This paper introduces a novel use of timeline-based planning as the core element within a dynamic training environment designed for crisis managers. Training for crisis decision makers at the strategic level poses a number of challenges that range from the necessity to foster creative decision making to the need for the creation of engaging and realistic scenarios in support of experiential learning. This article describes our efforts to build an end-to-end system, called the PANDORA BOX, that helps the trainer to populate and deliver a continuous 4-5 hours training session encompassing exercises that encourage a group of decision makers to achieve joint decisions. Specifically the emphasis is given to (a) the timeline-based representation as the core component for creating training sessions and unifying different concepts of the PANDORA domain; (b) the combination of planning and execution functionalities required to maintain and dynamically adapt a "lesson plan" on the basis of both trainee-trainer interaction and individual behaviors and performance; (c) the importance of keeping the trainer in close control of the activity loop.
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