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The purpose of this paper is twofold: 1) to present challenges faced by faculty supervising online educational leadership doctoral dissertations, and 2) to offer strategies that could assist doctoral faculty, particularly those new to the process. In doing so, we intertwine the literature findings with our supervising experiences that encompasses our involvement in close to 100 dissertations. Although we cannot make a claim that these experiences are universal, we believe that they resonate across the doctoral programs offering a doctoral degree for educational professionals.