This thesis is an investigation of the political participation of the homeless in Toronto, Canada. Whether or not the homeless in Toronto vote, the factors that influence their decision to vote, and the societal and structural impediments that exist to their participation are specifically examined. Qualitative interviews were conducted with the homeless, service providers, politicians, and election agencies in Toronto. This research revealed the interest and knowledge of politics among the homeless and the vital role that service providers and institutions serving the homeless play in the political engagement and process of voting for homeless citizens. An apparent disjunction between election agencies, politicians, and service providers also acted as an impediment to voting for the homeless. The barriers found in this research contribute to the literature on political participation that often disregards the homeless, and exhibit the systemic impediments that the homeless face to practicing their democratic right to vote.