The purpose of this qualitative study was to develop an in-depth understanding of the experience of unsheltered homelessness in Fort Worth, Texas. Eighteen individuals participated in the study; 13 were full-time residents of Fort Worth and 5 were traveling through the area via freight train. All reported long-term histories of unsheltered homelessness. Interviews were conducted in naturalistic settings; for example, on the street, under bridges, and in camps. Results indicated that the participants entered homelessness through diverse paths, but all of these paths were characterized by loss and social isolation. Many described homelessness as a threatening and dangerous experience; relying on strong street-based social networks and their own personal strengths for survival. Participants viewed shelter service providers as sources of stress and stigma to be avoided but heavily utilized street outreach services and faith-based missions. The overemphasis by providers on “fixing” people, rather than addressing immediate needs, made many participants ambivalent about traditional services. This study supports the use of nontraditional housing interventions and robust community-based approaches to care for individuals experiencing unsheltered homelessness.