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I have a 16.04 server that is updating the /boot/grub/menu.lst file, but not the /boot/grub/grub.cfg file when I upgrade kernels and consequently, at boot it is using the old information in grub.cfg. How do I fix this?

I think some of this might also been the result of a full /boot partition that went unnoticed for a few days when grub installs were happening.

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Check if grub-legacy or grub-legacy-ec2 managed to get installed at some point. If they did, they are updating the old config menu.lst, but your boot sector is starting up grub2 and looking at grub.cfg for it's list.

To fix this, simply reinstall grub2:

sudo apt-get install grub2
sudo update-grub

Then ls -l /boot/grub/grub.cfg should show a modified date of today.

Test a reboot during an appropriate maintenance window to assure it is still functioning properly.

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