Add changelog entry

Remove support for PostgreSQL 13.
Further reduce cardinality of metrics on event persister (#19168 )
2025-12-05 01:10:13 +00:00 · 2025-11-12 13:27:45 -07:00 · 2025-11-12 13:24:43 -07:00 · 2025-11-12 16:40:38 +00:00 · 2025-11-12 16:37:14 +00:00 · 2025-11-12 13:41:58 +00:00
495 changed files with 5085 additions and 5344 deletions
--- a/.ci/scripts/auditwheel_wrapper.py
+++ b/.ci/scripts/auditwheel_wrapper.py
@@ -25,7 +25,6 @@
 import argparse
 import os
 import subprocess
-from typing import Optional
 from zipfile import ZipFile

 from packaging.tags import Tag
@@ -80,7 +79,7 @@ def cpython(wheel_file: str, name: str, version: Version, tag: Tag) -> str:
    return new_wheel_file


-def main(wheel_file: str, dest_dir: str, archs: Optional[str]) -> None:
+def main(wheel_file: str, dest_dir: str, archs: str | None) -> None:
    """Entry point"""

    # Parse the wheel file name into its parts. Note that `parse_wheel_filename`
--- a/.ci/scripts/calculate_jobs.py
+++ b/.ci/scripts/calculate_jobs.py
@@ -35,46 +35,55 @@ IS_PR = os.environ["GITHUB_REF"].startswith("refs/pull/")

 # First calculate the various trial jobs.
 #
-# For PRs, we only run each type of test with the oldest Python version supported (which
-# is Python 3.10 right now)
+# For PRs, we only run each type of test with the oldest and newest Python
+# version that's supported. The oldest version ensures we don't accidentally
+# introduce syntax or code that's too new, and the newest ensures we don't use
+# code that's been dropped in the latest supported Python version.

 trial_sqlite_tests = [
    {
        "python-version": "3.10",
        "database": "sqlite",
        "extras": "all",
-    }
+    },
+    {
+        "python-version": "3.14",
+        "database": "sqlite",
+        "extras": "all",
+    },
 ]

 if not IS_PR:
+    # Otherwise, check all supported Python versions.
+    #
+    # Avoiding running all of these versions on every PR saves on CI time.
    trial_sqlite_tests.extend(
        {
            "python-version": version,
            "database": "sqlite",
            "extras": "all",
        }
-        for version in ("3.11", "3.12", "3.13", "3.14")
+        for version in ("3.11", "3.12", "3.13")
    )

+# Only test postgres against the earliest and latest Python versions that we
+# support in order to save on CI time.
 trial_postgres_tests = [
    {
        "python-version": "3.10",
        "database": "postgres",
-        "postgres-version": "13",
+        "postgres-version": "14",
        "extras": "all",
-    }
+    },
+    {
+        "python-version": "3.14",
+        "database": "postgres",
+        "postgres-version": "17",
+        "extras": "all",
+    },
 ]

-if not IS_PR:
-    trial_postgres_tests.append(
-        {
-            "python-version": "3.14",
-            "database": "postgres",
-            "postgres-version": "17",
-            "extras": "all",
-        }
-    )
-
+# Ensure that Synapse passes unit tests even with no extra dependencies installed.
 trial_no_extra_tests = [
    {
        "python-version": "3.10",
--- a/.ci/scripts/prepare_old_deps.sh
+++ b/.ci/scripts/prepare_old_deps.sh
@@ -16,20 +16,23 @@ export VIRTUALENV_NO_DOWNLOAD=1
 # to select the lowest possible versions, rather than resorting to this sed script.

 # Patch the project definitions in-place:
-# - Replace all lower and tilde bounds with exact bounds
-# - Replace all caret bounds---but not the one that defines the supported Python version!
-# - Delete all lines referring to psycopg2 --- so no testing of postgres support.
+# - `-E` use extended regex syntax.
+# - Don't modify the line that defines required Python versions.
+# - Replace all lower and tilde bounds with exact bounds.
+# - Replace all caret bounds with exact bounds.
+# - Delete all lines referring to psycopg2 - so no testing of postgres support.
 # - Use pyopenssl 17.0, which is the oldest version that works with
 #   a `cryptography` compiled against OpenSSL 1.1.
 # - Omit systemd: we're not logging to journal here.

-sed -i \
-   -e "s/[~>]=/==/g" \
-   -e '/^python = "^/!s/\^/==/g' \
-   -e "/psycopg2/d" \
-   -e 's/pyOpenSSL = "==16.0.0"/pyOpenSSL = "==17.0.0"/' \
-   -e '/systemd/d' \
-   pyproject.toml
+sed -i -E '
+  /^\s*requires-python\s*=/b
+  s/[~>]=/==/g
+  s/\^/==/g
+  /psycopg2/d
+  s/pyOpenSSL\s*==\s*16\.0\.0"/pyOpenSSL==17.0.0"/
+  /systemd/d
+' pyproject.toml

 echo "::group::Patched pyproject.toml"
 cat pyproject.toml
--- a/.git-blame-ignore-revs
+++ b/.git-blame-ignore-revs
@@ -26,3 +26,8 @@ c4268e3da64f1abb5b31deaeb5769adb6510c0a7
 # Update black to 23.1.0 (https://github.com/matrix-org/synapse/pull/15103)
 9bb2eac71962970d02842bca441f4bcdbbf93a11

+# Use type hinting generics in standard collections (https://github.com/element-hq/synapse/pull/19046)
+fc244bb592aa481faf28214a2e2ce3bb4e95d990
+
+# Write union types as X | Y where possible (https://github.com/element-hq/synapse/pull/19111)
+fcac7e0282b074d4bd3414d1c9c181e9701875d9
--- a/.github/workflows/docker.yml
+++ b/.github/workflows/docker.yml
@@ -123,7 +123,7 @@ jobs:
        uses: sigstore/cosign-installer@faadad0cce49287aee09b3a48701e75088a2c6ad # v4.0.0

      - name: Calculate docker image tag
-        uses: docker/metadata-action@c1e51972afc2121e065aed6d45c65596fe445f3f # v5.8.0
+        uses: docker/metadata-action@318604b99e75e41977312d83839a89be02ca4893 # v5.9.0
        with:
          images: ${{ matrix.repository }}
          flavor: |
--- a/.github/workflows/push_complement_image.yml
+++ b/.github/workflows/push_complement_image.yml
@@ -55,7 +55,7 @@ jobs:
          password: ${{ secrets.GITHUB_TOKEN }}
      - name: Work out labels for complement image
        id: meta
-        uses: docker/metadata-action@c1e51972afc2121e065aed6d45c65596fe445f3f # v5.8.0
+        uses: docker/metadata-action@318604b99e75e41977312d83839a89be02ca4893 # v5.9.0
        with:
          images: ghcr.io/${{ github.repository }}/complement-synapse
          tags: |
--- a/.github/workflows/tests.yml
+++ b/.github/workflows/tests.yml
@@ -617,7 +617,7 @@ jobs:
      matrix:
        include:
          - python-version: "3.10"
-            postgres-version: "13"
+            postgres-version: "14"

          - python-version: "3.14"
            postgres-version: "17"
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -1,12 +1,3 @@
-# Synapse 1.142.1 (2025-11-18)
-
-## Bugfixes
-
- Fixed a bug introduced in v1.142.0 preventing subpaths in MAS endpoints from working. ([\#19186](https://github.com/element-hq/synapse/issues/19186))
-
-
-
-
 # Synapse 1.142.0 (2025-11-11)

 ## Dropped support for Python 3.9
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -851,9 +851,9 @@ dependencies = [

 [[package]]
 name = "pyo3-log"
-version = "0.13.1"
+version = "0.13.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "d359e20231345f21a3b5b6aea7e73f4dc97e1712ef3bfe2d88997ac6a308d784"
+checksum = "2f8bae9ad5ba08b0b0ed2bb9c2bdbaeccc69cafca96d78cf0fbcea0d45d122bb"
 dependencies = [
 "arc-swap",
 "log",
--- a/changelog.d/18784.feature
+++ b/changelog.d/18784.feature
@@ -0,0 +1 @@
+Support multiple config files in `register_new_matrix_user`.
--- a/changelog.d/18943.doc
+++ b/changelog.d/18943.doc
@@ -0,0 +1 @@
+Improve documentation around streams, particularly ID generators and adding new streams.
--- a/changelog.d/19111.misc
+++ b/changelog.d/19111.misc
@@ -0,0 +1 @@
+Write union types as `X | Y` where possible, as per PEP 604, added in Python 3.10.
--- a/changelog.d/19133.misc
+++ b/changelog.d/19133.misc
@@ -0,0 +1 @@
+Reduce cardinality of `synapse_storage_events_persisted_events_sep_total` metric by removing `origin_entity` label. This also separates out events sent by local application services by changing the `origin_type` for such events to `application_service`. The `type` field also only tracks common event types, and anything else is bucketed under `*other*`.
--- a/changelog.d/19135.misc
+++ b/changelog.d/19135.misc
@@ -0,0 +1 @@
+Run trial tests on Python 3.14 for PRs.
--- a/changelog.d/19137.misc
+++ b/changelog.d/19137.misc
@@ -0,0 +1 @@
+Update `pyproject.toml` project metadata to be compatible with standard Python packaging tooling.
--- a/changelog.d/19138.misc
+++ b/changelog.d/19138.misc
@@ -0,0 +1 @@
+Minor speed up of processing of inbound replication.
--- a/changelog.d/19145.misc
+++ b/changelog.d/19145.misc
@@ -0,0 +1 @@
+Minor speed up of processing of inbound replication.
--- a/changelog.d/19146.misc
+++ b/changelog.d/19146.misc
@@ -0,0 +1 @@
+Minor speed up of processing of inbound replication.
--- a/changelog.d/19150.misc
+++ b/changelog.d/19150.misc
@@ -0,0 +1 @@
+Ignore recent Python language refactors from git blame (`.git-blame-ignore-revs`).
--- a/changelog.d/19155.bugfix
+++ b/changelog.d/19155.bugfix
@@ -0,0 +1 @@
+Let the SQLite-to-PostgreSQL migration script correctly migrate a boolean column in the `delayed_events` table.
--- a/changelog.d/19167.misc
+++ b/changelog.d/19167.misc
@@ -0,0 +1 @@
+Bump lower bounds of dependencies `parameterized` to `0.9.0` and `idna` to `3.3` as those are the first to advertise support for Python 3.10.
--- a/changelog.d/19168.misc
+++ b/changelog.d/19168.misc
@@ -0,0 +1 @@
+Reduce cardinality of `synapse_storage_events_persisted_events_sep_total` metric by removing `origin_entity` label. This also separates out events sent by local application services by changing the `origin_type` for such events to `application_service`. The `type` field also only tracks common event types, and anything else is bucketed under `*other*`.
--- a/changelog.d/19170.removal
+++ b/changelog.d/19170.removal
@@ -0,0 +1 @@
+Remove support for PostgreSQL 13.
--- a/contrib/cmdclient/console.py
+++ b/contrib/cmdclient/console.py
@@ -33,7 +33,6 @@ import sys
 import time
 import urllib
 from http import TwistedHttpClient
-from typing import Optional

 import urlparse
 from signedjson.key import NACL_ED25519, decode_verify_key_bytes
@@ -726,7 +725,7 @@ class SynapseCmd(cmd.Cmd):
        method,
        path,
        data=None,
-        query_params: Optional[dict] = None,
+        query_params: dict | None = None,
        alt_text=None,
    ):
        """Runs an HTTP request and pretty prints the output.
--- a/contrib/cmdclient/http.py
+++ b/contrib/cmdclient/http.py
@@ -22,7 +22,6 @@
 import json
 import urllib
 from pprint import pformat
-from typing import Optional

 from twisted.internet import defer, reactor
 from twisted.web.client import Agent, readBody
@@ -90,7 +89,7 @@ class TwistedHttpClient(HttpClient):
        body = yield readBody(response)
        return json.loads(body)

-    def _create_put_request(self, url, json_data, headers_dict: Optional[dict] = None):
+    def _create_put_request(self, url, json_data, headers_dict: dict | None = None):
        """Wrapper of _create_request to issue a PUT request"""
        headers_dict = headers_dict or {}

@@ -101,7 +100,7 @@ class TwistedHttpClient(HttpClient):
            "PUT", url, producer=_JsonProducer(json_data), headers_dict=headers_dict
        )

-    def _create_get_request(self, url, headers_dict: Optional[dict] = None):
+    def _create_get_request(self, url, headers_dict: dict | None = None):
        """Wrapper of _create_request to issue a GET request"""
        return self._create_request("GET", url, headers_dict=headers_dict or {})

@@ -113,7 +112,7 @@ class TwistedHttpClient(HttpClient):
        data=None,
        qparams=None,
        jsonreq=True,
-        headers: Optional[dict] = None,
+        headers: dict | None = None,
    ):
        headers = headers or {}

@@ -138,7 +137,7 @@ class TwistedHttpClient(HttpClient):

    @defer.inlineCallbacks
    def _create_request(
-        self, method, url, producer=None, headers_dict: Optional[dict] = None
+        self, method, url, producer=None, headers_dict: dict | None = None
    ):
        """Creates and sends a request to the given url"""
        headers_dict = headers_dict or {}
--- a/contrib/grafana/synapse.json
+++ b/contrib/grafana/synapse.json
@@ -2166,10 +2166,10 @@
              "datasource": {
                "uid": "${DS_PROMETHEUS}"
              },
-              "expr": "rate(synapse_storage_events_persisted_by_source_type{instance=\"$instance\",job=~\"$job\",index=~\"$index\"}[$bucket_size])",
+              "expr": "rate(synapse_storage_events_persisted_events_sep_total{instance=\"$instance\",job=~\"$job\",index=~\"$index\"}[$bucket_size])",
              "format": "time_series",
              "intervalFactor": 2,
-              "legendFormat": "{{type}}",
+              "legendFormat": "{{origin_type}}",
              "refId": "D"
            }
          ],
@@ -2254,7 +2254,7 @@
              "datasource": {
                "uid": "${DS_PROMETHEUS}"
              },
-              "expr": "rate(synapse_storage_events_persisted_by_event_type{job=~\"$job\",index=~\"$index\",instance=\"$instance\"}[$bucket_size])",
+              "expr": "sum by(type) (rate(synapse_storage_events_persisted_events_sep_total{job=~\"$job\",index=~\"$index\",instance=\"$instance\"}[$bucket_size]))",
              "format": "time_series",
              "instant": false,
              "intervalFactor": 2,
@@ -2294,99 +2294,6 @@
            "align": false
          }
        },
-        {
-          "aliasColors": {
-            "irc-freenode (local)": "#EAB839"
-          },
-          "bars": false,
-          "dashLength": 10,
-          "dashes": false,
-          "datasource": {
-            "uid": "${DS_PROMETHEUS}"
-          },
-          "decimals": 1,
-          "fill": 1,
-          "fillGradient": 0,
-          "gridPos": {
-            "h": 7,
-            "w": 12,
-            "x": 0,
-            "y": 44
-          },
-          "hiddenSeries": false,
-          "id": 44,
-          "legend": {
-            "alignAsTable": true,
-            "avg": false,
-            "current": false,
-            "hideEmpty": true,
-            "hideZero": true,
-            "max": false,
-            "min": false,
-            "show": true,
-            "total": false,
-            "values": false
-          },
-          "lines": true,
-          "linewidth": 1,
-          "links": [],
-          "nullPointMode": "null",
-          "options": {
-            "alertThreshold": true
-          },
-          "percentage": false,
-          "pluginVersion": "9.2.2",
-          "pointradius": 5,
-          "points": false,
-          "renderer": "flot",
-          "seriesOverrides": [],
-          "spaceLength": 10,
-          "stack": false,
-          "steppedLine": false,
-          "targets": [
-            {
-              "datasource": {
-                "uid": "${DS_PROMETHEUS}"
-              },
-              "expr": "rate(synapse_storage_events_persisted_by_origin{job=~\"$job\",index=~\"$index\",instance=\"$instance\"}[$bucket_size])",
-              "format": "time_series",
-              "intervalFactor": 2,
-              "legendFormat": "{{origin_entity}} ({{origin_type}})",
-              "refId": "A",
-              "step": 20
-            }
-          ],
-          "thresholds": [],
-          "timeRegions": [],
-          "title": "Events/s by Origin",
-          "tooltip": {
-            "shared": false,
-            "sort": 2,
-            "value_type": "individual"
-          },
-          "type": "graph",
-          "xaxis": {
-            "mode": "time",
-            "show": true,
-            "values": []
-          },
-          "yaxes": [
-            {
-              "format": "hertz",
-              "logBase": 1,
-              "min": "0",
-              "show": true
-            },
-            {
-              "format": "short",
-              "logBase": 1,
-              "show": true
-            }
-          ],
-          "yaxis": {
-            "align": false
-          }
-        },
        {
          "aliasColors": {},
          "bars": false,
--- a/contrib/prometheus/synapse-v2.rules
+++ b/contrib/prometheus/synapse-v2.rules
@@ -44,31 +44,3 @@ groups:
  ###
  ### End of 'Prometheus Console Only' rules block
  ###
-
-
-  ###
-  ### Grafana Only
-  ### The following rules are only needed if you use the Grafana dashboard
-  ### in contrib/grafana/synapse.json
-  ###
-  - record: synapse_storage_events_persisted_by_source_type
-    expr: sum without(type, origin_type, origin_entity) (synapse_storage_events_persisted_events_sep_total{origin_type="remote"})
-    labels:
-      type: remote
-  - record: synapse_storage_events_persisted_by_source_type
-    expr: sum without(type, origin_type, origin_entity) (synapse_storage_events_persisted_events_sep_total{origin_entity="*client*",origin_type="local"})
-    labels:
-      type: local
-  - record: synapse_storage_events_persisted_by_source_type
-    expr: sum without(type, origin_type, origin_entity) (synapse_storage_events_persisted_events_sep_total{origin_entity!="*client*",origin_type="local"})
-    labels:
-      type: bridges
-
-  - record: synapse_storage_events_persisted_by_event_type
-    expr: sum without(origin_entity, origin_type) (synapse_storage_events_persisted_events_sep_total)
-
-  - record: synapse_storage_events_persisted_by_origin
-    expr: sum without(type) (synapse_storage_events_persisted_events_sep_total)
-  ###
-  ### End of 'Grafana Only' rules block
-  ###
--- a/debian/changelog
+++ b/debian/changelog
@@ -1,9 +1,3 @@
-matrix-synapse-py3 (1.142.1) stable; urgency=medium
-
-  * New Synapse release 1.142.1.
-
- -- Synapse Packaging team <packages@matrix.org>  Tue, 18 Nov 2025 12:25:23 -0700
-
 matrix-synapse-py3 (1.142.0) stable; urgency=medium

  * New Synapse release 1.142.0.
--- a/docker/complement/Dockerfile
+++ b/docker/complement/Dockerfile
@@ -11,7 +11,7 @@ ARG SYNAPSE_VERSION=latest
 ARG FROM=matrixdotorg/synapse-workers:$SYNAPSE_VERSION
 ARG DEBIAN_VERSION=trixie

-FROM docker.io/library/postgres:13-${DEBIAN_VERSION} AS postgres_base
+FROM docker.io/library/postgres:14-${DEBIAN_VERSION} AS postgres_base

 FROM $FROM
 # First of all, we copy postgres server from the official postgres image,
@@ -26,7 +26,7 @@ RUN adduser --system --uid 999 postgres --home /var/lib/postgresql
 COPY --from=postgres_base /usr/lib/postgresql /usr/lib/postgresql
 COPY --from=postgres_base /usr/share/postgresql /usr/share/postgresql
 COPY --from=postgres_base --chown=postgres /var/run/postgresql /var/run/postgresql
-ENV PATH="${PATH}:/usr/lib/postgresql/13/bin"
+ENV PATH="${PATH}:/usr/lib/postgresql/14/bin"
 ENV PGDATA=/var/lib/postgresql/data

 # We also initialize the database at build time, rather than runtime, so that it's faster to spin up the image.
--- a/docker/configure_workers_and_start.py
+++ b/docker/configure_workers_and_start.py
@@ -68,7 +68,6 @@ from typing import (
    Mapping,
    MutableMapping,
    NoReturn,
-    Optional,
    SupportsIndex,
 )

@@ -468,7 +467,7 @@ def add_worker_roles_to_shared_config(


 def merge_worker_template_configs(
-    existing_dict: Optional[dict[str, Any]],
+    existing_dict: dict[str, Any] | None,
    to_be_merged_dict: dict[str, Any],
 ) -> dict[str, Any]:
    """When given an existing dict of worker template configuration consisting with both
@@ -1026,7 +1025,7 @@ def generate_worker_log_config(
    Returns: the path to the generated file
    """
    # Check whether we should write worker logs to disk, in addition to the console
-    extra_log_template_args: dict[str, Optional[str]] = {}
+    extra_log_template_args: dict[str, str | None] = {}
    if environ.get("SYNAPSE_WORKERS_WRITE_LOGS_TO_DISK"):
        extra_log_template_args["LOG_FILE_PATH"] = f"{data_dir}/logs/{worker_name}.log"

--- a/docker/start.py
+++ b/docker/start.py
@@ -6,7 +6,7 @@ import os
 import platform
 import subprocess
 import sys
-from typing import Any, Mapping, MutableMapping, NoReturn, Optional
+from typing import Any, Mapping, MutableMapping, NoReturn

 import jinja2

@@ -50,7 +50,7 @@ def generate_config_from_template(
    config_dir: str,
    config_path: str,
    os_environ: Mapping[str, str],
-    ownership: Optional[str],
+    ownership: str | None,
 ) -> None:
    """Generate a homeserver.yaml from environment variables

@@ -147,7 +147,7 @@ def generate_config_from_template(
    subprocess.run(args, check=True)


-def run_generate_config(environ: Mapping[str, str], ownership: Optional[str]) -> None:
+def run_generate_config(environ: Mapping[str, str], ownership: str | None) -> None:
    """Run synapse with a --generate-config param to generate a template config file

    Args:
--- a/docs/development/synapse_architecture/cancellation.md
+++ b/docs/development/synapse_architecture/cancellation.md
@@ -299,7 +299,7 @@ logcontext is not finished before the `async` processing completes.

