CONTEXT:: HIV/AIDS in the United States continues to primarily impact men who have sex with men (MSM), with disproportionately high rates among black MSM. OBJECTIVE:: The purpose of this study was to identify factors that may influence engagement and retention of black MSM in HIV research. DESIGN AND PARTICIPANTS: This was a qualitative evaluation of study implementation within a multisite, prospective, observational study (HIV Prevention Trials Network 061, BROTHERS) that enrolled 1553 black MSM in 6 cities throughout the United States. Data collection for this evaluation included a written, structured survey collected from each of the sites describing site characteristics including staff and organizational structure, reviews of site standard operating procedures, and work plans; semistructured key informant interviews were conducted with site coordinators to characterize staffing, site-level factors facilitating or impeding effective community engagement, study recruitment, and retention. Data from completed surveys and site standard operating procedures were collated, and notes from key informant interviews were thematically coded for content by 2 independent reviewers. RESULTS: Several key themes emerged from the data, including the importance of inclusion of members of the community being studied as staff, institutional hiring practices that support inclusive staffing, cultivating a supportive working environment for study implementation, and ongoing relationships between research institutions and community. CONCLUSIONS: This study underscores the importance of staffing in implementing research with black MSM. Investigators should consider how staffing and organizational structures affect implementation during study design and when preparing to initiate study activities. Ongoing monitoring of community engagement can inform and improve methods for engagement and ensure cultural relevance while removing barriers for participation.