The paper presents a theory of uncertainty and its modeling, emphasizing the situational property of uncertainty in problem solving process of complex systems. The design and implementation of tools and enablers based on the model related algorithms are aimed to facilitating effective decision making and to optimize efficiency through alleviation of information uncertainty, such as fuzziness of observations and inconsistent understanding of terms. These tools and enablers are equipped in the specific decision support system WDSS to support the participants of a SBA task, as decision makers to make decisions in the SBA decision making processes. Therefore, Simulation Based Acquisition and the SBA desired Web-based decision support system WDSS have to be systematically introduced. To satisfy the technical challenges (1) providing decision traceability, (2) ensuring consistent analysis, and (3) supporting information access, understanding and management by both humans and software agents of the SBA desired DSS, it's functional, behavioral and consequently the technological characteristics responding to these challenges are necessarily explained. The fuzzy technological framework is embedded in the problem solving mechanism of decision making processes, and behaves as a comprehensive and, adaptive knowledge transformation paradigm aimed to form internal consistency.