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This study emerges from my lived experience as a Black teacher navigating the promises and contradictions of digital technology in English classrooms. I watch youth compose under the gaze of plagiarism detectors, grammar checkers, and predictive technologies that often misread their brilliance as error, their voices as violation. While framed as neutral or efficient, these tools carry embedded assumptions about language, identity, and intelligence. This inquiry turns to the archival work of Black educators who documented their pedagogy in the face of systemic neglect. Their records offer a method of remembering, resisting, and reimagining. Grounded in teacher inquiry, poetic reflection, and digital literacies, this study uses critical historical analysis and autoethnography to explore how past and present pedagogies converge.