Background: In a health insurance system based on managed competition, such as in the Netherlands, it is important that all citizens can make well-informed decisions on which policy fits their needs and preferences best. However, partly due to the large variety of health insurance policies, there are indications that a significant group of citizens do not make rational decisions when choosing a policy. Objective: This study aimed to provide more insight into (1) how important it is for citizens in the Netherlands to choose a health insurance policy and (2) how easy it is for them to comprehend the information they receive. Methods: Data were collected by sending a survey to members of the Nivel Dutch Health Care Consumer Panel in February 2017. The response rate was 44% (N = 659). Key Results: Our results indicate that citizens in the Netherlands acknowledge the importance of choosing a health insurance policy, but they also point out that it is difficult to comprehend health insurance information. Conclusion: Our findings suggest that a section of the citizens do not have the appropriate skills to decide which insurance policy best fits their needs and preferences. Having better insight into their level of health insurance literacy is an important step in the process of evaluating the extent to which citizens can fulfill their role in the health insurance system. Our results suggest that it is important to better tailor information on health insurances to the specific needs and skills of the individual. By doing this, citizens will be better supported in making well-informed decisions regarding health insurance policies, which should have a positive effect on the functioning of the Dutch health insurance system. [HLRP: Health Literacy Research and Practice. 2021;5(4):e287–e294.] Plain Language Summary: The number of health insurance policy options to choose from is extensive in the Netherlands. This study explored to what extent citizens in the Netherlands find it important to choose a health insurance policy, ...