From ff42b6c53cd1b9991de687e79b7f989daf5e5984 Mon Sep 17 00:00:00 2001
From: Steven Silvester <steve.silvester@mongodb.com>
Date: Tue, 29 Jul 2025 14:09:31 -0500
Subject: [PATCH 01/19] wip

---
 .evergreen/config.yml               |  4 ++--
 .github/workflows/test-python.yml   |  4 ++--
 bindings/python/.evergreen/test.sh  | 19 +++++++++------
 bindings/python/.evergreen/utils.sh | 36 ++++++++++++-----------------
 bindings/python/pyproject.toml      |  5 ++--
 bindings/python/requirements.txt    |  2 +-
 6 files changed, 34 insertions(+), 36 deletions(-)

diff --git a/.evergreen/config.yml b/.evergreen/config.yml
index 44ab23faa..d92e8e7a1 100755
--- a/.evergreen/config.yml
+++ b/.evergreen/config.yml
@@ -563,7 +563,7 @@ tasks:
   commands:
     - func: "fetch source"
     - func: "build python release"
-      vars: { PYTHON: /opt/python/3.8/bin/python3 }
+      vars: { PYTHON: /opt/python/3.10/bin/python3 }
     - func: "upload python release"
 
 - name: "release-python-windows"
@@ -572,7 +572,7 @@ tasks:
   commands:
     - func: "fetch source"
     - func: "build python release"
-      vars: { PYTHON: C:/python/Python38/python.exe }
+      vars: { PYTHON: C:/python/Python310/python.exe }
     - func: "upload python release"
 
 - name: "release-python-combine"
diff --git a/.github/workflows/test-python.yml b/.github/workflows/test-python.yml
index b818692be..8e5c3661c 100644
--- a/.github/workflows/test-python.yml
+++ b/.github/workflows/test-python.yml
@@ -43,7 +43,7 @@ jobs:
       fail-fast: false
       matrix:
         os: [ubuntu-latest, windows-latest, macos-latest]
-        python-version: ["3.8", "3.13"]
+        python-version: ["3.10", "3.13", "3.14t"]
 
     steps:
       - uses: actions/checkout@v4
@@ -57,7 +57,7 @@ jobs:
           python-version: ${{ matrix.python-version }}
       - name: Build and test dist files
         run: |
-          if [ "${{ matrix.python-version }}" == "3.13" ]; then 
+          if [ "${{ matrix.python-version }}" == "3.14" ]; then 
             export PIP_PRE=1
           fi
           export LIBMONGOCRYPT_VERSION=$(cat ./scripts/libmongocrypt-version.txt)
diff --git a/bindings/python/.evergreen/test.sh b/bindings/python/.evergreen/test.sh
index e49577c6f..ab3361a57 100755
--- a/bindings/python/.evergreen/test.sh
+++ b/bindings/python/.evergreen/test.sh
@@ -18,11 +18,13 @@ if [ "Windows_NT" = "$OS" ]; then # Magic variable in cygwin
     PYMONGOCRYPT_LIB=${MONGOCRYPT_DIR}/nocrypto/bin/mongocrypt.dll
     PYMONGOCRYPT_LIB_CRYPTO=$(cygpath -m ${MONGOCRYPT_DIR}/bin/mongocrypt.dll)
     export PYMONGOCRYPT_LIB=$(cygpath -m $PYMONGOCRYPT_LIB)
-    PYTHONS=("C:/python/Python38/python.exe"
-             "C:/python/Python39/python.exe"
+    PYTHONS=("C:/python/Python39/python.exe"
              "C:/python/Python310/python.exe"
              "C:/python/Python311/python.exe"
-             "C:/python/Python312/python.exe")
+             "C:/python/Python312/python.exe"
+             "C:/python/Python313/python.exe"
+             "C:/python/Python314/python.exe"
+             "C:/python/Python314/python3.14t.exe")
     export CRYPT_SHARED_PATH=../crypt_shared/bin/mongo_crypt_v1.dll
     C:/python/Python310/python.exe drivers-evergreen-tools/.evergreen/mongodl.py --component crypt_shared \
       --version latest --out ../crypt_shared/
@@ -30,10 +32,12 @@ elif [ "Darwin" = "$(uname -s)" ]; then
     export PYMONGOCRYPT_LIB=${MONGOCRYPT_DIR}/nocrypto/lib/libmongocrypt.dylib
     PYMONGOCRYPT_LIB_CRYPTO=${MONGOCRYPT_DIR}/lib/libmongocrypt.dylib
     PYTHONS=(
-          "/Library/Frameworks/Python.framework/Versions/3.9/bin/python3"
           "/Library/Frameworks/Python.framework/Versions/3.10/bin/python3"
           "/Library/Frameworks/Python.framework/Versions/3.11/bin/python3"
           "/Library/Frameworks/Python.framework/Versions/3.12/bin/python3"
+          "/Library/Frameworks/Python.framework/Versions/3.13/bin/python3"
+          "/Library/Frameworks/Python.framework/Versions/3.14/bin/python3"
+          "/Library/Frameworks/PythonT.framework/Versions/3.14/bin/python3"
           )
 
