ImportError: cannot import name 'HTTPSConnection' · Issue ...
github.com › jarun › googlerDec 12, 2019 · Updating OpenSSL is usually fine, the jump from libssl.1.0.0.dylib to libssl.1.1.dylib is extremely rare. The dylib version number 1.0.0 has been the same for years. However, when it does change and you remove the old one, everything that depends on it will break (Homebrew can do its best making sure its packages are all recompiled, but it can't do anything about your pyenv Python installs).