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dynamic ip, caddy, ssl - GordonShumway - 2025-10-24

I have been port forwarding 8096 through my firewall for external watching of JF and using the JF authentication, but I would like to figure out reverse proxy.  I have a dynamic DNS (freemyip.com) and would like to have jellyfin.mydomain.freemyip.com resolve to my internal IP of 192.168.0.158:8096 (the JF server).

My JF server does not have an ssl certificate.  When I tried to create a reverse proxy entry in the Caddyfile my firewall is showing two things: first every http request from ever external device (i.e. my Android, my friend's laptop) is being rewritten to https and second that /var/log/messages is showing complaints about not having set an email address for Zerossl so I'm pretty sure I am missing some parts here.

If every web request is going to rewrite to https should I get an ssl cert for JF before I play with Caddy? O is it the Caddy instance that needs the ssl cert?  I am assuming that all requests will now be https, at least from the firewall to Caddy, but what about from Caddy to JF?  Since I am "not planning" to expose any other services I don't have a problem with installing Caddy on the JF server.  Or should it be on a separate server/docker?  I have seen a few videos on this and I'm sorry to say that although they claim to be for beginners they are poorly orchestrated (yeah, I'm an IT guy and I know how to write doc to communicate complex ideas to noobs).  Any help would be appreciated.

GS