Traefik `Path` working for one container but not another (+ Cloudflare Tunnel)

Yes, Traefik will just proxy/forward the request.

But Portainer doesn’t know what to do with a request to path /portainer. It expects an initial request to /.

When you publish the port of Portainer directly to host and send the request to it, it will also respond with 404 for /portainer, without Traefik.