 **Bad**:
 ```python
-cache: Optional[ObservableDeferred[None]] = None
+cache: ObservableDeferred[None] | None = None

 async def do_something_else(
    to_resolve: Deferred[None]
@@ -326,7 +326,7 @@ with LoggingContext("request-1"):

 **Good**:
 ```python
-cache: Optional[ObservableDeferred[None]] = None
+cache: ObservableDeferred[None] | None = None

 async def do_something_else(
    to_resolve: Deferred[None]
@@ -358,7 +358,7 @@ with LoggingContext("request-1"):

 **OK**:
 ```python
-cache: Optional[ObservableDeferred[None]] = None
+cache: ObservableDeferred[None] | None = None

 async def do_something_else(
    to_resolve: Deferred[None]
--- a/docs/development/synapse_architecture/streams.md
+++ b/docs/development/synapse_architecture/streams.md
@@ -1,4 +1,4 @@
-## Streams
+# Streams

 Synapse has a concept of "streams", which are roughly described in [`id_generators.py`](
    https://github.com/element-hq/synapse/blob/develop/synapse/storage/util/id_generators.py
@@ -19,7 +19,7 @@ To that end, let's describe streams formally, paraphrasing from the docstring of
    https://github.com/element-hq/synapse/blob/a719b703d9bd0dade2565ddcad0e2f3a7a9d4c37/synapse/storage/util/id_generators.py#L96
 ).

-### Definition
+## Definition

 A stream is an append-only log `T1, T2, ..., Tn, ...` of facts[^1] which grows over time.
 Only "writers" can add facts to a stream, and there may be multiple writers.
@@ -47,7 +47,7 @@ But unhappy cases (e.g. transaction rollback due to an error) also count as comp
 Once completed, the rows written with that stream ID are fixed, and no new rows
 will be inserted with that ID.

-### Current stream ID
+## Current stream ID

 For any given stream reader (including writers themselves), we may define a per-writer current stream ID:

@@ -93,7 +93,7 @@ Consider a single-writer stream which is initially at ID 1.
 | Complete 6 | 6                 |                                                 |


-### Multi-writer streams
+## Multi-writer streams

 There are two ways to view a multi-writer stream.

@@ -115,7 +115,7 @@ The facts this stream holds are instructions to "you should now invalidate these
 We only ever treat this as a multiple single-writer streams as there is no important ordering between cache invalidations.
 (Invalidations are self-contained facts; and the invalidations commute/are idempotent).

-### Writing to streams
+## Writing to streams

 Writers need to track:
 - track their current position (i.e. its own per-writer stream ID).
@@ -133,7 +133,7 @@ To complete a fact, first remove it from your map of facts currently awaiting co
 Then, if no earlier fact is awaiting completion, the writer can advance its current position in that stream.
 Upon doing so it should emit an `RDATA` message[^3], once for every fact between the old and the new stream ID.

-### Subscribing to streams
+## Subscribing to streams

 Readers need to track the current position of every writer.

@@ -146,10 +146,44 @@ The `RDATA` itself is not a self-contained representation of the fact;
 readers will have to query the stream tables for the full details.
 Readers must also advance their record of the writer's current position for that stream.

-# Summary
+## Summary

 In a nutshell: we have an append-only log with a "buffer/scratchpad" at the end where we have to wait for the sequence to be linear and contiguous.

+---
+
+## Cheatsheet for creating a new stream
+
+These rough notes and links may help you to create a new stream and add all the
+necessary registration and event handling.
+
+**Create your stream:**
+- [create a stream class and stream row class](https://github.com/element-hq/synapse/blob/4367fb2d078c52959aeca0fe6874539c53e8360d/synapse/replication/tcp/streams/_base.py#L728)
+  - will need an [ID generator](https://github.com/element-hq/synapse/blob/4367fb2d078c52959aeca0fe6874539c53e8360d/synapse/storage/databases/main/thread_subscriptions.py#L75)
+    - may need [writer configuration](https://github.com/element-hq/synapse/blob/4367fb2d078c52959aeca0fe6874539c53e8360d/synapse/config/workers.py#L177), if there isn't already an obvious source of configuration for which workers should be designated as writers to your new stream.
+      - if adding new writer configuration, add Docker-worker configuration, which lets us configure the writer worker in Complement tests: [[1]](https://github.com/element-hq/synapse/blob/4367fb2d078c52959aeca0fe6874539c53e8360d/docker/configure_workers_and_start.py#L331), [[2]](https://github.com/element-hq/synapse/blob/4367fb2d078c52959aeca0fe6874539c53e8360d/docker/configure_workers_and_start.py#L440)
+- most of the time, you will likely introduce a new datastore class for the concept represented by the new stream, unless there is already an obvious datastore that covers it.
+- consider whether it may make sense to introduce a handler
+
+**Register your stream in:**
+- [`STREAMS_MAP`](https://github.com/element-hq/synapse/blob/4367fb2d078c52959aeca0fe6874539c53e8360d/synapse/replication/tcp/streams/__init__.py#L71)
+
+**Advance your stream in:**
+- [`process_replication_position` of your appropriate datastore](https://github.com/element-hq/synapse/blob/4367fb2d078c52959aeca0fe6874539c53e8360d/synapse/storage/databases/main/thread_subscriptions.py#L111)
+  - don't forget the super call
+
+**If you're going to do any caching that needs invalidation from new rows:**
+- add invalidations to [`process_replication_rows` of your appropriate datastore](https://github.com/element-hq/synapse/blob/4367fb2d078c52959aeca0fe6874539c53e8360d/synapse/storage/databases/main/thread_subscriptions.py#L91)
+  - don't forget the super call
+- add local-only [invalidations to your writer transactions](https://github.com/element-hq/synapse/blob/4367fb2d078c52959aeca0fe6874539c53e8360d/synapse/storage/databases/main/thread_subscriptions.py#L201)
+
+**For streams to be used in sync:**
+- add a new field to [`StreamToken`](https://github.com/element-hq/synapse/blob/4367fb2d078c52959aeca0fe6874539c53e8360d/synapse/types/__init__.py#L1003)
+  - add a new [`StreamKeyType`](https://github.com/element-hq/synapse/blob/4367fb2d078c52959aeca0fe6874539c53e8360d/synapse/types/__init__.py#L999)
+- add appropriate wake-up rules
+  - in [`on_rdata`](https://github.com/element-hq/synapse/blob/4367fb2d078c52959aeca0fe6874539c53e8360d/synapse/replication/tcp/client.py#L260)
+  - locally on the same worker when completing a write, [e.g. in your handler](https://github.com/element-hq/synapse/blob/4367fb2d078c52959aeca0fe6874539c53e8360d/synapse/handlers/thread_subscriptions.py#L139)
+- add the stream in [`bound_future_token`](https://github.com/element-hq/synapse/blob/4367fb2d078c52959aeca0fe6874539c53e8360d/synapse/streams/events.py#L127)

 ---

--- a/docs/modules/account_data_callbacks.md
+++ b/docs/modules/account_data_callbacks.md
@@ -15,7 +15,7 @@ _First introduced in Synapse v1.57.0_
 ```python
 async def on_account_data_updated(
    user_id: str,
-    room_id: Optional[str],
+    room_id: str | None,
    account_data_type: str,
    content: "synapse.module_api.JsonDict",
 ) -> None:
@@ -82,7 +82,7 @@ class CustomAccountDataModule:
    async def log_new_account_data(
        self,
        user_id: str,
-        room_id: Optional[str],
+        room_id: str | None,
        account_data_type: str,
        content: JsonDict,
    ) -> None:
--- a/docs/modules/account_validity_callbacks.md
+++ b/docs/modules/account_validity_callbacks.md
@@ -12,7 +12,7 @@ The available account validity callbacks are:
 _First introduced in Synapse v1.39.0_

 ```python
-async def is_user_expired(user: str) -> Optional[bool]
+async def is_user_expired(user: str) -> bool | None
 ```

 Called when processing any authenticated request (except for logout requests). The module
--- a/docs/modules/media_repository_callbacks.md
+++ b/docs/modules/media_repository_callbacks.md
@@ -11,7 +11,7 @@ The available media repository callbacks are:
 _First introduced in Synapse v1.132.0_

 ```python
-async def get_media_config_for_user(user_id: str) -> Optional[JsonDict]
+async def get_media_config_for_user(user_id: str) -> JsonDict | None
 ```

 **<span style="color:red">
@@ -70,7 +70,7 @@ implementations of this callback.
 _First introduced in Synapse v1.139.0_

 ```python
-async def get_media_upload_limits_for_user(user_id: str, size: int) -> Optional[List[synapse.module_api.MediaUploadLimit]]
+async def get_media_upload_limits_for_user(user_id: str, size: int) -> list[synapse.module_api.MediaUploadLimit] | None
 ```

 **<span style="color:red">
--- a/docs/modules/password_auth_provider_callbacks.md
+++ b/docs/modules/password_auth_provider_callbacks.md
@@ -23,12 +23,7 @@ async def check_auth(
    user: str,
    login_type: str,
    login_dict: "synapse.module_api.JsonDict",
-) -> Optional[
-    Tuple[
-        str, 
-        Optional[Callable[["synapse.module_api.LoginResponse"], Awaitable[None]]]
-    ]
-]
+) -> tuple[str, Callable[["synapse.module_api.LoginResponse"], Awaitable[None]] | None] | None
 ```

 The login type and field names should be provided by the user in the
@@ -67,12 +62,7 @@ async def check_3pid_auth(
    medium: str, 
    address: str,
    password: str,
-) -> Optional[
-    Tuple[
-        str, 
-        Optional[Callable[["synapse.module_api.LoginResponse"], Awaitable[None]]]
-    ]
-]
+) -> tuple[str, Callable[["synapse.module_api.LoginResponse"], Awaitable[None]] | None]
 ```

 Called when a user attempts to register or log in with a third party identifier,
@@ -98,7 +88,7 @@ _First introduced in Synapse v1.46.0_
 ```python
 async def on_logged_out(
    user_id: str,
-    device_id: Optional[str],
+    device_id: str | None,
    access_token: str
 ) -> None
 ``` 
@@ -119,7 +109,7 @@ _First introduced in Synapse v1.52.0_
 async def get_username_for_registration(
    uia_results: Dict[str, Any],
    params: Dict[str, Any],
-) -> Optional[str]
+) -> str | None
 ```

 Called when registering a new user. The module can return a username to set for the user
@@ -180,7 +170,7 @@ _First introduced in Synapse v1.54.0_
 async def get_displayname_for_registration(
    uia_results: Dict[str, Any],
    params: Dict[str, Any],
-) -> Optional[str]
+) -> str | None
 ```

 Called when registering a new user. The module can return a display name to set for the
@@ -259,12 +249,7 @@ class MyAuthProvider:
        username: str,
        login_type: str,
        login_dict: "synapse.module_api.JsonDict",
-    ) -> Optional[
-        Tuple[
-            str,
-            Optional[Callable[["synapse.module_api.LoginResponse"], Awaitable[None]]],
-        ]
-    ]:
+    ) -> tuple[str, Callable[["synapse.module_api.LoginResponse"], Awaitable[None]] | None] | None:
        if login_type != "my.login_type":
            return None

@@ -276,12 +261,7 @@ class MyAuthProvider:
        username: str,
        login_type: str,
        login_dict: "synapse.module_api.JsonDict",
-    ) -> Optional[
-        Tuple[
-            str,
-            Optional[Callable[["synapse.module_api.LoginResponse"], Awaitable[None]]],
-        ]
-    ]:
+    ) -> tuple[str, Callable[["synapse.module_api.LoginResponse"], Awaitable[None]] | None] | None:
        if login_type != "m.login.password":
            return None

--- a/docs/modules/presence_router_callbacks.md
+++ b/docs/modules/presence_router_callbacks.md
@@ -23,7 +23,7 @@ _First introduced in Synapse v1.42.0_
 ```python 
 async def get_users_for_states(
    state_updates: Iterable["synapse.api.UserPresenceState"],
-) -> Dict[str, Set["synapse.api.UserPresenceState"]]
+) -> dict[str, set["synapse.api.UserPresenceState"]]
 ```
 **Requires** `get_interested_users` to also be registered

@@ -45,7 +45,7 @@ _First introduced in Synapse v1.42.0_
 ```python
 async def get_interested_users(
    user_id: str
-) -> Union[Set[str], "synapse.module_api.PRESENCE_ALL_USERS"]
+) -> set[str] | "synapse.module_api.PRESENCE_ALL_USERS"
 ```
 **Requires** `get_users_for_states` to also be registered

@@ -73,7 +73,7 @@ that `@alice:example.org` receives all presence updates from `@bob:example.com`
 `@charlie:somewhere.org`, regardless of whether Alice shares a room with any of them.

 ```python
-from typing import Dict, Iterable, Set, Union
+from typing import Iterable

 from synapse.module_api import ModuleApi

@@ -90,7 +90,7 @@ class CustomPresenceRouter:
    async def get_users_for_states(
        self,
        state_updates: Iterable["synapse.api.UserPresenceState"],
-    ) -> Dict[str, Set["synapse.api.UserPresenceState"]]:
+    ) -> dict[str, set["synapse.api.UserPresenceState"]]:
        res = {}
        for update in state_updates:
            if (
@@ -104,7 +104,7 @@ class CustomPresenceRouter:
    async def get_interested_users(
        self,
        user_id: str,
-    ) -> Union[Set[str], "synapse.module_api.PRESENCE_ALL_USERS"]:
+    ) -> set[str] | "synapse.module_api.PRESENCE_ALL_USERS":
        if user_id == "@alice:example.com":
            return {"@bob:example.com", "@charlie:somewhere.org"}

--- a/docs/modules/ratelimit_callbacks.md
+++ b/docs/modules/ratelimit_callbacks.md
@@ -11,7 +11,7 @@ The available ratelimit callbacks are:
 _First introduced in Synapse v1.132.0_

 ```python
-async def get_ratelimit_override_for_user(user: str, limiter_name: str) -> Optional[synapse.module_api.RatelimitOverride]
+async def get_ratelimit_override_for_user(user: str, limiter_name: str) -> synapse.module_api.RatelimitOverride | None
 ```

 **<span style="color:red">
--- a/docs/modules/spam_checker_callbacks.md
+++ b/docs/modules/spam_checker_callbacks.md
@@ -331,9 +331,9 @@ search results; otherwise return `False`.
 The profile is represented as a dictionary with the following keys:

 * `user_id: str`. The Matrix ID for this user.
-* `display_name: Optional[str]`. The user's display name, or `None` if this user
+* `display_name: str | None`. The user's display name, or `None` if this user
  has not set a display name.
-* `avatar_url: Optional[str]`. The `mxc://` URL to the user's avatar, or `None`
+* `avatar_url: str | None`. The `mxc://` URL to the user's avatar, or `None`
  if this user has not set an avatar.

 The module is given a copy of the original dictionary, so modifying it from within the
@@ -352,10 +352,10 @@ _First introduced in Synapse v1.37.0_

 ```python
 async def check_registration_for_spam(
-    email_threepid: Optional[dict],
-    username: Optional[str],
+    email_threepid: dict | None,
+    username: str | None,
    request_info: Collection[Tuple[str, str]],
-    auth_provider_id: Optional[str] = None,
+    auth_provider_id: str | None = None,
 ) -> "synapse.spam_checker_api.RegistrationBehaviour"
 ```

@@ -438,10 +438,10 @@ _First introduced in Synapse v1.87.0_
 ```python
 async def check_login_for_spam(
    user_id: str,
-    device_id: Optional[str],
-    initial_display_name: Optional[str],
-    request_info: Collection[Tuple[Optional[str], str]],
-    auth_provider_id: Optional[str] = None,
+    device_id: str | None,
+    initial_display_name: str | None,
+    request_info: Collection[tuple[str | None, str]],
+    auth_provider_id: str | None = None,
 ) -> Union["synapse.module_api.NOT_SPAM", "synapse.module_api.errors.Codes"]
 ```

@@ -509,7 +509,7 @@ class ListSpamChecker:
            resource=IsUserEvilResource(config),
        )

-    async def check_event_for_spam(self, event: "synapse.events.EventBase") -> Union[Literal["NOT_SPAM"], Codes]:
+    async def check_event_for_spam(self, event: "synapse.events.EventBase") -> Literal["NOT_SPAM"] | Codes:
        if event.sender in self.evil_users:
          return Codes.FORBIDDEN
        else:
--- a/docs/modules/third_party_rules_callbacks.md
+++ b/docs/modules/third_party_rules_callbacks.md
@@ -16,7 +16,7 @@ _First introduced in Synapse v1.39.0_
 async def check_event_allowed(
    event: "synapse.events.EventBase",
    state_events: "synapse.types.StateMap",
-) -> Tuple[bool, Optional[dict]]
+) -> tuple[bool, dict | None]
 ```

 **<span style="color:red">
@@ -340,7 +340,7 @@ class EventCensorer:
        self,
        event: "synapse.events.EventBase",
        state_events: "synapse.types.StateMap",
-    ) -> Tuple[bool, Optional[dict]]:
+    ) -> Tuple[bool, dict | None]:
        event_dict = event.get_dict()
        new_event_content = await self.api.http_client.post_json_get_json(
            uri=self._endpoint, post_json=event_dict,
--- a/docs/presence_router_module.md
+++ b/docs/presence_router_module.md
@@ -76,7 +76,7 @@ possible.
 #### `get_interested_users`

 ```python
-async def get_interested_users(self, user_id: str) -> Union[Set[str], str]
+async def get_interested_users(self, user_id: str) -> set[str] | str
 ```

 **Required.** An asynchronous method that is passed a single Matrix User ID. This
@@ -182,7 +182,7 @@ class ExamplePresenceRouter:
    async def get_interested_users(
        self,
        user_id: str,
-    ) -> Union[Set[str], PresenceRouter.ALL_USERS]:
+    ) -> set[str] | PresenceRouter.ALL_USERS:
        """
        Retrieve a list of users that `user_id` is interested in receiving the
        presence of. This will be in addition to those they share a room with.
--- a/docs/reverse_proxy.md
+++ b/docs/reverse_proxy.md
@@ -86,6 +86,45 @@ server {
 }
 ```

+### Nginx Proxy Manager or NPMPlus
+
+```nginx
+Add New Proxy-Host
+	- Tab Details
+		- Domain Names: matrix.example.com
+		- Scheme: http
+		- Forward Hostname / IP: localhost # IP address or hostname where Synapse is hosted. Bare-metal or Container.
+		- Forward Port: 8008
+
+	- Tab Custom locations
+		- Add Location
+		- Define Location: /_matrix
+		- Scheme: http
+		- Forward Hostname / IP: localhost # IP address or hostname where Synapse is hosted. Bare-metal or Container.
+		- Forward Port: 8008
+		- Click on the gear icon to display a custom configuration field. Increase client_max_body_size to match max_upload_size defined in homeserver.yaml
+			- Enter this in the Custom Field: client_max_body_size 50M;
+
+	- Tab SSL/TLS
+		- Choose your SSL/TLS certificate and preferred settings.
+
+	- Tab Advanced
+		- Enter this in the Custom Field. This means that port 8448 no longer needs to be opened in your Firewall.
+		  The Federation communication use now Port 443.
+
+			location /.well-known/matrix/server {
+			  return 200 '{"m.server": "matrix.example.com:443"}';
+      		  add_header Content-Type application/json;
+			}
+
+ 			location /.well-known/matrix/client {
+      		  return 200 '{"m.homeserver": {"base_url": "https://matrix.example.com"}}';
+      		  add_header Content-Type application/json;
+      		  add_header "Access-Control-Allow-Origin" *;
+			}
+
+```
+
 ### Caddy v2

 ```
--- a/docs/upgrade.md
+++ b/docs/upgrade.md
@@ -117,6 +117,14 @@ each upgrade are complete before moving on to the next upgrade, to avoid
 stacking them up. You can monitor the currently running background updates with
 [the Admin API](usage/administration/admin_api/background_updates.html#status).

+# Upgrading to v1.143.0
+
+## Dropping support for PostgreSQL 13
+
+In line with our [deprecation policy](deprecation_policy.md), we've dropped
+support for PostgreSQL 13, as it is no longer supported upstream.
+This release of Synapse requires PostgreSQL 14+.
+
 # Upgrading to v1.142.0

 ## Python 3.10+ is now required
--- a/poetry.lock
+++ b/poetry.lock
@@ -39,7 +39,7 @@ description = "The ultimate Python library in building OAuth and OpenID Connect
 optional = true
 python-versions = ">=3.9"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"jwt\" or extra == \"oidc\""
+markers = "extra == \"oidc\" or extra == \"jwt\" or extra == \"all\""
 files = [
    {file = "authlib-1.6.5-py2.py3-none-any.whl", hash = "sha256:3e0e0507807f842b02175507bdee8957a1d5707fd4afb17c32fb43fee90b6e3a"},
    {file = "authlib-1.6.5.tar.gz", hash = "sha256:6aaf9c79b7cc96c900f0b284061691c5d4e61221640a948fe690b556a6d6d10b"},
@@ -389,52 +389,62 @@ files = [

 [[package]]
 name = "cryptography"
-version = "43.0.3"
+version = "45.0.7"
 description = "cryptography is a package which provides cryptographic recipes and primitives to Python developers."
 optional = false
-python-versions = ">=3.7"
+python-versions = "!=3.9.0,!=3.9.1,>=3.7"
 groups = ["main", "dev"]
 files = [
-    {file = "cryptography-43.0.3-cp37-abi3-macosx_10_9_universal2.whl", hash = "sha256:bf7a1932ac4176486eab36a19ed4c0492da5d97123f1406cf15e41b05e787d2e"},
-    {file = "cryptography-43.0.3-cp37-abi3-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:63efa177ff54aec6e1c0aefaa1a241232dcd37413835a9b674b6e3f0ae2bfd3e"},
-    {file = "cryptography-43.0.3-cp37-abi3-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:7e1ce50266f4f70bf41a2c6dc4358afadae90e2a1e5342d3c08883df1675374f"},
-    {file = "cryptography-43.0.3-cp37-abi3-manylinux_2_28_aarch64.whl", hash = "sha256:443c4a81bb10daed9a8f334365fe52542771f25aedaf889fd323a853ce7377d6"},
-    {file = "cryptography-43.0.3-cp37-abi3-manylinux_2_28_x86_64.whl", hash = "sha256:74f57f24754fe349223792466a709f8e0c093205ff0dca557af51072ff47ab18"},
-    {file = "cryptography-43.0.3-cp37-abi3-musllinux_1_2_aarch64.whl", hash = "sha256:9762ea51a8fc2a88b70cf2995e5675b38d93bf36bd67d91721c309df184f49bd"},
-    {file = "cryptography-43.0.3-cp37-abi3-musllinux_1_2_x86_64.whl", hash = "sha256:81ef806b1fef6b06dcebad789f988d3b37ccaee225695cf3e07648eee0fc6b73"},
-    {file = "cryptography-43.0.3-cp37-abi3-win32.whl", hash = "sha256:cbeb489927bd7af4aa98d4b261af9a5bc025bd87f0e3547e11584be9e9427be2"},
-    {file = "cryptography-43.0.3-cp37-abi3-win_amd64.whl", hash = "sha256:f46304d6f0c6ab8e52770addfa2fc41e6629495548862279641972b6215451cd"},
-    {file = "cryptography-43.0.3-cp39-abi3-macosx_10_9_universal2.whl", hash = "sha256:8ac43ae87929a5982f5948ceda07001ee5e83227fd69cf55b109144938d96984"},
-    {file = "cryptography-43.0.3-cp39-abi3-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:846da004a5804145a5f441b8530b4bf35afbf7da70f82409f151695b127213d5"},
-    {file = "cryptography-43.0.3-cp39-abi3-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:0f996e7268af62598f2fc1204afa98a3b5712313a55c4c9d434aef49cadc91d4"},
-    {file = "cryptography-43.0.3-cp39-abi3-manylinux_2_28_aarch64.whl", hash = "sha256:f7b178f11ed3664fd0e995a47ed2b5ff0a12d893e41dd0494f406d1cf555cab7"},
-    {file = "cryptography-43.0.3-cp39-abi3-manylinux_2_28_x86_64.whl", hash = "sha256:c2e6fc39c4ab499049df3bdf567f768a723a5e8464816e8f009f121a5a9f4405"},
-    {file = "cryptography-43.0.3-cp39-abi3-musllinux_1_2_aarch64.whl", hash = "sha256:e1be4655c7ef6e1bbe6b5d0403526601323420bcf414598955968c9ef3eb7d16"},
-    {file = "cryptography-43.0.3-cp39-abi3-musllinux_1_2_x86_64.whl", hash = "sha256:df6b6c6d742395dd77a23ea3728ab62f98379eff8fb61be2744d4679ab678f73"},
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 [package.dependencies]
-cffi = {version = ">=1.12", markers = "platform_python_implementation != \"PyPy\""}
+cffi = {version = ">=1.14", markers = "platform_python_implementation != \"PyPy\""}

