1: not very hard actually, the hardest part is gettin the cert onto your other devices x3
all you need to do is add each subdomain to the cert, add ssl_certificate and ssl_certificate_key to the http block, then enable ssl for each subdomain, like so:

http {
    # cert
    ssl_certificate /etc/nginx/public.crt;
    ssl_certificate_key /etc/nginx/private.key;
    server {
        listen       12345:443 ssl;
        server_name  pi.hole;

        location / {
                proxy_pass http://localhost:80;
        }
    }
    server {
        listen       12345:443 ssl;
        server_name  fox.hole;

        location / {
                proxy_pass http://localhost:621;
        }
    }
}

2: correct, all traffic goes through nginx.

Hey there,

I have somewhat of a similar setup. I use Nginx Proxy Manager and AdGuard Homes rewrites to do the same thing as you.

As for Question 1: Creating self-signed certs is pretty straightforward. I followed this tutorial by Christian Lempa: https://youtu.be/VH4gXcvkmOY He also has a good writeup on his GitHub: https://github.com/ChristianLempa/cheat-sheets/blob/main/misc/ssl-certs.md How to import the certs into Nginx, I don’t know, but I think that’s easy to lookup online.

Regarding Question 2: My understanding is that all traffic goes through the Reverse Proxy.

I hope I could help, let me know if you have any more questions.

• in order to add certs you would need a certificate authority, capable of setting up a proper certificate chain. There are several, ranging from the super simple like mkcert to full scale management tools like openCA. The second step is harder and require your consuming apps (the devices and apps that connects to your jellyfin) to trust your CA. An alternative would be to have a proper domain and use LetsEncrypt to get a cert, then trust will work out of the box, but it might also leak information about your private infrastructure.

• traffic will go through your proxy