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This chapter critically examines whether it may be possible to create an AI-based authentic leader, questioning the inherent contradiction between artificial and authentic. The authors pose central research questions: Does the application of AI – even just as a powerful resource – challenge the tenets of authentic leadership? What are the possibilities and limitations of the concept of authenticity in AI-based management systems? Moreover, with the help of three vignettes illustrating practical applications of AI-based systems in leadership and management tasks, the authors illustrate how technology may be used to either control or empower workers and leaders. The authors call for research to assess whether the search for authenticity in AI-based leadership could lead anywhere, warning that it could entrap us in unresolvable existential and conceptual ambiguity, ultimately diverting our focus from the essence of leadership altogether.