Might be a good idea to enable some systemd parameter for debugging
purposes : https://freedesktop.org/wiki/Software/systemd/Debugging/

Enabling tty9 w/ systemd.debug-shell=1

and possibly the following :

Diagnosing Shutdown Problems
Just like with boot problems, when you encounter a hang during shutting down, 
make sure you wait at least 5 minutes to distinguish a permanent hang from a 
broken service that's just timing out. Then it's worth testing whether the 
system reacts to CTRL+ALT+DEL in any way.

If shutdown (whether it be to reboot or power-off) of your system gets
stuck, first test if the kernel itself is able to reboot or power-off
the machine forcedly using one of these commands:

reboot -f
poweroff -f
If either one of the commands does not work, it's more likely to be a kernel, 
not systemd bug.

Shutdown Completes Eventually
If normal reboot or poweroff work, but take a suspiciously long time, then

boot with the debug options:

systemd.log_level=debug systemd.log_target=kmsg log_buf_len=1M 
printk.devkmsg=on enforcing=0
save the following script as /usr/lib/systemd/system-shutdown/debug.sh and make 
it executable:

#!/bin/sh
mount -o remount,rw /
dmesg > /shutdown-log.txt
mount -o remount,ro /
reboot

Look for timeouts logged in the resulting file shutdown-log.txt and/or
attach it to a bugreport.

Shutdown Never Finishes
If normal reboot or poweroff never finish even after waiting a few minutes, the 
above method to create the shutdown log will not help and the log must be 
obtained using other methods. Two options that are useful for debugging boot 
problems can be used also for shutdown problems:

use a serial console
use a debug shell - not only is it available from early boot, it also stays 
active until late shutdown.

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You received this bug notification because you are a member of Ubuntu
Bugs, which is subscribed to Ubuntu.
https://bugs.launchpad.net/bugs/1796376

Title:
  Bug #1739107 fix causes linux-cloud-tools-common not to be upgradable
  with unattended-upgrades on shutdown mode

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