For more than fifty years, Jamaican farm workers have been seasonally employed in Canada under the Seasonal Agricultural Worker Program (SAWP). In Canada, these workers live and work in conditions that make them vulnerable to various health issues, including poor mental health. This ethnographic study investigated Jamaican SAWP workers’ mental health experiences in Southern Ontario. Several common factors that engender psychological distress among Jamaican workers, ranging from mild to extreme suffering, were uncovered and organised into five themes: (1) family, (2) work environments and SAWP relations, (3) living conditions and isolation, (4) racism and social exclusion, and (5) illness and injury. I found that Jamaican workers predominantly use the term ‘stress’ to articulate distress, and they associate experiences of suffering with historic plantation slavery. Analysis of workers’ stress discourses revealed their experiences of psychological distress are structured by the conditions of the SAWP and their social marginalisation in Ontario. This article presents and discusses these findings in the context of SAWP power dynamics and concludes with policy recommendations aimed at improving the mental health of all SAWP workers. In foregrounding the experiences of Jamaican workers, this study addresses the dearth of research on the health and wellbeing of Caribbean SAWP workers.