 [package.extras]
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-nox = ["nox"]
-pep8test = ["check-sdist", "click", "mypy", "ruff"]
-sdist = ["build"]
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+sdist = ["build (>=1.0.0)"]
 ssh = ["bcrypt (>=3.1.5)"]
-test = ["certifi", "cryptography-vectors (==43.0.3)", "pretend", "pytest (>=6.2.0)", "pytest-benchmark", "pytest-cov", "pytest-xdist"]
+test = ["certifi (>=2024)", "cryptography-vectors (==45.0.7)", "pretend (>=0.7)", "pytest (>=7.4.0)", "pytest-benchmark (>=4.0)", "pytest-cov (>=2.10.1)", "pytest-xdist (>=3.5.0)"]
 test-randomorder = ["pytest-randomly"]

 [[package]]
@@ -444,7 +454,7 @@ description = "XML bomb protection for Python stdlib modules"
 optional = true
 python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"saml2\""
+markers = "extra == \"saml2\" or extra == \"all\""
 files = [
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@@ -469,7 +479,7 @@ description = "XPath 1.0/2.0/3.0/3.1 parsers and selectors for ElementTree and l
 optional = true
 python-versions = ">=3.7"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"saml2\""
+markers = "extra == \"saml2\" or extra == \"all\""
 files = [
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@@ -519,7 +529,7 @@ description = "Python wrapper for hiredis"
 optional = true
 python-versions = ">=3.8"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"redis\""
+markers = "extra == \"redis\" or extra == \"all\""
 files = [
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@@ -785,14 +795,14 @@ files = [

 [[package]]
 name = "immutabledict"
-version = "4.2.1"
+version = "4.2.2"
 description = "Immutable wrapper around dictionaries (a fork of frozendict)"
 optional = false
-python-versions = ">=3.8"
+python-versions = "<4.0,>=3.8"
 groups = ["main"]
 files = [
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+    {file = "immutabledict-4.2.2.tar.gz", hash = "sha256:cb6ed3090df593148f94cb407d218ca526fd2639694afdb553dc4f50ce6feeca"},
 ]

 [[package]]
@@ -802,7 +812,7 @@ description = "Read metadata from Python packages"
 optional = false
 python-versions = ">=3.7"
 groups = ["dev"]
-markers = "platform_machine != \"ppc64le\" and platform_machine != \"s390x\" and python_version < \"3.12\""
+markers = "python_version < \"3.12\" and platform_machine != \"ppc64le\" and platform_machine != \"s390x\""
 files = [
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@@ -842,7 +852,7 @@ description = "Jaeger Python OpenTracing Tracer implementation"
 optional = true
 python-versions = ">=3.7"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"opentracing\""
+markers = "extra == \"opentracing\" or extra == \"all\""
 files = [
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 ]
@@ -935,14 +945,14 @@ format-nongpl = ["fqdn", "idna", "isoduration", "jsonpointer (>1.13)", "rfc3339-

 [[package]]
 name = "jsonschema-specifications"
-version = "2023.6.1"
+version = "2023.7.1"
 description = "The JSON Schema meta-schemas and vocabularies, exposed as a Registry"
 optional = false
 python-versions = ">=3.8"
 groups = ["main"]
 files = [
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+    {file = "jsonschema_specifications-2023.7.1.tar.gz", hash = "sha256:c91a50404e88a1f6ba40636778e2ee08f6e24c5613fe4c53ac24578a5a7f72bb"},
 ]

 [package.dependencies]
@@ -980,7 +990,7 @@ description = "A strictly RFC 4510 conforming LDAP V3 pure Python client library
 optional = true
 python-versions = "*"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"matrix-synapse-ldap3\""
+markers = "extra == \"matrix-synapse-ldap3\" or extra == \"all\""
 files = [
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@@ -996,7 +1006,7 @@ description = "Powerful and Pythonic XML processing library combining libxml2/li
 optional = true
 python-versions = ">=3.8"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"url-preview\""
+markers = "extra == \"url-preview\" or extra == \"all\""
 files = [
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@@ -1282,7 +1292,7 @@ description = "An LDAP3 auth provider for Synapse"
 optional = true
 python-versions = ">=3.7"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"matrix-synapse-ldap3\""
+markers = "extra == \"matrix-synapse-ldap3\" or extra == \"all\""
 files = [
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@@ -1395,18 +1405,18 @@ files = [

 [[package]]
 name = "multipart"
-version = "1.2.1"
+version = "1.3.0"
 description = "Parser for multipart/form-data"
 optional = false
 python-versions = ">=3.8"
 groups = ["main"]
 files = [
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+    {file = "multipart-1.3.0-py3-none-any.whl", hash = "sha256:439bf4b00fd7cb2dbff08ae13f49f4f49798931ecd8d496372c63537fa19f304"},
+    {file = "multipart-1.3.0.tar.gz", hash = "sha256:a46bd6b0eb4c1ba865beb88ddd886012a3da709b6e7b86084fc37e99087e5cf1"},
 ]

 [package.extras]
-dev = ["build", "pytest", "pytest-cov", "twine"]
+dev = ["build", "pytest", "pytest-cov", "tox", "tox-uv", "twine"]
 docs = ["sphinx (>=8,<9)", "sphinx-autobuild"]

 [[package]]
@@ -1524,7 +1534,7 @@ description = "OpenTracing API for Python. See documentation at http://opentraci
 optional = true
 python-versions = "*"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"opentracing\""
+markers = "extra == \"opentracing\" or extra == \"all\""
 files = [
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@@ -1573,139 +1583,123 @@ files = [

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-typing = ["typing-extensions ; python_version < \"3.10\""]
+test-arrow = ["arro3-compute", "arro3-core", "nanoarrow", "pyarrow"]
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 xmp = ["defusedxml"]

 [[package]]
@@ -1730,7 +1724,7 @@ description = "psycopg2 - Python-PostgreSQL Database Adapter"
 optional = true
 python-versions = ">=3.9"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"postgres\""
+markers = "extra == \"postgres\" or extra == \"all\""
 files = [
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@@ -1748,7 +1742,7 @@ description = ".. image:: https://travis-ci.org/chtd/psycopg2cffi.svg?branch=mas
 optional = true
 python-versions = "*"
 groups = ["main"]
-markers = "platform_python_implementation == \"PyPy\" and (extra == \"all\" or extra == \"postgres\")"
+markers = "platform_python_implementation == \"PyPy\" and (extra == \"postgres\" or extra == \"all\")"
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 optional = true
 python-versions = "*"
 groups = ["main"]
-markers = "platform_python_implementation == \"PyPy\" and (extra == \"all\" or extra == \"postgres\")"
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+    {file = "pydantic_core-2.41.5-pp311-pypy311_pp73-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:58133647260ea01e4d0500089a8c4f07bd7aa6ce109682b1426394988d8aaacc"},
+    {file = "pydantic_core-2.41.5-pp311-pypy311_pp73-manylinux_2_5_i686.manylinux1_i686.whl", hash = "sha256:287dad91cfb551c363dc62899a80e9e14da1f0e2b6ebde82c806612ca2a13ef1"},
+    {file = "pydantic_core-2.41.5-pp311-pypy311_pp73-musllinux_1_1_aarch64.whl", hash = "sha256:03b77d184b9eb40240ae9fd676ca364ce1085f203e1b1256f8ab9984dca80a84"},
+    {file = "pydantic_core-2.41.5-pp311-pypy311_pp73-musllinux_1_1_armv7l.whl", hash = "sha256:a668ce24de96165bb239160b3d854943128f4334822900534f2fe947930e5770"},
+    {file = "pydantic_core-2.41.5-pp311-pypy311_pp73-musllinux_1_1_x86_64.whl", hash = "sha256:f14f8f046c14563f8eb3f45f499cc658ab8d10072961e07225e507adb700e93f"},
+    {file = "pydantic_core-2.41.5-pp311-pypy311_pp73-win_amd64.whl", hash = "sha256:56121965f7a4dc965bff783d70b907ddf3d57f6eba29b6d2e5dabfaf07799c51"},
+    {file = "pydantic_core-2.41.5.tar.gz", hash = "sha256:08daa51ea16ad373ffd5e7606252cc32f07bc72b28284b6bc9c6df804816476e"},
 ]

 [package.dependencies]
@@ -2041,7 +2039,7 @@ description = "A development tool to measure, monitor and analyze the memory beh
 optional = true
 python-versions = ">=3.6"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"cache-memory\""
+markers = "extra == \"cache-memory\" or extra == \"all\""
 files = [
    {file = "Pympler-1.0.1-py3-none-any.whl", hash = "sha256:d260dda9ae781e1eab6ea15bacb84015849833ba5555f141d2d9b7b7473b307d"},
    {file = "Pympler-1.0.1.tar.gz", hash = "sha256:993f1a3599ca3f4fcd7160c7545ad06310c9e12f70174ae7ae8d4e25f6c5d3fa"},
@@ -2101,7 +2099,7 @@ description = "Python implementation of SAML Version 2 Standard"
 optional = true
 python-versions = ">=3.9,<4.0"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"saml2\""
+markers = "extra == \"saml2\" or extra == \"all\""
 files = [
    {file = "pysaml2-7.5.0-py3-none-any.whl", hash = "sha256:bc6627cc344476a83c757f440a73fda1369f13b6fda1b4e16bca63ffbabb5318"},
    {file = "pysaml2-7.5.0.tar.gz", hash = "sha256:f36871d4e5ee857c6b85532e942550d2cf90ea4ee943d75eb681044bbc4f54f7"},
@@ -2126,7 +2124,7 @@ description = "Extensions to the standard Python datetime module"
 optional = true
 python-versions = "!=3.0.*,!=3.1.*,!=3.2.*,>=2.7"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"saml2\""
+markers = "extra == \"saml2\" or extra == \"all\""
 files = [
    {file = "python-dateutil-2.8.2.tar.gz", hash = "sha256:0123cacc1627ae19ddf3c27a5de5bd67ee4586fbdd6440d9748f8abb483d3e86"},
    {file = "python_dateutil-2.8.2-py2.py3-none-any.whl", hash = "sha256:961d03dc3453ebbc59dbdea9e4e11c5651520a876d0f4db161e8674aae935da9"},
@@ -2154,7 +2152,7 @@ description = "World timezone definitions, modern and historical"
 optional = true
 python-versions = "*"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"saml2\""
+markers = "extra == \"saml2\" or extra == \"all\""
 files = [
    {file = "pytz-2022.7.1-py2.py3-none-any.whl", hash = "sha256:78f4f37d8198e0627c5f1143240bb0206b8691d8d7ac6d78fee88b78733f8c4a"},
    {file = "pytz-2022.7.1.tar.gz", hash = "sha256:01a0681c4b9684a28304615eba55d1ab31ae00bf68ec157ec3708a8182dbbcd0"},
@@ -2553,15 +2551,15 @@ doc = ["Sphinx", "sphinx-rtd-theme"]

 [[package]]
 name = "sentry-sdk"
-version = "2.34.1"
+version = "2.43.0"
 description = "Python client for Sentry (https://sentry.io)"
 optional = true
 python-versions = ">=3.6"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"sentry\""
+markers = "extra == \"sentry\" or extra == \"all\""
 files = [
-    {file = "sentry_sdk-2.34.1-py2.py3-none-any.whl", hash = "sha256:b7a072e1cdc5abc48101d5146e1ae680fa81fe886d8d95aaa25a0b450c818d32"},
-    {file = "sentry_sdk-2.34.1.tar.gz", hash = "sha256:69274eb8c5c38562a544c3e9f68b5be0a43be4b697f5fd385bf98e4fbe672687"},
+    {file = "sentry_sdk-2.43.0-py2.py3-none-any.whl", hash = "sha256:4aacafcf1756ef066d359ae35030881917160ba7f6fc3ae11e0e58b09edc2d5d"},
+    {file = "sentry_sdk-2.43.0.tar.gz", hash = "sha256:52ed6e251c5d2c084224d73efee56b007ef5c2d408a4a071270e82131d336e20"},
 ]

 [package.dependencies]
@@ -2583,20 +2581,25 @@ django = ["django (>=1.8)"]
 falcon = ["falcon (>=1.4)"]
 fastapi = ["fastapi (>=0.79.0)"]
 flask = ["blinker (>=1.1)", "flask (>=0.11)", "markupsafe"]
+google-genai = ["google-genai (>=1.29.0)"]
 grpcio = ["grpcio (>=1.21.1)", "protobuf (>=3.8.0)"]
 http2 = ["httpcore[http2] (==1.*)"]
 httpx = ["httpx (>=0.16.0)"]
 huey = ["huey (>=2)"]
 huggingface-hub = ["huggingface_hub (>=0.22)"]
 langchain = ["langchain (>=0.0.210)"]
+langgraph = ["langgraph (>=0.6.6)"]
 launchdarkly = ["launchdarkly-server-sdk (>=9.8.0)"]
+litellm = ["litellm (>=1.77.5)"]
 litestar = ["litestar (>=2.0.0)"]
 loguru = ["loguru (>=0.5)"]
+mcp = ["mcp (>=1.15.0)"]
 openai = ["openai (>=1.0.0)", "tiktoken (>=0.3.0)"]
 openfeature = ["openfeature-sdk (>=0.7.1)"]
 opentelemetry = ["opentelemetry-distro (>=0.35b0)"]
 opentelemetry-experimental = ["opentelemetry-distro"]
 pure-eval = ["asttokens", "executing", "pure_eval"]
+pydantic-ai = ["pydantic-ai (>=1.0.0)"]
 pymongo = ["pymongo (>=3.1)"]
 pyspark = ["pyspark (>=2.4.4)"]
 quart = ["blinker (>=1.1)", "quart (>=0.16.1)"]
@@ -2746,7 +2749,7 @@ description = "Tornado IOLoop Backed Concurrent Futures"
 optional = true
 python-versions = "*"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"opentracing\""
+markers = "extra == \"opentracing\" or extra == \"all\""
 files = [
    {file = "threadloop-1.0.2-py2-none-any.whl", hash = "sha256:5c90dbefab6ffbdba26afb4829d2a9df8275d13ac7dc58dccb0e279992679599"},
    {file = "threadloop-1.0.2.tar.gz", hash = "sha256:8b180aac31013de13c2ad5c834819771992d350267bddb854613ae77ef571944"},
@@ -2762,7 +2765,7 @@ description = "Python bindings for the Apache Thrift RPC system"
 optional = true
 python-versions = "*"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"opentracing\""
+markers = "extra == \"opentracing\" or extra == \"all\""
 files = [
    {file = "thrift-0.16.0.tar.gz", hash = "sha256:2b5b6488fcded21f9d312aa23c9ff6a0195d0f6ae26ddbd5ad9e3e25dfc14408"},
 ]
@@ -2825,7 +2828,7 @@ description = "Tornado is a Python web framework and asynchronous networking lib
 optional = true
 python-versions = ">=3.9"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"opentracing\""
+markers = "extra == \"opentracing\" or extra == \"all\""
 files = [
    {file = "tornado-6.5-cp39-abi3-macosx_10_9_universal2.whl", hash = "sha256:f81067dad2e4443b015368b24e802d0083fecada4f0a4572fdb72fc06e54a9a6"},
    {file = "tornado-6.5-cp39-abi3-macosx_10_9_x86_64.whl", hash = "sha256:9ac1cbe1db860b3cbb251e795c701c41d343f06a96049d6274e7c77559117e41"},
@@ -2959,7 +2962,7 @@ description = "non-blocking redis client for python"
 optional = true
 python-versions = "*"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"redis\""
+markers = "extra == \"redis\" or extra == \"all\""
 files = [
    {file = "txredisapi-1.4.11-py3-none-any.whl", hash = "sha256:ac64d7a9342b58edca13ef267d4fa7637c1aa63f8595e066801c1e8b56b22d0b"},
    {file = "txredisapi-1.4.11.tar.gz", hash = "sha256:3eb1af99aefdefb59eb877b1dd08861efad60915e30ad5bf3d5bf6c5cedcdbc6"},
@@ -3028,14 +3031,14 @@ referencing = "*"

 [[package]]
 name = "types-netaddr"
-version = "1.3.0.20240530"
+version = "1.3.0.20251108"
 description = "Typing stubs for netaddr"
 optional = false
-python-versions = ">=3.8"
+python-versions = ">=3.9"
 groups = ["dev"]
 files = [
-    {file = "types-netaddr-1.3.0.20240530.tar.gz", hash = "sha256:742c2ec1f202b666f544223e2616b34f1f13df80c91e5aeaaa93a72e4d0774ea"},
-    {file = "types_netaddr-1.3.0.20240530-py3-none-any.whl", hash = "sha256:354998d018e326da4f1d9b005fc91137b7c2c473aaf03c4ef64bf83c6861b440"},
+    {file = "types_netaddr-1.3.0.20251108-py3-none-any.whl", hash = "sha256:1699b3aae860b8754e8ba7fb426905287065c9dbce05d019c25b630ae2ba66c5"},
+    {file = "types_netaddr-1.3.0.20251108.tar.gz", hash = "sha256:2895d8a48eb71ba0ebecf74c6cebaddfa0f97199835ebb406b5aae1725e06ac1"},
 ]

 [[package]]
@@ -3205,7 +3208,7 @@ description = "An XML Schema validator and decoder"
 optional = true
 python-versions = ">=3.7"
 groups = ["main"]
-markers = "extra == \"all\" or extra == \"saml2\""
+markers = "extra == \"saml2\" or extra == \"all\""
 files = [
    {file = "xmlschema-2.4.0-py3-none-any.whl", hash = "sha256:dc87be0caaa61f42649899189aab2fd8e0d567f2cf548433ba7b79278d231a4a"},
    {file = "xmlschema-2.4.0.tar.gz", hash = "sha256:d74cd0c10866ac609e1ef94a5a69b018ad16e39077bc6393408b40c6babee793"},
@@ -3226,7 +3229,7 @@ description = "Backport of pathlib-compatible object wrapper for zip files"
 optional = false
 python-versions = ">=3.8"
 groups = ["dev"]
-markers = "platform_machine != \"ppc64le\" and platform_machine != \"s390x\" and python_version < \"3.12\""
+markers = "python_version < \"3.12\" and platform_machine != \"ppc64le\" and platform_machine != \"s390x\""
 files = [
    {file = "zipp-3.19.1-py3-none-any.whl", hash = "sha256:2828e64edb5386ea6a52e7ba7cdb17bb30a73a858f5eb6eb93d8d36f5ea26091"},
    {file = "zipp-3.19.1.tar.gz", hash = "sha256:35427f6d5594f4acf82d25541438348c26736fa9b3afa2754bcd63cdb99d8e8f"},
@@ -3323,8 +3326,8 @@ docs = ["Sphinx", "repoze.sphinx.autointerface"]
 test = ["zope.i18nmessageid", "zope.testing", "zope.testrunner"]

 [extras]
-all = ["Pympler", "authlib", "hiredis", "jaeger-client", "lxml", "matrix-synapse-ldap3", "opentracing", "psycopg2", "psycopg2cffi", "psycopg2cffi-compat", "pysaml2", "sentry-sdk", "txredisapi"]
-cache-memory = ["Pympler"]
+all = ["authlib", "hiredis", "jaeger-client", "lxml", "matrix-synapse-ldap3", "opentracing", "psycopg2", "psycopg2cffi", "psycopg2cffi-compat", "pympler", "pysaml2", "sentry-sdk", "txredisapi"]
+cache-memory = ["pympler"]
 jwt = ["authlib"]
 matrix-synapse-ldap3 = ["matrix-synapse-ldap3"]
 oidc = ["authlib"]
@@ -3339,5 +3342,5 @@ url-preview = ["lxml"]

