This study explored the experiences of middle school students, particularly focusing on the academic achievement of economically disadvantaged students. For low SES middle school students, the known cumulative effects of poverty coupled with school transition and early adolescence development heighten the potential risks for school failure. By utilizing the nationally representative Early Childhood Longitudinal Study-Kindergarten (ECLS-K) 1998/99 longitudinal data, this study explored parent involvement and school belonging as potential protective factors. The findings for this study showed that when parent involvement and school belonging were considered together, parent involvement emerged not to be significant while school belonging consistently emerged as a significant predictor of achievement. However, while school belonging emerged as a significant predictor, prior achievement was the single strongly significant factor explaining achievement.