     export CRYPT_SHARED_PATH="../crypt_shared/lib/mongo_crypt_v1.dylib"
@@ -55,12 +59,13 @@ else
           "/opt/mongodbtoolchain/v4/bin/python3"
         )
     else
-        PYTHONS=("/opt/python/3.8/bin/python3"
-          "/opt/python/3.9/bin/python3"
+        PYTHONS=(
           "/opt/python/3.10/bin/python3"
           "/opt/python/3.11/bin/python3"
           "/opt/python/3.12/bin/python3"
           "/opt/python/3.13/bin/python3"
+          "/opt/python/3.14/bin/python3"
+          "/opt/python/3.14t/bin/python3"
         )
     fi
     /opt/mongodbtoolchain/v3/bin/python3 drivers-evergreen-tools/.evergreen/mongodl.py --component \
@@ -72,7 +77,7 @@ for PYTHON_BINARY in "${PYTHONS[@]}"; do
     $PYTHON_BINARY -c 'import sys; print(sys.version)'
     git clean -dffx
     createvirtualenv $PYTHON_BINARY .venv
-    python -m pip install --prefer-binary -v -e ".[test]"
+    python -m pip install --prefer-binary -v -e ".[test]" || python -m pip install --pre --prefer-binary -v -e ".[test]"
     echo "Running tests with crypto enabled libmongocrypt..."
     PYMONGOCRYPT_LIB=$PYMONGOCRYPT_LIB_CRYPTO python -c 'from pymongocrypt.binding import lib;assert lib.mongocrypt_is_crypto_available(), "mongocrypt_is_crypto_available() returned False"'
     PYMONGOCRYPT_LIB=$PYMONGOCRYPT_LIB_CRYPTO python -m pytest -v --ignore=test/performance .
diff --git a/bindings/python/.evergreen/utils.sh b/bindings/python/.evergreen/utils.sh
index 57055fb1e..3d5c078f2 100755
--- a/bindings/python/.evergreen/utils.sh
+++ b/bindings/python/.evergreen/utils.sh
@@ -36,47 +36,41 @@ createvirtualenv () {
 # PYTHON = find_python3
 find_python3() {
     PYTHON=""
-    # Add a fallback system python3 if it is available and Python 3.8+.
-    if is_python_38 "$(command -v python3)"; then
+    # Add a fallback system python3 if it is available and Python 3.10+.
+    if is_python_310 "$(command -v python3)"; then
         PYTHON="$(command -v python3)"
     fi
     # Find a suitable toolchain version, if available.
     if [ "$(uname -s)" = "Darwin" ]; then
-        # macos 11.00
-        if [ -d "/Library/Frameworks/Python.Framework/Versions/3.10" ]; then
-            PYTHON="/Library/Frameworks/Python.Framework/Versions/3.10/bin/python3"
-        # macos 10.14
-        elif [ -d "/Library/Frameworks/Python.Framework/Versions/3.8" ]; then
-            PYTHON="/Library/Frameworks/Python.Framework/Versions/3.8/bin/python3"
-        fi
+        PYTHON="/Library/Frameworks/Python.Framework/Versions/3.10/bin/python3"
     elif [ "Windows_NT" = "${OS:-}" ]; then # Magic variable in cygwin
-        PYTHON="C:/python/Python38/python.exe"
+        PYTHON="C:/python/Python310/python.exe"
     else
-        # Prefer our own toolchain, fall back to mongodb toolchain if it has Python 3.8+.
-        if [ -f "/opt/python/3.8/bin/python3" ]; then
-            PYTHON="/opt/python/3.8/bin/python3"
-        elif is_python_38 "$(command -v /opt/mongodbtoolchain/v4/bin/python3)"; then
+        # Prefer our own toolchain, fall back to mongodb toolchain if it has Python 3.10+.
+        if [ -f "/opt/python/3.10/bin/python3" ]; then
+            PYTHON="/opt/python/3.10/bin/python3"
+        elif is_python_310 "$(command -v /opt/mongodbtoolchain/v4/bin/python3)"; then
             PYTHON="/opt/mongodbtoolchain/v4/bin/python3"
-        elif is_python_38 "$(command -v /opt/mongodbtoolchain/v3/bin/python3)"; then
+        elif is_python_310 "$(command -v /opt/mongodbtoolchain/v3/bin/python3)"; then
             PYTHON="/opt/mongodbtoolchain/v3/bin/python3"
         fi
     fi
     if [ -z "$PYTHON" ]; then
-        echo "Cannot run pre-commit without python3.8+ installed!"
+        echo "Cannot run pre-commit without python3.10+ installed!"
         exit 1
     fi
     echo "$PYTHON"
 }
 
-# Function that returns success if the provided Python binary is version 3.8 or later
+# Function that returns success if the provided Python binary is version 3.10 or later
 # Usage:
-# is_python_38 /path/to/python
+# is_python_310 /path/to/python
 # * param1: Python binary
-is_python_38() {
+is_python_310() {
     if [ -z "$1" ]; then
         return 1
-    elif $1 -c "import sys; exit(sys.version_info[:2] < (3, 8))"; then
-        # runs when sys.version_info[:2] >= (3, 8)
+    elif $1 -c "import sys; exit(sys.version_info[:2] < (3, 10))"; then
+        # runs when sys.version_info[:2] >= (3, 10)
         return 0
     else
         return 1
diff --git a/bindings/python/pyproject.toml b/bindings/python/pyproject.toml
index f69cf3c57..5c83f6dfc 100644
--- a/bindings/python/pyproject.toml
+++ b/bindings/python/pyproject.toml
@@ -8,7 +8,7 @@ dynamic = ["version", "dependencies", "optional-dependencies"]
 description = "Python bindings for libmongocrypt"
 readme = "README.rst"
 license = {file="LICENSE"}
-requires-python = ">=3.8"
+requires-python = ">=3.10"
 authors = [
     { name = "Shane Harvey", email = "mongodb-user@googlegroups.com" },
 ]
@@ -29,14 +29,13 @@ classifiers = [
     "Operating System :: POSIX",
     "Programming Language :: Python :: 3",
     "Programming Language :: Python :: 3 :: Only",
-    "Programming Language :: Python :: 3.8",
-    "Programming Language :: Python :: 3.9",
     "Programming Language :: Python :: Implementation :: CPython",
     "Programming Language :: Python :: Implementation :: PyPy",
     "Programming Language :: Python :: 3.10",
     "Programming Language :: Python :: 3.11",
     "Programming Language :: Python :: 3.12",
     "Programming Language :: Python :: 3.13",
+    "Programming Language :: Python :: 3.14",
     "Topic :: Database",
 ]
 
diff --git a/bindings/python/requirements.txt b/bindings/python/requirements.txt
index f95140da6..3440d1ddf 100644
--- a/bindings/python/requirements.txt
+++ b/bindings/python/requirements.txt
@@ -1,4 +1,4 @@
-cffi>=1.12.0,<2
+cffi>=1.12.0,<3;python_version<"3.14"
 cryptography>=40
 packaging>=21.0
 httpx>=0.25.0

From f32a8ebeb0b86f5c4395171267df4b16fe98f87b Mon Sep 17 00:00:00 2001
From: Steven Silvester <steve.silvester@mongodb.com>
Date: Tue, 29 Jul 2025 14:13:35 -0500
Subject: [PATCH 02/19] run workflows

