py
+++ b/synapse/app/homeserver.py
@ -101,6 +101,12 @@ class SynapseHomeServer(HomeServer):
                    # Skip loading openid resource if federation is defined
                    # since federation resource will include openid
                    continue
+                if name == "media" and (
+                    "federation" in res.names or "client" in res.names
+                ):
+                    # Skip loading media resource if federation or client are defined
+                    # since federation & client resources will include media
+                    continue
                if name == "health":
                    # Skip loading, health resource is always included
                    continue
@ -231,6 +237,14 @@ class SynapseHomeServer(HomeServer):
                    "'media' resource conflicts with enable_media_repo=False"
                )

+        if name == "media":
+            resources[FEDERATION_PREFIX] = TransportLayerServer(
+                self, servlet_groups=["media"]
+            )
+            resources[CLIENT_API_PREFIX] = ClientRestResource(
+                self, servlet_groups=["media"]
+            )
+
        if name in ["keys", "federation"]:
            resources[SERVER_KEY_PREFIX] = KeyResource(self)

--- a/synapse/crypto/keyring.py
+++ b/synapse/crypto/keyring.py
@ -589,7 +589,7 @@ class BaseV2KeyFetcher(KeyFetcher):
                % (server_name,)
            )

-        for key_id, key_data in response_json["old_verify_keys"].items():
+        for key_id, key_data in response_json.get("old_verify_keys", {}).items():
            if is_signing_algorithm_supported(key_id):
                key_base64 = key_data["key"]
                key_bytes = decode_base64(key_base64)
--- a/synapse/federation/transport/server/init.py
+++ b/synapse/federation/transport/server/init.py
@ -271,6 +271,10 @@ SERVLET_GROUPS: Dict[str, Iterable[Type[BaseFederationServlet]]] = {
    "federation": FEDERATION_SERVLET_CLASSES,
    "room_list": (PublicRoomList,),
    "openid": (OpenIdUserInfo,),
+    "media": (
+        FederationMediaDownloadServlet,
+        FederationMediaThumbnailServlet,
+    ),
 }


--- a/synapse/federation/transport/server/federation.py
+++ b/synapse/federation/transport/server/federation.py
@ -912,6 +912,4 @@ FEDERATION_SERVLET_CLASSES: Tuple[Type[BaseFederationServlet], ...] = (
    FederationV1SendKnockServlet,
    FederationMakeKnockServlet,
    FederationAccountStatusServlet,
-    FederationMediaDownloadServlet,
-    FederationMediaThumbnailServlet,
 )
--- a/synapse/handlers/admin.py
+++ b/synapse/handlers/admin.py
@ -197,8 +197,14 @@ class AdminHandler:
            # events that we have and then filtering, this isn't the most
            # efficient method perhaps but it does guarantee we get everything.
            while True:
-                events, _ = await self._store.paginate_room_events(
-                    room_id, from_key, to_key, limit=100, direction=Direction.FORWARDS
+                events, _ = (
+                    await self._store.paginate_room_events_by_topological_ordering(
+                        room_id=room_id,
+                        from_key=from_key,
+                        to_key=to_key,
+                        limit=100,
+                        direction=Direction.FORWARDS,
+                    )
                )
                if not events:
                    break
--- a/synapse/handlers/device.py
+++ b/synapse/handlers/device.py
@ -20,10 +20,20 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, Dict, Iterable, List, Mapping, Optional, Set, Tuple
+from typing import (
+    TYPE_CHECKING,
+    AbstractSet,
+    Dict,
+    Iterable,
+    List,
+    Mapping,
+    Optional,
+    Set,
+    Tuple,
+)

 from synapse.api import errors
-from synapse.api.constants import EduTypes, EventTypes
+from synapse.api.constants import EduTypes, EventTypes, Membership
 from synapse.api.errors import (
    Codes,
    FederationDeniedError,
@ -38,6 +48,7 @@ from synapse.metrics.background_process_metrics import (
    wrap_as_background_process,
 )
 from synapse.storage.databases.main.client_ips import DeviceLastConnectionInfo
+from synapse.storage.databases.main.state_deltas import StateDelta
 from synapse.types import (
    DeviceListUpdates,
    JsonDict,
@ -222,129 +233,111 @@ class DeviceWorkerHandler:

        set_tag("user_id", user_id)
        set_tag("from_token", str(from_token))
-        now_room_key = self.store.get_room_max_token()

-        room_ids = await self.store.get_rooms_for_user(user_id)
+        now_token = self._event_sources.get_current_token()

-        changed = await self.get_device_changes_in_shared_rooms(
-            user_id, room_ids, from_token
+        # We need to work out all the different membership changes for the user
+        # and user they share a room with, to pass to
+        # `generate_sync_entry_for_device_list`. See its docstring for details
+        # on the data required.
+
+        joined_room_ids = await self.store.get_rooms_for_user(user_id)
+
+        # Get the set of rooms that the user has joined/left
+        membership_changes = (
+            await self.store.get_current_state_delta_membership_changes_for_user(
+                user_id, from_key=from_token.room_key, to_key=now_token.room_key
+            )
        )

-        # Then work out if any users have since joined
-        rooms_changed = self.store.get_rooms_that_changed(room_ids, from_token.room_key)
+        # Check for newly joined or left rooms. We need to make sure that we add
+        # to newly joined in the case membership goes from join -> leave -> join
+        # again.
+        newly_joined_rooms: Set[str] = set()
+        newly_left_rooms: Set[str] = set()
+        for change in membership_changes:
+            # We check for changes in "joinedness", i.e. if the membership has
+            # changed to or from JOIN.
+            if change.membership == Membership.JOIN:
+                if change.prev_membership != Membership.JOIN:
+                    newly_joined_rooms.add(change.room_id)
+                    newly_left_rooms.discard(change.room_id)
+            elif change.prev_membership == Membership.JOIN:
+                newly_joined_rooms.discard(change.room_id)
+                newly_left_rooms.add(change.room_id)

-        member_events = await self.store.get_membership_changes_for_user(
-            user_id, from_token.room_key, now_room_key
+        # We now work out if any other users have since joined or left the rooms
+        # the user is currently in.
+
+        # List of membership changes per room
+        room_to_deltas: Dict[str, List[StateDelta]] = {}
+        # The set of event IDs of membership events (so we can fetch their
+        # associated membership).
+        memberships_to_fetch: Set[str] = set()
+
+        # TODO: Only pull out membership events?
+        state_changes = await self.store.get_current_state_deltas_for_rooms(
+            joined_room_ids, from_token=from_token.room_key, to_token=now_token.room_key
        )
-        rooms_changed.update(event.room_id for event in member_events)
-
-        stream_ordering = from_token.room_key.stream
-
-        possibly_changed = set(changed)
-        possibly_left = set()
-        for room_id in rooms_changed:
-            # Check if the forward extremities have changed. If not then we know
-            # the current state won't have changed, and so we can skip this room.
-            try:
-                if not await self.store.have_room_forward_extremities_changed_since(
-                    room_id, stream_ordering
-                ):
+        for delta in state_changes:
+            if delta.event_type != EventTypes.Member:
                continue
-            except errors.StoreError:
-                pass

-            current_state_ids = await self._state_storage.get_current_state_ids(
-                room_id, await_full_state=False
+            room_to_deltas.setdefault(delta.room_id, []).append(delta)
+            if delta.event_id:
+                memberships_to_fetch.add(delta.event_id)
+            if delta.prev_event_id:
+                memberships_to_fetch.add(delta.prev_event_id)
+
+        # Fetch all the memberships for the membership events
+        event_id_to_memberships = await self.store.get_membership_from_event_ids(
+            memberships_to_fetch
        )

-            # The user may have left the room
-            # TODO: Check if they actually did or if we were just invited.
-            if room_id not in room_ids:
-                for etype, state_key in current_state_ids.keys():
-                    if etype != EventTypes.Member:
-                        continue
-                    possibly_left.add(state_key)
-                continue
-
-            # Fetch the current state at the time.
-            try:
-                event_ids = await self.store.get_forward_extremities_for_room_at_stream_ordering(
-                    room_id, stream_ordering=stream_ordering
-                )
-            except errors.StoreError:
-                # we have purged the stream_ordering index since the stream
-                # ordering: treat it the same as a new room
-                event_ids = []
-
-            # special-case for an empty prev state: include all members
-            # in the changed list
-            if not event_ids:
-                log_kv(
-                    {"event": "encountered empty previous state", "room_id": room_id}
-                )
-                for etype, state_key in current_state_ids.keys():
-                    if etype != EventTypes.Member:
-                        continue
-                    possibly_changed.add(state_key)
-                continue
-
-            current_member_id = current_state_ids.get((EventTypes.Member, user_id))
-            if not current_member_id:
-                continue
-
-            # mapping from event_id -> state_dict
-            prev_state_ids = await self._state_storage.get_state_ids_for_events(
-                event_ids,
-                await_full_state=False,
+        joined_invited_knocked = (
+            Membership.JOIN,
+            Membership.INVITE,
+            Membership.KNOCK,
        )

-            # Check if we've joined the room? If so we just blindly add all the users to
-            # the "possibly changed" users.
-            for state_dict in prev_state_ids.values():
-                member_event = state_dict.get((EventTypes.Member, user_id), None)
-                if not member_event or member_event != current_member_id:
-                    for etype, state_key in current_state_ids.keys():
-                        if etype != EventTypes.Member:
-                            continue
-                        possibly_changed.add(state_key)
-                    break
+        # We now want to find any user that have newly joined/invited/knocked,
+        # or newly left, similarly to above.
+        newly_joined_or_invited_or_knocked_users: Set[str] = set()
+        newly_left_users: Set[str] = set()
+        for _, deltas in room_to_deltas.items():
+            for delta in deltas:
+                # Get the prev/new memberships for the delta
+                new_membership = None
+                prev_membership = None
+                if delta.event_id:
+                    m = event_id_to_memberships.get(delta.event_id)
+                    if m is not None:
+                        new_membership = m.membership
+                if delta.prev_event_id:
+                    m = event_id_to_memberships.get(delta.prev_event_id)
+                    if m is not None:
+                        prev_membership = m.membership

-            # If there has been any change in membership, include them in the
-            # possibly changed list. We'll check if they are joined below,
-            # and we're not toooo worried about spuriously adding users.
-            for key, event_id in current_state_ids.items():
-                etype, state_key = key
-                if etype != EventTypes.Member:
-                    continue
+                # Check if a user has newly joined/invited/knocked, or left.
+                if new_membership in joined_invited_knocked:
+                    if prev_membership not in joined_invited_knocked:
+                        newly_joined_or_invited_or_knocked_users.add(delta.state_key)
+                        newly_left_users.discard(delta.state_key)
+                elif prev_membership in joined_invited_knocked:
+                    newly_joined_or_invited_or_knocked_users.discard(delta.state_key)
+                    newly_left_users.add(delta.state_key)

-                # check if this member has changed since any of the extremities
-                # at the stream_ordering, and add them to the list if so.
-                for state_dict in prev_state_ids.values():
-                    prev_event_id = state_dict.get(key, None)
-                    if not prev_event_id or prev_event_id != event_id:
-                        if state_key != user_id:
-                            possibly_changed.add(state_key)
-                        break
-
-        if possibly_changed or possibly_left:
-            possibly_joined = possibly_changed
-            possibly_left = possibly_changed | possibly_left
-
-            # Double check if we still share rooms with the given user.
-            users_rooms = await self.store.get_rooms_for_users(possibly_left)
-            for changed_user_id, entries in users_rooms.items():
-                if any(rid in room_ids for rid in entries):
-                    possibly_left.discard(changed_user_id)
-                else:
-                    possibly_joined.discard(changed_user_id)
-
-        else:
-            possibly_joined = set()
-            possibly_left = set()
-
-        device_list_updates = DeviceListUpdates(
-            changed=possibly_joined,
-            left=possibly_left,
+        # Now we actually calculate the device list entry with the information
+        # calculated above.
+        device_list_updates = await self.generate_sync_entry_for_device_list(
+            user_id=user_id,
+            since_token=from_token,
+            now_token=now_token,
+            joined_room_ids=joined_room_ids,
+            newly_joined_rooms=newly_joined_rooms,
+            newly_joined_or_invited_or_knocked_users=newly_joined_or_invited_or_knocked_users,
+            newly_left_rooms=newly_left_rooms,
+            newly_left_users=newly_left_users,
        )

        log_kv(
@ -356,6 +349,88 @@ class DeviceWorkerHandler:

        return device_list_updates

+    @measure_func("_generate_sync_entry_for_device_list")
+    async def generate_sync_entry_for_device_list(
+        self,
+        user_id: str,
+        since_token: StreamToken,
+        now_token: StreamToken,
+        joined_room_ids: AbstractSet[str],
+        newly_joined_rooms: AbstractSet[str],
+        newly_joined_or_invited_or_knocked_users: AbstractSet[str],
+        newly_left_rooms: AbstractSet[str],
+        newly_left_users: AbstractSet[str],
+    ) -> DeviceListUpdates:
+        """Generate the DeviceListUpdates section of sync
+
+        Args:
+            sync_result_builder
+            newly_joined_rooms: Set of rooms user has joined since previous sync
+            newly_joined_or_invited_or_knocked_users: Set of users that have joined,
+                been invited to a room or are knocking on a room since
+                previous sync.
+            newly_left_rooms: Set of rooms user has left since previous sync
+            newly_left_users: Set of users that have left a room we're in since
+                previous sync
+        """
+        # Take a copy since these fields will be mutated later.
+        newly_joined_or_invited_or_knocked_users = set(
+            newly_joined_or_invited_or_knocked_users
+        )
+        newly_left_users = set(newly_left_users)
+
+        # We want to figure out what user IDs the client should refetch
+        # device keys for, and which users we aren't going to track changes
+        # for anymore.
+        #
+        # For the first step we check:
+        #   a. if any users we share a room with have updated their devices,
+        #      and
+        #   b. we also check if we've joined any new rooms, or if a user has
+        #      joined a room we're in.
+        #
+        # For the second step we just find any users we no longer share a
+        # room with by looking at all users that have left a room plus users
+        # that were in a room we've left.
+
+        users_that_have_changed = set()
+
+        # Step 1a, check for changes in devices of users we share a room
+        # with
+        users_that_have_changed = await self.get_device_changes_in_shared_rooms(
+            user_id,
+            joined_room_ids,
+            from_token=since_token,
+            now_token=now_token,
+        )
+
+        # Step 1b, check for newly joined rooms
+        for room_id in newly_joined_rooms:
+            joined_users = await self.store.get_users_in_room(room_id)
+            newly_joined_or_invited_or_knocked_users.update(joined_users)
+
+        # TODO: Check that these users are actually new, i.e. either they
+        # weren't in the previous sync *or* they left and rejoined.
+        users_that_have_changed.update(newly_joined_or_invited_or_knocked_users)
+
+        user_signatures_changed = await self.store.get_users_whose_signatures_changed(
+            user_id, since_token.device_list_key
+        )
+        users_that_have_changed.update(user_signatures_changed)
+
+        # Now find users that we no longer track
+        for room_id in newly_left_rooms:
+            left_users = await self.store.get_users_in_room(room_id)
+            newly_left_users.update(left_users)
+
+        # Remove any users that we still share a room with.
+        left_users_rooms = await self.store.get_rooms_for_users(newly_left_users)
+        for user_id, entries in left_users_rooms.items():
+            if any(rid in joined_room_ids for rid in entries):
+                newly_left_users.discard(user_id)
+
+        return DeviceListUpdates(changed=users_that_have_changed, left=newly_left_users)
+
    async def on_federation_query_user_devices(self, user_id: str) -> JsonDict:
        if not self.hs.is_mine(UserID.from_string(user_id)):
            raise SynapseError(400, "User is not hosted on this homeserver")
--- a/synapse/handlers/pagination.py
+++ b/synapse/handlers/pagination.py
@ -507,7 +507,8 @@ class PaginationHandler:

