Contextually based assessments reveal the circumstances accompanying maladjustment (the when, where, and with whom) and supply clues to the motivations underpinning problem behaviors. The Adjustment Scales for Children and Adolescents (ASCA) is a teacher rating scale composed of indicators describing behavior in 24 classroom situational contexts. This study examines the Trinidad and Tobago national normative process for the ASCA contextual dimensions with a representative sample of elementary school children (N = 900). Exploratory and confirmatory factor analyses yielded the same three dimensions (peer context problems, teacher context problems, and learning context problems) observed in U.S. national samples. Dimensions were scaled using item response theory (IRT) and Bayesian scoring methods, with peer and learning context problems scores relating more strongly to clinical behavior disturbances and learning context problems showing stronger association with classroom learning styles. Implications for future research and practice are discussed.