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I have an ARC Ultra in my living room and a Ray in my bedroom.

When I use the iOS app to try to start music in the bedroom, I get an error the like “The connection to the server timed out” or “Something went wrong.”

When I use the app to try to start music everywhere, it plays in the living room but not the bedroom.

Once I have it playing in the living room, I can use the voice assistant to group everywhere, and once it’s playing everywhere I can stop it in the living room and keep playing it in the bedroom.

What’s going on? Can I fix it or do I just live with the workaround?

Maybe try a refresh of your local stuff.

Power down all Sonos, reboot router and phone, power up the Sonos and try again.