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I have followed that guide which let me to a few GitHub issues.
Here is what I have put in my config:
I have also added all Cloudflare IPs in Jellyfin's known proxies:
Yet, I'm still not seeing the real IPs.
You should only need to add the IP of the last proxy before reaching Jellyfin, which would be Caddy.
Using a whitelist in this manner with cloudflare may be challenging as this list can potentially change. They do have means to query it though. https://developers.cloudflare.com/api/operations/cloudflare-i-ps-cloudflare-ip-details Additionally, have you considered ipv6 support?
if you haven't solved the problem yet, I would consider switching to Apache for your reverse proxy and using mod_remoteip.
I might have to switch, as much as I like the simplicity of Caddy, I keep running into issues like this unfortunately.