hi newberry-well heres wat i do-i dont know of a simpler way open dm>usb ur bb>get the media open & shrink (not minimiz) the screen where you can still see where ur bb media card is. >then open itunes>shrink screen but not too much, you still have to see the songs & the dm media card at the same time. from the itune, highlight>click&drag>onto your bb media card. wen ur done, ck ur bb to verify everything you drop'd in is there and your good to go! ive done this with itunes that were purch'd also & it workd. good luck hope this helped!