SOLVED: SSL Handshake Failed on Fire TV

[Linseed9747]

Did any of the cert authorities change in your cert?  Does FireOS trust your cert?  Are you providing the full trust chain in your reverse proxy config?

For full transparency, I only understand your questions enough to get myself in trouble.  Also, my cert provider makes the process fairly point-and-click at this point; that, in and of itself, is making me less competent to answer your questions, but I will give it a go.

1) Did any of the cert authorities change in your cert?

I believe so (assuming I understand your question).  I deleted the old expired certificate from my server to make sure nothing was attempting to use it when I started troubleshooting this issue.  So I don't know how to go back and compare, but I did have the impression at the time that the CA changed.  I believed I saved the old certificate somewhere if you need me to go back an look at it.  But to be honest I may be misunderstanding what you are asking lol

2) Does FireOS trust your cert?

When inputting the server url on Fire TV Stick jellyfin app, receiving a handshake error.  All tested Fire Sticks had previously been working properly, so I assume the answer is no, Fire OS does not trust the cert?  Again, I may be misunderstanding your question but I do know the other services I run using this wildcard certificate are working properly.

3) Are you providing the full trust chain in your reverse proxy config?

I am using a Synology NAS stock reverse proxy.  I remember reading at some point that Synology may be using a version of NGINX at the core, but Synology doesn't expose a lot for me to look at.  When I was prompted, I did add the private key, certificate, and intermediate certificate.  Is this what you are asking?

I'm willing to be putty in your hand if you're willing to help mold me