diff --git a/Lib/test/test_urllib2.py b/Lib/test/test_urllib2.py
index 9364b3d7c4c..b5a243705a2 100644
--- a/Lib/test/test_urllib2.py
+++ b/Lib/test/test_urllib2.py
@@ -1143,7 +1143,6 @@ class HandlerTests(unittest.TestCase):
         self.assertEqual(len(http_handler.requests), 1)
         self.assertFalse(http_handler.requests[0].has_header(auth_header))
 
-
 class MiscTests(unittest.TestCase):
 
     def test_build_opener(self):
diff --git a/Lib/urllib2.py b/Lib/urllib2.py
index 43ca53d1ce1..40e442751e0 100644
--- a/Lib/urllib2.py
+++ b/Lib/urllib2.py
@@ -819,12 +819,21 @@ class AbstractBasicAuthHandler:
             password_mgr = HTTPPasswordMgr()
         self.passwd = password_mgr
         self.add_password = self.passwd.add_password
+        self.retried = 0
 
     def http_error_auth_reqed(self, authreq, host, req, headers):
         # host may be an authority (without userinfo) or a URL with an
         # authority
         # XXX could be multiple headers
         authreq = headers.get(authreq, None)
+
+        if self.retried > 5:
+            # retry sending the username:password 5 times before failing.
+            raise HTTPError(req.get_full_url(), 401, "basic auth failed",
+                            headers, None)
+        else:
+            self.retried += 1
+
         if authreq:
             mo = AbstractBasicAuthHandler.rx.search(authreq)
             if mo: