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This design-based research examines My Partner in Equity (MPIE), a custom GPT tool developed to scaffold justice-centered leadership through dialogic reflection. Over 21 months of iterative development with authentic educator usage, systematic documentation captured 150+ interactions across scenarios through dual-author reflexive inquiry. Drawing on Vygotsky’s sociocultural theory of cognitive development, the research explores how MPIE functions as a provisional “more knowledgeable other” within users’ Zones of Proximal Development. Through thematic analysis and iterative design evaluation, findings reveal the tool's capacity to support cognitive growth through AI-mediated scaffolding while surfacing ethical tensions around emotional authenticity, model opacity, and platform dependence. While AI cannot substitute for critical consciousness, intentionally designed tools can serve as reflective infrastructure for liberation-centered learning.