Since the introduction of antiretroviral therapy, the survival rate of infected HIV patients has been on the rise with a predicted increase by 2030. The longer a person lives with the virus, the more prone to HIV-associated chronic diseases he or she becomes, but it is not clear whether these diseases are solely from aging with the virus or from long-term use of antiretroviral therapy. Scientists, however, have failed to address the challenges of aging and living with HIV. The purpose of this study, driven by both social constructivism as well as the advocacy worldview, was to explore the lived experiences of participants older than 50, living with HIV for at least 20 years, to gain an understanding of how long-term use of antiretroviral therapy relates to the onset of comorbidities, which would lead to a new understanding of the challenges they face. The methodology of the study was a phenomenological approach; data were collected through participants’ responses during recorded telephone interviews before being transcribed and analyzed using Nvivo software. Findings indicated that these participants live in daily survivorship filled with constant struggle between a series of comorbidities that develop overtime. Additionally, their journey is not only coupled with unmet needs of today but also with uncertainties of tomorrow. The findings can improve the current social conditions of the population in question by providing information to healthcare professionals so they can better address their needs, thus improving and maintaining their health