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[Nick Rosbrook <2114144@xxxxxxxxxxxxxxxxxx>]

Can you please elaborate on what "broken" means in your case? What does
the failure look like?

In a 24.04 container, I am able to configure a second port, listen on
them fine, and connect via either port from my host to the container
(see below for my terminal output).

Thanks for sharing your sshd config. Can you please also share the
output of:

$ systemctl cat ssh.service
$ systemctl cat ssh.socket
$ systemctl status ssh.socket ssh.service

--

root@n:~# apt policy openssh-server
openssh-server:
  Installed: 1:9.6p1-3ubuntu13.12
  Candidate: 1:9.6p1-3ubuntu13.12
  Version table:
 *** 1:9.6p1-3ubuntu13.12 500 (phased 95%)
        500 http://archive.ubuntu.com/ubuntu noble-updates/main amd64 Packages
        100 /var/lib/dpkg/status
     1:9.6p1-3ubuntu13.11 500
        500 http://security.ubuntu.com/ubuntu noble-security/main amd64 Packages
     1:9.6p1-3ubuntu13 500
        500 http://archive.ubuntu.com/ubuntu noble/main amd64 Packages
root@n:~# systemctl status ssh.socket
● ssh.socket - OpenBSD Secure Shell server socket
     Loaded: loaded (/usr/lib/systemd/system/ssh.socket; enabled; preset: enabled)
     Active: active (listening) since Thu 2025-06-12 13:06:26 UTC; 27s ago
   Triggers: ● ssh.service
     Listen: [::]:22 (Stream)
     CGroup: /system.slice/ssh.socket

Jun 12 13:06:26 n systemd[1]: Listening on ssh.socket - OpenBSD Secure Shell server socket.
root@n:~# systemctl status ssh.service
● ssh.service - OpenBSD Secure Shell server
     Loaded: loaded (/usr/lib/systemd/system/ssh.service; disabled; preset: enabled)
     Active: active (running) since Thu 2025-06-12 13:07:27 UTC; 11s ago
TriggeredBy: ● ssh.socket
       Docs: man:sshd(8)
             man:sshd_config(5)
    Process: 717 ExecStartPre=/usr/sbin/sshd -t (code=exited, status=0/SUCCESS)
   Main PID: 718 (sshd)
      Tasks: 1 (limit: 18286)
     Memory: 3.0M (peak: 3.7M)
        CPU: 47ms
     CGroup: /system.slice/ssh.service
             └─718 "sshd: /usr/sbin/sshd -D [listener] 0 of 10-100 startups"

Jun 12 13:07:27 n systemd[1]: Starting ssh.service - OpenBSD Secure Shell server...
Jun 12 13:07:27 n sshd[718]: Server listening on :: port 22.
Jun 12 13:07:27 n systemd[1]: Started ssh.service - OpenBSD Secure Shell server.
Jun 12 13:07:28 n sshd[720]: Accepted publickey for ubuntu from 10.19.111.1 port 55494 ssh2: RSA SHA256:VMGz6tsZ02V9ra>
Jun 12 13:07:28 n sshd[720]: pam_unix(sshd:session): session opened for user ubuntu(uid=1000) by ubuntu(uid=0)


Here is where I add a second port configuration:


root@n:~# cat > /etc/ssh/sshd_config.d/port.conf << EOF
Port 22
Port 443
EOF
root@n:~# systemctl daemon-reload
root@n:~# systemctl restart ssh.socket
root@n:~# systemctl status ssh.socket
● ssh.socket - OpenBSD Secure Shell server socket
     Loaded: loaded (/usr/lib/systemd/system/ssh.socket; enabled; preset: enabled)
    Drop-In: /run/systemd/generator/ssh.socket.d
             └─addresses.conf
     Active: active (running) since Thu 2025-06-12 13:20:05 UTC; 24s ago
   Triggers: ● ssh.service
     Listen: [::]:443 (Stream)
             [::]:22 (Stream)
     CGroup: /system.slice/ssh.socket

