diff --git a/.evergreen/generated_configs/variants.yml b/.evergreen/generated_configs/variants.yml
index e98b0d342c..d4726a22a9 100644
--- a/.evergreen/generated_configs/variants.yml
+++ b/.evergreen/generated_configs/variants.yml
@@ -319,6 +319,15 @@ buildvariants:
     expansions:
       PYTHON_BINARY: /Library/Frameworks/PythonT.Framework/Versions/3.13/bin/python3t
     tags: []
+  - name: free-threaded-win64-python3.14t
+    tasks:
+      - name: .free-threading
+    display_name: Free-threaded Win64 Python3.14t
+    run_on:
+      - windows-64-vsMulti-small
+    expansions:
+      PYTHON_BINARY: C:/python/Python314/python3.14t.exe
+    tags: []
 
   # Green framework tests
   - name: green-eventlet-rhel8
diff --git a/.evergreen/scripts/generate_config.py b/.evergreen/scripts/generate_config.py
index a30beb1d39..c27cfe130f 100644
--- a/.evergreen/scripts/generate_config.py
+++ b/.evergreen/scripts/generate_config.py
@@ -108,14 +108,14 @@ def create_free_threaded_variants() -> list[BuildVariant]:
     variants = []
     for host_name in ("rhel8", "macos", "macos-arm64", "win64"):
         if host_name == "win64":
-            # TODO: PYTHON-5027
-            continue
+            python = "3.14t"
+        else:
+            python = "3.13t"
         tasks = [".free-threading"]
         tags = []
         if host_name == "rhel8":
             tags.append("pr")
         host = HOSTS[host_name]
-        python = "3.13t"
         display_name = get_variant_name("Free-threaded", host, python=python)
         variant = create_variant(tasks, display_name, tags=tags, python=python, host=host)
         variants.append(variant)
diff --git a/.evergreen/scripts/generate_config_utils.py b/.evergreen/scripts/generate_config_utils.py
index 62ea982cd8..e676200d38 100644
--- a/.evergreen/scripts/generate_config_utils.py
+++ b/.evergreen/scripts/generate_config_utils.py
@@ -153,18 +153,17 @@ def get_python_binary(python: str, host: Host) -> str:
             base = "C:/python/32"
         else:
             base = "C:/python"
-        python = python.replace(".", "")
-        if python == "313t":
-            return f"{base}/Python313/python3.13t.exe"
-        return f"{base}/Python{python}/python.exe"
+        python_dir = python.replace(".", "").replace("t", "")
+        return f"{base}/Python{python_dir}/python{python}.exe"
 
     if name in ["rhel8", "ubuntu22", "ubuntu20", "rhel7"]:
         return f"/opt/python/{python}/bin/python3"
 
     if name in ["macos", "macos-arm64"]:
-        if python == "3.13t":
-            return "/Library/Frameworks/PythonT.Framework/Versions/3.13/bin/python3t"
-        return f"/Library/Frameworks/Python.Framework/Versions/{python}/bin/python3"
+        bin_name = "python3t" if "t" in python else "python3"
+        python_dir = python.replace("t", "")
+        framework_dir = "PythonT" if "t" in python else "Python"
+        return f"/Library/Frameworks/{framework_dir}.Framework/Versions/{python_dir}/bin/{bin_name}"
 
     raise ValueError(f"no match found for python {python} on {name}")
 
diff --git a/pyproject.toml b/pyproject.toml
index fb2dd58131..e7e3161906 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -111,6 +111,9 @@ filterwarnings = [
     "module:Wire protocol compression with:UserWarning",
     "module:GridIn property:DeprecationWarning",
     "module:GridOut property:DeprecationWarning",
+    # pytest-asyncio known issue: https://github.com/pytest-dev/pytest-asyncio/issues/1032
+    "module:.*WindowsSelectorEventLoopPolicy:DeprecationWarning",
+    "module:.*et_event_loop_policy:DeprecationWarning",
     # TODO: Remove as part of PYTHON-3923.
     "module:unclosed <eventlet.green.ssl.GreenSSLSocket:ResourceWarning",
     "module:unclosed <socket.socket:ResourceWarning",
diff --git a/test/__init__.py b/test/__init__.py
index 40d58cff89..95c2d7ee9d 100644
--- a/test/__init__.py
+++ b/test/__init__.py
@@ -30,7 +30,7 @@
 import traceback
 import unittest
 import warnings
-from asyncio import iscoroutinefunction
+from inspect import iscoroutinefunction
 
