diff --git a/src/trio/_tests/test_dtls.py b/src/trio/_tests/test_dtls.py
index 99cb68f11..307463988 100644
--- a/src/trio/_tests/test_dtls.py
+++ b/src/trio/_tests/test_dtls.py
@@ -1,6 +1,8 @@
 from __future__ import annotations
 
 import random
+import struct
+import sys
 from contextlib import asynccontextmanager
 from itertools import count
 from typing import TYPE_CHECKING, NoReturn
@@ -24,6 +26,11 @@
 
 from .._core._tests.tutil import binds_ipv6, gc_collect_harder, slow
 
+pytestmark = pytest.mark.skipif(
+    sys.platform == "win32" and struct.calcsize("P") == 4,
+    reason="SSL tests are not supported on 32-bit Windows",
+)
+
 if TYPE_CHECKING:
     from collections.abc import AsyncGenerator
 
diff --git a/src/trio/_tests/test_highlevel_ssl_helpers.py b/src/trio/_tests/test_highlevel_ssl_helpers.py
index 2d7f39372..cf86686da 100644
--- a/src/trio/_tests/test_highlevel_ssl_helpers.py
+++ b/src/trio/_tests/test_highlevel_ssl_helpers.py
@@ -1,5 +1,7 @@
 from __future__ import annotations
 
+import struct
+import sys
 from functools import partial
 from typing import TYPE_CHECKING, NoReturn, cast
 
@@ -18,6 +20,11 @@
 # using noqa because linters don't understand how pytest fixtures work.
 from .test_ssl import SERVER_CTX, client_ctx  # noqa: F401
 
+pytestmark = pytest.mark.skipif(
+    sys.platform == "win32" and struct.calcsize("P") == 4,
+    reason="SSL tests are not supported on 32-bit Windows",
+)
+
 if TYPE_CHECKING:
     from socket import AddressFamily, SocketKind
     from ssl import SSLContext
diff --git a/src/trio/_tests/test_ssl.py b/src/trio/_tests/test_ssl.py
index 8eb065927..f78a0fe1f 100644
--- a/src/trio/_tests/test_ssl.py
+++ b/src/trio/_tests/test_ssl.py
@@ -3,6 +3,7 @@
 import os
 import socket as stdlib_socket
 import ssl
+import struct
 import sys
 import threading
 from contextlib import asynccontextmanager, contextmanager, suppress
@@ -42,6 +43,11 @@
     memory_stream_pair,
 )
 
+pytestmark = pytest.mark.skipif(
+    sys.platform == "win32" and struct.calcsize("P") == 4,
+    reason="SSL tests are not supported on 32-bit Windows",
+)
+
 if TYPE_CHECKING:
     from collections.abc import AsyncIterator, Awaitable, Callable, Iterator