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Welcome to the club! I gave up on debugger a long time ago. WRI has developed a (supposedly) good functionality, but they did not bother to document it well. Why should we, the users, waste time trying to figure out how it works? You will find some explanations (by WRI people) on this group about Debug, but not much. I suggest you use ON and Off and sprinkle the code you are testing with Print commands to see the value of variables. This way you clearly see the behind-the-scenes actions of your code. Trace gives you the same information, but the output is not so well formatted and is difficult to read. Workbench is supposed to be the Integrated development environment (IDE) for Mathematica, but well-known mathgroupers have told me that - at the moment - it is more an headhache, rather than an Aspirin.