Internalized HIV stigma plays a detrimental role in terms of linkage to HIV care and adherence to antiretroviral treatment. Yet, little is known regarding the association of internalized HIV stigma with retention in HIV care. We conducted an analysis of interview and medical record abstraction data collected from 188 HIV positive men and women receiving HIV care in Miami, Florida. Demographic characteristics, HIV risk behaviors and care related factors were used to explore the association of internalized HIV stigma with retention in care in a Poisson regression analysis. The relationship of internalized HIV stigma and retention in care was moderated by the patient's level of engagement with an HIV care provider (p=0.004) in that higher levels of provider engagement were significantly associated with higher retention in care rates among patients with moderate levels of internalized HIV stigma. Additionally, retention in care rates were lower for females than for males and for 18-44 year olds than for individuals 44 years and older. Our findings indicate that higher levels of patient-provider engagement may reduce the impact that internalized HIV stigma has on retention in HIV care for some patients. Interventions with HIV care providers or patients to enhance patient-provider engagement may be beneficial.