This has been a real problem again in the Windows 10 era. By around 2008, Microsoft seemed to have finally gotten their patch process cleaned up to the point th

This has been a real problem again in the Windows 10 era. By around 2008, Microsoft seemed to have finally gotten their patch process cleaned up to the point that if you were only taking security patches, they generally installed cleanly and mostly didn't break random things. By about 2016 this has backslid and now Windows 10 seems intent on large scale combined updates and constant servicing stack updates that with undocumented consequences. It's been a giant pain having spent years trying to get organizations to accept the need and learn to do this stuff reliably only to have the primary source of misery (Microsoft) repeatedly start biting them in the ass again for what should be best practices. Meanwhile in the same timeframe most BSD and Linux releases have not only gotten their core software updates down to a science, they've also managed to build workflows that can include huge swathes of 3rd party open source and commercial software, which is so hilariously awful on windows that multiple companies build businesses around doing it.