When the COVID-19 pandemic emerged in early 2020, not only did it abruptly impede the progress that was being made toward achieving global targets to end the HIV pandemic, but it also created significant impacts on the physical and mental health of middle-aged and older men who have sex with men living with HIV. Utilizing a qualitative, community-based participatory research approach, we conducted semi-structured, one-on-one interviews with 16 ethnoracially diverse, middle-aged and older men who have sex with men living with HIV residing in Southern Nevada, to examine the different ways the COVID-19 pandemic directly impacted their physical and mental health, and explore how they eventually coped and thrived during the peak of the crisis. Using thematic analysis to analyze our interview data, we identified three prominent themes: (1) challenges to obtaining credible health information, (2) the physical and mental health impacts of the COVID-19-pandemic-imposed social isolation, and (3) digital technologies and online connections for medical and social purposes. In this article, we extensively discuss these themes, the current discourse on these themes in academic literature, and how the perspectives, input, and lived experiences of our participants during the peak of the COVID-19 pandemic could be critical to addressing issues they had already been experiencing prior to the emergence of the pandemic in 2020, and just as importantly, helping us best prepare in stark anticipation of the next potentially devastating pandemic.