Although interest on older homelessness is gaining momentum, little research has considered the experiences of first-time homelessness from the perspective of older adults themselves. This constructivist grounded-theory study addresses this gap by exploring how societal perceptions of homelessness and aging shape access to housing, services, and perceptions of self for 15 older adults residing in emergency homeless shelters in Montreal, (Quebec, Canada). Findings revealed that homelessness evoked a grief response characterized by shock, despair, anger, and in some cases, relief. Connecting and receiving support from other shelter residents and staff helped participants to acknowledge and grieve their losses. However, difficult shelter conditions, the stigma associated with aging and homelessness, and not having their grief recognized or validated served to disenfranchise grief experiences. Conceptualizing later-life homelessness as disenfranchised grief contributes to the aging and homelessness literature while providing new avenues for understanding and validating the experiences of a growing population of vulnerable older adults.