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The purpose of this mixed-methods study was to analyze the perceived readiness of high school administrators to lead in a digital school (one-to-one classroom) environment. This study utilized the 62-item Digital Instructional Leadership Readiness Instrument (DILRI)© to measure school administrators’ knowledge and confidence to lead in a digital school environment. Based on the data collected, Experience Supervising Others and Colleagues were two factors ranked highest by administrators as influencing their knowledge and confidence. Much research relating to the digital school environment has only focused on the preparation required of teachers; therefore, this study provides school district leaders with relevant information relating to the self-reported readiness of high school administrators to lead in a digital school environment.