Adam Goodman added the comment:

I just tried installing the root certificate update from KB931125 on a clean 
VM. Now I have 369 trusted root CAs, according to certmgr.msc. (I imagine it 
would be unreasonable to expect all windows python users to do this, though...)

The https request to python.org does succeed - but the code I'd thrown together 
to print out the SSLContext state breaks somehow:

> Traceback (most recent call last):
>   File "C:/Users/IEUser/Desktop/win_ssl_test.py", line 8, in <module>
>     ca_certs = context.get_ca_certs()
> ssl.SSLError: unknown error (_ssl.c:636)

Peeking at _ssl.c, it seems like it might be failing to decode some attributes 
on one (or more) of the certs...?

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Python tracker <rep...@bugs.python.org>
<http://bugs.python.org/issue20916>
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