As Seth mentioned in comment #13 likely network-online.target should be the 
solution.
@Owlbsidian - could you test and confirm with that as a fix as well?

A related fun quote from the systemd page about it:
"... please just fix your program to be friendly to dynamically changing 
network configuration. That way you will make your users happy because things 
just start to work, and you will get fewer bug reports ..."

Without that support you can still run into issues if e.g. you have a
manually added interface you depend on (no service target will help you
there). But that in turn would be an upstream feature request more than
anything else.

Anyway, as long as ssh doesn't support that we might want to finally tackle 
that issue to at least improve it. Now that systemd has more means to express 
"online".
Maybe even by directly fixing it in Debian.

Subscribing server to track and cjwatson for his opinion (actually I see
he is auto-subscribed to the pkg so he will see).

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You received this bug notification because you are a member of Ubuntu
Touch seeded packages, which is subscribed to openssh in Ubuntu.
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 openssh package in Ubuntu:
  Confirmed

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.

To manage notifications about this bug go to:
https://bugs.launchpad.net/ubuntu/+source/openssh/+bug/216847/+subscriptions

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