Abstract: An apparatus and method of using gamification and human behavioral analysis to quantify cyber security risks for a corporate or individual entity, in which the apparatus, or systems, can include a comprehensive real-time cyber security risk assessment, monitoring and remediation service, particularly through quantifying the qualitative aspects of individual user behavior and entity-level cyber security activities, and incentivizing and enabling effective cyber security outcomes through gamification. These capabilities will also enable the apparatus, or system, to deliver real-time cyber insurance to users on a risk-effective basis.