This matches https://github.com/systemd/systemd/issues/3421 very closely
(I've worked on this a bit, but it got stalled, sorry). I think that is
the exact symptom you are seeing, can you confirm?

** Bug watch added: github.com/systemd/systemd/issues #3421
   https://github.com/systemd/systemd/issues/3421

** Also affects: systemd via
   https://github.com/systemd/systemd/issues/3421
   Importance: Unknown
       Status: Unknown

** Changed in: systemd (Ubuntu)
       Status: New => Incomplete

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https://bugs.launchpad.net/bugs/1624317

Title:
  systemd-resolved breaks VPN with split-horizon DNS

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