A generative adversarial network and a reinforcement learning system are combined to generate phishing emails with adaptive complexity. A plurality of phishing emails are obtained from a trained generative adversarial neural network, including a generator neural network and a discriminator neural network. A subset of phishing emails is selected, from the plurality of phishing emails, using a reinforcement learning system trained on user-specific behavior. One or more of the subset of phishing emails are sent to a user email account associated with a particular user. The reinforcement learning system is then adjusted based on user action feedback to the one or more of the subset of phishing emails.