One of the primary functions of the attachment behavioral system is to regulate emotional experience under conditions of threat. Although research supports this association among infants and adults, few studies examine the relation between emotion and attachment in middle childhood. The present study sought to provide further evidence for the predictive and concurrent validity of the Affect Task, a cartoon-based measure depicting socially ambivalent scenarios that prompts for representations of attachment figures, affect regulation and coping strategies, and the consideration of the possibility of mixed or sequentially distinct emotions. Twenty children participating in an afterschool program called ‘I Have a Dream’ (IHAD) were followed from elementary school to late middle school. The Affect Task was administered at Time 1 (age 7) and Time 2 (age 9); while the Strengths and Difficulties Questionnaire, an observer-based measure of emotional and behavioral function was completed by counselors at Times 1 (age 7), 2 (age 9), 3 (age 11), and 4 (age 13). Overall, children who had higher levels of felt security and emotion understanding as indicated by Affect Task responses had significantly lower levels of observed emotional and behavior problems both concurrently and predictively at Time 2 and Time 3, but not Time 4. There were decreased total difficulties observed over time with continued participation in the IHAD program. This study highlights the importance of afterschool programs in high-risk communities, as interventions aimed at providing positive social and academic support.