This chapter investigates how financial literacy and information overload influence the decision to purchase an annuity and how they relate to subsequent confidence and satisfaction. Using a dataset from a large-scale experiment, we find that as financial literacy increases, information overload decreases. In addition, people who experience higher levels of information overload are less confident in their choice and are less satisfied with their decision. We recommend that educators and retirement plan architects consider simplifying the decision environment in addition to improving financial literacy with the goal of increasing investor confidence and satisfaction.