This secondary analysis of the National Youth Risk Behavior Survey (years 2015–2019) examines associations between school-based protective factors (i.e., safe school environments and academic achievement) and HIV risk behaviors among sexually experienced adolescent gay and bisexual men (n = 644), a population with the highest prevalence of undiagnosed HIV infections. Demographics included Hispanics/Latinos (25%, n = 158), Other race/ethnicity (14%, n = 88), and non-Hispanic Blacks/African Americans (13%, n = 81). Adjusted models showed that protective factors reduced odds for early sexual debut, multiple sexual partners, sex under the influence of drugs/alcohol, and condomless sex, with an additive effect demonstrated when two protective factors were present. Hispanics/Latinos had greater odds of reporting multiple sexual partners and HIV testing, indicating opportunities for school-based HIV prevention and further research. Our findings provide support for school-based programs that aim to improve social and structural determinants of health and ultimately reduce adolescent HIV burdens.