Hi Jamie, Please also provide the contents of /var/lib/ucf/cache/\:var\:run\:grub\:menu.lst .
What is your DEBIAN_FRONTEND set to when you invoke update-grub?
** Changed in: grub (Ubuntu)
Status: New => Incomplete
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update-grub not updating menu.lst
https://bugs.launchpad.net/bugs/202009
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