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.

cd /boot

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  &&  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.

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