Previous studies that have explored the association between childhood trauma and homelessness indicate that traumatic events can lead to survivor distrust of interpersonal relationships and institutions, prolonged homelessness and poor health and social outcomes. The majority of this literature relies on quantitative data and fails to investigate the personal experiences of childhood trauma that are found to impact housing status later in life. Semi-structured, qualitative interviews were conducted with 25 men living in an urban area in Ontario who had spent more than 30 consecutive nights in an emergency shelter over the course of their housing histories. During data analysis, it was observed that all of the men had experienced some form of trauma or neglect in childhood which contributed to their entries into homelessness. Using a case study approach, three entry pathways into long term homelessness are described: 1) youth; 2) emerging or early adulthood; and 3) middle adulthood. Participants are classified into the pathways by the developmental period at which they first entered homelessness. These findings have implications for policy makers and service providers, as key intervention points are identified. Establishing effective interventions that address crises experienced at these points could assist with homelessness prevention across the life course.