        # Initially fetch the events from the database. With any luck, we can return
        # these without blocking on backfill (handled below).
-        events, next_key = await self.store.paginate_room_events(
+        events, next_key = (
+            await self.store.paginate_room_events_by_topological_ordering(
                room_id=room_id,
                from_key=from_token.room_key,
                to_key=to_room_key,
@ -515,6 +516,7 @@ class PaginationHandler:
                limit=pagin_config.limit,
                event_filter=event_filter,
            )
+        )

        if pagin_config.direction == Direction.BACKWARDS:
            # We use a `Set` because there can be multiple events at a given depth
@ -582,7 +584,8 @@ class PaginationHandler:
                # If we did backfill something, refetch the events from the database to
                # catch anything new that might have been added since we last fetched.
                if did_backfill:
-                    events, next_key = await self.store.paginate_room_events(
+                    events, next_key = (
+                        await self.store.paginate_room_events_by_topological_ordering(
                            room_id=room_id,
                            from_key=from_token.room_key,
                            to_key=to_room_key,
@ -590,6 +593,7 @@ class PaginationHandler:
                            limit=pagin_config.limit,
                            event_filter=event_filter,
                        )
+                    )
            else:
                # Otherwise, we can backfill in the background for eventual
                # consistency's sake but we don't need to block the client waiting
--- a/synapse/handlers/profile.py
+++ b/synapse/handlers/profile.py
@ -74,6 +74,17 @@ class ProfileHandler:
        self._third_party_rules = hs.get_module_api_callbacks().third_party_event_rules

    async def get_profile(self, user_id: str, ignore_backoff: bool = True) -> JsonDict:
+        """
+        Get a user's profile as a JSON dictionary.
+
+        Args:
+            user_id: The user to fetch the profile of.
+            ignore_backoff: True to ignore backoff when fetching over federation.
+
+        Returns:
+            A JSON dictionary. For local queries this will include the displayname and avatar_url
+            fields. For remote queries it may contain arbitrary information.
+        """
        target_user = UserID.from_string(user_id)

        if self.hs.is_mine(target_user):
@ -107,6 +118,15 @@ class ProfileHandler:
                raise e.to_synapse_error()

    async def get_displayname(self, target_user: UserID) -> Optional[str]:
+        """
+        Fetch a user's display name from their profile.
+
+        Args:
+            target_user: The user to fetch the display name of.
+
+        Returns:
+            The user's display name or None if unset.
+        """
        if self.hs.is_mine(target_user):
            try:
                displayname = await self.store.get_profile_displayname(target_user)
@ -203,6 +223,15 @@ class ProfileHandler:
            await self._update_join_states(requester, target_user)

    async def get_avatar_url(self, target_user: UserID) -> Optional[str]:
+        """
+        Fetch a user's avatar URL from their profile.
+
+        Args:
+            target_user: The user to fetch the avatar URL of.
+
+        Returns:
+            The user's avatar URL or None if unset.
+        """
        if self.hs.is_mine(target_user):
            try:
                avatar_url = await self.store.get_profile_avatar_url(target_user)
@ -403,6 +432,12 @@ class ProfileHandler:
    async def _update_join_states(
        self, requester: Requester, target_user: UserID
    ) -> None:
+        """
+        Update the membership events of each room the user is joined to with the
+        new profile information.
+
+        Note that this stomps over any custom display name or avatar URL in member events.
+        """
        if not self.hs.is_mine(target_user):
            return

--- a/synapse/handlers/room.py
+++ b/synapse/handlers/room.py
@ -1762,7 +1762,7 @@ class RoomEventSource(EventSource[RoomStreamToken, EventBase]):
                from_key=from_key,
                to_key=to_key,
                limit=limit or 10,
-                order="ASC",
+                direction=Direction.FORWARDS,
            )

            events = list(room_events)
--- a/synapse/handlers/sliding_sync.py
+++ b/synapse/handlers/sliding_sync.py
--- a/synapse/handlers/sync.py
+++ b/synapse/handlers/sync.py
@ -43,6 +43,7 @@ from prometheus_client import Counter

 from synapse.api.constants import (
    AccountDataTypes,
+    Direction,
    EventContentFields,
    EventTypes,
    JoinRules,
@ -64,6 +65,7 @@ from synapse.logging.opentracing import (
 )
 from synapse.storage.databases.main.event_push_actions import RoomNotifCounts
 from synapse.storage.databases.main.roommember import extract_heroes_from_room_summary
+from synapse.storage.databases.main.stream import PaginateFunction
 from synapse.storage.roommember import MemberSummary
 from synapse.types import (
    DeviceListUpdates,
@ -84,7 +86,7 @@ from synapse.util.async_helpers import concurrently_execute
 from synapse.util.caches.expiringcache import ExpiringCache
 from synapse.util.caches.lrucache import LruCache
 from synapse.util.caches.response_cache import ResponseCache, ResponseCacheContext
-from synapse.util.metrics import Measure, measure_func
+from synapse.util.metrics import Measure
 from synapse.visibility import filter_events_for_client

 if TYPE_CHECKING:
@ -879,22 +881,49 @@ class SyncHandler:
                since_key = since_token.room_key

            while limited and len(recents) < timeline_limit and max_repeat:
-                # If we have a since_key then we are trying to get any events
-                # that have happened since `since_key` up to `end_key`, so we
-                # can just use `get_room_events_stream_for_room`.
-                # Otherwise, we want to return the last N events in the room
-                # in topological ordering.
-                if since_key:
-                    events, end_key = await self.store.get_room_events_stream_for_room(
-                        room_id,
+                # For initial `/sync`, we want to view a historical section of the
+                # timeline; to fetch events by `topological_ordering` (best
+                # representation of the room DAG as others were seeing it at the time).
+                # This also aligns with the order that `/messages` returns events in.
+                #
+                # For incremental `/sync`, we want to get all updates for rooms since
+                # the last `/sync` (regardless if those updates arrived late or happened
+                # a while ago in the past); to fetch events by `stream_ordering` (in the
+                # order they were received by the server).
+                #
+                # Relevant spec issue: https://github.com/matrix-org/matrix-spec/issues/1917
+                #
+                # FIXME: Using workaround for mypy,
+                # https://github.com/python/mypy/issues/10740#issuecomment-1997047277 and
+                # https://github.com/python/mypy/issues/17479
+                paginate_room_events_by_topological_ordering: PaginateFunction = (
+                    self.store.paginate_room_events_by_topological_ordering
+                )
+                paginate_room_events_by_stream_ordering: PaginateFunction = (
+                    self.store.paginate_room_events_by_stream_ordering
+                )
+                pagination_method: PaginateFunction = (
+                    # Use `topographical_ordering` for historical events
+                    paginate_room_events_by_topological_ordering
+                    if since_key is None
+                    # Use `stream_ordering` for updates
+                    else paginate_room_events_by_stream_ordering
+                )
+                events, end_key = await pagination_method(
+                    room_id=room_id,
+                    # The bounds are reversed so we can paginate backwards
+                    # (from newer to older events) starting at to_bound.
+                    # This ensures we fill the `limit` with the newest events first,
+                    from_key=end_key,
+                    to_key=since_key,
+                    direction=Direction.BACKWARDS,
+                    # We add one so we can determine if there are enough events to saturate
+                    # the limit or not (see `limited`)
                    limit=load_limit + 1,
-                        from_key=since_key,
-                        to_key=end_key,
-                    )
-                else:
-                    events, end_key = await self.store.get_recent_events_for_room(
-                        room_id, limit=load_limit + 1, end_token=end_key
                )
+                # We want to return the events in ascending order (the last event is the
+                # most recent).
+                events.reverse()

                log_kv({"loaded_recents": len(events)})

@ -1749,8 +1778,15 @@ class SyncHandler:
                    )

                if include_device_list_updates:
-                    device_lists = await self._generate_sync_entry_for_device_list(
-                        sync_result_builder,
+                    # include_device_list_updates can only be True if we have a
+                    # since token.
+                    assert since_token is not None
+
+                    device_lists = await self._device_handler.generate_sync_entry_for_device_list(
+                        user_id=user_id,
+                        since_token=since_token,
+                        now_token=sync_result_builder.now_token,
+                        joined_room_ids=sync_result_builder.joined_room_ids,
                        newly_joined_rooms=newly_joined_rooms,
                        newly_joined_or_invited_or_knocked_users=newly_joined_or_invited_or_knocked_users,
                        newly_left_rooms=newly_left_rooms,
@ -1862,8 +1898,14 @@ class SyncHandler:
                newly_left_users,
            ) = sync_result_builder.calculate_user_changes()

-            device_lists = await self._generate_sync_entry_for_device_list(
-                sync_result_builder,
+            # include_device_list_updates can only be True if we have a
+            # since token.
+            assert since_token is not None
+            device_lists = await self._device_handler.generate_sync_entry_for_device_list(
+                user_id=user_id,
+                since_token=since_token,
+                now_token=sync_result_builder.now_token,
+                joined_room_ids=sync_result_builder.joined_room_ids,
                newly_joined_rooms=newly_joined_rooms,
                newly_joined_or_invited_or_knocked_users=newly_joined_or_invited_or_knocked_users,
                newly_left_rooms=newly_left_rooms,
@ -2040,94 +2082,6 @@ class SyncHandler:

        return sync_result_builder

-    @measure_func("_generate_sync_entry_for_device_list")
-    async def _generate_sync_entry_for_device_list(
-        self,
-        sync_result_builder: "SyncResultBuilder",
-        newly_joined_rooms: AbstractSet[str],
-        newly_joined_or_invited_or_knocked_users: AbstractSet[str],
-        newly_left_rooms: AbstractSet[str],
-        newly_left_users: AbstractSet[str],
-    ) -> DeviceListUpdates:
-        """Generate the DeviceListUpdates section of sync
-
-        Args:
-            sync_result_builder
-            newly_joined_rooms: Set of rooms user has joined since previous sync
-            newly_joined_or_invited_or_knocked_users: Set of users that have joined,
-                been invited to a room or are knocking on a room since
-                previous sync.
-            newly_left_rooms: Set of rooms user has left since previous sync
-            newly_left_users: Set of users that have left a room we're in since
-                previous sync
-        """
-
-        user_id = sync_result_builder.sync_config.user.to_string()
-        since_token = sync_result_builder.since_token
-        assert since_token is not None
-
-        # Take a copy since these fields will be mutated later.
-        newly_joined_or_invited_or_knocked_users = set(
-            newly_joined_or_invited_or_knocked_users
-        )
-        newly_left_users = set(newly_left_users)
-
-        # We want to figure out what user IDs the client should refetch
-        # device keys for, and which users we aren't going to track changes
-        # for anymore.
-        #
-        # For the first step we check:
-        #   a. if any users we share a room with have updated their devices,
-        #      and
-        #   b. we also check if we've joined any new rooms, or if a user has
-        #      joined a room we're in.
-        #
-        # For the second step we just find any users we no longer share a
-        # room with by looking at all users that have left a room plus users
-        # that were in a room we've left.
-
-        users_that_have_changed = set()
-
-        joined_room_ids = sync_result_builder.joined_room_ids
-
-        # Step 1a, check for changes in devices of users we share a room
-        # with
-        users_that_have_changed = (
-            await self._device_handler.get_device_changes_in_shared_rooms(
-                user_id,
-                joined_room_ids,
-                from_token=since_token,
-                now_token=sync_result_builder.now_token,
-            )
-        )
-
-        # Step 1b, check for newly joined rooms
-        for room_id in newly_joined_rooms:
-            joined_users = await self.store.get_users_in_room(room_id)
-            newly_joined_or_invited_or_knocked_users.update(joined_users)
-
-        # TODO: Check that these users are actually new, i.e. either they
-        # weren't in the previous sync *or* they left and rejoined.
-        users_that_have_changed.update(newly_joined_or_invited_or_knocked_users)
-
-        user_signatures_changed = await self.store.get_users_whose_signatures_changed(
-            user_id, since_token.device_list_key
-        )
-        users_that_have_changed.update(user_signatures_changed)
-
-        # Now find users that we no longer track
-        for room_id in newly_left_rooms:
-            left_users = await self.store.get_users_in_room(room_id)
-            newly_left_users.update(left_users)
-
-        # Remove any users that we still share a room with.
-        left_users_rooms = await self.store.get_rooms_for_users(newly_left_users)
-        for user_id, entries in left_users_rooms.items():
-            if any(rid in joined_room_ids for rid in entries):
-                newly_left_users.discard(user_id)
-
-        return DeviceListUpdates(changed=users_that_have_changed, left=newly_left_users)
-
    @trace
    async def _generate_sync_entry_for_to_device(
        self, sync_result_builder: "SyncResultBuilder"
@ -2640,9 +2594,10 @@ class SyncHandler:
        # a "gap" in the timeline, as described by the spec for /sync.
        room_to_events = await self.store.get_room_events_stream_for_rooms(
            room_ids=sync_result_builder.joined_room_ids,
-            from_key=since_token.room_key,
-            to_key=now_token.room_key,
+            from_key=now_token.room_key,
+            to_key=since_token.room_key,
            limit=timeline_limit + 1,
+            direction=Direction.BACKWARDS,
        )

