Paul Moore added the comment:

Thanks Tim.

To clarify, the only 2 places that pip calls ctypes is to get the user 
application directory (and we've confirmed that doesn't error when called 
direct from Python), and in the vendored colorama package (which we removed and 
still got the crash, so it's not that).

So as far as we can tell, the crash is occurring from pure Python code, which 
as the OP pointed out, should not occur. The issue has also been confirmed as 
not happening with 2.7.11.

If anyone can suggest a way for the OP to get better information out of Python 
as to where the problem is occurring, I'm happy to debug further with him in 
the pip code in order to reproduce the issue.

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Python tracker <rep...@bugs.python.org>
<http://bugs.python.org/issue27305>
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