Dear Maintainer,

*** Reporter, please consider answering these questions, where appropriate ***

   * What led up to the situation?

Upgrading to the latest security update

   * What exactly did you do (or not do) that was effective (or
     ineffective)?

I used apt upgrade to install the security update available for
  openssh-server

   * What was the outcome of this action?

It overwrote /etc/ssh/sshd_config without promtping, erasing the custom settings
and almost locking me out as a result (my custom port setting was gone
as well as other changes I've made).

   * What outcome did you expect instead?

I expected to receive the usual prompt when a configuration file is
modified asking me what I want to do but there was none.

We'll need to be able to reproduce this problem before being able to do
anything about it.  (I have a modified /etc/ssh/sshd_config on my own
stable system and it wasn't overwritten on upgrade.)

Can you please provide a copy of your modified /etc/ssh/sshd_config,
along with the output of the relevant apt run (which should be preserved
in /var/log/apt/term.log)?

Hello Colin,

Here is the output of apt/term.log:

Log started: 2024-07-02  00:04:13
(Reading database ... 64456 files and directories currently installed.)
Preparing to unpack .../openssh-sftp-server_1%3a9.2p1-2+deb12u3_amd64.deb
...
Unpacking openssh-sftp-server (1:9.2p1-2+deb12u3) over (1:9.2p1-2+deb12u2)
...
Preparing to unpack .../openssh-server_1%3a9.2p1-2+deb12u3_amd64.deb ...
Unpacking openssh-server (1:9.2p1-2+deb12u3) over (1:9.2p1-2+deb12u2) ...
Preparing to unpack .../openssh-client_1%3a9.2p1-2+deb12u3_amd64.deb ...
Unpacking openssh-client (1:9.2p1-2+deb12u3) over (1:9.2p1-2+deb12u2) ...
Setting up openssh-client (1:9.2p1-2+deb12u3) ...
Setting up openssh-sftp-server (1:9.2p1-2+deb12u3) ...
Setting up openssh-server (1:9.2p1-2+deb12u3) ...
Replacing config file /etc/ssh/sshd_config with new version
rescue-ssh.target is a disabled or a static unit not running, not starting
it.
ssh.socket is a disabled or a static unit not running, not starting it.
Processing triggers for man-db (2.11.2-2) ...
Processing triggers for ufw (0.36.2-1) ...
Log ended: 2024-07-02  00:04:16

I've attached the sshd_config from my last week backup, I've just changed
the port number I use to a random one.

I had the same problem on 4 different servers I upgraded last night. Maybe
it's not related to openssh-server and I just noticed the problem on this
package...

Also note that I've recently enabled apt-listchange prompting on all these
servers:

cat /etc/apt/listchanges.conf
[apt]
frontend=pager
which=both
email_address=root
email_format=html
confirm=true
headers=false
reverse=false
save_seen=none
no_network=false

Here is the command I used to check and apply security updates:

sudo apt update && sudo apt dist-upgrade -V && sudo apt autoremove -y

Regards,

John Wellesz

While I upgraded other packages on another server today I noticed something
in my own behaviour: when there are modifications on a package file and I'm
asked what I want to do I always choose to open a terminal, then I use
vimdiff to merge the differences but sometimes, depending on the amount of
changes, I will pull the changes inside the new version, save that version,
exit the terminal and then choose "Install the maintainer's version"
(knowing that I modified it with the changes I wanted to keep)... So if the
packager uses the modified file stats/content as a basis it might explain
why it didn't prompt me... Could that be it?