A few years ago I turned on my windows machine to see the dreaded upgrade. Being in a rush I went to another machine and the exact thing happened. I blew my top and replaced all windows with Ubuntu. I would have preferred Macs but I couldn't afford the Apple tax (high prices and not working on my existing HW).
That's nice for you, but if you use any non-open software or software not covered by the package repo then there's a fairly good chance you'll see downtime after an upgrade of your linux distro.
To be clear, I was talking specifically about the unattended-upgrades package, which is primarily for automatic installation of things like security fixes. In my experience, this has been rock solid: it's never broken a distro package, nor any dependency that non-distro software we had installed was relying on.
Also, in many years my amount of downtime due to Debian's unattended-upgrades is exactly 0. The same cannot be said of Windows updates.
I'm still hoping Microsoft see the light on all the telemetry and forced update nonsense before the Windows 7 cut-off in a couple of years. The trouble is, I can't see it happening as long as Nadella is at the top, and I can't see that changing as long as the big enterprise customers who aren't subject to that kind of nonsense are propping up the share price.