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This study examined how parenting factors were associated with adolescent problem behaviors among urban minority youth and to what extent these relationships were moderated by family structure and gender. Sixth-grade students (N = 228) reported how often they use alcohol, smoke cigarettes, or engage in aggressive or delinquent behaviors; a parent or guardian reported their monitoring and other parenting practices. Findings indicated that boys and those from single-parent families engaged in the highest rates of problem behavior. More parental monitoring was associated with less delinquency overall, as well as less drinking in boys only. Eating family dinners together was associated with less aggression overall, as well as less delinquency in youth from single-parent families and in girls. Unsupervised time at home alone was associated with more smoking for girls only. Implications for prevention interventions are discussed.