This article reports the qualitative findings of a multimethod study of the homeless population in Toronto, Canada. The qualitative component sought to identify how people become homeless and why some individuals remain homeless for an extended period of time or cycle in and out of homelessness (the chronically homeless). In-depth, semistructured interviews were conducted with 29 homeless adults. The findings suggest that people both become and remain homeless due to a combination of macro level factors (poverty, lack of employment, low welfare wages, lack of affordable housing) and personal vulnerability (childhood abuse or neglect, mental health symptoms, impoverished support networks, substance abuse). Chronically homeless individuals often reported experiences of severe childhood trauma and tended to attribute their continued homelessness to a substance abuse problem. It is concluded that both macro and individual level factors must be considered in planning programs and services to address the issue of homelessness in Canada.