Christian, my reproduction steps were wrong, "do-release-upgrade
--proposed" in a Trusty container won't work because this will only pull
the upgrader from xenial-proposed and not pptpd. As such, there is no
easy way to do a test release upgrade but you can fix a broken upgrade
by installing 1.4.0-7ubuntu0.2 from xenial-proposed. Lastly, the
unauthenticated warning from your Trusty container seems to be
unrelated, try refreshing your indexes (apt-get update) and see if that
helps.

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https://bugs.launchpad.net/bugs/1610500

Title:
  package pptpd 1.4.0-7ubuntu0.1 failed to install/upgrade: subprocess
  installed post-installation script returned error exit status 1

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