A wave of restrictive immigration policies implemented over the past several decades dramatically increased immigrant detentions and deportations in the United States (U.S.), with important consequences for a host of immigrant outcomes. Still, questions remain as to how temporal and geographic variation in immigration enforcement within and across the U.S. shaped racialized legal status inequities in health and well-being, particularly among those employed in precarious occupations. To fill this gap, we interrogated the links between changes in county-level immigration enforcement and racialized legal status inequalities in musculoskeletal pain and social welfare benefits utilization among U.S. agricultural workers over nearly two decades (2002–2018). We merged data from three sources [(1) restricted-access, geocoded data from the National Agricultural Workers Survey (NAWS) (n = 37,619); (2) county-level immigration enforcement data from the Transactional Records Access Clearinghouse (TRAC); and (3) population data from the Census and American Community Survey (ACS)] and estimated linear probability models with year, month, and state fixed effects. We show that, in counties with high enforcement rates, workers—especially undocumented workers—were at increased risk of musculoskeletal pain, including pain that was severe. Heightened enforcement was also associated with declines in needs-based benefits utilization, especially among documented and U.S.-citizen non-White workers and undocumented White and non-White workers. Together, these findings highlight how changes in sociopolitical and legal contexts can shift and maintain racialized legal status hierarchies, with especially important consequences for the well-being of vulnerable workers.