diff -r e28004fb30c0 Lib/smtplib.py
--- a/Lib/smtplib.py	Sun Jun 22 20:26:07 2014 -0700
+++ b/Lib/smtplib.py	Mon Jun 23 18:58:08 2014 -0400
@@ -784,9 +784,19 @@
             if self.debuglevel > 0:
                 print>>stderr, 'connect:', (host, port)
             new_socket = socket.create_connection((host, port), timeout)
-            new_socket = ssl.wrap_socket(new_socket, self.keyfile, self.certfile)
+            try:
+                ssl_socket = ssl.wrap_socket(new_socket, self.keyfile, self.certfile)
+            except:
+                new_socket.close()
+                raise
+            try:
+                ssl_socket.do_handshake()
+            except:
+                ssl_socket.close()
+                raise
+
             self.file = SSLFakeFile(new_socket)
-            return new_socket
+            return ssl_socket
 
     __all__.append("SMTP_SSL")