On Fri, 2025-01-17 at 17:08 +0800, Tianyu Chen wrote:
> When SSHing to my server, I've received the following message:
> 
>       1 updates could not be installed automatically. For more details,
>       see /var/log/unattended-upgrades/unattended-upgrades.log
> 
> The relevant log entries are:
> 
>       2025-01-17 06:54:23,555 INFO Starting unattended upgrades script
>       2025-01-17 06:54:23,557 INFO Allowed origins are: 
> origin=Debian,codename=bookworm,label=Debian, 
> origin=Debian,codename=bookworm,label=Debian-Security, 
> origin=Debian,codename=bookworm-security,label=Debian-Security
>       2025-01-17 06:54:23,557 INFO Initial blacklist: 
>       2025-01-17 06:54:23,557 INFO Initial whitelist (not strict): 
>       2025-01-17 06:54:26,110 WARNING Package dnsmasq has conffile prompt and 
> needs to be upgraded manually
>       2025-01-17 06:54:26,730 INFO package dnsmasq not upgraded
>       2025-01-17 06:54:27,035 INFO No packages found that can be upgraded 
> unattended and no pending auto-removals
>       2025-01-17 06:54:27,050 INFO Package dnsmasq is blacklisted.
> 
> When attempting to upgrade dnsmasq manually, I encounter a configuration file 
> prompt:
> 
>       Preparing to unpack .../dnsmasq_2.90-4~deb12u1_all.deb ...
>       Unpacking dnsmasq (2.90-4~deb12u1) over (2.89-1) ...
>       Setting up dnsmasq (2.90-4~deb12u1) ...
>       Installing new version of config file /etc/default/dnsmasq ...
> 
>       Configuration file '/etc/dnsmasq.conf'
>        ==> Modified (by you or by a script) since installation.
>        ==> Package distributor has shipped an updated version.
>          What would you like to do about it ?  Your options are:
>           Y or I  : install the package maintainer's version
>           N or O  : keep your currently-installed version
>             D     : show the differences between the versions
>             Z     : start a shell to examine the situation
>        The default action is to keep your current version.
>       *** dnsmasq.conf (Y/I/N/O/D/Z) [default=N] ? D
> 
> This behavior is unexpected because the dnsmasq.conf change caused the
> package cannot be upgraded automatically. So I've raised the severity to
> serious.

I tried to reproduce your finding following these steps

   - set up a fresh minimal Debian stable system
   - install dnsmasq_2.89-1_all.deb and dnsmasq-base_2.89-1_amd64.deb
   - upgrade the system, which results in installing
     dnsmasq_2.90-4~deb12u1_all.deb and
     dnsmasq-base_2.90-4~deb12u1_amd64.deb

All went flawlessly:

   Preparing to unpack .../dnsmasq-base_2.90-4~deb12u1_amd64.deb ...
   Unpacking dnsmasq-base (2.90-4~deb12u1) over (2.89-1) ...
   Preparing to unpack .../dnsmasq_2.90-4~deb12u1_all.deb ...
   Unpacking dnsmasq (2.90-4~deb12u1) over (2.89-1) ...
   Setting up dnsmasq-base (2.90-4~deb12u1) ...
   Removing obsolete conffile /etc/dbus-1/system.d/dnsmasq.conf ...
   Setting up dnsmasq (2.90-4~deb12u1) ...
   Installing new version of config file /etc/default/dnsmasq ...
   Installing new version of config file /etc/dnsmasq.conf ...
   Installing new version of config file /etc/init.d/dnsmasq ...
   Installing new version of config file /etc/resolvconf/update.d/dnsmasq ...
   Installing new version of config file /etc/sv/dnsmasq/run ...
   Processing triggers for dbus (1.14.10-1~deb12u1) ...

Therefore I am inclined to assume /etc/default/dnsmasq has been changed
in a way dpkg does not know how to handle automatically, and not being
able to force an upgrade is a reasonable safety measure.

Overall, the issue you encountered to me seems behaviour to be expected
and I tend to at least downgrade the bug's severity, if not close it.

Best,
Sven

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