Combat Search and Rescue aircrew are tasked with challenging missions, usually under conditions of time pressure, dynamic conditions, and a high degree of uncertainty. Many skills required for successful outcomes (e.g., solving problems quickly; accurately evaluating risks; adapting to rapidly changing environmental conditions) are acquired and maintained through first-hand experiences. This paper describes a research project to develop a pedagogically effective game-based trainer for cognitive skills required for Combat Rescue Helicopter aircrew. Training scenarios are developed using cognitive interviewing techniques in order to promote cognitive authenticity. The trainer will pose critical decisions and provide expert feedback utilizing ShadowBox®, a proven coaching technique that enables trainees to obtain insight into the decisionmaking processes and reasoning of experts.