This is not a full guide yet, I basically followed bullseye but messed up and ended up jumping to bookworm instead. The bug in the bullseye procedure has been since then fixed, but it's still worth reporting on some of the problems I encountered.

Issues

Pending

Packages removed from bookworm

At the time of this writing (long before the freeze), there's a significant number of packages gone from bookworm, which I actually want to have installed on my machines:

Resolved

libcrypt disappeared on upgrade

It's unclear how that happened, but I somehow lost libcrypt.so.1 during the upgrade, which pretty much broke everything, including Python, Perl, and Ruby, which, in turn, broke apt-listbugs, apt-listchanges, and, more critically, debconf. The later was especially hairy because libc requires debconf to at least function (if it's installed!) during its postinst.

The workaround was to add a bunch of false && in the libc postinst. I also had to manually install a bunch of packages with dpkg from /var/cache/apt/archives. And other tricks, I don't remember it all but it was scary and hairy.

Packages to remove from my configuration

Created . Edited .