Two ideas, one of which I've already mentioned above:

1) You could migrate the address and port settings from sshd_config to
listen.conf _before_ installing the new sshd_config, so that they will
be preserved even if the config gets replaced with the vendor version
because of a merge conflict like it was in my case.

2) You could have the preinst script detect if the service is currently
enabled and going to be switched to the socket, and if so, pop up an
interactive warning explaining the change and telling the user where to
look for more info, like many other packages do, e.g., the Docker
restart warning. If you'd like you can only display the warning if there
are address or port settings specified in the user's old sshd_config.

Finally, as I said in my original report, "I don't know what the right
answer is here." What I "expect [you] to do" when someone points out an
issue like this is to put some thought into how to make it better rather
than seeming to imply that the person who reported the issue is being
petulant. Putting it another way: neither of the ideas above is rocket
science, and I'm not sure why I should have to be the one to think of
them, rather than the people who are, you know, being paid to do that.

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https://bugs.launchpad.net/bugs/1990863

Title:
  conversion from sshd service to socket is too bumpy

Status in openssh package in Ubuntu:
  New

Bug description:
  During upgrade from Jammy to Kinetic, I get asked what to do because
  my sshd_config has been modified. I say to do a 3-way merge. It says
  3-way merge fails. I shrug, figure I'll just restore my customizations
  with Ansible after the upgrade like I always do, and tell it to use
  the vendor version of the file. This removes my custom Port settings,
  so they are not migrated over to the ssh.socket settings like
  https://discourse.ubuntu.com/t/sshd-now-uses-socket-based-activation-
  ubuntu-22-10-and-later/30189 says they would be. I subsequently run my
  Ansible which restores the customizations and enables the ssh service,
  but now ssh.service and ssh.socket are enabled at the same time, sshd
  isn't listening on my specified ports, and everything is a mess. I've
  never used socket-based activation before and have no idea how to
  configure it so now I have to go reading man pages, Googling all over
  the place, and generally struggle to figure out what the heck is going
  wrong.

  I don't know what the right answer is here, but I really feel like
  some effort needs to be put into figuring out a smoother transition
  for people who are upgrading to Kinetic.

  ProblemType: Bug
  DistroRelease: Ubuntu 22.10
  Package: openssh-server 1:9.0p1-1ubuntu6
  ProcVersionSignature: Ubuntu 5.19.0-15.15-generic 5.19.0
  Uname: Linux 5.19.0-15-generic x86_64
  ApportVersion: 2.23.0-0ubuntu2
  Architecture: amd64
  CasperMD5CheckResult: unknown
  CurrentDesktop: ubuntu:GNOME
  Date: Mon Sep 26 11:41:58 2022
  InstallationDate: Installed on 2019-08-16 (1136 days ago)
  InstallationMedia: Ubuntu 19.04 "Disco Dingo" - Release amd64 (20190416)
  SourcePackage: openssh
  UpgradeStatus: Upgraded to kinetic on 2022-09-24 (1 days ago)

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