Well ... that configuration correction appears to have done the trick!
I'm very sorry to have inadvertently put you through this for the sake
an off-by-one-character invalid config. Re-reading the documentation I
can now see where the confusion occurred when crafting the config
originally, and I guess until now I was just unknowingly benefiting from
a non-spec compliant edge-case in the previous version or some other
chance alignment of stars. Cue the facepalm.

Here are the package versions and the updated config I've just tested
successfully with:

ii  network-manager  1.10.14-0ubuntu2
ii  systemd          237-3ubuntu10.24

/etc/systemd/resolved.conf.d/local.org.com.conf
[Resolve]
Cache=no
DNS=127.0.0.54
Domains=~local.org.com

Huge thanks for sticking with this, it's really appreciated, and happy
to provide any further information if you still feel there are questions
here that need answering, but if not, maybe we can call this a wrap?

-- 
You received this bug notification because you are a member of Desktop
Packages, which is subscribed to network-manager in Ubuntu.
https://bugs.launchpad.net/bugs/1829566

Title:
  network-manager 1.10.14-0ubuntu2 ignores systemd-resolved configured
  dns

Status in network-manager package in Ubuntu:
  Incomplete
Status in network-manager source package in Bionic:
  Incomplete

Bug description:
  On 18.04.2 the `upgrade network-manager:amd64 1.10.6-2ubuntu1.1
  1.10.14-0ubuntu2` lead to scoped DNS servers defined in
  `/etc/systemd/resolved.conf.d/*.conf` being ignored.

  Downgrading with `sudo apt-get install network-
  manager=1.10.6-2ubuntu1.1` has resolved the issue for now.

  Example systemd-resolved conf:

  [Resolve]
  Cache=no
  DNS=127.0.0.54
  Domains=~.local.org.com

  Where 127.0.0.54:53 is bound to a dnsmasq server capable of resolving
  queries in that subdomain.

To manage notifications about this bug go to:
https://bugs.launchpad.net/ubuntu/+source/network-manager/+bug/1829566/+subscriptions

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