László Károlyi <las...@karolyi.hu> added the comment:

Upon reinstalling openssl with homebrew, I get the following info:

--------------
openssl is keg-only, which means it was not symlinked into /usr/local,
because Apple has deprecated use of OpenSSL in favor of its own TLS and crypto 
libraries.

If you need to have openssl first in your PATH run:
  echo 'set -g fish_user_paths "/usr/local/opt/openssl/bin" $fish_user_paths' 
>> ~/.config/fish/config.fish

For compilers to find openssl you may need to set:
  set -gx LDFLAGS "-L/usr/local/opt/openssl/lib"
  set -gx CPPFLAGS "-I/usr/local/opt/openssl/include"

For pkg-config to find openssl you may need to set:
  set -gx PKG_CONFIG_PATH "/usr/local/opt/openssl/lib/pkgconfig"
----------------

So assumingly the system-wide library should be preferred, may it be whatever 
one.

`/usr/bin/openssl version` says LibreSSL 2.8.3.

Probably I could still link to the homebrew installed SSL using the provided 
flags, but I'm quite sure this same problem will pop up at a lot of other 
Catalina users.

----------

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Python tracker <rep...@bugs.python.org>
<https://bugs.python.org/issue38814>
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