Ian Weisser, the issue is covered by the title of this bug report,
anyway. If 'Unattended-Upgrade::Remove-Unused-Dependencies "true";' is
used, U-U removes extra kernels, even if new kernels are installed by
Software Updater in 16.04. In 14.04 (and in 12.04 I suppose) it does not
work due to bug Bug #1439769. So running 'apt-get autoremove' in
14.04/12.04 may not have the desired effect. Anyway, the point of this
bug report was that old kernels should be autoremoving so that
administator does not have to be concerned of /boot getting full, so I
think another package should be added as being affected, too.

How does installing kernel header packages (which do normally get
installed anyway) prevent marking kernel packages as 'auto'? I do not
see that happening in 16.04 at least. linux-header packages do not
depend on linux-image packages besides linux-header packages may itself
be marked 'auto'.

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https://bugs.launchpad.net/bugs/1357093

Title:
  Kernels not autoremoving, causing out of space error on LVM or
  Encrypted installation or on any installation, when /boot partition
  gets full

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