The second-generation iPod shuffle has a storage capacity of either 1GB or 2GB and only supports audio content. While other iPods use a sync cable to connect your iPod to the computer, the second-generation iPod shuffle connects to a dock that connects to the computer for syncing media. iTunes gives you the choice of manually selecting what songs are loaded to your iPod shuffle, or using the Autofill feature to load the next songs in the iTunes line-up or randomly load songs.
Connect your iPod shuffle to the computer using the USB cable that came with the device and then open iTunes.
Select "Music" on the left side of the program window under "Library." To select multiple songs hold down "Ctrl" and then click each song.
Drag the highlighted songs from the right pane to your iPod shuffle icon under "Devices" on the left pane to add the songs to your device. Hold the songs over your iPod shuffle icon until the iPod shuffle icon is highlighted. The songs will begin syncing to the iPod. A progress bar will be displayed at the top of the iTunes program window displaying the overall status of the sync. When the sync is complete, a message will be displayed in place of the progress bar notifying you that the sync is complete.
Click the "Eject" icon to the right of the iPod shuffle icon to eject your iPod.
Disconnect the dock's USB cable when its status light does not flash anymore and remove your iPod shuffle from the device's dock.
Use your iPod shuffle's USB cable to connect the device to your computer and then launch iTunes.
Click your iPod's icon under "Devices" on the left side of the program window and then select the "Contents" tab on the right side of the program window. Click "Settings" in the bottom of the window to access Autofill preferences. Select "Replace All Items When Autofilling" if you want to replace all of the songs on your iPod shuffle with new songs. Select "Choose Items Randomly" if you want to add a random mix of songs to your iPod. Use the slider under "Reserve Space for Disk Use" if you want to reserve space on your iPod for portable disk use. Click "OK" to apply the new settings.
Select the type of content that you want to sync from the "Autofill From" drop-down menu in the bottom of the window and then click "Autofill" to load the songs onto your iPod shuffle.
Click the "Eject" icon to the right of the iPod shuffle beneath "Devices" and then disconnect the USB cable from the computer when the process is complete.