 [metadata]
 lock-version = "2.1"
-python-versions = "^3.10.0"
-content-hash = "2a891bc466355554d5c5873e7f8592e4f693de4d0f734ddb55f8a55bb4e529df"
+python-versions = ">=3.10.0,<4.0.0"
+content-hash = "fd472001e409dd3a2a9f0af980a5630fa9edb98fc4b73caa68802a3fd0df5d5f"
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -1,3 +1,183 @@
+[project]
+name = "matrix-synapse"
+version = "1.142.0"
+description = "Homeserver for the Matrix decentralised comms protocol"
+readme = "README.rst"
+authors = [
+    { name = "Matrix.org Team and Contributors", email = "packages@matrix.org" }
+]
+requires-python = ">=3.10.0,<4.0.0"
+license = "AGPL-3.0-or-later OR LicenseRef-Element-Commercial"
+classifiers = [
+    "Development Status :: 5 - Production/Stable",
+    "Topic :: Communications :: Chat",
+]
+
+# Mandatory Dependencies
+dependencies = [
+    # we use the TYPE_CHECKER.redefine method added in jsonschema 3.0.0
+    "jsonschema>=3.0.0",
+    # 0.25.0 is the first version to support Python 3.14.
+    # We can remove this once https://github.com/python-jsonschema/jsonschema/issues/1426 is fixed
+    # and included in a release.
+    "rpds-py>=0.25.0",
+    # We choose 2.0 as a lower bound: the most recent backwards incompatible release.
+    # It seems generally available, judging by https://pkgs.org/search/?q=immutabledict
+    "immutabledict>=2.0",
+    # We require 2.1.0 or higher for type hints. Previous guard was >= 1.1.0
+    "unpaddedbase64>=2.1.0",
+    # We require 2.0.0 for immutabledict support.
+    "canonicaljson>=2.0.0,<3.0.0",
+    # we use the type definitions added in signedjson 1.1.
+    "signedjson>=1.1.0,<2.0.0",
+    # validating SSL certs for IP addresses requires service_identity 18.1.
+    "service-identity>=18.1.0",
+    # Twisted 18.9 introduces some logger improvements that the structured
+    # logger utilises
+    # Twisted 19.7.0 moves test helpers to a new module and deprecates the old location.
+    # Twisted 21.2.0 introduces contextvar support.
+    # We could likely bump this to 22.1 without making distro packagers'
+    # lives hard (as of 2025-07, distro support is Ubuntu LTS: 22.1, Debian stable: 22.4,
+    # RHEL 9: 22.10)
+    "Twisted[tls]>=21.2.0",
+    "treq>=21.5.0",
+    # Twisted has required pyopenssl 16.0 since about Twisted 16.6.
+    "pyOpenSSL>=16.0.0",
+    "PyYAML>=5.3",
+    "pyasn1>=0.1.9",
+    "pyasn1-modules>=0.0.7",
+    "bcrypt>=3.1.7",
+    # 10.0.1 minimum is mandatory here because of libwebp CVE-2023-4863.
+    # Packagers that already took care of libwebp can lower that down to 5.4.0.
+    "Pillow>=10.0.1",
+    # We use SortedDict.peekitem(), which was added in sortedcontainers 1.5.2.
+    # 2.0.5 updates collections.abc imports to avoid Python 3.10 incompatibility.
+    "sortedcontainers>=2.0.5",
+    "pymacaroons>=0.13.0",
+    "msgpack>=0.5.2",
+    "phonenumbers>=8.2.0",
+    # we use GaugeHistogramMetric, which was added in prom-client 0.4.0.
+    # `prometheus_client.metrics` was added in 0.5.0, so we require that too.
+    # We chose 0.6.0 as that is the current version in Debian Buster (oldstable).
+    "prometheus-client>=0.6.0",
+    # we use `order`, which arrived in attrs 19.2.0.
+    # Note: 21.1.0 broke `/sync`, see https://github.com/matrix-org/synapse/issues/9936
+    "attrs>=19.2.0,!=21.1.0",
+    "netaddr>=0.7.18",
+    # Jinja 2.x is incompatible with MarkupSafe>=2.1. To ensure that admins do not
+    # end up with a broken installation, with recent MarkupSafe but old Jinja, we
+    # add a lower bound to the Jinja2 dependency.
+    "Jinja2>=3.0",
+    # 3.2.0 updates collections.abc imports to avoid Python 3.10 incompatibility.
+    "bleach>=3.2.0",
+    # pydantic 2.12 depends on typing-extensions>=4.14.1
+    "typing-extensions>=4.14.1",
+    # We enforce that we have a `cryptography` version that bundles an `openssl`
+    # with the latest security patches.
+    "cryptography>=3.4.7",
+    # ijson 3.1.4 fixes a bug with "." in property names
+    "ijson>=3.1.4",
+    "matrix-common>=1.3.0,<2.0.0",
+    # We need packaging.verison.Version(...).major added in 20.0.
+    "packaging>=20.0",
+    "pydantic>=2.8;python_version < '3.14'",
+    "pydantic>=2.12;python_version >= '3.14'",
+
+    # This is for building the rust components during "poetry install", which
+    # currently ignores the `build-system.requires` directive (c.f.
+    # https://github.com/python-poetry/poetry/issues/6154). Both `pip install` and
+    # `poetry build` do the right thing without this explicit dependency.
+    #
+    # This isn't really a dev-dependency, as `poetry install --without dev` will fail,
+    # but the alternative is to add it to the main list of deps where it isn't
+    # needed.
+    "setuptools_rust>=1.3",
+
+    # This is used for parsing multipart responses
+    "python-multipart>=0.0.9",
+]
+
+[project.optional-dependencies]
+matrix-synapse-ldap3 = ["matrix-synapse-ldap3>=0.1"]
+postgres = [
+    "psycopg2>=2.8;platform_python_implementation != 'PyPy'",
+    "psycopg2cffi>=2.8;platform_python_implementation == 'PyPy'",
+    "psycopg2cffi-compat==1.1;platform_python_implementation == 'PyPy'",
+]
+saml2 = ["pysaml2>=4.5.0"]
+oidc = ["authlib>=0.15.1"]
+# systemd-python is necessary for logging to the systemd journal via
+# `systemd.journal.JournalHandler`, as is documented in
+# `contrib/systemd/log_config.yaml`.
+systemd = ["systemd-python>=231"]
+url-preview = ["lxml>=4.6.3"]
+sentry = ["sentry-sdk>=0.7.2"]
+opentracing = ["jaeger-client>=4.2.0", "opentracing>=2.2.0"]
+jwt = ["authlib"]
+# hiredis is not a *strict* dependency, but it makes things much faster.
+# (if it is not installed, we fall back to slow code.)
+redis = ["txredisapi>=1.4.7", "hiredis"]
+# Required to use experimental `caches.track_memory_usage` config option.
+cache-memory = ["pympler"]
+# If this is updated, don't forget to update the equivalent lines in
+# tool.poetry.group.dev.dependencies.
+test = ["parameterized>=0.9.0", "idna>=3.3"]
+
+# The duplication here is awful.
+#
+# TODO: This can be resolved via PEP 735 dependency groups, which poetry supports
+# since 2.2.0. However, switching to that would require updating the command
+# developers use to install the `all` group. This would require some coordination.
+#
+# NB: the strings in this list must be *package* names, not extra names.
+# Some of our extra names _are_ package names, which can lead to great confusion.
+all = [
+    # matrix-synapse-ldap3
+    "matrix-synapse-ldap3>=0.1",
+    # postgres
+    "psycopg2>=2.8;platform_python_implementation != 'PyPy'",
+    "psycopg2cffi>=2.8;platform_python_implementation == 'PyPy'",
+    "psycopg2cffi-compat==1.1;platform_python_implementation == 'PyPy'",
+    # saml2
+    "pysaml2>=4.5.0",
+    # oidc and jwt
+    "authlib>=0.15.1",
+    # url-preview
+    "lxml>=4.6.3",
+    # sentry
+    "sentry-sdk>=0.7.2",
+    # opentracing
+    "jaeger-client>=4.2.0", "opentracing>=2.2.0",
+    # redis
+    "txredisapi>=1.4.7", "hiredis",
+    # cache-memory
+    "pympler",
+    # omitted:
+    #   - test: it's useful to have this separate from dev deps in the olddeps job
+    #   - systemd: this is a system-based requirement
+]
+
+[project.urls]
+repository = "https://github.com/element-hq/synapse"
+documentation = "https://element-hq.github.io/synapse/latest"
+"Issue Tracker" = "https://github.com/element-hq/synapse/issues"
+
+[project.scripts]
+synapse_homeserver = "synapse.app.homeserver:main"
+synapse_worker = "synapse.app.generic_worker:main"
+synctl = "synapse._scripts.synctl:main"
+
+export_signing_key = "synapse._scripts.export_signing_key:main"
+generate_config = "synapse._scripts.generate_config:main"
+generate_log_config = "synapse._scripts.generate_log_config:main"
+generate_signing_key = "synapse._scripts.generate_signing_key:main"
+hash_password = "synapse._scripts.hash_password:main"
+register_new_matrix_user = "synapse._scripts.register_new_matrix_user:main"
+synapse_port_db = "synapse._scripts.synapse_port_db:main"
+synapse_review_recent_signups = "synapse._scripts.review_recent_signups:main"
+update_synapse_database = "synapse._scripts.update_synapse_database:main"
+
+
 [tool.towncrier]
    package = "synapse"
    filename = "CHANGES.md"
@@ -80,10 +260,15 @@ select = [
    "G",
    # pyupgrade
    "UP006",
+    "UP007",
+    "UP045",
 ]
 extend-safe-fixes = [
-    # pyupgrade
-    "UP006"
+    # pyupgrade rules compatible with Python >= 3.9
+    "UP006",
+    "UP007",
+    # pyupgrade rules compatible with Python >= 3.10
+    "UP045",
 ]

 [tool.ruff.lint.isort]
@@ -106,20 +291,9 @@ manifest-path = "rust/Cargo.toml"
 module-name = "synapse.synapse_rust"

 [tool.poetry]
-name = "matrix-synapse"
-version = "1.142.1"
-description = "Homeserver for the Matrix decentralised comms protocol"
-authors = ["Matrix.org Team and Contributors <packages@matrix.org>"]
-license = "AGPL-3.0-or-later OR LicenseRef-Element-Commercial"
-readme = "README.rst"
-repository = "https://github.com/element-hq/synapse"
 packages = [
    { include = "synapse" },
 ]
-classifiers = [
-    "Development Status :: 5 - Production/Stable",
-    "Topic :: Communications :: Chat",
-]
 include = [
    { path = "AUTHORS.rst", format = "sdist" },
    { path = "book.toml", format = "sdist" },
@@ -149,191 +323,6 @@ exclude = [
 script = "build_rust.py"
 generate-setup-file = true

-[tool.poetry.scripts]
-synapse_homeserver = "synapse.app.homeserver:main"
-synapse_worker = "synapse.app.generic_worker:main"
-synctl = "synapse._scripts.synctl:main"
-
-export_signing_key = "synapse._scripts.export_signing_key:main"
-generate_config = "synapse._scripts.generate_config:main"
-generate_log_config = "synapse._scripts.generate_log_config:main"
-generate_signing_key = "synapse._scripts.generate_signing_key:main"
-hash_password = "synapse._scripts.hash_password:main"
-register_new_matrix_user = "synapse._scripts.register_new_matrix_user:main"
-synapse_port_db = "synapse._scripts.synapse_port_db:main"
-synapse_review_recent_signups = "synapse._scripts.review_recent_signups:main"
-update_synapse_database = "synapse._scripts.update_synapse_database:main"
-
-[tool.poetry.dependencies]
-python = "^3.10.0"
-
-# Mandatory Dependencies
-# ----------------------
-# we use the TYPE_CHECKER.redefine method added in jsonschema 3.0.0
-jsonschema = ">=3.0.0"
-# 0.25.0 is the first version to support Python 3.14.
-# We can remove this once https://github.com/python-jsonschema/jsonschema/issues/1426 is fixed
-# and included in a release.
-rpds-py = ">=0.25.0"
-# We choose 2.0 as a lower bound: the most recent backwards incompatible release.
-# It seems generally available, judging by https://pkgs.org/search/?q=immutabledict
-immutabledict = ">=2.0"
-# We require 2.1.0 or higher for type hints. Previous guard was >= 1.1.0
-unpaddedbase64 = ">=2.1.0"
-# We require 2.0.0 for immutabledict support.
-canonicaljson = "^2.0.0"
-# we use the type definitions added in signedjson 1.1.
-signedjson = "^1.1.0"
-# validating SSL certs for IP addresses requires service_identity 18.1.
-service-identity = ">=18.1.0"
-# Twisted 18.9 introduces some logger improvements that the structured
-# logger utilises
-# Twisted 19.7.0 moves test helpers to a new module and deprecates the old location.
-# Twisted 21.2.0 introduces contextvar support.
-# We could likely bump this to 22.1 without making distro packagers'
-# lives hard (as of 2025-07, distro support is Ubuntu LTS: 22.1, Debian stable: 22.4,
-# RHEL 9: 22.10)
-Twisted = {extras = ["tls"], version = ">=21.2.0"}
-treq = ">=21.5.0"
-# Twisted has required pyopenssl 16.0 since about Twisted 16.6.
-pyOpenSSL = ">=16.0.0"
-PyYAML = ">=5.3"
-pyasn1 = ">=0.1.9"
-pyasn1-modules = ">=0.0.7"
-bcrypt = ">=3.1.7"
-# 10.0.1 minimum is mandatory here because of libwebp CVE-2023-4863.
-# Packagers that already took care of libwebp can lower that down to 5.4.0.
-Pillow = ">=10.0.1"
-# We use SortedDict.peekitem(), which was added in sortedcontainers 1.5.2.
-# 2.0.5 updates collections.abc imports to avoid Python 3.10 incompatibility.
-sortedcontainers = ">=2.0.5"
-pymacaroons = ">=0.13.0"
-msgpack = ">=0.5.2"
-phonenumbers = ">=8.2.0"
-# we use GaugeHistogramMetric, which was added in prom-client 0.4.0.
-# `prometheus_client.metrics` was added in 0.5.0, so we require that too.
-# We chose 0.6.0 as that is the current version in Debian Buster (oldstable).
-prometheus-client = ">=0.6.0"
-# we use `order`, which arrived in attrs 19.2.0.
-# Note: 21.1.0 broke `/sync`, see https://github.com/matrix-org/synapse/issues/9936
-attrs = ">=19.2.0,!=21.1.0"
-netaddr = ">=0.7.18"
-# Jinja 2.x is incompatible with MarkupSafe>=2.1. To ensure that admins do not
-# end up with a broken installation, with recent MarkupSafe but old Jinja, we
-# add a lower bound to the Jinja2 dependency.
-Jinja2 = ">=3.0"
-# 3.2.0 updates collections.abc imports to avoid Python 3.10 incompatibility.
-bleach = ">=3.2.0"
-# pydantic 2.12 depends on typing-extensions>=4.14.1
-typing-extensions = ">=4.14.1"
-# We enforce that we have a `cryptography` version that bundles an `openssl`
-# with the latest security patches.
-cryptography = ">=3.4.7"
-# ijson 3.1.4 fixes a bug with "." in property names
-ijson = ">=3.1.4"
-matrix-common = "^1.3.0"
-# We need packaging.verison.Version(...).major added in 20.0.
-packaging = ">=20.0"
-pydantic = [
-    { version = "~=2.8", python = "<3.14" },
-    { version = "~=2.12", python = ">=3.14" },
-]
-
-# This is for building the rust components during "poetry install", which
-# currently ignores the `build-system.requires` directive (c.f.
-# https://github.com/python-poetry/poetry/issues/6154). Both `pip install` and
-# `poetry build` do the right thing without this explicit dependency.
-#
-# This isn't really a dev-dependency, as `poetry install --without dev` will fail,
-# but the alternative is to add it to the main list of deps where it isn't
-# needed.
-setuptools_rust = ">=1.3"
-
-# This is used for parsing multipart responses
-python-multipart = ">=0.0.9"
-
-# Optional Dependencies
-# ---------------------
-matrix-synapse-ldap3 = { version = ">=0.1", optional = true }
-psycopg2 = { version = ">=2.8", markers = "platform_python_implementation != 'PyPy'", optional = true }
-psycopg2cffi = { version = ">=2.8", markers = "platform_python_implementation == 'PyPy'", optional = true }
-psycopg2cffi-compat = { version = "==1.1", markers = "platform_python_implementation == 'PyPy'", optional = true }
-pysaml2 = { version = ">=4.5.0", optional = true }
-authlib = { version = ">=0.15.1", optional = true }
-# systemd-python is necessary for logging to the systemd journal via
-# `systemd.journal.JournalHandler`, as is documented in
-# `contrib/systemd/log_config.yaml`.
-# Note: systemd-python 231 appears to have been yanked from pypi
-systemd-python = { version = ">=231", optional = true }
-# 4.6.3 removes usage of _PyGen_Send which is unavailable in CPython as of Python 3.10.
-lxml = { version = ">=4.6.3", optional = true }
-sentry-sdk = { version = ">=0.7.2", optional = true }
-opentracing = { version = ">=2.2.0", optional = true }
-# 4.2.0 updates collections.abc imports to avoid Python 3.10 incompatibility.
-jaeger-client = { version = ">=4.2.0", optional = true }
-txredisapi = { version = ">=1.4.7", optional = true }
-hiredis = { version = "*", optional = true }
-Pympler = { version = "*", optional = true }
-parameterized = { version = ">=0.7.4", optional = true }
-idna = { version = ">=2.5", optional = true }
-
-[tool.poetry.extras]
-# NB: Packages that should be part of `pip install matrix-synapse[all]` need to be specified
-# twice: once here, and once in the `all` extra.
-matrix-synapse-ldap3 = ["matrix-synapse-ldap3"]
-postgres = ["psycopg2", "psycopg2cffi", "psycopg2cffi-compat"]
-saml2 = ["pysaml2"]
-oidc = ["authlib"]
-# systemd-python is necessary for logging to the systemd journal via
-# `systemd.journal.JournalHandler`, as is documented in
-# `contrib/systemd/log_config.yaml`.
-systemd = ["systemd-python"]
-url-preview = ["lxml"]
-sentry = ["sentry-sdk"]
-opentracing = ["jaeger-client", "opentracing"]
-jwt = ["authlib"]
-# hiredis is not a *strict* dependency, but it makes things much faster.
-# (if it is not installed, we fall back to slow code.)
-redis = ["txredisapi", "hiredis"]
-# Required to use experimental `caches.track_memory_usage` config option.
-cache-memory = ["pympler"]
-test = ["parameterized", "idna"]
-
-# The duplication here is awful. I hate hate hate hate hate it. However, for now I want
-# to ensure you can still `pip install matrix-synapse[all]` like today. Two motivations:
-# 1) for new installations, I want instructions in existing documentation and tutorials
-#    out there to still work.
-# 2) I don't want to hard-code a list of extras into CI if I can help it. The ideal
-#    solution here would be something like https://github.com/python-poetry/poetry/issues/3413
-# Poetry 1.2's dependency groups might make this easier. But I'm not trying that out
-# until there's a stable release of 1.2.
-#
-# NB: the strings in this list must be *package* names, not extra names.
-# Some of our extra names _are_ package names, which can lead to great confusion.
-all = [
-    # matrix-synapse-ldap3
-    "matrix-synapse-ldap3",
-    # postgres
-    "psycopg2", "psycopg2cffi", "psycopg2cffi-compat",
-    # saml2
-    "pysaml2",
-    # oidc and jwt
-    "authlib",
-    # url-preview
-    "lxml",
-    # sentry
-    "sentry-sdk",
-    # opentracing
-    "jaeger-client", "opentracing",
-    # redis
-    "txredisapi", "hiredis",
-    # cache-memory
-    "pympler",
-    # omitted:
-    #   - test: it's useful to have this separate from dev deps in the olddeps job
-    #   - systemd: this is a system-based requirement
-]
-
 [tool.poetry.group.dev.dependencies]
 # We pin development dependencies in poetry.lock so that our tests don't start
 # failing on new releases. Keeping lower bounds loose here means that dependabot
@@ -359,10 +348,11 @@ types-setuptools = ">=57.4.0"
 # Dependencies which are exclusively required by unit test code. This is
 # NOT a list of all modules that are necessary to run the unit tests.
 # Tests assume that all optional dependencies are installed.
-# parameterized<0.7.4 can create classes with names that would normally be invalid
-# identifiers. trial really does not like this when running with multiple workers.
-parameterized = ">=0.7.4"
-idna = ">=2.5"
+#
+# If this is updated, don't forget to update the equivalent lines in
+# project.optional-dependencies.test.
+parameterized = ">=0.9.0"
+idna = ">=3.3"

 # The following are used by the release script
 click = ">=8.1.3"
@@ -386,7 +376,7 @@ tomli = ">=1.2.3"
 # runtime errors caused by build system changes.
 # We are happy to raise these upper bounds upon request,
 # provided we check that it's safe to do so (i.e. that CI passes).
-requires = ["poetry-core>=1.1.0,<=2.1.3", "setuptools_rust>=1.3,<=1.11.1"]
+requires = ["poetry-core>=2.0.0,<=2.1.3", "setuptools_rust>=1.3,<=1.11.1"]
 build-backend = "poetry.core.masonry.api"


--- a/scripts-dev/build_debian_packages.py
+++ b/scripts-dev/build_debian_packages.py
@@ -18,7 +18,7 @@ import sys
 import threading
 from concurrent.futures import ThreadPoolExecutor
 from types import FrameType
-from typing import Collection, Optional, Sequence
+from typing import Collection, Sequence

 # These are expanded inside the dockerfile to be a fully qualified image name.
 # e.g. docker.io/library/debian:bookworm
@@ -49,7 +49,7 @@ class Builder:
    def __init__(
        self,
        redirect_stdout: bool = False,
-        docker_build_args: Optional[Sequence[str]] = None,
+        docker_build_args: Sequence[str] | None = None,
    ):
        self.redirect_stdout = redirect_stdout
        self._docker_build_args = tuple(docker_build_args or ())
@@ -167,7 +167,7 @@ class Builder:
 def run_builds(
    builder: Builder, dists: Collection[str], jobs: int = 1, skip_tests: bool = False
 ) -> None:
-    def sig(signum: int, _frame: Optional[FrameType]) -> None:
+    def sig(signum: int, _frame: FrameType | None) -> None:
        print("Caught SIGINT")
        builder.kill_containers()

--- 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, Mapping, Optional, Union
+from typing import Any, Mapping
 from urllib import parse as urlparse

 import requests
@@ -103,12 +103,12 @@ def sign_json(


 def request(
-    method: Optional[str],
+    method: str | None,
    origin_name: str,
    origin_key: signedjson.types.SigningKey,
    destination: str,
    path: str,
-    content: Optional[str],
+    content: str | None,
    verify_tls: bool,
 ) -> requests.Response:
    if method is None:
@@ -301,9 +301,9 @@ class MatrixConnectionAdapter(HTTPAdapter):
    def get_connection_with_tls_context(
        self,
        request: PreparedRequest,
-        verify: Optional[Union[bool, str]],
-        proxies: Optional[Mapping[str, str]] = None,
-        cert: Optional[Union[tuple[str, str], str]] = None,
+        verify: bool | str | None,
+        proxies: Mapping[str, str] | None = None,
+        cert: tuple[str, str] | str | None = None,
    ) -> HTTPConnectionPool:
        # overrides the get_connection_with_tls_context() method in the base class
        parsed = urlparse.urlsplit(request.url)
@@ -368,7 +368,7 @@ class MatrixConnectionAdapter(HTTPAdapter):
            return server_name, 8448, server_name

    @staticmethod
-    def _get_well_known(server_name: str) -> Optional[str]:
+    def _get_well_known(server_name: str) -> str | None:
        if ":" in server_name:
            # explicit port, or ipv6 literal. Either way, no .well-known
            return None
--- a/scripts-dev/gen_config_documentation.py
+++ b/scripts-dev/gen_config_documentation.py
@@ -4,7 +4,7 @@
 import json
 import re
 import sys
-from typing import Any, Optional
+from typing import Any

 import yaml

@@ -259,17 +259,17 @@ def indent(text: str, first_line: bool = True) -> str:
    return text


-def em(s: Optional[str]) -> str:
+def em(s: str | None) -> str:
    """Add emphasis to text."""
    return f"*{s}*" if s else ""


-def a(s: Optional[str], suffix: str = " ") -> str:
+def a(s: str | None, suffix: str = " ") -> str:
    """Appends a space if the given string is not empty."""
    return s + suffix if s else ""


-def p(s: Optional[str], prefix: str = " ") -> str:
+def p(s: str | None, prefix: str = " ") -> str:
    """Prepend a space if the given string is not empty."""
    return prefix + s if s else ""

--- a/scripts-dev/mypy_synapse_plugin.py
+++ b/scripts-dev/mypy_synapse_plugin.py
@@ -24,7 +24,7 @@ can crop up, e.g the cache descriptors.
 """

 import enum
-from typing import Callable, Mapping, Optional, Union
+from typing import Callable, Mapping

 import attr
 import mypy.types
@@ -123,7 +123,7 @@ class ArgLocation:
    """


-prometheus_metric_fullname_to_label_arg_map: Mapping[str, Optional[ArgLocation]] = {
+prometheus_metric_fullname_to_label_arg_map: Mapping[str, ArgLocation | None] = {
    # `Collector` subclasses:
    "prometheus_client.metrics.MetricWrapperBase": ArgLocation("labelnames", 2),
    "prometheus_client.metrics.Counter": ArgLocation("labelnames", 2),
@@ -211,7 +211,7 @@ class SynapsePlugin(Plugin):

    def get_base_class_hook(
        self, fullname: str
-    ) -> Optional[Callable[[ClassDefContext], None]]:
+    ) -> Callable[[ClassDefContext], None] | None:
        def _get_base_class_hook(ctx: ClassDefContext) -> None:
            # Run any `get_base_class_hook` checks from other plugins first.
            #
@@ -232,7 +232,7 @@ class SynapsePlugin(Plugin):

    def get_function_signature_hook(
        self, fullname: str
-    ) -> Optional[Callable[[FunctionSigContext], FunctionLike]]:
+    ) -> Callable[[FunctionSigContext], FunctionLike] | None:
        # Strip off the unique identifier for classes that are dynamically created inside
        # functions. ex. `synapse.metrics.jemalloc.JemallocCollector@185` (this is the line
        # number)
@@ -262,7 +262,7 @@ class SynapsePlugin(Plugin):

    def get_method_signature_hook(
        self, fullname: str
-    ) -> Optional[Callable[[MethodSigContext], CallableType]]:
+    ) -> Callable[[MethodSigContext], CallableType] | None:
        if fullname.startswith(
            (
                "synapse.util.caches.descriptors.CachedFunction.__call__",
@@ -721,7 +721,7 @@ def check_is_cacheable_wrapper(ctx: MethodSigContext) -> CallableType:

 def check_is_cacheable(
    signature: CallableType,
-    ctx: Union[MethodSigContext, FunctionSigContext],
+    ctx: MethodSigContext | FunctionSigContext,
 ) -> None:
    """
    Check if a callable returns a type which can be cached.
@@ -795,7 +795,7 @@ AT_CACHED_MUTABLE_RETURN = ErrorCode(

 def is_cacheable(
    rt: mypy.types.Type, signature: CallableType, verbose: bool
-) -> tuple[bool, Optional[str]]:
+) -> tuple[bool, str | None]:
    """
    Check if a particular type is cachable.

