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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You received this bug notification because you are a member of Ubuntu
Touch seeded packages, which is subscribed to ubuntu-meta in Ubuntu.
https://bugs.launchpad.net/bugs/1037285

Title:
  /boot fills up after many kernel upgrades

Status in ubuntu-meta package in Ubuntu:
  Confirmed

Bug description:
  THIS ISSUE MAY PREVENT SECURITY UPDATES TO THE KERNEL.

  Obsolete versions of the kernel remain installed on a system, causing a full 
/boot or wasting space on single-partition installations.
  This has the effect that (some) software updates no longer work (at least 
those to the kernel):

  update-initramfs: Generating /boot/initrd.img-3.2.0-29-generic

  gzip: stdout: No space left on device
  [...]
  Errors were encountered while processing:
   initramfs-tools
  E: Sub-process /usr/bin/dpkg returned an error code (1)

  To resolve this, the user must figure out which packages to deinstall.
  A novice user will not know what to do.

To manage notifications about this bug go to:
https://bugs.launchpad.net/ubuntu/+source/ubuntu-meta/+bug/1037285/+subscriptions

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