Public bug reported:

After processing system update by:
apt-get clean && apt-get autoclean && apt-get autoremove && apt-get update && 
apt-get upgrade && apt-get dist-upgrade && reboot

ssh server stops starting at system boot.

It starts after doing:
mkdir /var/run/sshd
chmod 0755 /var/run/sshd
service ssh start

It happens on fresh Ubuntu-16.04 installs on every VPS provide I have
tested so far.

ProblemType: Bug
DistroRelease: Ubuntu 16.04
Package: openssh-server 1:7.2p2-4ubuntu2.6
Uname: Linux 2.6.32-042stab127.2 x86_64
ApportVersion: 2.20.1-0ubuntu2.18
Architecture: amd64
Date: Thu Jan 31 10:18:56 2019
ProcEnviron:
 TERM=xterm
 PATH=(custom, no user)
SSHDConfig: Error: command ['/usr/sbin/sshd', '-T'] failed with exit code 255: 
Missing privilege separation directory: /var/run/sshd
SourcePackage: openssh
UpgradeStatus: No upgrade log present (probably fresh install)

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


** Tags: amd64 apport-bug xenial

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https://bugs.launchpad.net/bugs/1814124

Title:
  sshd does not start after update

Status in openssh package in Ubuntu:
  New

Bug description:
  After processing system update by:
  apt-get clean && apt-get autoclean && apt-get autoremove && apt-get update && 
apt-get upgrade && apt-get dist-upgrade && reboot

  ssh server stops starting at system boot.

  It starts after doing:
  mkdir /var/run/sshd
  chmod 0755 /var/run/sshd
  service ssh start

  It happens on fresh Ubuntu-16.04 installs on every VPS provide I have
  tested so far.

  ProblemType: Bug
  DistroRelease: Ubuntu 16.04
  Package: openssh-server 1:7.2p2-4ubuntu2.6
  Uname: Linux 2.6.32-042stab127.2 x86_64
  ApportVersion: 2.20.1-0ubuntu2.18
  Architecture: amd64
  Date: Thu Jan 31 10:18:56 2019
  ProcEnviron:
   TERM=xterm
   PATH=(custom, no user)
  SSHDConfig: Error: command ['/usr/sbin/sshd', '-T'] failed with exit code 
255: Missing privilege separation directory: /var/run/sshd
  SourcePackage: openssh
  UpgradeStatus: No upgrade log present (probably fresh install)

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