diff --git a/Lib/urllib2.py b/Lib/urllib2.py
index 43ca53d..40e4427 100644
--- a/Lib/urllib2.py
+++ b/Lib/urllib2.py
@@ -819,12 +819,21 @@
             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: