mauntz

Thanks for your replies! It's as I feared then. The switch to macports luckily isn't all that painful.

I am running a Python 2.7.13 installed with official Python installer on macOS Sierra (10.12.3). Besides the built-in openssl (0.9.8zh) which came along with the macOS (/usr/bin/openssl), I have a newer version (1.0.2j) installed with macports (/opt/local/bin/openssl).

However, even though I have configured my path variables that it will use the macports openssl-files, the Python installer seems to link by default to the /usr/... openssl-files.

I've tried quite a bit re-installing Python (with the installer and building it from source; the latter failed with some obscure error I wasn't able to resolve), so I was wondering whether there are any better options. Upgrading via homebrew seems simple enough, but due to using macports, I'd rather not use homebrew. Furthermore, I am a bit reluctant to use the macports-python, but might do that if you were to suggest me that this is the only viable solution.

I'd be happy to hear your suggestions on this!