It would probably be possible to add a "Prompts: always | overwrite |
never" tag to the Debian control file, then process all those that have
it set to never, then unknown, then overwrite, then always.

The sledgehammer approach would be to kill any dpkg -i that prompts and
have the manager continue with the next one when there is a large group.
Then apt-get install will detect the packages as partially installed and
rerun the postinst scripts.

I will make notes, at least if the upgrade ever gets past the
downloading phase...

-- 
too many annoying interruptions during distribution upgrade
https://bugs.launchpad.net/bugs/147928
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