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Happy to report the update to IOS 15 on my iPhone solved the problem I was having😎

Will do the update to IOS 15 and let you know if that solves the problem. Either way I am overdue for a new iPhone

It's also worth noting I can duplicate the problem with playing multiple songs from the app from the adapter in my truck which again has no problem playing multiple songs directly from an iTunes playlist

Yes and yes to your first two questions. However there is no problem playing repetitive songs when playing from an iTunes playlist vs the walkup music app.

I'm using an iPhone8 so I think it may be the phone

No, the iPhone is plugged into the stereo sound system. No Bluetooth capability.

And I don't have the problem without the plug which suggests it's an iPhone issue and not the app.

Any suggestions?

I'm still using IOS 14 on iPhone. Do I need to update to IOS 15?

Has this problem been fixed? I an having a similar problem with the app. If one walkout song plays the next one won't play without closing the app and re-entering and that doesn't always work either.

Also have problems getting pregame, inning break and situations songs to play at all.