The 2020 National HIV AIDS Strategy (NHAS) sets a target of 90% of diagnosed people living with HIV (PLWH) retained in HIV care. Access to Care (A2C) was a national HIV linkage, re-engagement, and retention in care program funded by AIDS United with support from the Corporation for National and Community Service that aimed to link and retain the most vulnerable PLWH into high-quality HIV care. This study explores the barriers and facilitators of implementing the A2C program from the perspective of program staff. Ninety-eight qualitative interviews were conducted with staff at implementing organizations over the 5 years of the project. Barriers included challenges with recruiting and retaining participants, staffing and administration, harmonizing partnerships, and addressing the basic and psychosocial needs of participants. Facilitators included strong relationships with partner organizations, flexible program models, and the passion and dedication of staff. Findings will inform the development of future programs and policy.