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

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