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This research demonstrates that homelessness significantly impacts a young persons academic engagement and attainment. Education is a topic that remains at the core of many debates regarding young people, and is central to our understanding of what can lead to better employment and economic opportunities and overall well-being. However, youth who experience homelessness face extreme forms of social exclusion. Many come to the streets having to forego formal education. A high percentage of youth who become homeless are forced to leave school, and the complexities of homelessness disrupt their educational experiences. It is unclear how the education system in Canada - a key statutory institution in young peoples lives - and the youth homelessness sector respond to the disengagement of these youth from school. In our common approaches to supporting homeless youth, Canadian aid agencies respond by providing emergency services, such as shelter, food, counselling, and other supports. Unfortunately, education is often not prioritized; rather, reactive emergency services adopt a neoliberal orientation towards young people to help them become independent, focusing on training them for the job market. The focus shifts to paid work and therefore self-sufficiency; as a result, education is considered a part of the young persons past rather than their future. This dissertation includes analysis and research findings that are directly informed by surveys and interviews with 40 homeless youth from York Region, in Ontario, Canada. Their narratives reveal that it is nearly impossible to remain in school while homeless due to housing and familial instability, mental health challenges, and challenges in school. Social exclusion theory and a critique of neoliberalism highlights why young people get stuck in a cycle of poverty and homelessness, and a psychoanalytic lens considers how listening to stories of suffering may awaken the self-reflexivity needed to evoke a more active response. Alongside the voices of youth and other scholars doing this important work, I insist that the education system, the homelessness sector, and community-based services prioritize educational attainment for homeless youth; this may allow them to remain in school, move forward with their lives, and prevent them from winding up on the streets.