<p>Despite recognition of the penal system’s impact on HIV vulnerability and known HIV disparities among Black Americans, particularly Black gay and bisexual men, limited research has examined the relationship between incarceration and HIV risk for formerly incarcerated Black men who have sex with men and women (BMSMW). This study aims to fill that gap by exploring the role of masculinity—specifically how both hegemonic and prosocial masculinity may influence sexual risk behaviors. Using data from the Public Health Management Corporation of Philadelphia, we assessed differences in masculinity by incarceration status among BMSMW (<i>n</i> = 239). Multivariate regression analyses tested the relationship between types of masculinity and sexual risk behaviors that increase HIV vulnerability in this population. Results revealed significant differences in masculinity ideology between men with and without incarceration histories. Additionally, different forms of masculinity were found to have varying effects (both positive and negative) on HIV risk. Our findings provide new insights into the complex relationship between incarceration, masculinity, and HIV vulnerability in this high-risk group. The study’s implications include the need for targeted health promotion and education in correctional settings, reentry policy reform, and further research into masculinity’s role in shaping health outcomes for this population. Additionally, there should be a focus on the systemic injustices of incarceration as an area for further exploration to understand its broader impact on health disparities and inequities.</p>