I run several OpenVZ VPS servers from 4 different providers and last month I 
lost ssh access to all of them after doing an update. I have never had such 
problem before and I update regularly.
I don't have access to KVM to check it.

1
lrwxrwxrwx 1 root root 4 Feb  3 15:16 /var/run -> /run

2
tmpfs on /run type tmpfs (rw,nosuid,nodev,mode=755)

3
$ cat /usr/lib/tmpfiles.d/sshd.conf 
d /var/run/sshd 0755 root root

4
I will check it in a few days, once I get one of my nodes out of production and 
do a fresh install.

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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/1814124

Title:
  sshd does not start after update

Status in openssh package in Ubuntu:
  Incomplete

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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