diff -r 38a325c84564 Lib/distutils/command/upload.py
--- a/Lib/distutils/command/upload.py	Wed Jun 11 17:09:43 2014 -0400
+++ b/Lib/distutils/command/upload.py	Thu Jun 12 01:33:43 2014 +0100
@@ -12,7 +12,7 @@
 from base64 import standard_b64encode
 from urllib.request import urlopen, Request, HTTPError
 from urllib.parse import urlparse
-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
@@ -184,7 +184,7 @@
             reason = result.msg
         except OSError as e:
             self.announce(str(e), log.ERROR)
-            return
+            raise
         except HTTPError as e:
             status = e.code
             reason = e.msg
@@ -193,8 +193,9 @@
             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)
         if self.show_response:
             text = self._read_pypi_response(result)
             msg = '\n'.join(('-' * 75, text, '-' * 75))
diff -r 38a325c84564 Lib/distutils/tests/test_upload.py
--- a/Lib/distutils/tests/test_upload.py	Wed Jun 11 17:09:43 2014 -0400
+++ b/Lib/distutils/tests/test_upload.py	Thu Jun 12 01:33:43 2014 +0100
@@ -6,6 +6,7 @@
 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.log import INFO
 
 from distutils.tests.test_config import PYPIRC, PyPIRCCommandTestCase
@@ -41,13 +42,14 @@
 
 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 getheader(self, name, default=None):
         return {
@@ -58,7 +60,7 @@
         return b'xyzzy'
 
     def getcode(self):
-        return 200
+        return self.code
 
 
 class uploadTestCase(PyPIRCCommandTestCase):
@@ -68,13 +70,15 @@
         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):
@@ -135,6 +139,14 @@
         results = self.get_logs(INFO)
         self.assertIn('xyzzy\n', results[-1])
 
+    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)