Employees continue to be the weak link in organizational security management and efforts to im-prove the security of employee behaviors have not been as effective as hoped. Researchers contend that security-related decision making is primarily based on risk perception. There is also a belief that, if changed, this could improve security-related compliance. The extant research has primarily focused on applying theories that assume rational decision making e.g. protection motivation and deterrence theories. This work presumes we can influence employees towards compliance with in-formation security policies and by means of fear appeals and threatened sanctions. However, it is now becoming clear that security-related decision making is complex and nuanced, not a simple carrot- and stick-related situation. Dispositional and situational factors interact and interplay to influence security decisions. In this paper, we present a model that positions psychological dispo-sition of individuals in terms of risk tolerance vs. risk aversion and proposes research to explore how this factor influences security behaviors. We propose a model that acknowledges the impact of employees’ individual dispositional risk propensity as well as their situational risk perceptions on security-related decisions. It is crucial to understand this decision-making phenomenon as a foundation for designing effective interventions to reduce such risk taking. We conclude by offer-ing suggestions for further research.