Online retirement planning systems are intended to help individual investors accumulate sufficient savings to support comfortable retirement lifestyles. Although it would seem intuitive that decision makers would choose investment alternatives that provide the highest payoffs over time, individuals tend to construct overly conservative portfolios that yield relatively meager returns. In this study, we explore whether a Web-based decision support system (DSS) that offers advice can enhance decision making by increasing investors' willingness to take calculated risks. Because women tend to be more risk averse when considering financial matters and interact with technologies differently than men, such a DSS might prove especially useful for female investors. A field experiment using retirement plan participants demonstrates that building advice into a DSS helps investors overcome a tendency to hold conservative portfolios. Advice availability and gender interacted such that risk taking is lowest when the DSS fails to provide advice to female decision makers.