Public bug reported:

The apt kernel autoremoval handling should by design keep at least 2 and
at most 3 kernels on the system.

However, on my 17.10 system, I currently have 3 kernels marked for
retention while the kernel I have booted is the newest of these.  This
means that I'm not able to upgrade to 18.04 without manual intervention,
because I have a /boot that's sized just large enough to fit 3 kernels,
not 4, apt autoremove won't remove any of the kernels.

The sequence here is that I was running 4.13.0-36-generic; I updated,
which pulled 4.13.0-37-generic onto the system; I ran apt autoremove
--purge, which removed any kernels older than -36- from the system; I
did *not* reboot; I installed 4.13.0-38-generic (from artful-proposed);
all three kernels present are now marked for retention.  I rebooted, and
all three kernels are still marked for retention.

If /etc/kernel/postinst.d/apt-auto-removal were run *now*, it would mark
4.13.0-36-generic as autoremovable.  But there is nothing that reruns
this script on boot.  Maybe there should be?

$ last
vorlon   tty2         :0               Tue Mar 20 11:14   still logged in
reboot   system boot  4.13.0-38-generi Tue Mar 20 10:34   still running
vorlon   tty2         :0               Tue Mar  6 23:12 - down  (13+10:21)
reboot   system boot  4.13.0-36-generi Tue Mar  6 23:10 - 10:33 (13+10:23)

wtmp begins Tue Mar  6 23:09:27 2018
$

ProblemType: Bug
DistroRelease: Ubuntu 17.10
Package: apt 1.5.1
ProcVersionSignature: Ubuntu 4.13.0-38.43-generic 4.13.16
Uname: Linux 4.13.0-38-generic x86_64
NonfreeKernelModules: zfs zunicode zavl zcommon znvpair
ApportVersion: 2.20.7-0ubuntu3.7
Architecture: amd64
CurrentDesktop: ubuntu:GNOME
Date: Wed Mar 21 13:02:43 2018
InstallationDate: Installed on 2010-09-24 (2735 days ago)
InstallationMedia: Ubuntu 10.04.1 LTS "Lucid Lynx" - Release amd64 (20100816.1)
SourcePackage: apt
UpgradeStatus: Upgraded to artful on 2018-03-21 (0 days ago)

** Affects: apt (Ubuntu)
     Importance: Undecided
         Status: New


** Tags: amd64 apport-bug artful

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https://bugs.launchpad.net/bugs/1757529

Title:
  apt: after reboot, still wants to keep 3 kernels when it should only
  keep 2

Status in apt package in Ubuntu:
  New

Bug description:
  The apt kernel autoremoval handling should by design keep at least 2
  and at most 3 kernels on the system.

  However, on my 17.10 system, I currently have 3 kernels marked for
  retention while the kernel I have booted is the newest of these.  This
  means that I'm not able to upgrade to 18.04 without manual
  intervention, because I have a /boot that's sized just large enough to
  fit 3 kernels, not 4, apt autoremove won't remove any of the kernels.

  The sequence here is that I was running 4.13.0-36-generic; I updated,
  which pulled 4.13.0-37-generic onto the system; I ran apt autoremove
  --purge, which removed any kernels older than -36- from the system; I
  did *not* reboot; I installed 4.13.0-38-generic (from artful-
  proposed); all three kernels present are now marked for retention.  I
  rebooted, and all three kernels are still marked for retention.

  If /etc/kernel/postinst.d/apt-auto-removal were run *now*, it would
  mark 4.13.0-36-generic as autoremovable.  But there is nothing that
  reruns this script on boot.  Maybe there should be?

  $ last
  vorlon   tty2         :0               Tue Mar 20 11:14   still logged in
  reboot   system boot  4.13.0-38-generi Tue Mar 20 10:34   still running
  vorlon   tty2         :0               Tue Mar  6 23:12 - down  (13+10:21)
  reboot   system boot  4.13.0-36-generi Tue Mar  6 23:10 - 10:33 (13+10:23)

  wtmp begins Tue Mar  6 23:09:27 2018
  $

  ProblemType: Bug
  DistroRelease: Ubuntu 17.10
  Package: apt 1.5.1
  ProcVersionSignature: Ubuntu 4.13.0-38.43-generic 4.13.16
  Uname: Linux 4.13.0-38-generic x86_64
  NonfreeKernelModules: zfs zunicode zavl zcommon znvpair
  ApportVersion: 2.20.7-0ubuntu3.7
  Architecture: amd64
  CurrentDesktop: ubuntu:GNOME
  Date: Wed Mar 21 13:02:43 2018
  InstallationDate: Installed on 2010-09-24 (2735 days ago)
  InstallationMedia: Ubuntu 10.04.1 LTS "Lucid Lynx" - Release amd64 
(20100816.1)
  SourcePackage: apt
  UpgradeStatus: Upgraded to artful on 2018-03-21 (0 days ago)

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