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From what I understand you are charging with the USB cable. Did you leave it in at least for 3 hours (the PC also has to be on and not in standy or hibernation mode)? Do the glasses charge with the wall charger?
RESETTING OAKLEY THUMP
Most problems can be solved by resetting OAKLEY THUMP:
• To reset OAKLEY THUMP, hold down the Play / Pause button and the Previous Song / Rewind
button at the same time. Resetting OAKLEY THUMP will not erase the songs or files stored
• If the reset procedure does not work, you may need to restore the internal software.
Have you tried to drag individual music files to your Thump? ITumes needs to be set to import in MP3 mode so that the music exports in MP3 mode. My original Thumps will not play AAC format music files. Also, do your Thumps fully charge using the wall charger? Hope this helps.
create a playlist in itunes then put the songs you want to add to your Oakleys in that playlist. Then, burn that playlist to a cd. after you burn it eject it then re-insert it and transfer the songs from the cd to your itunes...i typically just add them as a new playlist called for my Oakley. once you do that you can drag those songs to your oakleys...all you are doing is changing the format from m4p which are basically songs you purchase via itunes that are protected for apple products; ipod, etc., to m4a format...you don't have to go thru all that if you didn't purchase the songs via itunes...hope this helps..