Despite recent calls for research that examines person-situation interactionist models of ethical workplace behavior, little is known about how managers’ personal characteristics and contextual factors combine and interact to influence unethical managerial behavior (UMB) in organizations. Adopting a multiple-set perspective, we examine the individual, situational, organizational, and institutional factors that are associated with UMB as well as two key moderating influences, moral intensity and situational strength. The findings of a survey of 52 real-world cases on UMB reveal that several individual and organizational variables are significant influences, whereas aspects of the ethical issue at hand and the wider institutional context do not seem to be associated with unethical conduct. As predicted, the case survey findings indicate that moral intensity and situational strength moderate the relationships between individual characteristics and managers’ propensity to engage in UMB.