It happens on Wifi and on cellular. Bu tI will do it on cellular as well now to provide those logs as well. The setting you mentioned is currently turned on as well.
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I just completed trying it multiple times again getting the same response to check the app. I also connected via bluebook to my car during the same time and allowed it to play.
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My pandora link recently stopped working and shows as "check app" on the screen when plugged into my Kenwood DDX492 head unit. If I unplug and use just bluetooth it works fine.
Moderator Edit: Changing title for clarity
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