Remote control / companion app not finding other players

Plex Players Mobile Devices
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Server Version#: 1.20.1.3252 (Linux)
Player Version#: 1.17.0.1376-439f8b7f (Mac)
Player Version#: 1.17.0.1376-439f8b7f (Windows)
Player Version#: 7.5 (iOS)
Player Version#: 8.5.1 (Android)

In my setup, my server is in a different network than my clients. I can play content fine on each of the desktop players, but recently I have not been able to remotely control the players from each other, as I cannot find them. The cast button stays gray and inactive even when toggling the “Advertise as a player” option.

First I thought that the problem is that my iOS client is on a wi-fi and cannot see my Windows player because of that. But then I tested with my Mac client and iOS client, both of which are in the same wi-fi, and should thus see each other fine. That doesn’t work either. The only two clients that can see each other are the Android and iOS clients when connected to the same wi-fi.

So how should this work? Why do the phone apps see each other as players when they cannot see for example the Mac? Any tips?

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∆∆∆ This is your problem.
Some of these client types cannot work with Plex companion, due to restrictions of the hardware platform.
They need a running Plex server in the same local network to act as a relay station.
This server doesn’t need to have any media content on it. It just needs to be present.

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