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iPod question for any Apple guys out there.

So, I have a 2nd generation iPod Touch, because it works great and I’m not going to waste a whole paycheck on replacing it. I also drive for Lyft, and as such, I have a playlist of all my non-explicit music. It’s 555 songs. However, when I set it to shuffle, it will suddenly show “1/553" instead of playing everything. I know that one of the two problem songs is “Children’s Story” by Slick Rick, and if I play that one first and THEN turn on shuffle, it will say 1/554. However, it and the other undetermined song will never, ever play unless I choose them manually. So... What gives? How do I make it play ALL my music on shuffle?

Side note: “Living in Oblivion” by Ultravox will play about 1/5 the time, but every other time it’s either just a couple minutes of silence or it skips immediately. I don’t care too much about that one, though, as I’m used to songs just never playing. (“Wild Boys” by Duran Duran and Big Country’s self-titled track have never played once.)


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