That it is not new installs but old ones that fail to upgrade properly
is intriguing. Let's get to the bottom of this!

> Is there any way I can force apt or dpkg to install it

If you mean "... to install it (resolvconf) properly" then the answer is
that you do "dpkg-reconfigure resolvconf" after upgrade.

> nothing has broken for us besides that apt-get dist-upgrade fails on
resolvconf

Can you please post the error message and an exact description of the
symptoms of the failure?

Also, on some machine where you have reproduced the problem, run
"apport-collect 1000244"; and make sure you include (the relevant part
of) /var/log/apt/term.log.

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https://bugs.launchpad.net/bugs/1000244

Title:
  Symlink /etc/resolv.conf does not exist after installation or upgrade
  of resolvconf -- various causes

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