Beware that Surface computers need a custom kernel for some features to work. It depends on the distro and the features you use, but I’d suggest you see the linux-surface project for more info. As for updates, standard Debian has a stable release model, and is one of the more stable Linux distros in general, so I don’t think he would have issues with any automatic updates. I’d just say that you should try to be on standby for tech support, as Linux has many differences and is naturally a bit more prone to issues than Windows.

Debian Stable - yes.

Debian Testing or Sid - 😈

I’ve diverged from Debian for desktop use for a few years now (no particular good reason, just for fun) but I have extended family with about the same affinity to updates as your dad.

I think automatic updates for regular end users are nice nowdays, especially if you don’t customise stuff too much (DEs, wm, things like that). And even if some issues ever occur in return you get a continuously up-to-date and safer system (imho worth it). And its not like not-updating os solves the issues, it just postpones them, potentially snowballs them (and in that case I just reinstall it).
I switched my dad to Tumbleweed like 3 years ago & set weekly automatic updates, literally no issues with it.

As for serves, Im all for automatic updates in home environment, since my kinda worst case scenario is rolling back to a previous snapshot.
Maybe I could set backup services on a separate node with delayed updates … but I need more motivation (a clusterfuck) for that.

I’ve been running Debian stable on my decade-old desktop for about 3 years, and on my ideapad that’s just as old for about 5. During that time I had an update break something only once, and it was the Nvidia driver what did it. A patch was released within a three days.

Debian epitomizes OS transparency for me. Sure, I can still customize the hell out of it and turn it into a frankenix machine, but if I don’t want to, I can be blissfully unaware of how my OS works, and focus only on important computing tasks (like mindlessly scrolling lemmy at 2 am).

I’ve been running Debian stable with unattended-upgrades on servers for years and have had no issues whatsoever.

On desktop I usually do manual installation of updates(mostly cos I don’t want to get any important running program restarted), in servers I use automatic updates via cron job as part of the automation process, these two work for me.

Speaking of which, Debian users, how safe are distribution upgrades?

I’ve had unattended upgrades running on a home server for a couple years and haven’t had any issues.

Fedora Silverblue downloads new OS versions in the background and boots the newest version after a reboot. I use this for older family member who’s been traumatised by Windows updates. I have also turned off notificantions that show up after a new boot with a fresh version.

The same goes for Flatpaks. Just updates without make a fuzz.

Its nice to give old people some peace of mind regarding their computing needs!