The host is sitting under my desk with the local network hostname “piguy”. http://piguy and http://highhands.piguy both work as expected. My server listens on port 8080, so I ran sudo tcpdump -i any port 8080 -n to monitor traffic and I see traffic from Cloudflare when accessing the main site, but no traffic when accessing the subdomain. At this point, if we assume Cloudflare is properly forwarding traffic, there might be some setting on the TLS setup I might be missing?
On my server, I edited ~/cloudflared/config.yml to have an ingress/hostname entry for handshigh.clusterfun.tv that matches the one for clusterfun.tv, then I rebooted the machine.
On Cloudflare dashboard, under SSL/TLS,Custom Hostnames, I added “handshigh.clusterfun.tv” and verified certificate status and hostname status are both Active
On the Cloudflare dashboard, I added a CNAME record for “*” with content “clusterfun.tv”
Is this what you meant by “setup the subdomain in the Tunnel’s settings in the Zero Trust Dashboard?”
I hadn’t touched the SSL/TLS part before your message, but even after my changes I still see the same behavior: I can only reach the clusterfun.tv site, but not handshigh.clusterfun.tv. I can hit both sites just fine on my local network, accessing the machine directly.
Any more suggestions? It seems like I am missing something really simple here.