The new Historical Debugger coming in Visual Studio Team System 2010 promises to revolutionize the way you debug managed applications. You can think of it as something of a VCR for your debugger; "rewind" the debugging trace to examine the state of your application at various points in time so you can all-but-eliminate the guesswork about where to place your breakpoints prior to pressing F5.
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This quick overview screencast will give you just a taste of the capabilities offered by the Historical Debugger. For more information check out: