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Case in Point (CIP) is an interactive leadership development method pioneered by Ronald Heifetz. CIP instructors follow a fluid class structure, in which group dynamics and student concerns become catalysts for learning. CIP proponents defend the method’s potential to help students experience real life leadership challenges. To date, however, very limited research exists on the effectiveness and risks of the CIP. This case study research explored the risks and rewards of CIP as experienced by a professor and her students in two courses. The first case was a graduate course at a liberal arts college. The second case was an undergraduate course at a large public institution. Results revealed considerable variability in student experiences. Students in the graduate course were divided. While some strongly supported the instructor and the CIP method, others felt alienated and lost. Students in the undergraduate course clearly enjoyed the experience, dealing well with uncertainties and frustrations and forging strong bonds among each other and with the professor. CIP instructors, therefore, may need to manage an uneven environment. Risks include student frustration, increased conflict, and instructor exhaustion. Rewards include helping students experience leadership challenges and creating a close to real life environment. Instructors are urged to consider the ethical implications of CIP and to seek university and peer support.