This traces to a bug in the kernel-helper command, called from the grub
postinst: it redirects stdout from update-grub to /dev/null, which
breaks launching the debconf interface but keeps it running indefinitely
waiting for user interaction.

I understand that the kernel-helper command is going to be disabled for
intrepid in any case, but I'll fix this bug all the same.

** Changed in: grub (Ubuntu)
       Status: Triaged => In Progress

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update-manager bailed out half-way
https://bugs.launchpad.net/bugs/277506
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