Positive school environments and school belonging have been associated with a variety of positive academic, social, and psychological outcomes among youth. Yet, it is not clear how these constructs are related, and few studies have focused on urban at-risk youth with disabilities. This study examines baseline survey data from 136 low-income African American and Latino students in grades 5 to 12, most of whom have disabilities, recently transferred following a school closure. Using structural equation modeling, we tested a model that examined the relationships among school stressors and resources, school belonging, academic outcomes (school satisfaction and academic self-efficacy), and psychological outcomes (anxiety and depression). This model was an excellent fit with the data, and findings indicate that school belonging plays a central role in explaining how school context can affect both psychological and academic outcomes. This model has implications for school-based interventions that can enhance student success and well-being.