The agriculture industry has high rates of injury and illness. Furthermore, the average age of US farmers is 58 years old. Chronic conditions are more common among older populations and often require management by a health professional. Farmers face barriers when seeking healthcare. These barriers include limited free time, shortage of providers in rural areas, limited funds, and poor health insurance. In addition, lack of quality health insurance and concerns about paying for healthcare are identified as barriers to healthcare-seeking behavior among farmers. More research is needed to examine the impact of type of health insurance on utilization of specific types of healthcare services among this high-risk population. The goal of this study was to examine the association between a farmer’s type of health insurance and their healthcare-seeking behaviors. A brief, in-person, self-administered survey was used to identify the types of health insurance Midwest farmers were using and how this affected what type of healthcare services they utilized, specifically looking at preventive healthcare services. A second survey, administered online, was used to identify pre-existing conditions farmers had and the specific healthcare preventive healthcare services they utilized. The online survey found that type of health insurance was significantly associated with usage of preventive services. Other associations were found in the in-person survey between type of health insurance and stress over health insurance as well as stress over injury on the farm. These results can be used to inform future health and safety programs about the impact of health insurance on farmer’s healthcare-seeking behavior. However, additional research should be done with a larger sample.