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Business-managed IT and Shadow IT describe the autonomous deployment/management of IT instances by business units. For the former, this happens in alignment with the IT organization of the enterprise, for the latter, without alignment. We analyze why and how Business-managed IT and Shadow IT transform knowledge sharing with two case studies drawing on the theoretical lens of the knowledge-based view. Several motivators lead to the autonomous implementation of knowledge management systems (KMSs), for example, shortcomings of existing systems. The implemented KMSs have multiple benefits for knowledge sharing, such as a reduction of knowledge sharing barriers. However, we notice that the Shadow IT KMS leads to challenges for cross-unit knowledge sharing due to the covert nature of Shadow IT. Based on the findings of our case studies, we develop a mid-range theory to explain the transformation of knowledge sharing in enterprises supported by Business-managed IT and Shadow IT.