I have verified each test case using openssh-server 1:9.0p1-1ubuntu7.1 from kinetic-proposed: Test #1: root@jammy:~# grep "^ListenAddress" /etc/ssh/sshd_config ListenAddress 0.0.0.0:1234 root@jammy:~# systemctl status ssh ● ssh.service - OpenBSD Secure Shell server Loaded: loaded (/lib/systemd/system/ssh.service; enabled; vendor preset: enabled) Drop-In: /run/systemd/system/service.d └─zzz-lxc-service.conf Active: active (running) since Thu 2022-11-03 10:22:04 UTC; 30s ago Docs: man:sshd(8) man:sshd_config(5) Process: 868 ExecStartPre=/usr/sbin/sshd -t (code=exited, status=0/SUCCESS) Main PID: 869 (sshd) Tasks: 1 (limit: 18901) Memory: 1.7M CPU: 19ms CGroup: /system.slice/ssh.service └─869 "sshd: /usr/sbin/sshd -D [listener] 0 of 10-100 startups" Nov 03 10:22:04 jammy systemd[1]: Starting OpenBSD Secure Shell server... Nov 03 10:22:04 jammy sshd[869]: Server listening on 0.0.0.0 port 1234. Nov 03 10:22:04 jammy systemd[1]: Started OpenBSD Secure Shell server. root@jammy:~# vi /etc/apt/sources.list root@jammy:~# cat /etc/apt/sources.list deb http://archive.ubuntu.com/ubuntu kinetic main restricted universe multiverse deb http://archive.ubuntu.com/ubuntu kinetic-updates main restricted universe multiverse deb http://archive.ubuntu.com/ubuntu kinetic-proposed main restricted universe multiverse deb http://security.ubuntu.com/ubuntu kinetic-security main restricted universe multiverse root@jammy:~# apt update && apt dist-upgrade -y [...] root@jammy:~# cat /etc/systemd/system/ssh.socket.d/addresses.conf [Socket] ListenStream= ListenStream=0.0.0.0:1234 root@jammy:~# systemctl status ssh.socket ● ssh.socket - OpenBSD Secure Shell server socket Loaded: loaded (/lib/systemd/system/ssh.socket; enabled; preset: enabled) Drop-In: /etc/systemd/system/ssh.socket.d └─addresses.conf Active: active (listening) since Thu 2022-11-03 10:31:12 UTC; 23s ago Until: Thu 2022-11-03 10:31:12 UTC; 23s ago Triggers: ● ssh.service Listen: 0.0.0.0:1234 (Stream) Tasks: 0 (limit: 18901) Memory: 8.0K CPU: 332us CGroup: /system.slice/ssh.socket Nov 03 10:31:12 jammy systemd[1]: Listening on OpenBSD Secure Shell server socket. --- Test #2: root@jammy:~# grep "^ListenAddress" /etc/ssh/sshd_config ListenAddress 0.0.0.0:1234 ListenAddress [::]:4321 root@jammy:~# systemctl status ssh ● ssh.service - OpenBSD Secure Shell server Loaded: loaded (/lib/systemd/system/ssh.service; enabled; vendor preset: enabled) Drop-In: /run/systemd/system/service.d └─zzz-lxc-service.conf Active: active (running) since Thu 2022-11-03 10:33:34 UTC; 4s ago Docs: man:sshd(8) man:sshd_config(5) Process: 868 ExecStartPre=/usr/sbin/sshd -t (code=exited, status=0/SUCCESS) Main PID: 869 (sshd) Tasks: 1 (limit: 18901) Memory: 1.7M CPU: 42ms CGroup: /system.slice/ssh.service └─869 "sshd: /usr/sbin/sshd -D [listener] 0 of 10-100 startups" Nov 03 10:33:34 jammy systemd[1]: Starting OpenBSD Secure Shell server... Nov 03 10:33:34 jammy sshd[869]: Server listening on :: port 4321. Nov 03 10:33:34 jammy sshd[869]: Server listening on 0.0.0.0 port 1234. Nov 03 10:33:34 jammy systemd[1]: Started OpenBSD Secure Shell server. root@jammy:~# vi /etc/apt/sources.list root@jammy:~# cat /etc/apt/sources.list deb http://archive.ubuntu.com/ubuntu kinetic main restricted universe multiverse deb http://archive.ubuntu.com/ubuntu kinetic-updates main restricted universe multiverse deb http://archive.ubuntu.com/ubuntu kinetic-proposed main restricted universe multiverse deb http://security.ubuntu.com/ubuntu kinetic-security main restricted universe multiverse root@jammy:~# apt update && apt dist-upgrade -y [...] root@jammy:~# ls -alh /etc/systemd/system/ssh* lrwxrwxrwx 1 root root 31 Nov 3 10:33 /etc/systemd/system/sshd.service -> /lib/systemd/system/ssh.service root@jammy:~# systemctl status ssh.socket ○ ssh.socket - OpenBSD Secure Shell server socket Loaded: loaded (/lib/systemd/system/ssh.socket; disabled; preset: enabled) Active: inactive (dead) Triggers: ● ssh.service Listen: [::]:22 (Stream) root@jammy:~# systemctl status ssh.service ● ssh.service - OpenBSD Secure Shell server Loaded: loaded (/lib/systemd/system/ssh.service; enabled; preset: enabled) Drop-In: /run/systemd/system/service.d └─zzz-lxc-service.conf Active: active (running) since Thu 2022-11-03 10:38:25 UTC; 33s ago Docs: man:sshd(8) man:sshd_config(5) Main PID: 7153 (sshd) Tasks: 1 (limit: 18901) Memory: 1.4M CPU: 13ms CGroup: /system.slice/ssh.service └─7153 "sshd: /usr/sbin/sshd -D [listener] 0 of 10-100 startups" Nov 03 10:38:25 jammy systemd[1]: Starting OpenBSD Secure Shell server... Nov 03 10:38:25 jammy sshd[7153]: Server listening on :: port 4321. Nov 03 10:38:25 jammy sshd[7153]: Server listening on 0.0.0.0 port 1234. Nov 03 10:38:25 jammy systemd[1]: Started OpenBSD Secure Shell server. --- Test #3: root@jammy:~# apt update && apt dist-upgrade -y [...] Setting up openssh-server (1:9.0p1-1ubuntu7) ... Synchronizing state of ssh.service with SysV service script with /lib/systemd/systemd-sysv-install. Executing: /lib/systemd/systemd-sysv-install disable ssh Removed "/etc/systemd/system/sshd.service". Removed "/etc/systemd/system/multi-user.target.wants/ssh.service". Created symlink /etc/systemd/system/sockets.target.wants/ssh.socket → /lib/systemd/system/ssh.socket. rescue-ssh.target is a disabled or a static unit not running, not starting it. Failed to restart ssh.socket: Unit ssh.socket has a bad unit file setting. See system logs and 'systemctl status ssh.socket' for details. Could not execute systemctl: at /usr/bin/deb-systemd-invoke line 145. dpkg: error processing package openssh-server (--configure): installed openssh-server package post-installation script subprocess returned error exit status 1 [...] Errors were encountered while processing: openssh-server E: Sub-process /usr/bin/dpkg returned an error code (1) root@jammy:~# grep "^ListenAddress" /etc/ssh/sshd_config ListenAddress 0.0.0.0:1234 root@jammy:~# cat /etc/systemd/system/ssh.socket.d/addresses.conf [Socket] ListenStream= root@jammy:~# cat </etc/apt/sources.list.d/ubuntu-$(lsb_release -cs)-proposed.list # Enable Ubuntu proposed archive deb http://archive.ubuntu.com/ubuntu/ $(lsb_release -cs)-proposed restricted main multiverse universe EOF root@jammy:~# apt update && apt install openssh-server -y [...] root@jammy:~# systemctl status ssh.socket ● ssh.socket - OpenBSD Secure Shell server socket Loaded: loaded (/lib/systemd/system/ssh.socket; enabled; preset: enabled) Drop-In: /etc/systemd/system/ssh.socket.d └─addresses.conf Active: active (listening) since Thu 2022-11-03 11:02:39 UTC; 7s ago Until: Thu 2022-11-03 11:02:39 UTC; 7s ago Triggers: ● ssh.service Listen: 0.0.0.0:1234 (Stream) Tasks: 0 (limit: 18901) Memory: 8.0K CPU: 319us CGroup: /system.slice/ssh.socket Nov 03 11:02:39 jammy systemd[1]: Listening on OpenBSD Secure Shell server socket. root@jammy:~# cat /etc/systemd/system/ssh.socket.d/addresses.conf [Socket] ListenStream= ListenStream=0.0.0.0:1234 --- Test #4: root@jammy:~# apt update && apt dist-upgrade -y [...] Setting up openssh-server (1:9.0p1-1ubuntu7) ... Synchronizing state of ssh.service with SysV service script with /lib/systemd/systemd-sysv-install. Executing: /lib/systemd/systemd-sysv-install disable ssh Removed "/etc/systemd/system/sshd.service". Removed "/etc/systemd/system/multi-user.target.wants/ssh.service". Created symlink /etc/systemd/system/sockets.target.wants/ssh.socket → /lib/systemd/system/ssh.socket. rescue-ssh.target is a disabled or a static unit not running, not starting it. Failed to restart ssh.socket: Unit ssh.socket has a bad unit file setting. See system logs and 'systemctl status ssh.socket' for details. Could not execute systemctl: at /usr/bin/deb-systemd-invoke line 145. dpkg: error processing package openssh-server (--configure): installed openssh-server package post-installation script subprocess returned error exit status 1 [...] Errors were encountered while processing: openssh-server E: Sub-process /usr/bin/dpkg returned an error code (1) root@jammy:~# grep "^ListenAddress" /etc/ssh/sshd_config ListenAddress 0.0.0.0:1234 ListenAddress [::]:4321 root@jammy:~# cat /etc/systemd/system/ssh.socket.d/addresses.conf [Socket] ListenStream= root@jammy:~# apt update && apt install openssh-server -y [...] root@jammy:~# ls /etc/systemd/system/ssh* /etc/systemd/system/sshd.service