ssl handshake operation timed out on Python 3.3.2

Antoine Pitrou solipsis at
Tue Jul 9 12:08:01 CEST 2013

Benedict Verheyen <benedict.verheyen <at>> 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

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



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