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So, since one of the recent app updates on iOS the sorting direction of songs in my playlist on carplay is now similar to what I see on my iOS device. So, I thought the entire problem was fixed. Turns out, it starts playing songs in the opposite direction. So, if I play song #2 for example, it plays song #1 after that and then stops. If I start with song #1, it will stop right after that.
Would be awesome if someone could fix this teeny tiny problem to finally get this to work in carplay. It's been a while and still no solution to play my playlists the way I normally play them...