Just make sure you have the latest version of itunes and ipod software installed. It should solve the problem. If not, you can restore your ipod to reset it to factory settings (WARNING: restoring your ipod will totally erase the data on it.) Good Luck.
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You just need to import your songs into iTunes library, then make a playlist with the songs, connect your iPod to computer, iTunes will detect the iPod automatically, then click iTunes menu "File -> Sync iPod", the songs will be transferred from iTunes to iPod. Or You may try this ipod transfer, it's
a nice iTunes alternative that can help you manage iPod files including delete,
upload, play, copy, etc. It's much easier to use than iTunes.
When it comes to transferring music from computer to iPod, iTunes is always the first choice for most of iPod users. As the official transfer tool, iTunes can help you to transfer music to iPod easily. The next guidance will show you how to transfer music from computer to iPod with iTunes.
Connect your iPod to PC via matched USB cable. Then click the iPod icon on the left corner of the interface. To manage your media files manually, you'd better go to "Options" under "Summary" tab, cancel "Automatically sync when this iPod is connected" and check "Manually manage music and videos". Don't forget to click "Apply" when it's done.
Import music into iTunes library from computer by clicking "File" and then "Add File to Library". Once transferred successfully, you can select the music icon on top to see all the songs.
Click "Music" under "Settings" tab. Choose "Sync Music". You can either sync entire music library or selected playlists as you like. Then click "Sync" button at the bottom to transfer music from computer to iPod.
You probably do not want to use iTunes for syncing your iPod music when you have got a lot of CD music long time ago, because iTunes can't sync them back to computer. "How can I transfer music to iPod without iTunes?" You may want to ask this question. Well, a powerful iPod transfer software is helpful on the iPod music syncing issue. http://www.leawo.org/tutorial/how-to-transfer-music-to-ipod-without-itunes.html