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Helpful answers
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May 9, 2013 9:27 AM in response to beau1975by BobbyDigital00,I would make sure you're not in a single playlist, that may be why you're hearing a certain selection of songs. Try rebooting the shuffle and trying again: Here is how to do that.
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May 9, 2013 12:42 PM in response to beau1975by Kenichi Watanabe,Which shuffle model is it? This document shows the four types
http://support.apple.com/kb/HT1719
For any model, make sure you have it set to shuffle and not play-in-order. On the 2nd gen shuffle, there is a separate switch for play mode. On the other shuffle models, the power switch has a middle position, which is play-in-order. Make sure it's set to shuffle, because play-in-order always starts at the top of the list of songs.
If it's a 3rd or 4th gen shuffle, it can play from multiple playlists; use the VoiceOver feature and select the All Songs list from the playlist menu. This is a document for the 4th gen shuffle about setting up and using VoiceOver; the 3rd gen shuffle should be similar.
http://support.apple.com/kb/ht4322
1st and 2nd gen shuffle does not have VoiceOver, and only has one list that it plays from.