diff --git a/cheroot/test/test_ssl.py b/cheroot/test/test_ssl.py
index 3475b25d27..11fd61559a 100644
--- a/cheroot/test/test_ssl.py
+++ b/cheroot/test/test_ssl.py
@@ -469,6 +469,15 @@ def test_http_over_https_error(
             and IS_WIN2016
             and adapter_type == 'builtin'
             and ip_addr is ANY_INTERFACE_IPV6
+    ):
+        expect_fallback_response_over_plain_http = True
+    if (
+            IS_GITHUB_ACTIONS_WORKFLOW
+            and IS_WINDOWS
+            and six.PY2
+            and not IS_WIN2016
+            and adapter_type == 'builtin'
+            and ip_addr is not ANY_INTERFACE_IPV6
     ):
         expect_fallback_response_over_plain_http = False
     if expect_fallback_response_over_plain_http: