SSH to finally learn how to pick up addresses later is a long time demand for 
ssh to do that.
But it is a demand for an upstream feature IMHO.

I know it can thse day's re-pickup adresses that it lost:
- I have a KVM guest with one interface and I have set up ssh listen to only 
interface 192.168.122.221
  ListenAddress 192.168.122.221
- All normal/fine.
- If I take away the Network device it doesn#t work (obviously)
- If I attach the device ssh without being restarted works again.

But the problem here as already takled about is the fatal-fail of ssh to
start if the ListenAddress not exists at the time.

And network-online.target might be a help for some cases, but not e.g. for 
networks added much later (like my virtual network example).
When I say this is a demand to upstream SSH for a long time I really mean it - 
this is in Ubuntu for a decade in bug 216847 and for like 3 years in upstream 
SSH.

I think this bug here should be used to change it to network-online.target if 
that really helps some cases.
The old bug I referred will continue to track until upstream implements 
IP_FREEBIND or any other late pickup tech (like listening to netlink events).

-- 
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/1549473

Title:
  ssh will not start at boot:  systemctl status ssh -> output is listed
  as failed 255.

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

Bug description:
  Using apt I have reinstalled and purged both ssh and openssh-server. 
  apt-get remove --purge ssh openssh-server
  reinstalled
  updated
  and on boot the ctl status is failed 255

  After much forum research and attempts to default solutions, the final word 
was that reinstall usually fixes this issue. 
  With the issue usually stemming from ssh service trying to start before 
network services are available.

  Currently I have no logs available with 
  journalctl -u sshd | tail -100

  I can provide info pertaining to this on request.

  ProblemType: Bug
  DistroRelease: Ubuntu 15.10
  Package: ssh 1:6.9p1-2ubuntu0.1
  ProcVersionSignature: Ubuntu 4.2.0-30.35-generic 4.2.8-ckt3
  Uname: Linux 4.2.0-30-generic x86_64
  ApportVersion: 2.19.1-0ubuntu5
  Architecture: amd64
  CurrentDesktop: LXDE
  Date: Wed Feb 24 14:27:55 2016
  InstallationDate: Installed on 2016-02-09 (15 days ago)
  InstallationMedia: Lubuntu 15.10 "Wily Werewolf" - Release amd64 (20151021)
  PackageArchitecture: all
  SourcePackage: openssh
  UpgradeStatus: No upgrade log present (probably fresh install)

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