So I had an issue today in which I kept getting an error message when I attempted to upgrade my ubuntu server, it basically said I was out of disk space, which was odd as I had a 2TB drive as this is a Plex server, after running df -h I quickly noticed that /boot was @ 100% full, so after a quick Google I found the below solution.
If /boot is 100% full you will not be able to just run ‘sudo apt-get autoremove’ you’ll receive a bunch of error messages, so you will have to manually delete some files.
sudo rm abi-4.8.0-53-generic && sudo rm config-4.8.0-53-generic && sudo rm initrd.img-4.8.0-53-generic && sudo rm System.map-4.8.0-53-generic && sudo rm vmlinuz-4.8.0-53-generic
**The above command must be on 1 line or you can use \ to do multi-line in Linux
Do the above for a few versions(DO NOT DELETE ALL VERSIONS) and then you can run either
sudo apt-get -f install or sudo apt-get autoremove
Also you can run the below commands to see all linux-images and headers on your system
sudo dpkg -l | grep linux-image
sudo dpkg -l | grep linux-headers
dpkg -l linux-image-\* | grep ^ii
And you should now be able to upgrade your system again.