Public bug reported:

Ubuntu 16.04.5, systemd 229-4ubuntu21.15

The latest systemd update has somehow changed the method it uses to
start 'ssh.service' i.e. 'sshd'. systemd fails to start sshd if
/etc/ssh/sshd_config contains "UsePrivilegeSeparation yes" and
/var/run/sshd/ does not already exist. Being as this is the default,
virtually EVERY Ubuntu 16.04 server in the world has
UsePrivilegeSeparation set to yes. Furthermore, at the time when the
user performs 'apt upgrade' and receives the newest version of systemd,
/var/run/sshd/ already exists, so sshd successfully reloads for as long
as the server doesn't get rebooted. BUT, as soon as the server is
rebooted for any reason, /var/run/sshd/ gets cleaned away, and sshd
fails to start, causing the remote user to be completely locked out of
his system. This is a MAJOR issue for millions of VPS servers worldwide,
as they are all about to get locked out of their servers and potentially
lose data. The next reboot is a ticking time bomb waiting to spring. The
bomb can be defused by implicitly setting 'UsePrivilegeSeparation no' in
/etc/ssh/sshd_config, however unsuspecting administrators are bound to
be caught out by the millions. I got caught by it in the middle of
setting up a new server yesterday, and it took a whole day to find the
source.

The appropriate fix would be to ensure that systemd can successfully
'start ssh.service' even when 'UsePrivilegeSeparation yes' is set.
systemd needs to test that /var/run/sshd/ exists before starting sshd,
just as the init.d script for sshd does. openssl could also be patched
so that UsePrivilegeSeparation is no longer enabled by default, however
that is not going to solve the problem for millions of pre-existing
config files. Only an update to openssl to force-override that flag to
'no' would solve the problem. Thus systemd still needs to be responsible
for ensuring that it inits sshd properly by ensuring that /var/run/sshd/
exists before it sends the 'start' command.

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

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https://bugs.launchpad.net/bugs/1811580

Title:
  systemd fails to start sshd at reboot

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