Automatically adding and removing songs and playlists

When iPod is set to automatically synchronize all music with iTunes (default setting), songs and playlists that are added or erased from your iTunes Library will also be appended or deleted from your iPod when the iPod is connected and synchronized with iTunes. If your iPod is set to only synchronize certain playlists automatically, songs are added or removed from the iPod when they're added or removed from the playlists in iTunes that are synced to iPod ( if your iTunes Library contains more than 100 playlists, some playlists will not be showed when setting your iPod to sync only certain playlists ).

Manually adding and removing songs of playlist

If you want to manage the songs and playlists on your iPod individually from the way you manage them in iTunes, start by setting iTunes to Manually manage the content on your iPod.

Next, Click the gray triangle icon next to your iPod in the iTunes Source pane. This will allow you to see the contents of your iPod. You can add playlists and songs store in iTunes to your iPod simply dragging them to the iPod in the Source pane.

you are able to remove items from the iPod by highlighting them as they come along on the iPod and choose Delete from the Edit menu.

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