        # We loop through all room ids, even if there are no new events, in case
@ -2653,6 +2608,9 @@ class SyncHandler:
            newly_joined = room_id in newly_joined_rooms
            if room_entry:
                events, start_key = room_entry
+                # We want to return the events in ascending order (the last event is the
+                # most recent).
+                events.reverse()

                prev_batch_token = now_token.copy_and_replace(
                    StreamKeyType.ROOM, start_key
--- a/synapse/http/client.py
+++ b/synapse/http/client.py
@ -1057,11 +1057,11 @@ class _MultipartParserProtocol(protocol.Protocol):
        if not self.parser:

            def on_header_field(data: bytes, start: int, end: int) -> None:
-                if data[start:end] == b"Location":
+                if data[start:end].lower() == b"location":
                    self.has_redirect = True
-                if data[start:end] == b"Content-Disposition":
+                if data[start:end].lower() == b"content-disposition":
                    self.in_disposition = True
-                if data[start:end] == b"Content-Type":
+                if data[start:end].lower() == b"content-type":
                    self.in_content_type = True

            def on_header_value(data: bytes, start: int, end: int) -> None:
@ -1088,7 +1088,6 @@ class _MultipartParserProtocol(protocol.Protocol):
                    return
                # otherwise we are in the file part
                else:
-                    logger.info("Writing multipart file data to stream")
                    try:
                        self.stream.write(data[start:end])
                    except Exception as e:
--- a/synapse/http/server.py
+++ b/synapse/http/server.py
@ -74,7 +74,6 @@ from synapse.api.errors import (
 from synapse.config.homeserver import HomeServerConfig
 from synapse.logging.context import defer_to_thread, preserve_fn, run_in_background
 from synapse.logging.opentracing import active_span, start_active_span, trace_servlet
-from synapse.types import ISynapseReactor
 from synapse.util import json_encoder
 from synapse.util.caches import intern_dict
 from synapse.util.cancellation import is_function_cancellable
@ -869,8 +868,7 @@ async def _async_write_json_to_request_in_thread(

    with start_active_span("encode_json_response"):
        span = active_span()
-        reactor: ISynapseReactor = request.reactor  # type: ignore
-        json_str = await defer_to_thread(reactor, encode, span)
+        json_str = await defer_to_thread(request.reactor, encode, span)

    _write_bytes_to_request(request, json_str)

--- a/synapse/http/site.py
+++ b/synapse/http/site.py
@ -658,7 +658,7 @@ class SynapseSite(ProxySite):
        )

        self.site_tag = site_tag
-        self.reactor = reactor
+        self.reactor: ISynapseReactor = reactor

        assert config.http_options is not None
        proxied = config.http_options.x_forwarded
--- a/synapse/media/_base.py
+++ b/synapse/media/_base.py
@ -28,6 +28,7 @@ from types import TracebackType
 from typing import (
    TYPE_CHECKING,
    Awaitable,
+    BinaryIO,
    Dict,
    Generator,
    List,
@ -37,19 +38,28 @@ from typing import (
 )

 import attr
+from zope.interface import implementer

+from twisted.internet import interfaces
+from twisted.internet.defer import Deferred
 from twisted.internet.interfaces import IConsumer
-from twisted.protocols.basic import FileSender
+from twisted.python.failure import Failure
 from twisted.web.server import Request

 from synapse.api.errors import Codes, cs_error
 from synapse.http.server import finish_request, respond_with_json
 from synapse.http.site import SynapseRequest
-from synapse.logging.context import make_deferred_yieldable
+from synapse.logging.context import (
+    defer_to_threadpool,
+    make_deferred_yieldable,
+    run_in_background,
+)
 from synapse.util import Clock
+from synapse.util.async_helpers import DeferredEvent
 from synapse.util.stringutils import is_ascii

 if TYPE_CHECKING:
+    from synapse.server import HomeServer
    from synapse.storage.databases.main.media_repository import LocalMedia


@ -123,6 +133,7 @@ def respond_404(request: SynapseRequest) -> None:


 async def respond_with_file(
+    hs: "HomeServer",
    request: SynapseRequest,
    media_type: str,
    file_path: str,
@ -139,7 +150,7 @@ async def respond_with_file(
        add_file_headers(request, media_type, file_size, upload_name)

        with open(file_path, "rb") as f:
-            await make_deferred_yieldable(FileSender().beginFileTransfer(f, request))
+            await ThreadedFileSender(hs).beginFileTransfer(f, request)

        finish_request(request)
    else:
@ -604,3 +615,151 @@ def _parseparam(s: bytes) -> Generator[bytes, None, None]:
        f = s[:end]
        yield f.strip()
        s = s[end:]
+
+
+@implementer(interfaces.IPushProducer)
+class ThreadedFileSender:
+    """
+    A producer that sends the contents of a file to a consumer, reading from the
+    file on a thread.
+
+    This works by having a loop in a threadpool repeatedly reading from the
+    file, until the consumer pauses the producer. There is then a loop in the
+    main thread that waits until the consumer resumes the producer and then
+    starts reading in the threadpool again.
+
+    This is done to ensure that we're never waiting in the threadpool, as
+    otherwise its easy to starve it of threads.
+    """
+
+    # How much data to read in one go.
+    CHUNK_SIZE = 2**14
+
+    # How long we wait for the consumer to be ready again before aborting the
+    # read.
+    TIMEOUT_SECONDS = 90.0
+
+    def __init__(self, hs: "HomeServer") -> None:
+        self.reactor = hs.get_reactor()
+        self.thread_pool = hs.get_media_sender_thread_pool()
+
+        self.file: Optional[BinaryIO] = None
+        self.deferred: "Deferred[None]" = Deferred()
+        self.consumer: Optional[interfaces.IConsumer] = None
+
+        # Signals if the thread should keep reading/sending data. Set means
+        # continue, clear means pause.
+        self.wakeup_event = DeferredEvent(self.reactor)
+
+        # Signals if the thread should terminate, e.g. because the consumer has
+        # gone away.
+        self.stop_writing = False
+
+    def beginFileTransfer(
+        self, file: BinaryIO, consumer: interfaces.IConsumer
+    ) -> "Deferred[None]":
+        """
+        Begin transferring a file
+        """
+        self.file = file
+        self.consumer = consumer
+
+        self.consumer.registerProducer(self, True)
+
+        # We set the wakeup signal as we should start producing immediately.
+        self.wakeup_event.set()
+        run_in_background(self.start_read_loop)
+
+        return make_deferred_yieldable(self.deferred)
+
+    def resumeProducing(self) -> None:
+        """interfaces.IPushProducer"""
+        self.wakeup_event.set()
+
+    def pauseProducing(self) -> None:
+        """interfaces.IPushProducer"""
+        self.wakeup_event.clear()
+
+    def stopProducing(self) -> None:
+        """interfaces.IPushProducer"""
+
+        # Unregister the consumer so we don't try and interact with it again.
+        if self.consumer:
+            self.consumer.unregisterProducer()
+
+        self.consumer = None
+
+        # Terminate the loop.
+        self.stop_writing = True
+        self.wakeup_event.set()
+
+        if not self.deferred.called:
+            self.deferred.errback(Exception("Consumer asked us to stop producing"))
+
+    async def start_read_loop(self) -> None:
+        """This is the loop that drives reading/writing"""
+        try:
+            while not self.stop_writing:
+                # Start the loop in the threadpool to read data.
+                more_data = await defer_to_threadpool(
+                    self.reactor, self.thread_pool, self._on_thread_read_loop
+                )
+                if not more_data:
+                    # Reached EOF, we can just return.
+                    return
+
+                if not self.wakeup_event.is_set():
+                    ret = await self.wakeup_event.wait(self.TIMEOUT_SECONDS)
+                    if not ret:
+                        raise Exception("Timed out waiting to resume")
+        except Exception:
+            self._error(Failure())
+        finally:
+            self._finish()
+
+    def _on_thread_read_loop(self) -> bool:
+        """This is the loop that happens on a thread.
+
+        Returns:
+            Whether there is more data to send.
+        """
+
+        while not self.stop_writing and self.wakeup_event.is_set():
+            # The file should always have been set before we get here.
+            assert self.file is not None
+
+            chunk = self.file.read(self.CHUNK_SIZE)
+            if not chunk:
+                return False
+
+            self.reactor.callFromThread(self._write, chunk)
+
+        return True
+
+    def _write(self, chunk: bytes) -> None:
+        """Called from the thread to write a chunk of data"""
+        if self.consumer:
+            self.consumer.write(chunk)
+
+    def _error(self, failure: Failure) -> None:
+        """Called when there was a fatal error"""
+        if self.consumer:
+            self.consumer.unregisterProducer()
+            self.consumer = None
+
+        if not self.deferred.called:
+            self.deferred.errback(failure)
+
+    def _finish(self) -> None:
+        """Called when we have finished writing (either on success or
+        failure)."""
+        if self.file:
+            self.file.close()
+            self.file = None
+
+        if self.consumer:
+            self.consumer.unregisterProducer()
+            self.consumer = None
+
+        if not self.deferred.called:
+            self.deferred.callback(None)
--- a/synapse/media/media_storage.py
+++ b/synapse/media/media_storage.py
@ -49,15 +49,11 @@ from zope.interface import implementer
 from twisted.internet import interfaces
 from twisted.internet.defer import Deferred
 from twisted.internet.interfaces import IConsumer
-from twisted.protocols.basic import FileSender

 from synapse.api.errors import NotFoundError
-from synapse.logging.context import (
-    defer_to_thread,
-    make_deferred_yieldable,
-    run_in_background,
-)
+from synapse.logging.context import defer_to_thread, run_in_background
 from synapse.logging.opentracing import start_active_span, trace, trace_with_opname
+from synapse.media._base import ThreadedFileSender
 from synapse.util import Clock
 from synapse.util.file_consumer import BackgroundFileConsumer

@ -213,7 +209,7 @@ class MediaStorage:
            local_path = os.path.join(self.local_media_directory, path)
            if os.path.exists(local_path):
                logger.debug("responding with local file %s", local_path)
-                return FileResponder(open(local_path, "rb"))
+                return FileResponder(self.hs, open(local_path, "rb"))
            logger.debug("local file %s did not exist", local_path)

        for provider in self.storage_providers:
@ -336,13 +332,12 @@ class FileResponder(Responder):
            is closed when finished streaming.
    """

-    def __init__(self, open_file: IO):
+    def __init__(self, hs: "HomeServer", open_file: BinaryIO):
+        self.hs = hs
        self.open_file = open_file

    def write_to_consumer(self, consumer: IConsumer) -> Deferred:
-        return make_deferred_yieldable(
-            FileSender().beginFileTransfer(self.open_file, consumer)
-        )
+        return ThreadedFileSender(self.hs).beginFileTransfer(self.open_file, consumer)

    def __exit__(
        self,
@ -549,7 +544,7 @@ class MultipartFileConsumer:
        Calculate the content length of the multipart response
        in bytes.
        """
-        if not self.length:
+        if self.length is None:
            return None
        # calculate length of json field and content-type, disposition headers
        json_field = json.dumps(self.json_field)
--- a/synapse/media/storage_provider.py
+++ b/synapse/media/storage_provider.py
@ -145,6 +145,7 @@ class FileStorageProviderBackend(StorageProvider):

    def __init__(self, hs: "HomeServer", config: str):
        self.hs = hs
+        self.reactor = hs.get_reactor()
        self.cache_directory = hs.config.media.media_store_path
        self.base_directory = config

@ -165,7 +166,7 @@ class FileStorageProviderBackend(StorageProvider):
        shutil_copyfile: Callable[[str, str], str] = shutil.copyfile
        with start_active_span("shutil_copyfile"):
            await defer_to_thread(
-                self.hs.get_reactor(),
+                self.reactor,
                shutil_copyfile,
                primary_fname,
                backup_fname,
@ -177,7 +178,7 @@ class FileStorageProviderBackend(StorageProvider):

        backup_fname = os.path.join(self.base_directory, path)
        if os.path.isfile(backup_fname):
-            return FileResponder(open(backup_fname, "rb"))
+            return FileResponder(self.hs, open(backup_fname, "rb"))

        return None

--- a/synapse/media/thumbnailer.py
+++ b/synapse/media/thumbnailer.py
@ -259,6 +259,7 @@ class ThumbnailProvider:
        media_storage: MediaStorage,
    ):
        self.hs = hs
+        self.reactor = hs.get_reactor()
        self.media_repo = media_repo
        self.media_storage = media_storage
        self.store = hs.get_datastores().main
@ -373,11 +374,11 @@ class ThumbnailProvider:
                await respond_with_multipart_responder(
                    self.hs.get_clock(),
                    request,
-                    FileResponder(open(file_path, "rb")),
+                    FileResponder(self.hs, open(file_path, "rb")),
                    media_info,
                )
            else:
-                await respond_with_file(request, desired_type, file_path)
+                await respond_with_file(self.hs, request, desired_type, file_path)
        else:
            logger.warning("Failed to generate thumbnail")
            raise SynapseError(400, "Failed to generate thumbnail.")
@ -455,7 +456,7 @@ class ThumbnailProvider:
        )

        if file_path:
-            await respond_with_file(request, desired_type, file_path)
+            await respond_with_file(self.hs, request, desired_type, file_path)
        else:
            logger.warning("Failed to generate thumbnail")
            raise SynapseError(400, "Failed to generate thumbnail.")
--- a/synapse/rest/init.py
+++ b/synapse/rest/init.py
@ -18,7 +18,8 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import TYPE_CHECKING, Callable
+import logging
+from typing import TYPE_CHECKING, Callable, Dict, Iterable, List, Optional, Tuple

 from synapse.http.server import HttpServer, JsonResource
 from synapse.rest import admin
@ -67,11 +68,64 @@ from synapse.rest.client import (
    voip,
 )

+logger = logging.getLogger(__name__)
+
 if TYPE_CHECKING:
    from synapse.server import HomeServer

 RegisterServletsFunc = Callable[["HomeServer", HttpServer], None]

