Despite perfunctory characterisation of Canada’s Seasonal Agricultural Worker Program (SAWP) as a ‘triple win’, scholars and activists have long admonished its lack of government oversight, disrespect for migrant rights and indentureship of foreign workers. This article contends that the SAWP is predicated upon naturalised, deeply engrained and degrading beliefs that devalue Black lives and labour. Based on twenty months’ ethnographic fieldwork in the Okanagan Valley, British Columbia, Canada, it reveals the extent to which anti-Black racism permeates, organises and frustrates workers’ lives on farms and in local communities. It situates such experiences, which workers characterise as ‘prison life’, in the context of anti-Black immigration policy and the workings of racial capitalism. This ethnography of Caribbean migrants not only adds perspective to scholarship hitherto focused on the experiences of Latino workers, but it also reinforces critical work on anti-Black racism in contemporary Canada.