I found the description somewhat confusing because 'Unattended-Upgrade
::Remove-New-Unused-Dependencies "true"; doesn't actually exist in
/etc/apt/apt.conf.d/50unattended-upgrades, rather that's the default
setting in unattended-upgrades since 0.90. Regardless, I was able to
recreate the issue on an Ubuntu 16.04 system via the following
procedure.

1) Use apt-get install to install a new kernel (linux-image-generic)
2) Run unattended-upgrades (observe "no pending auto-removals")

However, running 'sudo apt autoremove' does want to remove an old
kernel.

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https://bugs.launchpad.net/bugs/1624644

Title:
  By default settings unattended-upgrade is unable to automatically
  remove packages that become unused in conjunction with updating by
  other software.

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