+CLIENT_SERVLET_FUNCTIONS: Tuple[RegisterServletsFunc, ...] = (
+    versions.register_servlets,
+    initial_sync.register_servlets,
+    room.register_deprecated_servlets,
+    events.register_servlets,
+    room.register_servlets,
+    login.register_servlets,
+    profile.register_servlets,
+    presence.register_servlets,
+    directory.register_servlets,
+    voip.register_servlets,
+    pusher.register_servlets,
+    push_rule.register_servlets,
+    logout.register_servlets,
+    sync.register_servlets,
+    filter.register_servlets,
+    account.register_servlets,
+    register.register_servlets,
+    auth.register_servlets,
+    receipts.register_servlets,
+    read_marker.register_servlets,
+    room_keys.register_servlets,
+    keys.register_servlets,
+    tokenrefresh.register_servlets,
+    tags.register_servlets,
+    account_data.register_servlets,
+    reporting.register_servlets,
+    openid.register_servlets,
+    notifications.register_servlets,
+    devices.register_servlets,
+    thirdparty.register_servlets,
+    sendtodevice.register_servlets,
+    user_directory.register_servlets,
+    room_upgrade_rest_servlet.register_servlets,
+    capabilities.register_servlets,
+    account_validity.register_servlets,
+    relations.register_servlets,
+    password_policy.register_servlets,
+    knock.register_servlets,
+    appservice_ping.register_servlets,
+    admin.register_servlets_for_client_rest_resource,
+    mutual_rooms.register_servlets,
+    login_token_request.register_servlets,
+    rendezvous.register_servlets,
+    auth_issuer.register_servlets,
+)
+
+SERVLET_GROUPS: Dict[str, Iterable[RegisterServletsFunc]] = {
+    "client": CLIENT_SERVLET_FUNCTIONS,
+}
+

 class ClientRestResource(JsonResource):
    """Matrix Client API REST resource.
@ -83,80 +137,56 @@ class ClientRestResource(JsonResource):
       * etc
    """

-    def __init__(self, hs: "HomeServer"):
+    def __init__(self, hs: "HomeServer", servlet_groups: Optional[List[str]] = None):
        JsonResource.__init__(self, hs, canonical_json=False)
-        self.register_servlets(self, hs)
+        if hs.config.media.can_load_media_repo:
+            # This import is here to prevent a circular import failure
+            from synapse.rest.client import media
+
+            SERVLET_GROUPS["media"] = (media.register_servlets,)
+        self.register_servlets(self, hs, servlet_groups)

    @staticmethod
-    def register_servlets(client_resource: HttpServer, hs: "HomeServer") -> None:
+    def register_servlets(
+        client_resource: HttpServer,
+        hs: "HomeServer",
+        servlet_groups: Optional[Iterable[str]] = None,
+    ) -> None:
        # Some servlets are only registered on the main process (and not worker
        # processes).
        is_main_process = hs.config.worker.worker_app is None

-        versions.register_servlets(hs, client_resource)
+        if not servlet_groups:
+            servlet_groups = SERVLET_GROUPS.keys()

-        # Deprecated in r0
-        initial_sync.register_servlets(hs, client_resource)
-        room.register_deprecated_servlets(hs, client_resource)
+        for servlet_group in servlet_groups:
+            # Fail on unknown servlet groups.
+            if servlet_group not in SERVLET_GROUPS:
+                if servlet_group == "media":
+                    logger.warn(
+                        "media.can_load_media_repo needs to be configured for the media servlet to be available"
+                    )
+                raise RuntimeError(
+                    f"Attempting to register unknown client servlet: '{servlet_group}'"
+                )

-        # Partially deprecated in r0
-        events.register_servlets(hs, client_resource)
+            for servletfunc in SERVLET_GROUPS[servlet_group]:
+                if not is_main_process and servletfunc in [
+                    pusher.register_servlets,
+                    logout.register_servlets,
+                    auth.register_servlets,
+                    tokenrefresh.register_servlets,
+                    reporting.register_servlets,
+                    openid.register_servlets,
+                    thirdparty.register_servlets,
+                    room_upgrade_rest_servlet.register_servlets,
+                    account_validity.register_servlets,
+                    admin.register_servlets_for_client_rest_resource,
+                    mutual_rooms.register_servlets,
+                    login_token_request.register_servlets,
+                    rendezvous.register_servlets,
+                    auth_issuer.register_servlets,
+                ]:
+                    continue

-        room.register_servlets(hs, client_resource)
-        login.register_servlets(hs, client_resource)
-        profile.register_servlets(hs, client_resource)
-        presence.register_servlets(hs, client_resource)
-        directory.register_servlets(hs, client_resource)
-        voip.register_servlets(hs, client_resource)
-        if is_main_process:
-            pusher.register_servlets(hs, client_resource)
-        push_rule.register_servlets(hs, client_resource)
-        if is_main_process:
-            logout.register_servlets(hs, client_resource)
-        sync.register_servlets(hs, client_resource)
-        filter.register_servlets(hs, client_resource)
-        account.register_servlets(hs, client_resource)
-        register.register_servlets(hs, client_resource)
-        if is_main_process:
-            auth.register_servlets(hs, client_resource)
-        receipts.register_servlets(hs, client_resource)
-        read_marker.register_servlets(hs, client_resource)
-        room_keys.register_servlets(hs, client_resource)
-        keys.register_servlets(hs, client_resource)
-        if is_main_process:
-            tokenrefresh.register_servlets(hs, client_resource)
-        tags.register_servlets(hs, client_resource)
-        account_data.register_servlets(hs, client_resource)
-        if is_main_process:
-            reporting.register_servlets(hs, client_resource)
-            openid.register_servlets(hs, client_resource)
-        notifications.register_servlets(hs, client_resource)
-        devices.register_servlets(hs, client_resource)
-        if is_main_process:
-            thirdparty.register_servlets(hs, client_resource)
-        sendtodevice.register_servlets(hs, client_resource)
-        user_directory.register_servlets(hs, client_resource)
-        if is_main_process:
-            room_upgrade_rest_servlet.register_servlets(hs, client_resource)
-        capabilities.register_servlets(hs, client_resource)
-        if is_main_process:
-            account_validity.register_servlets(hs, client_resource)
-        relations.register_servlets(hs, client_resource)
-        password_policy.register_servlets(hs, client_resource)
-        knock.register_servlets(hs, client_resource)
-        appservice_ping.register_servlets(hs, client_resource)
-        if hs.config.media.can_load_media_repo:
-            from synapse.rest.client import media
-
-            media.register_servlets(hs, client_resource)
-
-        # moving to /_synapse/admin
-        if is_main_process:
-            admin.register_servlets_for_client_rest_resource(hs, client_resource)
-
-        # unstable
-        if is_main_process:
-            mutual_rooms.register_servlets(hs, client_resource)
-            login_token_request.register_servlets(hs, client_resource)
-            rendezvous.register_servlets(hs, client_resource)
-            auth_issuer.register_servlets(hs, client_resource)
+                servletfunc(hs, client_resource)
--- a/synapse/rest/client/room.py
+++ b/synapse/rest/client/room.py
@ -67,7 +67,8 @@ from synapse.streams.config import PaginationConfig
 from synapse.types import JsonDict, Requester, StreamToken, ThirdPartyInstanceID, UserID
 from synapse.types.state import StateFilter
 from synapse.util.cancellation import cancellable
-from synapse.util.stringutils import parse_and_validate_server_name, random_string
+from synapse.util.events import generate_fake_event_id
+from synapse.util.stringutils import parse_and_validate_server_name

 if TYPE_CHECKING:
    from synapse.server import HomeServer
@ -325,7 +326,7 @@ class RoomStateEventRestServlet(RestServlet):
                )
                event_id = event.event_id
        except ShadowBanError:
-            event_id = "$" + random_string(43)
+            event_id = generate_fake_event_id()

        set_tag("event_id", event_id)
        ret = {"event_id": event_id}
@ -381,7 +382,7 @@ class RoomSendEventRestServlet(TransactionRestServlet):
            )
            event_id = event.event_id
        except ShadowBanError:
-            event_id = "$" + random_string(43)
+            event_id = generate_fake_event_id()

        set_tag("event_id", event_id)
        return 200, {"event_id": event_id}
@ -1197,7 +1198,7 @@ class RoomRedactEventRestServlet(TransactionRestServlet):

            event_id = event.event_id
        except ShadowBanError:
-            event_id = "$" + random_string(43)
+            event_id = generate_fake_event_id()

        set_tag("event_id", event_id)
        return 200, {"event_id": event_id}
--- a/synapse/rest/client/sync.py
+++ b/synapse/rest/client/sync.py
@ -899,6 +899,9 @@ class SlidingSyncRestServlet(RestServlet):
        body = parse_and_validate_json_object_from_request(request, SlidingSyncBody)

        # Tag and log useful data to differentiate requests.
+        set_tag(
+            "sliding_sync.sync_type", "initial" if from_token is None else "incremental"
+        )
        set_tag("sliding_sync.conn_id", body.conn_id or "")
        log_kv(
            {
@ -912,6 +915,12 @@ class SlidingSyncRestServlet(RestServlet):
                "sliding_sync.room_subscriptions": list(
                    (body.room_subscriptions or {}).keys()
                ),
+                # We also include the number of room subscriptions because logs are
+                # limited to 1024 characters and the large room ID list above can be cut
+                # off.
+                "sliding_sync.num_room_subscriptions": len(
+                    (body.room_subscriptions or {}).keys()
+                ),
            }
        )

@ -1035,6 +1044,11 @@ class SlidingSyncRestServlet(RestServlet):
            if room_result.initial:
                serialized_rooms[room_id]["initial"] = room_result.initial

+            if room_result.unstable_expanded_timeline:
+                serialized_rooms[room_id][
+                    "unstable_expanded_timeline"
+                ] = room_result.unstable_expanded_timeline
+
            # This will be omitted for invite/knock rooms with `stripped_state`
            if (
                room_result.required_state is not None
--- a/synapse/rest/client/versions.py
+++ b/synapse/rest/client/versions.py
@ -64,6 +64,7 @@ class VersionsRestServlet(RestServlet):

    async def on_GET(self, request: SynapseRequest) -> Tuple[int, JsonDict]:
        msc3881_enabled = self.config.experimental.msc3881_enabled
+        msc3575_enabled = self.config.experimental.msc3575_enabled

        if self.auth.has_access_token(request):
            requester = await self.auth.get_user_by_req(
@ -77,6 +78,9 @@ class VersionsRestServlet(RestServlet):
            msc3881_enabled = await self.store.is_feature_enabled(
                user_id, ExperimentalFeature.MSC3881
            )
+            msc3575_enabled = await self.store.is_feature_enabled(
+                user_id, ExperimentalFeature.MSC3575
+            )

        return (
            200,
@ -169,6 +173,8 @@ class VersionsRestServlet(RestServlet):
                    ),
                    # MSC4151: Report room API (Client-Server API)
                    "org.matrix.msc4151": self.config.experimental.msc4151_enabled,
+                    # Simplified sliding sync
+                    "org.matrix.simplified_msc3575": msc3575_enabled,
                },
            },
        )
--- a/synapse/server.py
+++ b/synapse/server.py
@ -34,6 +34,7 @@ from typing_extensions import TypeAlias

 from twisted.internet.interfaces import IOpenSSLContextFactory
 from twisted.internet.tcp import Port
+from twisted.python.threadpool import ThreadPool
 from twisted.web.iweb import IPolicyForHTTPS
 from twisted.web.resource import Resource

@ -123,6 +124,7 @@ from synapse.http.client import (
 )
 from synapse.http.matrixfederationclient import MatrixFederationHttpClient
 from synapse.media.media_repository import MediaRepository
+from synapse.metrics import register_threadpool
 from synapse.metrics.common_usage_metrics import CommonUsageMetricsManager
 from synapse.module_api import ModuleApi
 from synapse.module_api.callbacks import ModuleApiCallbacks
@ -941,3 +943,24 @@ class HomeServer(metaclass=abc.ABCMeta):
    @cache_in_self
    def get_task_scheduler(self) -> TaskScheduler:
        return TaskScheduler(self)
+
+    @cache_in_self
+    def get_media_sender_thread_pool(self) -> ThreadPool:
+        """Fetch the threadpool used to read files when responding to media
+        download requests."""
+
+        # We can choose a large threadpool size as these threads predominately
+        # do IO rather than CPU work.
+        media_threadpool = ThreadPool(
+            name="media_threadpool", minthreads=1, maxthreads=50
+        )
+
+        media_threadpool.start()
+        self.get_reactor().addSystemEventTrigger(
+            "during", "shutdown", media_threadpool.stop
+        )
+
+        # Register the threadpool with our metrics.
+        register_threadpool("media", media_threadpool)
+
+        return media_threadpool
--- a/synapse/storage/databases/main/profile.py
+++ b/synapse/storage/databases/main/profile.py
@ -144,6 +144,16 @@ class ProfileWorkerStore(SQLBaseStore):
        return 50

    async def get_profileinfo(self, user_id: UserID) -> ProfileInfo:
+        """
+        Fetch the display name and avatar URL of a user.
+
+        Args:
+            user_id: The user ID to fetch the profile for.
+
+        Returns:
+            The user's display name and avatar URL. Values may be null if unset
+             or if the user doesn't exist.
+        """
        profile = await self.db_pool.simple_select_one(
            table="profiles",
            keyvalues={"full_user_id": user_id.to_string()},
@ -158,6 +168,15 @@ class ProfileWorkerStore(SQLBaseStore):
        return ProfileInfo(avatar_url=profile[1], display_name=profile[0])

    async def get_profile_displayname(self, user_id: UserID) -> Optional[str]:
+        """
+        Fetch the display name of a user.
+
+        Args:
+            user_id: The user to get the display name for.
+
+        Raises:
+            404 if the user does not exist.
+        """
        return await self.db_pool.simple_select_one_onecol(
            table="profiles",
            keyvalues={"full_user_id": user_id.to_string()},
@ -166,6 +185,15 @@ class ProfileWorkerStore(SQLBaseStore):
        )

    async def get_profile_avatar_url(self, user_id: UserID) -> Optional[str]:
+        """
+        Fetch the avatar URL of a user.
+
+        Args:
+            user_id: The user to get the avatar URL for.
+
+        Raises:
+            404 if the user does not exist.
+        """
        return await self.db_pool.simple_select_one_onecol(
            table="profiles",
            keyvalues={"full_user_id": user_id.to_string()},
@ -174,6 +202,12 @@ class ProfileWorkerStore(SQLBaseStore):
        )

    async def create_profile(self, user_id: UserID) -> None:
+        """
+        Create a blank profile for a user.
+
+        Args:
+            user_id: The user to create the profile for.
+        """
        user_localpart = user_id.localpart
        await self.db_pool.simple_insert(
            table="profiles",
--- a/synapse/storage/databases/main/receipts.py
+++ b/synapse/storage/databases/main/receipts.py
@ -43,6 +43,7 @@ from synapse.storage.database import (
    DatabasePool,
    LoggingDatabaseConnection,
    LoggingTransaction,
+    make_tuple_in_list_sql_clause,
 )
 from synapse.storage.engines._base import IsolationLevel
 from synapse.storage.util.id_generators import MultiWriterIdGenerator
@ -51,10 +52,12 @@ from synapse.types import (
    JsonMapping,
    MultiWriterStreamToken,
    PersistedPosition,
+    StrCollection,
 )
 from synapse.util import json_encoder
 from synapse.util.caches.descriptors import cached, cachedList
 from synapse.util.caches.stream_change_cache import StreamChangeCache
+from synapse.util.iterutils import batch_iter

 if TYPE_CHECKING:
    from synapse.server import HomeServer
@ -479,6 +482,83 @@ class ReceiptsWorkerStore(SQLBaseStore):
        }
        return results

