Cory Benfield added the comment:

The problem specifically is that OpenSSL only uses a *root* in the trust store 
as an anchor. That means any certificate that is signed by another certificate 
will not terminate the chain of trust. Browsers do better here, by trusting the 
entirety of the trust store, regardless of whether or not it's a root 
certificate.

Donald is correct: this is not really Python's fault, it's OpenSSL's.

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Python tracker <rep...@bugs.python.org>
<http://bugs.python.org/issue23476>
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