The organizational consequences of information technology (IT) constitutes a core focus in information systems (IS) research. The relationship between organizations and IT has received considerable attention by IS researchers in order to develop knowledge related to how and why organizations and IT are related. While organizational use of IT continues to increase in practice, previous research has shown that the effects of IT at best are difficult to predict. Consequently, the adoption and assimilation of IT in organizational settings must be recognized as complex and challenging processes, which makes the production of knowledge related to such processes important and pressing.   This dissertation identifies, characterizes and explains a paradoxical outcome of the adoption and assimilation of an enterprise content management (ECM) system in a context of organizational information management. The outcome, labeled the duplicate systems paradox, is constituted by a situation in which an organization continuously allows multiple, overlapping, partially competing and largely incompatible information systems to persist and continue to evolve over time, despite continued awareness of the adverse consequences on organizational information management capabilities. A qualitative case study approach was used as the primary means for data collection. The case study was conducted in the administrative divisions of HealthOrg, a large organization in the medical- and health care sector. To this end, the main objective of this dissertation is to investigate how this paradox was formed, and furthermore, how and why it was able to persist. In order to do this, dialectical theory is combined with contextualism and theory on organizational information processing to form a comprehensive theoretical perspective used to inform the analytical efforts.   By using a dialectical approach, the analysis presents empirical evidence of the existence and composition of three overarching contradictions found to affect the formation and persistence of the duplicate systems paradox. More specifically, the resulting explanatory model demonstrates how three pairs of opposites, control versus support at the requirements level, options versus practices at the solutions level, and top-down versus bottom-up approaches at the transformations level, along with contextual tensions, were essential components in the formation and persistence of the paradox. Thus, the duplicate systems paradox could form and continue to evolve due to contradictory forces present at, and interconnected between, different vertical and horizontal levels within the organization. Through the identification and explanation of the duplicate systems paradox, this study provides a detailed example of how, and why, unintended consequences of IT in organizations may emerge and continue over time.   In terms of implications for research and practice, the findings of this dissertation point to six important observations. First, this research suggests that understanding and characterizing the context in which IT is to be implemented is crucial and challenging. Thus, organizations should pay careful attention to the practical side of context, rather than to the somewhat theoretical boundaries of organizations. It is suggested that the concepts of ‘inner’ and ‘outer’ context may be useful in analyzing and understanding context. Second, this research suggests that organizations should attempt to identify potentially conflicting requirements, and devise clear strategies to decide how to prioritize between such requirements as the identification and explication of requirements present at different levels in the organization may reveal problems that need to be considered when choosing information system (IS). Third, organizations need to pay careful attention to what the adoption of a new IS means in terms of adaptation and/or realignment, and to what extent organizational activities, technological functionalities, or both, should be adapted. Organizations should furthermore be aware that the adoption of systems that can also be used as development platforms may cause a cascade of effects and dependencies that are difficult to manage. Fourth, the findings of this research suggest that organizations faced with the challenge of adopting complex IT solutions need to take into account their previous strategies and planned new ones in order to devise a comprehensive strategic approach since the coexistence of radically different strategies may cause uncertainty and inertia within the overall assimilation process. Fifth, this research indicates that IT management and information management (IM) are highly interrelated activities, but are not mutually exclusive. Thus, organizations adopting technologies that are specifically focused on information management may benefit from developing distinct areas of responsibility and clear communication channels between the involved organizational units. Furthermore, these findings suggest that future research should pay careful attention to, and specifically investigate, the exact nature of the relationship between information management and IT management. Finally, this research demonstrates how a dialectical approach may be used to adequately investigate organizational information management, specifically in relation to the adoption and assimilation of IT.