Thanks for reporting this. I confirmed it with:
root@n:~# cat > /etc/ssh/sshd_config.d/ports.conf << EOF
> Port 22
> Port 1024
> EOF
root@n:~# /lib/systemd/system-generators/sshd-socket-generator .
root@n:~# cat ssh.socket.d/addresses.conf
# Automatically generated by sshd-socket-generator
[Socket]
ListenStream=
ListenStream=1024
Looking at the code the bug is very clear.
** Changed in: openssh (Ubuntu)
Status: New => Triaged
** Tags added: foundations-todo
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https://bugs.launchpad.net/bugs/2059872
Title:
Unable to listen on port 22 if multiple Port= present in sshd
configuration
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