The present observational study was conducted to uncover potential differences in the risk of experiencing high occupational heat strain during agriculture work between migrants and their native coworkers, as well as to elucidate the factors that may contribute to such differences. The study took place over the period from 2016 through 2019 and involved monitoring 124 experienced and acclimatized individuals from high-income (HICs), upper-middle-income (UMICs), as well as lower-middle- and low-income (LMICs) countries. Baseline self-reported data for age, body stature, and body mass were collected at the start of the study. Second-by-second video recordings throughout the work shifts were captured using a video camera and were used to estimate workers’ clothing insulation, covered body surface area, and body posture, as well as to calculate their walking speed, the amount of time they spent on different activities (and their intensity) and unplanned breaks throughout their work shifts. All information derived from the video data was used to calculate the physiological heat strain experienced by the workers. The core temperature of migrant workers from LMICs (37.81 ± 0.38 °C) and UMICs (37.71 ± 0.35 °C) was estimated to be significantly higher compared to the core temperature of native workers from HICs (37.60 ± 0.29 °C) (p < 0.001). Moreover, migrant workers from LMICs faced a 52% and 80% higher risk for experiencing core body temperature above the safety threshold of 38 °C compared to migrant workers from UMICs and native workers from HICs, respectively. Our findings show that migrant workers originating from LMICs experience higher levels of occupational heat strain, as compared to migrant workers from UMICs and native workers from HICs, because they take fewer unplanned breaks during work, they work at a higher intensity, they wear more clothing, and they have a smaller body size.