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I'm having problems with this. I have a large music collection on a usb drive. It's all in various folders organized by album. I had iDrive all set so that it would randomize the whole shebang, and it has worked great for a couple months now. But driving home today, it got stuck playing songs only from one folder. This had a checkbox on it. I'm now able to get it to start random play from another folder, but I can't figure out how get it to randomize the entire drive.
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