Ugh. Righteous ideas about how things should work don't change the fact that these network appliances doing it the wrong way still have years of time left before the bean counters consider them depreciated and let us replace them. Or that we're locked into a multi-year contract with this business system that requires updating certs through a web UI.

Yes, there are almost always workarounds and ways to still automate it in the end, but then it's a matter of effort vs stability vs time savings.

I love automating manual sysadmin actions, it's my primary role on my team. Still, ignoring the complications that will unavoidably arise in trying automating this for every unique setup is incredibly foolish.