Sometimes the software update is free. All it needs is a half dozen VMs spun up (in an environment of 1500+) and an approved change window to migrate the current version to new servers, and then another window to update. But your request for new VMs gets back burnered for close to a year because there's still production machines on unsupported OSes.

Then a very large breach of the software in question happens while you're on vacation.

By sheer luck, the outdated version is not affected. But suddenly it's super important to upgrade to the latest version NOW. So you end up spending the next few days of vacation splitting your time between defending yourself, re-explaining the situation to "tech" VPs and up that are total frauds, and dealing with top level vendor support because migrating software and OS versions at the same time is not recommended. And then spending a nice relaxing overnight with one of their top engineers doing what was supposed to be an involved but routine process over multiple change windows, but is instead 9 hours of "this should work, guess we'll find out" sphincter-clenching Leroy Jenkins action, in which the top-level engineer was needed more than once to fix something. All this while flying blind on a 2000+ node network because the software you had to emergency update without any guardrails (aside from snapshots) is the network monitoring software. Hell of a thing to back-burner, but I didn't run the company that got sold for several billion so what do I know?

Oh, and three months later you get denied a merit raise because Covid and "nobody" got a raise.

So fucking glad to be rid of that toxic shithole.