diff --git a/tests/test_proxy_functional.py b/tests/test_proxy_functional.py
index 8433dca23de..bd3a174a893 100644
--- a/tests/test_proxy_functional.py
+++ b/tests/test_proxy_functional.py
@@ -1,9 +1,9 @@
 # type: ignore
 import asyncio
-import functools
 import os
 import pathlib
-import platform
+import ssl
+import sys
 from re import match as match_regex
 from typing import Any
 from unittest import mock
@@ -15,8 +15,7 @@
 
 import aiohttp
 from aiohttp import web
-from aiohttp.client_exceptions import ClientConnectionError, ClientProxyConnectionError
-from aiohttp.helpers import PY_310
+from aiohttp.client_exceptions import ClientConnectionError
 
 pytestmark = [
     pytest.mark.filterwarnings(
@@ -30,20 +29,7 @@
 ]
 
 
-secure_proxy_xfail = functools.partial(
-    pytest.mark.xfail,
-    (PY_310 and platform.system() != "Darwin") or platform.system() == "Windows",
-    reason=(
-        "The secure proxy fixture does not seem to work "
-        "under Python 3.10 on Linux and any Python on Windows. "
-        "See https://github.com/abhinavsingh/proxy.py/issues/622."
-    ),
-)
-
-ASYNCIO_SUPPORTS_TLS_IN_TLS = hasattr(
-    asyncio.sslproto._SSLProtocolTransport,
-    "_start_tls_compatible",
-)
+ASYNCIO_SUPPORTS_TLS_IN_TLS = sys.version_info >= (3, 11)
 
 
 @pytest.fixture
@@ -53,7 +39,9 @@ def secure_proxy_url(tls_certificate_pem_path):
     This fixture also spawns that instance and tears it down after the test.
     """
     proxypy_args = [
-        "--threadless",  # use asyncio
+        # --threadless does not work on windows, see
+        # https://github.com/abhinavsingh/proxy.py/issues/492
+        "--threaded" if os.name == "nt" else "--threadless",
         "--num-workers",
         "1",  # the tests only send one query anyway
         "--hostname",
@@ -113,32 +101,20 @@ async def handler(*args, **kwargs):
     )
 
 
-@pytest.fixture
-def _pretend_asyncio_supports_tls_in_tls(
-    monkeypatch,
-    web_server_endpoint_type,
-):
-    if web_server_endpoint_type != "https" or ASYNCIO_SUPPORTS_TLS_IN_TLS:
-        return
-
-    # for https://github.com/python/cpython/pull/28073
-    # and https://bugs.python.org/issue37179
-    monkeypatch.setattr(
-        asyncio.sslproto._SSLProtocolTransport,
-        "_start_tls_compatible",
-        True,
-        raising=False,
-    )
-
-
-@secure_proxy_xfail(raises=ClientProxyConnectionError)
+@pytest.mark.skipif(
+    not ASYNCIO_SUPPORTS_TLS_IN_TLS,
+    reason="asyncio on this python does not support TLS in TLS",
+)
 @pytest.mark.parametrize("web_server_endpoint_type", ("http", "https"))
-@pytest.mark.usefixtures("_pretend_asyncio_supports_tls_in_tls", "loop")
+@pytest.mark.filterwarnings(r"ignore:.*ssl.OP_NO_SSL*")
+# Filter out the warning from
+# https://github.com/abhinavsingh/proxy.py/blob/30574fd0414005dfa8792a6e797023e862bdcf43/proxy/common/utils.py#L226
+# otherwise this test will fail because the proxy will die with an error.
 async def test_secure_https_proxy_absolute_path(
-    client_ssl_ctx,
-    secure_proxy_url,
-    web_server_endpoint_url,
-    web_server_endpoint_payload,
+    client_ssl_ctx: ssl.SSLContext,
+    secure_proxy_url: URL,
+    web_server_endpoint_url: str,
+    web_server_endpoint_payload: str,
 ) -> None:
     """Ensure HTTP(S) sites are accessible through a secure proxy."""
     conn = aiohttp.TCPConnector()
@@ -158,13 +134,19 @@ async def test_secure_https_proxy_absolute_path(
     await conn.close()
 
 
-@secure_proxy_xfail(raises=AssertionError)
 @pytest.mark.parametrize("web_server_endpoint_type", ("https",))
 @pytest.mark.usefixtures("loop")
+@pytest.mark.skipif(
+    ASYNCIO_SUPPORTS_TLS_IN_TLS, reason="asyncio on this python supports TLS in TLS"
+)
+@pytest.mark.filterwarnings(r"ignore:.*ssl.OP_NO_SSL*")
+# Filter out the warning from
+# https://github.com/abhinavsingh/proxy.py/blob/30574fd0414005dfa8792a6e797023e862bdcf43/proxy/common/utils.py#L226
+# otherwise this test will fail because the proxy will die with an error.
 async def test_https_proxy_unsupported_tls_in_tls(
-    client_ssl_ctx,
-    secure_proxy_url,
-    web_server_endpoint_type,
+    client_ssl_ctx: ssl.SSLContext,
+    secure_proxy_url: URL,
+    web_server_endpoint_type: str,
 ) -> None:
     """Ensure connecting to TLS endpoints w/ HTTPS proxy needs patching.