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Try using another pair of headphones to test if the problem is with the headphones. If the problem persists, you may need to contact their customer service for repair. It may be cheaper to simply replace the unit.
Make sure you read and find out what are the attributes of the MP3 files that your unit uses. For example, It might not play stereo files, or the quality of the MP3 might be too high. check you manual and make sure that you are using the correct attributes that the manufacture is calling for.
In any windows program, you should be able to go to My Computer, double click the icon for the extra drive, it may show up as an external usb device, rather than tight clicking and choosing copy, try dragging the itunes folder to the new destination, i.e. your usb device.
I had copied the songs into the voice folder on the drive. We moved them to be new folders along with the voice folder and it works fine. I just hope it lasts longer than some other peoples. I should have read up on this brand before I bought it.
What is happening when you turn the device on? Does it go on and then shut off? If so you will have to reformat the drive for the mp3 player. Simply plug the mp3 player in and click the drive that appears for the player. It should say this device needs to be formatted. Then just follow the steps. Keep in mind you will lost your songs. If the device stays on, do you see your first song on the list. If you do, try pushing the play button, (very last one on bottom) hard.