This paper explores the cycling between incarceration and homelessness among 18 women in Calgary, Alberta and Prince Albert, Saskatchewan employing community based research and arts-based research. Women who participated in the study highlighted the personal obstacles and societal barriers encountered before and after incarceration while identifying gaps in services. The objectives of the research were four fold: (1) to more fully understand the issues of homelessness and incarceration as it affects women, specifically Aboriginal women; (2) to work with women with lived experiences of homelessness and incarceration, community partners, and other collaborators to promote a greater understanding of these issues; (3) to provide recommendations and advocate for programming and policy changes to reduce the occurrence and harm associated with homelessness and incarceration for women; and (4) to effectively disseminate the findings to diverse audiences aimed at primary prevention strategies and improving services to reduce homelessness, recidivism, and other harms. Findings highlight the need for prevention and intervention supports for women living in poverty and the need to address the systemic and institutional racism and sexism that continue to deny women the right to a living income, safe and affordable housing, and human dignity.