Christian Heimes added the comment:

IMHO SSL CTX set cert verify callback() is the wrong approach. Your are 
completely bypassing cert validation checks of OpenSSL. The callback has to 
build the chain and perform all checks on its own. By all checks I literally 
mean *all*, 
https://wiki.openssl.org/index.php/Manual:SSL_CTX_set_cert_verify_callback(3)#WARNINGS

Basically you want to replace OpenSSL's X509 verification with Windows' cert 
validation and just leave the handshake and encryption to OpenSSL?

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Python tracker <rep...@bugs.python.org>
<http://bugs.python.org/issue28747>
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