Okay, thanks for following up.

If anyone finds a way to reliably reproduce this, please let me know. So
far I have tried:

- adding a custom port (both directly in /etc/ssh/sshd_config, and using 
/etc/ssh/sshd_config.d/port.conf)
- upgrading openssh-server (both manually, and by running unattended-upgrades)

In any case, I do not experience any connection refused errors, nor do I
see any errors on the server side ssh units (ssh.service, ssh.socket).

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https://bugs.launchpad.net/bugs/2087551

Title:
  OpenSSH server config broken on unattended update

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