+    async def get_linearized_receipts_for_events(
+        self,
+        room_and_event_ids: Collection[Tuple[str, str]],
+    ) -> Sequence[JsonMapping]:
+        """Get all receipts for the given set of events.
+
+        Arguments:
+            room_and_event_ids: A collection of 2-tuples of room ID and
+                event IDs to fetch receipts for
+
+        Returns:
+            A list of receipts, one per room.
+        """
+
+        def get_linearized_receipts_for_events_txn(
+            txn: LoggingTransaction,
+            room_id_event_id_tuples: Collection[Tuple[str, str]],
+        ) -> List[Tuple[str, str, str, str, Optional[str], str]]:
+            clause, args = make_tuple_in_list_sql_clause(
+                self.database_engine, ("room_id", "event_id"), room_id_event_id_tuples
+            )
+
+            sql = f"""
+                SELECT room_id, receipt_type, user_id, event_id, thread_id, data
+                FROM receipts_linearized
+                WHERE {clause}
+            """
+
+            txn.execute(sql, args)
+
+            return txn.fetchall()
+
+        # room_id -> event_id -> receipt_type -> user_id -> receipt data
+        room_to_content: Dict[str, Dict[str, Dict[str, Dict[str, JsonMapping]]]] = {}
+        for batch in batch_iter(room_and_event_ids, 1000):
+            batch_results = await self.db_pool.runInteraction(
+                "get_linearized_receipts_for_events",
+                get_linearized_receipts_for_events_txn,
+                batch,
+            )
+
+            for (
+                room_id,
+                receipt_type,
+                user_id,
+                event_id,
+                thread_id,
+                data,
+            ) in batch_results:
+                content = room_to_content.setdefault(room_id, {})
+                user_receipts = content.setdefault(event_id, {}).setdefault(
+                    receipt_type, {}
+                )
+
+                receipt_data = db_to_json(data)
+                if thread_id is not None:
+                    receipt_data["thread_id"] = thread_id
+
+                # MSC4102: always replace threaded receipts with unthreaded ones
+                # if there is a clash. Specifically:
+                # - if there is no existing receipt, great, set the data.
+                # - if there is an existing receipt, is it threaded (thread_id
+                #    present)? YES: replace if this receipt has no thread id.
+                # NO: do not replace. This means we will drop some receipts, but
+                # MSC4102 is designed to drop semantically meaningless receipts,
+                # so this is okay. Previously, we would drop meaningful data!
+                if user_id in user_receipts:
+                    if "thread_id" in user_receipts[user_id] and not thread_id:
+                        user_receipts[user_id] = receipt_data
+                else:
+                    user_receipts[user_id] = receipt_data
+
+        return [
+            {"type": EduTypes.RECEIPT, "room_id": room_id, "content": content}
+            for room_id, content in room_to_content.items()
+        ]
+
    @cached(
        num_args=2,
    )
@ -550,6 +630,46 @@ class ReceiptsWorkerStore(SQLBaseStore):

        return results

+    async def get_rooms_with_receipts_between(
+        self,
+        room_ids: StrCollection,
+        from_key: MultiWriterStreamToken,
+        to_key: MultiWriterStreamToken,
+    ) -> StrCollection:
+        """Given a set of room_ids, find out which ones (may) have receipts
+        between the two tokens (> `from_token` and <= `to_token`)."""
+
+        room_ids = self._receipts_stream_cache.get_entities_changed(
+            room_ids, from_key.stream
+        )
+        if not room_ids:
+            return []
+
+        def f(txn: LoggingTransaction, room_ids: StrCollection) -> StrCollection:
+            clause, args = make_in_list_sql_clause(
+                self.database_engine, "room_id", room_ids
+            )
+
+            sql = f"""
+                SELECT DISTINCT room_id FROM receipts_linearized
+                WHERE {clause} AND ? < stream_id AND stream_id <= ?
+            """
+            args.append(from_key.stream)
+            args.append(to_key.get_max_stream_pos())
+
+            txn.execute(sql, args)
+
+            return [room_id for room_id, in txn]
+
+        results: List[str] = []
+        for batch in batch_iter(room_ids, 1000):
+            batch_result = await self.db_pool.runInteraction(
+                "get_rooms_with_receipts_between", f, batch
+            )
+            results.extend(batch_result)
+
+        return results
+
    async def get_users_sent_receipts_between(
        self, last_id: int, current_id: int
    ) -> List[str]:
@ -954,6 +1074,12 @@ class ReceiptsBackgroundUpdateStore(SQLBaseStore):
            self.RECEIPTS_GRAPH_UNIQUE_INDEX_UPDATE_NAME,
            self._background_receipts_graph_unique_index,
        )
+        self.db_pool.updates.register_background_index_update(
+            update_name="receipts_room_id_event_id_index",
+            index_name="receipts_linearized_event_id",
+            table="receipts_linearized",
+            columns=("room_id", "event_id"),
+        )

    async def _populate_receipt_event_stream_ordering(
        self, progress: JsonDict, batch_size: int
--- a/synapse/storage/databases/main/roommember.py
+++ b/synapse/storage/databases/main/roommember.py
@ -39,6 +39,7 @@ from typing import (
 import attr

 from synapse.api.constants import EventTypes, Membership
+from synapse.logging.opentracing import trace
 from synapse.metrics import LaterGauge
 from synapse.metrics.background_process_metrics import wrap_as_background_process
 from synapse.storage._base import SQLBaseStore, db_to_json, make_in_list_sql_clause
@ -422,6 +423,7 @@ class RoomMemberWorkerStore(EventsWorkerStore, CacheInvalidationWorkerStore):
                return invite
        return None

+    @trace
    async def get_rooms_for_local_user_where_membership_is(
        self,
        user_id: str,
--- a/synapse/storage/databases/main/state_deltas.py
+++ b/synapse/storage/databases/main/state_deltas.py
@ -24,11 +24,13 @@ from typing import List, Optional, Tuple

 import attr

+from synapse.logging.opentracing import trace
 from synapse.storage._base import SQLBaseStore
-from synapse.storage.database import LoggingTransaction
+from synapse.storage.database import LoggingTransaction, make_in_list_sql_clause
 from synapse.storage.databases.main.stream import _filter_results_by_stream
-from synapse.types import RoomStreamToken
+from synapse.types import RoomStreamToken, StrCollection
 from synapse.util.caches.stream_change_cache import StreamChangeCache
+from synapse.util.iterutils import batch_iter

 logger = logging.getLogger(__name__)

@ -159,11 +161,17 @@ class StateDeltasStore(SQLBaseStore):
            self._get_max_stream_id_in_current_state_deltas_txn,
        )

+    @trace
    async def get_current_state_deltas_for_room(
        self, room_id: str, from_token: RoomStreamToken, to_token: RoomStreamToken
    ) -> List[StateDelta]:
        """Get the state deltas between two tokens."""

+        if not self._curr_state_delta_stream_cache.has_entity_changed(
+            room_id, from_token.stream
+        ):
+            return []
+
        def get_current_state_deltas_for_room_txn(
            txn: LoggingTransaction,
        ) -> List[StateDelta]:
@ -193,3 +201,62 @@ class StateDeltasStore(SQLBaseStore):
        return await self.db_pool.runInteraction(
            "get_current_state_deltas_for_room", get_current_state_deltas_for_room_txn
        )
+
+    @trace
+    async def get_current_state_deltas_for_rooms(
+        self,
+        room_ids: StrCollection,
+        from_token: RoomStreamToken,
+        to_token: RoomStreamToken,
+    ) -> List[StateDelta]:
+        """Get the state deltas between two tokens for the set of rooms."""
+
+        room_ids = self._curr_state_delta_stream_cache.get_entities_changed(
+            room_ids, from_token.stream
+        )
+        if not room_ids:
+            return []
+
+        def get_current_state_deltas_for_rooms_txn(
+            txn: LoggingTransaction,
+            room_ids: StrCollection,
+        ) -> List[StateDelta]:
+            clause, args = make_in_list_sql_clause(
+                self.database_engine, "room_id", room_ids
+            )
+
+            sql = f"""
+                SELECT instance_name, stream_id, room_id, type, state_key, event_id, prev_event_id
+                FROM current_state_delta_stream
+                WHERE {clause} AND ? < stream_id AND stream_id <= ?
+                ORDER BY stream_id ASC
+            """
+            args.append(from_token.stream)
+            args.append(to_token.get_max_stream_pos())
+
+            txn.execute(sql, args)
+
+            return [
+                StateDelta(
+                    stream_id=row[1],
+                    room_id=row[2],
+                    event_type=row[3],
+                    state_key=row[4],
+                    event_id=row[5],
+                    prev_event_id=row[6],
+                )
+                for row in txn
+                if _filter_results_by_stream(from_token, to_token, row[0], row[1])
+            ]
+
+        results = []
+        for batch in batch_iter(room_ids, 1000):
+            deltas = await self.db_pool.runInteraction(
+                "get_current_state_deltas_for_rooms",
+                get_current_state_deltas_for_rooms_txn,
+                batch,
+            )
+
+            results.extend(deltas)
+
+        return results
--- a/synapse/storage/databases/main/stream.py
+++ b/synapse/storage/databases/main/stream.py
@ -51,6 +51,7 @@ from typing import (
    Iterable,
    List,
    Optional,
+    Protocol,
    Set,
    Tuple,
    cast,
@ -59,7 +60,7 @@ from typing import (

 import attr
 from immutabledict import immutabledict
-from typing_extensions import Literal
+from typing_extensions import Literal, assert_never

 from twisted.internet import defer

@ -67,7 +68,7 @@ from synapse.api.constants import Direction, EventTypes, Membership
 from synapse.api.filtering import Filter
 from synapse.events import EventBase
 from synapse.logging.context import make_deferred_yieldable, run_in_background
-from synapse.logging.opentracing import trace
+from synapse.logging.opentracing import tag_args, trace
 from synapse.storage._base import SQLBaseStore
 from synapse.storage.database import (
    DatabasePool,
@ -97,6 +98,18 @@ _STREAM_TOKEN = "stream"
 _TOPOLOGICAL_TOKEN = "topological"


+class PaginateFunction(Protocol):
+    async def __call__(
+        self,
+        *,
+        room_id: str,
+        from_key: RoomStreamToken,
+        to_key: Optional[RoomStreamToken] = None,
+        direction: Direction = Direction.BACKWARDS,
+        limit: int = 0,
+    ) -> Tuple[List[EventBase], RoomStreamToken]: ...
+
+
 # Used as return values for pagination APIs
@attr.s(slots=True, frozen=True, auto_attribs=True)
 class _EventDictReturn:
@ -280,7 +293,7 @@ def generate_pagination_bounds(


 def generate_next_token(
-    direction: Direction, last_topo_ordering: int, last_stream_ordering: int
+    direction: Direction, last_topo_ordering: Optional[int], last_stream_ordering: int
 ) -> RoomStreamToken:
    """
    Generate the next room stream token based on the currently returned data.
@ -447,7 +460,6 @@ def _filter_results_by_stream(
    The `instance_name` arg is optional to handle historic rows, and is
    interpreted as if it was "master".
    """
-
    if instance_name is None:
        instance_name = "master"

@ -660,33 +672,43 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):

    async def get_room_events_stream_for_rooms(
        self,
+        *,
        room_ids: Collection[str],
        from_key: RoomStreamToken,
-        to_key: RoomStreamToken,
+        to_key: Optional[RoomStreamToken] = None,
+        direction: Direction = Direction.BACKWARDS,
        limit: int = 0,
-        order: str = "DESC",
    ) -> Dict[str, Tuple[List[EventBase], RoomStreamToken]]:
        """Get new room events in stream ordering since `from_key`.

        Args:
            room_ids
-            from_key: Token from which no events are returned before
-            to_key: Token from which no events are returned after. (This
-                is typically the current stream token)
+            from_key: The token to stream from (starting point and heading in the given
+                direction)
+            to_key: The token representing the end stream position (end point)
            limit: Maximum number of events to return
-            order: Either "DESC" or "ASC". Determines which events are
-                returned when the result is limited. If "DESC" then the most
-                recent `limit` events are returned, otherwise returns the
-                oldest `limit` events.
+            direction: Indicates whether we are paginating forwards or backwards
+                from `from_key`.

        Returns:
            A map from room id to a tuple containing:
                - list of recent events in the room
                - stream ordering key for the start of the chunk of events returned.
+
+            When Direction.FORWARDS: from_key < x <= to_key, (ascending order)
+            When Direction.BACKWARDS: from_key >= x > to_key, (descending order)
        """
+        if direction == Direction.FORWARDS:
            room_ids = self._events_stream_cache.get_entities_changed(
                room_ids, from_key.stream
            )
+        elif direction == Direction.BACKWARDS:
+            if to_key is not None:
+                room_ids = self._events_stream_cache.get_entities_changed(
+                    room_ids, to_key.stream
+                )
+        else:
+            assert_never(direction)

        if not room_ids:
            return {}
@ -698,12 +720,12 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
                defer.gatherResults(
                    [
                        run_in_background(
-                            self.get_room_events_stream_for_room,
-                            room_id,
-                            from_key,
-                            to_key,
-                            limit,
-                            order=order,
+                            self.paginate_room_events_by_stream_ordering,
+                            room_id=room_id,
+                            from_key=from_key,
+                            to_key=to_key,
+                            direction=direction,
+                            limit=limit,
                        )
                        for room_id in rm_ids
                    ],
@ -727,69 +749,122 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
            if self._events_stream_cache.has_entity_changed(room_id, from_id)
        }

-    async def get_room_events_stream_for_room(
+    async def paginate_room_events_by_stream_ordering(
        self,
+        *,
        room_id: str,
        from_key: RoomStreamToken,
-        to_key: RoomStreamToken,
+        to_key: Optional[RoomStreamToken] = None,
+        direction: Direction = Direction.BACKWARDS,
        limit: int = 0,
-        order: str = "DESC",
    ) -> Tuple[List[EventBase], RoomStreamToken]:
-        """Get new room events in stream ordering since `from_key`.
+        """
+        Paginate events by `stream_ordering` in the room from the `from_key` in the
+        given `direction` to the `to_key` or `limit`.

