The purpose of this study was twofold: (1) to determine the role of transitional housing in ending homelessness for women and (2) to explore how gender-specific experiences of homelessness may inform housing service delivery models. Using a participatory research methodology, photovoice, and focus group discussion, nine women with lived experience of homelessness were engaged over 10 weeks in a process of reflection and critical dialogue about their previous experiences in a YWCA transitional housing facility and their current YWCA permanent housing in Calgary, Canada. Through this process women revealed that the key aspects of transitional housing that helped them exit homelessness were the interplay of four important factors: safety, time, a community of women with similar experiences, and a supportive environment with access to appropriate services in which to recover from trauma. Although moving directly from homelessness to permanent housing may be appropriate for some women, findings from this study demonstrate that this may not be the case for all. Our results suggest that once permanently housed women, especially those with histories of trauma, struggle with the trade-off between the rules that kept them safe in transitional housing and living as independent, autonomous adults in the community.