Situated within a positive psychology perspective, this study explored linkages between adolescent students' positive subjective well-being and their levels of engagement in schooling. Specifically, using structural equation modeling techniques, we evaluated the nature and directionality of longitudinal relationships between life satisfaction and student engagement variables. It was hypothesized that adolescents' life satisfaction and student engagement variables would show bidirectional relationships. To test this hypothesis, 779 students (53% female, 62% Caucasian) in a Southeastern US middle school completed a measure of global life satisfaction and measures of cognitive, emotional, and behavioral engagement at two time points, 5 months apart. A statistically significant bidirectional relationship between life satisfaction and cognitive engagement was found; however, non-significant relationships were found between life satisfaction and emotional and behavioral student engagement. The findings provide important evidence of the role of early adolescents' life satisfaction in their engagement in schooling during the important transition grades between elementary and high school. The findings also help extend the positive psychology perspective to the relatively neglected context of education.