Hi @thebadwolf79, welcome to the Caddy community!
Plex is indeed a notorious beast to proxy into a subfolder. It rears its ugly head occasionally around the Caddy forums - I use it myself, as well - but I’ve never personally managed to neatly partition it without just giving it a subdomain. I’m sure it’s possible…
@alexandzors has a great Caddyfile example.
I use an only slightly different version:
plex.example.com {
redir {
if {path} is /
/ /web/
}
proxy / plex:32400
}
But more generally speaking, I rely on https://app.plex.tv/.