Ok figured it out. Whoever is doing development on Ubuntu needs to stop changing things around so much that pretty much any documentation you look at is obsolete.
So the issue was that in 18.04 resolv.conf is no longer used and instead netplan is used. Fine. No problem.
But then why the heck not just use the same old symlink location?
Code:
resolv.conf -> ../run/systemd/resolve/stub-resolv.conf
For some reason that is still the symlink, YET netplan edits this file instead
Code:
resolv.conf -> /run/systemd/resolve/resolv.conf
So you cant just use netplan to edit the DNS, you have to also change the symlink location. Now that I pointed it to the correct file that netplan actually does modify everything is working.
Frustrating to spend a day debugging issues that were really in my opinion created unnecessarily. I am all for improving and making things better, but in this case here, seeing how netplan edits a file that is not actually used for config.. its like someone dropped the ball at the last yard.
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