Rather than verifying all possible compiler outputs, just check that the current output was optimised correctly!
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I would have thought that invoking a C compiler would be a solved problem. Looking at Rust's cc crate there's a remarkable long tail of corner cases to fix.
Exotic CPUs, microarchitectures, compiler differences, operating system differences, etc.
https://github.com/rust-lang/cc-rs/blob/main/CHANGELOG.md
Some delightful examples of good compiler error messages in the latest Gleam release: https://gleam.run/news/context-aware-compilation/
I'm working on arity errors in Garden, my toy programming language.
Rather than just saying "expected 3, got 4 arguments", I'm trying to report where the extra argument is, or what extra argument was expected.