This study investigated the effects of individual and contextual factors (students and classrooms) on academic engagement by adopting an analytical approach based on hierarchical linear modeling. The participants in this study included 906 high school students (42.7% male) from 42 classrooms in South Korea. We established that achievement value and teachers' autonomy support had a statistically significant positive impact on academic engagement at both the student and classroom levels. However, teachers' academic pressure had a positive impact on academic engagement only at the classroom level. Cross-level interaction effects between the student and classroom levels, achievement value (LV 1) and autonomy support (LV 2), teachers' academic pressure (LV1) and achievement value (LV 2), and those on teachers' academic pressure at both levels were also identified.