diff -r c43362d35d8d Lib/smtplib.py
--- a/Lib/smtplib.py	Fri Jul 04 17:00:25 2014 -0700
+++ b/Lib/smtplib.py	Wed Jul 23 01:13:34 2014 +0200
@@ -937,9 +937,18 @@
             new_socket = socket.create_connection((host, port), timeout,
                     self.source_address)
             server_hostname = self._host if ssl.HAS_SNI else None
-            new_socket = self.context.wrap_socket(new_socket,
-                                                  server_hostname=server_hostname)
-            return new_socket
+            try:
+                ssl_socket = self.context.wrap_socket(
+                    new_socket, server_hostname=server_hostname)
+            except:
+                new_socket.close()
+                raise
+            try:
+                ssl_socket.do_handshake()
+            except:
+                ssl_socket.close()
+                raise
+            return ssl_socket
 
     __all__.append("SMTP_SSL")