Through an ecological theory lens, the purpose of the current study was to examine variables that most strongly influence middle school academic achievement among a sample of 240 sixth-eighth graders in the Midwest. The purpose was to explore whether student academic organizational practices uniquely predicted middle school achievement, and whether intrapersonal variables (engagement, metacognition, and student organization/academic practices) moderated relationships between contextual factors (parent, teacher, and peer support) and achievement. The combination of contextual and intrapersonal variables accounted for variance in achievement. Engagement was the intrapersonal factor that consistently contributed to the models. Metacognition moderated peer support and academic achievement. When school engagement becomes a primary focus, versus only attempting to remediate metacognitive and organizational deficits, this can pave a more accessible path for both educators and parents to teach other skills that are essential to educational attainment and occupational success. Implications for interventions targeting student participation, attention, and effort are discussed.