This might be aggravated by this DKMS bug which was found in v2.2.0.3,
which incidentally is used in Ubuntu 16.04 LTS, and maybe other
versions.  It doesn't remove old initrd files in /boot *which lead to
full /boot issues and subsequent update problems*

I manually removed a bunch of old initrd images the other day.

http://askubuntu.com/questions/616512/purging-old-kernels-fails-to-
remove-old-initrd-files

https://bugs.debian.org/cgi-bin/bugreport.cgi?bug=717584

** Bug watch added: Debian Bug tracker #717584
   http://bugs.debian.org/cgi-bin/bugreport.cgi?bug=717584

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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

Status in unattended-upgrades:
  New
Status in unattended-upgrades package in Ubuntu:
  Fix Released

Bug description:
  Currently if one chooses to use LVM or encrypted install, a /boot
  partition is created of 236Mb

  Once kernel updates start being released this partition soon fills
  until people are left unable to upgrade.

  While you and I might know that we need to watch partition space, many
  of the people we have installing think that a windows disk is a disk
  and not a partition, education is probably the key - but in the
  meantime support venues keep needing to deal with the fact the
  partition is too small and/or old kernels are not purged as new ones
  install.

  For workaround and sytem repair, see
  https://help.ubuntu.com/community/Lubuntu/Documentation/RemoveOldKernels

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