The use of evidence-based strategies to increase access to medical care and improve health outcomes for people living with HIV is a major public health priority in the United States. As part of a multi-site evaluation funded under the Health Resources and Services Administration (HRSA), a process evaluation was conducted with the goal of understanding barriers and facilitators to the implementation of eleven heterogeneous interventions designed to engage and retain HIV positive women of color (WoC) in medical care. Findings identified barriers and facilitators to program implementation at five levels: (1) program; (2) team; (3) agency; (4) partner network; and (5) the larger socio-ecological context. We conclude with a series of recommendations that may be useful for the implementation of similar interventions focused on recruitment and retention of WoC in HIV medical care.