Sexual health education has been proven effective in improving adolescent sexual reproductive health outcomes. System-involved youth, including those in child welfare or juvenile justice systems, experience disproportionately poor outcomes as compared to youth in the general population, especially concerning STIs and early or unplanned pregnancies. Using logistic regression, this cross-sectional study examined the odds of condom use in a sample (n = 318; 61.3% males; 79.9% African American) of system-involved youth with multiple high-risk sexual behaviors. Specifically, it examined the impact of sexual health education, attitudes and beliefs about condoms, and the moderating effect of gender. The logistic regression models showed that youth were more likely to use a condom when exposed to comprehensive sexual health education (p < .05). Beliefs about condom effectiveness increased the odds of condom use in the second model (p < .01). Gender was not found to have a moderating effect. This study examined whether receiving comprehensive sexual health education and adolescent attitudes and beliefs towards condoms were associated with non-condom use using logistic regression in a sample of system-involved youth. Results suggest that comprehensive sexual health education could improve condom use in this vulnerable population.