This started on 16.10 btw.
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systemd-resolved breaks VPN with split-horizon DNS
Status in systemd:
Status in systemd package in Ubuntu:
I use a VPN configured with network-manager-openconnect-gnome in which
a split-horizon DNS setup assigns different addresses to some names
inside the remote network than the addresses seen for those names from
outside the remote network. However, systemd-resolved often decides
to ignore the VPN’s DNS servers and use the local network’s DNS
servers to resolve names (whether in the remote domain or not),
breaking the split-horizon DNS.
This related bug, reported by Lennart Poettering himself, was closed with the
current Fedora release at the time reaching EOL:
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