I suspect that this bug is a result of the design of dpkg. Does anybody
know specifically what causes the popups? Is it the installation scripts
in the individual packages?

There is no doubt in my experience that this is a stopper for some
users. Specifically experienced users who've used other platforms and
later tried Ubuntu. As an experienced Linux user I'm just glad to be
able to upgrade, although honestly I've yelled at my computer over this
one after walking away to let an upgrade run, only to come back and find
that it's stopped and waiting for input several hours from completion.

What it comes down to is that this issue requires the user to attend the
upgrade which can sometimes take 10-12 hours, and which clearly should
not require periodic user input. So from an HCI standpoint it's
extremely bad behavior. And while I realize the difficulty in bringing
together thousands of separate package scripts into a coherent user
interface, I think this bug really deserves much more developer
attention than it seems to have gotten.

PS - It's definitely a major paper cut.

-- 
RFE: ask all config-file questions at the start or end of the upgrade
https://bugs.launchpad.net/bugs/86028
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