Addressing stigma remains a pressing HIV priority globally. Young Black men who have sex with men (YBMSM, ages 18–30; N = 474) completed an in-person baseline survey and reported their experiences of externalized stigma (i.e., racial and sexuality discrimination), internalized stigma (i.e., homonegativity), social support, and psychological distress (i.e., anxiety and depression symptoms). We used structural equation modeling to test the association between stigma and psychological distress, and examined whether social support mediated the relationship between stigma and psychological distress. Recognizing that these associations may differ by HIV status, we compared our models by self-reported HIV status (n = 275 HIV negative/unknown; n = 199 living with HIV). Our findings suggest that YBMSM who experience stigma are more vulnerable to psychological distress and may have diminished buffering through social support. These effects are accentuated among YBMSM living with HIV, highlighting the need for additional research focused on the development of tailored stigma reduction interventions for YBMSM.