Christian Heimes <li...@cheimes.de> added the comment:

Oh heck, this is a genuine bug. I'm not yet sure if it's an undocumented API 
quirk in OpenSSL, a design bug in OpenSSL, or a bug in my code.

Python sets the host flags on the X509_VERIFY_PARAM of the *SSL_CTX. All flags 
get copied to *SSL struct and later to *X509_STORE_CTX struct. At least I 
thought that all flags get copied. Apparently hostflags aren't copied from 
*SSL_CTX to *SSL because the *SSL_CTX doesn't have any verify hosts configured. 
They are only ever configured on *SSL struct.

https://github.com/openssl/openssl/blob/081a7061f3da07318c4b0f5de67b82285630bf6b/crypto/x509/x509_vpm.c#L202-L213

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<https://bugs.python.org/issue43522>
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