The present study examined how the relationship between child temperament and behavior is expressed in different types of classroom environments in prekindergarten settings. Other goals of the study were to further operationalize the goodness of fit model in school settings and to evaluate possible interactions of process variables indicative of classroom quality with child temperament to see if these interactions predicted child behavior and social skills. Participants included 130 students and their teachers (N = 11) in three prekindergarten settings. Child temperament was measured using the Total Temperament score from the Teacher and Caregiver Temperament Inventory for Children (TACTIC; Billman & McDevitt, 1998). Classroom quality and environment characteristics were measured using the Program Structure scale of the Early Childhood Environment Rating Scales-Revised (ECERS-R; Harms et al., 2005) and the Sensitivity subscale score from the Caregiver Interaction Scale (CIS; Arnett, 1989). Outcomes in behavioral and social domains were measured using the Externalizing Behavior Problems and Social Skills subscales on the Preschool and Kindergarten Behavior Scales-Second Edition (PKBS-2; Merrell, 2002). Hierarchical linear modeling indicated that child temperament alone was the sole predictor of child externalizing behavior, while child temperament, disability status, and school program structure predicted child social skills. Overall, the study indicated that the goodness of fit model when operationalized in terms of the transactional relationship between temperament and environmental demand factors of characteristics of the classroom setting (as informed by the classroom quality literature) has predictive value and describes child behavioral and social outcomes in prekindergarten settings.