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Originally Posted by connyosis
The player doesn't show up as a removable hard drive in windows? A lot of (If not most) players do that, and you can then just drag the files onto it.
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I'm not sure on this, but I think some versions of Windows 98 do not natively support usb drives, and need a driver.
Have you ever used a usb drive with your machine Tirian? If not, then maybe you could try install drivers for some generic usb drive, and see if that works for your mp3 player.
Might be worth a shot?