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When something doesn't work. I.e. when an app update causes incompatibility with a service. I think I have one server that's a few years without an update (distro version may actually be EOL for all I know).
Why probably so may unpatched issues.
Ain't broke and I can't be bothered to update. Not accessible publicly either. It also runs some software with very specific and brittle dependencies and I don't care to risk breaking it. If distro is EOL (probably is) then it'd be a pretty time consuming getting everything set up again.