Humm what version of python are you using? 2.7.11 does have 
source_address 
https://hg.python.org/releases/2.7.11/file/tip/Lib/smtplib.py#l248

Basically the problem here google is that google returning an IPv6 address 
to your socket.getaddrinfo(host, port) before the IPv4 addresses so it 
tries to connect to that one first. 

Your options seem to be:
 - Set a PTR record for your IPv6 address
 - disable IPv6 system wide
 - monkeypatch socket.create_connection to ignore IPv6 results from 
socket.getaddrinfo.

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- http://web2py.com/book (Documentation)
- http://github.com/web2py/web2py (Source code)
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