Thanks for the report, and congratulations on figuring out what was
going on! I can see why the behaviour is as described on a very shallow
level: xenial postrm masks both the service and socket units but the
bionic postinst just unmasks the socket. Deeper than that, I really
don't know. The way the service file is installed is different on
xenial, it's installed via the .install file and maybe that makes
dh_systemd do something different. Perhaps the pragmatic fix is to just
explicitly insert "deb-systemd-helper unmask docker.service >/dev/null
|| true" into the postinst in bionic+?

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https://bugs.launchpad.net/bugs/1844894

Title:
  docker doesn’t start in bionic (Unit docker.service is masked), if
  previously installed+removed in xenial

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