Background: Homelessness among women and the multiple vulnerabilities they endure (sexual exploitation/human trafficking, violence, and mental health issues) is a perpetually unresolved issue in the U.S. and globally. Methods: This study is based on qualitative in-depth interviews accompanied by brief socio-demographic surveys conducted among 32 total participants, consisting of cisgender females (n = 17) and cisgender males (n = 15) experiencing homelessness at a large public library. Results: Of the women, 35% were White, 35% Latina, 18% African American/Black, and 18% LGBT. Half of all participants said in qualitative interviews that they witnessed violence against women, and/or experienced unwanted harassment/sexual exploitation; one in three described suspected human trafficking. Of the women interviewed, half struggled with mental health symptoms, feelings of hopelessness, and nearly all reported isolation; approximately one-third had substance use issues. Many described an inadequate number of emergency and long-term shelters available for women facing homelessness; many had to wait or saw other women waiting to get into shelters and faced abuse on the streets in the meantime. Conclusion: The emergent themes showed that women face a “cycle of perpetual vulnerability” with three relational pathways: iterated trauma from chronic abuse/violence inflicted on them, a state of paralysis due to inadequate availability of supportive services, shelters, and mental health resources to cover all women living on the streets, leaving women susceptible to being a target phenotype for predators.