I don't have the shuffle, have the Nano, but the program should be the same.
When Itunes is open on your PC and you are in your music library check to be sure that there is a 'check' mark next to all songs that you would like loaded. When you plug the shuffle in to load it the screen that comes up has option on the bottom that you can place 'check' marks by. One is to 'sync' all items that are checked. I am purely guessing here, but that may be the problem.?? It will tell you when it is done loading and when it is OK to disconnect. I have accidentally disconnected before it is done syncing and it caused to not to download anything.
Gosh I hope it works!!!
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