diff --git a/Apple/testbed/__main__.py b/Apple/testbed/__main__.py
index 0dd77ab8b82797..b3eed38571d970 100644
--- a/Apple/testbed/__main__.py
+++ b/Apple/testbed/__main__.py
@@ -21,7 +21,7 @@
 LOG_PREFIX_REGEX = re.compile(
     r"^\d{4}-\d{2}-\d{2}"  # YYYY-MM-DD
     r"\s+\d+:\d{2}:\d{2}\.\d+\+\d{4}"  # HH:MM:SS.ssssss+ZZZZ
-    r"\s+iOSTestbed\[\d+:\w+\]"  # Process/thread ID
+    r"\s+iOSTestbed\[\d+:\w+\] "  # Process/thread ID
 )
 
 
diff --git a/Lib/test/test_ssl.py b/Lib/test/test_ssl.py
index a12b17fa8e2e02..dd4c657d0cf192 100644
--- a/Lib/test/test_ssl.py
+++ b/Lib/test/test_ssl.py
@@ -5347,17 +5347,24 @@ 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', str(getattr(err, "reason", "")), re.I) or
-            re.search('record.layer.failure', str(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. This is
             # typically WRONG_VERSION_NUMBER. The same happens on iOS, but
-            # RECORD_LAYER_FAILURE is the error.
+            # RECORD_LAYER_FAILURE or HTTP_REQUEST is the error.
             #
-            # While appropriate, neither is the scenario we're specifically
+            # 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.