Figured it out. The ENV stuff was a red herring. It was a local network interface issue.

Even though I had rebooted the machine a few times the root issue was that I could not access the machine unless I was going over Tailscale. I could not ping the IP. After realizing this I figured the issue was a LAN issue. Still not 100% sure what happened but everything works as expected.

I don't think the .env file is used any longer because the migrated file I have is pretty old. I believe its deprecated now.