Current discussions of risk and resiliency among adolescents reveal disagreement about definitions of risk and protection from risk. Protective mechanisms have been offered to explain the variability in individual outcomes. However, little is known about the way in which these protective factors combine and interact to promote resilience. Research is needed to explain the stability of protective processes over time, particularly during the stressful transition from childhood to adolescence. This study utilized cross-sectional and longitudinal designs to explore a combination of psychosocial and environmental factors that protect adolescents from academic and behavioral problems during the transition to adolescence. A criterion cutoff method of risk classification resulted in a final distribution of 127 High risk (73%) and 48 Low risk (27%) students at the beginning of 6 th grade. Findings revealed important information about factors that predict more stability versus change in adjustment over time. Changes in academic and behavioral adjustment between 6 th and 7 th grade were predicted by a combination of individual and environmental factors, including factors that act as moderators of risk effects in predicting changes over time. These findings highlight the relative importance of individual variables over environmental factors in predicting the degree of change; however, both individual and environmental factors were related to immediate and longitudinal outcomes. Social skills, self-concept, and locus of control predicted better adjustment at the beginning of 6 th grade. Sixth grade outcomes were also predicted by the interaction between risk and classroom environment, perceived support, and family cohesion. However, the effects of these latter variables appeared to be less important relative to social skills and self-concept. Finally, several mediating relationships were discovered between resource and protective factors. The presence of mediating effects were discussed in light of potential pathways for youth adjustment, where mediator variables were found to more directly influence behavioral and academic adjustment. Findings with protective factors indicate the need for time-sensitive interventions targeting well-defined outcomes among high and low risk youth. Alternatively, findings with resource factors emphasize the need for activities targeting individual characteristics related to positive adjustment for all children during the transition to adolescence.