diff --git a/Lib/test/test_urllib2.py b/Lib/test/test_urllib2.py
index 7d7f2fa00d35b6..dd0246c6f37ea7 100644
--- a/Lib/test/test_urllib2.py
+++ b/Lib/test/test_urllib2.py
@@ -1543,19 +1543,24 @@ def test_osx_proxy_bypass(self):
                            '10.0/16']
         }
         # Check hosts that should trigger the proxy bypass
-        for host in ('foo.bar', 'www.bar.com', '127.0.0.1', '10.10.0.1',
+        for hostonly in ('foo.bar', 'www.bar.com', '127.0.0.1', '10.10.0.1',
                      '10.0.0.1'):
-            self.assertTrue(_proxy_bypass_macosx_sysconf(host, bypass),
-                            'expected bypass of %s to be True' % host)
+            for port in ('', ':80'):
+                host = hostonly + port
+                self.assertTrue(_proxy_bypass_macosx_sysconf(host, bypass),
+                                'expected bypass of %s to be True' % host)
         # Check hosts that should not trigger the proxy bypass
-        for host in ('abc.foo.bar', 'bar.com', '127.0.0.2', '10.11.0.1',
+        for hostonly in ('abc.foo.bar', 'bar.com', '127.0.0.2', '10.11.0.1',
                 'notinbypass'):
-            self.assertFalse(_proxy_bypass_macosx_sysconf(host, bypass),
-                             'expected bypass of %s to be False' % host)
+            for port in ('', ':80'):
+                host = hostonly + port
+                self.assertFalse(_proxy_bypass_macosx_sysconf(host, bypass),
+                                 'expected bypass of %s to be False' % host)
 
         # Check the exclude_simple flag
         bypass = {'exclude_simple': True, 'exceptions': []}
         self.assertTrue(_proxy_bypass_macosx_sysconf('test', bypass))
+        self.assertTrue(_proxy_bypass_macosx_sysconf('test:80', bypass))
 
         # Check that invalid prefix lengths are ignored
         bypass = {
diff --git a/Lib/urllib/request.py b/Lib/urllib/request.py
index 9a6b29a90a2968..b451698f665a20 100644
--- a/Lib/urllib/request.py
+++ b/Lib/urllib/request.py
@@ -1981,7 +1981,7 @@ def ip2num(ipAddr):
             if (hostIP >> mask) == (base >> mask):
                 return True
 
-        elif fnmatch(host, value):
+        elif fnmatch(hostonly, value):
             return True
 
     return False
diff --git a/Misc/NEWS.d/next/macOS/2025-04-18-06-36-46.gh-issue-132671.FRLb6i.rst b/Misc/NEWS.d/next/macOS/2025-04-18-06-36-46.gh-issue-132671.FRLb6i.rst
new file mode 100644
index 00000000000000..0f55e36ad42034
--- /dev/null
+++ b/Misc/NEWS.d/next/macOS/2025-04-18-06-36-46.gh-issue-132671.FRLb6i.rst
@@ -0,0 +1 @@
+Fix proxy bypass on URLs with a port in :mod:`urllib.request`.