Technology-enhanced simulation has been used to tackle myriad challenges within health professions education. Recently, work has typically adopted a mastery learning orientation that emphasizes trainees’ sequential mastery of increasingly complex material. Doing so has privileged a focus on performance and task completion, as captured by trainees’ observable behaviors and actions. Designing simulation in these ways has provided important advances to education, clinical care, and patient safety, yet also placed constraints around how simulation-based activities were enacted and learning outcomes were measured. In tracing the contemporary manifestations of simulation in health professions education, this article highlights several unintended consequences of this performance orientation and draws from principles of adaptive expertise to suggest new directions. Instructional approaches grounded in adaptive expertise in other contexts suggest that uncertainty, struggle, invention, and even failure help learners to develop deeper conceptual understanding and learn innovative approaches to novel problems. Adaptive expertise provides a new lens for simulation designers to think intentionally around how idiosyncrasy, individuality, and inventiveness could be enacted as central design principles, providing learners with opportunities to practice and receive feedback around the kinds of complex problems they are likely to encounter in practice. Fostering the growth of adaptive expertise through simulation will require a fundamental reimagining of the design of simulation scenarios, embracing the power of uncertainty and ill-defined problem spaces, and focusing on the structure and pedagogical stance of debriefing. Such an approach may reveal untapped potential within health care simulation.