Mission planning and execution comprises high cognitive capabilities such as planning, monitoring and decision making. Such tasks are characterized by a high demand for mental processing resources. If this demand exceeds the available resources, performance can be negatively impacted. We develop Adaptive Associate Systems to counteract these problems. Such associate systems support humans in the execution of cognitive tasks with the aim of increasing mission performance, correcting possible human errors and proactively preventing them. These systems adapt their support to the task situation and the mental state of the pilot. Despite the high functionality of the associate systems, the human pilot remains the ultimate authority. Our intelligent digital assistant makes mission tasks faster, easier and significantly more effective. The software supports mission operators in planning and executing the relevant tasks. It autonomously monitors the mission environment and continuously assesses the operator’s performance. Based on actual outcomes, support strategies are automatically derived.