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the dialog won't show as there's a bug with the plug-in in how it works and that bug results in no settings dialog appearing and / or Winamp crashing when trying to access it.
it might be possible to directly edit the password in the registry though i don't have any of the details to hand to attempt to work that out.
otherwise you've either got to wait for an updated version of the plug-in to be released or use an alternative way of getting your played history from the ipod without using the plug-in.
-daz
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