Microsoft is probably one of the worst offenders, especially in the past few years. It seems like they're actively destroying documentation and making it hard to find important information, so much that I often use archive.org instead.
All documentation on Help Books was archived, for instance. It's been 7 years since they've seen an update and they now contain inaccuracies – but there are no other official guides. Check out that UI: https://developer.apple.com/library/archive/documentation/Ca...
This is a technology that is still used. Nearly all of Apple's own apps have Help Books, including new ones like Shortcuts. Yet they have absolutely no official documentation on using that technology.
Off-topic, but damn - tune down that candyness a bit and it looks much better and cleaner than what's there today.
I don't get Microsoft. They're huge. They hire a lot of people. Their products are kludges.