As referenced in this article[0] a major blocker for shipping newer versions of the command line toolchain is the fact that newer versions of these tools moved to an incompatible GPLv3 license.
Oh come on, that's far from serious. There are 6 pieces of software there that are old because newer versions are GPLv3. Grep could be replaced with bsdgrep, and nano could be replaced with pico and nobody would notice. The other 4 aren't that important for day to day use except bash and OSX should have switched users to zsh a long time ago, or simplified the shell by using tcsh as default.
The older version of openssh is rather perplexing, though, but they haven't updated any of the other bsd utilities really and the pf firewall is ancient too.
The older version of openssh is rather perplexing, though, but they haven't updated any of the other bsd utilities really and the pf firewall is ancient too.