---
 .github/workflows/dist-python.yml | 2 +-
 .github/workflows/test-python.yml | 4 ++--
 2 files changed, 3 insertions(+), 3 deletions(-)

diff --git a/.github/workflows/dist-python.yml b/.github/workflows/dist-python.yml
index b25b84c18..95c64e968 100644
--- a/.github/workflows/dist-python.yml
+++ b/.github/workflows/dist-python.yml
@@ -30,7 +30,7 @@ defaults:
 
 jobs:
   build_dist:
-    if: github.repository_owner == 'mongodb' || (github.event_name == 'workflow_dispatch' || github.event_name == 'workflow_call')
+    if: github.repository_owner == 'blink1073' || (github.event_name == 'workflow_dispatch' || github.event_name == 'workflow_call')
     runs-on: ${{ matrix.os }}
     strategy:
       matrix:
diff --git a/.github/workflows/test-python.yml b/.github/workflows/test-python.yml
index 8e5c3661c..a33271f76 100644
--- a/.github/workflows/test-python.yml
+++ b/.github/workflows/test-python.yml
@@ -20,7 +20,7 @@ defaults:
 jobs:
 
   static:
-    if: github.repository_owner == 'mongodb'
+    if: github.repository_owner == 'blink1073'
     runs-on: ubuntu-latest
     steps:
      - uses: actions/checkout@v4
@@ -37,7 +37,7 @@ jobs:
         check-manifest -v
 
   build:
-    if: github.repository_owner == 'mongodb'
+    if: github.repository_owner == 'blink1073'
     runs-on: ${{ matrix.os }}
     strategy:
       fail-fast: false

From f1387267cec36e80bfb27c23be4f75d5bd16cdb1 Mon Sep 17 00:00:00 2001
From: Steven Silvester <steve.silvester@mongodb.com>
Date: Tue, 29 Jul 2025 18:23:07 -0500
Subject: [PATCH 03/19] fixup test

---
 .github/workflows/test-python.yml  | 3 ---
 bindings/python/.evergreen/test.sh | 2 +-
 bindings/python/requirements.txt   | 1 +
 3 files changed, 2 insertions(+), 4 deletions(-)

diff --git a/.github/workflows/test-python.yml b/.github/workflows/test-python.yml
index a33271f76..a44853fdf 100644
--- a/.github/workflows/test-python.yml
+++ b/.github/workflows/test-python.yml
@@ -57,9 +57,6 @@ jobs:
           python-version: ${{ matrix.python-version }}
       - name: Build and test dist files
         run: |
-          if [ "${{ matrix.python-version }}" == "3.14" ]; then 
-            export PIP_PRE=1
-          fi
           export LIBMONGOCRYPT_VERSION=$(cat ./scripts/libmongocrypt-version.txt)
           git fetch origin $LIBMONGOCRYPT_VERSION
           bash ./scripts/release.sh
diff --git a/bindings/python/.evergreen/test.sh b/bindings/python/.evergreen/test.sh
index ab3361a57..65f548e93 100755
--- a/bindings/python/.evergreen/test.sh
+++ b/bindings/python/.evergreen/test.sh
@@ -77,7 +77,7 @@ for PYTHON_BINARY in "${PYTHONS[@]}"; do
     $PYTHON_BINARY -c 'import sys; print(sys.version)'
     git clean -dffx
     createvirtualenv $PYTHON_BINARY .venv
-    python -m pip install --prefer-binary -v -e ".[test]" || python -m pip install --pre --prefer-binary -v -e ".[test]"
+    python -m pip install --prefer-binary -v -e ".[test]"
     echo "Running tests with crypto enabled libmongocrypt..."
     PYMONGOCRYPT_LIB=$PYMONGOCRYPT_LIB_CRYPTO python -c 'from pymongocrypt.binding import lib;assert lib.mongocrypt_is_crypto_available(), "mongocrypt_is_crypto_available() returned False"'
     PYMONGOCRYPT_LIB=$PYMONGOCRYPT_LIB_CRYPTO python -m pytest -v --ignore=test/performance .
diff --git a/bindings/python/requirements.txt b/bindings/python/requirements.txt
index 3440d1ddf..51ce01e3d 100644
--- a/bindings/python/requirements.txt
+++ b/bindings/python/requirements.txt
@@ -1,4 +1,5 @@
 cffi>=1.12.0,<3;python_version<"3.14"
+cffi>=2.0.0b3,<3;python_version=="3.14"
 cryptography>=40
 packaging>=21.0
 httpx>=0.25.0

From f6cf56db2d19fb885b58015b640c42e9e3faba3a Mon Sep 17 00:00:00 2001
From: Steven Silvester <steve.silvester@mongodb.com>
Date: Tue, 29 Jul 2025 18:41:26 -0500
Subject: [PATCH 04/19] fixup

---
 .github/workflows/dist-python.yml | 2 +-
 bindings/python/requirements.txt  | 2 +-
 2 files changed, 2 insertions(+), 2 deletions(-)

diff --git a/.github/workflows/dist-python.yml b/.github/workflows/dist-python.yml
index 95c64e968..96536c847 100644
--- a/.github/workflows/dist-python.yml
+++ b/.github/workflows/dist-python.yml
@@ -47,7 +47,7 @@ jobs:
 
       - uses: actions/setup-python@v5
         with:
-          python-version: 3.8
+          python-version: "3.10"
           cache: 'pip'
           cache-dependency-path: 'bindings/python/pyproject.toml'
           allow-prereleases: true
diff --git a/bindings/python/requirements.txt b/bindings/python/requirements.txt
index 51ce01e3d..507493e57 100644
--- a/bindings/python/requirements.txt
+++ b/bindings/python/requirements.txt
@@ -1,5 +1,5 @@
 cffi>=1.12.0,<3;python_version<"3.14"
-cffi>=2.0.0b3,<3;python_version=="3.14"
+cffi>=2.0.0b1,<3;python_version=="3.14"
 cryptography>=40
 packaging>=21.0
 httpx>=0.25.0

From 24b8aee69d99ba5b50bef97d79ada731daf8384f Mon Sep 17 00:00:00 2001
From: Steven Silvester <steve.silvester@mongodb.com>
Date: Tue, 29 Jul 2025 18:46:59 -0500
Subject: [PATCH 05/19] drop 3.14t for now

