Perhaps we are talking at cross purposes. My expectation is that update
would list the packages to be removed because they are no longer
dependencies of packages that were consciously installed. On that basis,
there should be no surprise to users. The messaging could point users to
a handy document to understand how they can make a package stick around
by flagging it as one they have manually / consciously installed.

My point is that most users don't install
'linux-image-extra-4.13.0-15-generic' themselves, they have a system
with 'linux-image-generic' installed, and it's dependencies change over
time.

AIUI, we already have a good way of holding back from autoremoval
versions of the kernel which are currently in use, or which are the
last-best-guess-good kernel, or which are the next-kernel-to-boot. All
other kernels that were not explicitly installed by the user are simply
ephemeral to that user, and for the vast majority of users, those
ephemeral kernels build up over time taking large amounts of space and
slowing down upgrades thanks to the initramfs generation mechanisms.
Those kernels should go when they are deemed surplus; the user did not
ask for them explicitly, and the user isn't going to boot them either.

Here's what I have in mind, note the changes to text in the output of
apt upgrade. The user is prompted, and told how to avoid autoremoval.

$ sudo apt upgrade
Reading package lists... Done
Building dependency tree      
Reading state information... Done
Calculating upgrade... Done

These packages were automatically installed and are no longer needed:
  libgweather-3-6, linux-image-extra-4.13.0-15-generic
Cancel this operation and use 'sudo apt install <package>' to keep them
from automatic removal.

The following packages have been kept back:
  libreoffice-help-en-us

The following packages will be upgraded:
  libio-socket-ssl-perl

1 upgraded, 0 newly installed, 2 to remove and 1 not upgraded.

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https://bugs.launchpad.net/bugs/1734104

Title:
  'upgrade' in bionic should by default autoremove as well

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