Community based organizations (CBOs) play a frontline role in HIV/AIDS prevention activities. CBOs face formidable challenges to effective delivery of HIV prevention services including client characteristics such as homelessness and CBO characteristics such as limited resources and staff turnover. Despite these obstacles, CBOs are generally well positioned to deliver services to specific high-risk populations because they understand their local communities and are connected to the groups they serve. [C1]This qualitative study illustrates that structural, sociocultural, organizational, and individual client factors both facilitate and act as barriers to delivery of HIV prevention services. These challenges and successes help identify critical technical assistance needs.