Although several healthcare interventions have been developed to address HIV among young Black/African American men who have sex with men (YBMSM), the HIV epidemic in the United States continues to disproportionately burden this population. The current study examines previous healthcare discrimination and how it affects HIV intervention delivery. One hundred seventy-two YBMSM participated in the Peer Promotion of Wellness and Enhanced Linkage to Resources (PPOWER) project, which used a short, multi-faceted, community-level intervention based on Community Peers Reaching Out and Modeling Intervention Strategies (Community PROMISE). Data were collected at baseline, a 45-day follow up, and a 90-day follow up. Generalized Estimating Equations (GEE) were used to examine the effects of previous healthcare discrimination on outcomes related to HIV testing, alcohol and drug use, and sexual behaviors. Previous healthcare discrimination was found to moderate the relationship between time and intentions to test for HIV, perceptions of sexual risk, problem marijuana use, and problem other drug use, such that those who had experienced more healthcare discrimination showed greater improvements over time compared to those who had experienced less healthcare discrimination. The results of the current study suggest that a community-level peer intervention, in combination with a component to promote cultural competency and address prior experiences of discrimination in healthcare settings, may be highly effective for people who have experienced a barrier in their continuum of care as a result of racial discrimination.