Protective and risk factors associated with rates of early sexual debut and risky sexual behaviors for a sample of low-income adolescent boys were examined using bioecological theory framed by a resiliency perspective. Protective processes examined include a close mother-son and father-son relationship, parental monitoring and family routines, as well the adolescent boy's academic achievement, expectations, and school recognition. The risk factors assessed were adolescent race and delinquent behaviors, if the adolescent was born to a teenage mother, family structure, monthly family income, risky neighborhood environments, family of origin welfare receipt, and maternal education. Waves one and two of Welfare, Children, and Families: A Three-City Study was used (N = 539; ages 10 to 14 years). Associations between early sexual debut and risky sexual behaviors with individual, family, and neighborhood protective and risk factors were addressed through a series of d-probit and Ordinary Least Squares (OLS) multiple regression techniques. Findings show that parental monitoring, family routines, and academic achievement protect adolescent boys from early sexual debut and risky sexual behaviors, while delinquent behaviors, single parenthood, and adolescent race place adolescent boys at risk for early sexual debut and risky sexual behaviors.