In the United States, homelessness is often connected to traumatic events such as domestic violence, job loss, or post incarceration experiences, frequently resulting in substance use disorders, medical issues, and related mental illnesses. Although researchers have considered how homelessness and social service interventions affect sexual and gender minority youth, they have not adequately studied the causes and effects of homelessness among transgender women. The purpose of this interpretive phenomenological study was to bridge this gap in knowledge by exploring the experiences of chronically homeless transgender women. The research question focused on the lived experiences of chronically homeless transgender women who try to obtain social services from outreach workers. A purposive sample of 8 chronically homeless transgender women from the southeastern United States completed individual face-toface interviews. Using phenomenological strategies, the narratives were analyzed and interpreted into codes, categories, and themes. Four central themes were identified, including reasons for homelessness, the lived experience of chronic homelessness, experiences related to transgender identity, and involvement with social services. Participants faced barriers with social services agencies and outreach workers, including administrative demand for binary gender classification, blatant ignorance and discrimination, and a lack of trans-positive treatment facilities and shelters. The findings and recommendations from this study may advance positive social change by guiding the efforts of social service agencies and outreach workers to improve the quality of social services for transgender women.