This probably happens at universities and colleges more than anywhere else.
Yes, it is irritating that older faculty won't migrate to Word from WordPerfect, but WordPerfect historically had the edge in editing large documents like book drafts, and the job of the faculty is to publish or perish AND to teach. That problem probably isn't as pronounced these days, and isn't as important as Expensive Equipment. If your chemistry lab bought a gas chromatograph mass spectrometer many years ago for $20000+ and that GC mass spec will only talk to a machine running Windows XP, your job is not to chastise them about how they need to go out and spend ANOTHER $20000 because you can't support Windows XP any longer. That GC mass spec is more expensive than any computer or number of computers the department will buy, so it needs to become a priority to support such things, even if it means making exceptions to policy.
It is all about getting work done, and if policy is making people needlessly spend redundant dollars and holding up the process of doing work, it means IT is broken.