Purpose: To examine risk and resilience factors at multiple ecological levels related to Zimbabwean adolescents' practice of protected or unprotected sex. Methods: Data were collected from adolescents in eight secondary schools in Zimbabwe. A 140-item instrument designed by the authors assessed adolescent perceptions, behaviors, and attitudes. Youth who had engaged in sexual intercourse (n = 730) were included in analyses. Risk and resilience factors related to self, peer, family, and community domains were examined. Data were analyzed separately by gender using discriminant analysis to identify factors that predict whether youth engage in safe or unsafe sex. Results: Boys who engaged in safe sex were older, more likely to report their parents were there when needed, spent more time in extracurricular activities, and reported a lower drop out likelihood. Girls who engaged in safe sex worried about HIV/AIDS more than those who engaged in unsafe sex. Conclusions: Although both boys and girls need medically correct sexuality education, including education on HIV/AIDS and sexually transmitted diseases (STDs), the findings suggest that such education is not enough. Program planners must consider the influences of multiple ecological levels. Gender differences raise several issues for intervention.