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Situational simulations are dynamic, interactive, context-sensitive, adaptive environments. They further construction research by providing an interactive simulation platform that can be used to explore what-if construction scenarios and to estimate risks and contingencies. This paper extends current research to study the evolution of dynamic uncertainty in construction management projects using situational simulations as experimental testbeds. An experimental framework is proposed to explore alternative outcomes of a particular decision strategy, and also investigate the impact of alternative decision strategies under similar project scenarios. A set of preliminary experiments were conducted to illustrate the proposed framework. The significance of this research is in enhancing and informing the deliberative process during the planning and pre-planning stages of a construction project and supporting the preparation of contingency plans of action in anticipation of varying levels of project risk and uncertainty.