Public bug reported:

So this in not really a bug in the packages reported but in the default 
installation of Ubuntu 14.04 and earlier at least. The boot partition is just 
too small considering that automatic removal of old kernels is not available. 
It's a small repetitive nuisance to me but must be a killer for people who just 
uses Ubuntu and don't run uname -r or df -h /boot. The gui help opens disk 
tools but is useless because it can't even see the kernel files.
Having removed all 3.* kernels it still looks like this, and the problem will 
soon return:
/dev/sda1       236M  109M  115M  49% /boot
This is my desktop but I have witnessed the same problem on Ubuntu server 
installs that otherwise run year after year without trouble, with automatic 
updates and restarts.

ProblemType: Package
DistroRelease: Ubuntu 14.04
Package: linux-image-extra-4.4.0-42-generic 4.4.0-42.62~14.04.1
ProcVersionSignature: Ubuntu 4.4.0-38.57~14.04.1-generic 4.4.19
Uname: Linux 4.4.0-38-generic x86_64
NonfreeKernelModules: nvidia
ApportVersion: 2.14.1-0ubuntu3.21
Architecture: amd64
Date: Tue Oct 11 09:24:09 2016
ErrorMessage: subprocess installed post-installation script returned error exit 
status 1
InstallationDate: Installed on 2015-04-23 (536 days ago)
InstallationMedia: Ubuntu 14.04.2 LTS "Trusty Tahr" - Release amd64 (20150218.1)
RelatedPackageVersions:
 dpkg 1.17.5ubuntu5.7
 apt  1.0.1ubuntu2.14
SourcePackage: linux-lts-xenial
Title: package linux-image-extra-4.4.0-42-generic 4.4.0-42.62~14.04.1 failed to 
install/upgrade: subprocess installed post-installation script returned error 
exit status 1
UpgradeStatus: No upgrade log present (probably fresh install)

** Affects: linux-lts-xenial (Ubuntu)
     Importance: Undecided
         Status: New


** Tags: amd64 apport-package trusty

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https://bugs.launchpad.net/bugs/1632216

Title:
  I ran out of disk space on /boot while running an update. package
  linux-image-extra-4.4.0-42-generic 4.4.0-42.62~14.04.1 failed to
  install/upgrade: subprocess installed post-installation script
  returned error exit status 1

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