Okay. I am having a hard time following the switches between "your
version" and "my version", but I will do my best.

> Here is from a server with your version, notice it is not listening to
443 even though I have it in the configuration:

The only thing you changed is the ExecStartPre= line. I would therefore
expect the failure you see to be from `sshd -t`. Is that the case?

> Here is from a server with your version, notice it is not listening to
443 even though I have it in the configuration:

If the drop-in is not getting generated, it's probably because an error
in sshd-socket-generator. This, in combination with the above point
about `sshd -t`, suggests to me that there is an error in your
configuration (specifically, it's possible you are using something too
new for openssh 9.6, but supported in openssh 10.x).

On a server *with Ubuntu's version installed*, and where the bug is
present, can you share the output of:

$ sshd -G
$ mkdir -p /tmp/out
$ /usr/lib/systemd/system-generators/sshd-socket-generator /tmp/out
$ cat /tmp/out/ssh.socket.d/addresses.conf

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https://bugs.launchpad.net/bugs/2114144

Title:
  Openssh Server ignores Port xxx

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