bug # 1515513 is a contributing factor.  DKMS has been patched upstream
for that particular bug.  Not sure when Ubuntu will update or
incorporate the patch into their packaged version of dkms.

Are there any other files left behind after kernel updates that might
cause these kinds of update problems?  Are there different circumstances
in which a file may or may not be deleted?

It affects every install that uses dkms and updates kernels in the long
run.

This doesn't put any Linux distribution in a favorable light.

This bug eventually leaves the system in an insecure, unstable state.

And this has been happening since at least 2012 (that's when I first
noticed updates failing due to lack of space in /boot).  As others have
stated, it is impossible to resolve manually for those who are not
technical and just want to use the desktop.  My father has actually had
this happen on the Ubuntu install I set up for him.

I agree. I think it should be handled as a security issue with a higher
priority.

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https://bugs.launchpad.net/bugs/1037285

Title:
  /boot fills up after many kernel upgrades

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