Health Reimbursement Arrangements (HRAs) and Health Savings Account (HSA) eligible High Deductible Health Plans (HDHPs) emerged as a new health care insurance models referred to as Consumer Directed Health Plans (CDHPs) in the early 2000s. The purpose of this study is to examine the association between enrollees’ prior financial experiences as they relate to health care access and use with plan choice when a Managed Care Preferred Provider Organization (PPO), HRA, and HSA eligible HDHP are offered concurrently in an ESI program. It is important to examine new health insurance structures, such as CDHPs, to better understand their impact on enrollees’ choice of health plan. Factors that determine enrollees’ plan choice can influence the distribution of socio-economic, health risk, and behavioral characteristics across plans. These factors in turn can affect the financial costs, risk pools, and long-term solvency of such plans. The theoretical framework used in this study is adapted from Andersen’s behavioral model and suggests economic enabling resources, self-perceived need for health care, predisposing characteristics, and plan cost characteristics are significant factors in Managed Care verses CDHP choice. First, descriptive statistics are used to describe the enrollee population relative to available plans. Then, multivariate analyses are used to examine hypotheses developed to examine employee earnings, prior Flexible Spending Account (FSA) participation, prior total cost sharing and Relative Risk Scores (RRS). Findings suggest first that CDHPs benefit from favorable selection, however the type of CDHP is a critical factor in the dynamics of plan choice. It is important not to categorize different forms of HRAs and HSA eligible HDHPs generically as CDHPs, but treat them as unique based upon their cost and administrative characteristics. Second, enrollees appear to select a plan that minimizes their future financial exposure based on past ESI experiences. Finally, CDHP choice and enrollee earnings may not have a simple linear relationship as suggested by prior research. Plan choice may depend largely on the dynamics between factors of economic resources, perceived need, and plan cost characteristics.