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Isn't the first thing to do looking at what the compiler can tell you (-fopt-info for GCC)? That can be helpful without deep knowledge of the target, or knowing its assembler. There are also dumps from stages before generating assembly which may be helpful. Is it deep knowledge of the whole system that makes going straight to assembly best?

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Yes, GCC intermediates are quite nice. Lispy and readable. And indeed, you can take a look at every stage. But LLVM intermediate code is basically just another assembly language. And as for MSVC, I'm not sure if it's even accessible. So it's not always an option.

Disassembly is either way our end result so unless you're looking for something particular, it makes sense to browse that first just to check that the compiler gets your intention just right.

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