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Yep all outbound ports are opened, per default. Tunnel does show as healthy in the dashboard. The cloudflared logs say the tunnel is established correctly but cloudflared cannot reach the application. I only have my home IP address set on inbound for both ssh as well as the application and port I'm trying to access. I'll look into this into more detail again in a couple hours and look at your and lilshalom's suggestions
Did you get it to work?
OMG I figured it out. It was actually my last comment that got me thinking in the right direction. The problem was that I was using the EC2 public IP address to point the tunnel to. EC2 also has an internal private IP address. Switched the tunnel to point to that, and it works! I felt like such a dummy when I thought about it. The tunnel is trying to hit the app internally. Why would it need to go out to the internet and retrieve a firewalled public address? Seems so obvious now.
Happens to the best of us! localhost or 127.0.0.1 should work too.
I've always personally hated localhost and just opt to use the IP directly, which I guess was my downfall this time :)