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I think my record when I was on the WinDbg team was 5 debuggers deep.

I honestly think one of the best parts of writing a debugger is being your own recursive customer. I think that's something you only get to do for a few things. Debuggers, languages/compilers, and operating systems. And probably a few others.

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Not 5 levels, but I once wrote debug visualizers for a compiler using funceval (the visualizer uses the debugger to run code in the target process).

I think I once had to debug the debugger debugging the compiler compiling itself which felt like another really weird kind of recursion.

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