The OpenSSL included with OS X, still at 0.9.8, has become very dated and a growing number of servers (including openssl.org) now fail the handshake because they no longer support any of the protocols and ciphers included with that build. It is reaching the point where for some projects the system OpenSSL on OS X is no longer viable to use.

Here's a ticket for a Python project showing an example of this problem:

https://github.com/kivy/kivy-ios/issues/198

I have run into this issue myself on this and a couple other projects I am working on.

Would it be possible to have the fix for 10.5 builds get applied to all the Python OS X installers, perhaps for 3.6, and ideally also for 2.7 if there are plans to make a new release for that?