Research suggests that contextual, self-system, and school engagement variables influence dropping out from school. However, it is not clear how different types of contextual and self-system variables interact to affect students' engagement or contribute to decisions to dropout from high school. The self-system model of motivational development represents a promising theory for understanding this complex phenomenon. The self-system model acknowledges the interactive and iterative roles of social context, self-perceptions, school engagement, and academic achievement as antecedents to the decision to dropout of school. We analyzed data from the Education Longitudinal Study of 2002-2004 in the context of the self-system model, finding that perception of social context (teacher support and parent support) predicts students' self-perceptions (perception of control and identification with school), which in turn predict students' academic and behavioral engagement, and academic achievement. Further, students' academic and behavioral engagement and achievement in 10th grade were associated with decreased likelihood of dropping out of school in 12th grade. (Contains 4 tables and 2 figures.)