HTTPS proxying working partially

I am currently using tailscale to expose my systems to the internet for both and should they both point to the same CNAME records. However when you access it works just fine loads without any issues. times out for no apparent reason.

Is there any reason why doesn’t work? When I was simply port forwarding everything worked but now I’m not really sure why it doesn’t work since the nginx rules are the same and besides where the requests come from nothing has changed.