This study evaluated effects of Positive Action (PA), a school-based social-emotional and character development program, on self-esteem levels and processes among minority, low-income, urban youth. A matched-pair, cluster-randomized controlled trial was conducted in 14 Chicago Public Schools with outcomes assessed longitudinally for a cohort of youth followed from Grades 3 to 8. A total of 1,170 students participated in the study (53% female, 48% African American, and 27% Hispanic). Students in PA schools had more favorable change and endpoint scores on indices of self-esteem in the domains of peer and school and use of both adaptive and (to a lesser extent) maladaptive processes for developing and maintaining self-esteem. These results align with areas of emphasis within the PA program and illustrate how important areas of impact on self-esteem-related outcomes may be overlooked without differentiated assessments of both self-esteem levels and processes.