diff --git a/Lib/test/test_ssl.py b/Lib/test/test_ssl.py
index 06d4598..f235daf 100644
--- a/Lib/test/test_ssl.py
+++ b/Lib/test/test_ssl.py
@@ -835,8 +835,10 @@
                                 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()
 
diff --git a/Misc/NEWS b/Misc/NEWS
index cacfb7c..7c0232d 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -149,6 +149,9 @@
 Tests
 -----
 
+- Issue #19919: Fix flacky SSL test. connect_ex() sometimes returns
+  EWOULDBLOCK on Windows or VMs hosted on Windows.
+
 - Issue #19912: Added tests for ntpath.splitunc().
 
 - Issue #19828: Fixed test_site when the whole suite is run with -S.