I have seen such errors related to OpenVZ 6 - you can take a look at bug 1814124 and bug 1811580 for that if it applies to you.
If that is true check for the workarounds in those buge for a short term resolution, long term you should ask your provider to update your hosting environment. If your case is this one please mark this bug here as a dup of it as well. If the above does not apply please outline your environment in detail as reproducing this locally for me neither triggers in containers nor in VMs. ** Changed in: openssh (Ubuntu) Status: New => Incomplete ** Tags added: server-triage-discuss -- You received this bug notification because you are a member of Ubuntu Touch seeded packages, which is subscribed to openssh in Ubuntu. https://bugs.launchpad.net/bugs/1823474 Title: package openssh-server 1:7.2p2-4ubuntu2.8 failed to install/upgrade: subprocess installed post-installation script returned error exit status 1 Status in openssh package in Ubuntu: Incomplete Bug description: frequently fails; Devon:~$ systemctl status ssh * ssh.service - OpenBSD Secure Shell server Loaded: loaded (/lib/systemd/system/ssh.service; enabled; vendor preset: enabled) Active: failed (Result: start-limit-hit) since Sa 2019-04-06 17:42:35 CEST; 5min ago Process: 15706 ExecStartPre=/usr/sbin/sshd -t (code=exited, status=255) ProblemType: Package DistroRelease: Ubuntu 16.04 Package: openssh-server 1:7.2p2-4ubuntu2.8 ProcVersionSignature: Ubuntu 4.15.0-46.49~16.04.1-generic 4.15.18 Uname: Linux 4.15.0-46-generic x86_64 ApportVersion: 2.20.1-0ubuntu2.18 Architecture: amd64 Date: Sat Apr 6 11:17:53 2019 ErrorMessage: subprocess installed post-installation script returned error exit status 1 InstallationDate: Installed on 2018-12-08 (119 days ago) InstallationMedia: Ubuntu 16.04.3 LTS "Xenial Xerus" - Release amd64 (20170801) RelatedPackageVersions: dpkg 1.18.4ubuntu1.5 apt 1.2.31 SSHDConfig: Error: command ['/usr/sbin/sshd', '-T'] failed with exit code 255: Missing privilege separation directory: /var/run/sshd SourcePackage: openssh Title: package openssh-server 1:7.2p2-4ubuntu2.8 failed to install/upgrade: subprocess installed post-installation script returned error exit status 1 UpgradeStatus: No upgrade log present (probably fresh install) To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/openssh/+bug/1823474/+subscriptions -- Mailing list: https://launchpad.net/~touch-packages Post to : touch-packages@lists.launchpad.net Unsubscribe : https://launchpad.net/~touch-packages More help : https://help.launchpad.net/ListHelp