Comment 0 for bug 1615381

This may happen, if you boot one of the older kernels, that is not protected by /etc/apt/apt.conf.d/01autoremove-kernels

Workaround: run
/etc/kernel/postinst.d/&apt-auto-removal
during each boot (e.g. by using cron).

In shell:

$ uname -r
4.4.0-22-generic
$ apt-get -s autoremove
NOTE: This is only a simulation!
      apt-get needs root privileges for real execution.
      Keep also in mind that locking is deactivated,
      so don't depend on the relevance to the real current situation!
Reading package lists... Done
Building dependency tree
Reading state information... Done
The following packages will be REMOVED:
  linux-headers-4.4.0-21 linux-headers-4.4.0-21-generic linux-headers-4.4.0-22
  linux-headers-4.4.0-22-generic linux-headers-4.4.0-31-generic
  linux-image-4.4.0-21-generic linux-image-4.4.0-22-generic
  linux-image-4.4.0-31-generic linux-image-extra-4.4.0-21-generic
  linux-image-extra-4.4.0-22-generic linux-image-extra-4.4.0-31-generic
0 upgraded, 0 newly installed, 11 to remove and 13 not upgraded.

ProblemType: Bug
DistroRelease: Ubuntu 16.04
Package: apt 1.2.12~ubuntu16.04.1
ProcVersionSignature: Ubuntu 4.4.0-22.40-generic 4.4.8
Uname: Linux 4.4.0-22-generic x86_64
ApportVersion: 2.20.1-0ubuntu2.1
Architecture: amd64
CurrentDesktop: XFCE
Date: Sun Aug 21 16:11:27 2016
EcryptfsInUse: Yes
InstallationDate: Installed on 2016-04-28 (114 days ago)
InstallationMedia: Xubuntu 16.04 LTS "Xenial Xerus" - Release amd64 (20160420.1)
SourcePackage: apt
UpgradeStatus: No upgrade log present (probably fresh install)
modified.conffile..etc.kernel.postinst.d.apt-auto-removal: [modified]
mtime.conffile..etc.kernel.postinst.d.apt-auto-removal: 2016-07-30T12:15:32.706300