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Debugging and diagnostic tools are some of the most important software development tools, but most expect developers choose the right code to inspect. Unfortunately, this rarely occurs. A new tool called the Whyline is described which avoids such speculation by allowing developers to select questions about a program's output. The tool then helps developers work backwards from output to its causes. The prototype, which supports Java programs, was evaluated in an experiment in which participants investigated two real bug reports from an open source project using either the Whyline or a breakpoint debugger. Whyline users were successful about three times as often and about twice as fast compared to the control group, and were extremely positive about the tool's ability to simplify diagnostic tasks in software development work.