Stigma is a fundamental cause of health inequities. Guided by the Adaptive Leadership Framework for Chronic Illness (ALFCI), this descriptive qualitative study explored the challenges of stigma and disclosure experienced by women with HIV (WWH) in the Southern United States. A convenience sample of 22 WWH aged 36 to 62 years were interviewed for this study. Analysis of participant interviews revealed that WWH face a multitude of stigma-related technical and adaptive challenges, which are consistent with the ALFCI. Once identified, technical challenges, such as recognizing the need for support, lack of trust, and fear of rejection, can be overcome by technical work, including providing assistance with HIV disclosure and building a trusted network. By identifying specific adaptive and technical challenges faced by WWH and engaging in technical and adaptive work, the WWH and the provider can reduce the fear of disclosure and the effect of stigma.