I agree with @Jamiejellicoe this ticket should be rated as "Security
issue" (250) but we are close that (236)...

Having /boot full can lead to kernel, inird image or grub.conf corruption and 
on top of that it's blocking new security updates to be applied.

When /boot is full you cannot even purge old kernel before /boot has a minimum
disk space. So my workaround is to echo -n > /boot/initrd.img- some old 
kernel's inird images
so I have enough free space to cleanup old kernel, header, etc.

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https://bugs.launchpad.net/bugs/1267059

Title:
  "Unattended-Upgrade::Remove-Unused-Dependencies" does not work

Status in unattended-upgrades package in Ubuntu:
  Triaged

Bug description:
  I have a system that runs unattended-upgrades just fine. Now i want to
  automate removal of old kernels and kernel header packages that are
  accumulating otherwise. So i set 'Unattended-Upgrade::Remove-Unused-
  Dependencies "true";'. But it doesn't work.

  ----
  Details: Lots of stuff pending autoremoval:

  $ apt-get --assume-no autoremove 
  Reading package lists... Done
  Building dependency tree       
  Reading state information... Done
  The following packages will be REMOVED
    linux-headers-3.2.0-38 linux-headers-3.2.0-38-generic 
linux-headers-3.2.0-39 linux-headers-3.2.0-39-generic linux-headers-3.2.0-40 
linux-headers-3.2.0-40-generic linux-headers-3.2.0-41 
linux-headers-3.2.0-41-generic linux-headers-3.2.0-43 
linux-headers-3.2.0-43-generic linux-headers-3.2.0-44 
linux-headers-3.2.0-44-generic linux-headers-3.2.0-45 
linux-headers-3.2.0-45-generic linux-headers-3.2.0-48 
linux-headers-3.2.0-48-generic linux-headers-3.2.0-51 
linux-headers-3.2.0-51-generic linux-headers-3.2.0-52 
linux-headers-3.2.0-52-generic linux-headers-3.2.0-53 
linux-headers-3.2.0-53-generic linux-headers-3.2.0-54 
linux-headers-3.2.0-54-generic linux-headers-3.2.0-55 
linux-headers-3.2.0-55-generic linux-headers-3.2.0-56 
linux-headers-3.2.0-56-generic linux-image-3.2.0-39-generic 
linux-image-3.2.0-40-generic linux-image-3.2.0-41-generic 
linux-image-3.2.0-43-generic linux-image-3.2.0-44-generic 
linux-image-3.2.0-45-generic linux-image-3.2.0-48-generic 
linux-image-3.2.0-51-generic linux-
 image-3.2.0-52-generic linux-image-3.2.0-53-generic 
linux-image-3.2.0-54-generic linux-image-3.2.0-55-generic 
linux-image-3.2.0-56-generic
  0 upgraded, 0 newly installed, 41 to remove and 13 not upgraded.
  After this operation, 2,893 MB disk space will be freed.
  Do you want to continue [Y/n]? N
  Abort.

  Note that the majority of these packages have been installed by
  unattended-upgrades from precise-security.

  According to the comments within/etc/apt/apt.conf.d/50unattended-
  upgrades, this should automate autoremoval:

    // Do automatic removal of new unused dependencies after the upgrade
    // (equivalent to apt-get autoremove)
    Unattended-Upgrade::Remove-Unused-Dependencies "true";

  but nothing happens (note the line "Packages that are auto removed: ''
  ":

  $ unattended-upgrades --debug --dry-run
  Initial blacklisted packages: 
  Starting unattended upgrades script
  Allowed origins are: ['o=Ubuntu,a=precise-security']
  adjusting candidate version: '<Version: package:'accountsservice' 
version:'0.6.15-2ubuntu9.6.1'>'
  adjusting candidate version: '<Version: package:'libaccountsservice0' 
version:'0.6.15-2ubuntu9.6.1'>'
  adjusting candidate version: '<Version: package:'libdrm-intel1' 
version:'2.4.43-0ubuntu0.0.3'>'
  adjusting candidate version: '<Version: package:'libdrm-nouveau1a' 
version:'2.4.43-0ubuntu0.0.3'>'
  adjusting candidate version: '<Version: package:'libdrm-radeon1' 
version:'2.4.43-0ubuntu0.0.3'>'
  adjusting candidate version: '<Version: package:'libdrm2' 
version:'2.4.43-0ubuntu0.0.3'>'
  Checking: bc (["<Origin component:'main' archive:'precise-updates' 
origin:'Ubuntu' label:'Ubuntu' site:'gb.archive.ubuntu.com' isTrusted:True>"])
  Checking: grub-common (["<Origin component:'main' archive:'precise-updates' 
origin:'Ubuntu' label:'Ubuntu' site:'gb.archive.ubuntu.com' isTrusted:True>"])
  Checking: grub-pc (["<Origin component:'main' archive:'precise-updates' 
origin:'Ubuntu' label:'Ubuntu' site:'gb.archive.ubuntu.com' isTrusted:True>"])
  Checking: grub-pc-bin (["<Origin component:'main' archive:'precise-updates' 
origin:'Ubuntu' label:'Ubuntu' site:'gb.archive.ubuntu.com' isTrusted:True>"])
  Checking: grub2-common (["<Origin component:'main' archive:'precise-updates' 
origin:'Ubuntu' label:'Ubuntu' site:'gb.archive.ubuntu.com' isTrusted:True>"])
  Checking: iproute (["<Origin component:'main' archive:'precise-updates' 
origin:'Ubuntu' label:'Ubuntu' site:'gb.archive.ubuntu.com' isTrusted:True>"])
  Checking: landscape-common (["<Origin component:'main' 
archive:'precise-updates' origin:'Ubuntu' label:'Ubuntu' 
site:'gb.archive.ubuntu.com' isTrusted:True>"])
  pkgs that look like they should be upgraded: 
  Fetched 0 B in 0s (0 B/s)                                                     
                                                                                
                 
  blacklist: []
  Packages that are auto removed: ''
  InstCount=0 DelCount=0 BrokenCout=0
  No packages found that can be upgraded unattended

  
  ----
  I am using unattended-upgrades-0.76ubuntu1 on Ubuntu 12.04.3 LTS

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