I did some additional tests and reinstalling openssh-server does not break it. It only breaks after the update procedure.
To recreate the error, take a fresh OpenVZ 6 Templates of Ubuntu 16.04 64bit, and simply do: apt-get clean && apt-get autoclean && apt-get autoremove && apt-get update && apt-get upgrade && apt-get dist-upgrade && reboot Maybe there is some other package than openssh-server that breaks things down. Here is some of the output of update procedure: Setting up systemd (229-4ubuntu21.15) ... addgroup: The group `systemd-journal' already exists as a system group. Exiting. [/usr/lib/tmpfiles.d/var.conf:14] Duplicate line for path "/var/log", ignoring. Failed to openat(/dev/simfs): Operation not permitted Failed to validate path /var/run/screen: Too many levels of symbolic links Failed to validate path /var/run/sshd: Too many levels of symbolic links Failed to validate path /var/run/sudo: Too many levels of symbolic links Failed to validate path /var/run/sudo/ts: Too many levels of symbolic links ... Unpacking openssh-server (1:7.2p2-4ubuntu2.6) over (1:7.2p2-4ubuntu2.1) ... Preparing to unpack .../openssh-client_1%3a7.2p2-4ubuntu2.6_amd64.deb ... ... Setting up openssh-server (1:7.2p2-4ubuntu2.6) ... locale: Cannot set LC_CTYPE to default locale: No such file or directory locale: Cannot set LC_MESSAGES to default locale: No such file or directory locale: Cannot set LC_ALL to default locale: No such file or directory Failed to validate path /var/run/sshd: Too many levels of symbolic links -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to Ubuntu. https://bugs.launchpad.net/bugs/1814124 Title: sshd does not start after update To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/openssh/+bug/1814124/+subscriptions -- ubuntu-bugs mailing list ubuntu-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs