I am seeing something similar on 20.04.  If my network fails and I have
any network filesystems mounted (including nfs3 or nfs4 via autofs or
iSCSI via fstab) when I issue a shutdown or reboot command, then I am
likely to have a 10+ minute delay after the console displays that it has
reached target shutdown.  The console will then cycle through displaying
information about each filesystem, such as the fact that the system is
trying to unmount it, the unmount failed, and it is now forcibly killing
processes.  While I have not looked at the source, the timing of the
console messages would imply that the process to unmount filesystems and
kill processes is single-threaded, as there is a significant delay as it
goes through this process with each filesystem.  After it has cycled
through all filesystems, it then slowly cycles through each filesystem
again.  Unfortunately, the logging system has already shut down by the
time any of this happens, so I have no logs in journald or syslog to
submit in relationship to this issue.

Can the process be fixed to only cycle through each filesystem once, and
also to attempt to do multiple filesystems simultaneously so that, at
worst, I only have to wait through one timeout cycle?  I could possibly
see a reason that you might need to wait the timeout multiple times in
the event of nested remote filesystems (e.g. if every level of
/dont/try/this/at/home was a different filesystem on non-local disk),
but that is not the configuration that I have.

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https://bugs.launchpad.net/bugs/1932525

Title:
  This bug is back on my pc -  bug #1722481  Systemd Sync twice at
  shutdown

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