We examined the role of stability and change in low-achieving urban African American adolescents' internal working models of their close friendships across multiple domains of functioning. We compared three groups of youth defined by their attachment orientation based on two ratings one year apart: (i) stable-secure (secure both years); (ii) stable-insecure (insecure both years); and (iii) changing orientation. We assessed psychological well-being, participation in problem behaviors, negative peer influences, school attitudes, and sexual behavior, hypothesizing that adolescents reporting stable secure internal working models of friendship would show the highest levels of functioning across all domains, followed by adolescents reporting instability in their friendships and adolescents reporting stable insecure orientations. Internal working models of friendship were assessed using a modified version of Hazan and Shaver's (1987) Adult Attachment Classifications. Across all domains, adolescents with stable secure orientations functioned better than those with stable insecure internal working models (e.g., less problem behavior and more positive school attitudes). The change group either resembled the stable-insecure group or fell in between the two stable groups. Analyses comparing outcomes based on the direction of change in attachment orientation (i.e., change to secure versus change to insecure) revealed main effects for problem behaviors and sex by change direction interaction effects for sexual behavior. These results suggest that low-achieving adolescents' attachment orientations change over time and are associated with deleterious outcomes. They extend attachment theory to adolescents' relationships with friends.