I upgraded my Ubuntu droplet to version 14 however my kernel version was still running 3.11.0-12-generic instead of 3.13.0-34-generic. Thinking that maybe the GRUB update didn’t work in the upgrade I used the web VNC functionality to see if there was a boot menu where I could reconfigure GRUB.

Rebooting the droplet gave me no menu so it seemed there was nothing I could do during boot.

After some hunting I change the following in the /etc/default/grub to try to enable the menu:

#GRUB_HIDDEN_TIMEOUT=0
GRUB_HIDDEN_TIMEOUT_QUIET=true
GRUB_TIMEOUT=2

to

#GRUB_HIDDEN_TIMEOUT=0
#GRUB_HIDDEN_TIMEOUT_QUIET=true
GRUB_TIMEOUT=4

Then ran sudo update-grub and sudo grub-editenv create then rebooted this didn’t help.

It turns out I just wasn’t reading Digital Ocean’s web page right. Once I’d upgraded I needed to go to my droplet’s Control Panel > Settings > Kernel. The choose the correct version and kernel from the drop down list and click Change.

This is the bit I wasn’t doing…. I had to then Power Off the Droplet rather than reboot. Upon the next power on the correct kernel would be loaded.