Public bug reported:

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)

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


** Tags: amd64 apport-bug kinetic

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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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