This article examines the precarious learning-to-work transitions experienced by aboriginal youth in the Canadian oil sands mining industry. Drawing from an empirical case study of a mine-sponsored, pre-apprenticeship training programme, challenges experienced by programme participants, as well as their socialisation into the world of work are examined. As a group that is considered "at-risk," aboriginal youth in resource rich regions are also vulnerable to being targeted as a source of racialised labour by companies who want to appease local resentment over land dispossession and environmental pollution occurring on traditional lands. Informed by the sociology of Pierre Bourdieu and the concept of "vocational habitus," the inquiry critically examines the sets of dispositions that become embodied in training participants, which I argue align with the reputational risk management objectives of the sponsoring company.