1. Verify that VoiceOver has been enabled. If VoiceOver is disabled, you will hear the default playlist names like "playlist 1" or "audiobook 1."
2. You may be low on memory. You might have too much content such as songs and podcasts synced so it does not have enough room to save the VoiceOver files. Free up space on the iPod shuffle by removing some songs or podcasts and then reinstall the VoiceOver files using the steps below.
3. The iPod shuffle (3rd generation) may be disconnected from the computer before the VoiceOver files are generated and synced over to the iPod. This can occur if iTunes is enabled to "Manually manage music" for the iPod shuffle. Reinstall the VoiceOver files to the iPod shuffle and leave it connected to the computer until you see the "iPod sync is complete. OK to disconnect" message in iTunes.
To reinstall the VoiceOver files on iPod shuffle (3rd generation)
1. In iTunes, select iPod shuffle in the list of devices, and click the Summary tab.
2. Under Voice Feedback, deselect Enable VoiceOver.
3. Click Apply
4. Select Enable VoiceOver.
5. Click Apply.
[Source: Apple Technical Articles]
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