So I was looking at yet another failed apt-get upgrade because /boot was full.
After my initial whining on Twitter, I immediately received a hint towards /etc/apt/apt.conf.d/01autoremove-kernels, which gets generated from /etc/kernel/postinst.d/apt-auto-removal after the installation of new kernel images. The file contains a list of kernels that the package manager considers vital at this time. In theory, all kernels not covered by this list should be able to be autoremoved by running apt-get autoremove.
However it turns out that apt-get autoremove would not remove any kernels at all, at least not on this system. After a bit of peeking around on Stackexchange, it turns out that this still somewhat newish concept seems to be ridden by a few bugs, especially concerning kernels that are (Wrongfully? Rightfully? I just don’t know.) marked as manually-installed in the APT database: “Why doesn’t apt-get autoremove remove my old kernels?”
The solution, as suggested by an answer to the linked question, is to mark all kernel packages as autoinstalled before running apt-get autoremove:
apt-mark showmanual | grep -E "^linux-([[:alpha:]]+-)+[[:digit:].]+-[^-]+(|-.+)$" | xargs -n 1 apt-mark auto
I’m not an APT expert, but I’m posting this because the post-install hook that prevents the current kernel from being autoremoved makes the procedure appear “safe enough”. As always, reader discretion is advised. And there’s also the hope that it will get sorted out fully in the future.