In the modern era, the advances in information technology have been dramatically shaping the ways people live as well as the ways organizations manage their businesses in their professional business domains. Implementing various kinds of information systems, such as Decision Support Systems, has been recognized as one of the most crucial tasks for organizations in order to continue to be competitive or even to survive. Although considerable effort has been devoted to improving the performance of information system implementations, organizations are still constantly suffering from the failures of information system implementations. In this study an extensive framework that depicts the context of information system implementation is developed. A system dynamics approach is used to investigate the dynamic nature of information system implementations. By using the proposed system dynamics model, we contend, executives and information system professionals of organizations can gain comprehensive insights into organizational behaviors and substantial policy-making implications regarding information system implementations.