Comment 8 for bug 1460396

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Jarno Suni (jarnos) wrote : Re: Software Updater does not guide user to remove old kernels when /boot is about to get full, causing failed updates

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