Have iTunes Automatically Fill Your iPod
If you haven't already set your iPod to automatically sync with your iTunes library in the iPod Setup Assistant, follow the steps below to have iTunes fill your entire iPod with your music, podcasts, and audiobooks whenever you connect it. If you did set iTunes to automatically update songs and playlists, just connect your iPod to your computer to start filling it up!
Fill Up Any iPod with a Display
1. Connect your iPod to your computer. iTunes should open by default (if you set iTunes preferences to not open iTunes when you connect your iPod, open iTunes manually).
2. Open iTunes preferences. Mac users: From the iTunes menu, choose Preferences. Windows users: On the Edit menu, click Preferences.
3. Click the iPod tab to display its preferences, then click the Music tab in that pane.
4. If you want your iTunes library and your iPod to mirror the same content, select the "Automatically update all songs and playlists" radio button. (This will replace all existing iPod content with your current iTunes library and playlist content, so don't select this option if you want to preserve what you've got on your player.) If you'd rather have iTunes sync only songs in certain playlists, select the "Automatically update selected playlists only" radio button, then select the checkbox next to each playlist you want to sync.
5. If you have podcasts that you'd like to sync too, click the Podcasts tab in the iPod pane (not the main Podcasts tab).
6. To sync all podcasts, select the "Automatically update all Podcasts" radio button. If you want to pick podcasts to sync, select the "Automatically update selected Podcasts only" radio button, then select the checkbox next to each podcast you want.
7. When finished, click OK and iTunes will start filling up your iPod with your selected audio files. Please be aware that this can take a while, depending on how large your iTunes library is.
8. When you're ready to start playing with your iPod, disconnect it from your computer by clicking the small eject button to the right of your iPod icon in the Source list. When the icon disappears from iTunes and your iPod says that it's OK to be disconnected, you can safely disconnect your iPod.
Fill Up iPod shuffle
1. Connect iPod shuffle to your computer. iTunes should open by default (if you set iTunes preferences to not open iTunes when you connect your iPod shuffle, open iTunes manually).
2. Select your iPod shuffle in the Source list.
3. In the pane below the song list pane, you'll see several options that allow you to control what songs to automatically transfer to your iPod shuffle. From the Autofill from pop-up menu (drop-down in Windows), choose Library if you want to copy random songs from your entire library, or choose a playlist from which to copy tunes.
4. If you already have some songs on your iPod shuffle but want to replace them, select the "Replace all songs when Autofilling" checkbox. Otherwise, deselect this checkbox to keep your current songs intactâ€'iTunes will then add songs to your existing collection.
5. If you select the "Choose songs randomly" checkbox, iTunes will select songs at random from your chosen source. If you deselect this checkbox, iTunes will fill your iPod shuffle with songs from your chosen source in the order in which they appear until either your iPod shuffle is full or all songs are copied.
6. If you want iTunes to lean towards copying your higher rated songs, select the "Choose higher rated songs more often" checkbox. If you're not a faithful song rater, don't select this checkbox.
7. Click Autofill to make iTunes start filling your iPod shuffle with songs. Please be aware that this can take a while, depending on how large your iTunes library or playlist is. If you want to add podcasts or audiobooks, follow the next two steps.
8. To add particular podcasts to iPod shuffle, select Podcasts in the Source list. Then either select and drag a podcast title to the iPod shuffle icon in the Source list to copy all of the downloaded episodes, or click the disclosure triangle next to any podcast title and drag any podcast listing to the iPod shuffle icon to add individual episodes.
9. To add particular audiobooks to iPod shuffle, select Library in the Source list, select an audiobook in the song list pane, and drag it to the iPod shuffle icon in the Source list.
10. When you're ready to start playing with iPod shuffle, disconnect it from your computer by clicking the small eject button to the right of the iPod shuffle icon in the Source list. When the icon disappears from iTunes, you can safely unplug iPod shuffle.
Manually Add Songs, Playlists, Podcasts, and Audiobooks to Your iPod
If you have an iPod with a display and want manual control of your music (this doesn't apply to iPod shuffle users), first make sure that iTunes isn't set to automatically update songs whenever you connect your iPod. (You originally set this option when you first installed your iPod software.) If you need to change this status, do this first:
1. Open iTunes preferences. Mac users: From the iTunes menu, choose Preferences. Windows users: On the Edit menu, click Preferences.
2. In the resulting dialog, click the iPod tab, then click the Music tab in the iPod pane.
3. Select the "Manually manage songs and playlists" radio button.
4. Click the Podcasts tab in the iPod pane (not the main Podcasts tab).
5. Select the "Do not update Podcasts" radio button if you want to manually do the deed.
6. Click OK.
To add songs, playlists, podcasts, and audiobooks to any iPod model, just follow these instructions:
1. Connect your iPod to your computer. If iTunes doesn't automatically open after you connect it, open iTunes.
2. To add songs or audiobooks from your library, select Library in the Source list, select one or more items you want (to select multiple songs and audiobooks, Command-click items on a Mac or Control-click items in Windows), then drag them onto your iPod icon in the Source list.
3. To add a playlist (which will also copy the songs it contains if they're not already on your iPod), select the playlist in the Source list and drag it onto your iPod icon in the Source list.
4. To add podcasts, select Podcasts in the Source list. Then either select and drag a podcast title to your iPod icon in the Source list to copy all of the downloaded episodes, or click the disclosure triangle next to any podcast title and drag any podcast listing to add individual episodes.
5. When you're ready to start playing with your iPod, disconnect it from your computer by clicking the small eject button to the right of your iPod icon in the Source list. When the icon disappears from iTunes, you can safely disconnect your iPod.
Source: apple.com