This article uses information from a large administrative database (N = 3941) to outline five ideal typical pathways into adult homelessness. The pathways are called ‘housing crisis’, ‘family breakdown’, ‘substance abuse’, ‘mental health’ and ‘youth to adult’. Then we explain why people on some pathways remain homeless for longer than others. People on a housing crisis or family breakdown pathway do not form strong friendships in the homeless subculture or accept homelessness as a way of life. Their homelessness is shorter. In contrast, people on the substance abuse and youth to adult pathways often become involved in the homeless subculture and engage in social practices that make it difficult to exit from homelessness. Their homelessness is longer. People on the mental health pathway also experience long-term homelessness, but they do not endorse homelessness as a way of life. They remain homeless because they have few exit options.