In addition to direct compensation (salaries and bonuses), fringe benefits such as employer-provided health insurance (EPHI) may also influence an individual’s decisions on actual and expected employment duration. This study analyzes the potential of EPHI in job retention among documented and undocumented farm workers in the United States at a time period when the farm sector is experiencing labor shortage crisis attributed to stricter immigration controls. In this study, farm worker-level data was preprocessed using Coarsened Exact Matching and analyzed under an ordered probit model. The results indicate that documented farm workers are generally responsive to EPHI in terms of both their actual employment duration and subjective working expectations. However, the EPHI did not significantly influence the subjective work expectations of undocumented farm workers. Moreover, the results imply that EPHI could not possibly be an effective tool for retaining undocumented workers on the farm once they are legalized.