Try plugging your player into your computer, then from your desktop go to Start>My Computer. You should see your player listed there as one of the drives. Double click on it to open it.

Now open the folder with your files in it, by default it's C:\documents and Settings\"your account name"\Shared. Drag n drop the files you want from your shared folder to your mp3 player and they should be added automatically.

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If it ain't broke, fix it till it is!