Phill,
   Boot with "systemd.debug-shell plymouth:debug" added as kernel params then 
when it hangs switch to VT9. You will probably need to manually remount  a 
partition/usb to get the logs out, since you will be quite late in the shutdown 
cycle.

grab `journalctl` output and /var/log/plymouth-debug.log

I can't reproduce on my laptop, though I did poke around previously in a
VM. vbox was I recall having drm issues, vmware just seemed racy (it
worked maybe 1/5 reboots).

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https://bugs.launchpad.net/bugs/1447038

Title:
  Shutdown/Restart of live session guest does not work in Virtualbox,
  and VMWare

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