        Args:
            room_id
-            from_key: Token from which no events are returned before
-            to_key: Token from which no events are returned after. (This
-                is typically the current stream token)
+            from_key: The token to stream from (starting point and heading in the given
+                direction)
+            to_key: The token representing the end stream position (end point)
+            direction: Indicates whether we are paginating forwards or backwards
+                from `from_key`.
            limit: Maximum number of events to return
-            order: Either "DESC" or "ASC". Determines which events are
-                returned when the result is limited. If "DESC" then the most
-                recent `limit` events are returned, otherwise returns the
-                oldest `limit` events.

        Returns:
-            The list of events (in ascending stream order) and the token from the start
-            of the chunk of events returned.
-        """
-        if from_key == to_key:
-            return [], from_key
+            The results as a list of events and a token that points to the end
+            of the result set. If no events are returned then the end of the
+            stream has been reached (i.e. there are no events between `from_key`
+            and `to_key`).

+            When Direction.FORWARDS: from_key < x <= to_key, (ascending order)
+            When Direction.BACKWARDS: from_key >= x > to_key, (descending order)
+        """
+
+        # FIXME: When going forwards, we should enforce that the `to_key` is not `None`
+        # because we always need an upper bound when querying the events stream (as
+        # otherwise we'll potentially pick up events that are not fully persisted).
+
+        # We should only be working with `stream_ordering` tokens here
+        assert from_key is None or from_key.topological is None
+        assert to_key is None or to_key.topological is None
+
+        # We can bail early if we're looking forwards, and our `to_key` is already
+        # before our `from_key`.
+        if (
+            direction == Direction.FORWARDS
+            and to_key is not None
+            and to_key.is_before_or_eq(from_key)
+        ):
+            # Token selection matches what we do below if there are no rows
+            return [], to_key if to_key else from_key
+        # Or vice-versa, if we're looking backwards and our `from_key` is already before
+        # our `to_key`.
+        elif (
+            direction == Direction.BACKWARDS
+            and to_key is not None
+            and from_key.is_before_or_eq(to_key)
+        ):
+            # Token selection matches what we do below if there are no rows
+            return [], to_key if to_key else from_key
+
+        # We can do a quick sanity check to see if any events have been sent in the room
+        # since the earlier token.
+        has_changed = True
+        if direction == Direction.FORWARDS:
            has_changed = self._events_stream_cache.has_entity_changed(
                room_id, from_key.stream
            )
+        elif direction == Direction.BACKWARDS:
+            if to_key is not None:
+                has_changed = self._events_stream_cache.has_entity_changed(
+                    room_id, to_key.stream
+                )
+        else:
+            assert_never(direction)

        if not has_changed:
-            return [], from_key
+            # Token selection matches what we do below if there are no rows
+            return [], to_key if to_key else from_key
+
+        order, from_bound, to_bound = generate_pagination_bounds(
+            direction, from_key, to_key
+        )
+
+        bounds = generate_pagination_where_clause(
+            direction=direction,
+            # The empty string will shortcut downstream code to only use the
+            # `stream_ordering` column
+            column_names=("", "stream_ordering"),
+            from_token=from_bound,
+            to_token=to_bound,
+            engine=self.database_engine,
+        )

        def f(txn: LoggingTransaction) -> List[_EventDictReturn]:
-            # To handle tokens with a non-empty instance_map we fetch more
-            # results than necessary and then filter down
-            min_from_id = from_key.stream
-            max_to_id = to_key.get_max_stream_pos()
-
-            sql = """
-                SELECT event_id, instance_name, topological_ordering, stream_ordering
+            sql = f"""
+                SELECT event_id, instance_name, stream_ordering
                FROM events
                WHERE
                    room_id = ?
                    AND not outlier
-                    AND stream_ordering > ? AND stream_ordering <= ?
-                ORDER BY stream_ordering %s LIMIT ?
-            """ % (
-                order,
-            )
-            txn.execute(sql, (room_id, min_from_id, max_to_id, 2 * limit))
+                    AND {bounds}
+                ORDER BY stream_ordering {order} LIMIT ?
+            """
+            txn.execute(sql, (room_id, 2 * limit))

            rows = [
                _EventDictReturn(event_id, None, stream_ordering)
-                for event_id, instance_name, topological_ordering, stream_ordering in txn
-                if _filter_results(
-                    from_key,
-                    to_key,
-                    instance_name,
-                    topological_ordering,
-                    stream_ordering,
+                for event_id, instance_name, stream_ordering in txn
+                if _filter_results_by_stream(
+                    lower_token=(
+                        to_key if direction == Direction.BACKWARDS else from_key
+                    ),
+                    upper_token=(
+                        from_key if direction == Direction.BACKWARDS else to_key
+                    ),
+                    instance_name=instance_name,
+                    stream_ordering=stream_ordering,
                )
            ][:limit]
            return rows
@ -800,18 +875,20 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
            [r.event_id for r in rows], get_prev_content=True
        )

-        if order.lower() == "desc":
-            ret.reverse()
-
        if rows:
-            key = RoomStreamToken(stream=min(r.stream_ordering for r in rows))
+            next_key = generate_next_token(
+                direction=direction,
+                last_topo_ordering=None,
+                last_stream_ordering=rows[-1].stream_ordering,
+            )
        else:
-            # Assume we didn't get anything because there was nothing to
-            # get.
-            key = from_key
+            # TODO (erikj): We should work out what to do here instead. (same as
+            # `_paginate_room_events_by_topological_ordering_txn(...)`)
+            next_key = to_key if to_key else from_key

-        return ret, key
+        return ret, next_key

+    @trace
    async def get_current_state_delta_membership_changes_for_user(
        self,
        user_id: str,
@ -1117,7 +1194,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):

        rows, token = await self.db_pool.runInteraction(
            "get_recent_event_ids_for_room",
-            self._paginate_room_events_txn,
+            self._paginate_room_events_by_topological_ordering_txn,
            room_id,
            from_token=end_token,
            limit=limit,
@ -1186,6 +1263,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):

        return None

+    @trace
    async def get_last_event_pos_in_room_before_stream_ordering(
        self,
        room_id: str,
@ -1622,7 +1700,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
            topological=topological_ordering, stream=stream_ordering
        )

-        rows, start_token = self._paginate_room_events_txn(
+        rows, start_token = self._paginate_room_events_by_topological_ordering_txn(
            txn,
            room_id,
            before_token,
@ -1632,7 +1710,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
        )
        events_before = [r.event_id for r in rows]

-        rows, end_token = self._paginate_room_events_txn(
+        rows, end_token = self._paginate_room_events_by_topological_ordering_txn(
            txn,
            room_id,
            after_token,
@ -1795,14 +1873,14 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
    def has_room_changed_since(self, room_id: str, stream_id: int) -> bool:
        return self._events_stream_cache.has_entity_changed(room_id, stream_id)

-    def _paginate_room_events_txn(
+    def _paginate_room_events_by_topological_ordering_txn(
        self,
        txn: LoggingTransaction,
        room_id: str,
        from_token: RoomStreamToken,
        to_token: Optional[RoomStreamToken] = None,
        direction: Direction = Direction.BACKWARDS,
-        limit: int = -1,
+        limit: int = 0,
        event_filter: Optional[Filter] = None,
    ) -> Tuple[List[_EventDictReturn], RoomStreamToken]:
        """Returns list of events before or after a given token.
@ -1824,6 +1902,24 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
            been reached (i.e. there are no events between `from_token` and
            `to_token`), or `limit` is zero.
        """
+        # We can bail early if we're looking forwards, and our `to_key` is already
+        # before our `from_token`.
+        if (
+            direction == Direction.FORWARDS
+            and to_token is not None
+            and to_token.is_before_or_eq(from_token)
+        ):
+            # Token selection matches what we do below if there are no rows
+            return [], to_token if to_token else from_token
+        # Or vice-versa, if we're looking backwards and our `from_token` is already before
+        # our `to_token`.
+        elif (
+            direction == Direction.BACKWARDS
+            and to_token is not None
+            and from_token.is_before_or_eq(to_token)
+        ):
+            # Token selection matches what we do below if there are no rows
+            return [], to_token if to_token else from_token

        args: List[Any] = [room_id]

@ -1908,7 +2004,6 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
            "bounds": bounds,
            "order": order,
        }
-
        txn.execute(sql, args)

        # Filter the result set.
@ -1940,27 +2035,30 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
        return rows, next_token

    @trace
-    async def paginate_room_events(
+    @tag_args
+    async def paginate_room_events_by_topological_ordering(
        self,
+        *,
        room_id: str,
        from_key: RoomStreamToken,
        to_key: Optional[RoomStreamToken] = None,
        direction: Direction = Direction.BACKWARDS,
-        limit: int = -1,
+        limit: int = 0,
        event_filter: Optional[Filter] = None,
    ) -> Tuple[List[EventBase], RoomStreamToken]:
-        """Returns list of events before or after a given token.
-
-        When Direction.FORWARDS: from_key < x <= to_key
-        When Direction.BACKWARDS: from_key >= x > to_key
+        """
+        Paginate events by `topological_ordering` (tie-break with `stream_ordering`) in
+        the room from the `from_key` in the given `direction` to the `to_key` or
+        `limit`.

        Args:
            room_id
-            from_key: The token used to stream from
-            to_key: A token which if given limits the results to only those before
+            from_key: The token to stream from (starting point and heading in the given
+                direction)
+            to_key: The token representing the end stream position (end point)
            direction: Indicates whether we are paginating forwards or backwards
                from `from_key`.
-            limit: The maximum number of events to return.
+            limit: Maximum number of events to return
            event_filter: If provided filters the events to those that match the filter.

        Returns:
@ -1968,8 +2066,18 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
            of the result set. If no events are returned then the end of the
            stream has been reached (i.e. there are no events between `from_key`
            and `to_key`).
+
+            When Direction.FORWARDS: from_key < x <= to_key, (ascending order)
+            When Direction.BACKWARDS: from_key >= x > to_key, (descending order)
        """

+        # FIXME: When going forwards, we should enforce that the `to_key` is not `None`
+        # because we always need an upper bound when querying the events stream (as
+        # otherwise we'll potentially pick up events that are not fully persisted).
+
+        # We have these checks outside of the transaction function (txn) to save getting
+        # a DB connection and switching threads if we don't need to.
+        #
        # We can bail early if we're looking forwards, and our `to_key` is already
        # before our `from_key`.
        if (
@ -1992,8 +2100,8 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):
            return [], to_key if to_key else from_key

        rows, token = await self.db_pool.runInteraction(
-            "paginate_room_events",
-            self._paginate_room_events_txn,
+            "paginate_room_events_by_topological_ordering",
+            self._paginate_room_events_by_topological_ordering_txn,
            room_id,
            from_key,
            to_key,
@ -2105,6 +2213,7 @@ class StreamWorkerStore(EventsWorkerStore, SQLBaseStore):

        return None

+    @trace
    def get_rooms_that_might_have_updates(
        self, room_ids: StrCollection, from_token: RoomStreamToken
    ) -> StrCollection:
--- a/synapse/storage/schema/main/delta/86/02_receipts_event_id_index.sql
+++ b/synapse/storage/schema/main/delta/86/02_receipts_event_id_index.sql
@ -0,0 +1,15 @@
+--
+-- This file is licensed under the Affero General Public License (AGPL) version 3.
+--
+-- Copyright (C) 2024 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>.
+
+INSERT INTO background_updates (ordering, update_name, progress_json) VALUES
+    (8602, 'receipts_room_id_event_id_index', '{}');
--- a/synapse/types/handlers/init.py
+++ b/synapse/types/handlers/init.py
@ -171,6 +171,9 @@ class SlidingSyncResult:
                their local state. When there is an update, servers MUST omit this flag
                entirely and NOT send "initial":false as this is wasteful on bandwidth. The
                absence of this flag means 'false'.
+            unstable_expanded_timeline: Flag which is set if we're returning more historic
+                events due to the timeline limit having increased. See "XXX: Odd behavior"
+                comment ing `synapse.handlers.sliding_sync`.
            required_state: The current state of the room
            timeline: Latest events in the room. The last event is the most recent.
            bundled_aggregations: A mapping of event ID to the bundled aggregations for
@ -219,6 +222,7 @@ class SlidingSyncResult:
        heroes: Optional[List[StrippedHero]]
        is_dm: bool
        initial: bool
+        unstable_expanded_timeline: bool
        # Should be empty for invite/knock rooms with `stripped_state`
        required_state: List[EventBase]
        # Should be empty for invite/knock rooms with `stripped_state`
--- a/synapse/util/async_helpers.py
+++ b/synapse/util/async_helpers.py
@ -885,3 +885,46 @@ class AwakenableSleeper:
            # Cancel the sleep if we were woken up
            if call.active():
                call.cancel()
+
+
+class DeferredEvent:
+    """Like threading.Event but for async code"""
+
+    def __init__(self, reactor: IReactorTime) -> None:
+        self._reactor = reactor
+        self._deferred: "defer.Deferred[None]" = defer.Deferred()
+
+    def set(self) -> None:
+        if not self._deferred.called:
+            self._deferred.callback(None)
+
+    def clear(self) -> None:
+        if self._deferred.called:
+            self._deferred = defer.Deferred()
+
+    def is_set(self) -> bool:
+        return self._deferred.called
+
+    async def wait(self, timeout_seconds: float) -> bool:
+        if self.is_set():
+            return True
+
+        # Create a deferred that gets called in N seconds
+        sleep_deferred: "defer.Deferred[None]" = defer.Deferred()
+        call = self._reactor.callLater(timeout_seconds, sleep_deferred.callback, None)
+
+        try:
+            await make_deferred_yieldable(
+                defer.DeferredList(
+                    [sleep_deferred, self._deferred],
+                    fireOnOneCallback=True,
+                    fireOnOneErrback=True,
+                    consumeErrors=True,
+                )
+            )
+        finally:
+            # Cancel the sleep if we were woken up
+            if call.active():
+                call.cancel()
+
+        return self.is_set()
--- a/synapse/util/events.py
+++ b/synapse/util/events.py
@ -0,0 +1,29 @@
+#
+# This file is licensed under the Affero General Public License (AGPL) version 3.
+#
+# Copyright (C) 2024 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>.
+#
+#
+
+from synapse.util.stringutils import random_string
+
+
+def generate_fake_event_id() -> str:
+    """
+    Generate an event ID from random ASCII characters.
+
+    This is primarily useful for generating fake event IDs in response to
+    requests from shadow-banned users.
+
+    Returns:
+        A string intended to look like an event ID, but with no actual meaning.
+    """
+    return "$" + random_string(43)
--- a/tests/handlers/test_federation.py
+++ b/tests/handlers/test_federation.py
@ -44,7 +44,7 @@ from synapse.rest.client import login, room
 from synapse.server import HomeServer
 from synapse.storage.databases.main.events_worker import EventCacheEntry
 from synapse.util import Clock
-from synapse.util.stringutils import random_string
+from synapse.util.events import generate_fake_event_id

 from tests import unittest
 from tests.test_utils import event_injection
@ -52,10 +52,6 @@ from tests.test_utils import event_injection
 logger = logging.getLogger(__name__)


