It also depends on where it's purchased from. If it's DRM protected media (like itunes) it won't play on the BB. There are programs out there that will remove the DRM from your files, then you'll be all set.
Roxio will not transfer DRM protected music. While other apps can be used to transfer DRM protected music to a media card, the BB will still not play it. Someone mentioned Double Twist in another thread as possibly allowing a BB to play DRM protected music, although I haven't tried it.
BTW I believe I used Windows Media Player with my BB set to mass storage to transfer DRM protected songs to the media card, but as I said BB simply won't play them. Another good suggestion was to avoid buying DRM protected songe in the future.
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