[KronisLV]

That's funny, because it's not unheard of for even simple unattended updates to break something, for example: https://blog.kronis.dev/everything%20is%20broken/debian-and-...

(the tone of that blog post of mine is a bit vitriolic and the advice isn't exactly serious, but the fact of the matter is that sooner or later things will break)

[selfhoster11]

OK, fair enough. I guess you can minimally complicate this by updating an exactly identical machine/boot drive first, and then immediately alerting if health checks fail on that. But it really doesn't seem that bad to me. I've run a VPS that's been self-updating continuously since Feb 2019, and I've not had many breaking issues with the OS.