A system for generating a cyber-attack to penetrate a network. The system includes an identification module configured to identify at least one vulnerability of the network by examining at least one of a node of the network, data transmission within the network, or data received from a cyber defense mechanism; a generation module configured to generate a cyber-attack based on the at least one vulnerability of the network, and a goal to be achieved by the cyber-attack. The system includes a penetration module configured to penetrate the network with the cyber-attack and determine an effectiveness rating of the penetration; and a feedback module configured to provide a feedback to the identification module based on at least the effectiveness rating of the penetration.