Nano 4GB - songs wont transfer from itunes

Out of the 500 or songs Ive downloaded, it only puts about 15 of them on the ipod, and in a random order. I have tried to download in every format (WAV, Apple lossless...) I am allowed to. It will accept some files, and others, not. Same kind of file, format, same download, webpage etc. Does anyone know how to do this? I have switched to manual and reloaded it. When I try to drag a playlist, it tells me that it does not understand the file. (((:[

Welcome to Apple Discussions!
Try playing the songs in iTunes, do they play? Try playing while connected to the internet.
Also, while connected to the internet go to advanced-->deauthorize. Then try playing a purchased song and type in your password and see if they then play on iTunes. If they do then see if they will now sync.
Also, make sure this is updated...
http://www.appe.com/ipod/download
btabz

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