This paper analyzes the role that demographics, health services utilization, and knowledge play in determining the choice of insurance plan. Using data from a 2014 National Opinion Research Center (NORC) report and by estimating a probit model, I examine the effect of the three variable categories on the probability of selecting a High Deductible Health Plan (HDHP). While many of the results align with the existing literature, I contribute to prior insurance studies by finding that confusion over health services and plan benefits is the largest driver in HDHP choice, as it increases the probability that an individual enrolls in an HDHP by over 15 percentage points. This result provides evidence to policymakers that insurance education should be more widely available to ensure that individuals are choosing a plan that best fits their needs.