This study delves into the complex dynamics among risk experiences, emotional and behavioral symptoms, and the educational engagement of children with incarcerated fathers. Drawing data from 64 currently incarcerated fathers, their adolescent children, primary caregivers, and teachers, the research reveals that both socioeconomic and parental incarceration-specific adversities contribute to heightened externalizing and internalizing problems. Notably, socioeconomic risk factors wield a more substantial influence on these psychopathologies. Externalizing problems emerge as key mediators, outweighing internalizing problems in linking socioeconomic risk experiences to children’s attitudes toward school. Total indirect model analysis underscores that general risk experiences negatively impact children’s school attitudes and belongingness through both internalizing and externalizing problems. Findings underscore the significance of children’s socioeconomic adverse experiences, with a pronounced impact on behavioral adjustment and a notable contribution to emotional adjustment. This dual influence, particularly emphasizing behavioral aspects, subsequently shapes their involvement and adaptation within the school system. The study advocates for targeted interventions and policy measures, highlighting the necessity to bolster caregivers’ social and economic resources, actively engage incarcerated parents in decisions related to their children’s education and well-being, provide support to teachers in identifying and addressing challenges faced by children in schools, and deliver personalized psychological assistance for these children. These interventions facilitating the educational involvement are pivotal for disrupting the cycle of disadvantage and criminal behavior.