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> Granted, my experience with DEB has mostly been limited to Ubuntu - so it could be that/Canonical.

It is not a Canonical specificity, but it is overridable behavior.

For the dpkg prompting on configuration file changes:

> You can also make those options permanent by creating /etc/apt/apt.conf.d/local:

> Dpkg::Options { > "--force-confdef"; > "--force-confold"; > }

Along with invoking apt with -y (assume yes) will get you close to the behavior you seek. Or as a permanent setting:

APT::Get::Assume-Yes "true";