In my tests u-u successfully removed the kernels as new unused packages
even when hitting LP: #1803749 for the record.

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https://bugs.launchpad.net/bugs/1803587

Title:
  Update-manager does not remove autoremovable kernel packages
  _before_installing new (kernel) packages

Status in unattended-upgrades package in Ubuntu:
  Invalid
Status in update-manager package in Ubuntu:
  Triaged

Bug description:
  I happened to run apt manually on my system this morning to remove a
  package, and I was informed:

  The following packages were automatically installed and are no longer 
required:
    linux-image-4.15.0-36-generic linux-modules-4.15.0-36-generic
    linux-modules-extra-4.15.0-36-generic

  This was surprising, since I have run update-manager yesterday (with
  no intervening reboot), and unattended-upgrades is enabled, and both
  of those packages should have already removed this stale kernel before
  now.

  After apt autoremove, my current installed packages are:

  $ dpkg -l linux-image'*' | grep ^ii
  ii  linux-image-4.18.0-10-generic          4.18.0-10.11 amd64        Signed 
kernel image generic
  ii  linux-image-4.18.0-11-generic          4.18.0-11.12 amd64        Signed 
kernel image generic
  ii  linux-image-generic                    4.18.0.11.12 amd64        Generic 
Linux kernel image
  $

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