Update: The app is downloaded and set up, but it stops automatically when I try to start it. It bugs out between “deploying” and “stopped”. Any thoughts?
Could this be related to how I have the network configured?
If your networking tab is configured it the way @neofusion suggested, then it should be fine (proof being that you are able to reach your nas locally, and the nas is able to reach the apps to download them)
I’d recommend checking your configurations for tailscale itself, checking tailscale’s logs etc.
When I check Tailscale’s logs there’s nothing in regards to the TrueNAS system. I do believe it’s something related to the network configuration for the app. I might need assistance to verify if it’s correct or not.
Got it working! After some research I found adding /32 instead of /24 is what fixed it. Thanks to everyone that helped me out in this thread, I’m learning a lot! 
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