Chris, Kevin, John, or anyone else affected:

Is it possible that you changed your sshd_config without actually
reloading and restarting ssh.socket, a while (hours, days, etc.) before
the upgrade occurred? I am wondering if it's possible that the
configuration was already broken by a local change, and the upgrade
(which will call systemctl daemon-reload and systemctl restart
ssh.socket) just surfaced the problem.

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

Title:
  OpenSSH server config broken on unattended update

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