Comment 39 for bug 1848797

A number of upgrade issues were addressed in grub2 2.04-1ubuntu26.4 in 20.04, which was released back in September. I am going to mark this as a duplicate of bug #1891680.

However, where the grub debconf state on a system is /wrong/, it is not possible to guard against this failure on reboot because the running system cannot know which disk, which is not listed in the debconf state, has the out-of-date first-stage bootloader.

If you are running an official Ubuntu image in Azure, it should definitely be in a state that the debconf values are NOT wrong. Please open a separate bug report for this and drop a reference to that bug here.