Antoine Pitrou added the comment:

By using "openssl s_client -connect 172.23.6.222:443" you can open a 
telnet-like session (but using SSL) to your server, and try to type/paste an 
HTTP request there. That would help check whether it's a Python problem, or 
something else due to OpenSSL changes.

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<http://bugs.python.org/issue16109>
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