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In Australia and Canada, working holidaymaking is rationalized on the basis of encouraging cultural exchange among youth. Yet, in both countries, there is mounting evidence that working holiday programs are operating as back-door migrant work programs to help fill demands for labor in occupations and industries characterized by precarious jobs undesirable to locals. As scholarship on working holidaymakers’ labor market participation is more developed in Australia than in Canada, and administrative data available are also more extensive therein, this article sheds new light on the Canadian case vis-à-vis the Australian example. In exploring regulatory strategies adopted by these two settler states and their effects, comparative analysis of administrative data and historical and contemporary immigration and labor and employment laws and policies reveals how nationally specific program design can foster similar ends: precariousness among participants in the industries in which working holidaymakers are concentrated, including agriculture, tourism, and accommodation and food services. It also shows that stratification between working holidaymakers more closely approximating the image of the “cultural sojourner” and those who are effectively migrating for work purposes takes shape principally along the lines of source country in both countries.