In 14.04 there is a dialog that appears informing you should free space
on /boot, if there is too little free space, when using Software
Updater. Not sure, if it works on later releases.

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https://bugs.launchpad.net/bugs/1460396

Title:
  Software Updater does not guide user to remove old kernels when /boot
  is about to get full, causing failed updates

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