Jun 12 13:20:05 n systemd[1]: Stopping ssh.socket - OpenBSD Secure Shell server socket...
Jun 12 13:20:05 n systemd[1]: Listening on ssh.socket - OpenBSD Secure Shell server socket.
root@n:~# systemctl cat ssh.socket
# /usr/lib/systemd/system/ssh.socket
[Unit]
Description=OpenBSD Secure Shell server socket
Before=sockets.target ssh.service
ConditionPathExists=!/etc/ssh/sshd_not_to_be_run

[Socket]
ListenStream=22
Accept=no
FreeBind=yes

[Install]
WantedBy=sockets.target
RequiredBy=ssh.service

# /run/systemd/generator/ssh.socket.d/addresses.conf
# Automatically generated by sshd-socket-generator

[Socket]
ListenStream=
ListenStream=443
ListenStream=22
root@n:~# systemctl status ssh.service
● ssh.service - OpenBSD Secure Shell server
     Loaded: loaded (/usr/lib/systemd/system/ssh.service; disabled; preset: enabled)
     Active: active (running) since Thu 2025-06-12 13:20:05 UTC; 4min 34s ago
TriggeredBy: ● ssh.socket
       Docs: man:sshd(8)
             man:sshd_config(5)
    Process: 960 ExecStartPre=/usr/sbin/sshd -t (code=exited, status=0/SUCCESS)
   Main PID: 962 (sshd)
      Tasks: 1 (limit: 18286)
     Memory: 1.4M (peak: 4.2M)
        CPU: 106ms
     CGroup: /system.slice/ssh.service
             └─962 "sshd: /usr/sbin/sshd -D [listener] 0 of 10-100 startups"

Jun 12 13:20:05 n systemd[1]: Starting ssh.service - OpenBSD Secure Shell server...
Jun 12 13:20:05 n sshd[962]: Server listening on :: port 443.
Jun 12 13:20:05 n sshd[962]: Server listening on :: port 22.
Jun 12 13:20:05 n systemd[1]: Started ssh.service - OpenBSD Secure Shell server.
Jun 12 13:24:18 n sshd[972]: Accepted publickey for ubuntu from 10.19.111.1 port 56454 ssh2: RSA SHA256:VMGz6tsZ02V9ra>
Jun 12 13:24:18 n sshd[972]: pam_unix(sshd:session): session opened for user ubuntu(uid=1000) by ubuntu(uid=0)
Jun 12 13:24:34 n sshd[1048]: Accepted publickey for ubuntu from 10.19.111.1 port 39962 ssh2: RSA SHA256:VMGz6tsZ02V9r>
Jun 12 13:24:34 n sshd[1048]: pam_unix(sshd:session): session opened for user ubuntu(uid=1000) by ubuntu(uid=0)

In the above status output, both of my connections can be seen.

-- 
You received this bug notification because you are a member of
Debcrafters packages, which is subscribed to openssh in Ubuntu.
https://bugs.launchpad.net/bugs/2114144

Title:
  Openssh Server ignores Port xxx

Status in openssh package in Ubuntu:
  Incomplete

Bug description:
  I have:
  Port 22
  Port 443

  In my sshd_config, to have it listen to a secondary port 443 to get around firewalls that block ssh.
  Until a few days ago, like port forwarding, this worked, but now, like port forwarding, it is broken.
  The second Port item is just ignored.  It is not acceptable for Canonical to randomly break important functionality like this.

  ProblemType: Bug
  DistroRelease: Ubuntu 24.04
  Package: openssh-server 1:9.6p1-3ubuntu13.11
  Uname: Linux 6.15.0 x86_64
  ApportVersion: 2.28.1-0ubuntu3.7
  Architecture: amd64
  CasperMD5CheckResult: unknown
  CurrentDesktop: MATE
  Date: Thu Jun 12 00:07:41 2025
  SourcePackage: openssh
  UpgradeStatus: No upgrade log present (probably fresh install)

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