Yes, the issue turned out to be interplay with systemd, since you are
now using the Gawd-Aweful systemd as a superdaemon, it is opening the initial
port but there is a delay before openssh opens the second port 443.
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On Tue, 18 Nov 2025, Nick Rosbrook wrote:
> Date: Tue, 18 Nov 2025 21:18:00 -0000
> From: Nick Rosbrook <[email protected]>
> To: [email protected]
> Subject: [Bug 2114144] Re: Openssh Server ignores Port xxx
>
> Hi - did you ever figure out what was causing your issue? Looking over
> everything again, it seems that for whatever reason, openssh was simply
> not parsing your port option (the ssh -G output only show port 22), but
> the socket generator was working as expected in that case.
>
> --
> You received this bug notification because you are subscribed to the bug
> report.
> https://bugs.launchpad.net/bugs/2114144
>
> Title:
> Openssh Server ignores Port xxx
>
> Status in openssh package in Ubuntu:
> Expired
>
> 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)
>
> To manage notifications about this bug go to:
> https://bugs.launchpad.net/ubuntu/+source/openssh/+bug/2114144/+subscriptions
>
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https://bugs.launchpad.net/bugs/2114144
Title:
Openssh Server ignores Port xxx
To manage notifications about this bug go to:
https://bugs.launchpad.net/ubuntu/+source/openssh/+bug/2114144/+subscriptions
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