Cherry-pick "Run trial tests against Python 3.11 (#13812)" and fixup commit

4f5d492cd6a9438de03d1b768f4c220cb662ac06

The release branch CI is failing because poetry seems unable to install
wrapt 1.13.3 when run under CPython 3.11. Develop has already bumped
wrapt for 3.11 compatibility. Cherry-pick that commit here to try and
get CI going again.

5 files changed, 146 insertions, 94 deletions

diff --git a/.ci/scripts/calculate_jobs.py b/.ci/scripts/calculate_jobs.py
index c2198e0dd4..c53d4d5ff1 100755
--- a/.ci/scripts/calculate_jobs.py
+++ b/.ci/scripts/calculate_jobs.py
@@ -46,7 +46,7 @@ if not IS_PR:
             "database": "sqlite",
             "extras": "all",
         }
-        for version in ("3.8", "3.9", "3.10")
+        for version in ("3.8", "3.9", "3.10", "3.11")
     )
 
 
@@ -62,7 +62,7 @@ trial_postgres_tests = [
 if not IS_PR:
     trial_postgres_tests.append(
         {
-            "python-version": "3.10",
+            "python-version": "3.11",
             "database": "postgres",
             "postgres-version": "14",
             "extras": "all",
diff --git a/.github/workflows/tests.yml b/.github/workflows/tests.yml
index ff5cf0c534..27fef6b5bd 100644
--- a/.github/workflows/tests.yml
+++ b/.github/workflows/tests.yml
@@ -393,7 +393,7 @@ jobs:
           - python-version: "3.7"
             postgres-version: "10"
 
-          - python-version: "3.10"
+          - python-version: "3.11"
             postgres-version: "14"
 
     services:
diff --git a/changelog.d/13812.misc b/changelog.d/13812.misc
new file mode 100644
index 0000000000..667fdee2b7
--- /dev/null
+++ b/changelog.d/13812.misc
@@ -0,0 +1 @@
+Run unit tests against Python 3.11.
diff --git a/poetry.lock b/poetry.lock
index c01cfcfa58..ebabd3b833 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -25,7 +25,7 @@ cryptography = ">=3.2"
 
 [[package]]
 name = "automat"
-version = "20.2.0"
+version = "22.10.0"
 description = "Self-service finite-state machines for the programmer on the go."
 category = "main"
 optional = false
@@ -671,12 +671,16 @@ python-versions = "*"
 
 [[package]]
 name = "pillow"
-version = "9.0.1"
+version = "9.2.0"
 description = "Python Imaging Library (Fork)"
 category = "main"
 optional = false
 python-versions = ">=3.7"
 
+[package.extras]
+docs = ["furo", "olefile", "sphinx (>=2.4)", "sphinx-copybutton", "sphinx-issues (>=3.0.1)", "sphinx-removed-in", "sphinxext-opengraph"]
+tests = ["check-manifest", "coverage", "defusedxml", "markdown2", "olefile", "packaging", "pyroma", "pytest", "pytest-cov", "pytest-timeout"]
+
 [[package]]
 name = "pkginfo"
 version = "1.8.2"
@@ -1534,7 +1538,7 @@ python-versions = "*"
 
 [[package]]
 name = "wrapt"
-version = "1.13.3"
+version = "1.14.1"
 description = "Module for decorators, wrappers and monkey patching."
 category = "dev"
 optional = false
@@ -1646,8 +1650,8 @@ Authlib = [
     {file = "Authlib-1.1.0.tar.gz", hash = "sha256:0a270c91409fc2b7b0fbee6996e09f2ee3187358762111a9a4225c874b94e891"},
 ]
 automat = [
-    {file = "Automat-20.2.0-py2.py3-none-any.whl", hash = "sha256:b6feb6455337df834f6c9962d6ccf771515b7d939bca142b29c20c2376bc6111"},
-    {file = "Automat-20.2.0.tar.gz", hash = "sha256:7979803c74610e11ef0c0d68a2942b152df52da55336e0c9d58daf1831cbdf33"},
+    {file = "Automat-22.10.0-py2.py3-none-any.whl", hash = "sha256:c3164f8742b9dc440f3682482d32aaff7bb53f71740dd018533f9de286b64180"},
+    {file = "Automat-22.10.0.tar.gz", hash = "sha256:e56beb84edad19dcc11d30e8d9b895f75deeb5ef5e96b84a467066b3b84bb04e"},
 ]
 bcrypt = [
     {file = "bcrypt-4.0.1-cp36-abi3-macosx_10_10_universal2.whl", hash = "sha256:b1023030aec778185a6c16cf70f359cbb6e0c289fd564a7cfa29e727a1c38f8f"},
@@ -2251,41 +2255,64 @@ phonenumbers = [
     {file = "phonenumbers-8.12.56.tar.gz", hash = "sha256:82a4f226c930d02dcdf6d4b29e4cfd8678991fe65c2efd5fdd143557186f0868"},
 ]
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     {file = "xmlschema-1.10.0-py3-none-any.whl", hash = "sha256:dbd68bded2fef00c19cf37110ca0565eca34cf0b6c9e1d3b62ad0de8cbb582ca"},
diff --git a/tests/federation/transport/test_client.py b/tests/federation/transport/test_client.py
index dd4d1b56de..b84c74fc0e 100644
--- a/tests/federation/transport/test_client.py
+++ b/tests/federation/transport/test_client.py
@@ -15,6 +15,8 @@
 import json
 from unittest.mock import Mock
 
+import ijson.common
+
 from synapse.api.room_versions import RoomVersions
 from synapse.federation.transport.client import SendJoinParser
 from synapse.util import ExceptionBundle
@@ -117,8 +119,17 @@ class SendJoinParserTestCase(TestCase):
         coro_3 = Mock()
         coro_3.close = Mock(side_effect=RuntimeError("Couldn't close coro 3"))
 
+        original_coros = parser._coros
         parser._coros = [coro_1, coro_2, coro_3]
 
+        # Close the original coroutines. If we don't, when we garbage collect them
+        # they will throw, failing the test. (Oddly, this only started in CPython 3.11).
+        for coro in original_coros:
+            try:
+                coro.close()
+            except ijson.common.IncompleteJSONError:
+                pass
+
         # Send half of the data to the parser
         parser.write(serialisation[: len(serialisation) // 2])