DNS at systemd's 127.0.0.53 is ignoring some lookups

My resolv.conf file was pointing to the wrong place. This seems like a bug in Ubuntu as it happened on my laptop (the machine I first noticed this issue on) and on a fresh install of Ubuntu 18.04 Server.

The Default

$ ls -l /etc/resolv.conf

lrwxrwxrwx 1 root root 39 Apr 26 12:07 /etc/resolv.conf -> ../run/systemd/resolve/stub-resolv.conf

I deleted this and pointed to the correct file. After rebooting, this solved my issue. And I was even able to switch networks on my laptop and the DNS switched correctly. Of course when on external networks I can't resolve any of my local machines but that is expected. As soon as I switch back to my local network, all the local machines resolve correctly because my router is the DNS.

The Fix

$ sudo rm -f /etc/resolv.conf
$ sudo ln -s /run/systemd/resolve/resolv.conf /etc/resolv.conf
$ ls -l /etc/resolv.conf

lrwxrwxrwx 1 root root 32 May 29 08:48 /etc/resolv.conf -> /run/systemd/resolve/resolv.conf

$ sudo reboot

After that, everything worked as I expected and 127.0.0.53 is no longer being used at all.