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@libreleah I use Arch (btw) on most of my machines, but I still have 5-6 RPis around stuck on Bullseye (and two of them even on Buster) exactly because it’s always been a pain to run a proper dist-upgrade.

I don’t mind the half a day downtime when I manage only one Debian system, but when it’s 5-6 systems that easily become half a week just to manage upgrades, backports, broken packages etc. (sometimes in the past I just gave up and did a fresh install, which really sucked).

But if you can confirm that the process has finally become painless then I may even try to do the jump - I guess that the biggest blocker for me would be to migrate all the custom X11 scripts on those machines to Wayland, which I currently hate more than Pipewire…