IIUC the problem is the package split of sd-resolved, which was still
part of the combined "systemd" binary package in Jammy. When people
upgrade to Noble "systemd" gets unconfigured, dropping any cache/state
about systemd-resolved.service, then the "systemd-resolved" binary
package gets (force)installed either as a Recommends or by an update-
manager quirk. But due to the lost state, debhelper will start & enable
the systemd-resolved.service, even if it was masked or disabled before.
Breaking people's custom setup.

If this assumption is correct, the problem should not happen when
upgrading from Noble to Oracular (or above) because state about systemd-
resolved.service is handled properly when upgrading the "systemd-
resolved" binary package... (to be confirmed), so would only affect
Jammy->Noble upgrades.

I looked into
https://manpages.debian.org/testing/debhelper/dh_installsystemd.1.en.html
and https://manpages.debian.org/testing/init-system-helpers/deb-systemd-
helper.1p.en.html but feel like those cannot really do what we need here
(considering the package-split edge case). So we might need some hand-
crafted .postinst to restore systemd-resolved.service state in deb-
systemd-helper. The auto-generated systemd-resolved (DEBIAN/postinst of
the binary package), might be a good starting point.

-- 
You received this bug notification because you are a member of Ubuntu
Touch seeded packages, which is subscribed to dnsmasq in Ubuntu.
https://bugs.launchpad.net/bugs/2078555

Title:
  Upgrading from 22.04 to 24.04.01 breaks dnsmasq

Status in Ubuntu:
  Triaged
Status in dnsmasq package in Ubuntu:
  Triaged
Status in systemd package in Ubuntu:
  Triaged
Status in ubuntu-release-upgrader package in Ubuntu:
  Triaged

Bug description:
  Was running Ubuntu 22.04 as home gateway/firewall with dnsmasq as
  dns/dhcp server. Previous upgrade from Ubuntu 20.04 to 22.04 had
  worked without issue.

  After the upgrade to 24.04.01, systemd-resovled was automatically
  enabled. The result was that after a reboot, dnsmasq failed to start,
  as systemd-resolved had already bound to the necessary port. This in
  turn meant that my entire home network lost connectivity as it was
  dependant on dnsmasq running to provide both correct dns and dhcp
  functionality.

  Ideally, during the upgrade process, a check should be made for if
  another dns/dhcp service is already enabled, and if so, not enable
  systemd-resolved.

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