This may or may not be an issue, but here are my observations. The order
of operations seems to be the cause of my issue with the additional
factor that the /boot partition size is unusually small compared to
recent Ubuntu installations.

Order of operations as follows:

1. unattended-install script is run
2. removes packages found in /etc/kernel/postinst.d/apt-auto-removal
3. Installs new kernel
4. creates new /etc/kernel/postinst.d/apt-auto-removal

At this point it does not remove any old packages after the new kernel
is installed. However, when unattended-install is run a second time it
will remove those packages. This seems like an awkward approach.
Ideally, the old kernel packages would get removed the first run of
unattended-install. I considered safety concerns in removing older
kernels after an update but then it still gets removed on a second run.
It is also there is a setting here that I overlooked.

I applied a work around in kernel/postinst.d/zzz_autoremove to simply
run apt-get autoremove -y a few seconds after unattended-install is
completed. This approach is not ideal but functional for this
potentially unique issue.

-- 
You received this bug notification because you are a member of Ubuntu
Touch seeded packages, which is subscribed to unattended-upgrades in
Ubuntu.
https://bugs.launchpad.net/bugs/1267059

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

Status in unattended-upgrades package in Ubuntu:
  Fix Released
Status in unattended-upgrades source package in Precise:
  Fix Released
Status in unattended-upgrades source package in Trusty:
  Fix Released

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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