In an era where cybersecurity threats are increasing, a strong authentication system is one of the foundations of digital security. This paper presents a computational analysis of the dynamic collaboration of a system-level authentication model, a human decision-making process, and an AI Coach as supervisor and performance enhancer. To simulate this, an adaptive dynamical system model has been developed that shows how risks related to contextual variables influence an admin’s stress level and, consequently, its risk assessment of the situation. The model was designed as an adaptive network model and uses adaptive mechanisms and an AI coach that detects misjudgments by the admin and helps to correct during the decision-making process. A What-If analysis was conducted to investigate the impact of important variables such as stress sensitivity and persistence levels on risk assessment accuracy. Results show that the AI Coach plays a critical role and is an important addition to the model.