Open the iTunes software and connect your iPod to the computer. Make sure you connect the USB cable securely to the iPod and the computer. Allow the iPod to sync to the computer; do not disconnect the iPod during this phase. The iPod will display a warning not to remove the iPod when it is syncing. If you remove while syncing you may lose files on the iPod.
Click on the iPod icon to the left of the iTunes menu just under the title "Devices." Click on the top tab and select "Music." On the "Music" page select the radio button next to "Sync Entire Music Library." You will see a "Capacity Meter" showing if your iPod has enough space for the entire library. If the bar is showing maximum capacity, you will have to delete unwanted songs in your library if you want to fit all your favorites onto the iPod. Once you select these options, your iPod will automatically sync when connected.
There are many cases where an iPod won't sync the entire library from iTunes. Some common reasons include the files not being supported by the iPod, not having enough space on the iPod and running an old iTunes version. However, in some cases where files are incompatible, you won't be able to get them on the iPod; but you can still troubleshoot the iPod for other reasons when the library isn't syncing correctly.
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