I believe this can be reproduced by:

 - installing grub
 - changing one or more of the settings in /etc/default/grub that are managed 
by debconf (GRUB_CMDLINE_LINUX, GRUB_CMDLINE_LINUX_DEFAULT, GRUB_TIMEOUT, 
GRUB_HIDDEN_TIMEOUT), and *also* changing one or more line in /etc/default/grub 
that is *not* managed by debconf
 - upgrading grub

I haven't seen the /etc/default/grub from the cloud image yet.  Can
someone attach a copy of the file for comparison?

And as to upgrading without a prompt, the correct workaround would be to
set DEBIAN_FRONTEND=noninteractive in the environment, to suppress all
debconf prompting.

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https://bugs.launchpad.net/bugs/1009294

Title:
  Grub update breaks automated dist-upgrade scripts on AMI images

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