Reachability and error diagnosis in LR(1) parsers https://gallium.inria.fr/~fpottier/publis/fpottier-reachability-cc2016.pdf —interesting discussion of syntax error messages, used in compcert
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Really cute approach to reporting type errors: when there's a type error, show an example of a runtime error that the type check has prevented!
Data-Driven Techniques for Type Error Diagnosis https://escholarship.org/uc/item/59s4h4pv
Symptoms, diagnosis, and the recommended treatments of bad code from modern compilers: