I'm experiencing the same problem with Ubuntu 16.04.5 on OpenVZ (with kernel: 2.6.32-042stab127.2).
The workaround that I found is to edit `/usr/lib/tmpfiles.d/sshd.conf` in the following way: d /run/sshd 0755 root root Here is the question on askubuntu.com, where my case decribed in more details: https://askubuntu.com/q/1109934/566421 -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to Ubuntu. https://bugs.launchpad.net/bugs/1811580 Title: systemd fails to start sshd at reboot To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/systemd/+bug/1811580/+subscriptions -- ubuntu-bugs mailing list ubuntu-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs