Abstract Public health departments, correctional institutions, and community-based organizations (CBOs) are increasingly working together to improve and support the health of inmates returning to the community, especially those with HIV. CBOs, and particularly the staff of CBOs, are key in providing HIV services to transitioning inmates; however, little data are available to characterize these staff. The purpose of this qualitative assessment is to describe the experiences and motivations of frontline staff involved in HIV-related service delivery to inmates and ex-offenders participating in the CDC/HRSA Corrections Demonstration Project. Eight focus groups with a total of 64 participants were held during a National CBO Meeting with frontline staff. Content analysis focused on staff experiences, motivations, and definitions of client success. Staff draw on personal, educational, and professional experiences to do their jobs, and they are motivated by a desire to help clients. Individuals in social work with similar experiences may find a unique niche working with this population. In fact, individuals with a heightened sensitivity for inmates and ex-offenders may consider the fields of social work, nursing, counseling, community psychology, or public health to enhance their training and better serve this population. Additional findings emphasize the importance of acknowledging the small steps along the continuum of client success.