Homelessness is a major social issue in all Western countries. In France, many homeless persons do not have access to the accommodation and help with social reintegration provided in long-stay hostels, and remain on the streets or in other forms of emergency shelter. The objective of the present study is to identify the variables preventing access to these hostels and, more generally, to a process of social reintegration. We compared a group of 10 individuals housed in long-stay hostels with a group of 16 who were still living in the streets. All participants were assessed on the Hospital Anxiety and Depression Scale and underwent a semi-structured interview. Results showed that individuals who had not been admitted to a hostel were characterized by high levels of depression and anxiety, the attribution of responsibility to external factors, a vagrant lifestyle, a lack of social support, a negative approach to reintegration, and an inability to look to the future. This study highlights various factors explaining the reintegration difficulties encountered by a proportion of the homeless population. It suggests new ways of improving support for the homeless.