Sometimes, yes. Usually API changes or something, and it happens on Linux occasionally (partly because I’m on Arch which is more fragile than Fedora or Ubuntu). Even though the libraries are version numbered, it still goes wrong occasionally.
However, despite the fact that I rarely use Windows for anything other than flying, even Arch’s update is way more reliable. Despite its reputation.
As a dreadful example, the installation of MSFS from Microsoft store, which appears unable to cope with dependencies - you have to sort of prod it into installing some runtimes, stops after a while for no apparent reason visibly but keeps going in the background, and calculates transfer rates that are physically beyond my connection.
Thing is in Windows, except for the .NET framework, the whole thing is like that. MSFS AFAICS contains the FSX core, upgraded in places, with bolt on modules. If you are old enough, you’ll remember when Windows was three executable files pretty much 
It hasn’t improved much.