Homelessness among older people in Canada is both a growing concern, and an emerging field of study. This article reports thematic results of qualitative interviews with 40 people aged 46 to 75, carried out as part of a mixed-methods study of older people who are homeless in Montreal, Quebec, Canada. Our participants included people with histories of homelessness (n = 14) and persons new to homelessness in later life (n = 26). Interviews focused on experiences at the intersections of aging and homelessness including social relationships, the challenges of living on the streets and in shelters in later life, and the future. This article outlines the 5 main themes that capture the experience of homelessness for our participants: age exacerbates worries; exclusion and isolation; managing significant challenges; shifting needs and realities; and resilience, strength, and hope. Together, these findings underscore the need for specific programs geared to the unique needs of older people who are homeless.