I'm not that invested in the having openssh-server installed but not
running use-case, but in general people do not like their local
configuration beeing overridden on package upgrades in this manner.

I could image people having it installed for the man-pages, or maybe
using other units for it (per VRF instances or something), having the
main service and socket units disabled, but I doubt that happens that
much in practice.

For me the biggest problem was the socket unit beeing re-enabled when I
had it disabled it but still running sshd.service (ie without socket
activation) - now you're unexpectidly switched back to using socket
activation - something I explicitly opted out of.

I could also see this causing problems if you have the socket unit
masked (dont see why you would want that however) but the the service is
enabled, now you are without sshd. Actually I think the postinst would
also fail in that case, as systemctl enable fails enabling masked units.

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https://bugs.launchpad.net/bugs/2059874

Title:
  on upgrade sshd-socket-generator conversion does not respect
  administrator intent

Status in openssh package in Ubuntu:
  Incomplete

Bug description:
  the openssh-server 1:9.6p1-3ubuntu11 postinst contains this code
  snippet:

  if [ "$action" == configure ]; then
    ..snip..
    if dpkg --compare-versions "$2" lt-nl 1:9.6p1-3ubuntu3~; then
      ..snip..
      if [ -d /run/systemd/system ]; then
        # Make sure ssh.service is disabled.
        systemctl unmask ssh.service
        systemctl disable --now ssh.service > /dev/null 2>&1

        # sshd-socket-generator is invoked on daemon-reload.
        systemctl daemon-reload
        systemctl enable ssh.socket
      fi
    fi
  fi

  This does not respect existing service and socket unit configuration,
  it effectively re-enables a disabled ssh.service (and even a masked
  one), and a manually disabled socket unit. I strongly suspect it does
  not respect systemd presets either.

  This is unexpected behaviour.

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