This link shows what kind of dialog there is: 
http://elementaryos.stackexchange.com/q/1634
The issue is that the dialog tells to empty trash and use 'sudo apt-get clean' 
which may help only, if /boot is on same partition than some of the files in 
trash, the /var/cache/apt/archives/ or /var/cache/apt/archives/partial/.

In Ubuntu 16.04 and later a more helpful advise would be to run "sudo
apt-get autoremove --purge". (That might not do the trick in 14.04 due
to Bug #1439769)

For more control on which kernels to purge, this utility would be
useful: https://www.bountysource.com/issues/38300038-feature-request-
the-command-should-work-like-this

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

Title:
  Software Updater does not guide user to remove excessive kernels when
  there is too little space on /boot to install a kernel update.

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