This study designs and tests a personalization system that considers the interactive effects of user personality and suggestive guidance in a decision-making situation involving risk. The system suggests a specific course of action that varies in congruency with the users' natural risk taking tendencies. Findings suggest that when the system suggests a risk-seeking course of action, both high and low propensity users assume greater risks, with high risk propensity users taking significantly greater risks than low risk propensity users. Regardless of risk propensity, however, all users make conservative decisions when the system suggests a risk-averse course of action. Providing mismatched offerings to risk-seeking users nullifies the effects of risk propensity. The modality of suggestive guidance embedded in a personalization system influences the decisions of different personality types in unique ways. Theoretical and practical implications are discussed.