> Please add to the Test Plan to verify that there are no conffile
prompts in the at-risk upgrade paths.

Added. Thanks.

** Description changed:

  [Impact]
  
  There is currently no comment in the default /etc/ssh/sshd_config
  explaining that a systemctl daemon-reload is needed for changes to Port
  etc. to take effect when systemd socket activation is used (the default
  on Ubuntu).
  
  Users may change e.g. Port in  /etc/ssh/sshd_config and expect systemctl
  restart ssh.service to reflect the change, but this will not work.
  
  [Test Plan]
  
- The proposed fix here is to improve the documentation by adding a
+ 1. The proposed fix here is to improve the documentation by adding a
  comment above the default Port setting in /etc/ssh/sshd_config. Hence,
  the test is to simply install openssh-server from noble-proposed, and
  verify that the comment is there.
+ 
+ 2. Because the patch changes the default sshd_config, and
+ debian/openssh-server.ucf-md5sum needs to be updated when this happens,
+ an upgrade from noble to oracular should be done after installing
+ openssh-server from noble-proposed. If a debconf prompt is shown, then a
+ mistake was made in recording the checksums. Otherwise, they are
+ correct.
  
  [Where problems could occur]
  
  There is low technical risk, but we should be sure that the
  documentation is clear and improves the experience of users. It could be
  harmful if the documentation accidentally makes things worse, or is just
  confusing.
  
  Also, a packaging quirk of openssh-server is that checksums of the
  patched sshd_config (along with certain settings tweaked) need to be
  recorded in debian/openssh-server.ucf-md5sum to avoid unnecessary
  debconf prompts on upgrades. I have updated those checksums, but if they
  are incorrent, then in future upgrades users might see an unnecessary
  debconf prompt about /etc/ssh/sshd_config.
  
  [Original Description]
  
  Changing the Port directive in sshd_config and restarting ssh.service is
  without effect, sshd keeps listening to port 22.
  
  Also mentioned in https://discourse.ubuntu.com/t/sshd-now-uses-socket-
  based-activation-ubuntu-22-10-and-later/30189/32
  
  Steps to reproduce:
  1. Install Ubuntu 24.04 LTS
  2. Change Port directive in /etc/ssh/sshd_config to Port 2233
  3. Restart ssh.service
  4. Observe sshd still listening to port 22
  
  Expected behaviour: sshd changes port to 2233
  
  Actual behaviour: sshd keeps listening to port 22

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https://bugs.launchpad.net/bugs/2069041

Title:
  Changing Port in sshd_config requires calling systemctl daemon-reload

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