Purpose: The purpose of this paper is to contextualise historically transnational labour experiences within guest worker programs in Canada and to provide a conceptual foundation for analysing work, learning and living relations with special attention to agricultural workers. Design/methodology/approach: The research is based on a critical review of the literature as well as secondary analysis of existing research on agricultural guest workers in Ontario, Canada. Findings: The authors argue that the structural conditions for these particular forms of work, learning and living relations have a long historical trajectory that dates back in North America to the nineteenth century. They outline a long trajectory of convergence of American and Canadian policies in this regard. In terms of work, learning and living experiences we show how shaped by race, class and citizenship relations, as well as by the learning that infuses their reproduction, intensification and contestation. Originality/value: The article sheds light on a system of transnational labour that is emerging in a wide range of economies around the world, but which has not, to date, been widely analysed in work and learning literature. (Contains 11 notes.)