-def generate_fake_event_id() -> str:
-    return "$fake_" + random_string(43)
-
-
 class FederationTestCase(unittest.FederatingHomeserverTestCase):
    servlets = [
        admin.register_servlets,
--- a/tests/http/test_client.py
+++ b/tests/http/test_client.py
@ -49,8 +49,11 @@ from tests.unittest import TestCase


 class ReadMultipartResponseTests(TestCase):
-    data1 = b"\r\n\r\n--6067d4698f8d40a0a794ea7d7379d53a\r\nContent-Type: application/json\r\n\r\n{}\r\n--6067d4698f8d40a0a794ea7d7379d53a\r\nContent-Type: text/plain\r\nContent-Disposition: inline; filename=test_upload\r\n\r\nfile_"
-    data2 = b"to_stream\r\n--6067d4698f8d40a0a794ea7d7379d53a--\r\n\r\n"
+    multipart_response_data1 = b"\r\n\r\n--6067d4698f8d40a0a794ea7d7379d53a\r\nContent-Type: application/json\r\n\r\n{}\r\n--6067d4698f8d40a0a794ea7d7379d53a\r\nContent-Type: text/plain\r\nContent-Disposition: inline; filename=test_upload\r\n\r\nfile_"
+    multipart_response_data2 = (
+        b"to_stream\r\n--6067d4698f8d40a0a794ea7d7379d53a--\r\n\r\n"
+    )
+    multipart_response_data_cased = b"\r\n\r\n--6067d4698f8d40a0a794ea7d7379d53a\r\ncOntEnt-type: application/json\r\n\r\n{}\r\n--6067d4698f8d40a0a794ea7d7379d53a\r\nContent-tyPe: text/plain\r\nconTent-dispOsition: inline; filename=test_upload\r\n\r\nfile_"

    redirect_data = b"\r\n\r\n--6067d4698f8d40a0a794ea7d7379d53a\r\nContent-Type: application/json\r\n\r\n{}\r\n--6067d4698f8d40a0a794ea7d7379d53a\r\nLocation: https://cdn.example.org/ab/c1/2345.txt\r\n\r\n--6067d4698f8d40a0a794ea7d7379d53a--\r\n\r\n"

@ -103,8 +106,31 @@ class ReadMultipartResponseTests(TestCase):
        result, deferred, protocol = self._build_multipart_response(249, 250)

        # Start sending data.
-        protocol.dataReceived(self.data1)
-        protocol.dataReceived(self.data2)
+        protocol.dataReceived(self.multipart_response_data1)
+        protocol.dataReceived(self.multipart_response_data2)
+        # Close the connection.
+        protocol.connectionLost(Failure(ResponseDone()))
+
+        multipart_response: MultipartResponse = deferred.result  # type: ignore[assignment]
+
+        self.assertEqual(multipart_response.json, b"{}")
+        self.assertEqual(result.getvalue(), b"file_to_stream")
+        self.assertEqual(multipart_response.length, len(b"file_to_stream"))
+        self.assertEqual(multipart_response.content_type, b"text/plain")
+        self.assertEqual(
+            multipart_response.disposition, b"inline; filename=test_upload"
+        )
+
+    def test_parse_file_lowercase_headers(self) -> None:
+        """
+        Check that a multipart response containing a file is properly parsed
+        into the json/file parts, and the json and file are properly captured if the http headers are lowercased
+        """
+        result, deferred, protocol = self._build_multipart_response(249, 250)
+
+        # Start sending data.
+        protocol.dataReceived(self.multipart_response_data_cased)
+        protocol.dataReceived(self.multipart_response_data2)
        # Close the connection.
        protocol.connectionLost(Failure(ResponseDone()))

@ -143,7 +169,7 @@ class ReadMultipartResponseTests(TestCase):
        result, deferred, protocol = self._build_multipart_response(UNKNOWN_LENGTH, 180)

        # Start sending data.
-        protocol.dataReceived(self.data1)
+        protocol.dataReceived(self.multipart_response_data1)

        self.assertEqual(result.getvalue(), b"file_")
        self._assert_error(deferred, protocol)
@ -154,11 +180,11 @@ class ReadMultipartResponseTests(TestCase):
        result, deferred, protocol = self._build_multipart_response(UNKNOWN_LENGTH, 180)

        # Start sending data.
-        protocol.dataReceived(self.data1)
+        protocol.dataReceived(self.multipart_response_data1)
        self._assert_error(deferred, protocol)

        # More data might have come in.
-        protocol.dataReceived(self.data2)
+        protocol.dataReceived(self.multipart_response_data2)

        self.assertEqual(result.getvalue(), b"file_")
        self._assert_error(deferred, protocol)
@ -172,7 +198,7 @@ class ReadMultipartResponseTests(TestCase):
        self.assertFalse(deferred.called)

        # Start sending data.
-        protocol.dataReceived(self.data1)
+        protocol.dataReceived(self.multipart_response_data1)
        self._assert_error(deferred, protocol)
        self._cleanup_error(deferred)

--- a/tests/rest/client/sliding_sync/test_connection_tracking.py
+++ b/tests/rest/client/sliding_sync/test_connection_tracking.py
@ -21,8 +21,6 @@ import synapse.rest.admin
 from synapse.api.constants import EventTypes
 from synapse.rest.client import login, room, sync
 from synapse.server import HomeServer
-from synapse.types import SlidingSyncStreamToken
-from synapse.types.handlers import SlidingSyncConfig
 from synapse.util import Clock

 from tests.rest.client.sliding_sync.test_sliding_sync import SlidingSyncBase
@ -130,7 +128,6 @@ class SlidingSyncConnectionTrackingTestCase(SlidingSyncBase):
        self.helper.send(room_id1, "msg", tok=user1_tok)

        timeline_limit = 5
-        conn_id = "conn_id"
        sync_body = {
            "lists": {
                "foo-list": {
@ -170,40 +167,6 @@ class SlidingSyncConnectionTrackingTestCase(SlidingSyncBase):
            response_body["rooms"].keys(), {room_id2}, response_body["rooms"]
        )

-        # FIXME: This is a hack to record that the first room wasn't sent down
-        # sync, as we don't implement that currently.
-        sliding_sync_handler = self.hs.get_sliding_sync_handler()
-        requester = self.get_success(
-            self.hs.get_auth().get_user_by_access_token(user1_tok)
-        )
-        sync_config = SlidingSyncConfig(
-            user=requester.user,
-            requester=requester,
-            conn_id=conn_id,
-        )
-
-        parsed_initial_from_token = self.get_success(
-            SlidingSyncStreamToken.from_string(self.store, initial_from_token)
-        )
-        connection_position = self.get_success(
-            sliding_sync_handler.connection_store.record_rooms(
-                sync_config,
-                parsed_initial_from_token,
-                sent_room_ids=[],
-                unsent_room_ids=[room_id1],
-            )
-        )
-
-        # FIXME: Now fix up `from_token` with new connect position above.
-        parsed_from_token = self.get_success(
-            SlidingSyncStreamToken.from_string(self.store, from_token)
-        )
-        parsed_from_token = SlidingSyncStreamToken(
-            stream_token=parsed_from_token.stream_token,
-            connection_position=connection_position,
-        )
-        from_token = self.get_success(parsed_from_token.to_string(self.store))
-
        # We now send another event to room1, so we should sync all the missing events.
        resp = self.helper.send(room_id1, "msg2", tok=user1_tok)
        expected_events.append(resp["event_id"])
@ -238,7 +201,6 @@ class SlidingSyncConnectionTrackingTestCase(SlidingSyncBase):

        self.helper.send(room_id1, "msg", tok=user1_tok)

-        conn_id = "conn_id"
        sync_body = {
            "lists": {
                "foo-list": {
@ -279,40 +241,6 @@ class SlidingSyncConnectionTrackingTestCase(SlidingSyncBase):
            response_body["rooms"].keys(), {room_id2}, response_body["rooms"]
        )

-        # FIXME: This is a hack to record that the first room wasn't sent down
-        # sync, as we don't implement that currently.
-        sliding_sync_handler = self.hs.get_sliding_sync_handler()
-        requester = self.get_success(
-            self.hs.get_auth().get_user_by_access_token(user1_tok)
-        )
-        sync_config = SlidingSyncConfig(
-            user=requester.user,
-            requester=requester,
-            conn_id=conn_id,
-        )
-
-        parsed_initial_from_token = self.get_success(
-            SlidingSyncStreamToken.from_string(self.store, initial_from_token)
-        )
-        connection_position = self.get_success(
-            sliding_sync_handler.connection_store.record_rooms(
-                sync_config,
-                parsed_initial_from_token,
-                sent_room_ids=[],
-                unsent_room_ids=[room_id1],
-            )
-        )
-
-        # FIXME: Now fix up `from_token` with new connect position above.
-        parsed_from_token = self.get_success(
-            SlidingSyncStreamToken.from_string(self.store, from_token)
-        )
-        parsed_from_token = SlidingSyncStreamToken(
-            stream_token=parsed_from_token.stream_token,
-            connection_position=connection_position,
-        )
-        from_token = self.get_success(parsed_from_token.to_string(self.store))
-
        # We now send another event to room1, so we should sync all the missing state.
        self.helper.send(room_id1, "msg", tok=user1_tok)

--- a/tests/rest/client/sliding_sync/test_extension_receipts.py
+++ b/tests/rest/client/sliding_sync/test_extension_receipts.py
@ -677,3 +677,108 @@ class SlidingSyncReceiptsExtensionTestCase(SlidingSyncBase):
            set(),
            exact=True,
        )
+
+    def test_receipts_incremental_sync_out_of_range(self) -> None:
+        """Tests that we don't return read receipts for rooms that fall out of
+        range, but then do send all read receipts once they're back in range.
+        """
+
+        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)
+        room_id2 = self.helper.create_room_as(user2_id, tok=user2_tok)
+        self.helper.join(room_id2, user1_id, tok=user1_tok)
+
+        # Send a message and read receipt into room2
+        event_response = self.helper.send(room_id2, body="new event", tok=user2_tok)
+        room2_event_id = event_response["event_id"]
+
+        self.helper.send_read_receipt(room_id2, room2_event_id, tok=user1_tok)
+
+        # Now send a message into room1 so that it is at the top of the list
+        self.helper.send(room_id1, body="new event", tok=user2_tok)
+
+        # Make a SS request for only the top room.
+        sync_body = {
+            "lists": {
+                "main": {
+                    "ranges": [[0, 0]],
+                    "required_state": [],
+                    "timeline_limit": 5,
+                }
+            },
+            "extensions": {
+                "receipts": {
+                    "enabled": True,
+                }
+            },
+        }
+        response_body, from_token = self.do_sync(sync_body, tok=user1_tok)
+
+        # The receipt is in room2, but only room1 is returned, so we don't
+        # expect to get the receipt.
+        self.assertIncludes(
+            response_body["extensions"]["receipts"].get("rooms").keys(),
+            set(),
+            exact=True,
+        )
+
+        # Move room2 into range.
+        self.helper.send(room_id2, body="new event", tok=user2_tok)
+
+        response_body, from_token = self.do_sync(
+            sync_body, since=from_token, tok=user1_tok
+        )
+
+        # We expect to see the read receipt of room2, as that has the most
+        # recent update.
+        self.assertIncludes(
+            response_body["extensions"]["receipts"].get("rooms").keys(),
+            {room_id2},
+            exact=True,
+        )
+        receipt = response_body["extensions"]["receipts"]["rooms"][room_id2]
+        self.assertIncludes(
+            receipt["content"][room2_event_id][ReceiptTypes.READ].keys(),
+            {user1_id},
+            exact=True,
+        )
+
+        # Send a message into room1 to bump it to the top, but also send a
+        # receipt in room2
+        self.helper.send(room_id1, body="new event", tok=user2_tok)
+        self.helper.send_read_receipt(room_id2, room2_event_id, tok=user2_tok)
+
+        # We don't expect to see the new read receipt.
+        response_body, from_token = self.do_sync(
+            sync_body, since=from_token, tok=user1_tok
+        )
+        self.assertIncludes(
+            response_body["extensions"]["receipts"].get("rooms").keys(),
+            set(),
+            exact=True,
+        )
+
+        # But if we send a new message into room2, we expect to get the missing receipts
+        self.helper.send(room_id2, body="new event", tok=user2_tok)
+
+        response_body, from_token = self.do_sync(
+            sync_body, since=from_token, tok=user1_tok
+        )
+        self.assertIncludes(
+            response_body["extensions"]["receipts"].get("rooms").keys(),
+            {room_id2},
+            exact=True,
+        )
+
+        # We should only see the new receipt
+        receipt = response_body["extensions"]["receipts"]["rooms"][room_id2]
+        self.assertIncludes(
+            receipt["content"][room2_event_id][ReceiptTypes.READ].keys(),
+            {user2_id},
+            exact=True,
+        )
--- a/tests/rest/client/sliding_sync/test_extensions.py
+++ b/tests/rest/client/sliding_sync/test_extensions.py
@ -120,19 +120,26 @@ class SlidingSyncExtensionsTestCase(SlidingSyncBase):
                "foo-list": {
                    "ranges": [[0, 1]],
                    "required_state": [],
-                    "timeline_limit": 0,
+                    # We set this to `1` because we're testing `receipts` which
+                    # interact with the `timeline`. With receipts, when a room
+                    # hasn't been sent down the connection before or it appears
+                    # as `initial: true`, we only include receipts for events in
+                    # the timeline to avoid bloating and blowing up the sync
+                    # response as the number of users in the room increases.
+                    # (this behavior is part of the spec)
+                    "timeline_limit": 1,
                },
                # We expect this list range to include room5, room4, room3
                "bar-list": {
                    "ranges": [[0, 2]],
                    "required_state": [],
-                    "timeline_limit": 0,
+                    "timeline_limit": 1,
                },
            },
            "room_subscriptions": {
                room_id1: {
                    "required_state": [],
-                    "timeline_limit": 0,
+                    "timeline_limit": 1,
                }
            },
        }
--- a/tests/rest/client/sliding_sync/test_rooms_required_state.py
+++ b/tests/rest/client/sliding_sync/test_rooms_required_state.py
@ -631,8 +631,7 @@ class SlidingSyncRoomsRequiredStateTestCase(SlidingSyncBase):

    def test_rooms_required_state_partial_state(self) -> None:
        """
-        Test partially-stated room are excluded unless `rooms.required_state` is
-        lazy-loading room members.
+        Test partially-stated room are excluded if they require full state.
        """
        user1_id = self.register_user("user1", "pass")
        user1_tok = self.login(user1_id, "pass")
@ -649,59 +648,195 @@ class SlidingSyncRoomsRequiredStateTestCase(SlidingSyncBase):
            mark_event_as_partial_state(self.hs, join_response2["event_id"], room_id2)
        )

