This study empirically estimated the role played by attitudes toward risk in insurance decision-making. Four hundred forty-five participants underwent the Iowa Gambling Task (IGT) coupled with skin conductance recording and demographic/socio-economic questionnaires. The multiple regression model showed a higher probability of holding health insurance for people who are more risk seeking (bad performance at the IGT) but are adaptively able to feel the risk (normal anticipatory skin conductance responses to disadvantageous decks). The role played by traditional socio-economic explanatory variables (age and work status) was confirmed. Results are discussed in light of the need for interdisciplinary research.