Young Black gay, bisexual and other men who have sex with men (YB-GBMSM) are disproportionately burdened by HIV and often exhibit suboptimal engagement in HIV care. With the goal of increasing engagement in HIV care, we designed a culturally specific, theory-based group-level program, Brothers Building Brothers by Breaking Barriers (B6), which aimed to strengthen resilience and social capital among YB-GBMSM living with HIV. We conducted a pilot trial to evaluate the program’s acceptability and feasibility. Through clinic-based recruitment and community outreach events, we recruited and enrolled 71 YB-GBMSM into the study. Participants were randomized to either the B6 program or a control comparison program. Post-session evaluation surveys and in-depth qualitative interviews showed B6 to have high levels of acceptability and satisfaction. Specifically, participants described benefits to interacting in a group with other YB-GBMSM, and several described increased comfort with their own gay identities after participation. No adverse events or safety concerns were reported. However, there were challenges to feasibility, as reflected in recruitment and retention rates. The B6 program was highly acceptable among YB-GBMSM living with HIV; however, innovative program delivery methods and implementation strategies will be needed to improve recruitment and retention in future implementation of B6.