The successful implementation of Enterprise Applications (EAs) hinges on a process of organizational sensemaking that enables the focal organization to gain an understanding of the unique contextual issues within and surrounding the organization, and continuously monitor and re-interpret these issues so that the approach to EA implementation can be modified or re-aligned accordingly. Yet, little attention has been paid to the examination of this process of organizational sensemaking. Using a case study of the EA implementation journey of Shanghai Tobacco Corporation, the purpose of this paper is to examine the nature of organizational sensemaking in EA implementation in the context of a dynamic environment, and its implications for the nature and outcome of EA implementation. With its findings, this study contributes to the theoretical discourse on EA implementation by constructing a model of the sensemaking process, and provides indications to practice on the effective implementation of EAs.