I don't know whether sshd was running immediately after the install; I
noticed this problem a couple reboots after the install process was
complete. Are there any logs I can check that would be helpful to
reconstruct the sequence of events?

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https://bugs.launchpad.net/bugs/2023001

Title:
  sshd not starting because of missing /run/sshd

Status in openssh package in Ubuntu:
  Incomplete

Bug description:
  I recently upgraded from Ubuntu to 22.04 to 23.04 using do-release-
  upgrade (twice because I upgraded via 22.10). After doing so, sshd
  stopped working. The output of "journalctl -xeu ssh.service" includes
  the line:

  Jun 06 01:51:05 big-bucks sshd[4544]: Missing privilege separation
  directory: /run/sshd

  This fixed the problem: sudo mkdir /run/sshd

  It seems like either the upgrade sequence or the service startup
  sequence should have done this automatically.

  Currently running: ssh/lunar 1:9.0p1-1ubuntu8 all

  
  There was also a problem reported with /run/sshd on bug #1991283, but I guess 
the fix for that didn't prevent this.

  ProblemType: Bug
  DistroRelease: Ubuntu 23.04
  Package: ssh (not installed)
  Uname: Linux 6.2.6-76060206-generic x86_64
  ApportVersion: 2.26.1-0ubuntu2
  Architecture: amd64
  CasperMD5CheckResult: unknown
  CurrentDesktop: ubuntu:GNOME
  Date: Tue Jun  6 02:37:21 2023
  SourcePackage: openssh
  UpgradeStatus: Upgraded to lunar on 2023-06-04 (1 days ago)

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