---
 .github/workflows/test-python.yml  | 2 +-
 bindings/python/.evergreen/test.sh | 5 +----
 2 files changed, 2 insertions(+), 5 deletions(-)

diff --git a/.github/workflows/test-python.yml b/.github/workflows/test-python.yml
index a44853fdf..5f0322f67 100644
--- a/.github/workflows/test-python.yml
+++ b/.github/workflows/test-python.yml
@@ -43,7 +43,7 @@ jobs:
       fail-fast: false
       matrix:
         os: [ubuntu-latest, windows-latest, macos-latest]
-        python-version: ["3.10", "3.13", "3.14t"]
+        python-version: ["3.10", "3.13", "3.14"]
 
     steps:
       - uses: actions/checkout@v4
diff --git a/bindings/python/.evergreen/test.sh b/bindings/python/.evergreen/test.sh
index 65f548e93..fe17d95b8 100755
--- a/bindings/python/.evergreen/test.sh
+++ b/bindings/python/.evergreen/test.sh
@@ -23,8 +23,7 @@ if [ "Windows_NT" = "$OS" ]; then # Magic variable in cygwin
              "C:/python/Python311/python.exe"
              "C:/python/Python312/python.exe"
              "C:/python/Python313/python.exe"
-             "C:/python/Python314/python.exe"
-             "C:/python/Python314/python3.14t.exe")
+             "C:/python/Python314/python.exe")
     export CRYPT_SHARED_PATH=../crypt_shared/bin/mongo_crypt_v1.dll
     C:/python/Python310/python.exe drivers-evergreen-tools/.evergreen/mongodl.py --component crypt_shared \
       --version latest --out ../crypt_shared/
@@ -37,7 +36,6 @@ elif [ "Darwin" = "$(uname -s)" ]; then
           "/Library/Frameworks/Python.framework/Versions/3.12/bin/python3"
           "/Library/Frameworks/Python.framework/Versions/3.13/bin/python3"
           "/Library/Frameworks/Python.framework/Versions/3.14/bin/python3"
-          "/Library/Frameworks/PythonT.framework/Versions/3.14/bin/python3"
           )
 
     export CRYPT_SHARED_PATH="../crypt_shared/lib/mongo_crypt_v1.dylib"
@@ -65,7 +63,6 @@ else
           "/opt/python/3.12/bin/python3"
           "/opt/python/3.13/bin/python3"
           "/opt/python/3.14/bin/python3"
-          "/opt/python/3.14t/bin/python3"
         )
     fi
     /opt/mongodbtoolchain/v3/bin/python3 drivers-evergreen-tools/.evergreen/mongodl.py --component \

From 5f1b8552cd0619a83cbb13e26fd65167fd740aa6 Mon Sep 17 00:00:00 2001
From: Steven Silvester <steve.silvester@mongodb.com>
Date: Tue, 29 Jul 2025 18:51:23 -0500
Subject: [PATCH 06/19] lint

---
 bindings/python/pymongocrypt/mongocrypt.py    | 2 +-
 bindings/python/pymongocrypt/options.py       | 6 +++---
 bindings/python/test/performance/perf_test.py | 3 +--
 3 files changed, 5 insertions(+), 6 deletions(-)

diff --git a/bindings/python/pymongocrypt/mongocrypt.py b/bindings/python/pymongocrypt/mongocrypt.py
index 608d39e32..46520b6f9 100644
--- a/bindings/python/pymongocrypt/mongocrypt.py
+++ b/bindings/python/pymongocrypt/mongocrypt.py
@@ -52,7 +52,7 @@ def __init__(self, options, callback):
         if not isinstance(options, MongoCryptOptions):
             raise TypeError("options must be a MongoCryptOptions")
 
-        if not isinstance(callback, (AsyncMongoCryptCallback, MongoCryptCallback)):
+        if not isinstance(callback, AsyncMongoCryptCallback | MongoCryptCallback):
             raise TypeError(
                 "callback must be a MongoCryptCallback or AsyncMongoCryptCallback"
             )
diff --git a/bindings/python/pymongocrypt/options.py b/bindings/python/pymongocrypt/options.py
index c1e27b1d5..a709ed3e5 100644
--- a/bindings/python/pymongocrypt/options.py
+++ b/bindings/python/pymongocrypt/options.py
@@ -114,7 +114,7 @@ def __init__(
                             f"kms_providers[{name!r}] must contain "
                             "'email' and 'privateKey'"
                         )
-                    if not isinstance(provider["privateKey"], (bytes, unicode_type)):
+                    if not isinstance(provider["privateKey"], bytes | unicode_type):
                         raise TypeError(
                             f"kms_providers[{name!r}]['privateKey'] must "
                             "be an instance of bytes or str"
@@ -122,7 +122,7 @@ def __init__(
             elif provider_type == "kmip":
                 if "endpoint" not in provider:
                     raise ValueError(f"kms_providers[{name!r}] must contain 'endpoint'")
-                if not isinstance(provider["endpoint"], (str, unicode_type)):
+                if not isinstance(provider["endpoint"], str | unicode_type):
                     raise TypeError(
                         f"kms_providers[{name!r}]['endpoint'] must "
                         "be an instance of str"
@@ -130,7 +130,7 @@ def __init__(
             elif provider_type == "local":
                 if "key" not in provider:
                     raise ValueError(f"kms_providers[{name!r}] must contain 'key'")
-                if not isinstance(provider["key"], (bytes, unicode_type)):
+                if not isinstance(provider["key"], bytes | unicode_type):
                     raise TypeError(
                         f"kms_providers[{name!r}]['key'] must be an "
                         "instance of bytes or str"
diff --git a/bindings/python/test/performance/perf_test.py b/bindings/python/test/performance/perf_test.py
index 2d66063d7..8a11a7c3a 100644
--- a/bindings/python/test/performance/perf_test.py
+++ b/bindings/python/test/performance/perf_test.py
@@ -20,7 +20,6 @@
 import time
 import unittest
 from concurrent.futures import ThreadPoolExecutor
-from typing import List
 
 try:
     import simplejson as json
@@ -52,7 +51,7 @@
 
 OUTPUT_FILE = os.environ.get("OUTPUT_FILE")
 
-result_data: List = []
+result_data: list = []
 
 
 def read(filename, **kwargs):

From d335cf62446a9efb1468b49c6240b8b91bcd947b Mon Sep 17 00:00:00 2001
From: Steven Silvester <steve.silvester@mongodb.com>
Date: Tue, 29 Jul 2025 19:02:25 -0500
Subject: [PATCH 07/19] restore 3.9 support

---
 .github/workflows/dist-python.yml   |  2 +-
 .github/workflows/test-python.yml   |  2 +-
 bindings/python/.evergreen/test.sh  |  2 ++
 bindings/python/.evergreen/utils.sh | 24 ++++++++++++------------
 bindings/python/pyproject.toml      |  3 ++-
 5 files changed, 18 insertions(+), 15 deletions(-)

diff --git a/.github/workflows/dist-python.yml b/.github/workflows/dist-python.yml
index 96536c847..325b64e03 100644
--- a/.github/workflows/dist-python.yml
+++ b/.github/workflows/dist-python.yml
@@ -47,7 +47,7 @@ jobs:
 
       - uses: actions/setup-python@v5
         with:
-          python-version: "3.10"
+          python-version: "3.9"
           cache: 'pip'
           cache-dependency-path: 'bindings/python/pyproject.toml'
           allow-prereleases: true
diff --git a/.github/workflows/test-python.yml b/.github/workflows/test-python.yml
index 5f0322f67..8f9b589ed 100644
--- a/.github/workflows/test-python.yml
+++ b/.github/workflows/test-python.yml
@@ -43,7 +43,7 @@ jobs:
       fail-fast: false
       matrix:
         os: [ubuntu-latest, windows-latest, macos-latest]
-        python-version: ["3.10", "3.13", "3.14"]
+        python-version: ["3.9", "3.13", "3.14"]
 
     steps:
       - uses: actions/checkout@v4
diff --git a/bindings/python/.evergreen/test.sh b/bindings/python/.evergreen/test.sh
index fe17d95b8..5295c73e6 100755
--- a/bindings/python/.evergreen/test.sh
+++ b/bindings/python/.evergreen/test.sh
@@ -31,6 +31,7 @@ elif [ "Darwin" = "$(uname -s)" ]; then
     export PYMONGOCRYPT_LIB=${MONGOCRYPT_DIR}/nocrypto/lib/libmongocrypt.dylib
     PYMONGOCRYPT_LIB_CRYPTO=${MONGOCRYPT_DIR}/lib/libmongocrypt.dylib
     PYTHONS=(
+          "/Library/Frameworks/Python.framework/Versions/3.9/bin/python3"
           "/Library/Frameworks/Python.framework/Versions/3.10/bin/python3"
           "/Library/Frameworks/Python.framework/Versions/3.11/bin/python3"
           "/Library/Frameworks/Python.framework/Versions/3.12/bin/python3"
@@ -58,6 +59,7 @@ else
         )
     else
         PYTHONS=(
+          "/opt/python/3.9/bin/python3"
           "/opt/python/3.10/bin/python3"
           "/opt/python/3.11/bin/python3"
           "/opt/python/3.12/bin/python3"
diff --git a/bindings/python/.evergreen/utils.sh b/bindings/python/.evergreen/utils.sh
index 3d5c078f2..e2d3923d5 100755
--- a/bindings/python/.evergreen/utils.sh
+++ b/bindings/python/.evergreen/utils.sh
@@ -36,37 +36,37 @@ createvirtualenv () {
 # PYTHON = find_python3
 find_python3() {
     PYTHON=""
-    # Add a fallback system python3 if it is available and Python 3.10+.
-    if is_python_310 "$(command -v python3)"; then
+    # Add a fallback system python3 if it is available and Python 3.9+.
+    if is_python_39 "$(command -v python3)"; then
         PYTHON="$(command -v python3)"
     fi
     # Find a suitable toolchain version, if available.
     if [ "$(uname -s)" = "Darwin" ]; then
-        PYTHON="/Library/Frameworks/Python.Framework/Versions/3.10/bin/python3"
+        PYTHON="/Library/Frameworks/Python.Framework/Versions/3.9/bin/python3"
     elif [ "Windows_NT" = "${OS:-}" ]; then # Magic variable in cygwin
         PYTHON="C:/python/Python310/python.exe"
     else
-        # Prefer our own toolchain, fall back to mongodb toolchain if it has Python 3.10+.
-        if [ -f "/opt/python/3.10/bin/python3" ]; then
-            PYTHON="/opt/python/3.10/bin/python3"
-        elif is_python_310 "$(command -v /opt/mongodbtoolchain/v4/bin/python3)"; then
+        # Prefer our own toolchain, fall back to mongodb toolchain if it has Python 3.9+.
+        if [ -f "/opt/python/3.9/bin/python3" ]; then
+            PYTHON="/opt/python/3.9/bin/python3"
+        elif is_python_39 "$(command -v /opt/mongodbtoolchain/v4/bin/python3)"; then
             PYTHON="/opt/mongodbtoolchain/v4/bin/python3"
-        elif is_python_310 "$(command -v /opt/mongodbtoolchain/v3/bin/python3)"; then
+        elif is_python_39 "$(command -v /opt/mongodbtoolchain/v3/bin/python3)"; then
             PYTHON="/opt/mongodbtoolchain/v3/bin/python3"
         fi
     fi
     if [ -z "$PYTHON" ]; then
-        echo "Cannot run pre-commit without python3.10+ installed!"
+        echo "Cannot run pre-commit without python3.9+ installed!"
         exit 1
     fi
     echo "$PYTHON"
 }
 
-# Function that returns success if the provided Python binary is version 3.10 or later
+# Function that returns success if the provided Python binary is version 3.9 or later
 # Usage:
-# is_python_310 /path/to/python
+# is_python_39 /path/to/python
 # * param1: Python binary
-is_python_310() {
+is_python_39() {
     if [ -z "$1" ]; then
         return 1
     elif $1 -c "import sys; exit(sys.version_info[:2] < (3, 10))"; then
diff --git a/bindings/python/pyproject.toml b/bindings/python/pyproject.toml
index 5c83f6dfc..5859d13bf 100644
--- a/bindings/python/pyproject.toml
+++ b/bindings/python/pyproject.toml
@@ -8,7 +8,7 @@ dynamic = ["version", "dependencies", "optional-dependencies"]
 description = "Python bindings for libmongocrypt"
 readme = "README.rst"
 license = {file="LICENSE"}
-requires-python = ">=3.10"
+requires-python = ">=3.9"
 authors = [
     { name = "Shane Harvey", email = "mongodb-user@googlegroups.com" },
 ]
@@ -31,6 +31,7 @@ classifiers = [
     "Programming Language :: Python :: 3 :: Only",
     "Programming Language :: Python :: Implementation :: CPython",
     "Programming Language :: Python :: Implementation :: PyPy",
+    "Programming Language :: Python :: 3.9",
     "Programming Language :: Python :: 3.10",
     "Programming Language :: Python :: 3.11",
     "Programming Language :: Python :: 3.12",

From 2e2376763fe69290186863622aab0e5233aa35fa Mon Sep 17 00:00:00 2001
From: Steven Silvester <steve.silvester@mongodb.com>
Date: Tue, 29 Jul 2025 19:07:52 -0500
Subject: [PATCH 08/19] fix up 3.14 support

