Perry, I just revisited this:

 - /etc/network/if-up.d/openssh-server hack introduces a race (you run
into connection errors after bringing up a new interface as sshd stops
listening briefly while being reloaded).

 - I can't seem to be able to actually reproduce that issue: I can start
a VM with no network interfaces, remove the above hack, then start sshd,
then bring up an ethernet interface, and I can connect to ssh via
ethernet just fine. Also, e. g. Fedora has no counterpart of this hack,
and these days a lot of people would complain if that would cause
problems, as hotpluggable/roaming network devices are everywhere.

 - /etc/network/if-up.d/ isn't being run when using networkd/netplan,
thus in our cloud instances. So far this doesn't seem to have caused any
issues.

So my questions:

  (1) Can you please describe more precisely what exactly you did back
then? Do you have a nonstandard SSH configuration with some
ListenAddresses/AddressFamily restrictions or similar?

  (2) Can you please disable the hack (sudo chmod 0 /etc/network/if-up.d
/openssh-server) and check if your use case works without it?

Thanks!

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https://bugs.launchpad.net/bugs/103436

Title:
  sshd not reconfigured by /etc/network

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