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Recently, there has been an increase in technology-mediated personalized learning, which intimates changes in school structure and teachers’ instructional practices towards improved student outcomes. In this context, school models that leverage technology to personalize instruction have proliferated, as has student enrollment in, and funding of such school models. However, even the best laid plans are subject to disruptions, challenges, and contradictions in design and practice, particularly in the dynamic context of a school. Using cultural historical activity theory as a frame, the author identifies how administrators and teachers enact program goals aimed at personalized learning in their practices, the challenges they face in doing so, and the strategies and practices they develop in response to these challenges.