I had this problem appear when I upgraded to Winamp 2.80 using the Crossfading DirectX output plugin that comes with the Winamp install. It would just stop for no reason. Using an older version of Winamp (2.72 I think) works fine, and if I use the Waveout output instead if DX, it's fine.
It's a shame, because the crossfading works really well otherwise - i only have problems on the car player - on any of my other computers it plays fine.



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