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In this paper, we use positioning theory to theorize how to prepare teachers to critically engage with AI. Unlike approaches that emphasize AI competencies and literacies, we use “technoskepticism” as a position that teachers can (and ought to) take with respect to AI. We conceptualize what a technoskeptical position toward AI means and how it differs from related notions of AI Literacy. To further elaborate upon and illustrate those conceptual foundations and discuss how technoskepticism might be developed among teachers, we present several vignettes from our ongoing work with current and future teachers. We use those vignettes to clarify our theoretical propositions and provide suggestions for teacher education.