[jraph]

> I’ve started to develop a form of “upgrade dread” when it comes to OS upgrades.

I've been going the other way on Linux.

I used to think it might be wise to postpone updates if you were traveling, especially using a rolling distro. Today, I would be quite confident running the updates 10 minutes before leaving.

Granted, this is also because I'm more confident than ever that I could fix most breakages, and worst case the smartphone is there, but I've also not seen big breakages for years.

[kccqzy]

I have a somewhat opposite experience. I also use a rolling distro, and in the past six months, I've seen wine break, and I've also seen Citrix Workspace break due to a dependency problem (perhaps Mesa?). Granted, these two cases are somewhat unusual because Citrix Workspace is closed source and the software I'm running with wine is also closed source. I rarely experience breakages of open source software other than GNOME extensions.

[microtonal]

Yep. I run NixOS unstable-small on my ThinkPad and there is rarely breakage in daily updates. If it ever happens while on the go, I can just boot into a previous generation. The immutable OSTree/bootc distros are similar, as well as openSUSE, which uses btrfs snapshots on updates.