The harms of youth homelessness are well described in the academic literature, but less is known about transitions into homelessness among at risk youth. Given the importance of preventing youth homelessness, and in particular, the first incidence of homelessness, quantitative and qualitative data from street involved youth in Vancouver were analyzed in order to determine significant factors associated with this transition and generate policy options for addressing this issue. Ultimately, this study recommends placing youth workers in secondary schools to support the academic and social development of at risk youth, as well as provide connections to appropriate community supports such as housing. This is the first known study to directly ask youth for their thoughts on how to prevent the first incidence of homelessness, and the results from this Capstone provides policy makers with opportunities for targeted interventions to address youth homelessness in Vancouver.