I think I may have figured it out. Let me preface this by saying when it comes to SSL certificates and HTTPS and all, I’m extremely dumb. I have muddled my way through this far.
I think my issue is I’ve configured NGINX to open a secure port when CADDY is already doing that. Here is how I imagine it,
Outside Request to Caddy, “Hey I have a secure request, please process.”
Caddy, “Yes this is secure, I will unlock it with my key and see where it should go. Ok, I see the message and it should go down my friend NGINX.”
Caddy to Nginx, “Here you are, I’ve already opened this message for you. What is your response?”
Nginx to Caddy, “Here you go, this is what I need sent back.”
Caddy, Thanks! I’ll lock this up with my key before I do.
Caddy to Outside Requestor: Here you are, your private message from Nginx.
Is that anything close to what’s going on?