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WinAmp has shuffle features that prevent this problem. There are options
to "Do not repeat the same artist in a row" and "Do not repeat the same
song title in a row". There are other options that really make the
Shuffle feature great to use. It's unf...
I have exactly this same problem and also in my case it plays the
playlist and then gets to a track and starts repeating that track over
and over without shuffling to the next track.