I'm able to easily reproduce this in lxc using the steps provided.

** Changed in: openssh (Ubuntu)
   Importance: Undecided => High

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

** Tags added: server-next

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https://bugs.launchpad.net/bugs/1861472

Title:
  upgrade from fresh bionic to focal needlessly prompts user

Status in openssh package in Ubuntu:
  Triaged

Bug description:
  Upgrading from a fresh 18.04 LTS install to focal unexpectedly prompts
  for how to handle a change to /etc/ssh/sshd_config

  To reproduce the issue:

  lxc launch ubuntu:18.04 u18
  lxc exec u18 -- bash
  # within container
  do-release-upgrade -d
  # select restart services when prompted

  Eventually you'll be prompted to accept changes to
  /etc/ssh/sshd_config or not because of "local changes".

  Thanks

  ProblemType: Bug
  DistroRelease: Ubuntu 20.04
  Package: openssh-server 1:8.1p1-5
  ProcVersionSignature: Ubuntu 4.15.0-62.69-generic 4.15.18
  Uname: Linux 4.15.0-62-generic x86_64
  ApportVersion: 2.20.11-0ubuntu16
  Architecture: amd64
  Date: Fri Jan 31 03:37:55 2020
  ProcEnviron:
   TERM=rxvt-unicode-256color
   PATH=(custom, no user)
   LANG=C.UTF-8
  SourcePackage: openssh
  UpgradeStatus: Upgraded to focal on 2020-01-31 (0 days ago)

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