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From: Antoine Pitrou <solipsis@pitrou.net>
Subject: Re: ssl handshake operation timed out on Python 3.3.2
Date: Tue, 9 Jul 2013 10:08:01 +0000 (UTC)
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Xref: csiph.com comp.lang.python:50230

Benedict Verheyen <benedict.verheyen <at> gmail.com> writes:
> 
> Hi,
> 
> for a project, I need to post data to some aspx pages.
> The aspx pages are hosted by another company.
> I develop on a virtual Debian Wheezy (Virtual box) running on Windows.
> I couldn't get the code to run either on Windows nor Linux.
> 
> On my testserver (also a Debian Linux Wheezy) however, the code works with 
> Python 2.7.3 but not with Python 3.3.2. Another difference is that the 
> testserver has a direct ip, so nothing in between the machine and the 
> internet. I checked the firewall, the traffic passes without a problem.
> 
> The error I get is that the SSL handshake operation timed out.
> I tried some code that specifies the ssl protocol but the results are the 
> same.

This may be a IIS-specific problem.
Take a look at
http://stackoverflow.com/questions/16365483/iis-7-5-mercurial-setup-ignoring-maxallowedcontentlength
http://bz.selenic.com/show_bug.cgi?id=3905
http://bugs.python.org/issue17948

Otherwise, dumping network traffic with Wireshark could give you some hints
at to what is different between the SSL handshakes in the two setups.

Regards

Antoine.