The United States military's strategic position is evolving, and as a result, the Services are emphasizing the importance of sociocultural pattern recognition, sensemaking in ambiguous urban contexts, and understanding of patterns of life. In fact, military personnel at increasingly lower echelons are expected to possess these nuanced psychosocial perception and decision-making skills. To facilitate training of these complex competencies, the authors are developing a Virtual Observation Platform, an immersive virtual environment designed to adaptively train US Marine Corps personnel in sustained observation, sociocultural pattern recognition, anomaly detection, and other perceptual-cognitive skills. This paper briefly describes the purpose of the system and then covers its adaptive instructional tailoring in detail. The Platform's adaptive features include information quality/quantity manipulation and instructional scaffolding in the form of communications from a virtual squad (i.e., peers) that are intrinsic to the narrative of the scenario.