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This mixed-methods study examines how 15 undergraduate students at a Maryland-based HBCU engaged in “critical futuring” through AI-assisted academic writing. Positioned at the intersection of Black educational histories and emerging technologies, students utilized generative AI tools, such as ChatGPT and DALL·E, to create multimodal counter-narratives that envision liberated educational futures. Guided by culturally sustaining pedagogy and speculative design, students responded to community-rooted prompts that centered justice, memory, and imagination. Writing quality was assessed across agency, coherence, criticality, and multimodal integration. Results show that intentional AI scaffolding elevated student voice, affirmed lived experiences, and expanded civic imagination. We propose an anti-deficit AI pedagogy framework that centers on Black literacies and reimagines AI as a tool for cultural resilience and future-making.