Currently Being ModeratedMay 6, 2013 5:27 PM (in response to BeatriceTuesday)
The latest iTunes may hide the sidebar. If you are a longtime iTunes user, it may be easier using the sidebar. To show the sidebar, from the menu bar, under View, select Show Sidebar. When the sidebar is visible, the On This iPod view goes away; you use the content list under the shuffle in the sidebar instead. If you are new to iTunes, the "new way" may be easier. As a very longtime iTunes user, I like the sidebar way.
The music list on the shuffle cannot be modified directly if you are using automatic syncing. If you set the shuffle to Manually manage music, on the shufflle's Summary screen, you CAN modify the shuffle's music list in iTunes directly. So that may be one solution. But that means you need to create and maintain playlists on the shuffle directly, and add songs by dragging them to the shuffle (or the playlists on the shuffle).
However, you should be able to set the playlist order you want on the iTunes playlist, and automatically sync that playlist to the iPod. When you view the playlist in iTunes (as a plain list), be sure to have the left-most column heading (the one above the column of sequential numbers) selected as the sort order. That is playlist order, and you can drag songs around on the playlist to change the playlist order as desired.
One other aspect of using the 4th gen shuffle is using VoiceOver to select options on the shuffle. When you play songs on the shuffle, you need to select the playlist (from the Playlist Menu) using VoiceOver. Even if there is only one playlist on the shuffle, if you don't specifically select it, you may be playing songs from the default All Songs list, which has its own play order. This document has information about setting up and using VoiceOver on a shuffle.
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