The purpose of this study was to examine the long-term effects of perceived community disorder and social stigma on depressive symptoms among adolescent school dropouts. This study used 2-4 wave data of a Longitudinal Survey and Support Plan for Dropouts. Multivariate latent growth modeling indicated that social stigma was associated with greater number of depressive symptoms and had an indirect influence on depressive symptoms through self-esteem. In addition, perceived community disorder was related to greater number of depressive symptoms. Finally, self-esteem was negatively related to depressive symptoms and female adolescents reported more depressive symptoms than male adolescents. This study suggests that policy and social efforts are needed to reduce perceived community disorder and social stigma to prevent the depression in adolescent school dropouts.