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Gamification involves the application of game design elements to traditionally nongame contexts. It is increasingly being used as an adjunct to traditional teaching strategies in medical education to engage the millennial learner and enhance adult learning. The extant literature has focused on determining whether the implementation of gamification results in better learning outcomes, leading to a dearth of research examining its theoretical underpinnings within the medical education context. The authors define gamification, explore how gamification works within the medical education context using self-determination theory as an explanatory mechanism for enhanced engagement and motivation, and discuss common roadblocks and challenges to implementing gamification.Although previous gamification research has largely focused on determining whether implementation of gamification in medical education leads to better learning outcomes, the authors recommend that future research should explore how and under what conditions gamification is likely to be effective. Selective, purposeful gamification that aligns with learning goals has the potential to increase learner motivation and engagement and, ultimately, learning. In line with self-determination theory, game design elements can be used to enhance learners’ feelings of relatedness, autonomy, and competence to foster learners’ intrinsic motivation. Poorly applied game design elements, however, may undermine these basic psychological needs by the overjustification effect or through negative effects of competition. Educators must, therefore, clearly understand the benefits and pitfalls of gamification in curricular design, take a thoughtful approach when integrating game design elements, and consider the types of learners and overarching learning objectives.