diff -r 87b81b7df7f0 Lib/test/test_ssl.py
--- a/Lib/test/test_ssl.py	Mon Dec 16 20:22:37 2013 +0100
+++ b/Lib/test/test_ssl.py	Mon Dec 16 21:05:29 2013 +0100
@@ -1201,8 +1201,10 @@
                                 cert_reqs=ssl.CERT_REQUIRED,
                                 ca_certs=SVN_PYTHON_ORG_ROOT_CERT)
             try:
-                self.assertEqual(errno.ECONNREFUSED,
-                                 s.connect_ex(("svn.python.org", 444)))
+                rc = s.connect_ex(("svn.python.org", 444))
+                # Issue #19919: Windows machines or VMs hosted on Windows
+                # machines sometimes return EWOULDBLOCK.
+                self.assertIn(rc, (errno.ECONNREFUSED, errno.EWOULDBLOCK))
             finally:
                 s.close()