The Joint Force of today is facing an inflection point with respect to the way it believes it should learn, train, and educate. The generation that fought America’s longest war is more savvy and intuitive but also sober on what really “works.� The authors have observed, for instance, that “Jointness� is being redefined, and correspondingly preparation for it is shifting, focusing less on systems and more on developing higher-order cognitive skills, such as problem-solving, adaptiveness, and anticipation. However, trainers are unclear on how to create interventions that simultaneously un-lock the cognitive potential of their staffs, enable accurate and actionable performance measurement, and support affordable scalability to geographically dispersed training audiences. We argue that part of the solution requires exploiting web-based technologies that can create semi-immersive experiences in “strategic compression,� which we use as a short-hand reference for the stresses of operational/strategic crisis action planning and decision-making under time constraints, contextual complexity, and organizational ambiguity. If those conditions are rendered in a distributed team simulation (part-task trainer) and paired with appropriate instructional interventions, this creates opportunities for trainers to facilitate quality interventions in support of a group’s decision-making processes (i.e., “strategic reflection�). The authors build upon previously published research related to technology-enabled joint training at the lower-end of the cognitive learning taxonomy (i.e., remember, understand, and apply; see Fautua, Schatz, et. al., I/ITSEC 2014) to provide preliminary findings in establishing similar interventions for the taxonomy’s upper end: analyze, evaluate, and create.