diff --git a/Lib/test/test_ssl.py b/Lib/test/test_ssl.py
index aa8ce81db6688be..0876d4d8a434874 100644
--- a/Lib/test/test_ssl.py
+++ b/Lib/test/test_ssl.py
@@ -5041,15 +5041,27 @@ def non_linux_skip_if_other_okay_error(self, err):
             return  # Expect the full test setup to always work on Linux.
         if (isinstance(err, ConnectionResetError) or
             (isinstance(err, OSError) and err.errno == errno.EINVAL) or
-            re.search('wrong.version.number', getattr(err, "reason", ""), re.I)):
+            re.search(
+                # Matches the following error messages:
+                # '[SSL: WRONG_VERSION_NUMBER] wrong version number (_ssl.c:1123)'
+                # '[SSL: RECORD_LAYER_FAILURE] record layer failure (_ssl.c:1109)'
+                # '[SSL: HTTP_REQUEST] http request (_ssl.c:1143)'
+                r'wrong.version.number|record.layer.failure|http.request',
+                str(getattr(err, "reason", "")),
+                re.IGNORECASE,
+            )
+        ):
             # On Windows the TCP RST leads to a ConnectionResetError
             # (ECONNRESET) which Linux doesn't appear to surface to userspace.
             # If wrap_socket() winds up on the "if connected:" path and doing
-            # the actual wrapping... we get an SSLError from OpenSSL. Typically
-            # WRONG_VERSION_NUMBER. While appropriate, neither is the scenario
-            # we're specifically trying to test. The way this test is written
-            # is known to work on Linux. We'll skip it anywhere else that it
-            # does not present as doing so.
+            # the actual wrapping... we get an SSLError from OpenSSL. This is
+            # typically WRONG_VERSION_NUMBER. The same happens on iOS, but
+            # RECORD_LAYER_FAILURE or HTTP_REQUEST is the error.
+            #
+            # While appropriate, these scenarios aren't what we're specifically
+            # trying to test. The way this test is written is known to work on
+            # Linux. We'll skip it anywhere else that it does not present as
+            # doing so.
             try:
                 self.skipTest(f"Could not recreate conditions on {sys.platform}:"
                               f" {err=}")