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UM i dont know if this will work but connect your iPod to the iTunes store with your UBS cord and something will pop up click yes something else will pop up click no then leave it an hour and i think it will work .
To do this you must go to the screen that says the time and "Slide to unlock"<br />
1. Go to that menu<br />
2. Double tap the home botton (The circle with a square in it).<br />
3. Now you can change the volume and song and pause or play.
it may be that you have the repeat option turned on and dont know it. try going into options or where ever the repeat option is located and switch it off. you also might want to try and select a different song in the album to see if the repeat is on. hope this helps
Check that when you plug your iPod in that it isn't selected to "Shuffle," play which can happen if you are expecting to go through songs. There is also another reason and one I didnt know about until I took my iPod Classic back to my retailer thinking there was a problem;
If the songs on your iTunes or default device isn't an AAC file the iPod will fail to play it. On MAC systems simply click the file that you want to put onto your iPod, right click and scroll to "Get Info." If the file doesn't say it is an AAC file it won't play on your iPod. Scroll further down on the list to "Create AAC version." This takes milliseconds, doesn't affect the sound quality but condenses the data fit for the iPod Classic. Once that's done you can add any song you like.
Generally when you put a CD into a MAC it will automatically change the AIFF files into AAC which means you don't need to manually convert. AAC is usually needed when individual tracks are called up and put onto your iPod. I hope this helps you - it drove me nuts until I found out about the AAC.