I don't understand as much as I'd like about this stuff, BUT isn't the problem here "just" that my /boot is too small (OK, shit happens says Forrest Gump) and that the system automatically tries to keep more previous kernel versions on /boot than there is space for? Glancing over http://askubuntu.com/questions/620266/how-does-apt-decide-how-many-old-kernels-to-keep, I'm wondering if whatever setting determines how many old kernels versions to keep around on /boot couldn't auto-tune itself more appropriately based on real actual free disk space on /boot? In a perfectly ideal world, of course; I certainly fully respect you may have other higher priorities than this kind of nice to have end-user usability gimmick.
I don't understand as much as I'd like about this stuff, BUT isn't the problem here "just" that my /boot is too small (OK, shit happens says Forrest Gump) and that the system automatically tries to keep more previous kernel versions on /boot than there is space for? Glancing over http:// askubuntu. com/questions/ 620266/ how-does- apt-decide- how-many- old-kernels- to-keep, I'm wondering if whatever setting determines how many old kernels versions to keep around on /boot couldn't auto-tune itself more appropriately based on real actual free disk space on /boot? In a perfectly ideal world, of course; I certainly fully respect you may have other higher priorities than this kind of nice to have end-user usability gimmick.