Still happening. I noticed that running apt-get autoremove usually
clears up enough old kernel versions to fix this, but it didn't work
this time.

Surely the updater can be configured to run autoremove and prompt the
user yes/no before attempting to install updates? That may fix the issue
in a large number of cases; then it would just be a matter of figuring
out what is marking some kernel versions as still in use so they're not
caught by autoremove.

Also, a larger /boot would still be a good idea.

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https://bugs.launchpad.net/bugs/1183692

Title:
  Not enough disk space for kernel security update on /boot

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