diff --git a/Lib/distutils/command/upload.py b/Lib/distutils/command/upload.py
--- a/Lib/distutils/command/upload.py
+++ b/Lib/distutils/command/upload.py
@@ -2,6 +2,7 @@

 Implements the Distutils 'upload' subcommand (upload package to PyPI)."""
 import os
+import sys
 import socket
 import platform
 from urllib2 import urlopen, Request, HTTPError
@@ -9,6 +10,7 @@
 import urlparse
 import cStringIO as StringIO
 from hashlib import md5
+import getpass

 from distutils.errors import DistutilsError, DistutilsOptionError
 from distutils.core import PyPIRCCommand
@@ -41,18 +43,33 @@
             raise DistutilsOptionError(
                 "Must use --sign for --identity to have meaning"
             )
+
         config = self._read_pypirc()
-        if config != {}:
-            self.username = config['username']
-            self.password = config['password']
-            self.repository = config['repository']
-            self.realm = config['realm']
+        # Empty config dict indicates non-existing or invalid .pypirc file.
+        # In this case, proceed using default settings (no authentication).
+        if not config:
+            return

-        # getting the password from the distribution
-        # if previously set by the register command
-        if not self.password and self.distribution.password:
+        # Use values provided via .pypirc file. If password was not
+        # specified in there, config['password'] is None.
+        self.username = config['username']
+        self.password = config['password']
+        self.repository = config['repository']
+        self.realm = config['realm']
+
+        # Use password if previously set by the register command.
+        if self.password is None and self.distribution.password:
             self.password = self.distribution.password

+        # If the password is still undefined, prompt for it (if stdin is
+        # attached to a terminal) or read directly from stdin.
+        if self.password is None:
+            if sys.stdin.isatty():
+                self.password = getpass.getpass('Enter password: ')
+            else:
+                self.announce("Reading password from stdin", log.INFO)
+                self.password = sys.stdin.readline().rstrip()
+
     def run(self):
         if not self.distribution.dist_files:
             raise DistutilsOptionError("No dist file created in earlier command")