 from pymongo.errors import AutoReconnect
 from pymongo.synchronous.uri_parser import parse_uri
diff --git a/test/asynchronous/__init__.py b/test/asynchronous/__init__.py
index 5d52c348df..96769dc9c5 100644
--- a/test/asynchronous/__init__.py
+++ b/test/asynchronous/__init__.py
@@ -30,7 +30,7 @@
 import traceback
 import unittest
 import warnings
-from asyncio import iscoroutinefunction
+from inspect import iscoroutinefunction
 
 from pymongo.asynchronous.uri_parser import parse_uri
 from pymongo.errors import AutoReconnect
diff --git a/test/asynchronous/helpers.py b/test/asynchronous/helpers.py
index 49b9af9bf7..bcb004af51 100644
--- a/test/asynchronous/helpers.py
+++ b/test/asynchronous/helpers.py
@@ -29,7 +29,7 @@
 import traceback
 import unittest
 import warnings
-from asyncio import iscoroutinefunction
+from inspect import iscoroutinefunction
 
 from pymongo._asyncio_task import create_task
 
diff --git a/test/asynchronous/test_comment.py b/test/asynchronous/test_comment.py
index d3ddaf2b65..2d6d0f5f1e 100644
--- a/test/asynchronous/test_comment.py
+++ b/test/asynchronous/test_comment.py
@@ -20,7 +20,7 @@
 import sys
 
 sys.path[0:0] = [""]
-from asyncio import iscoroutinefunction
+from inspect import iscoroutinefunction
 from test.asynchronous import AsyncIntegrationTest, async_client_context, unittest
 from test.utils_shared import OvertCommandListener
 
diff --git a/test/asynchronous/test_session.py b/test/asynchronous/test_session.py
index d357948ed0..5ed3597751 100644
--- a/test/asynchronous/test_session.py
+++ b/test/asynchronous/test_session.py
@@ -19,7 +19,7 @@
 import copy
 import sys
 import time
-from asyncio import iscoroutinefunction
+from inspect import iscoroutinefunction
 from io import BytesIO
 from test.asynchronous.helpers import ExceptionCatchingTask
 from typing import Any, Callable, List, Set, Tuple
diff --git a/test/asynchronous/unified_format.py b/test/asynchronous/unified_format.py
index 5b2e3563f9..b9cebd0fab 100644
--- a/test/asynchronous/unified_format.py
+++ b/test/asynchronous/unified_format.py
@@ -27,8 +27,8 @@
 import sys
 import time
 import traceback
-from asyncio import iscoroutinefunction
 from collections import defaultdict
+from inspect import iscoroutinefunction
 from test.asynchronous import (
     AsyncIntegrationTest,
     async_client_context,
diff --git a/test/asynchronous/utils.py b/test/asynchronous/utils.py
index 2b82355fc1..02ba46c71a 100644
--- a/test/asynchronous/utils.py
+++ b/test/asynchronous/utils.py
@@ -23,8 +23,8 @@
 import threading  # Used in the synchronized version of this file
 import time
 import traceback
-from asyncio import iscoroutinefunction
 from functools import wraps
+from inspect import iscoroutinefunction
 
 from bson.son import SON
 from pymongo import AsyncMongoClient
diff --git a/test/asynchronous/utils_spec_runner.py b/test/asynchronous/utils_spec_runner.py
index 3ce2984c62..496c28a045 100644
--- a/test/asynchronous/utils_spec_runner.py
+++ b/test/asynchronous/utils_spec_runner.py
@@ -20,8 +20,8 @@
 import os
 import time
 import unittest
-from asyncio import iscoroutinefunction
 from collections import abc
+from inspect import iscoroutinefunction
 from test.asynchronous import AsyncIntegrationTest, async_client_context, client_knobs
 from test.asynchronous.helpers import ConcurrentRunner
 from test.utils_shared import (
diff --git a/test/helpers.py b/test/helpers.py
index ccf19a9228..22bdc0d25d 100644
--- a/test/helpers.py
+++ b/test/helpers.py
@@ -29,7 +29,7 @@
 import traceback
 import unittest
 import warnings
-from asyncio import iscoroutinefunction
+from inspect import iscoroutinefunction
 
 from pymongo._asyncio_task import create_task
 
diff --git a/test/test_bson_binary_vector.py b/test/test_bson_binary_vector.py
index ba3eff8bb2..2783338793 100644
--- a/test/test_bson_binary_vector.py
+++ b/test/test_bson_binary_vector.py
@@ -15,7 +15,6 @@
 from __future__ import annotations
 
 import binascii
-import codecs
 import struct
 from pathlib import Path
 from test import unittest
@@ -111,7 +110,7 @@ def run_test(self):
 
