Device : iPod Shuffle 2nd Second Generation
OS : Windows 7 64 bit
My steps were as follows
I checked the "Sync only checked songs"
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
Contents tab
Best Answer
There is an Autofill button that you must select (click) before syncing to get the music onto the device.