Public bug reported:

Installation seems to fail on restarting ssh.socket via systemctl

Setting up openssh-server (1:9.2p1-2ubuntu1) ...
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
Errors were encountered while processing:
 openssh-server
E: Sub-process /usr/bin/dpkg returned an error code (1)

$ systemctl status ssh.socket
× ssh.socket - OpenBSD Secure Shell server socket
     Loaded: loaded (/lib/systemd/system/ssh.socket; enabled; preset: enabled)
     Active: failed (Result: resources) since Tue 2023-05-23 15:01:41 CEST; 48s 
ago
   Duration: 3h 6min 36.071s
   Triggers: ● ssh.service
     Listen: [::]:22 (Stream)
        CPU: 2ms

May 23 11:55:05 venus2 systemd[1]: Listening on ssh.socket - OpenBSD Secure 
Shell server socket.
May 23 15:01:41 venus2 systemd[1]: ssh.socket: Deactivated successfully.
May 23 15:01:41 venus2 systemd[1]: Closed ssh.socket - OpenBSD Secure Shell 
server socket.
May 23 15:01:41 venus2 systemd[1]: Stopping ssh.socket - OpenBSD Secure Shell 
server socket...
May 23 15:01:41 venus2 systemd[2631]: ssh.socket: Failed to create listening 
socket ([::]:22): Address already in use
May 23 15:01:41 venus2 systemd[1]: ssh.socket: Failed to receive listening 
socket ([::]:22): Input/output error
May 23 15:01:41 venus2 systemd[1]: ssh.socket: Failed to listen on sockets: 
Input/output error
May 23 15:01:41 venus2 systemd[1]: ssh.socket: Failed with result 'resources'.
May 23 15:01:41 venus2 systemd[1]: Failed to listen on ssh.socket - OpenBSD 
Secure Shell server socket.

At this point, sshd is no longer listening for new connections.  A
manual systemctl restart of ssh.socket fails with the same error.  I am
ssh-ed into this box, so I *think* the failure is because my session is
already sitting on port 22, maybe?  The only way I can be sure I will be
able to ssh to this box again is to reboot it (so that ssh.socket can
start cleanly).

$ lsb_release -rd
No LSB modules are available.
Description:    Ubuntu Mantic Minotaur (development branch)
Release:        23.10

$ apt policy openssh-server
openssh-server:
  Installed: 1:9.2p1-2ubuntu1
  Candidate: 1:9.2p1-2ubuntu1
  Version table:
 *** 1:9.2p1-2ubuntu1 500
        500 http://ch.ports.ubuntu.com/ubuntu-ports mantic-proposed/main 
riscv64 Packages
        100 /var/lib/dpkg/status
     1:9.0p1-1ubuntu8.1 500
        500 http://ch.ports.ubuntu.com/ubuntu-ports mantic/main riscv64 Packages

ProblemType: Bug
DistroRelease: Ubuntu 23.10
Package: openssh-server 1:9.2p1-2ubuntu1
ProcVersionSignature: Ubuntu 6.2.0-19.19.1-generic 6.2.6
Uname: Linux 6.2.0-19-generic riscv64
ApportVersion: 2.26.1-0ubuntu3
Architecture: riscv64
CasperMD5CheckResult: unknown
CloudArchitecture: riscv64
CloudBuildName: server
CloudID: nocloud
CloudName: unknown
CloudPlatform: nocloud
CloudSerial: 20230413.1
CloudSubPlatform: seed-dir (/var/lib/cloud/seed/nocloud-net)
Date: Tue May 23 14:58:35 2023
SSHDConfig: Error: command ['/usr/sbin/sshd', '-T'] failed with exit code 1: 
/etc/ssh/sshd_config.d/50-cloud-init.conf: Permission denied
SourcePackage: openssh
UpgradeStatus: Upgraded to mantic on 2023-05-12 (11 days ago)

** Affects: openssh (Ubuntu)
     Importance: Undecided
         Status: New


** Tags: apport-bug cloud-image mantic package-from-proposed riscv64

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https://bugs.launchpad.net/bugs/2020474

