The counterinsurgency environments in Iraq and Afghanistan pose special challenges that are difficult, time consuming, and expensive to emulate using conventional training approaches. Deployed American Soldiers, operating amid civilian populations, continuously encounter unfamiliar complex dilemmas that demand decisionmaking in the wake of ambiguity. The requirement for decision-making is not reserved for senior leaders with deep experience. Rather, it extends to even the newest Private and Second Lieutenant. This paper describes the development of an immersive training framework for the US Army Center for Army Leadership that subjects the learner to complex critical decision-oriented scenarios patterned after incidents gathered from the field. Scenarios are designed to pose ‘leadership dilemmas’ for the learner which generate immediate and long-term outcomes based on those decisions. Over time successive decisions generate variability in the simulation, which pose new challenges to the learner, namely the need to understand that decisions have implications beyond the immediate impact. This approach is designed to purposefully engage the learner in additional ‘what-if’ scenarios, while promoting personal reflection and dialogue with others towards alternate strategies within the decision-making process.