In the last few years, engagement in medical care among individuals living with HIV has become a major priority among HIV medical providers and public health researchers. Engagement in medical care is an important concept as it involves the process of linking newly diagnosed individuals into medical care and retaining those individuals in care throughout the course of their infection. Although there have been major advances in the management of HIV, like the advent of Highly Active Antiretroviral Therapy, morbidity and mortality due to HIV cannot be fully reduced if the individual does not optimally retain in care. Retention in HIV medical care has become an emerging topic in HIV research, but there still remains a scarce amount of research on how to properly define retention, understand its predictors, and how it impacts HIV outcomes. The purpose of this dissertation was to evaluate retention in HIV medical care among individuals diagnosed with HIV and seeking care at an urban infectious disease clinic in Kentucky. The three specific aims of this dissertation were to: (1) compare methods in measuring retention in HIV medical care; (2) determine the predictors of poor retention in care and assess the effect of non-HIV related comorbidities have on retention over time; and (3) determine the impact early retention to medical care has on time to viral load suppression and rebound among individuals initiating Highly Active Antiretroviral Therapy. A retrospective cohort study was conducted employing a medical chart review, and patients who sought HIV care at the Bluegrass Care Clinic between January 1st 2003 and May 1st 2011 were eligible for the study. There were 1,358 patients included in the study and these individuals were followed until December 31st, 2011. The results suggested that individuals living with HIV should seek care at least once every six months (visit constancy) and that only 48.6% of the study population obtained optimal retention over time. Over time the rate of retention decreased among the study sample and those with optimal retention were more likely to suppress their viral loads compared to poor retainers.