Title:
  openssh-server-1:9.2p1-2ubuntu1 fails post-installation

Status in openssh package in Ubuntu:
  New

Bug description:
  Installation seems to fail on restarting ssh.socket via systemctl

  Setting up openssh-server (1:9.2p1-2ubuntu1) ...
  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
  Errors were encountered while processing:
   openssh-server
  E: Sub-process /usr/bin/dpkg returned an error code (1)

  $ systemctl status ssh.socket
  × ssh.socket - OpenBSD Secure Shell server socket
       Loaded: loaded (/lib/systemd/system/ssh.socket; enabled; preset: enabled)
       Active: failed (Result: resources) since Tue 2023-05-23 15:01:41 CEST; 
48s ago
     Duration: 3h 6min 36.071s
     Triggers: ● ssh.service
       Listen: [::]:22 (Stream)
          CPU: 2ms

  May 23 11:55:05 venus2 systemd[1]: Listening on ssh.socket - OpenBSD Secure 
Shell server socket.
  May 23 15:01:41 venus2 systemd[1]: ssh.socket: Deactivated successfully.
  May 23 15:01:41 venus2 systemd[1]: Closed ssh.socket - OpenBSD Secure Shell 
server socket.
  May 23 15:01:41 venus2 systemd[1]: Stopping ssh.socket - OpenBSD Secure Shell 
server socket...
  May 23 15:01:41 venus2 systemd[2631]: ssh.socket: Failed to create listening 
socket ([::]:22): Address already in use
  May 23 15:01:41 venus2 systemd[1]: ssh.socket: Failed to receive listening 
socket ([::]:22): Input/output error
  May 23 15:01:41 venus2 systemd[1]: ssh.socket: Failed to listen on sockets: 
Input/output error
  May 23 15:01:41 venus2 systemd[1]: ssh.socket: Failed with result 'resources'.
  May 23 15:01:41 venus2 systemd[1]: Failed to listen on ssh.socket - OpenBSD 
Secure Shell server socket.

  At this point, sshd is no longer listening for new connections.  A
  manual systemctl restart of ssh.socket fails with the same error.  I
  am ssh-ed into this box, so I *think* the failure is because my
  session is already sitting on port 22, maybe?  The only way I can be
  sure I will be able to ssh to this box again is to reboot it (so that
  ssh.socket can start cleanly).

  $ lsb_release -rd
  No LSB modules are available.
  Description:  Ubuntu Mantic Minotaur (development branch)
  Release:      23.10

  $ apt policy openssh-server
  openssh-server:
    Installed: 1:9.2p1-2ubuntu1
    Candidate: 1:9.2p1-2ubuntu1
    Version table:
   *** 1:9.2p1-2ubuntu1 500
          500 http://ch.ports.ubuntu.com/ubuntu-ports mantic-proposed/main 
riscv64 Packages
          100 /var/lib/dpkg/status
       1:9.0p1-1ubuntu8.1 500
          500 http://ch.ports.ubuntu.com/ubuntu-ports mantic/main riscv64 
Packages

  ProblemType: Bug
  DistroRelease: Ubuntu 23.10
  Package: openssh-server 1:9.2p1-2ubuntu1
  ProcVersionSignature: Ubuntu 6.2.0-19.19.1-generic 6.2.6
  Uname: Linux 6.2.0-19-generic riscv64
  ApportVersion: 2.26.1-0ubuntu3
  Architecture: riscv64
  CasperMD5CheckResult: unknown
  CloudArchitecture: riscv64
  CloudBuildName: server
  CloudID: nocloud
  CloudName: unknown
  CloudPlatform: nocloud
  CloudSerial: 20230413.1
  CloudSubPlatform: seed-dir (/var/lib/cloud/seed/nocloud-net)
  Date: Tue May 23 14:58:35 2023
  SSHDConfig: Error: command ['/usr/sbin/sshd', '-T'] failed with exit code 1: 
/etc/ssh/sshd_config.d/50-cloud-init.conf: Permission denied
  SourcePackage: openssh
  UpgradeStatus: Upgraded to mantic on 2023-05-12 (11 days ago)

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