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The abundance of dynamic mission monitoring data and the elusive nature, of knowledge necessary for effective organizational adaptation necessitate knowledge management strategies involving knowledge codification and rapid information transfer. Decision support system (DSS) based on the third-generation distributed dynamic decision-making (DDD-III) simulator is a suitable test-bed to investigate these processes. The DSS utilizes an integrated view of contingency notions that incorporate three relevant components affecting organizational performance: (1) environment, (2) organizational structure, and (3) strategy (process). The contributions of this paper are two-fold. First, we seek to investigate the advantage of utilizing a DSS as a means to augment the organizational cognitive capacity, and to facilitate the processes of adaptation. Second, we seek to extend the contingency model to include a quantitative framework that relates organizational performance with congruence conditions. Based on these, we investigate necessary organizational changes to remedy the incongruence conditions to recover organizational fit.