Background <p>The purpose of this study was to examine the long-term effects of social stigma, career optimism, community disorder, and community ties on depressive symptoms among adolescent school dropouts.</p> Methods <p>We used wave 2–4 data (2014–2016) from the Dropout Youth Panel Survey conducted by the National Youth Policy Institute. Data from 427 adolescents (mean age = 17.77 years) were used. Generalized estimating equations were used to examine the longitudinal associations among variables.</p> Results <p>Social stigma, career optimism, and community disorder explained depressive symptoms among the participants. First, social stigma was positively correlated with depressive symptoms. Second, career optimism was negatively associated with depressive symptoms. Third, community disorder was positively correlated with depressive symptoms. Fourth, the longitudinal relationship between community ties and depressive symptoms was not significant.</p> Conclusions <p>This study has implications for identifying the influence of individual and environmental variables on depressive symptoms among adolescent school dropouts. To prevent such symptoms, specific policy and social efforts are required—such as public awareness campaigns to reduce social stigma, mentoring and vocational training programs to foster career optimism, and initiatives to improve public safety and community environments in order to mitigate community disorder.</p>