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

This is probably a duplicate of #36137. Windows doesn't have CA certs 
pre-installed. They are downloaded from the update server on demand. Python 
doesn't trigger the update but only uses certs that are already present.

It's a design flaw in my implementation. I wasn't aware of Windows' behavior 
when I hooked up the Windows cert store to the SSL module.

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Python tracker <rep...@bugs.python.org>
<https://bugs.python.org/issue36137>
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