An interpretive phenomenological approach was used to explore, illuminate, and interpret the lived experiences of 10 homeless African American women with criminal histories. A feminist lens was used to explore how race, gender, and criminal history coalesced to become women's pathways to crime and homelessness and to identify what services and interventions the women believed would be instrumental in helping them take new pathways away from homelessness and crime. The study findings indicated that women's pathways to crime were defined by traumatic childhood experiences, addiction, criminal role models, economic marginalization (the need for income), and damaged self-images. Pathways to homelessness were attributed to traumatic childhood experiences, addiction, low social and human capital, destructive personal relationships, criminal involvement, loss of public benefits, and pride. Common themes that the women defined as the essence of a homeless African American woman with a criminal history included feeling useless, degraded, insulted, discarded, and lacking in credibility. The study findings demonstrated the importance of providing homeless African American women with culturally relevant substance abuse treatment; gender-informed medical, psychiatric, and dental care; counseling that repaired self-esteem and self-image; access to subsidized housing; life skills training; employment readiness workshops; and spiritual resources to assist them in taking pathways away from crime and homelessness.