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Device : iPod Shuffle 2nd Second Generation OS : Windows 7 64 bit

My steps were as follows

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I checked the "Sync only checked songs"

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Even though i checked some songs before syncing, i did not find any of them in my iPod. The sync completed without any error output.

Settings tab

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Contents tab

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2 Answers 2

There is an Autofill button that you must select (click) before syncing to get the music onto the device.

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Get info for the checked tracks and see if in the Options tab, Skip when Shuffling is checked. If so, those tracks won't sync to an iPod shuffle.

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