Player freezes during transfer

Just got my miniplayer in the mail today and I'm trying to put some music on it. I'm using Mac OS X Leopard.

When I drag files into the MUSIC folder, they begin to transfer but it always freezes less than halfway through. I can't eject the miniplayer or stop the transfer. The only thing to do is unplug it, which damages data and makes my computer angry with me.

What's going on? Am I transferring too much data at once? My next step is to transfer one artist at a time and see if anything improves.

Have you tried dragging fewer files at a time? I have never tried to transfer more than 10 albums worth of data at once, and have never had issues, aside from taking half an hour to transfer.