Whenever a kernel is updated autoremove should be called immediately afterwards. It should be called before the restart now / restart later dialog box of update-notifier appears.
Currently, Ubuntu installs a new kernel and update-notifier tells the user a reboot is needed. The autoremove notification only appears when using the terminal which explains why users are running into this issue. Also, update-notifier informs the user another reboot is needed after autoremove is run.
To avoid this mess I’ve commented out the lines of /etc/apt/apt.conf.d/99update-notifier and wrote my own updater using bash and zenity and incorporated needsrestart. It’s not pretty but it works.
absolutely not, automatically running auto remove may lead to bad things; on occasion autoremove flags other more useful packages for removal.
For example I'm using LVM with my installation on my Ubuntu laptop and after updating the kernel and running "apt autoremove" it removed the LVM package leaving me scratching my head shortly on reboot as to why it wouldn't find my root filesystem (frankly i have no idea how it became "unneeded").
A more sensible approach is how Red Hat do it with YUM/DNF, that is, to allow a certain number of the same packages to be installed, "installonly_limit" in yum.conf. Doing this means that when a new kernel gets installed the oldest is removed to keep the the system at the limit specified.
On my RHEL/CentOS machines I tend to narrowly provision /boot to around 250-500MB. set "installonly_limit" to 2 and the system will keep the most recent kernel and one back. it works for me.
I see you’re point, though I too use LVM and haven’t seen that happen... weird. I could have been more exact with my response as autoremove does more than just remove old kernels. Anyway, it would be nice to see Canonical resolve this.
I thought about sharing it but like I said it’s not pretty. It involves editing sudoers and holding back config updates for sudoers and update-notifier-common which might cause problems in the future if you’re not aware. I’d much rather see Canonical address it properly.
Currently, Ubuntu installs a new kernel and update-notifier tells the user a reboot is needed. The autoremove notification only appears when using the terminal which explains why users are running into this issue. Also, update-notifier informs the user another reboot is needed after autoremove is run.
To avoid this mess I’ve commented out the lines of /etc/apt/apt.conf.d/99update-notifier and wrote my own updater using bash and zenity and incorporated needsrestart. It’s not pretty but it works.