This isn't a gdm3 bug, right?

If it's a systemd or systemd unit problem and it's still happening, we
probably need to provide some more information so that xnox or someone
can help and take a look. I tried and just booting a live session in a
VM and shutting it down works for me.

Can someone give clear reproduction steps, preferably for making this
happen in a VM?

If it only happens for some people for some reason, maybe an affected
person can get a journal log for this bug report:
https://freedesktop.org/wiki/Software/systemd/Debugging/#index2h1 -
although it'll be a bit harder to get it out of the live session it
should be possible e.g. to mount a hard drive or a USB key or a 9p
shared volume using virt-manager (hopefully that last one works at late
shutdown).

** Changed in: gdm3 (Ubuntu Bionic)
       Status: Confirmed => Incomplete

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https://bugs.launchpad.net/bugs/1706939

Title:
  A live session can't be shut down due to "[ ***  ] (2 of 2) A start
  job is running for ... (21s / no limit)"

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