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In recent years, we have seen an expansion of scholarship that adopts critical perspectives on education technologies. Yet while critical views are arguably more important than ever, few studies have examined how educators develop those perspectives. The goal of this study is to inform our future educational efforts by examining the views and experiences of educators who have successfully developed critical perspectives of technology. Using educators’ written narratives as well as interviews, we explore the forms that their critical perspectives take and the trajectories that led them to those views. Drawing from Freire’s theory of Critical Consciousness, we describe formative experiences that spurred critical reflection and the distinct trajectories our participants followed to their specific critical orientations.