Python/OpenSSL issue: ERROR:root:code for hash md5 was not found
So the problem is actually coming that python2 is not supported, but you can solve it by installing just correct openssl via brew, e.g.
brew install openssl@1.1
This error occurred while installing latest Ruby using ruby-install.
What I tried:
brew switch openssl <my_version>
brew upgrade openssl
And many other solutions that were proposed in SO. None solved my problem.