The first chapter examines consumer choices of health insurance contracts. An important innovation in health insurance design is a high-deductible health plan paired with a health savings account (HSA). These contracts aim to control costs by linking insurance coverage with tax incentives for saving, but their rules are highly complex. How consumers perceive the features of these contracts may dampen any cost reduction and produce unintended welfare effects by distorting plan choices. Using a novel administrative dataset linking health insurance choices, medical claims, and saving in HSAs and 401(k)s from a large U.S. health insurer, I develop and estimate a model that integrates HSA saving with deductible choices. I estimate over two-third...