Background: Women's pathways into homelessness are gendered, shaped by family dysfunction, economic precarity, and high rates of violence. Despite the profound implications for women and their children, evidence from Ethiopia remains scarce. This study explored women's early-life experiences, trajectories into and through homelessness in Addis Ababa, and the challenges and resources related to community reintegration. Methods: We conducted an exploratory qualitative study in Addis Ababa, Ethiopia, in December 2023 using semi-structured interviews. Women of reproductive age experiencing homelessness were purposively recruited through a local civil society organisation ( Results: We developed four themes: "Childhood trauma from abuse", "Sexual violence", "Barriers to leaving street life", and "Sources of hope". The analysis identified three distinct trajectories - Chaotic, Circuious, and Linear - which differentiated women's movement into and through homelessness. Women's accounts revealed trajectories in which early harm within families and households extended into street-based victimisation. This reinforced heightened insecurity and limited their options to exit homelessness. Across themes, cumulative violence was sustained by social and structural constraints, including substance use and limited access to formal protection and justice. Despite these constraints, women emphasised sources of hope, including faith, perseverance, and aspirations to care for and support their children. Conclusion: Women's trajectories into and through homelessness in Addis Ababa were shaped by cumulative, gendered violence across the life course. These results suggest that reintegration pathways must be tailored to specific trajectories, providing trauma-informed care for chaotic routes and economic safety nets for circuitous ones. Such an approach highlights the need for locally grounded, trauma-informed, and gender-responsive interventions.