As outlined by Steve in comment #7, the fix for this is in the cloud image 
building tools to add:
  DEBIAN_FRONTEND=noninteractive dpkg-reconfigure grub-pc

A suitable validation of this is to run a instance pre-grub2 update, run
this command, then upgrade.  If it doesn't prompt, then we should have a
suitable resolution.

However, this resolution will not resolve currently deployed AMI's
before this is resolved, only latest builds.  ~smoser is assigned to
land this fix in the build tools for newer AMI's.

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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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