This chapter interrogates the enduring paradox between technological promises of democratized knowledge and the persistent reality of centralization, exclusion, and commercial capture. Using the AGUCK framework (Access, Governance/Agency, Use/Auditability, Contestability, Knowledge Concentration) to analyze artificial intelligence as a contemporary stress test—but with arguments that transcend any single technological wave—we expose why true knowledge democratization remains structurally elusive. Through empirical tracking of democratization trajectories from 2020 to 2025, we demonstrate that while access metrics improve superficially, deeper measures of agency and contestability deteriorate systematically. We analyze why this technological disruption is structurally different from previous waves and present evidence-based frameworks for society-driven governance. The analysis reveals that apparent democratization (consumption access) diverges sharply from real democratization (agency + contestability), with governance design, funding models, and power structures—not technological capability—determining outcomes.