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 -- You received this bug notification because you are a member of Ubuntu Desktop Bugs, which is subscribed to systemd in Ubuntu. https://bugs.launchpad.net/bugs/1624317 Title: systemd-resolved breaks VPN with split-horizon DNS To manage notifications about this bug go to: https://bugs.launchpad.net/systemd/+bug/1624317/+subscriptions -- desktop-bugs mailing list desktop-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/desktop-bugs
