Just for the heck of it, try changing the setting to shuffle or repeat or whatever and see what it does.
Or…
Do you know if you have a v1 (Under Settings/Info/Firmware Version begins with 1.x) or v2 (begins with 3.x).
You can try deleting the index. In a v1 it is the DATA folder inside SYSTEM (you need to un-Hide hidden folders in Windows). In a v2 it is mtable.sys. The Sansa will reconstruct the index when you disconnect.
