It looks like this was fixed upstream and it would be fantastic if this
could make it into Bionic before anything is frozen.
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systemd 237 reports incorrect state when drop-in present
Status in systemd package in Ubuntu:
Raised this upstream:
In short, in systemd 237 as it ships with Bionic, if a unit has a
drop-in present but has been masked, systemctl is-enabled and
systemctl list-unit-files report incorrect state, showing the units as
enabled rather than masked.
This works as-expected in systemd 229 under Xenial. I have not tested
under systemd 234 in artful so I cannot say for sure exactly when this
was introduced, but will spin up a quick test to see if this also
exists under systemd 234.
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