diff -r 9438a8aa3622 Lib/distutils/command/upload.py
--- a/Lib/distutils/command/upload.py	Wed Jun 11 06:18:43 2014 -0700
+++ b/Lib/distutils/command/upload.py	Thu Jun 12 01:26:38 2014 +0100
@@ -10,7 +10,7 @@
 import cStringIO as StringIO
 from hashlib import md5
 
-from distutils.errors import DistutilsOptionError
+from distutils.errors import DistutilsError, DistutilsOptionError
 from distutils.core import PyPIRCCommand
 from distutils.spawn import spawn
 from distutils import log
@@ -181,7 +181,7 @@
                 self.announce(msg, log.INFO)
         except socket.error, e:
             self.announce(str(e), log.ERROR)
-            return
+            raise
         except HTTPError, e:
             status = e.code
             reason = e.msg
@@ -190,5 +190,6 @@
             self.announce('Server response (%s): %s' % (status, reason),
                           log.INFO)
         else:
-            self.announce('Upload failed (%s): %s' % (status, reason),
-                          log.ERROR)
+            msg = 'Upload failed (%s): %s' % (status, reason)
+            self.announce(msg, log.ERROR)
+            raise DistutilsError(msg)
diff -r 9438a8aa3622 Lib/distutils/tests/test_upload.py
--- a/Lib/distutils/tests/test_upload.py	Wed Jun 11 06:18:43 2014 -0700
+++ b/Lib/distutils/tests/test_upload.py	Thu Jun 12 01:26:38 2014 +0100
@@ -7,6 +7,7 @@
 from distutils.command import upload as upload_mod
 from distutils.command.upload import upload
 from distutils.core import Distribution
+from distutils.errors import DistutilsError
 
 from distutils.tests.test_config import PYPIRC, PyPIRCCommandTestCase
 
@@ -41,16 +42,17 @@
 
 class FakeOpen(object):
 
-    def __init__(self, url):
+    def __init__(self, url, msg=None, code=None):
         self.url = url
         if not isinstance(url, str):
             self.req = url
         else:
             self.req = None
-        self.msg = 'OK'
+        self.msg = msg or 'OK'
+        self.code = code or 200
 
     def getcode(self):
-        return 200
+        return self.code
 
 
 class uploadTestCase(PyPIRCCommandTestCase):
@@ -60,13 +62,15 @@
         self.old_open = upload_mod.urlopen
         upload_mod.urlopen = self._urlopen
         self.last_open = None
+        self.next_msg = None
+        self.next_code = None
 
     def tearDown(self):
         upload_mod.urlopen = self.old_open
         super(uploadTestCase, self).tearDown()
 
     def _urlopen(self, url):
-        self.last_open = FakeOpen(url)
+        self.last_open = FakeOpen(url, msg=self.next_msg, code=self.next_code)
         return self.last_open
 
     def test_finalize_options(self):
@@ -124,6 +128,15 @@
         auth = self.last_open.req.headers['Authorization']
         self.assertNotIn('\n', auth)
 
+    def test_upload_fails(self):
+        try:
+            self.next_msg = "Not Found"
+            self.next_code = 404
+            self.assertRaises(DistutilsError, self.test_upload)
+        finally:
+            self.next_msg = None
+            self.next_code = None
+
 def test_suite():
     return unittest.makeSuite(uploadTestCase)