diff --git a/Lib/test/test_urllib2_localnet.py b/Lib/test/test_urllib2_localnet.py
--- a/Lib/test/test_urllib2_localnet.py
+++ b/Lib/test/test_urllib2_localnet.py
@@ -1,3 +1,4 @@
+import base64
 import os
 import email
 import urllib.parse
@@ -197,6 +198,42 @@
                 return self._return_auth_challenge(request_handler)
             return True
 
+
+class BasicAuthHandler(http.server.SimpleHTTPRequestHandler):
+    """Handler for performing basic authentication."""
+    # Server side values
+    USER = 'testUser'
+    PASSWD = 'testPass'
+    REALM = 'Test'
+    USER_PASSWD = "%s:%s" % (USER, PASSWD)
+    ENCODED_AUTH = base64.b64encode(USER_PASSWD.encode('ascii')).decode('ascii')
+
+    def __init__(self, *args, **kwargs):
+         http.server.SimpleHTTPRequestHandler.__init__(self, *args, **kwargs)
+
+    def do_HEAD(self):
+        self.send_response(200)
+        self.send_header("Content-type", "text/html")
+        self.end_headers()
+
+    def do_AUTHHEAD(self):
+        self.send_response(401)
+        self.send_header("WWW-Authenticate", "Basic realm=\"%s\"" % self.REALM)
+        self.send_header("Content-type", "text/html")
+        self.end_headers()
+
+    def do_GET(self):
+        if not self.headers.get("Authorization"):
+            self.do_AUTHHEAD()
+            self.wfile.write(b"No Auth header received")
+        elif self.headers.get("Authorization") == "Basic " + self.ENCODED_AUTH:
+            http.server.SimpleHTTPRequestHandler.do_GET(self)
+        else:
+            self.do_AUTHHEAD()
+            self.wfile.write(bytes(self.headers.get("Authorization"), "ascii"))
+            self.wfile.write(b"Not Authenticated")
+
+
 # Proxy test infrastructure
 
 class FakeProxyHandler(http.server.BaseHTTPRequestHandler):
@@ -233,6 +270,45 @@
 # Test cases
 
 @unittest.skipUnless(threading, "Threading required for this test.")
+class BasicAuthTests(unittest.TestCase):
+    USER = "testUser"
+    PASSWD = "testPass"
+    INCORRECT_PASSWD = "Incorrect"
+    REALM = "Test"
+
+    def setUp(self):
+        super(BasicAuthTests, self).setUp()
+        # With Basic Authentication
+        def http_server_with_basic_auth_handler(*args, **kwargs):
+            return BasicAuthHandler(*args, **kwargs)
+        self.server = LoopbackHttpServerThread(http_server_with_basic_auth_handler)
+        self.server_url = 'http://127.0.0.1:%s' % self.server.port
+        self.server.start()
+        self.server.ready.wait()
+
+    def tearDown(self):
+        self.server.stop()
+        super(BasicAuthTests, self).tearDown()
+
+    def test_basic_auth_success(self):
+        ah = urllib.request.HTTPBasicAuthHandler()
+        ah.add_password(self.REALM, self.server_url, self.USER, self.PASSWD)
+        urllib.request.install_opener(urllib.request.build_opener(ah))
+        try:
+            self.assertTrue(urllib.request.urlopen(self.server_url))
+        except urllib.error.HTTPError:
+            self.fail("Basic auth failed for the url: %s", self.server_url)
+        except Exception as e:
+            raise e
+
+    def test_basic_auth_httperror(self):
+        ah = urllib.request.HTTPBasicAuthHandler()
+        ah.add_password(self.REALM, self.server_url, self.USER, self.INCORRECT_PASSWD)
+        urllib.request.install_opener(urllib.request.build_opener(ah))
+        self.assertRaises(urllib.error.HTTPError, urllib.request.urlopen, self.server_url)
+
+
+@unittest.skipUnless(threading, "Threading required for this test.")
 class ProxyAuthTests(unittest.TestCase):
     URL = "http://localhost"
 
@@ -245,6 +321,7 @@
         self.digest_auth_handler = DigestAuthHandler()
         self.digest_auth_handler.set_users({self.USER: self.PASSWD})
         self.digest_auth_handler.set_realm(self.REALM)
+        # With Digest Authentication.
         def create_fake_proxy_handler(*args, **kwargs):
             return FakeProxyHandler(self.digest_auth_handler, *args, **kwargs)
 
diff --git a/Lib/urllib/request.py b/Lib/urllib/request.py
--- a/Lib/urllib/request.py
+++ b/Lib/urllib/request.py
@@ -846,10 +846,6 @@
             password_mgr = HTTPPasswordMgr()
         self.passwd = password_mgr
         self.add_password = self.passwd.add_password
-        self.retried = 0
-
-    def reset_retry_count(self):
-        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
@@ -857,13 +853,6 @@
         # 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:
             scheme = authreq.split()[0]
             if scheme.lower() != 'basic':
@@ -878,17 +867,14 @@
                         warnings.warn("Basic Auth Realm was unquoted",
                                       UserWarning, 2)
                     if scheme.lower() == 'basic':
-                        response = self.retry_http_basic_auth(host, req, realm)
-                        if response and response.code != 401:
-                            self.retried = 0
-                        return response
+                        return self.retry_http_basic_auth(host, req, realm)
 
     def retry_http_basic_auth(self, host, req, realm):
         user, pw = self.passwd.find_user_password(realm, host)
         if pw is not None:
             raw = "%s:%s" % (user, pw)
             auth = "Basic " + base64.b64encode(raw.encode()).decode("ascii")
-            if req.headers.get(self.auth_header, None) == auth:
+            if req.get_header(self.auth_header, None) == auth:
                 return None
             req.add_unredirected_header(self.auth_header, auth)
             return self.parent.open(req, timeout=req.timeout)
@@ -904,7 +890,6 @@
         url = req.full_url
         response = self.http_error_auth_reqed('www-authenticate',
                                           url, req, headers)
-        self.reset_retry_count()
         return response
 
 
@@ -920,7 +905,6 @@
         authority = req.host
         response = self.http_error_auth_reqed('proxy-authenticate',
                                           authority, req, headers)
-        self.reset_retry_count()
         return response