Another problem is that while showing this prompt, you can't log in via
SSH. If you leave your upgrade unattended and lose the connection to
your server, you won't be able to log in via SSH again to
complete/continue the upgrade.

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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:
  Fix Committed
Status in openssh source package in Focal:
  Fix Committed
Status in openssh package in Debian:
  Fix Released

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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