Multiple studies have shown that subtherapeutic appointment adherence and medication adherence are associated with worse clinical outcomes for people living with HIV disease. Thus, poor appointment and medication adherence diminish individual and community HIV control and transmission. Yet not enough is known about interventions that can improve retention in HIV care. The purpose of this study was to test an intervention to improve retention and/or medication adherence in a public clinic in the Deep South. One hundred participants with retention or medication adherence difficulties were randomized to either a six-month intervention or usual care, and followed longitudinally for one year. The intervention was multidimensional, based on the Information-Motivation-Behavioral Skills (IMB) model. The intervention addressed information about HIV and the importance of retention/adherence, motivation to be retained and/or adhere to medications, and the behavioral skills needed to manage and maintain these healthy behaviors in a combination of face-to-face and telephone sessions. The proportion of those with at least one visit in each four-month block (third) of the year increased in those with minimal exposure to the intervention (three out of eight intervention contacts) as compared to those with less intervention exposure (p = 0.098). Those with at least this minimal exposure averaged a significantly higher number of thirds that included a clinic visit as compared to those with less intervention exposure (p = 0.013). The intervention did not demonstrate a significant effect on medication adherence, though this is contradictory to a previous study testing a version of this intervention designed to address only medication adherence. Further study to increase uptake of the intervention is needed to increase its efficacy.