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Hard to tell. Debugging by guessing might work if you already have an idea about what the bug is (incorrect value passed to a library function, possibly invalid SQL, etc). I admit I do it sometimes when the error itself seems small or obvious, such as "character buffer too small" - the stack trace shows me the line it failed and I don't need a debugger to solve that one.

Doing this all the time can be counterproductive and if the first few "guesses" fail, guessing is probably the wrong problem-solving strategy and a real debugger should be called in. Normally, I'd say there's absolutely nothing wrong with using the debugger.

That being said, I've worked with tools and environments where the debugger was so difficult to get working right, or so minimal and useless that guessing was unfortunately often a better approach. I've worked with some proprietary tools that didn't even have proper debuggers. I suppose it's possible that if a person worked in such environments too long they'd eventually lose their trust in debuggers and rely soley on the guessing approach.