--- a/scripts-dev/release.py
+++ b/scripts-dev/release.py
@@ -32,7 +32,7 @@ import time
 import urllib.request
 from os import path
 from tempfile import TemporaryDirectory
-from typing import Any, Match, Optional, Union
+from typing import Any, Match

 import attr
 import click
@@ -327,11 +327,11 @@ def _prepare() -> None:

@cli.command()
@click.option("--gh-token", envvar=["GH_TOKEN", "GITHUB_TOKEN"])
-def tag(gh_token: Optional[str]) -> None:
+def tag(gh_token: str | None) -> None:
    _tag(gh_token)


-def _tag(gh_token: Optional[str]) -> None:
+def _tag(gh_token: str | None) -> None:
    """Tags the release and generates a draft GitHub release"""

    # Test that the GH Token is valid before continuing.
@@ -471,11 +471,11 @@ def _publish(gh_token: str) -> None:

@cli.command()
@click.option("--gh-token", envvar=["GH_TOKEN", "GITHUB_TOKEN"], required=False)
-def upload(gh_token: Optional[str]) -> None:
+def upload(gh_token: str | None) -> None:
    _upload(gh_token)


-def _upload(gh_token: Optional[str]) -> None:
+def _upload(gh_token: str | None) -> None:
    """Upload release to pypi."""

    # Test that the GH Token is valid before continuing.
@@ -576,11 +576,11 @@ def _merge_into(repo: Repo, source: str, target: str) -> None:

@cli.command()
@click.option("--gh-token", envvar=["GH_TOKEN", "GITHUB_TOKEN"], required=False)
-def wait_for_actions(gh_token: Optional[str]) -> None:
+def wait_for_actions(gh_token: str | None) -> None:
    _wait_for_actions(gh_token)


-def _wait_for_actions(gh_token: Optional[str]) -> None:
+def _wait_for_actions(gh_token: str | None) -> None:
    # Test that the GH Token is valid before continuing.
    check_valid_gh_token(gh_token)

@@ -658,7 +658,7 @@ def _notify(message: str) -> None:
    envvar=["GH_TOKEN", "GITHUB_TOKEN"],
    required=False,
 )
-def merge_back(_gh_token: Optional[str]) -> None:
+def merge_back(_gh_token: str | None) -> None:
    _merge_back()


@@ -715,7 +715,7 @@ def _merge_back() -> None:
    envvar=["GH_TOKEN", "GITHUB_TOKEN"],
    required=False,
 )
-def announce(_gh_token: Optional[str]) -> None:
+def announce(_gh_token: str | None) -> None:
    _announce()


@@ -851,7 +851,7 @@ def get_repo_and_check_clean_checkout(
    return repo


-def check_valid_gh_token(gh_token: Optional[str]) -> None:
+def check_valid_gh_token(gh_token: str | None) -> None:
    """Check that a github token is valid, if supplied"""

    if not gh_token:
@@ -867,7 +867,7 @@ def check_valid_gh_token(gh_token: Optional[str]) -> None:
        raise click.ClickException(f"Github credentials are bad: {e}")


-def find_ref(repo: git.Repo, ref_name: str) -> Optional[git.HEAD]:
+def find_ref(repo: git.Repo, ref_name: str) -> git.HEAD | None:
    """Find the branch/ref, looking first locally then in the remote."""
    if ref_name in repo.references:
        return repo.references[ref_name]
@@ -904,7 +904,7 @@ def get_changes_for_version(wanted_version: version.Version) -> str:

        # These are 0-based.
        start_line: int
-        end_line: Optional[int] = None  # Is none if its the last entry
+        end_line: int | None = None  # Is none if its the last entry

    headings: list[VersionSection] = []
    for i, token in enumerate(tokens):
@@ -991,7 +991,7 @@ def build_dependabot_changelog(repo: Repo, current_version: version.Version) ->
    messages = []
    for commit in reversed(commits):
        if commit.author.name == "dependabot[bot]":
-            message: Union[str, bytes] = commit.message
+            message: str | bytes = commit.message
            if isinstance(message, bytes):
                message = message.decode("utf-8")
            messages.append(message.split("\n", maxsplit=1)[0])
--- a/scripts-dev/schema_versions.py
+++ b/scripts-dev/schema_versions.py
@@ -38,7 +38,7 @@ import io
 import json
 import sys
 from collections import defaultdict
-from typing import Any, Iterator, Optional
+from typing import Any, Iterator

 import git
 from packaging import version
@@ -57,7 +57,7 @@ SCHEMA_VERSION_FILES = (
 OLDEST_SHOWN_VERSION = version.parse("v1.0")


-def get_schema_versions(tag: git.Tag) -> tuple[Optional[int], Optional[int]]:
+def get_schema_versions(tag: git.Tag) -> tuple[int | None, int | None]:
    """Get the schema and schema compat versions for a tag."""
    schema_version = None
    schema_compat_version = None
--- a/stubs/sortedcontainers/sorteddict.pyi
+++ b/stubs/sortedcontainers/sorteddict.pyi
@@ -13,10 +13,8 @@ from typing import (
    Iterator,
    KeysView,
    Mapping,
-    Optional,
    Sequence,
    TypeVar,
-    Union,
    ValuesView,
    overload,
 )
@@ -51,7 +49,7 @@ class SortedDict(dict[_KT, _VT]):
        self, __key: _Key[_KT], __iterable: Iterable[tuple[_KT, _VT]], **kwargs: _VT
    ) -> None: ...
    @property
-    def key(self) -> Optional[_Key[_KT]]: ...
+    def key(self) -> _Key[_KT] | None: ...
    @property
    def iloc(self) -> SortedKeysView[_KT]: ...
    def clear(self) -> None: ...
@@ -79,10 +77,10 @@ class SortedDict(dict[_KT, _VT]):
    @overload
    def pop(self, key: _KT) -> _VT: ...
    @overload
-    def pop(self, key: _KT, default: _T = ...) -> Union[_VT, _T]: ...
+    def pop(self, key: _KT, default: _T = ...) -> _VT | _T: ...
    def popitem(self, index: int = ...) -> tuple[_KT, _VT]: ...
    def peekitem(self, index: int = ...) -> tuple[_KT, _VT]: ...
-    def setdefault(self, key: _KT, default: Optional[_VT] = ...) -> _VT: ...
+    def setdefault(self, key: _KT, default: _VT | None = ...) -> _VT: ...
    # Mypy now reports the first overload as an error, because typeshed widened the type
    # of `__map` to its internal `_typeshed.SupportsKeysAndGetItem` type in
    #   https://github.com/python/typeshed/pull/6653
@@ -106,8 +104,8 @@ class SortedDict(dict[_KT, _VT]):
    def _check(self) -> None: ...
    def islice(
        self,
-        start: Optional[int] = ...,
-        stop: Optional[int] = ...,
+        start: int | None = ...,
+        stop: int | None = ...,
        reverse: bool = ...,
    ) -> Iterator[_KT]: ...
    def bisect_left(self, value: _KT) -> int: ...
@@ -118,7 +116,7 @@ class SortedKeysView(KeysView[_KT_co], Sequence[_KT_co]):
    def __getitem__(self, index: int) -> _KT_co: ...
    @overload
    def __getitem__(self, index: slice) -> list[_KT_co]: ...
-    def __delitem__(self, index: Union[int, slice]) -> None: ...
+    def __delitem__(self, index: int | slice) -> None: ...

 class SortedItemsView(ItemsView[_KT_co, _VT_co], Sequence[tuple[_KT_co, _VT_co]]):
    def __iter__(self) -> Iterator[tuple[_KT_co, _VT_co]]: ...
@@ -126,11 +124,11 @@ class SortedItemsView(ItemsView[_KT_co, _VT_co], Sequence[tuple[_KT_co, _VT_co]]
    def __getitem__(self, index: int) -> tuple[_KT_co, _VT_co]: ...
    @overload
    def __getitem__(self, index: slice) -> list[tuple[_KT_co, _VT_co]]: ...
-    def __delitem__(self, index: Union[int, slice]) -> None: ...
+    def __delitem__(self, index: int | slice) -> None: ...

 class SortedValuesView(ValuesView[_VT_co], Sequence[_VT_co]):
    @overload
    def __getitem__(self, index: int) -> _VT_co: ...
    @overload
    def __getitem__(self, index: slice) -> list[_VT_co]: ...
-    def __delitem__(self, index: Union[int, slice]) -> None: ...
+    def __delitem__(self, index: int | slice) -> None: ...
--- a/stubs/sortedcontainers/sortedlist.pyi
+++ b/stubs/sortedcontainers/sortedlist.pyi
@@ -10,10 +10,8 @@ from typing import (
    Iterable,
    Iterator,
    MutableSequence,
-    Optional,
    Sequence,
    TypeVar,
-    Union,
    overload,
 )

@@ -29,8 +27,8 @@ class SortedList(MutableSequence[_T]):
    DEFAULT_LOAD_FACTOR: int = ...
    def __init__(
        self,
-        iterable: Optional[Iterable[_T]] = ...,
-        key: Optional[_Key[_T]] = ...,
+        iterable: Iterable[_T] | None = ...,
+        key: _Key[_T] | None = ...,
    ): ...
    # NB: currently mypy does not honour return type, see mypy #3307
    @overload
@@ -42,7 +40,7 @@ class SortedList(MutableSequence[_T]):
    @overload
    def __new__(cls, iterable: Iterable[_T], key: _Key[_T]) -> SortedKeyList[_T]: ...
    @property
-    def key(self) -> Optional[Callable[[_T], Any]]: ...
+    def key(self) -> Callable[[_T], Any] | None: ...
    def _reset(self, load: int) -> None: ...
    def clear(self) -> None: ...
    def _clear(self) -> None: ...
@@ -57,7 +55,7 @@ class SortedList(MutableSequence[_T]):
    def _pos(self, idx: int) -> int: ...
    def _build_index(self) -> None: ...
    def __contains__(self, value: Any) -> bool: ...
-    def __delitem__(self, index: Union[int, slice]) -> None: ...
+    def __delitem__(self, index: int | slice) -> None: ...
    @overload
    def __getitem__(self, index: int) -> _T: ...
    @overload
@@ -76,8 +74,8 @@ class SortedList(MutableSequence[_T]):
    def reverse(self) -> None: ...
    def islice(
        self,
-        start: Optional[int] = ...,
-        stop: Optional[int] = ...,
+        start: int | None = ...,
+        stop: int | None = ...,
        reverse: bool = ...,
    ) -> Iterator[_T]: ...
    def _islice(
@@ -90,8 +88,8 @@ class SortedList(MutableSequence[_T]):
    ) -> Iterator[_T]: ...
    def irange(
        self,
-        minimum: Optional[int] = ...,
-        maximum: Optional[int] = ...,
+        minimum: int | None = ...,
+        maximum: int | None = ...,
        inclusive: tuple[bool, bool] = ...,
        reverse: bool = ...,
    ) -> Iterator[_T]: ...
@@ -107,7 +105,7 @@ class SortedList(MutableSequence[_T]):
    def insert(self, index: int, value: _T) -> None: ...
    def pop(self, index: int = ...) -> _T: ...
    def index(
-        self, value: _T, start: Optional[int] = ..., stop: Optional[int] = ...
+        self, value: _T, start: int | None = ..., stop: int | None = ...
    ) -> int: ...
    def __add__(self: _SL, other: Iterable[_T]) -> _SL: ...
    def __radd__(self: _SL, other: Iterable[_T]) -> _SL: ...
@@ -126,10 +124,10 @@ class SortedList(MutableSequence[_T]):

 class SortedKeyList(SortedList[_T]):
    def __init__(
-        self, iterable: Optional[Iterable[_T]] = ..., key: _Key[_T] = ...
+        self, iterable: Iterable[_T] | None = ..., key: _Key[_T] = ...
    ) -> None: ...
    def __new__(
-        cls, iterable: Optional[Iterable[_T]] = ..., key: _Key[_T] = ...
+        cls, iterable: Iterable[_T] | None = ..., key: _Key[_T] = ...
    ) -> SortedKeyList[_T]: ...
    @property
    def key(self) -> Callable[[_T], Any]: ...
@@ -146,15 +144,15 @@ class SortedKeyList(SortedList[_T]):
    def _delete(self, pos: int, idx: int) -> None: ...
    def irange(
        self,
-        minimum: Optional[int] = ...,
-        maximum: Optional[int] = ...,
+        minimum: int | None = ...,
+        maximum: int | None = ...,
        inclusive: tuple[bool, bool] = ...,
        reverse: bool = ...,
    ) -> Iterator[_T]: ...
    def irange_key(
        self,
-        min_key: Optional[Any] = ...,
-        max_key: Optional[Any] = ...,
+        min_key: Any | None = ...,
+        max_key: Any | None = ...,
        inclusive: tuple[bool, bool] = ...,
        reserve: bool = ...,
    ) -> Iterator[_T]: ...
@@ -170,7 +168,7 @@ class SortedKeyList(SortedList[_T]):
    def copy(self: _SKL) -> _SKL: ...
    def __copy__(self: _SKL) -> _SKL: ...
    def index(
-        self, value: _T, start: Optional[int] = ..., stop: Optional[int] = ...
+        self, value: _T, start: int | None = ..., stop: int | None = ...
    ) -> int: ...
    def __add__(self: _SKL, other: Iterable[_T]) -> _SKL: ...
    def __radd__(self: _SKL, other: Iterable[_T]) -> _SKL: ...
--- a/stubs/sortedcontainers/sortedset.pyi
+++ b/stubs/sortedcontainers/sortedset.pyi
@@ -11,10 +11,8 @@ from typing import (
    Iterable,
    Iterator,
    MutableSet,
-    Optional,
    Sequence,
    TypeVar,
-    Union,
    overload,
 )

@@ -28,21 +26,19 @@ _Key = Callable[[_T], Any]
 class SortedSet(MutableSet[_T], Sequence[_T]):
    def __init__(
        self,
-        iterable: Optional[Iterable[_T]] = ...,
-        key: Optional[_Key[_T]] = ...,
+        iterable: Iterable[_T] | None = ...,
+        key: _Key[_T] | None = ...,
    ) -> None: ...
    @classmethod
-    def _fromset(
-        cls, values: set[_T], key: Optional[_Key[_T]] = ...
-    ) -> SortedSet[_T]: ...
+    def _fromset(cls, values: set[_T], key: _Key[_T] | None = ...) -> SortedSet[_T]: ...
    @property
-    def key(self) -> Optional[_Key[_T]]: ...
+    def key(self) -> _Key[_T] | None: ...
    def __contains__(self, value: Any) -> bool: ...
    @overload
    def __getitem__(self, index: int) -> _T: ...
    @overload
    def __getitem__(self, index: slice) -> list[_T]: ...
-    def __delitem__(self, index: Union[int, slice]) -> None: ...
+    def __delitem__(self, index: int | slice) -> None: ...
    def __eq__(self, other: Any) -> bool: ...
    def __ne__(self, other: Any) -> bool: ...
    def __lt__(self, other: Iterable[_T]) -> bool: ...
@@ -62,32 +58,28 @@ class SortedSet(MutableSet[_T], Sequence[_T]):
    def _discard(self, value: _T) -> None: ...
    def pop(self, index: int = ...) -> _T: ...
    def remove(self, value: _T) -> None: ...
-    def difference(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def __sub__(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def difference_update(
-        self, *iterables: Iterable[_S]
-    ) -> SortedSet[Union[_T, _S]]: ...
-    def __isub__(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def intersection(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def __and__(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def __rand__(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def intersection_update(
-        self, *iterables: Iterable[_S]
-    ) -> SortedSet[Union[_T, _S]]: ...
-    def __iand__(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def symmetric_difference(self, other: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def __xor__(self, other: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def __rxor__(self, other: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
+    def difference(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def __sub__(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def difference_update(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def __isub__(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def intersection(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def __and__(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def __rand__(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def intersection_update(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def __iand__(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def symmetric_difference(self, other: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def __xor__(self, other: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def __rxor__(self, other: Iterable[_S]) -> SortedSet[_T | _S]: ...
    def symmetric_difference_update(
        self, other: Iterable[_S]
-    ) -> SortedSet[Union[_T, _S]]: ...
-    def __ixor__(self, other: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def union(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def __or__(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def __ror__(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def update(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def __ior__(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
-    def _update(self, *iterables: Iterable[_S]) -> SortedSet[Union[_T, _S]]: ...
+    ) -> SortedSet[_T | _S]: ...
+    def __ixor__(self, other: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def union(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def __or__(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def __ror__(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def update(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def __ior__(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
+    def _update(self, *iterables: Iterable[_S]) -> SortedSet[_T | _S]: ...
    def __reduce__(
        self,
    ) -> tuple[type[SortedSet[_T]], set[_T], Callable[[_T], Any]]: ...
@@ -97,18 +89,18 @@ class SortedSet(MutableSet[_T], Sequence[_T]):
    def bisect_right(self, value: _T) -> int: ...
    def islice(
        self,
-        start: Optional[int] = ...,
-        stop: Optional[int] = ...,
+        start: int | None = ...,
+        stop: int | None = ...,
        reverse: bool = ...,
    ) -> Iterator[_T]: ...
    def irange(
        self,
-        minimum: Optional[_T] = ...,
-        maximum: Optional[_T] = ...,
+        minimum: _T | None = ...,
+        maximum: _T | None = ...,
        inclusive: tuple[bool, bool] = ...,
        reverse: bool = ...,
    ) -> Iterator[_T]: ...
    def index(
-        self, value: _T, start: Optional[int] = ..., stop: Optional[int] = ...
+        self, value: _T, start: int | None = ..., stop: int | None = ...
    ) -> int: ...
    def _reset(self, load: int) -> None: ...
--- a/stubs/txredisapi.pyi
+++ b/stubs/txredisapi.pyi
@@ -15,7 +15,7 @@

 """Contains *incomplete* type hints for txredisapi."""

-from typing import Any, Optional, Union
+from typing import Any

 from twisted.internet import protocol
 from twisted.internet.defer import Deferred
@@ -29,8 +29,8 @@ class RedisProtocol(protocol.Protocol):
        self,
        key: str,
        value: Any,
-        expire: Optional[int] = None,
-        pexpire: Optional[int] = None,
+        expire: int | None = None,
+        pexpire: int | None = None,
        only_if_not_exists: bool = False,
        only_if_exists: bool = False,
    ) -> "Deferred[None]": ...
@@ -38,8 +38,8 @@ class RedisProtocol(protocol.Protocol):

 class SubscriberProtocol(RedisProtocol):
    def __init__(self, *args: object, **kwargs: object): ...
-    password: Optional[str]
-    def subscribe(self, channels: Union[str, list[str]]) -> "Deferred[None]": ...
+    password: str | None
+    def subscribe(self, channels: str | list[str]) -> "Deferred[None]": ...
    def connectionMade(self) -> None: ...
    # type-ignore: twisted.internet.protocol.Protocol provides a default argument for
    # `reason`. txredisapi's LineReceiver Protocol doesn't. But that's fine: it's what's
@@ -49,12 +49,12 @@ class SubscriberProtocol(RedisProtocol):
 def lazyConnection(
    host: str = ...,
    port: int = ...,
-    dbid: Optional[int] = ...,
+    dbid: int | None = ...,
    reconnect: bool = ...,
    charset: str = ...,
-    password: Optional[str] = ...,
-    connectTimeout: Optional[int] = ...,
-    replyTimeout: Optional[int] = ...,
+    password: str | None = ...,
+    connectTimeout: int | None = ...,
+    replyTimeout: int | None = ...,
    convertNumbers: bool = ...,
 ) -> RedisProtocol: ...

@@ -70,18 +70,18 @@ class RedisFactory(protocol.ReconnectingClientFactory):
    continueTrying: bool
    handler: ConnectionHandler
    pool: list[RedisProtocol]
-    replyTimeout: Optional[int]
+    replyTimeout: int | None
    def __init__(
        self,
        uuid: str,
-        dbid: Optional[int],
+        dbid: int | None,
        poolsize: int,
        isLazy: bool = False,
        handler: type = ConnectionHandler,
        charset: str = "utf-8",
-        password: Optional[str] = None,
-        replyTimeout: Optional[int] = None,
-        convertNumbers: Optional[int] = True,
+        password: str | None = None,
+        replyTimeout: int | None = None,
+        convertNumbers: int | None = True,
    ): ...
    def buildProtocol(self, addr: IAddress) -> RedisProtocol: ...

--- a/synapse/_scripts/export_signing_key.py
+++ b/synapse/_scripts/export_signing_key.py
@@ -22,13 +22,13 @@
 import argparse
 import sys
 import time
-from typing import NoReturn, Optional
+from typing import NoReturn

 from signedjson.key import encode_verify_key_base64, get_verify_key, read_signing_keys
 from signedjson.types import VerifyKey


-def exit(status: int = 0, message: Optional[str] = None) -> NoReturn:
+def exit(status: int = 0, message: str | None = None) -> NoReturn:
    if message:
        print(message, file=sys.stderr)
    sys.exit(status)
--- a/synapse/_scripts/generate_workers_map.py
+++ b/synapse/_scripts/generate_workers_map.py
@@ -25,7 +25,7 @@ import logging
 import re
 from collections import defaultdict
 from dataclasses import dataclass
-from typing import Iterable, Optional, Pattern
+from typing import Iterable, Pattern

 import yaml

@@ -46,7 +46,7 @@ logger = logging.getLogger("generate_workers_map")
 class MockHomeserver(HomeServer):
    DATASTORE_CLASS = DataStore

-    def __init__(self, config: HomeServerConfig, worker_app: Optional[str]) -> None:
+    def __init__(self, config: HomeServerConfig, worker_app: str | None) -> None:
        super().__init__(config.server.server_name, config=config)
        self.config.worker.worker_app = worker_app

@@ -65,7 +65,7 @@ class EndpointDescription:

    # The category of this endpoint. Is read from the `CATEGORY` constant in the servlet
    # class.
-    category: Optional[str]
+    category: str | None

    # TODO:
    #  - does it need to be routed based on a stream writer config?
@@ -141,7 +141,7 @@ def get_registered_paths_for_hs(


 def get_registered_paths_for_default(
-    worker_app: Optional[str], base_config: HomeServerConfig
+    worker_app: str | None, base_config: HomeServerConfig
 ) -> dict[tuple[str, str], EndpointDescription]:
    """
    Given the name of a worker application and a base homeserver configuration,
@@ -271,7 +271,7 @@ def main() -> None:
    # TODO SSO endpoints (pick_idp etc) NOT REGISTERED BY THIS SCRIPT

    categories_to_methods_and_paths: dict[
-        Optional[str], dict[tuple[str, str], EndpointDescription]
+        str | None, dict[tuple[str, str], EndpointDescription]
    ] = defaultdict(dict)

    for (method, path), desc in elided_worker_paths.items():
@@ -282,7 +282,7 @@ def main() -> None:


 def print_category(
-    category_name: Optional[str],
+    category_name: str | None,
    elided_worker_paths: dict[tuple[str, str], EndpointDescription],
 ) -> None:
    """
--- a/synapse/_scripts/register_new_matrix_user.py
+++ b/synapse/_scripts/register_new_matrix_user.py
@@ -26,7 +26,7 @@ import hashlib
 import hmac
 import logging
 import sys
-from typing import Any, Callable, Optional
+from typing import Any, Callable, Iterable, TextIO

 import requests
 import yaml
@@ -54,7 +54,7 @@ def request_registration(
    server_location: str,
    shared_secret: str,
    admin: bool = False,
-    user_type: Optional[str] = None,
+    user_type: str | None = None,
    _print: Callable[[str], None] = print,
    exit: Callable[[int], None] = sys.exit,
    exists_ok: bool = False,
@@ -123,13 +123,13 @@ def register_new_user(
    password: str,
    server_location: str,
    shared_secret: str,
-    admin: Optional[bool],
-    user_type: Optional[str],
+    admin: bool | None,
+    user_type: str | None,
    exists_ok: bool = False,
 ) -> None:
    if not user:
        try:
-            default_user: Optional[str] = getpass.getuser()
+            default_user: str | None = getpass.getuser()
        except Exception:
            default_user = None

@@ -244,6 +244,7 @@ def main() -> None:
    group.add_argument(
        "-c",
        "--config",
+        action="append",
        type=argparse.FileType("r"),
        help="Path to server config file. Used to read in shared secret.",
    )
@@ -262,9 +263,9 @@ def main() -> None:

    args = parser.parse_args()

-    config: Optional[dict[str, Any]] = None
+    config: dict[str, Any] | None = None
    if "config" in args and args.config:
-        config = yaml.safe_load(args.config)
+        config = _read_config_files(args.config)

    if args.shared_secret:
        secret = args.shared_secret
@@ -326,6 +327,33 @@ def main() -> None:
    )


+# Adapted from synapse.config._base.
+def _read_config_files(config_files: Iterable[TextIO]) -> dict[str, Any]:
+    """Read the config files and shallowly merge them into a dict.
+
+    Successive configurations are shallowly merged into ones provided earlier,
+    i.e., entirely replacing top-level sections of the configuration.
+
+    Args:
+        config_files: A list of the config files to read
+
+    Returns:
+        The configuration dictionary.
+    """
+    specified_config = {}
+    for config_file in config_files:
+        yaml_config = yaml.safe_load(config_file)
+
+        if not isinstance(yaml_config, dict):
+            err = "File %r is empty or doesn't parse into a key-value map. IGNORING."
+            print(err % (config_file,))
+            continue
+
+        specified_config.update(yaml_config)
+
+    return specified_config
+
+
 def _read_file(file_path: Any, config_path: str) -> str:
    """Check the given file exists, and read it into a string

@@ -350,7 +378,7 @@ def _read_file(file_path: Any, config_path: str) -> str:
        sys.exit(1)


-def _find_client_listener(config: dict[str, Any]) -> Optional[str]:
+def _find_client_listener(config: dict[str, Any]) -> str | None:
    # try to find a listener in the config. Returns a host:port pair
    for listener in config.get("listeners", []):
        if listener.get("type") != "http" or listener.get("tls", False):
--- a/synapse/_scripts/synapse_port_db.py
+++ b/synapse/_scripts/synapse_port_db.py
@@ -107,6 +107,7 @@ logger = logging.getLogger("synapse_port_db")
 BOOLEAN_COLUMNS = {
    "access_tokens": ["used"],
    "account_validity": ["email_sent"],
+    "delayed_events": ["is_processed"],
    "device_lists_changes_in_room": ["converted_to_destinations"],
    "device_lists_outbound_pokes": ["sent"],
    "devices": ["hidden"],
@@ -233,14 +234,14 @@ IGNORED_BACKGROUND_UPDATES = {

 # Error returned by the run function. Used at the top-level part of the script to
 # handle errors and return codes.
-end_error: Optional[str] = None
+end_error: str | None = None
 # The exec_info for the error, if any. If error is defined but not exec_info the script
 # will show only the error message without the stacktrace, if exec_info is defined but
 # not the error then the script will show nothing outside of what's printed in the run
 # function. If both are defined, the script will print both the error and the stacktrace.
-end_error_exec_info: Optional[
-    tuple[type[BaseException], BaseException, TracebackType]
-] = None
+end_error_exec_info: tuple[type[BaseException], BaseException, TracebackType] | None = (
+    None
+)

 R = TypeVar("R")

@@ -485,7 +486,7 @@ class Porter:

            def r(
                txn: LoggingTransaction,
-            ) -> tuple[Optional[list[str]], list[tuple], list[tuple]]:
+            ) -> tuple[list[str] | None, list[tuple], list[tuple]]:
                forward_rows = []
                backward_rows = []
                if do_forward[0]:
@@ -502,7 +503,7 @@ class Porter:

                if forward_rows or backward_rows:
                    assert txn.description is not None
-                    headers: Optional[list[str]] = [
+                    headers: list[str] | None = [
                        column[0] for column in txn.description
                    ]
                else:
@@ -1152,9 +1153,7 @@ class Porter:
        return done, remaining + done

    async def _setup_state_group_id_seq(self) -> None:
-        curr_id: Optional[
-            int
-        ] = await self.sqlite_store.db_pool.simple_select_one_onecol(
+        curr_id: int | None = await self.sqlite_store.db_pool.simple_select_one_onecol(
            table="state_groups", keyvalues={}, retcol="MAX(id)", allow_none=True
        )

@@ -1271,10 +1270,10 @@ class Porter:

        await self.postgres_store.db_pool.runInteraction("_setup_%s" % (seq_name,), r)

-    async def _pg_get_serial_sequence(self, table: str, column: str) -> Optional[str]:
+    async def _pg_get_serial_sequence(self, table: str, column: str) -> str | None:
        """Returns the name of the postgres sequence associated with a column, or NULL."""

-        def r(txn: LoggingTransaction) -> Optional[str]:
+        def r(txn: LoggingTransaction) -> str | None:
            txn.execute("SELECT pg_get_serial_sequence('%s', '%s')" % (table, column))
            result = txn.fetchone()
            if not result:
@@ -1286,9 +1285,9 @@ class Porter:
        )

    async def _setup_auth_chain_sequence(self) -> None:
-        curr_chain_id: Optional[
-            int
-        ] = await self.sqlite_store.db_pool.simple_select_one_onecol(
+        curr_chain_id: (
+            int | None
+        ) = await self.sqlite_store.db_pool.simple_select_one_onecol(
            table="event_auth_chains",
            keyvalues={},
            retcol="MAX(chain_id)",
--- a/synapse/_scripts/synctl.py
+++ b/synapse/_scripts/synctl.py
@@ -30,7 +30,7 @@ import signal
 import subprocess
 import sys
 import time
-from typing import Iterable, NoReturn, Optional, TextIO
+from typing import Iterable, NoReturn, TextIO

 import yaml

@@ -135,7 +135,7 @@ def start(pidfile: str, app: str, config_files: Iterable[str], daemonize: bool)
        return False


-def stop(pidfile: str, app: str) -> Optional[int]:
+def stop(pidfile: str, app: str) -> int | None:
    """Attempts to kill a synapse worker from the pidfile.
    Args:
        pidfile: path to file containing worker's pid
--- a/synapse/api/auth/init.py
+++ b/synapse/api/auth/init.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import TYPE_CHECKING, Optional, Protocol
+from typing import TYPE_CHECKING, Protocol

 from prometheus_client import Histogram

@@ -51,7 +51,7 @@ class Auth(Protocol):
        room_id: str,
        requester: Requester,
        allow_departed_users: bool = False,
-    ) -> tuple[str, Optional[str]]:
+    ) -> tuple[str, str | None]:
        """Check if the user is in the room, or was at some point.
        Args:
            room_id: The room to check.
@@ -190,7 +190,7 @@ class Auth(Protocol):

    async def check_user_in_room_or_world_readable(
        self, room_id: str, requester: Requester, allow_departed_users: bool = False
-    ) -> tuple[str, Optional[str]]:
+    ) -> tuple[str, str | None]:
        """Checks that the user is or was in the room or the room is world
        readable. If it isn't then an exception is raised.

--- a/synapse/api/auth/base.py
+++ b/synapse/api/auth/base.py
@@ -19,7 +19,7 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING

 from netaddr import IPAddress

@@ -64,7 +64,7 @@ class BaseAuth:
        room_id: str,
        requester: Requester,
        allow_departed_users: bool = False,
-    ) -> tuple[str, Optional[str]]:
+    ) -> tuple[str, str | None]:
        """Check if the user is in the room, or was at some point.
        Args:
            room_id: The room to check.
@@ -114,7 +114,7 @@ class BaseAuth:
    @trace
    async def check_user_in_room_or_world_readable(
        self, room_id: str, requester: Requester, allow_departed_users: bool = False
-    ) -> tuple[str, Optional[str]]:
+    ) -> tuple[str, str | None]:
        """Checks that the user is or was in the room or the room is world
        readable. If it isn't then an exception is raised.

@@ -294,7 +294,7 @@ class BaseAuth:
    @cancellable
    async def get_appservice_user(
        self, request: Request, access_token: str
-    ) -> Optional[Requester]:
+    ) -> Requester | None:
        """
        Given a request, reads the request parameters to determine:
        - whether it's an application service that's making this request
--- a/synapse/api/auth/mas.py
+++ b/synapse/api/auth/mas.py
@@ -13,10 +13,11 @@
 #
 #
 import logging
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING
 from urllib.parse import urlencode

 from pydantic import (
+    AnyHttpUrl,
    BaseModel,
    ConfigDict,
    StrictBool,
@@ -73,11 +74,11 @@ class ServerMetadata(BaseModel):
 class IntrospectionResponse(BaseModel):
    retrieved_at_ms: StrictInt
    active: StrictBool
-    scope: Optional[StrictStr] = None
-    username: Optional[StrictStr] = None
-    sub: Optional[StrictStr] = None
-    device_id: Optional[StrictStr] = None
-    expires_in: Optional[StrictInt] = None
+    scope: StrictStr | None = None
+    username: StrictStr | None = None
+    sub: StrictStr | None = None
+    device_id: StrictStr | None = None
+    expires_in: StrictInt | None = None
    model_config = ConfigDict(extra="allow")

    def get_scope_set(self) -> set[str]:
@@ -146,13 +147,33 @@ class MasDelegatedAuth(BaseAuth):

    @property
    def _metadata_url(self) -> str:
-        return (
-            f"{str(self._config.endpoint).rstrip('/')}/.well-known/openid-configuration"
+        return str(
+            AnyHttpUrl.build(
+                scheme=self._config.endpoint.scheme,
+                username=self._config.endpoint.username,
+                password=self._config.endpoint.password,
+                host=self._config.endpoint.host or "",
+                port=self._config.endpoint.port,
+                path=".well-known/openid-configuration",
+                query=None,
+                fragment=None,
+            )
        )

    @property
    def _introspection_endpoint(self) -> str:
-        return f"{str(self._config.endpoint).rstrip('/')}/oauth2/introspect"
+        return str(
+            AnyHttpUrl.build(
+                scheme=self._config.endpoint.scheme,
+                username=self._config.endpoint.username,
+                password=self._config.endpoint.password,
+                host=self._config.endpoint.host or "",
+                port=self._config.endpoint.port,
+                path="oauth2/introspect",
+                query=None,
+                fragment=None,
+            )
+        )

    async def _load_metadata(self) -> ServerMetadata:
        response = await self._http_client.get_json(self._metadata_url)
--- a/synapse/api/auth/msc3861_delegated.py
+++ b/synapse/api/auth/msc3861_delegated.py
@@ -20,7 +20,7 @@
 #
 import logging
 from dataclasses import dataclass
-from typing import TYPE_CHECKING, Any, Callable, Optional
+from typing import TYPE_CHECKING, Any, Callable
 from urllib.parse import urlencode

 from authlib.oauth2 import ClientAuth
@@ -102,25 +102,25 @@ class IntrospectionResult:
            return []
        return scope_to_list(value)

-    def get_sub(self) -> Optional[str]:
+    def get_sub(self) -> str | None:
        value = self._inner.get("sub")
        if not isinstance(value, str):
            return None
        return value

-    def get_username(self) -> Optional[str]:
+    def get_username(self) -> str | None:
        value = self._inner.get("username")
        if not isinstance(value, str):
            return None
        return value

-    def get_name(self) -> Optional[str]:
+    def get_name(self) -> str | None:
        value = self._inner.get("name")
        if not isinstance(value, str):
            return None
        return value

-    def get_device_id(self) -> Optional[str]:
+    def get_device_id(self) -> str | None:
        value = self._inner.get("device_id")
        if value is not None and not isinstance(value, str):
            raise AuthError(
@@ -174,7 +174,7 @@ class MSC3861DelegatedAuth(BaseAuth):
        self._clock = hs.get_clock()
        self._http_client = hs.get_proxied_http_client()
        self._hostname = hs.hostname
-        self._admin_token: Callable[[], Optional[str]] = self._config.admin_token
+        self._admin_token: Callable[[], str | None] = self._config.admin_token
        self._force_tracing_for_users = hs.config.tracing.force_tracing_for_users

        self._rust_http_client = HttpClient(
@@ -247,7 +247,7 @@ class MSC3861DelegatedAuth(BaseAuth):
        metadata = await self._issuer_metadata.get()
        return metadata.issuer or self._config.issuer

-    async def account_management_url(self) -> Optional[str]:
+    async def account_management_url(self) -> str | None:
        """
        Get the configured account management URL

--- a/synapse/api/auth_blocking.py
+++ b/synapse/api/auth_blocking.py
@@ -20,7 +20,7 @@
 #

 import logging
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING

 from synapse.api.constants import LimitBlockingTypes, UserTypes
 from synapse.api.errors import Codes, ResourceLimitError
@@ -51,10 +51,10 @@ class AuthBlocking:

    async def check_auth_blocking(
        self,
-        user_id: Optional[str] = None,
-        threepid: Optional[dict] = None,
-        user_type: Optional[str] = None,
-        requester: Optional[Requester] = None,
+        user_id: str | None = None,
+        threepid: dict | None = None,
+        user_type: str | None = None,
+        requester: Requester | None = None,
    ) -> None:
        """Checks if the user should be rejected for some external reason,
        such as monthly active user limiting or global disable flag
--- a/synapse/api/errors.py
+++ b/synapse/api/errors.py
@@ -26,7 +26,7 @@ import math
 import typing
 from enum import Enum
 from http import HTTPStatus
-from typing import Any, Optional, Union
+from typing import Any, Optional

 from twisted.web import http

@@ -164,9 +164,9 @@ class CodeMessageException(RuntimeError):

    def __init__(
        self,
-        code: Union[int, HTTPStatus],
+        code: int | HTTPStatus,
        msg: str,
-        headers: Optional[dict[str, str]] = None,
+        headers: dict[str, str] | None = None,
    ):
        super().__init__("%d: %s" % (code, msg))

@@ -223,8 +223,8 @@ class SynapseError(CodeMessageException):
        code: int,
        msg: str,
        errcode: str = Codes.UNKNOWN,
-        additional_fields: Optional[dict] = None,
-        headers: Optional[dict[str, str]] = None,
+        additional_fields: dict | None = None,
+        headers: dict[str, str] | None = None,
    ):
        """Constructs a synapse error.

@@ -244,7 +244,7 @@ class SynapseError(CodeMessageException):
        return cs_error(self.msg, self.errcode, **self._additional_fields)

    @property
-    def debug_context(self) -> Optional[str]:
+    def debug_context(self) -> str | None:
        """Override this to add debugging context that shouldn't be sent to clients."""
        return None

@@ -276,7 +276,7 @@ class ProxiedRequestError(SynapseError):
        code: int,
        msg: str,
        errcode: str = Codes.UNKNOWN,
-        additional_fields: Optional[dict] = None,
+        additional_fields: dict | None = None,
    ):
        super().__init__(code, msg, errcode, additional_fields)

@@ -340,7 +340,7 @@ class FederationDeniedError(SynapseError):
        destination: The destination which has been denied
    """

-    def __init__(self, destination: Optional[str]):
+    def __init__(self, destination: str | None):
        """Raised by federation client or server to indicate that we are
        are deliberately not attempting to contact a given server because it is
        not on our federation whitelist.
@@ -399,7 +399,7 @@ class AuthError(SynapseError):
        code: int,
        msg: str,
        errcode: str = Codes.FORBIDDEN,
-        additional_fields: Optional[dict] = None,
+        additional_fields: dict | None = None,
    ):
        super().__init__(code, msg, errcode, additional_fields)

@@ -432,7 +432,7 @@ class UnstableSpecAuthError(AuthError):
        msg: str,
        errcode: str,
        previous_errcode: str = Codes.FORBIDDEN,
-        additional_fields: Optional[dict] = None,
+        additional_fields: dict | None = None,
    ):
        self.previous_errcode = previous_errcode
        super().__init__(code, msg, errcode, additional_fields)
@@ -497,8 +497,8 @@ class ResourceLimitError(SynapseError):
        code: int,
        msg: str,
        errcode: str = Codes.RESOURCE_LIMIT_EXCEEDED,
-        admin_contact: Optional[str] = None,
-        limit_type: Optional[str] = None,
+        admin_contact: str | None = None,
+        limit_type: str | None = None,
    ):
        self.admin_contact = admin_contact
        self.limit_type = limit_type
@@ -542,7 +542,7 @@ class InvalidCaptchaError(SynapseError):
        self,
        code: int = 400,
        msg: str = "Invalid captcha.",
-        error_url: Optional[str] = None,
+        error_url: str | None = None,
        errcode: str = Codes.CAPTCHA_INVALID,
    ):
        super().__init__(code, msg, errcode)
@@ -563,9 +563,9 @@ class LimitExceededError(SynapseError):
        self,
        limiter_name: str,
        code: int = 429,
-        retry_after_ms: Optional[int] = None,
+        retry_after_ms: int | None = None,
        errcode: str = Codes.LIMIT_EXCEEDED,
-        pause: Optional[float] = None,
+        pause: float | None = None,
    ):
        # Use HTTP header Retry-After to enable library-assisted retry handling.
        headers = (
@@ -582,7 +582,7 @@ class LimitExceededError(SynapseError):
        return cs_error(self.msg, self.errcode, retry_after_ms=self.retry_after_ms)

    @property
-    def debug_context(self) -> Optional[str]:
+    def debug_context(self) -> str | None:
        return self.limiter_name


@@ -675,7 +675,7 @@ class RequestSendFailed(RuntimeError):


 class UnredactedContentDeletedError(SynapseError):
-    def __init__(self, content_keep_ms: Optional[int] = None):
+    def __init__(self, content_keep_ms: int | None = None):
        super().__init__(
            404,
            "The content for that event has already been erased from the database",
@@ -751,7 +751,7 @@ class FederationError(RuntimeError):
        code: int,
        reason: str,
        affected: str,
-        source: Optional[str] = None,
+        source: str | None = None,
    ):
        if level not in ["FATAL", "ERROR", "WARN"]:
            raise ValueError("Level is not valid: %s" % (level,))
@@ -786,7 +786,7 @@ class FederationPullAttemptBackoffError(RuntimeError):
    """

    def __init__(
-        self, event_ids: "StrCollection", message: Optional[str], retry_after_ms: int
+        self, event_ids: "StrCollection", message: str | None, retry_after_ms: int
    ):
        event_ids = list(event_ids)

--- a/synapse/api/filtering.py
+++ b/synapse/api/filtering.py
@@ -28,9 +28,7 @@ from typing import (
    Collection,
    Iterable,
    Mapping,
-    Optional,
    TypeVar,
-    Union,
 )

 import jsonschema
@@ -155,7 +153,7 @@ class Filtering:
        self.DEFAULT_FILTER_COLLECTION = FilterCollection(hs, {})

    async def get_user_filter(
-        self, user_id: UserID, filter_id: Union[int, str]
+        self, user_id: UserID, filter_id: int | str
    ) -> "FilterCollection":
        result = await self.store.get_user_filter(user_id, filter_id)
        return FilterCollection(self._hs, result)
@@ -531,7 +529,7 @@ class Filter:
        return newFilter


-def _matches_wildcard(actual_value: Optional[str], filter_value: str) -> bool:
+def _matches_wildcard(actual_value: str | None, filter_value: str) -> bool:
    if filter_value.endswith("*") and isinstance(actual_value, str):
        type_prefix = filter_value[:-1]
        return actual_value.startswith(type_prefix)
--- a/synapse/api/presence.py
+++ b/synapse/api/presence.py
@@ -19,7 +19,7 @@
 #
 #

-from typing import Any, Optional
+from typing import Any

 import attr

@@ -41,15 +41,13 @@ class UserDevicePresenceState:
    """

    user_id: str
-    device_id: Optional[str]
+    device_id: str | None
    state: str
    last_active_ts: int
    last_sync_ts: int

    @classmethod
-    def default(
-        cls, user_id: str, device_id: Optional[str]
-    ) -> "UserDevicePresenceState":
+    def default(cls, user_id: str, device_id: str | None) -> "UserDevicePresenceState":
        """Returns a default presence state."""
        return cls(
            user_id=user_id,
@@ -81,7 +79,7 @@ class UserPresenceState:
    last_active_ts: int
    last_federation_update_ts: int
    last_user_sync_ts: int
-    status_msg: Optional[str]
+    status_msg: str | None
    currently_active: bool

    def as_dict(self) -> JsonDict:
--- a/synapse/api/ratelimiting.py
+++ b/synapse/api/ratelimiting.py
@@ -102,9 +102,7 @@ class Ratelimiter:

        self.clock.looping_call(self._prune_message_counts, 15 * 1000)

-    def _get_key(
-        self, requester: Optional[Requester], key: Optional[Hashable]
-    ) -> Hashable:
+    def _get_key(self, requester: Requester | None, key: Hashable | None) -> Hashable:
        """Use the requester's MXID as a fallback key if no key is provided."""
        if key is None:
            if not requester:
@@ -121,13 +119,13 @@ class Ratelimiter:

    async def can_do_action(
        self,
-        requester: Optional[Requester],
-        key: Optional[Hashable] = None,
-        rate_hz: Optional[float] = None,
-        burst_count: Optional[int] = None,
+        requester: Requester | None,
+        key: Hashable | None = None,
+        rate_hz: float | None = None,
+        burst_count: int | None = None,
        update: bool = True,
        n_actions: int = 1,
-        _time_now_s: Optional[float] = None,
+        _time_now_s: float | None = None,
    ) -> tuple[bool, float]:
        """Can the entity (e.g. user or IP address) perform the action?

@@ -247,10 +245,10 @@ class Ratelimiter:

    def record_action(
        self,
-        requester: Optional[Requester],
-        key: Optional[Hashable] = None,
+        requester: Requester | None,
+        key: Hashable | None = None,
        n_actions: int = 1,
-        _time_now_s: Optional[float] = None,
+        _time_now_s: float | None = None,
    ) -> None:
        """Record that an action(s) took place, even if they violate the rate limit.

@@ -332,14 +330,14 @@ class Ratelimiter:

    async def ratelimit(
        self,
-        requester: Optional[Requester],
-        key: Optional[Hashable] = None,
-        rate_hz: Optional[float] = None,
-        burst_count: Optional[int] = None,
+        requester: Requester | None,
+        key: Hashable | None = None,
+        rate_hz: float | None = None,
+        burst_count: int | None = None,
        update: bool = True,
        n_actions: int = 1,
-        _time_now_s: Optional[float] = None,
-        pause: Optional[float] = 0.5,
+        _time_now_s: float | None = None,
+        pause: float | None = 0.5,
    ) -> None:
        """Checks if an action can be performed. If not, raises a LimitExceededError

@@ -396,7 +394,7 @@ class RequestRatelimiter:
        store: DataStore,
        clock: Clock,
        rc_message: RatelimitSettings,
-        rc_admin_redaction: Optional[RatelimitSettings],
+        rc_admin_redaction: RatelimitSettings | None,
    ):
        self.store = store
        self.clock = clock
@@ -412,7 +410,7 @@ class RequestRatelimiter:
        # Check whether ratelimiting room admin message redaction is enabled
        # by the presence of rate limits in the config
        if rc_admin_redaction:
-            self.admin_redaction_ratelimiter: Optional[Ratelimiter] = Ratelimiter(
+            self.admin_redaction_ratelimiter: Ratelimiter | None = Ratelimiter(
                store=self.store,
                clock=self.clock,
                cfg=rc_admin_redaction,
--- a/synapse/api/room_versions.py
+++ b/synapse/api/room_versions.py
@@ -18,7 +18,7 @@
 #
 #

-from typing import Callable, Optional
+from typing import Callable

 import attr

@@ -503,7 +503,7 @@ class RoomVersionCapability:
    """An object which describes the unique attributes of a room version."""

    identifier: str  # the identifier for this capability
-    preferred_version: Optional[RoomVersion]
+    preferred_version: RoomVersion | None
    support_check_lambda: Callable[[RoomVersion], bool]


--- a/synapse/api/urls.py
+++ b/synapse/api/urls.py
@@ -24,7 +24,6 @@
 import hmac
 import urllib.parse
 from hashlib import sha256
-from typing import Optional
 from urllib.parse import urlencode, urljoin

 from synapse.config import ConfigError
@@ -75,7 +74,7 @@ class LoginSSORedirectURIBuilder:
        self._public_baseurl = hs_config.server.public_baseurl

    def build_login_sso_redirect_uri(
-        self, *, idp_id: Optional[str], client_redirect_url: str
+        self, *, idp_id: str | None, client_redirect_url: str
    ) -> str:
        """Build a `/login/sso/redirect` URI for the given identity provider.

