Antoine Pitrou added the comment:

By the way, please check the return value of getaddrinfo() for your SMTP server:

>>> socket.getaddrinfo("www.gmail.com", 25, 0, socket.SOCK_STREAM)
[(2, 1, 6, '', ('74.125.230.213', 25)), (2, 1, 6, '', ('74.125.230.214', 25)), 
(10, 1, 6, '', ('2a00:1450:4007:802::1016', 25, 0, 0))]

and then try to connect() to each of the addresses. If one of the addresses 
gives WSAEACCES when connecting, you've got the explanation.

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Python tracker <rep...@bugs.python.org>
<http://bugs.python.org/issue15779>
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