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 demonstrated that the introduction of antiretroviral therapy led to an increased life expectancy yet early onset of comorbidities; however, they failed to address the challenges that people 50 years old or older face, as well as other factors affecting their quality of life. 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 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. These findings could give healthcare providers insights on the population in question, their challenges, and how to better address their concerns. The methodology of the study was a phenomenological approach; data were collected through 10 participant responses during recorded telephone interviews. The recorded data were transcribed before being analyzed using Nvivo software. The results 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 those who are older and suffering from HIV by providing information to healthcare professionals who can improve or maintain the health of this population.