The Insider Threat Study, conducted by the U.S. Secret Service and Carnegie Mellon University’s Software Engineering Institute CERT Program, analyzed insider cyber crimes across U.S. critical infrastructure sectors. The study indicates that management decisions related to organizational and employee performance sometimes yield unintended consequences magnifying risk of insider attack. Lack of tools for understanding insider threat, analyzing risk mitigation alternatives, and communicating results exacerbates the problem. The goal of Carnegie Mellon University’s CyLab-funded MERIT (Management and Education of the Risk of Insider Threat) project is to develop such tools. MERIT uses system dynamics to model and analyze insider threats and produce interactive learning environments. These tools can be used by policy makers, security officers, information technology, human resources, and management to understand the problem and assess risk from insiders based on simulations of policies, cultural, technical, and procedural factors. This paper describes the MERIT insider threat model and simulation results.