The error in your (Machine-1) log is:
> Setting up openssh-server (1:9.0p1-1ubuntu7) ...
> Replacing config file /etc/ssh/sshd_config with new version
> 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
I will try to reproduce this here, but please also attach the contents
of /etc/systemd/system/ssh.socket.d from the affected system.
** Changed in: openssh (Ubuntu)
Importance: Undecided => Critical
** Changed in: openssh (Ubuntu)
Status: New => Incomplete
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https://bugs.launchpad.net/bugs/1993869
Title:
openssh-server cannot listen or bind to anything other than :::2 after
upgrading to 22.10 from 22.04
Status in openssh package in Ubuntu:
Incomplete
Bug description:
This is a bug report to separate the second issue that was reported in this
bug report:
https://bugs.launchpad.net/ubuntu/+source/openssh/+bug/1993478
There's an issue after upgrading to 22.10 from 22.04 that prevents
opensshd from listening to anything other than :::2. I already
commented in the bug report I linked, so I'll just copy/paste and add
some details. I guess.
The issue is that after upgrading, sshd doesn't use the Listen port or
ListenAddress config from the sshd_config file or any custom config
file that was in the sshd_config.d drop in folder anymore.
Other drop in settings from sshd.config.d seem to be applied normally,
the issue seem to be only for IP binding and custom ports.
If I change Accept=no by Accept=yes in ssh.socket and reloads the
socket unit, I can start sshd on a different port and I can also bind
the IP to something else than ::
There's an issue still, an instance of sshd is still listening to
:::22 that is not started by SSHD but by init.
root@ubuntulocal:~# netstat -antp
Active Internet connections (servers and established)
Proto Recv-Q Send-Q Local Address Foreign Address State PID/Program name
tcp 0 0 0.0.0.0:21 0.0.0.0:* LISTEN 568/vsftpd
tcp 0 0 0.0.0.0:622 0.0.0.0:* LISTEN 571/sshd: /usr/sbin
tcp 0 272 192.168.1.225:622 192.168.1.220:2473 ESTABLISHED 1027/sshd: root@pts
tcp6 0 0 :::22 :::* LISTEN 1/init
If I reboot after changing this no to yes in ssh.socket does not survive a
reboot and fails to load sshd with a "Failed to queue service startup job"
error.
Oct 21 15:41:56 ubuntulocal systemd[1]: ssh.socket: Failed to queue service
startup job (Maybe the service file is missing or not a template unit?):
Invalid argument
Oct 21 15:41:56 ubuntulocal systemd[1]: ssh.socket: Failed with result
'resources'.
I had to mask/stop the sshd.socket unit and create a custom sshd
service in /etc/systemd/system to be able start sshd on a custom port
and IP.
chris@ubuntulocal:~$ systemctl status ssh.socket
● ssh.socket - OpenBSD Secure Shell server socket
Loaded: loaded (/lib/systemd/system/ssh.socket; enabled; preset: enabled)
Active: active (running) since Fri 2022-10-21 23:08:09 UTC; 1min 24s ago
Until: Fri 2022-10-21 23:08:09 UTC; 1min 24s ago
Triggers: ● ssh.service
Listen: [::]:22 (Stream)
Tasks: 0 (limit: 18899)
Memory: 4.0K
CPU: 418us
CGroup: /system.slice/ssh.socket
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