---
 .github/workflows/test-python.yml  | 5 ++++-
 bindings/python/.evergreen/test.sh | 2 +-
 bindings/python/requirements.txt   | 3 +--
 3 files changed, 6 insertions(+), 4 deletions(-)

diff --git a/.github/workflows/test-python.yml b/.github/workflows/test-python.yml
index 8f9b589ed..0493e3106 100644
--- a/.github/workflows/test-python.yml
+++ b/.github/workflows/test-python.yml
@@ -43,7 +43,7 @@ jobs:
       fail-fast: false
       matrix:
         os: [ubuntu-latest, windows-latest, macos-latest]
-        python-version: ["3.9", "3.13", "3.14"]
+        python-version: ["3.9", "3.13", "3.14t"]
 
     steps:
       - uses: actions/checkout@v4
@@ -57,6 +57,9 @@ jobs:
           python-version: ${{ matrix.python-version }}
       - name: Build and test dist files
         run: |
+          if [ "${{ matrix.python-version }}" == "3.14" ]; then 
+            export PIP_PRE=1
+          fi
           export LIBMONGOCRYPT_VERSION=$(cat ./scripts/libmongocrypt-version.txt)
           git fetch origin $LIBMONGOCRYPT_VERSION
           bash ./scripts/release.sh
diff --git a/bindings/python/.evergreen/test.sh b/bindings/python/.evergreen/test.sh
index 5295c73e6..0c2f56dca 100755
--- a/bindings/python/.evergreen/test.sh
+++ b/bindings/python/.evergreen/test.sh
@@ -76,7 +76,7 @@ for PYTHON_BINARY in "${PYTHONS[@]}"; do
     $PYTHON_BINARY -c 'import sys; print(sys.version)'
     git clean -dffx
     createvirtualenv $PYTHON_BINARY .venv
-    python -m pip install --prefer-binary -v -e ".[test]"
+    python -m pip install --prefer-binary -v -e ".[test]" || python -m pip install --pre --prefer-binary -v -e ".[test]"
     echo "Running tests with crypto enabled libmongocrypt..."
     PYMONGOCRYPT_LIB=$PYMONGOCRYPT_LIB_CRYPTO python -c 'from pymongocrypt.binding import lib;assert lib.mongocrypt_is_crypto_available(), "mongocrypt_is_crypto_available() returned False"'
     PYMONGOCRYPT_LIB=$PYMONGOCRYPT_LIB_CRYPTO python -m pytest -v --ignore=test/performance .
diff --git a/bindings/python/requirements.txt b/bindings/python/requirements.txt
index 507493e57..c64bcb573 100644
--- a/bindings/python/requirements.txt
+++ b/bindings/python/requirements.txt
@@ -1,5 +1,4 @@
-cffi>=1.12.0,<3;python_version<"3.14"
-cffi>=2.0.0b1,<3;python_version=="3.14"
+cffi>=1.12.0,<3
 cryptography>=40
 packaging>=21.0
 httpx>=0.25.0

From ab4617e75ece95ede895cc2476a14ea06e40ad77 Mon Sep 17 00:00:00 2001
From: Steven Silvester <steve.silvester@mongodb.com>
Date: Tue, 29 Jul 2025 19:12:40 -0500
Subject: [PATCH 09/19] fix up 3.14 support

---
 .github/workflows/test-python.yml | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/.github/workflows/test-python.yml b/.github/workflows/test-python.yml
index 0493e3106..bdce36520 100644
--- a/.github/workflows/test-python.yml
+++ b/.github/workflows/test-python.yml
@@ -43,7 +43,7 @@ jobs:
       fail-fast: false
       matrix:
         os: [ubuntu-latest, windows-latest, macos-latest]
-        python-version: ["3.9", "3.13", "3.14t"]
+        python-version: ["3.9", "3.13", "3.14"]
 
     steps:
       - uses: actions/checkout@v4

From fcd004685d7a668410bc0aca0842b5e4b1c32cfd Mon Sep 17 00:00:00 2001
From: Steven Silvester <steve.silvester@mongodb.com>
Date: Wed, 30 Jul 2025 06:16:27 -0500
Subject: [PATCH 10/19] Revert "lint"

This reverts commit 5f1b8552cd0619a83cbb13e26fd65167fd740aa6.
---
 bindings/python/pymongocrypt/mongocrypt.py    | 2 +-
 bindings/python/pymongocrypt/options.py       | 6 +++---
 bindings/python/test/performance/perf_test.py | 3 ++-
 3 files changed, 6 insertions(+), 5 deletions(-)

diff --git a/bindings/python/pymongocrypt/mongocrypt.py b/bindings/python/pymongocrypt/mongocrypt.py
index 46520b6f9..608d39e32 100644
--- a/bindings/python/pymongocrypt/mongocrypt.py
+++ b/bindings/python/pymongocrypt/mongocrypt.py
@@ -52,7 +52,7 @@ def __init__(self, options, callback):
         if not isinstance(options, MongoCryptOptions):
             raise TypeError("options must be a MongoCryptOptions")
 
-        if not isinstance(callback, AsyncMongoCryptCallback | MongoCryptCallback):
+        if not isinstance(callback, (AsyncMongoCryptCallback, MongoCryptCallback)):
             raise TypeError(
                 "callback must be a MongoCryptCallback or AsyncMongoCryptCallback"
             )
diff --git a/bindings/python/pymongocrypt/options.py b/bindings/python/pymongocrypt/options.py
index a709ed3e5..c1e27b1d5 100644
--- a/bindings/python/pymongocrypt/options.py
+++ b/bindings/python/pymongocrypt/options.py
@@ -114,7 +114,7 @@ def __init__(
                             f"kms_providers[{name!r}] must contain "
                             "'email' and 'privateKey'"
                         )
-                    if not isinstance(provider["privateKey"], bytes | unicode_type):
+                    if not isinstance(provider["privateKey"], (bytes, unicode_type)):
                         raise TypeError(
                             f"kms_providers[{name!r}]['privateKey'] must "
                             "be an instance of bytes or str"
@@ -122,7 +122,7 @@ def __init__(
             elif provider_type == "kmip":
                 if "endpoint" not in provider:
                     raise ValueError(f"kms_providers[{name!r}] must contain 'endpoint'")
-                if not isinstance(provider["endpoint"], str | unicode_type):
+                if not isinstance(provider["endpoint"], (str, unicode_type)):
                     raise TypeError(
                         f"kms_providers[{name!r}]['endpoint'] must "
                         "be an instance of str"
@@ -130,7 +130,7 @@ def __init__(
             elif provider_type == "local":
                 if "key" not in provider:
                     raise ValueError(f"kms_providers[{name!r}] must contain 'key'")
-                if not isinstance(provider["key"], bytes | unicode_type):
+                if not isinstance(provider["key"], (bytes, unicode_type)):
                     raise TypeError(
                         f"kms_providers[{name!r}]['key'] must be an "
                         "instance of bytes or str"
diff --git a/bindings/python/test/performance/perf_test.py b/bindings/python/test/performance/perf_test.py
index 8a11a7c3a..2d66063d7 100644
--- a/bindings/python/test/performance/perf_test.py
+++ b/bindings/python/test/performance/perf_test.py
@@ -20,6 +20,7 @@
 import time
 import unittest
 from concurrent.futures import ThreadPoolExecutor
+from typing import List
 
 try:
     import simplejson as json
@@ -51,7 +52,7 @@
 
 OUTPUT_FILE = os.environ.get("OUTPUT_FILE")
 
