I am a sysadmin and believe me when I say that happens. Mostly due to updates.
Within that updates that just plainly break things. E.g. deleting the users files. Or other updates which only break some PCs. (those are fun to diagnose) E.g. if the recovery partiton created by its own installer is suddenly to small. and I also had it more than a few times that Windows pulled in a driver "update" which broke things. One time it even tried to apply the wrong driver! I have now disabled all driver updates trough windows on all PCs I manage.
Rarely PCs also just suddenly refuse to boot, being caught in a recovery loop. After trying two times for hours to find the reason and only one success I don't care anymore and just restore a working backup in that case. Mind that (nearly) all users do not have admin rights.
On Linux? I had it that release upgrades broke things, but only once several years ago on the PCs where I wait till the official release is made. On my own ones I am often to feature hungry to wait until after the beta, and I know I can fix things.
I had one 12 year old PC where X11+KDE got unstable after a release upgrade, thankfully a switch to Wayland solved this.
Besides that? Never had any issue I didn't cause myself and never had a running system which suddenly broke.
Granted I do not administer as many Linux PCs as Windows ones. But there are a few, some of them also in the hands of users.