The reason why 'apt-get autoremove' is stated there is that it is a
simple working way in 16.04 and later for most users, if your system is
not broken already. purge-old-kernels is included in some Ubuntu
package; consequently it is supported by Launchpad's bug reporting
system. But as said in the document, it is currently deprecated and its
bugs will likely not be fixed. It might still be useful for some users
in some cases.

If one wants to use unattended-upgrades manually, he/she could disable
it from being called automatically. One should avoid installing security
updates manually by Software Updater in 14.04, if one expects to use apt
/unattended-upgrades for removing kernels automatically.

I have developed some software that makes the un-clogging part easier;
link to related bountysource.com page is included in the document. Just
feel free to post a bounty and/or give some feedback about the interface
in the respective Launchpad page. I guess the software could be launched
automatically in case of kernel clog when it happens in interactive
session (or even in non-interactive session, if the software is made to
support completely non-interactive un-clogging).

If you install a kernel manually in command line by say
sudo apt-get install linux-image-4.4.0-87-generic
which kernel(s) that command should remove in turn in your opinion? Or could it 
be that the user who runs the command should take care of it? User possibly 
wants to keep some spare kernels, in case the one that is just installed is 
bad. Or a developer may want to keep some testing kernels etc.

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https://bugs.launchpad.net/bugs/1357093

Title:
  Kernels not autoremoving, causing out of space error on LVM or
  Encrypted installation or on any installation, when /boot partition
  gets full

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