I've narrowed it down to a specific special character at any location in
the string, and after changing all of my passwords that included it, I
can reveal it to be the '#' character. So either pass#word or password#
fails.

I am now checking other special characters ('*' works).

Is there a faster way of me doing this than spinning up new VMs and
going through the installation each time?

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https://bugs.launchpad.net/bugs/1948714

Title:
  After reboot, the password set at install time doesn't work.

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