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Jan 9, 2016 7:06 PM in response to iTon17by Kenichi Watanabe,Are you syncing a playlist from your iTunes library to the shuffle, or a set of songs from a playlist?
If you want to play a song list in a certain order on the shuffle, you need to first create that playlist in your iTunes library. After creating the playlist and sorting (or manually ordering) the songs as desired, select the shuffle in iTunes (click device button on horizontal bar) to show the shuffle's settings screen in iTunes window. Along left side of window (in the sidebar), under Settings, click Music. To the right, the shuffle's Music settings screen is shown.
NOTE: Any songs on shuffle that are not in your iTunes music library will be lost.
At the top of window, checkmark the box for Sync Music. Below that, choose the option to sync Selected playlists, artists, albums, and genres. Below that, under Playlists, find and select (checkmark) that playlist with your shuffle songs (you can also select other items on those lists). Then, click Apply. iTunes syncs your selection to the shuffle. Going forward, you can update that playlist (add/remove/re-order songs). The shuffle does not need to be connected. The next time you connect the shuffle (or click Sync if already connected), iTunes updates it with the same changes.
When playing the shuffle, it uses the built-in All Songs list. When the shuffle is set to play in-order, the All Songs list plays songs alphabetically. To play your playlist in your song order, set the shuffle's power switch to the in-order (middle) position, and use VoiceOver to select it from the Playlist Menu. This document explains how to enable and use VoiceOver on the 4th gen shuffle
iPod shuffle (4th generation): Enabling and using VoiceOver - Apple Support