I tried to reproduce the problem on an unpatched Xenial machine but
couldn't as it seems that /usr/lib/ubuntu-release-upgrader/check-new-
release (from comment #10) doesn't use HTTPS to get to
changelogs.ubuntu.com. If someone has clear steps to reproduce on
Xenial, I'll be happy to try it out.

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https://bugs.launchpad.net/bugs/1771914

Title:
  release-upgrade-motd can't update message via apt proxy

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