Thinking about this, the problem is presumably that the pointed-to apt
config does not have any keys available. This makes me wonder how this
worked with older versions of apt. Perhaps they fell back to the keys in
the base config at /etc/apt? Maybe it was effectively a bug in old apt
that it didn't require any necessary keys to be copied into the new
config.

So, to go back to first principles: If we are trying to install a set of
packages into an empty chroot, what does apt need in the pointed-to
config in order to be satisfied about authentication? Does any tool
doing this need to pre-download the necessary archive keyrings (or
otherwise get the necessary keys) and then run apt-key add using the
pointed-at apt config?

If so why was this not previously necessary?

Is there are simpler workaround in the case where the keys are already
present in the main-system apt installation? Perhaps they could just be
pointed-at with a config option or copied into the new chroot?

Advice most welcome, as all this is currently worked around with a lot
of allowunauthenticaed and --force-yes in the tools, which isn't very
satisfying.

** Branch linked: lp:ubuntu/multistrap

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apt authentication failing when using config in chroot path
https://bugs.launchpad.net/bugs/646499
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