Very strange. Surprisingly, the simple re-installation did do the trick. Luckily, `openssh-server' package doesn't have any hard dependencies to the essential distro meta packages.
Well, originally, I was going to lock the version from `security' repo but first I would have to remove the package anyway, so: $ sudo apt-get remove openssh-server Reading package lists... Done Building dependency tree Reading state information... Done The following packages were automatically installed and are no longer required: libssl1.0.0:i386 openssh-sftp-server Use 'sudo apt autoremove' to remove them. The following packages will be REMOVED: openssh-server 0 upgraded, 0 newly installed, 1 to remove and 0 not upgraded. 1 not fully installed or removed. After this operation, 904 kB disk space will be freed. Do you want to continue? [Y/n] Y (Reading database ... 357805 files and directories currently installed.) Removing openssh-server (1:7.2p2-4ubuntu2.9) ... Processing triggers for man-db (2.7.5-1) ... $ sudo apt-get -y autoremove Reading package lists... Done Building dependency tree Reading state information... Done The following packages will be REMOVED: libssl1.0.0:i386 openssh-sftp-server 0 upgraded, 0 newly installed, 2 to remove and 0 not upgraded. After this operation, 3,223 kB disk space will be freed. (Reading database ... 357792 files and directories currently installed.) Removing libssl1.0.0:i386 (1.0.2g-1ubuntu4.15) ... Removing openssh-sftp-server (1:7.2p2-4ubuntu2.9) ... Processing triggers for libc-bin (2.23-0ubuntu11) ... Processing triggers for man-db (2.7.5-1) ... $ sudo apt-get install openssh-server Reading package lists... Done Building dependency tree Reading state information... Done The following additional packages will be installed: openssh-sftp-server Suggested packages: ssh-askpass rssh molly-guard monkeysphere Recommended packages: ncurses-term ssh-import-id The following NEW packages will be installed: openssh-server openssh-sftp-server 0 upgraded, 2 newly installed, 0 to remove and 0 not upgraded. Need to get 0 B/374 kB of archives. After this operation, 1,013 kB of additional disk space will be used. Do you want to continue? [Y/n] Y Preconfiguring packages ... Selecting previously unselected package openssh-sftp-server. (Reading database ... 357773 files and directories currently installed.) Preparing to unpack .../openssh-sftp-server_1%3a7.2p2-4ubuntu2.9_amd64.deb ... Unpacking openssh-sftp-server (1:7.2p2-4ubuntu2.9) ... Selecting previously unselected package openssh-server. Preparing to unpack .../openssh-server_1%3a7.2p2-4ubuntu2.9_amd64.deb ... Unpacking openssh-server (1:7.2p2-4ubuntu2.9) ... Processing triggers for man-db (2.7.5-1) ... Processing triggers for ureadahead (0.100.0-19.1) ... ureadahead will be reprofiled on next reboot Processing triggers for ufw (0.35-0ubuntu2) ... Processing triggers for systemd (229-4ubuntu21.27) ... Setting up openssh-sftp-server (1:7.2p2-4ubuntu2.9) ... Setting up openssh-server (1:7.2p2-4ubuntu2.9) ... $ sudo systemctl status sshd.service ● ssh.service - OpenBSD Secure Shell server Loaded: loaded (/lib/systemd/system/ssh.service; enabled; vendor preset: enabled) Active: active (running) since Thu 2020-04-23 18:07:13 MSK; 13s ago Process: 27871 ExecStartPre=/usr/sbin/sshd -t (code=exited, status=0/SUCCESS) Main PID: 27874 (sshd) CGroup: /system.slice/ssh.service ├─ 9759 sshd: ia [priv] ├─ 9771 sshd: ia@pts/18 ├─ 9772 -zsh └─27874 /usr/sbin/sshd -D Apr 23 18:07:13 asrockZ97e systemd[1]: Starting OpenBSD Secure Shell server... Apr 23 18:07:13 asrockZ97e sshd[27874]: Server listening on 0.0.0.0 port 22. Apr 23 18:07:13 asrockZ97e sshd[27874]: Server listening on :: port 22. Apr 23 18:07:13 asrockZ97e systemd[1]: Started OpenBSD Secure Shell server. $ ** Changed in: openssh (Ubuntu) Status: New => Invalid -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to Ubuntu. https://bugs.launchpad.net/bugs/1874455 Title: ssh daemon doesn't report successful start state to systemd after upgrade to 1:7.2p2-4ubuntu2.9 To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/openssh/+bug/1874455/+subscriptions -- ubuntu-bugs mailing list ubuntu-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs