Using a multidimensional, integrative approach this study examined the influence of social position factors (nativity, economic hardship, and language) and environmental contexts (community trauma, geographic location, and discrimination) on three domains of school engagement (cognitive, behavioral, and relational) among a community sample of first- and second-generation Latino adolescents. Findings from this study reveal that both social position and environmental contexts significantly and differentially predicted each of the three domains of school engagement. Participants (n = 306) included students from 11 high schools in two US cities. Fifty-three percent were first-generation immigrants and 80% were born, or had a parent from, Mexico or Central America. Results indicated that all three social position factors (nativity, economic hardship, and language) and two of the three environmental contexts (community trauma exposure and discrimination) significantly and differentially predicted each of the three domains of school engagement. Findings emphasize the direct effects of student's social positionality and environmental contexts on their engagement in school.