Traditional mental health models focus on psychological problems and distress; accordingly, health is viewed as the absence of illness or disability. In contrast, a dual-factor model of mental health incorporates both indicators of positive subjective well-being (SWB) and measures of psychopathological symptoms to comprehensively determine an individual’s psychological adjustment. This study used such a dual-factor model to measure the mental health status of young adolescents. A total of 764 middle school students were classified into one of four distinct groups based on having high or low psychopathology and high or low SWB. Furthermore, group differences in student engagement, academic achievement, and environmental support for learning were investigated. Results demonstrated the existence of a traditionally neglected group of adolescents (low SWB and low psychopathology) who are nonetheless at risk for academic and behavior problems in school and who performed no better than the most troubled group of adolescents. Overall, both the presence of positive well-being and the absence of symptoms were necessary for ensuring the most advantageous school performance. These results highlight the importance of incorporating positive indicators of well-being along with traditional negative factors in more fully understanding relationships between individuals’ mental health and educational outcomes.