Dynamic Witnesses for Static Type Errors (or, ill-typed programs usually go wrong) by Eric L. Seidel, Ranjit Jhala, Westley Weimer:

Static type errors are a common stumbling block for newcomers to typed functional languages. We present a dynamic approach to explaining type errors by generating counterexample witness inputs that illustrate how an ill-typed program goes wrong. First, given an ill-typed function, we symbolically execute the body to dynamically synthesize witness values that can make the program go wrong. We prove that our procedure synthesizes general witnesses in that if a witness is found, then for all inhabited input types, there exist values that can make the function go wrong. Second, we show how to extend the above procedure to produce a reduction graph that can be used to interactively visualize and debug witness executions. Third, we evaluate our approach on two data sets comprising over 4,500 ill-typed student programs. Our technique is able to generate witnesses for 88% of the programs, and our reduction graph yields small counterexamples for 81% of the witnesses.

Sounds like a great idea to make type systems more accessible, particularly for beginners. The current limitations are described the discussion, section 54:

There are, of course, drawbacks to our approach. Four that stand out are: (1) coverage limits due to random generation, (2) the inability to handle certain instances of infinite types, (3) dealing with an explosion in the size of generated traces, and (4) handling ad-hoc polymorphism.

It's also not clear whether this would produce proper witnesses for violations of higher kinded types or other more sophisticated uses of type systems. There are plenty of examples where invariants are encoded in types, eg. lightweight static capabilities.