In this research project, a novel app-based version of the code breaking game Mastermind, Entropy Mastermind, wasintroduced and evaluated as a learning medium in undergraduate cognitive psychology and in primary mathematics ed-ucation. In a quasi-experimental pre- and posttest design we investigated a) the role of individual differences in gameplay and learning, b) the effectiveness of Entropy Mastermind for giving students of different age groups experientiallygrounded access to the fundamental concepts of proportions and mathematical entropy, and c) effects of game play onstudents academic emotions, motivation and attitudes. Data analyses revealed significant associations between cognitivevariables, emotional-motivational factors and game play parameters. We present computational modeling results of stu-dents search strategies and entropy intuitions within a unified framework of entropy measures, the Sharma-Mittal space.Potential applications in digitalized learning environments at the interface between mathematics and computer science willbe discussed.