Hello, I've looked more into this.

Upstream does admit that shutdown/reboot commands via systemd may fail.
And the recommendation there is to progressively use bigger hammers.

See: https://github.com/systemd/systemd/issues/3282

So i believe you should be trying to:

$ systemctl poweroff
$ systemctl -f poweroff
$ systemctl -ff poweroff

(or reboot, or whatever the comamnd you need/want)

Specifically, with upgrade from upstart to systemd, and re-exec, we may
not shutdown cleanly, and that should be ok.

** Bug watch added: github.com/systemd/systemd/issues #3282
   https://github.com/systemd/systemd/issues/3282

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

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

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Title:
  Landscape: Upgrade 14.04.5 to 16.04.2 fails unable to reboot

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