 def create_tests():
     for filename in _TEST_PATH.glob("*.json"):
-        with codecs.open(str(filename), encoding="utf-8") as test_file:
+        with open(str(filename), encoding="utf-8") as test_file:
             test_method = create_test(json_util.loads(test_file.read()))
         setattr(TestBSONBinaryVector, "test_" + filename.stem, test_method)
 
diff --git a/test/test_bson_corpus.py b/test/test_bson_corpus.py
index 96ef458ec5..504025e766 100644
--- a/test/test_bson_corpus.py
+++ b/test/test_bson_corpus.py
@@ -16,7 +16,6 @@
 from __future__ import annotations
 
 import binascii
-import codecs
 import functools
 import glob
 import json
@@ -227,7 +226,7 @@ def run_test(self):
 def create_tests():
     for filename in glob.glob(os.path.join(_TEST_PATH, "*.json")):
         test_suffix, _ = os.path.splitext(os.path.basename(filename))
-        with codecs.open(filename, encoding="utf-8") as bson_test_file:
+        with open(filename, encoding="utf-8") as bson_test_file:
             test_method = create_test(json.load(bson_test_file))
         setattr(TestBSONCorpus, "test_" + test_suffix, test_method)
 
diff --git a/test/test_comment.py b/test/test_comment.py
index b6c17c14fe..bcab0061fa 100644
--- a/test/test_comment.py
+++ b/test/test_comment.py
@@ -20,7 +20,7 @@
 import sys
 
 sys.path[0:0] = [""]
-from asyncio import iscoroutinefunction
+from inspect import iscoroutinefunction
 from test import IntegrationTest, client_context, unittest
 from test.utils_shared import OvertCommandListener
 
diff --git a/test/test_session.py b/test/test_session.py
index d8add9f3b6..16a219ae52 100644
--- a/test/test_session.py
+++ b/test/test_session.py
@@ -19,7 +19,7 @@
 import copy
 import sys
 import time
-from asyncio import iscoroutinefunction
+from inspect import iscoroutinefunction
 from io import BytesIO
 from test.helpers import ExceptionCatchingTask
 from typing import Any, Callable, List, Set, Tuple
diff --git a/test/unified_format.py b/test/unified_format.py
index 859cb29977..2c10506fc0 100644
--- a/test/unified_format.py
+++ b/test/unified_format.py
@@ -27,8 +27,8 @@
 import sys
 import time
 import traceback
-from asyncio import iscoroutinefunction
 from collections import defaultdict
+from inspect import iscoroutinefunction
 from test import (
     IntegrationTest,
     client_context,
diff --git a/test/utils.py b/test/utils.py
index 3447440927..bfc606fe83 100644
--- a/test/utils.py
+++ b/test/utils.py
@@ -23,8 +23,8 @@
 import threading  # Used in the synchronized version of this file
 import time
 import traceback
-from asyncio import iscoroutinefunction
 from functools import wraps
+from inspect import iscoroutinefunction
 
 from bson.son import SON
 from pymongo import MongoClient
diff --git a/test/utils_shared.py b/test/utils_shared.py
index e0789b6632..f2e8852f0c 100644
--- a/test/utils_shared.py
+++ b/test/utils_shared.py
@@ -26,9 +26,9 @@
 import threading
 import unittest
 import warnings
-from asyncio import iscoroutinefunction
 from collections import abc, defaultdict
 from functools import partial
+from inspect import iscoroutinefunction
 from test import client_context
 from test.asynchronous.utils import async_wait_until
 from test.utils import wait_until
diff --git a/test/utils_spec_runner.py b/test/utils_spec_runner.py
index c0a8c81e30..46adeaefb5 100644
--- a/test/utils_spec_runner.py
+++ b/test/utils_spec_runner.py
@@ -20,8 +20,8 @@
 import os
 import time
 import unittest
-from asyncio import iscoroutinefunction
 from collections import abc
+from inspect import iscoroutinefunction
 from test import IntegrationTest, client_context, client_knobs
 from test.helpers import ConcurrentRunner
 from test.utils_shared import (
diff --git a/tools/convert_test_to_async.py b/tools/convert_test_to_async.py
index dbdb217c84..6c68c34bf3 100644
--- a/tools/convert_test_to_async.py
+++ b/tools/convert_test_to_async.py
@@ -1,6 +1,6 @@
 from __future__ import annotations
 
-import asyncio
+import inspect
 import sys
 
 from pymongo import AsyncMongoClient
@@ -83,7 +83,7 @@ def get_async_methods() -> set[str]:
             for k, v in vars(x).items()
             if callable(v)
             and not isinstance(v, classmethod)
-            and asyncio.iscoroutinefunction(v)
+            and inspect.iscoroutinefunction(v)
             and v.__name__[0] != "_"
         }
         result = result | methods