I had the same issue, too...
Lots of messages saying "Timed out stoppping ...".
The system never rebooted.
Here is what fixed the problem for me:
Firstly, I activated systemd's debug shell using 'systemctl enable debug-shell.service'.
Then I initiated a reboot and when the problem occured, I switched to debug shell (alt+F9 [/F10 ?] ).
Using 'systemctl list-jobs', I figured out what jobs were running while the system hung.
One of the jobs was an "unattended-upgrdes" job.
This job held one ore more files on my root filesystem open.
When I killed that process, the system finished its shutdown and rebooted.
After having removed the package by 'apt-get --purge remove unattended-upgrades' the problem didn't arise again.
I am using cron-apt on my servers - therefore I do not necessarily need unattended-upgrades.
Hopefully this helps as workaround and to find the real cause of the problem.
I had the same issue, too...
Lots of messages saying "Timed out stoppping ...".
The system never rebooted.
Here is what fixed the problem for me:
Firstly, I activated systemd's debug shell using 'systemctl enable debug-shell. service' .
Then I initiated a reboot and when the problem occured, I switched to debug shell (alt+F9 [/F10 ?] ).
Using 'systemctl list-jobs', I figured out what jobs were running while the system hung.
One of the jobs was an "unattended- upgrdes" job.
This job held one ore more files on my root filesystem open.
When I killed that process, the system finished its shutdown and rebooted.
After having removed the package by 'apt-get --purge remove unattended- upgrades' the problem didn't arise again.
I am using cron-apt on my servers - therefore I do not necessarily need unattended- upgrades.
Hopefully this helps as workaround and to find the real cause of the problem.