--- a/synapse/app/_base.py
+++ b/synapse/app/_base.py
@@ -36,8 +36,6 @@ from typing import (
    Awaitable,
    Callable,
    NoReturn,
-    Optional,
-    Union,
    cast,
 )
 from wsgiref.simple_server import WSGIServer
@@ -180,8 +178,8 @@ def start_worker_reactor(
 def start_reactor(
    appname: str,
    soft_file_limit: int,
-    gc_thresholds: Optional[tuple[int, int, int]],
-    pid_file: Optional[str],
+    gc_thresholds: tuple[int, int, int] | None,
+    pid_file: str | None,
    daemonize: bool,
    print_pidfile: bool,
    logger: logging.Logger,
@@ -421,7 +419,7 @@ def listen_http(
    root_resource: Resource,
    version_string: str,
    max_request_body_size: int,
-    context_factory: Optional[IOpenSSLContextFactory],
+    context_factory: IOpenSSLContextFactory | None,
    reactor: ISynapseReactor = reactor,
 ) -> list[Port]:
    """
@@ -564,9 +562,7 @@ def setup_sighup_handling() -> None:
    if _already_setup_sighup_handling:
        return

-    previous_sighup_handler: Union[
-        Callable[[int, Optional[FrameType]], Any], int, None
-    ] = None
+    previous_sighup_handler: Callable[[int, FrameType | None], Any] | int | None = None

    # Set up the SIGHUP machinery.
    if hasattr(signal, "SIGHUP"):
--- a/synapse/app/admin_cmd.py
+++ b/synapse/app/admin_cmd.py
@@ -24,7 +24,7 @@ import logging
 import os
 import sys
 import tempfile
-from typing import Mapping, Optional, Sequence
+from typing import Mapping, Sequence

 from twisted.internet import defer, task

@@ -136,7 +136,7 @@ class FileExfiltrationWriter(ExfiltrationWriter):
            to a temporary directory.
    """

-    def __init__(self, user_id: str, directory: Optional[str] = None):
+    def __init__(self, user_id: str, directory: str | None = None):
        self.user_id = user_id

        if directory:
@@ -291,7 +291,7 @@ def load_config(argv_options: list[str]) -> tuple[HomeServerConfig, argparse.Nam

 def create_homeserver(
    config: HomeServerConfig,
-    reactor: Optional[ISynapseReactor] = None,
+    reactor: ISynapseReactor | None = None,
 ) -> AdminCmdServer:
    """
    Create a homeserver instance for the Synapse admin command process.
--- a/synapse/app/complement_fork_starter.py
+++ b/synapse/app/complement_fork_starter.py
@@ -26,7 +26,7 @@ import os
 import signal
 import sys
 from types import FrameType
-from typing import Any, Callable, Optional
+from typing import Any, Callable

 from twisted.internet.main import installReactor

@@ -172,7 +172,7 @@ def main() -> None:
    # Install signal handlers to propagate signals to all our children, so that they
    # shut down cleanly. This also inhibits our own exit, but that's good: we want to
    # wait until the children have exited.
-    def handle_signal(signum: int, frame: Optional[FrameType]) -> None:
+    def handle_signal(signum: int, frame: FrameType | None) -> None:
        print(
            f"complement_fork_starter: Caught signal {signum}. Stopping children.",
            file=sys.stderr,
--- a/synapse/app/generic_worker.py
+++ b/synapse/app/generic_worker.py
@@ -21,7 +21,6 @@
 #
 import logging
 import sys
-from typing import Optional

 from twisted.web.resource import Resource

@@ -336,7 +335,7 @@ def load_config(argv_options: list[str]) -> HomeServerConfig:

 def create_homeserver(
    config: HomeServerConfig,
-    reactor: Optional[ISynapseReactor] = None,
+    reactor: ISynapseReactor | None = None,
 ) -> GenericWorkerServer:
    """
    Create a homeserver instance for the Synapse worker process.
--- a/synapse/app/homeserver.py
+++ b/synapse/app/homeserver.py
@@ -22,7 +22,7 @@
 import logging
 import os
 import sys
-from typing import Iterable, Optional
+from typing import Iterable

 from twisted.internet.tcp import Port
 from twisted.web.resource import EncodingResourceWrapper, Resource
@@ -350,7 +350,7 @@ def load_or_generate_config(argv_options: list[str]) -> HomeServerConfig:

 def create_homeserver(
    config: HomeServerConfig,
-    reactor: Optional[ISynapseReactor] = None,
+    reactor: ISynapseReactor | None = None,
 ) -> SynapseHomeServer:
    """
    Create a homeserver instance for the Synapse main process.
--- a/synapse/appservice/init.py
+++ b/synapse/appservice/init.py
@@ -26,7 +26,6 @@ from enum import Enum
 from typing import (
    TYPE_CHECKING,
    Iterable,
-    Optional,
    Pattern,
    Sequence,
    cast,
@@ -95,12 +94,12 @@ class ApplicationService:
        token: str,
        id: str,
        sender: UserID,
-        url: Optional[str] = None,
-        namespaces: Optional[JsonDict] = None,
-        hs_token: Optional[str] = None,
-        protocols: Optional[Iterable[str]] = None,
+        url: str | None = None,
+        namespaces: JsonDict | None = None,
+        hs_token: str | None = None,
+        protocols: Iterable[str] | None = None,
        rate_limited: bool = True,
-        ip_range_whitelist: Optional[IPSet] = None,
+        ip_range_whitelist: IPSet | None = None,
        supports_ephemeral: bool = False,
        msc3202_transaction_extensions: bool = False,
        msc4190_device_management: bool = False,
@@ -142,7 +141,7 @@ class ApplicationService:
        self.rate_limited = rate_limited

    def _check_namespaces(
-        self, namespaces: Optional[JsonDict]
+        self, namespaces: JsonDict | None
    ) -> dict[str, list[Namespace]]:
        # Sanity check that it is of the form:
        # {
@@ -179,9 +178,7 @@ class ApplicationService:

        return result

-    def _matches_regex(
-        self, namespace_key: str, test_string: str
-    ) -> Optional[Namespace]:
+    def _matches_regex(self, namespace_key: str, test_string: str) -> Namespace | None:
        for namespace in self.namespaces[namespace_key]:
            if namespace.regex.match(test_string):
                return namespace
--- a/synapse/appservice/api.py
+++ b/synapse/appservice/api.py
@@ -25,10 +25,8 @@ from typing import (
    TYPE_CHECKING,
    Iterable,
    Mapping,
-    Optional,
    Sequence,
    TypeVar,
-    Union,
 )

 from prometheus_client import Counter
@@ -222,7 +220,7 @@ class ApplicationServiceApi(SimpleHttpClient):
        assert service.hs_token is not None

        try:
-            args: Mapping[bytes, Union[list[bytes], str]] = fields
+            args: Mapping[bytes, list[bytes] | str] = fields
            if self.config.use_appservice_legacy_authorization:
                args = {
                    **fields,
@@ -258,11 +256,11 @@ class ApplicationServiceApi(SimpleHttpClient):

    async def get_3pe_protocol(
        self, service: "ApplicationService", protocol: str
-    ) -> Optional[JsonDict]:
+    ) -> JsonDict | None:
        if service.url is None:
            return {}

-        async def _get() -> Optional[JsonDict]:
+        async def _get() -> JsonDict | None:
            # This is required by the configuration.
            assert service.hs_token is not None
            try:
@@ -300,7 +298,7 @@ class ApplicationServiceApi(SimpleHttpClient):
        key = (service.id, protocol)
        return await self.protocol_meta_cache.wrap(key, _get)

-    async def ping(self, service: "ApplicationService", txn_id: Optional[str]) -> None:
+    async def ping(self, service: "ApplicationService", txn_id: str | None) -> None:
        # The caller should check that url is set
        assert service.url is not None, "ping called without URL being set"

@@ -322,7 +320,7 @@ class ApplicationServiceApi(SimpleHttpClient):
        one_time_keys_count: TransactionOneTimeKeysCount,
        unused_fallback_keys: TransactionUnusedFallbackKeys,
        device_list_summary: DeviceListUpdates,
-        txn_id: Optional[int] = None,
+        txn_id: int | None = None,
    ) -> bool:
        """
        Push data to an application service.
--- a/synapse/appservice/scheduler.py
+++ b/synapse/appservice/scheduler.py
@@ -62,7 +62,6 @@ from typing import (
    Callable,
    Collection,
    Iterable,
-    Optional,
    Sequence,
 )

@@ -123,10 +122,10 @@ class ApplicationServiceScheduler:
    def enqueue_for_appservice(
        self,
        appservice: ApplicationService,
-        events: Optional[Collection[EventBase]] = None,
-        ephemeral: Optional[Collection[JsonMapping]] = None,
-        to_device_messages: Optional[Collection[JsonMapping]] = None,
-        device_list_summary: Optional[DeviceListUpdates] = None,
+        events: Collection[EventBase] | None = None,
+        ephemeral: Collection[JsonMapping] | None = None,
+        to_device_messages: Collection[JsonMapping] | None = None,
+        device_list_summary: DeviceListUpdates | None = None,
    ) -> None:
        """
        Enqueue some data to be sent off to an application service.
@@ -260,8 +259,8 @@ class _ServiceQueuer:
                ):
                    return

-                one_time_keys_count: Optional[TransactionOneTimeKeysCount] = None
-                unused_fallback_keys: Optional[TransactionUnusedFallbackKeys] = None
+                one_time_keys_count: TransactionOneTimeKeysCount | None = None
+                unused_fallback_keys: TransactionUnusedFallbackKeys | None = None

                if (
                    self._msc3202_transaction_extensions_enabled
@@ -369,11 +368,11 @@ class _TransactionController:
        self,
        service: ApplicationService,
        events: Sequence[EventBase],
-        ephemeral: Optional[list[JsonMapping]] = None,
-        to_device_messages: Optional[list[JsonMapping]] = None,
-        one_time_keys_count: Optional[TransactionOneTimeKeysCount] = None,
-        unused_fallback_keys: Optional[TransactionUnusedFallbackKeys] = None,
-        device_list_summary: Optional[DeviceListUpdates] = None,
+        ephemeral: list[JsonMapping] | None = None,
+        to_device_messages: list[JsonMapping] | None = None,
+        one_time_keys_count: TransactionOneTimeKeysCount | None = None,
+        unused_fallback_keys: TransactionUnusedFallbackKeys | None = None,
+        device_list_summary: DeviceListUpdates | None = None,
    ) -> None:
        """
        Create a transaction with the given data and send to the provided
@@ -504,7 +503,7 @@ class _Recoverer:
        self.service = service
        self.callback = callback
        self.backoff_counter = 1
-        self.scheduled_recovery: Optional[IDelayedCall] = None
+        self.scheduled_recovery: IDelayedCall | None = None

    def recover(self) -> None:
        delay = 2**self.backoff_counter
--- a/synapse/config/_base.py
+++ b/synapse/config/_base.py
@@ -36,9 +36,7 @@ from typing import (
    Iterable,
    Iterator,
    MutableMapping,
-    Optional,
    TypeVar,
-    Union,
 )

 import attr
@@ -60,7 +58,7 @@ class ConfigError(Exception):
           the problem lies.
    """

-    def __init__(self, msg: str, path: Optional[StrSequence] = None):
+    def __init__(self, msg: str, path: StrSequence | None = None):
        self.msg = msg
        self.path = path

@@ -175,7 +173,7 @@ class Config:
        )

    @staticmethod
-    def parse_size(value: Union[str, int]) -> int:
+    def parse_size(value: str | int) -> int:
        """Interpret `value` as a number of bytes.

        If an integer is provided it is treated as bytes and is unchanged.
@@ -202,7 +200,7 @@ class Config:
            raise TypeError(f"Bad byte size {value!r}")

    @staticmethod
-    def parse_duration(value: Union[str, int]) -> int:
+    def parse_duration(value: str | int) -> int:
        """Convert a duration as a string or integer to a number of milliseconds.

        If an integer is provided it is treated as milliseconds and is unchanged.
@@ -270,7 +268,7 @@ class Config:
        return path_exists(file_path)

    @classmethod
-    def check_file(cls, file_path: Optional[str], config_name: str) -> str:
+    def check_file(cls, file_path: str | None, config_name: str) -> str:
        if file_path is None:
            raise ConfigError("Missing config for %s." % (config_name,))
        try:
@@ -318,7 +316,7 @@ class Config:
    def read_templates(
        self,
        filenames: list[str],
-        custom_template_directories: Optional[Iterable[str]] = None,
+        custom_template_directories: Iterable[str] | None = None,
    ) -> list[jinja2.Template]:
        """Load a list of template files from disk using the given variables.

@@ -465,11 +463,11 @@ class RootConfig:
        data_dir_path: str,
        server_name: str,
        generate_secrets: bool = False,
-        report_stats: Optional[bool] = None,
+        report_stats: bool | None = None,
        open_private_ports: bool = False,
-        listeners: Optional[list[dict]] = None,
-        tls_certificate_path: Optional[str] = None,
-        tls_private_key_path: Optional[str] = None,
+        listeners: list[dict] | None = None,
+        tls_certificate_path: str | None = None,
+        tls_private_key_path: str | None = None,
    ) -> str:
        """
        Build a default configuration file
@@ -655,7 +653,7 @@ class RootConfig:
    @classmethod
    def load_or_generate_config(
        cls: type[TRootConfig], description: str, argv_options: list[str]
-    ) -> Optional[TRootConfig]:
+    ) -> TRootConfig | None:
        """Parse the commandline and config files

        Supports generation of config files, so is used for the main homeserver app.
@@ -898,7 +896,7 @@ class RootConfig:
        :returns: the previous config object, which no longer has a reference to this
            RootConfig.
        """
-        existing_config: Optional[Config] = getattr(self, section_name, None)
+        existing_config: Config | None = getattr(self, section_name, None)
        if existing_config is None:
            raise ValueError(f"Unknown config section '{section_name}'")
        logger.info("Reloading config section '%s'", section_name)
--- a/synapse/config/_base.pyi
+++ b/synapse/config/_base.pyi
@@ -6,9 +6,7 @@ from typing import (
    Iterator,
    Literal,
    MutableMapping,
-    Optional,
    TypeVar,
-    Union,
    overload,
 )

@@ -64,7 +62,7 @@ from synapse.config import (  # noqa: F401
 from synapse.types import StrSequence

 class ConfigError(Exception):
-    def __init__(self, msg: str, path: Optional[StrSequence] = None):
+    def __init__(self, msg: str, path: StrSequence | None = None):
        self.msg = msg
        self.path = path

@@ -146,16 +144,16 @@ class RootConfig:
        data_dir_path: str,
        server_name: str,
        generate_secrets: bool = ...,
-        report_stats: Optional[bool] = ...,
+        report_stats: bool | None = ...,
        open_private_ports: bool = ...,
-        listeners: Optional[Any] = ...,
-        tls_certificate_path: Optional[str] = ...,
-        tls_private_key_path: Optional[str] = ...,
+        listeners: Any | None = ...,
+        tls_certificate_path: str | None = ...,
+        tls_private_key_path: str | None = ...,
    ) -> str: ...
    @classmethod
    def load_or_generate_config(
        cls: type[TRootConfig], description: str, argv_options: list[str]
-    ) -> Optional[TRootConfig]: ...
+    ) -> TRootConfig | None: ...
    @classmethod
    def load_config(
        cls: type[TRootConfig], description: str, argv_options: list[str]
@@ -183,11 +181,11 @@ class Config:
    default_template_dir: str
    def __init__(self, root_config: RootConfig = ...) -> None: ...
    @staticmethod
-    def parse_size(value: Union[str, int]) -> int: ...
+    def parse_size(value: str | int) -> int: ...
    @staticmethod
-    def parse_duration(value: Union[str, int]) -> int: ...
+    def parse_duration(value: str | int) -> int: ...
    @staticmethod
-    def abspath(file_path: Optional[str]) -> str: ...
+    def abspath(file_path: str | None) -> str: ...
    @classmethod
    def path_exists(cls, file_path: str) -> bool: ...
    @classmethod
@@ -200,7 +198,7 @@ class Config:
    def read_templates(
        self,
        filenames: list[str],
-        custom_template_directories: Optional[Iterable[str]] = None,
+        custom_template_directories: Iterable[str] | None = None,
    ) -> list[jinja2.Template]: ...

 def read_config_files(config_files: Iterable[str]) -> dict[str, Any]: ...
--- a/synapse/config/api.py
+++ b/synapse/config/api.py
@@ -20,7 +20,7 @@
 #

 import logging
-from typing import Any, Iterable, Optional
+from typing import Any, Iterable

 from synapse.api.constants import EventTypes
 from synapse.config._base import Config, ConfigError
@@ -46,7 +46,7 @@ class ApiConfig(Config):

    def _get_prejoin_state_entries(
        self, config: JsonDict
-    ) -> Iterable[tuple[str, Optional[str]]]:
+    ) -> Iterable[tuple[str, str | None]]:
        """Get the event types and state keys to include in the prejoin state."""
        room_prejoin_state_config = config.get("room_prejoin_state") or {}

--- a/synapse/config/cache.py
+++ b/synapse/config/cache.py
@@ -23,7 +23,7 @@ import logging
 import os
 import re
 import threading
-from typing import Any, Callable, Mapping, Optional
+from typing import Any, Callable, Mapping

 import attr

@@ -53,7 +53,7 @@ class CacheProperties:
    default_factor_size: float = float(
        os.environ.get(_CACHE_PREFIX, _DEFAULT_FACTOR_SIZE)
    )
-    resize_all_caches_func: Optional[Callable[[], None]] = None
+    resize_all_caches_func: Callable[[], None] | None = None


 properties = CacheProperties()
@@ -107,7 +107,7 @@ class CacheConfig(Config):
    cache_factors: dict[str, float]
    global_factor: float
    track_memory_usage: bool
-    expiry_time_msec: Optional[int]
+    expiry_time_msec: int | None
    sync_response_cache_duration: int

    @staticmethod
--- a/synapse/config/cas.py
+++ b/synapse/config/cas.py
@@ -20,7 +20,7 @@
 #
 #

-from typing import Any, Optional
+from typing import Any

 from synapse.config.sso import SsoAttributeRequirement
 from synapse.types import JsonDict
@@ -49,7 +49,7 @@ class CasConfig(Config):

            # TODO Update this to a _synapse URL.
            public_baseurl = self.root.server.public_baseurl
-            self.cas_service_url: Optional[str] = (
+            self.cas_service_url: str | None = (
                public_baseurl + "_matrix/client/r0/login/cas/ticket"
            )

--- a/synapse/config/consent.py
+++ b/synapse/config/consent.py
@@ -19,7 +19,7 @@
 #

 from os import path
-from typing import Any, Optional
+from typing import Any

 from synapse.config import ConfigError
 from synapse.types import JsonDict
@@ -33,11 +33,11 @@ class ConsentConfig(Config):
    def __init__(self, *args: Any):
        super().__init__(*args)

-        self.user_consent_version: Optional[str] = None
-        self.user_consent_template_dir: Optional[str] = None
-        self.user_consent_server_notice_content: Optional[JsonDict] = None
+        self.user_consent_version: str | None = None
+        self.user_consent_template_dir: str | None = None
+        self.user_consent_server_notice_content: JsonDict | None = None
        self.user_consent_server_notice_to_guests = False
-        self.block_events_without_consent_error: Optional[str] = None
+        self.block_events_without_consent_error: str | None = None
        self.user_consent_at_registration = False
        self.user_consent_policy_name = "Privacy Policy"

--- a/synapse/config/experimental.py
+++ b/synapse/config/experimental.py
@@ -59,7 +59,7 @@ class ClientAuthMethod(enum.Enum):
    PRIVATE_KEY_JWT = "private_key_jwt"


-def _parse_jwks(jwks: Optional[JsonDict]) -> Optional["JsonWebKey"]:
+def _parse_jwks(jwks: JsonDict | None) -> Optional["JsonWebKey"]:
    """A helper function to parse a JWK dict into a JsonWebKey."""

    if jwks is None:
@@ -71,7 +71,7 @@ def _parse_jwks(jwks: Optional[JsonDict]) -> Optional["JsonWebKey"]:


 def _check_client_secret(
-    instance: "MSC3861", _attribute: attr.Attribute, _value: Optional[str]
+    instance: "MSC3861", _attribute: attr.Attribute, _value: str | None
 ) -> None:
    if instance._client_secret and instance._client_secret_path:
        raise ConfigError(
@@ -88,7 +88,7 @@ def _check_client_secret(


 def _check_admin_token(
-    instance: "MSC3861", _attribute: attr.Attribute, _value: Optional[str]
+    instance: "MSC3861", _attribute: attr.Attribute, _value: str | None
 ) -> None:
    if instance._admin_token and instance._admin_token_path:
        raise ConfigError(
@@ -124,7 +124,7 @@ class MSC3861:
    issuer: str = attr.ib(default="", validator=attr.validators.instance_of(str))
    """The URL of the OIDC Provider."""

-    issuer_metadata: Optional[JsonDict] = attr.ib(default=None)
+    issuer_metadata: JsonDict | None = attr.ib(default=None)
    """The issuer metadata to use, otherwise discovered from /.well-known/openid-configuration as per MSC2965."""

    client_id: str = attr.ib(
@@ -138,7 +138,7 @@ class MSC3861:
    )
    """The auth method used when calling the introspection endpoint."""

-    _client_secret: Optional[str] = attr.ib(
+    _client_secret: str | None = attr.ib(
        default=None,
        validator=[
            attr.validators.optional(attr.validators.instance_of(str)),
@@ -150,7 +150,7 @@ class MSC3861:
    when using any of the client_secret_* client auth methods.
    """

-    _client_secret_path: Optional[str] = attr.ib(
+    _client_secret_path: str | None = attr.ib(
        default=None,
        validator=[
            attr.validators.optional(attr.validators.instance_of(str)),
@@ -196,19 +196,19 @@ class MSC3861:
                ("experimental", "msc3861", "client_auth_method"),
            )

-    introspection_endpoint: Optional[str] = attr.ib(
+    introspection_endpoint: str | None = attr.ib(
        default=None,
        validator=attr.validators.optional(attr.validators.instance_of(str)),
    )
    """The URL of the introspection endpoint used to validate access tokens."""

-    account_management_url: Optional[str] = attr.ib(
+    account_management_url: str | None = attr.ib(
        default=None,
        validator=attr.validators.optional(attr.validators.instance_of(str)),
    )
    """The URL of the My Account page on the OIDC Provider as per MSC2965."""

