Abstract: A system and method are provided for growing cyber security awareness relating to social engineering and administering anti-social engineering training. The system makes use of artificial intelligence (AI), cyber security strategies and/or gamification principles to help organizations better understand and prepare for potential social engineering security risks. One embodiment of the system includes a reinforcement learning (RL) module, which further includes a trained predictor and an agent that interacts with a target. The RL module receives as input a training dataset that includes information about the target. The trained predictor generates a bait for the target based on the input training dataset; and the agent delivers the generated bait as an attack on the target. The RL module outputs a playbook of the attack, which can be used to update the training dataset and the trained predictor for subsequent iterative attacks, and/or to recommend social engineering countermeasures to the target.