As expected, on reboot all is fine for the service status

ubuntu@node-horsea:~$ systemctl status ssh.service
● ssh.service - OpenBSD Secure Shell server
     Loaded: loaded (/lib/systemd/system/ssh.service; disabled; preset: enabled)
    Drop-In: /etc/systemd/system/ssh.service.d
             └─00-socket.conf
     Active: active (running) since Thu 2023-02-02 10:54:40 UTC; 12min ago
TriggeredBy: ● ssh.socket
       Docs: man:sshd(8)
             man:sshd_config(5)
    Process: 2689 ExecStartPre=/usr/sbin/sshd -t (code=exited, status=0/SUCCESS)
   Main PID: 2690 (sshd)
      Tasks: 1 (limit: 38220)
     Memory: 5.3M
        CPU: 894ms
     CGroup: /system.slice/ssh.service
             └─2690 "sshd: /usr/sbin/sshd -D [listener] 0 of 10-100 startups"

Feb 02 11:06:27 node-horsea sshd[14629]: Accepted publickey for ubuntu from 
10.172.196.173 port 47348 ssh2: RSA 
SHA256:KyONnhWWzlbscZNTHPZ25GWCXDQY5u/UD72EtQcwtqU
Feb 02 11:06:27 node-horsea sshd[14629]: pam_unix(sshd:session): session opened 
for user ubuntu(uid=1000) by (uid=0)
Feb 02 11:06:27 node-horsea sshd[14629]: pam_env(sshd:session): deprecated 
reading of user environment enabled
Feb 02 11:06:58 node-horsea sshd[14735]: Accepted publickey for ubuntu from 
10.172.196.173 port 55016 ssh2: RSA 
SHA256:KyONnhWWzlbscZNTHPZ25GWCXDQY5u/UD72EtQcwtqU
Feb 02 11:06:58 node-horsea sshd[14735]: pam_unix(sshd:session): session opened 
for user ubuntu(uid=1000) by (uid=0)
Feb 02 11:06:59 node-horsea sshd[14735]: pam_env(sshd:session): deprecated 
reading of user environment enabled
Feb 02 11:07:03 node-horsea sshd[14796]: Accepted publickey for ubuntu from 
10.172.196.173 port 57034 ssh2: RSA 
SHA256:KyONnhWWzlbscZNTHPZ25GWCXDQY5u/UD72EtQcwtqU
Feb 02 11:07:03 node-horsea sshd[14796]: pam_unix(sshd:session): session opened 
for user ubuntu(uid=1000) by (uid=0)
Feb 02 11:07:03 node-horsea sshd[14796]: pam_env(sshd:session): deprecated 
reading of user environment enabled
Feb 02 11:07:03 node-horsea sshd[14796]: pam_unix(sshd:session): session closed 
for user ubuntu
ubuntu@node-horsea:~$ 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 Thu 2023-02-02 10:54:21 UTC; 12min ago
      Until: Thu 2023-02-02 10:54:21 UTC; 12min ago
   Triggers: ● ssh.service
     Listen: [::]:22 (Stream)
      Tasks: 0 (limit: 38220)
     Memory: 8.0K
        CPU: 894us
     CGroup: /system.slice/ssh.socket

Feb 02 10:54:21 node-horsea systemd[1]: Listening on OpenBSD Secure
Shell server socket.


And out of this condition it can even complete the package
configuration.

ubuntu@node-horsea:~$ sudo dpkg-reconfigure openssh-server
/usr/sbin/dpkg-reconfigure: openssh-server is broken or not fully installed
ubuntu@node-horsea:~$ sudo apt-get install --fix-broken
Reading package lists... Done
Building dependency tree... Done
Reading state information... Done
0 upgraded, 0 newly installed, 0 to remove and 0 not upgraded.
1 not fully installed or removed.
After this operation, 0 B of additional disk space will be used.
Setting up openssh-server (1:9.0p1-1ubuntu8) ...
Replacing config file /etc/ssh/sshd_config with new version
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
Warning: Stopping ssh.service, but it can still be activated by:
  ssh.socket
rescue-ssh.target is a disabled or a static unit not running, not starting it.
ubuntu@node-horsea:~$ echo $?
0

-- 
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/2004551

Title:
  upgrade to lunar fails due to rescue-ssh.target or port 22 takeover

Status in openssh package in Ubuntu:
  New

Bug description:
  Hi,
  I just upgraded a system from Jammy to Lunar and openssh-server refuses to 
upgrade well.

  Setting up openssh-server (1:9.0p1-1ubuntu8) ...
  Replacing config file /etc/ssh/sshd_config with new version
  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
  rescue-ssh.target is a disabled or a static unit not running, not starting it.
  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
  Processing triggers for man-db (2.11.2-1) ...
  Processing triggers for libc-bin (2.36-0ubuntu4) ...
  Errors were encountered while processing:
   openssh-server
  Error: Timeout was reached
  needrestart is being skipped since dpkg has failed
  E: Sub-process /usr/bin/dpkg returned an error code (1)

  I'm not sure what exactly it is.
  This output complains about rescue-ssh.target and indeed that can not be 
started even directly.

  $ sudo systemctl start rescue-ssh.target
  A dependency job for rescue-ssh.target failed. See 'journalctl -xe' for 
details.

  And in postinst is a try to start it:
  $  grep rescue /var/lib/dpkg/info/openssh-server.postinst 
                deb-systemd-invoke $_dh_action 'rescue-ssh.target' >/dev/null 
|| true

  
  But I think the underlying issue is that ssh is already on, and I'm logged in 
via it.
  And that makes the service restart of the ssh socket which was added break.

  Feb 02 10:40:56 node-horsea systemd[104560]: ssh.socket: Failed to create 
listening socket ([::]:22): Address already in use
  Feb 02 10:40:56 node-horsea systemd[1]: ssh.socket: Failed to receive 
listening socket ([::]:22): Input/output error
  Feb 02 10:40:56 node-horsea systemd[1]: ssh.socket: Failed to listen on 
sockets: Input/output error
  Feb 02 10:40:56 node-horsea systemd[1]: ssh.socket: Failed with result 
'resources'.

  
  Now, whichever it is, it is hard to resolve.
  The only way to get the socket to own it would be rebooting so that sshd lets 
go and systemd can take over.
  I could reboot, but that is not the point.
  What if I'd want to get the service and upgrade completed before reboot.
  Because as of now dpkg considers the system unhappy, and that would usually 
be a sign for "better not reboot before being resolved" to me.

  One thing though, I have not upgraded with do-release-upgrade - would
  we / do we have magic there to make the ssh socket activation
  transition smoother?

To manage notifications about this bug go to:
https://bugs.launchpad.net/ubuntu/+source/openssh/+bug/2004551/+subscriptions


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