How to Manually Update an iPod?

If you choose the manual option, you must manually move songs and playlists onto the iPod. To do this, use the following steps:

1. Connect your iPod to your computer.
2. Select the iPod you want to update. If it isn’t expanded already, click the Expansion triangle next to the iPod on the Source List. In the iTunes Content pane, you will see all the songs in the iPod’s music library. Under the iPod’s icon on the Source List, you will see the playlists it contains
3. To add a playlist to the iPod, drag it onto the Source List and drop it on the iPod icon. When you are over the iPod, the plus sign will appear next to the pointer to show you that you can release the mouse button. When you do so, the playlist and the songs it contains will be moved onto the iPod.
4. To remove a playlist from the iPod, select it by clicking it in the list of playlists under the iPod and pressing the Delete key. You will see a prompt asking you to confirm that you want to delete the playlist.
5. Click OK. The playlist will be deleted from the iPod.
6. To add songs to the iPod, select the source containing those songs, such as the Library. The contents of that source will be shown in the Content pane. Drag the songs you want to add from the Content pane and drop them on the iPod’s icon. The songs you selected will be copied into the iPod’s music library.
7. To remove songs from the iPod, select them in the Content pane and press the Delete key. These songs will be deleted from the iPod. They will also be deleted from any playlists on the iPod containing them.
8. When you are done updating the iPod, unmount it by selecting its icon and clicking the Eject button. After the iPod has been successfully unmounted, it will disappear from the Source List and you will see the “OK to disconnect” message on its screen.

You must eject an iPod that you manually update before disconnecting it because iTunes doesn’t know when it should shut down any processes it is using that are related to the iPod. Because it is, in effect, a hard disk, the iPod must not be in use when you disconnect it; otherwise, its data can be damaged. When the update process is handled by iTunes automatically, it “ejects” the iPod for you. When you do the update manually, you need to tell iTunes that you are done so that it can prepare the iPod to be disconnected safely.