This study examined the extent to which antisocial behavior, parenting, and school connectedness moderated the association between peer deviancy in preadolescence and externalizing problems in early adolescence. The participants included 500 boys and girls, most of them African Americans. Peer deviancy was measured with teacher reports of aggressive-disruptive behavior for classmates identified by target children as friends. Parents provided information on parenting practices (nurturance and harsh and inconsistent discipline) and children's antisocial behavior. Children reported on their school connectedness and externalizing behaviors (delinquency and substance use) in preadolescence and early adolescence. Externalizing problems in early adolescence were associated with preadolescent externalizing and antisocial behavior and older age. Peer deviancy predicted externalizing problems only when combined with higher levels of antisocial behavior and negative parenting. School connectedness, gender, and ethnicity did not moderate the link between peer deviancy and externalizing problems. © 2009 SAGE Publications.