Abstract : The focus of this research is to study the characteristics of flexibility in order to help building more flexible IS. The objective is to achieve flexibility in the IS in order to adapt them swiftly for facing changes, and be able to adjust for new strategies. The main questioned posed is: How can IS flexibility be achieved?. This constitutes the research question. This research extends previous studies related to flexibility by focusing on the various dimensions of Information Systems. To cover all the aspects of an IS the problem of enabling an IS with flexibility will be approached, in this research, by analyzing the relevant elements in an Information System. This research will try to identify what IS flexibility is in the people, process, IT, and data dimensions; and how IS flexibility can be achieved. The conclusion that can be drawn is that the flexibility enablers needed for an Information System are contingent upon its unique characteristics. The findings of both case studies show that the elements that sustain flexibility are not the same for every IS; they depend on certain characteristics of the specific IS. The fact that the elements or enablers needed to sustain flexibility are different can be explained by the polymorphic property of flexibility: for an IS, flexibility displays the same polymorphism characteristic found in strategic flexibility. The answer to the research question of how IS flexibility can be achieved, lies in the flexibility enablers needed for a specific IS. From a practical point of view this means that the managers involved in flexibility decisions or initiatives should understand that there are flexibility enablers in the resources of a firm that can be deployed or acquire. Then, they should become familiar and understand them. But in order to really enable a particular IS with the correct set of flexibility enablers (or the correct form of flexibility needed) it is very important that these enablers be selected according to the unique characteristics of the IS in hand. The conceptual IS flexibility framework developed in this research and the findings presented as a result of two case studies (of two different flexible Information systems tightly linked to changing strategies) conducted, constitutes a valuable guide for managers to deploy flexible IS to rapidly adapt them when faced to changes needed for strategies implementation in a continuous manner.