I see on review that your patch does fix any broken override files, by
virtue of replaying the same upgrade code if upgrading from 1ubuntu6.
There are some corner cases where that might not be desirable, but as
these are all pre-release versions I think it's ok to ignore these in
favor of landing the fix more quickly.

** Changed in: openssh (Ubuntu)
       Status: Triaged => In Progress

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https://bugs.launchpad.net/bugs/1991199

Title:
  sshd port migration is missing two config lines from jammy to kinetic

Status in openssh package in Ubuntu:
  In Progress
Status in systemd package in Ubuntu:
  Invalid

Bug description:
  The automatic migration script from jammy to kinetic generates a
  invalid file for sshd that systemd refuses to read. Manual addition of
  two lines is required for a functional sshd with a custom port.

  This bug can be considered the opposite of
  https://bugs.launchpad.net/ubuntu/+source/openssh/+bug/1990863 . They
  want to have sshd keep managing the socket while I want to try letting
  systemd do that.

  $ lsb_release -rd
  Description:    Ubuntu Kinetic Kudu (development branch)
  Release:        22.10

  $ apt-cache policy openssh-server
  openssh-server:
    Installed: 1:9.0p1-1ubuntu6
    Candidate: 1:9.0p1-1ubuntu6
    Version table:
   *** 1:9.0p1-1ubuntu6 500
          500 https://gpl.savoirfairelinux.net/pub/mirrors/ubuntu kinetic/main 
amd64 Packages
          100 /var/lib/dpkg/status

  $ apt-cache policy systemd
  systemd:
    Installed: 251.4-1ubuntu6
    Candidate: 251.4-1ubuntu6
    Version table:
   *** 251.4-1ubuntu6 500
          500 https://gpl.savoirfairelinux.net/pub/mirrors/ubuntu kinetic/main 
amd64 Packages
          100 /var/lib/dpkg/status

  # Instructions

  - Configure /etc/ssh/sshd_config to port 2222 in 22.04
  - Upgrade to 22.10 with sudo do-release-upgrade -d
  - Accept overwriting /etc/ssh/sshd_config with the new version
  - Attempt to ssh into the machine

  # Expected behavior

  systemd should listen on port 2222 and start sshd.

  $ cat /etc/systemd/system/ssh.socket.d/addresses.conf
  [Socket]
  ListenStream=
  ListenStream=2222

  $ systemctl status ssh.socket
  ● ssh.socket - OpenBSD Secure Shell server socket
       Loaded: loaded (/lib/systemd/system/ssh.socket; enabled; preset: enabled)
      Drop-In: /etc/systemd/system/ssh.socket.d
               └─addresses.conf
       Active: active (running) since Thu 2022-09-29 02:08:56 EDT; 9min ago
        Until: Thu 2022-09-29 02:08:56 EDT; 9min ago
     Triggers: ● ssh.service
       Listen: [::]:2222 (Stream)
        Tasks: 0 (limit: 19047)
       Memory: 8.0K
          CPU: 923us
       CGroup: /system.slice/ssh.socket

  Sep 29 02:08:56 daniel-desktop2 systemd[1]: Listening on OpenBSD
  Secure Shell server socket.

  # Actual behavior

  Port 2222 refuses any connection. Systemd fails to parse the
  automatically generated file:

  $ systemctl status ssh.socket
  ● ssh.socket - OpenBSD Secure Shell server socket
       Loaded: loaded (/lib/systemd/system/ssh.socket; enabled; preset: enabled)
      Drop-In: /etc/systemd/system/ssh.socket.d
               └─addresses.conf
       Active: active (listening) since Thu 2022-09-29 01:51:57 EDT; 16min ago
        Until: Thu 2022-09-29 01:51:57 EDT; 16min ago
     Triggers: ● ssh.service
       Listen: [::]:22 (Stream)
        Tasks: 0 (limit: 19047)
       Memory: 8.0K
          CPU: 982us
       CGroup: /system.slice/ssh.socket

  Sep 29 01:51:57 daniel-desktop2 systemd[1]: Listening on OpenBSD Secure Shell 
server socket.
  Sep 29 01:56:23 daniel-desktop2 systemd[1]: 
/etc/systemd/system/ssh.socket.d/addresses.conf:1: Assignment outside of 
section. Ignoring.

  $ cat /etc/systemd/system/ssh.socket.d/override.conf
  ListenStream=2222

  # Analysis

  The migration script must be missing the `[Socket]` line and the next one. 
sshd works after I added those two lines manually. Either the migration script 
never worked or systemd changed the syntax in the meantime.
  --- 
  ProblemType: Bug
  ApportVersion: 2.23.0-0ubuntu2
  Architecture: amd64
  CasperMD5CheckResult: unknown
  DistroRelease: Ubuntu 22.10
  MachineType: ASUSTeK COMPUTER INC. K30BF_M32BF_A_F_K31BF_6
  Package: systemd 251.4-1ubuntu6
  PackageArchitecture: amd64
  ProcKernelCmdLine: BOOT_IMAGE=/vmlinuz-6.0.0-060000rc7-generic 
root=UUID=29b85a8a-08f8-42be-8629-fb6e88d149d6 ro text pcie_port_pm=off 
resume=UUID=21d61484-fe9b-4310-9390-d5f5d17510d8
  Tags:  kinetic
  Uname: Linux 6.0.0-060000rc7-generic x86_64
  UpgradeStatus: Upgraded to kinetic on 2022-09-29 (0 days ago)
  UserGroups: N/A
  _MarkForUpload: True
  dmi.bios.date: 05/19/2017
  dmi.bios.release: 4.6
  dmi.bios.vendor: American Megatrends Inc.
  dmi.bios.version: 0704
  dmi.board.asset.tag: To be filled by O.E.M.
  dmi.board.name: K30BF_M32BF_A_F_K31BF_6
  dmi.board.vendor: ASUSTeK COMPUTER INC.
  dmi.board.version: Rev X.0x
  dmi.chassis.asset.tag: Asset-1234567890
  dmi.chassis.type: 3
  dmi.chassis.vendor: Chassis Manufacture
  dmi.chassis.version: Chassis Version
  dmi.modalias: 
dmi:bvnAmericanMegatrendsInc.:bvr0704:bd05/19/2017:br4.6:svnASUSTeKCOMPUTERINC.:pnK30BF_M32BF_A_F_K31BF_6:pvrSystemVersion:rvnASUSTeKCOMPUTERINC.:rnK30BF_M32BF_A_F_K31BF_6:rvrRevX.0x:cvnChassisManufacture:ct3:cvrChassisVersion:skuSKU:
  dmi.product.family: Desktop
  dmi.product.name: K30BF_M32BF_A_F_K31BF_6
  dmi.product.sku: SKU
  dmi.product.version: System Version
  dmi.sys.vendor: ASUSTeK COMPUTER INC.
  modified.conffile..etc.systemd.logind.conf: [modified]
  modified.conffile..etc.systemd.sleep.conf: [modified]
  mtime.conffile..etc.systemd.logind.conf: 2022-09-29T00:25:31.556533
  mtime.conffile..etc.systemd.sleep.conf: 2022-09-29T00:27:46.773607

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