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May 11, 2016 9:54 AM in response to JoyceWby Kenichi Watanabe,If this is a 3rd or 4th gen shuffle, check the setting for Manually manage music. Select shuffle in iTunes (click its device button on horizontal bar) to show its Summary settings screen in iTunes window. To the right, is the setting for Manually manage music currently checked or not checked? If it's checked, the shuffle is set to load songs manually, so clicking Sync button does "sync" the shuffle, but no songs will sync. If you want it to use automatic syncing for music...
In the sidebar, under Settings, click Music. To the right, the iPod's Music settings screen is shown. Checkmark the box for Sync Music. This turns ON automatic syncing.
NOTE: Any songs on the shuffle that are not on your iTunes library with be lost.
Below that, if your iTunes music library is really small and fits on the shuffle, you can choose the option to sync Entire music library. Otherwise, choose the option to sync Selected playlists, artists, albums, and genres. Then make your selections from the lists below. For example, you can create and maintain (one or more) playlists in your iTunes library, with songs you want on the shuffle. On the iPod's Music settings screen, under Playlists, select those playlists. Click Apply to sync your music library, or selected portion of it, to the shuffle. Going forward, iTunes automatically keeps your shuffle "in sync" with your iTunes library, or selected portion of it, when you connect it (or click the Sync button if already connected).
OR, you can leave it set to Manually manage music, and use the Autofill feature. With my shuffle, I use Autofill to load a random selection of songs from a "favorites" playlist (that is much larger than the shuffle's capacity), every time I connect it to charge. Autofill is not automatic syncing. For more details on the Autofill feature, please post back.