There is a growing body of research examining the experiences of homeless older adults in Canada. Fourteen participants (11 males & 3 females) ages 46 to 57, recruited from the At Home / Chez Soi project in Winnipeg, completed individual semistructured interviews exploring their experiences of homelessness. Most participants reported lifelong intermittent homelessness. We identified 5 main themes that captured the experience of homelessness for older adults: pathways to homelessness; controlled lives; centrality of social relationships; shame and desire for self-reliance; and the challenge of disentanglement from the cycle of homelessness. This study provides insight into the experiences of homeless older adults in Canada. Findings suggest a need for policies and programs to meet the unique needs of homeless older adults.