-    _admin_token: Optional[str] = attr.ib(
+    _admin_token: str | None = attr.ib(
        default=None,
        validator=[
            attr.validators.optional(attr.validators.instance_of(str)),
@@ -220,7 +220,7 @@ class MSC3861:
    This is used by the OIDC provider, to make admin calls to Synapse.
    """

-    _admin_token_path: Optional[str] = attr.ib(
+    _admin_token_path: str | None = attr.ib(
        default=None,
        validator=[
            attr.validators.optional(attr.validators.instance_of(str)),
@@ -232,7 +232,7 @@ class MSC3861:
    external file.
    """

-    def client_secret(self) -> Optional[str]:
+    def client_secret(self) -> str | None:
        """Returns the secret given via `client_secret` or `client_secret_path`."""
        if self._client_secret_path:
            return read_secret_from_file_once(
@@ -241,7 +241,7 @@ class MSC3861:
            )
        return self._client_secret

-    def admin_token(self) -> Optional[str]:
+    def admin_token(self) -> str | None:
        """Returns the admin token given via `admin_token` or `admin_token_path`."""
        if self._admin_token_path:
            return read_secret_from_file_once(
@@ -526,7 +526,7 @@ class ExperimentalConfig(Config):
        # MSC4108: Mechanism to allow OIDC sign in and E2EE set up via QR code
        self.msc4108_enabled = experimental.get("msc4108_enabled", False)

-        self.msc4108_delegation_endpoint: Optional[str] = experimental.get(
+        self.msc4108_delegation_endpoint: str | None = experimental.get(
            "msc4108_delegation_endpoint", None
        )

--- a/synapse/config/federation.py
+++ b/synapse/config/federation.py
@@ -18,7 +18,7 @@
 # [This file includes modifications made by New Vector Limited]
 #
 #
-from typing import Any, Optional
+from typing import Any

 from synapse.config._base import Config
 from synapse.config._util import validate_config
@@ -32,7 +32,7 @@ class FederationConfig(Config):
        federation_config = config.setdefault("federation", {})

        # FIXME: federation_domain_whitelist needs sytests
-        self.federation_domain_whitelist: Optional[dict] = None
+        self.federation_domain_whitelist: dict | None = None
        federation_domain_whitelist = config.get("federation_domain_whitelist", None)

        if federation_domain_whitelist is not None:
--- a/synapse/config/key.py
+++ b/synapse/config/key.py
@@ -23,7 +23,7 @@
 import hashlib
 import logging
 import os
-from typing import TYPE_CHECKING, Any, Iterator, Optional
+from typing import TYPE_CHECKING, Any, Iterator

 import attr
 import jsonschema
@@ -110,7 +110,7 @@ class TrustedKeyServer:
    server_name: str

    # map from key id to key object, or None to disable signature verification.
-    verify_keys: Optional[dict[str, VerifyKey]] = None
+    verify_keys: dict[str, VerifyKey] | None = None


 class KeyConfig(Config):
@@ -219,7 +219,7 @@ class KeyConfig(Config):
        if form_secret_path:
            if form_secret:
                raise ConfigError(CONFLICTING_FORM_SECRET_OPTS_ERROR)
-            self.form_secret: Optional[str] = read_file(
+            self.form_secret: str | None = read_file(
                form_secret_path, ("form_secret_path",)
            ).strip()
        else:
@@ -279,7 +279,7 @@ class KeyConfig(Config):
            raise ConfigError("Error reading %s: %s" % (name, str(e)))

    def read_old_signing_keys(
-        self, old_signing_keys: Optional[JsonDict]
+        self, old_signing_keys: JsonDict | None
    ) -> dict[str, "VerifyKeyWithExpiry"]:
        if old_signing_keys is None:
            return {}
@@ -408,7 +408,7 @@ def _parse_key_servers(
        server_name = server["server_name"]
        result = TrustedKeyServer(server_name=server_name)

-        verify_keys: Optional[dict[str, str]] = server.get("verify_keys")
+        verify_keys: dict[str, str] | None = server.get("verify_keys")
        if verify_keys is not None:
            result.verify_keys = {}
            for key_id, key_base64 in verify_keys.items():
--- a/synapse/config/logger.py
+++ b/synapse/config/logger.py
@@ -26,7 +26,7 @@ import os
 import sys
 import threading
 from string import Template
-from typing import TYPE_CHECKING, Any, Optional
+from typing import TYPE_CHECKING, Any

 import yaml
 from zope.interface import implementer
@@ -280,7 +280,7 @@ def one_time_logging_setup(*, logBeginner: LogBeginner = globalLogBeginner) -> N


 def _setup_stdlib_logging(
-    config: "HomeServerConfig", log_config_path: Optional[str]
+    config: "HomeServerConfig", log_config_path: str | None
 ) -> None:
    """
    Set up Python standard library logging.
@@ -327,7 +327,7 @@ def _load_logging_config(log_config_path: str) -> None:
    reset_logging_config()


-def _reload_logging_config(log_config_path: Optional[str]) -> None:
+def _reload_logging_config(log_config_path: str | None) -> None:
    """
    Reload the log configuration from the file and apply it.
    """
--- a/synapse/config/mas.py
+++ b/synapse/config/mas.py
@@ -13,7 +13,7 @@
 #
 #

-from typing import Any, Optional
+from typing import Any

 from pydantic import (
    AnyHttpUrl,
@@ -36,9 +36,9 @@ from ._base import Config, ConfigError, RootConfig
 class MasConfigModel(ParseModel):
    enabled: StrictBool = False
    endpoint: AnyHttpUrl = AnyHttpUrl("http://localhost:8080")
-    secret: Optional[StrictStr] = Field(default=None)
+    secret: StrictStr | None = Field(default=None)
    # We set `strict=False` to allow `str` instances.
-    secret_path: Optional[FilePath] = Field(default=None, strict=False)
+    secret_path: FilePath | None = Field(default=None, strict=False)

    @model_validator(mode="after")
    def verify_secret(self) -> Self:
--- a/synapse/config/matrixrtc.py
+++ b/synapse/config/matrixrtc.py
@@ -15,7 +15,7 @@
 #
 #

-from typing import Any, Optional
+from typing import Any

 from pydantic import Field, StrictStr, ValidationError, model_validator
 from typing_extensions import Self
@@ -29,7 +29,7 @@ from ._base import Config, ConfigError
 class TransportConfigModel(ParseModel):
    type: StrictStr

-    livekit_service_url: Optional[StrictStr] = Field(default=None)
+    livekit_service_url: StrictStr | None = Field(default=None)
    """An optional livekit service URL. Only required if type is "livekit"."""

    @model_validator(mode="after")
--- a/synapse/config/metrics.py
+++ b/synapse/config/metrics.py
@@ -20,7 +20,7 @@
 #
 #

-from typing import Any, Optional
+from typing import Any

 import attr

@@ -75,7 +75,7 @@ class MetricsConfig(Config):
                )

    def generate_config_section(
-        self, report_stats: Optional[bool] = None, **kwargs: Any
+        self, report_stats: bool | None = None, **kwargs: Any
    ) -> str:
        if report_stats is not None:
            res = "report_stats: %s\n" % ("true" if report_stats else "false")
--- a/synapse/config/oembed.py
+++ b/synapse/config/oembed.py
@@ -21,7 +21,7 @@
 import importlib.resources as importlib_resources
 import json
 import re
-from typing import Any, Iterable, Optional, Pattern
+from typing import Any, Iterable, Pattern
 from urllib import parse as urlparse

 import attr
@@ -39,7 +39,7 @@ class OEmbedEndpointConfig:
    # The patterns to match.
    url_patterns: list[Pattern[str]]
    # The supported formats.
-    formats: Optional[list[str]]
+    formats: list[str] | None


 class OembedConfig(Config):
--- a/synapse/config/oidc.py
+++ b/synapse/config/oidc.py
@@ -21,7 +21,7 @@
 #

 from collections import Counter
-from typing import Any, Collection, Iterable, Mapping, Optional
+from typing import Any, Collection, Iterable, Mapping

 import attr

@@ -276,7 +276,7 @@ def _parse_oidc_config_dict(
            ) from e

    client_secret_jwt_key_config = oidc_config.get("client_secret_jwt_key")
-    client_secret_jwt_key: Optional[OidcProviderClientSecretJwtKey] = None
+    client_secret_jwt_key: OidcProviderClientSecretJwtKey | None = None
    if client_secret_jwt_key_config is not None:
        keyfile = client_secret_jwt_key_config.get("key_file")
        if keyfile:
@@ -384,10 +384,10 @@ class OidcProviderConfig:
    idp_name: str

    # Optional MXC URI for icon for this IdP.
-    idp_icon: Optional[str]
+    idp_icon: str | None

    # Optional brand identifier for this IdP.
-    idp_brand: Optional[str]
+    idp_brand: str | None

    # whether the OIDC discovery mechanism is used to discover endpoints
    discover: bool
@@ -401,11 +401,11 @@ class OidcProviderConfig:

    # oauth2 client secret to use. if `None`, use client_secret_jwt_key to generate
    # a secret.
-    client_secret: Optional[str]
+    client_secret: str | None

    # key to use to construct a JWT to use as a client secret. May be `None` if
    # `client_secret` is set.
-    client_secret_jwt_key: Optional[OidcProviderClientSecretJwtKey]
+    client_secret_jwt_key: OidcProviderClientSecretJwtKey | None

    # auth method to use when exchanging the token.
    # Valid values are 'client_secret_basic', 'client_secret_post' and
@@ -416,7 +416,7 @@ class OidcProviderConfig:
    # Valid values are 'auto', 'always', and 'never'.
    pkce_method: str

-    id_token_signing_alg_values_supported: Optional[list[str]]
+    id_token_signing_alg_values_supported: list[str] | None
    """
    List of the JWS signing algorithms (`alg` values) that are supported for signing the
    `id_token`.
@@ -448,18 +448,18 @@ class OidcProviderConfig:
    scopes: Collection[str]

    # the oauth2 authorization endpoint. Required if discovery is disabled.
-    authorization_endpoint: Optional[str]
+    authorization_endpoint: str | None

    # the oauth2 token endpoint. Required if discovery is disabled.
-    token_endpoint: Optional[str]
+    token_endpoint: str | None

    # the OIDC userinfo endpoint. Required if discovery is disabled and the
    # "openid" scope is not requested.
-    userinfo_endpoint: Optional[str]
+    userinfo_endpoint: str | None

    # URI where to fetch the JWKS. Required if discovery is disabled and the
    # "openid" scope is used.
-    jwks_uri: Optional[str]
+    jwks_uri: str | None

    # Whether Synapse should react to backchannel logouts
    backchannel_logout_enabled: bool
@@ -474,7 +474,7 @@ class OidcProviderConfig:
    # values are: "auto" or "userinfo_endpoint".
    user_profile_method: str

-    redirect_uri: Optional[str]
+    redirect_uri: str | None
    """
    An optional replacement for Synapse's hardcoded `redirect_uri` URL
    (`<public_baseurl>/_synapse/client/oidc/callback`). This can be used to send
--- a/synapse/config/ratelimiting.py
+++ b/synapse/config/ratelimiting.py
@@ -19,7 +19,7 @@
 #
 #

-from typing import Any, Optional, cast
+from typing import Any, cast

 import attr

@@ -39,7 +39,7 @@ class RatelimitSettings:
        cls,
        config: dict[str, Any],
        key: str,
-        defaults: Optional[dict[str, float]] = None,
+        defaults: dict[str, float] | None = None,
    ) -> "RatelimitSettings":
        """Parse config[key] as a new-style rate limiter config.

--- a/synapse/config/registration.py
+++ b/synapse/config/registration.py
@@ -20,7 +20,7 @@
 #
 #
 import argparse
-from typing import Any, Optional
+from typing import Any

 from synapse.api.constants import RoomCreationPreset
 from synapse.config._base import Config, ConfigError, read_file
@@ -181,7 +181,7 @@ class RegistrationConfig(Config):
            refreshable_access_token_lifetime = self.parse_duration(
                refreshable_access_token_lifetime
            )
-        self.refreshable_access_token_lifetime: Optional[int] = (
+        self.refreshable_access_token_lifetime: int | None = (
            refreshable_access_token_lifetime
        )

@@ -226,7 +226,7 @@ class RegistrationConfig(Config):
        refresh_token_lifetime = config.get("refresh_token_lifetime")
        if refresh_token_lifetime is not None:
            refresh_token_lifetime = self.parse_duration(refresh_token_lifetime)
-        self.refresh_token_lifetime: Optional[int] = refresh_token_lifetime
+        self.refresh_token_lifetime: int | None = refresh_token_lifetime

        if (
            self.session_lifetime is not None
--- a/synapse/config/retention.py
+++ b/synapse/config/retention.py
@@ -20,7 +20,7 @@
 #

 import logging
-from typing import Any, Optional
+from typing import Any

 import attr

@@ -35,8 +35,8 @@ class RetentionPurgeJob:
    """Object describing the configuration of the manhole"""

    interval: int
-    shortest_max_lifetime: Optional[int]
-    longest_max_lifetime: Optional[int]
+    shortest_max_lifetime: int | None
+    longest_max_lifetime: int | None


 class RetentionConfig(Config):
--- a/synapse/config/server.py
+++ b/synapse/config/server.py
@@ -25,7 +25,7 @@ import logging
 import os.path
 import urllib.parse
 from textwrap import indent
-from typing import Any, Iterable, Optional, TypedDict, Union
+from typing import Any, Iterable, TypedDict
 from urllib.request import getproxies_environment

 import attr
@@ -95,9 +95,9 @@ def _6to4(network: IPNetwork) -> IPNetwork:


 def generate_ip_set(
-    ip_addresses: Optional[Iterable[str]],
-    extra_addresses: Optional[Iterable[str]] = None,
-    config_path: Optional[StrSequence] = None,
+    ip_addresses: Iterable[str] | None,
+    extra_addresses: Iterable[str] | None = None,
+    config_path: StrSequence | None = None,
 ) -> IPSet:
    """
    Generate an IPSet from a list of IP addresses or CIDRs.
@@ -230,8 +230,8 @@ class HttpListenerConfig:
    x_forwarded: bool = False
    resources: list[HttpResourceConfig] = attr.Factory(list)
    additional_resources: dict[str, dict] = attr.Factory(dict)
-    tag: Optional[str] = None
-    request_id_header: Optional[str] = None
+    tag: str | None = None
+    request_id_header: str | None = None


@attr.s(slots=True, frozen=True, auto_attribs=True)
@@ -244,7 +244,7 @@ class TCPListenerConfig:
    tls: bool = False

    # http_options is only populated if type=http
-    http_options: Optional[HttpListenerConfig] = None
+    http_options: HttpListenerConfig | None = None

    def get_site_tag(self) -> str:
        """Retrieves http_options.tag if it exists, otherwise the port number."""
@@ -269,7 +269,7 @@ class UnixListenerConfig:
    type: str = attr.ib(validator=attr.validators.in_(KNOWN_LISTENER_TYPES))

    # http_options is only populated if type=http
-    http_options: Optional[HttpListenerConfig] = None
+    http_options: HttpListenerConfig | None = None

    def get_site_tag(self) -> str:
        return "unix"
@@ -279,7 +279,7 @@ class UnixListenerConfig:
        return False


-ListenerConfig = Union[TCPListenerConfig, UnixListenerConfig]
+ListenerConfig = TCPListenerConfig | UnixListenerConfig


@attr.s(slots=True, frozen=True, auto_attribs=True)
@@ -288,14 +288,14 @@ class ManholeConfig:

    username: str = attr.ib(validator=attr.validators.instance_of(str))
    password: str = attr.ib(validator=attr.validators.instance_of(str))
-    priv_key: Optional[Key]
-    pub_key: Optional[Key]
+    priv_key: Key | None
+    pub_key: Key | None


@attr.s(frozen=True)
 class LimitRemoteRoomsConfig:
    enabled: bool = attr.ib(validator=attr.validators.instance_of(bool), default=False)
-    complexity: Union[float, int] = attr.ib(
+    complexity: float | int = attr.ib(
        validator=attr.validators.instance_of((float, int)),  # noqa
        default=1.0,
    )
@@ -313,11 +313,11 @@ class ProxyConfigDictionary(TypedDict):
    Dictionary of proxy settings suitable for interacting with `urllib.request` API's
    """

-    http: Optional[str]
+    http: str | None
    """
    Proxy server to use for HTTP requests.
    """
-    https: Optional[str]
+    https: str | None
    """
    Proxy server to use for HTTPS requests.
    """
@@ -336,15 +336,15 @@ class ProxyConfig:
    Synapse configuration for HTTP proxy settings.
    """

-    http_proxy: Optional[str]
+    http_proxy: str | None
    """
    Proxy server to use for HTTP requests.
    """
-    https_proxy: Optional[str]
+    https_proxy: str | None
    """
    Proxy server to use for HTTPS requests.
    """
-    no_proxy_hosts: Optional[list[str]]
+    no_proxy_hosts: list[str] | None
    """
    List of hosts, IP addresses, or IP ranges in CIDR format which should not use the
    proxy. Synapse will directly connect to these hosts.
@@ -607,7 +607,7 @@ class ServerConfig(Config):
        # before redacting them.
        redaction_retention_period = config.get("redaction_retention_period", "7d")
        if redaction_retention_period is not None:
-            self.redaction_retention_period: Optional[int] = self.parse_duration(
+            self.redaction_retention_period: int | None = self.parse_duration(
                redaction_retention_period
            )
        else:
@@ -618,7 +618,7 @@ class ServerConfig(Config):
            "forgotten_room_retention_period", None
        )
        if forgotten_room_retention_period is not None:
-            self.forgotten_room_retention_period: Optional[int] = self.parse_duration(
+            self.forgotten_room_retention_period: int | None = self.parse_duration(
                forgotten_room_retention_period
            )
        else:
@@ -627,7 +627,7 @@ class ServerConfig(Config):
        # How long to keep entries in the `users_ips` table.
        user_ips_max_age = config.get("user_ips_max_age", "28d")
        if user_ips_max_age is not None:
-            self.user_ips_max_age: Optional[int] = self.parse_duration(user_ips_max_age)
+            self.user_ips_max_age: int | None = self.parse_duration(user_ips_max_age)
        else:
            self.user_ips_max_age = None

@@ -864,11 +864,11 @@ class ServerConfig(Config):
        )

        # Whitelist of domain names that given next_link parameters must have
-        next_link_domain_whitelist: Optional[list[str]] = config.get(
+        next_link_domain_whitelist: list[str] | None = config.get(
            "next_link_domain_whitelist"
        )

-        self.next_link_domain_whitelist: Optional[set[str]] = None
+        self.next_link_domain_whitelist: set[str] | None = None
        if next_link_domain_whitelist is not None:
            if not isinstance(next_link_domain_whitelist, list):
                raise ConfigError("'next_link_domain_whitelist' must be a list")
@@ -880,7 +880,7 @@ class ServerConfig(Config):
        if not isinstance(templates_config, dict):
            raise ConfigError("The 'templates' section must be a dictionary")

-        self.custom_template_directory: Optional[str] = templates_config.get(
+        self.custom_template_directory: str | None = templates_config.get(
            "custom_template_directory"
        )
        if self.custom_template_directory is not None and not isinstance(
@@ -896,12 +896,12 @@ class ServerConfig(Config):
            config.get("exclude_rooms_from_sync") or []
        )

-        delete_stale_devices_after: Optional[str] = (
+        delete_stale_devices_after: str | None = (
            config.get("delete_stale_devices_after") or None
        )

        if delete_stale_devices_after is not None:
-            self.delete_stale_devices_after: Optional[int] = self.parse_duration(
+            self.delete_stale_devices_after: int | None = self.parse_duration(
                delete_stale_devices_after
            )
        else:
@@ -910,7 +910,7 @@ class ServerConfig(Config):
        # The maximum allowed delay duration for delayed events (MSC4140).
        max_event_delay_duration = config.get("max_event_delay_duration")
        if max_event_delay_duration is not None:
-            self.max_event_delay_ms: Optional[int] = self.parse_duration(
+            self.max_event_delay_ms: int | None = self.parse_duration(
                max_event_delay_duration
            )
            if self.max_event_delay_ms <= 0:
@@ -927,7 +927,7 @@ class ServerConfig(Config):
        data_dir_path: str,
        server_name: str,
        open_private_ports: bool,
-        listeners: Optional[list[dict]],
+        listeners: list[dict] | None,
        **kwargs: Any,
    ) -> str:
        _, bind_port = parse_and_validate_server_name(server_name)
@@ -1028,7 +1028,7 @@ class ServerConfig(Config):
            help="Turn on the twisted telnet manhole service on the given port.",
        )

-    def read_gc_intervals(self, durations: Any) -> Optional[tuple[float, float, float]]:
+    def read_gc_intervals(self, durations: Any) -> tuple[float, float, float] | None:
        """Reads the three durations for the GC min interval option, returning seconds."""
        if durations is None:
            return None
@@ -1066,8 +1066,8 @@ def is_threepid_reserved(


 def read_gc_thresholds(
-    thresholds: Optional[list[Any]],
-) -> Optional[tuple[int, int, int]]:
+    thresholds: list[Any] | None,
+) -> tuple[int, int, int] | None:
    """Reads the three integer thresholds for garbage collection. Ensures that
    the thresholds are integers if thresholds are supplied.
    """
--- a/synapse/config/server_notices.py
+++ b/synapse/config/server_notices.py
@@ -18,7 +18,7 @@
 #
 #

-from typing import Any, Optional
+from typing import Any

 from synapse.types import JsonDict, UserID

@@ -58,12 +58,12 @@ class ServerNoticesConfig(Config):

    def __init__(self, *args: Any):
        super().__init__(*args)
-        self.server_notices_mxid: Optional[str] = None
-        self.server_notices_mxid_display_name: Optional[str] = None
-        self.server_notices_mxid_avatar_url: Optional[str] = None
-        self.server_notices_room_name: Optional[str] = None
-        self.server_notices_room_avatar_url: Optional[str] = None
-        self.server_notices_room_topic: Optional[str] = None
+        self.server_notices_mxid: str | None = None
+        self.server_notices_mxid_display_name: str | None = None
+        self.server_notices_mxid_avatar_url: str | None = None
+        self.server_notices_room_name: str | None = None
+        self.server_notices_room_avatar_url: str | None = None
+        self.server_notices_room_topic: str | None = None
        self.server_notices_auto_join: bool = False

    def read_config(self, config: JsonDict, **kwargs: Any) -> None:
--- a/Show More
+++ b/Show More
				`@@ -0,0 +1 @@`
				Support multiple config files in `register_new_matrix_user`.
				`@@ -0,0 +1 @@`
				`Improve documentation around streams, particularly ID generators and adding new streams.`
				`@@ -0,0 +1 @@`
				Write union types as `X \| Y` where possible, as per PEP 604, added in Python 3.10.
				`@@ -0,0 +1 @@`
				Reduce cardinality of `synapse_storage_events_persisted_events_sep_total` metric by removing `origin_entity` label. This also separates out events sent by local application services by changing the `origin_type` for such events to `application_service`. The `type` field also only tracks common event types, and anything else is bucketed under `other`.
				`@@ -0,0 +1 @@`
				Update `pyproject.toml` project metadata to be compatible with standard Python packaging tooling.
				`@@ -0,0 +1 @@`
				`Minor speed up of processing of inbound replication.`
				`@@ -0,0 +1 @@`
				Ignore recent Python language refactors from git blame (`.git-blame-ignore-revs`).
				`@@ -0,0 +1 @@`
				Let the SQLite-to-PostgreSQL migration script correctly migrate a boolean column in the `delayed_events` table.
				`@@ -0,0 +1 @@`
				Bump lower bounds of dependencies `parameterized` to `0.9.0` and `idna` to `3.3` as those are the first to advertise support for Python 3.10.