Software acting on complex data structures can be challenging to test: it is difficult to generate diverse test data that satisfies structural constraints while simultaneously exhibiting properties, such as a particular size, that the test engineer believes will be effective in detecting faults. In our previous work we introduced GödelTest, a framework for generating such data structures using non-deterministic programs, and combined it with Differential Evolution to optimize the generation process. Monte-Carlo Tree Search (MCTS) is a search technique that has shown great success in playing games that can be represented as sequence of decisions. In this paper we apply Nested Monte-Carlo Search, a single-player variant of MC...