CADDY/cloudflare - Not understanding why I am getting an SSL handshake failure

[cribbageSTARSHIP]

Good day everyone. I am using the caddy plugin and am able to access my opnsense gui (only from inside my LAN) from my .com. I have 3 domains ( home/prod/testing ) that I want to have services work with. the OPN GUI is on my prod domain and it works. I tried two other services (qbittorrent on http, and portainer on https) and neither work. with my cloudflare SSL/TLS encryption set to full it shows the two failures are due to SSL handshake failed Error code 525. With it turned to flexable it fails due to ERR_TOO_MANY_REDIRECTS.



Im not sure what to look for in diagnosing this issue. Any guidance would be great. Thank you!

[OmnomBánhmì]

This is a little hard to diagnose. :) Try testing with these methods and post/report the responses you get, for each of your subdomains:

$ curl -v https://prod.youraddre.ss -o /tmp/test

This will give you metadata about the connection, and redirects will show. You may look for subjectAltName, Host and location values (and others).

Web-based tests do not show as much detail, however https://deref.link/ and https://wheregoes.com/ may help too.