-        # Make the Sliding Sync request (NOT lazy-loading room members)
+        # Make the Sliding Sync request with examples where `must_await_full_state()` is
+        # `False`
        sync_body = {
            "lists": {
-                "foo-list": {
+                "no-state-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [],
+                    "timeline_limit": 0,
+                },
+                "other-state-list": {
                    "ranges": [[0, 1]],
                    "required_state": [
                        [EventTypes.Create, ""],
                    ],
                    "timeline_limit": 0,
                },
+                "lazy-load-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [
+                        [EventTypes.Create, ""],
+                        # Lazy-load room members
+                        [EventTypes.Member, StateValues.LAZY],
+                        # Local member
+                        [EventTypes.Member, user2_id],
+                    ],
+                    "timeline_limit": 0,
+                },
+                "local-members-only-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [
+                        # Own user ID
+                        [EventTypes.Member, user1_id],
+                        # Local member
+                        [EventTypes.Member, user2_id],
+                    ],
+                    "timeline_limit": 0,
+                },
+                "me-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [
+                        # Own user ID
+                        [EventTypes.Member, StateValues.ME],
+                        # Local member
+                        [EventTypes.Member, user2_id],
+                    ],
+                    "timeline_limit": 0,
+                },
+                "wildcard-type-local-state-key-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [
+                        ["*", user1_id],
+                        # Not a user ID
+                        ["*", "foobarbaz"],
+                        # Not a user ID
+                        ["*", "foo.bar.baz"],
+                        # Not a user ID
+                        ["*", "@foo"],
+                    ],
+                    "timeline_limit": 0,
+                },
+            }
+        }
+        response_body, _ = self.do_sync(sync_body, tok=user1_tok)
+
+        # The list should include both rooms now because we don't need full state
+        for list_key in response_body["lists"].keys():
+            self.assertIncludes(
+                set(response_body["lists"][list_key]["ops"][0]["room_ids"]),
+                {room_id2, room_id1},
+                exact=True,
+                message=f"Expected all rooms to show up for list_key={list_key}. Response "
+                + str(response_body["lists"][list_key]),
+            )
+
+        # Take each of the list variants and apply them to room subscriptions to make
+        # sure the same rules apply
+        for list_key in sync_body["lists"].keys():
+            sync_body_for_subscriptions = {
+                "room_subscriptions": {
+                    room_id1: {
+                        "required_state": sync_body["lists"][list_key][
+                            "required_state"
+                        ],
+                        "timeline_limit": 0,
+                    },
+                    room_id2: {
+                        "required_state": sync_body["lists"][list_key][
+                            "required_state"
+                        ],
+                        "timeline_limit": 0,
+                    },
+                }
+            }
+            response_body, _ = self.do_sync(sync_body_for_subscriptions, tok=user1_tok)
+
+            self.assertIncludes(
+                set(response_body["rooms"].keys()),
+                {room_id2, room_id1},
+                exact=True,
+                message=f"Expected all rooms to show up for test_key={list_key}.",
+            )
+
+        # =====================================================================
+
+        # Make the Sliding Sync request with examples where `must_await_full_state()` is
+        # `True`
+        sync_body = {
+            "lists": {
+                "wildcard-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [
+                        ["*", "*"],
+                    ],
+                    "timeline_limit": 0,
+                },
+                "wildcard-type-remote-state-key-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [
+                        ["*", "@some:remote"],
+                        # Not a user ID
+                        ["*", "foobarbaz"],
+                        # Not a user ID
+                        ["*", "foo.bar.baz"],
+                        # Not a user ID
+                        ["*", "@foo"],
+                    ],
+                    "timeline_limit": 0,
+                },
+                "remote-member-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [
+                        # Own user ID
+                        [EventTypes.Member, user1_id],
+                        # Remote member
+                        [EventTypes.Member, "@some:remote"],
+                        # Local member
+                        [EventTypes.Member, user2_id],
+                    ],
+                    "timeline_limit": 0,
+                },
+                "lazy-but-remote-member-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [
+                        # Lazy-load room members
+                        [EventTypes.Member, StateValues.LAZY],
+                        # Remote member
+                        [EventTypes.Member, "@some:remote"],
+                    ],
+                    "timeline_limit": 0,
+                },
            }
        }
        response_body, _ = self.do_sync(sync_body, tok=user1_tok)

        # Make sure the list includes room1 but room2 is excluded because it's still
        # partially-stated
-        self.assertListEqual(
-            list(response_body["lists"]["foo-list"]["ops"]),
-            [
-                {
-                    "op": "SYNC",
-                    "range": [0, 1],
-                    "room_ids": [room_id1],
-                }
-            ],
-            response_body["lists"]["foo-list"],
+        for list_key in response_body["lists"].keys():
+            self.assertIncludes(
+                set(response_body["lists"][list_key]["ops"][0]["room_ids"]),
+                {room_id1},
+                exact=True,
+                message=f"Expected only fully-stated rooms to show up for list_key={list_key}. Response "
+                + str(response_body["lists"][list_key]),
            )

-        # Make the Sliding Sync request (with lazy-loading room members)
-        sync_body = {
-            "lists": {
-                "foo-list": {
-                    "ranges": [[0, 1]],
-                    "required_state": [
-                        [EventTypes.Create, ""],
-                        # Lazy-load room members
-                        [EventTypes.Member, StateValues.LAZY],
+        # Take each of the list variants and apply them to room subscriptions to make
+        # sure the same rules apply
+        for list_key in sync_body["lists"].keys():
+            sync_body_for_subscriptions = {
+                "room_subscriptions": {
+                    room_id1: {
+                        "required_state": sync_body["lists"][list_key][
+                            "required_state"
+                        ],
+                        "timeline_limit": 0,
+                    },
+                    room_id2: {
+                        "required_state": sync_body["lists"][list_key][
+                            "required_state"
                        ],
                        "timeline_limit": 0,
                    },
                }
            }
-        response_body, _ = self.do_sync(sync_body, tok=user1_tok)
+            response_body, _ = self.do_sync(sync_body_for_subscriptions, tok=user1_tok)

-        # The list should include both rooms now because we're lazy-loading room members
-        self.assertListEqual(
-            list(response_body["lists"]["foo-list"]["ops"]),
-            [
-                {
-                    "op": "SYNC",
-                    "range": [0, 1],
-                    "room_ids": [room_id2, room_id1],
-                }
-            ],
-            response_body["lists"]["foo-list"],
+            self.assertIncludes(
+                set(response_body["rooms"].keys()),
+                {room_id1},
+                exact=True,
+                message=f"Expected only fully-stated rooms to show up for test_key={list_key}.",
            )
--- a/tests/rest/client/sliding_sync/test_rooms_timeline.py
+++ b/tests/rest/client/sliding_sync/test_rooms_timeline.py
@ -17,6 +17,7 @@ from typing import List, Optional
 from twisted.test.proto_helpers import MemoryReactor

 import synapse.rest.admin
+from synapse.api.constants import EventTypes
 from synapse.rest.client import login, room, sync
 from synapse.server import HomeServer
 from synapse.types import StreamToken, StrSequence
@ -573,3 +574,138 @@ class SlidingSyncRoomsTimelineTestCase(SlidingSyncBase):

        # Nothing to see for this banned user in the room in the token range
        self.assertIsNone(response_body["rooms"].get(room_id1))
+
+    def test_increasing_timeline_range_sends_more_messages(self) -> None:
+        """
+        Test that increasing the timeline limit via room subscriptions sends the
+        room down with more messages in a limited sync.
+        """
+
+        user1_id = self.register_user("user1", "pass")
+        user1_tok = self.login(user1_id, "pass")
+
+        room_id1 = self.helper.create_room_as(user1_id, tok=user1_tok)
+
+        sync_body = {
+            "lists": {
+                "foo-list": {
+                    "ranges": [[0, 1]],
+                    "required_state": [[EventTypes.Create, ""]],
+                    "timeline_limit": 1,
+                }
+            }
+        }
+
+        message_events = []
+        for _ in range(10):
+            resp = self.helper.send(room_id1, "msg", tok=user1_tok)
+            message_events.append(resp["event_id"])
+
+        # Make the first Sliding Sync request
+        response_body, from_token = self.do_sync(sync_body, tok=user1_tok)
+        room_response = response_body["rooms"][room_id1]
+
+        self.assertEqual(room_response["initial"], True)
+        self.assertNotIn("unstable_expanded_timeline", room_response)
+        self.assertEqual(room_response["limited"], True)
+
+        # We only expect the last message at first
+        self._assertTimelineEqual(
+            room_id=room_id1,
+            actual_event_ids=[event["event_id"] for event in room_response["timeline"]],
+            expected_event_ids=message_events[-1:],
+            message=str(room_response["timeline"]),
+        )
+
+        # We also expect to get the create event state.
+        state_map = self.get_success(
+            self.storage_controllers.state.get_current_state(room_id1)
+        )
+        self._assertRequiredStateIncludes(
+            room_response["required_state"],
+            {state_map[(EventTypes.Create, "")]},
+            exact=True,
+        )
+
+        # Now do another request with a room subscription with an increased timeline limit
+        sync_body["room_subscriptions"] = {
+            room_id1: {
+                "required_state": [],
+                "timeline_limit": 10,
+            }
+        }
+
+        response_body, from_token = self.do_sync(
+            sync_body, since=from_token, tok=user1_tok
+        )
+        room_response = response_body["rooms"][room_id1]
+
+        self.assertNotIn("initial", room_response)
+        self.assertEqual(room_response["unstable_expanded_timeline"], True)
+        self.assertEqual(room_response["limited"], True)
+
+        # Now we expect all the messages
+        self._assertTimelineEqual(
+            room_id=room_id1,
+            actual_event_ids=[event["event_id"] for event in room_response["timeline"]],
+            expected_event_ids=message_events,
+            message=str(room_response["timeline"]),
+        )
+
+        # We don't expect to get the room create down, as nothing has changed.
+        self.assertNotIn("required_state", room_response)
+
+        # Decreasing the timeline limit shouldn't resend any events
+        sync_body["room_subscriptions"] = {
+            room_id1: {
+                "required_state": [],
+                "timeline_limit": 5,
+            }
+        }
+
+        event_response = self.helper.send(room_id1, "msg", tok=user1_tok)
+        latest_event_id = event_response["event_id"]
+
+        response_body, from_token = self.do_sync(
+            sync_body, since=from_token, tok=user1_tok
+        )
+        room_response = response_body["rooms"][room_id1]
+
+        self.assertNotIn("initial", room_response)
+        self.assertNotIn("unstable_expanded_timeline", room_response)
+        self.assertEqual(room_response["limited"], False)
+
+        self._assertTimelineEqual(
+            room_id=room_id1,
+            actual_event_ids=[event["event_id"] for event in room_response["timeline"]],
+            expected_event_ids=[latest_event_id],
+            message=str(room_response["timeline"]),
+        )
+
+        # Increasing the limit to what it was before also should not resend any
+        # events
+        sync_body["room_subscriptions"] = {
+            room_id1: {
+                "required_state": [],
+                "timeline_limit": 10,
+            }
+        }
+
+        event_response = self.helper.send(room_id1, "msg", tok=user1_tok)
+        latest_event_id = event_response["event_id"]
+
+        response_body, from_token = self.do_sync(
+            sync_body, since=from_token, tok=user1_tok
+        )
+        room_response = response_body["rooms"][room_id1]
+
+        self.assertNotIn("initial", room_response)
+        self.assertNotIn("unstable_expanded_timeline", room_response)
+        self.assertEqual(room_response["limited"], False)
+
+        self._assertTimelineEqual(
+            room_id=room_id1,
+            actual_event_ids=[event["event_id"] for event in room_response["timeline"]],
+            expected_event_ids=[latest_event_id],
+            message=str(room_response["timeline"]),
+        )
--- a/tests/rest/client/utils.py
+++ b/tests/rest/client/utils.py
@ -45,7 +45,7 @@ from typing_extensions import Literal
 from twisted.test.proto_helpers import MemoryReactorClock
 from twisted.web.server import Site

-from synapse.api.constants import Membership
+from synapse.api.constants import Membership, ReceiptTypes
 from synapse.api.errors import Codes
 from synapse.server import HomeServer
 from synapse.types import JsonDict
@ -944,3 +944,15 @@ class RestHelper:
        assert len(p.links) == 1, "not exactly one link in confirmation page"
        oauth_uri = p.links[0]
        return oauth_uri
+
+    def send_read_receipt(self, room_id: str, event_id: str, *, tok: str) -> None:
+        """Send a read receipt into the room at the given event"""
+        channel = make_request(
+            self.reactor,
+            self.site,
+            method="POST",
+            path=f"/rooms/{room_id}/receipt/{ReceiptTypes.READ}/{event_id}",
+            content={},
+            access_token=tok,
+        )
+        assert channel.code == HTTPStatus.OK, channel.text_body
--- a/tests/server.py
+++ b/tests/server.py
@ -1166,6 +1166,12 @@ def setup_test_homeserver(

    hs.get_auth_handler().validate_hash = validate_hash  # type: ignore[assignment]

+    # We need to replace the media threadpool with the fake test threadpool.
+    def thread_pool() -> threadpool.ThreadPool:
+        return reactor.getThreadPool()
+
+    hs.get_media_sender_thread_pool = thread_pool  # type: ignore[method-assign]
+
    # Load any configured modules into the homeserver
    module_api = hs.get_module_api()
    for module, module_config in hs.config.modules.loaded_modules:
--- a/tests/storage/test_stream.py
+++ b/tests/storage/test_stream.py
@ -148,7 +148,7 @@ class PaginationTestCase(HomeserverTestCase):
        """Make a request to /messages with a filter, returns the chunk of events."""

        events, next_key = self.get_success(
-            self.hs.get_datastores().main.paginate_room_events(
+            self.hs.get_datastores().main.paginate_room_events_by_topological_ordering(
                room_id=self.room_id,
                from_key=self.from_token.room_key,
                to_key=None,