Ian Weisser, I think in 16.04, in contrary to what you claim, packages are not 
autoremoved before doing anything else. 
https://github.com/mvo5/unattended-upgrades tells:
"Unattended-Upgrade::Remove-New-Unused-Dependencies - boolean (default:True)

Remove any new unused dependencies after the upgrade finished."

Anyway, in my 16.04 system, where I have the setting enabled (as
default) and unattended-upgrades enabled (via Software & Updates), I
currently have 6 kernels installed, so I think it is not doing its job
well.

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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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