It seems like I can't add another Debian bug reference to this bug, but
I found this one to be a very interesting read:

https://bugs.debian.org/cgi-bin/bugreport.cgi?bug=982950

In a nutshell, although the "After=network-online.target" change can be
considered to be a workaround here, I find it quite unlikely that the
Debian maintainer (and therefore Ubuntu) will accept a patch proposing
to use this statement in openssh's systemd service file.  You can find a
rationale by Colin in the bug I mentioned above.

In a way, I think this bug is similar to
https://bugs.launchpad.net/ubuntu/+source/nfs-utils/+bug/1918141, and we
still don't seem to have a good "silver bullet" for these cases...

** Bug watch added: Debian Bug tracker #982950
   https://bugs.debian.org/cgi-bin/bugreport.cgi?bug=982950

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https://bugs.launchpad.net/bugs/216847

Title:
  sshd will not start at boot if ListenAddress is set, because network
  interface is not yet up

Status in portable OpenSSH:
  Unknown
Status in openssh package in Ubuntu:
  Confirmed
Status in openssh package in Debian:
  New
Status in openssh package in Fedora:
  Unknown

Bug description:
  Binary package hint: openssh-server

  The sshd will not start at boot if the ListenAddress option in
  /etc/ssh/sshd_config is set to an IPv4 address other then 0.0.0.0 .

  I am using Ubuntu 7.10 and the version 1:4.6p1-5ubuntu0.2 of the 
openssh-server package.
  I would expect that sshd is started after boot but it will not and I found 
this in /var/log/auth.log:

  sshd[4527]: error: Bind to port 22 on 10.1.1.22 failed: Cannot assign 
requested address.
  sshd[4527]: fatal: Cannot bind any address.

  Once the System is started you can start/stop the sshd with the
  /etc/init.d/ssh script without any problems.

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