Most folks probably know this, but with another year's passage, it's worth a reminder: Apple hates having to maintain open source tools and libraries. The release schedules and security patches never align with Apple's own, and the old code becomes a greater liability each year. As a result, Apple has abandoned in place many of the most important tools that live in /usr/bin and the like. The best way for you to easily stay current is to use Homebrew. Here are some examples of what shipped with Mojave versus what is more current in Homebrew: Code: Mojave Brew Perl 5.18.2 Jan 14 5.28.0 Jun 18 Python 2.7.10 May 15 2.7.15 May 18 Python3 Missing 3.7.0 Jun 18 OpenSSL 2.6.4* Dec 17 1.1.1* Sept 18 rsync 2.6.9 Nov 06 3.1.3 Jan 18 awk May 07 Aug 18 *Apple switched to LibreSSL, so these aren't directly comparable, but it is worth noting that Mojave's openssl shipped without TLS 1.3 support–one of those cases completely beyond their control due to the timing. These are just a few examples that I use regularly. Some of the deltas are quantum leaps in terms of features, particularly rsync. Homebrew makes it easy to get the latest security fixes and features across all your Macs. This is also particularly useful if you also work with other Unices which are maintained more rigorously.