Reffering to what rhullopeter said, your phone wont play the itunes format songs like theones you bought off itunes so an easy solution to those songs of those format is to burn them on a disc through itunes then import them using realplayer or windows media player
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i am currently dealing with the same problem with my BJ III aka Samsung Jack. I had the BJ II before upgrading and had the same problems, but assumed that Samsung would have fixed this problem with the new phone. Apparantly NOT! Or it's just a stupid windows bug. idk, either way, it sucks! because i have deleted MOST of my messages, all of my "sent" and "deleted" folders in messaging, i've moved all pictures, sounds, media etc to my storage card, and yet STILL only have 10MB of storage available. oh, aaaand i ONLY have google maps installed as an add-on application. really? really samsung?!??!
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I found a little problem with this too. So I created a folder to put on my storage card. Name it whatever you want. Now take these steps to get to it to play all the songs in the folder:
When you are in Windows media player, click menu, open file, storage card, The name of your folder. You should be setup to play all those songs as a playlist now.
Hope this helps, I haven't messed with it anymore so I've stuck to it doing this. Good luck.