iTunes 9 Issue: Smart Playlists not syncing to iPhone, iPod

Some users may experience an issue where their Smart Playlists are not syncing to their iPhone or iPod as expected. The lists appear in a different order or with different content. The first step in troubleshooting your iPhone or iPod and iTunes is to be sure all your software is up-to-date. Open iTunes and from the iTunes menu bar select iTunes > Check for Updates... Next, plug in your device. iTunes will alert you if you need to update your software for it.

If the issue is that your Smart Playlist is not in the same order as it appears in iTunes, follow these steps to resolve the issue:

1. Select the Smart Playlist with the issue and arrange it as you would like it to appear on your device.
2. Right-click (Control + Click) the Smart Playlist name and choose "Copy to Play Order" from the contextual menu.
   (Credit: Screenshot by Apple)

3. Sync your iPhone or iPod with iTunes and check the playlist on the device.

If the issue is that your Smart Playlist does not contain the same content that it does in iTunes, follow these steps to resolve the issue:

1. Right-click (Control + Click) the Smart Playlist with the issue and select Edit Smart Playlist from the contextual menu.
2. Click the (+) button to create a new rule for your playlist.
3. Choose "Media Kind", "is", "Music" (or the type of media that the list contains--podcast, music video, etc.)
   (Credit: Screenshot by Joe Aimonetti)

4. Click OK and sync your iPhone or iPod with iTunes.

If the previous set of steps fail to resolve your issue, follow these steps:

1. Right-click (Control + Click) the Smart Playlist with the issue and select Edit Smart Playlist from the contextual menu.
2. Deselect the option for "Live Updating", click OK, and sync your iPhone or iPod with iTunes.

If the issue persists, follow these workaround steps:

1. Click the Smart Playlist that has the issue and from the iTunes menu bar select Edit > Select All.
2. From the iTunes menu bar select File > New Playlist from Selection. Enter a name for your playlist.
3. Sync the new playlist with your iPhone or iPod.

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