Multiplayer with friend not working?

Friend of mine just got Elden Ring and is new to the souls games in general. I’d thought I’d show him the ropes, so we both made new characters to ensure our SL is the same.

We also made sure to use the same multiplayer passwords (we triple checked via Discord screen sharing), activated the same Stake of Marika, made sure we were both online and have cross-region turned on.

Any clue what else we could have missed?