The problem isn't automatic updates, it's the philosophy behind those updates. On Ubuntu (last time I used it some 5 years ago), an update fixed bugs in software and that's it. Occasionally you'd get a new feature here and there, but rarely in the shell and existing features always stayed in their places. On Windows 10, updates ship breaking changes basically every time and there is no regard for consistency. Whether the updates are manual or automatic is an implementation detail - eventually, you'll update either way. The big difference is between a rolling release with no promise of compatibility and a versioned release with LTS.

Strange, my experience is also the exact opposite. I really wonder why that is?

I'm running about 10 windows 10 machines, various builds, auto updates enabled. Some in a domain, some in a workgroup. The last time an update bricked a system, or even broke a feature, must be over a year ago.

Now on Ubuntu, I have the same experience as some other posters. I'm reasonably confident that I can update if I do it semi regularly. But the number of times I've experienced breakage that lead to hours of bugfixing during $DAYJOB, is way too high. Now everything is in its own tightly controller docker, no more random breakage (unless docker breaks, or a key expires...).

A debian 9 apt upgrade actually managed to render my install inoperable once. But that might be semi-unfair as it had to do with graphics drivers.

Are you running windows systems on semi-recent hardware? Or is it all decades old thinkpad laptops with shitty thirdparty drivers?

This is literally the opposite to me. Running apt update/upgrade never breaks anything except a long time ago when I ran out of disk space during an update. This could have been handled better, but it isn't a usual scenario for me.

I can attest to this anxiety. There is always this question of what will happen if the update is botched and it bricks my system. This is why I consciously stay slim on the host OS (I have used Fedora in the past, and am now using Arch), and run almost all of my applications via Docker from a local container repository. The /home/username directory is backed up rigorously in the internal network so as to cover my ass if an update bricks my computer. As paranoid as I am to go through this, I am yet to need that backup because of a botched update ;-) The only times I reached out to backup were "I deleted this, but I shouldn't have..." scenarios.

The same paranoia applies to my MacBook Pro as well that was provided by work. All user generated content gets backed up regularly to aid recovery if things go north.

It's more than that isn't it? On Ubuntu I never candy crush come pre-installed, and I never have random popups on the bottom right corner of the screen for all types of reasons