ABSTRACT Some older gay men (50+) experience diminished quality of life (QOL) due to historical and ongoing discrimination in addition to living through a collective trauma—the pre-HAART era of the HIV/AIDS epidemic—characterized by the absence of treatment and rampant discrimination targeting gay men. A growing body of literature, however, illustrates that older gay men demonstrate remarkable resilience but little is known about how QOL is conceptualized and how these conceptualizations are potentially shaped by pre-HAART experiences. The current study drew on constructivist grounded theory methods to examine how QOL is conceptualized in light of the sociohistorical relevance of pre-HAART. Twenty Canadian based gay men aged 50+ participated in semi-structured interviews via Zoom. Ultimately, QOL is understood as experiencing contentment, which is made possible by the development and implementation of three key processes: (1) developing and cultivating meaningful connections, (2) growing into and embracing identity, and (3) appreciating the capacity to do what brings joy. QOL for this group is greatly informed by a context of disadvantage, and the demonstrated resilience warrants further investigation to meaningfully support the overall well-being of older gay men.