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. ** Attachment added: "Screenshots debug shell and shutdown messages" https://bugs.launchpad.net/ubuntu/+source/systemd/+bug/1554795/+attachment/4861267/+files/no-reboot-with-unattended-upgrades.png -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to Ubuntu. https://bugs.launchpad.net/bugs/1554795 Title: timeout on restart or shutdown with LUKS root To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/initramfs-tools/+bug/1554795/+subscriptions -- ubuntu-bugs mailing list ubuntu-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs
