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The relevance of this study is due to the fact that medical institutions are now forced to quickly adapt to large-scale digital transformation. This process has a profound impact on the healthcare management system and poses new challenges for managers. The article aims to identify the management challenges that medical institution managers face when implementing digital technologies, as well as to identify approaches that can help effectively overcome these difficulties. The methodological basis of the study includes systemic, structural-functional, comparative and analytical methods, which made it possible to comprehensively analyze the organizational, personnel and technological aspects of digitalization. In the course of the work, it was found that digital transformation actually forms a new management paradigm for managers, in which they have to simultaneously think strategically, understand technologies and work with personnel development. The study made it possible to identify key barriers to digitalization: insufficient digital literacy of employees, limited resources and the complexity of integrating new information solutions into already established processes. The level of readiness of medical institutions for digital changes turned out to be heterogeneous and largely depends on the type of institution and its resource capacity. Special attention is paid to the analysis of management models that contribute to successful digital transformation, in particular, change management models and the practice of forming interdisciplinary teams. The practical value of the study lies in the possibility of using its conclusions to form strategies for the digital development of medical institutions, improve management decisions, train managers to introduce innovations and increase the efficiency of organizational processes. The results obtained allow us to consider digitalization not only as a technological process, but as a complex management transformation.