Understanding the socioecological contexts of gay men living with HIV is critical to addressing the environmental conditions that influence their lifetime experiences of housing insecurity and homelessness. In line with the strategies of the US Center for Disease Control and Prevention to end the HIV epidemic, it is of utmost importance to recognize how the allocation of available resources impacts health inequities affecting gay men living with HIV who experience housing insecurity and homelessness. Drawing from the World Health Organization’s social determinants of health (SDoH) framework, we used an exploratory, community-based research (CBR) approach to examine the lifetime experiences and important sources of support of gay men living with HIV at midlife who have experienced housing insecurity in Southern Nevada. Thematic analysis of our semi-structured interviews with 12 gay men living with HIV at midlife revealed three overarching themes: (1) challenges to obtaining housing and related support, (2) informal support from friends, and (3) formal support from community-based sources employing diverse support strategies. In this article, we discuss the different sub-themes we identified under these overarching themes and the implications of our findings from an SDoH perspective. We conclude with a discussion on the dire need to (1) highlight the considerable value of both informal and formal sources of support for the housing insecure, and (2) generate recommendations for interventions to address housing insecurity and homelessness with greater consideration for the impacts of SDoH in the work dedicated to helping gay men living with HIV at midlife overcome housing insecurity as they age.