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In this study, we explore how high schools, through their structures and organization, may influence students' decisions to stay in school or drop out. Traditional explanations for dropout behavior have focused on students' social background and academic behaviors. What high schools might do to push out or bold students has received less empirical scrutiny. Using a sample of 3.840 students in 190 urban and suburban high schools from the High School Effectiveness Supplement of the National Educational Longitudinal Study of 1988, we apply multilevel methods to explore schools' influence on dropping out, taking into account students' academic and social back- ground. Our findings center on schools' curriculum, size, and social relations. In schools that offer mainly academic courses and few nonacademic courses, students are less likely to drop out. Similarly, students in schools enrolling fewer than 1,500 students more often stay in school Most important, students are less likely to drop out of high schools where relationships between teachers and students are positive. The impact of positive relations, however, is contingent on the organizational and structural characteristics of high schools. [ABSTRACT FROM AUTHOR]