On September 11th, 2018 the OpenSSL team released a Long Term Support (LTS) version (1.1.1) of OpenSSL which will be supported by the community and the core team for the next five years. This LTS release includes many new features such as TLS 1.3, ABI version compatibility, new cryptography algorithms, and an overhaul in many areas to the random number generators included in OpenSSL.
Python just received a minor version update to Python 3.7 with many new performance enhancements, added features, and module improvements to the language. One of the existing Python modules in 3.7 that received some nice new enhancements is the ssl module. The updated ssl module now has enhanced hostname support, updates to how blacklisting and whitelisting work, but most importantly, conditional support for TLS 1.3 connections.
One of my favorite sessions I attended at WWDC this year was entitled "Your Apps and Evolving Network Security Standards." I highly encourage anyone to watch the video who has not already. It was a session covering all of the latest network security enhancements that Apple is supporting across their platforms.