-result_data: list = []
+result_data: List = []
 
 
 def read(filename, **kwargs):

From 3fe310dc9adc7b67b8510a5ebcaf154687bac65c Mon Sep 17 00:00:00 2001
From: Steven Silvester <steve.silvester@mongodb.com>
Date: Wed, 30 Jul 2025 06:17:13 -0500
Subject: [PATCH 11/19] fix up 3.9 support

---
 bindings/python/test/performance/perf_test.py | 3 +--
 1 file changed, 1 insertion(+), 2 deletions(-)

diff --git a/bindings/python/test/performance/perf_test.py b/bindings/python/test/performance/perf_test.py
index 2d66063d7..8a11a7c3a 100644
--- a/bindings/python/test/performance/perf_test.py
+++ b/bindings/python/test/performance/perf_test.py
@@ -20,7 +20,6 @@
 import time
 import unittest
 from concurrent.futures import ThreadPoolExecutor
-from typing import List
 
 try:
     import simplejson as json
@@ -52,7 +51,7 @@
 
 OUTPUT_FILE = os.environ.get("OUTPUT_FILE")
 
-result_data: List = []
+result_data: list = []
 
 
 def read(filename, **kwargs):

From 75c925b99934de626b2cc512be1aba5635da1b3c Mon Sep 17 00:00:00 2001
From: Steven Silvester <steve.silvester@mongodb.com>
Date: Wed, 30 Jul 2025 06:58:15 -0500
Subject: [PATCH 12/19] update changelog

---
 bindings/python/CHANGELOG.rst | 6 ++++++
 1 file changed, 6 insertions(+)

diff --git a/bindings/python/CHANGELOG.rst b/bindings/python/CHANGELOG.rst
index e7fb9bf8a..b1349361f 100644
--- a/bindings/python/CHANGELOG.rst
+++ b/bindings/python/CHANGELOG.rst
@@ -1,6 +1,12 @@
 Changelog
 =========
 
+Changes in Version 1.15.0
+-------------------------
+
+- Add support for Python 3.14.
+- Drop support for Python 3.8.
+
 Changes in Version 1.14.1
 -------------------------
 

From 4650bebd695f93778aac7da15aa71ceb353ba6cf Mon Sep 17 00:00:00 2001
From: Steven Silvester <steve.silvester@mongodb.com>
Date: Wed, 30 Jul 2025 06:59:27 -0500
Subject: [PATCH 13/19] update workflows

---
 .github/workflows/dist-python.yml | 2 +-
 .github/workflows/test-python.yml | 4 ++--
 2 files changed, 3 insertions(+), 3 deletions(-)

diff --git a/.github/workflows/dist-python.yml b/.github/workflows/dist-python.yml
index 325b64e03..554c0f357 100644
--- a/.github/workflows/dist-python.yml
+++ b/.github/workflows/dist-python.yml
@@ -30,7 +30,7 @@ defaults:
 
 jobs:
   build_dist:
-    if: github.repository_owner == 'blink1073' || (github.event_name == 'workflow_dispatch' || github.event_name == 'workflow_call')
+    if: github.repository_owner == 'mongodb' || (github.event_name == 'workflow_dispatch' || github.event_name == 'workflow_call')
     runs-on: ${{ matrix.os }}
     strategy:
       matrix:
diff --git a/.github/workflows/test-python.yml b/.github/workflows/test-python.yml
index bdce36520..c4356e7a2 100644
--- a/.github/workflows/test-python.yml
+++ b/.github/workflows/test-python.yml
@@ -20,7 +20,7 @@ defaults:
 jobs:
 
   static:
-    if: github.repository_owner == 'blink1073'
+    if: github.repository_owner == 'mongodb'
     runs-on: ubuntu-latest
     steps:
      - uses: actions/checkout@v4
@@ -37,7 +37,7 @@ jobs:
         check-manifest -v
 
   build:
-    if: github.repository_owner == 'blink1073'
+    if: github.repository_owner == 'mongodb'
     runs-on: ${{ matrix.os }}
     strategy:
       fail-fast: false

From 51a4483ba5b110e0505f28aa374c6a4008518c05 Mon Sep 17 00:00:00 2001
From: Steven Silvester <steve.silvester@mongodb.com>
Date: Wed, 30 Jul 2025 07:01:35 -0500
Subject: [PATCH 14/19] update config.yml

---
 .evergreen/config.yml | 6 +++---
 1 file changed, 3 insertions(+), 3 deletions(-)

diff --git a/.evergreen/config.yml b/.evergreen/config.yml
index d92e8e7a1..fb9b920d5 100755
--- a/.evergreen/config.yml
+++ b/.evergreen/config.yml
@@ -553,7 +553,7 @@ tasks:
   commands:
     - func: "fetch source"
     - func: "build python release"
-      vars: { PYTHON: /Library/Frameworks/Python.framework/Versions/3.10/bin/python3 }
+      vars: { PYTHON: /Library/Frameworks/Python.framework/Versions/3.9/bin/python3 }
     - func: "upload python release"
 
 - name: "release-python-linux"
@@ -563,7 +563,7 @@ tasks:
   commands:
     - func: "fetch source"
     - func: "build python release"
-      vars: { PYTHON: /opt/python/3.10/bin/python3 }
+      vars: { PYTHON: /opt/python/3.9/bin/python3 }
     - func: "upload python release"
 
 - name: "release-python-windows"
@@ -572,7 +572,7 @@ tasks:
   commands:
     - func: "fetch source"
     - func: "build python release"
-      vars: { PYTHON: C:/python/Python310/python.exe }
+      vars: { PYTHON: C:/python/Python39/python.exe }
     - func: "upload python release"
 
 - name: "release-python-combine"

From 80b72179897b01d8c1d9d178d0f4e2a31f3401a2 Mon Sep 17 00:00:00 2001
From: Steven Silvester <steve.silvester@mongodb.com>
Date: Wed, 30 Jul 2025 07:01:56 -0500
Subject: [PATCH 15/19] update config.yml

