Findings from molly-guard removal.  TL;DR it seems to have worked.

Process followed:

Tested it was failing on a shutdown -r now
It failed with same error and drop out to dracut shell

Re-started and ran command: apt purge molly-guard
It did its thing

Did a shutdown -r now
This failed with same error and dropped to dracut shell.

Started again. Noticed there were some updates ready, so applied them
apt-get update
apt-get dist-upgrade

**Note there were no kernel updates ready, BUT it did run the update-
initramfs command to renew the file.

Didn't check to see if the /var/run/reboot-required was there, :( but
did the shutdown -r now and...

It worked!!

Done a couple of restarts with success. So will wait for next auto
unattended-upgrade cycle to prove its really the cause.

Hope that helps.

Jim

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https://bugs.launchpad.net/bugs/2147476

Title:
  dracut Warning: shutdown/reboot failed!

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