A single employable adult relying on social assistance in Ontario receives approximately $7,500 annually on which to live. In spite of this very low amount, singles make up Ontario’s fastest growing household group on social assistance. In 2012, a review of the province’s social assistance system recommended an immediate $100 increase in monthly benefit levels for singles. This raises three key questions: How did Ontario’s social assistance system develop into its current form? What do social assistance recipients do with increased monthly benefits? To what extent might increased benefit levels lead to higher caseloads? The present dissertation comprises three essays—each one looking to answer one of the above questions, and each with a different methodological approach. Each essay also has a different geographical focus: the first looks exclusively at Ontario; the second looks at Ontario’s welfare system while interviewing a sample of Toronto-based recipients; and the third looks at six provinces, including Ontario. The first essay offers a historical consideration of the emergence and development of Ontario’s social assistance system. With the 1965-1975 period being its major focus, the essay finds that the Great Depression prompted senior levels of government in Canada to spend more on income assistance, and that the strength of Canada’s post-World War II economy made it more palatable for both the Canadian and Ontario governments to expand social assistance coverage and increase benefit levels. For the second essay, I interviewed 10 Toronto-based men on social assistance, asking each of them detailed questions about their monthly budgets. Five themes emerged from the research, and each theme forms the basis for a hypothesis that may be examined in future research. For the third essay, I undertook an OLS regression analysis of determinants of social assistance caseloads for single employables across six Canadian provinces over the 1989-2010 period. Results suggest that the determinant of singles caseloads in a given year with the highest amount of statistical significance is the previous year’s caseloads. What is more, of all the independent variables—and aside from the previous year’s caseload level—only British Columbia’s stricter administrative rules attain five percent significance or better.