---
 .evergreen/config.yml | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/.evergreen/config.yml b/.evergreen/config.yml
index fb9b920d5..15ce3419b 100755
--- a/.evergreen/config.yml
+++ b/.evergreen/config.yml
@@ -553,7 +553,7 @@ tasks:
   commands:
     - func: "fetch source"
     - func: "build python release"
-      vars: { PYTHON: /Library/Frameworks/Python.framework/Versions/3.9/bin/python3 }
+      vars: { PYTHON: /Library/Frameworks/Python.framework/Versions/3.10/bin/python3 }
     - func: "upload python release"
 
 - name: "release-python-linux"

From 4344ce9157949e4e0569ce93c411ece084b4a2c2 Mon Sep 17 00:00:00 2001
From: Steven Silvester <steve.silvester@mongodb.com>
Date: Wed, 30 Jul 2025 07:02:51 -0500
Subject: [PATCH 16/19] update utils.sh

---
 bindings/python/.evergreen/utils.sh | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/bindings/python/.evergreen/utils.sh b/bindings/python/.evergreen/utils.sh
index e2d3923d5..99c41a72b 100755
--- a/bindings/python/.evergreen/utils.sh
+++ b/bindings/python/.evergreen/utils.sh
@@ -44,7 +44,7 @@ find_python3() {
     if [ "$(uname -s)" = "Darwin" ]; then
         PYTHON="/Library/Frameworks/Python.Framework/Versions/3.9/bin/python3"
     elif [ "Windows_NT" = "${OS:-}" ]; then # Magic variable in cygwin
-        PYTHON="C:/python/Python310/python.exe"
+        PYTHON="C:/python/Python39/python.exe"
     else
         # Prefer our own toolchain, fall back to mongodb toolchain if it has Python 3.9+.
         if [ -f "/opt/python/3.9/bin/python3" ]; then

From 50ccbc63ff007e3ed96eaa4ae7c0b49093ebfa64 Mon Sep 17 00:00:00 2001
From: Steven Silvester <steve.silvester@mongodb.com>
Date: Wed, 30 Jul 2025 07:03:19 -0500
Subject: [PATCH 17/19] update utils.sh

---
 bindings/python/.evergreen/utils.sh | 4 ++--
 1 file changed, 2 insertions(+), 2 deletions(-)

diff --git a/bindings/python/.evergreen/utils.sh b/bindings/python/.evergreen/utils.sh
index 99c41a72b..b96521e98 100755
--- a/bindings/python/.evergreen/utils.sh
+++ b/bindings/python/.evergreen/utils.sh
@@ -69,8 +69,8 @@ find_python3() {
 is_python_39() {
     if [ -z "$1" ]; then
         return 1
-    elif $1 -c "import sys; exit(sys.version_info[:2] < (3, 10))"; then
-        # runs when sys.version_info[:2] >= (3, 10)
+    elif $1 -c "import sys; exit(sys.version_info[:2] < (3, 9))"; then
+        # runs when sys.version_info[:2] >= (3, 9)
         return 0
     else
         return 1

From f1ce39286789900265545b8600f837cc346fb12c Mon Sep 17 00:00:00 2001
From: Steven Silvester <steve.silvester@mongodb.com>
Date: Wed, 30 Jul 2025 10:27:44 -0500
Subject: [PATCH 18/19] test on macos14

---
 .evergreen/config.yml | 8 ++++++++
 1 file changed, 8 insertions(+)

diff --git a/.evergreen/config.yml b/.evergreen/config.yml
index 15ce3419b..f84e659f5 100755
--- a/.evergreen/config.yml
+++ b/.evergreen/config.yml
@@ -1627,6 +1627,14 @@ buildvariants:
   tasks:
   - build-and-test-and-upload
   - test-python
+- name: macos-14
+  display_name: macOS 14 (arm)
+  run_on: macos-14-arm64
+  expansions:
+    compile_env: MACOS_UNIVERSAL=ON CMAKE=/opt/homebrew/bin/cmake
+  tasks:
+  - build-and-test-and-upload
+  - test-python
 - name: windows-vs2017-32bit
   # Test Windows 32 bit builds for PHPC. PHPC builds libmongocrypt from source. See MONGOCRYPT-391.
   display_name: "Windows VS 2017 32-bit compile"

From 4b493147846d449922b8e1e197dbbf2f01821ee7 Mon Sep 17 00:00:00 2001
From: Steven Silvester <steve.silvester@mongodb.com>
Date: Wed, 30 Jul 2025 10:49:10 -0500
Subject: [PATCH 19/19] skip 3.14 test on macos

---
 .evergreen/config.yml              | 8 --------
 bindings/python/.evergreen/test.sh | 3 ++-
 2 files changed, 2 insertions(+), 9 deletions(-)

diff --git a/.evergreen/config.yml b/.evergreen/config.yml
index f84e659f5..15ce3419b 100755
--- a/.evergreen/config.yml
+++ b/.evergreen/config.yml
@@ -1627,14 +1627,6 @@ buildvariants:
   tasks:
   - build-and-test-and-upload
   - test-python
-- name: macos-14
-  display_name: macOS 14 (arm)
-  run_on: macos-14-arm64
-  expansions:
-    compile_env: MACOS_UNIVERSAL=ON CMAKE=/opt/homebrew/bin/cmake
-  tasks:
-  - build-and-test-and-upload
-  - test-python
 - name: windows-vs2017-32bit
   # Test Windows 32 bit builds for PHPC. PHPC builds libmongocrypt from source. See MONGOCRYPT-391.
   display_name: "Windows VS 2017 32-bit compile"
diff --git a/bindings/python/.evergreen/test.sh b/bindings/python/.evergreen/test.sh
index 0c2f56dca..ccc916481 100755
--- a/bindings/python/.evergreen/test.sh
+++ b/bindings/python/.evergreen/test.sh
@@ -36,7 +36,8 @@ elif [ "Darwin" = "$(uname -s)" ]; then
           "/Library/Frameworks/Python.framework/Versions/3.11/bin/python3"
           "/Library/Frameworks/Python.framework/Versions/3.12/bin/python3"
           "/Library/Frameworks/Python.framework/Versions/3.13/bin/python3"
-          "/Library/Frameworks/Python.framework/Versions/3.14/bin/python3"
+          # TODO: PYTHON-5466
+          #"/Library/Frameworks/Python.framework/Versions/3.14/bin/python3"
           )
 
     export CRYPT_SHARED_PATH="../crypt_shared/lib/mongo_crypt_v1.dylib"