Public bug reported:

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)

** Affects: openssh (Ubuntu)
     Importance: Undecided
         Status: New


** Tags: amd64 apport-bug boot ssh wily

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https://bugs.launchpad.net/bugs/1549473

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

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