Chih-Hsuan Yen <yan12...@gmail.com> added the comment:

Hi Michael Felt,

> And, what it looks like you are trying to do with an updated 'signing" .pem 
> is to remove the 'self-signed' charasteric.

If I understand it correctly, the new certificate is indeed still self-signed. 
It's updated to match the certificate deployed at 
https://self-signed.pythontest.net/. Under the hood load_verify_locations() at 
line 1628 is used to make the test accept any valid certificate signed with the 
given certificate.

As a record, with CPython e7cb23bf2079087068a08502f96fdf20b317d69c and OpenSSL 
1.1.1b on Arch Linux x86_64, the test is green:

test_networked_good_cert (test.test_httplib.HTTPSTest) ... ok

By the way, I believe the "key too weak" workaround can be removed now and then 
this issue can be closed.

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<https://bugs.python.org/issue36816>
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