Linking OpenSSL 1.1.0e installed manually to python2.7
OpenSSL 1.0.2 and OpenSSL 1.1.0 are not compatible at the API level. This means that you cannot simply relink Python against the new libssl and libcrypto. Instead you need to rebuild Python with the new libssl and libcrypto, as described in How do I compile Python 3.4 with custom OpenSSL? or Building Python with SSL support in non-standard location.
Python3 - Issue with module pyOpenSSL
I think this error was caused by the OpenSSL version.
I used this link to upgrade the OpenSSL version and it worked:
Manually update the openssl version used by python on windows x64
I managed to solve this with some help.
The scripts used by CPython to build OpenSSL for the windows installers actually run the command:
Perl Configure VC-WIN64A-masm no-asm
instead of
Perl Configure VC-WIN64A
After running the correct command on the setup described in my original post I was able to swap out the dlls and python accepted them without issue.
ssl.OPENSSL_VERSION now outputs ‘OpenSSL 1.1.1i 8 Dec 2020’.
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