And then they went towards a more evergreen update strategy, causing some major outages when some releases caused issues.

I mean evergreen releases make sense imo, as the overhead of maintaining older versions for a long time is huge, but you need to have canary releases, monitoring, and gradual rollout plans; for something like Windows, this should be done with a lot of care. Even a 1% release rate will affect hundreds of thousands if not millions of systems.