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Re:Time to Upgrade Your Python: TLS v1.2 Will Soon Be Mandatory by mauntz on Wednesday February 01, 2017 @06:14AM (#13539826)
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!

Re:Time to Upgrade Your Python: TLS v1.2 Will Soon Be Mandatory by Lukasa on Wednesday February 01, 2017 @08:11AM (#13540415)
The python.org official installers are all linked against the system OpenSSL. You need to build from source to avoid that. I recommend getting Python from macports in this case, as they should allow you to link against their provided OpenSSL.
Re:Time to Upgrade Your Python: TLS v1.2 Will Soon Be Mandatory by pvg on Wednesday February 01, 2017 @09:14AM (#13540815)
The 3.6 macOS installer is bundled with its own, recent version of OpenSSL and supports TLS 1.2.
Re:Time to Upgrade Your Python: TLS v1.2 Will Soon Be Mandatory by mauntz on Thursday February 02, 2017 @10:28AM (#13551129)
Thanks for your replies! It's as I feared then. The switch to macports luckily isn't all that painful.
Re:Time to Upgrade Your Python: TLS v1.2 Will Soon Be Mandatory by pvg on Wednesday February 01, 2017 @10:49AM (#13541590)
The macports Python works fine, if you are able to use Python 3 you can also just use the official installer instead.