There are over half a million people living with HIV (PLWH) in the United States, all of whom require access to regular healthcare services in order to live with the disease. Borne out of the previously-fatal nature of HIV, the Ryan White HIV/AIDS Program (RWHAP) was created in 1990 in order to provide palliative services. Although the Affordable Care Act opened up additional health insurance options to PLWH, there remain questions about which healthcare payer type is associated with the best HIV health outcomes. To date, only a handful of studies have explored the association between healthcare payer type and HIV health, and few have examined this association using data collected after the Affordable Care Act was implemented. The principal purpose of this research was to identify the relationship between healthcare payer type and two key HIV health outcomes—specifically, viral suppression and two different measures of retention in care. The study sample consisted of 3,146 patients who attended at least one scheduled HIV primary care appointment at the University of Alabama at Birmingham’s 1917 Clinic within the 2015 calendar year. The 2016 calendar year served as the observation window. Multivariable logistic regression analyses were used to test associations between different single and multiple payer type combinations and HIV health outcomes. Results suggest that there is a meaningful and significant relationship between healthcare payer type and HIV health outcomes. In particular, receiving RWHAP supplementary services is associated with optimal health outcomes for PLWH, even when controlling for multiple sociodemographic characteristics. Furthermore, these findings suggest that healthcare payer type has a stronger association with retention in care than viral suppression. The results of this study provide timely insight into the criticality of health payer type in contributing to HIV health outcomes. They also have particular relevance for social work: Social workers have been integral to the provision of RWHAP wraparound services since the program’s inception, and their expertise in working with marginalized and/or vulnerable populations is as important now as ever.