This disclosure generally relates to automated execution and evaluation of computer network training exercises, such as in a virtual machine environment. An example environment includes a control and monitoring system, an attack system, and a target system. The control and monitoring system initiates a training scenario to cause the attack system to engage in an attack against the target system. The target system then performs an action in response to the attack. Monitor information associated with the attack against the target system is collected by continuously monitoring the training scenario. The attack system is then capable of sending dynamic response data to the target system, wherein the dynamic response data is generated according to the collected monitor information to adapt the training scenario to the action performed by the target system. The control and monitoring system then generates an automated evaluation based upon the collected monitor information.