AbstractEducational institutions face an emerging structural problem in AI adoption. Major technology vendors have structured their agreements to cap liability at nominal sums, while insurers are simultaneously excluding AI-related claims from standard coverage or conditioning specialty coverage on governance documentation most schools cannot produce. The result is an expanding zone of institutional exposure that neither vendors nor insurers will cover.This memorandum documents the two-sided liability squeeze, examines the information asymmetry that sustains it, and argues that governance documentation provides leverage to change the dynamic. The analysis draws on vendor contract terms from Microsoft and Google, insurance market developments including ISO exclusion endorsements and specialty carrier programs, and emerging regulatory requirements across multiple jurisdictions.Key findings include: vendor liability caps of $5 to $10 for free-tier services create exposure gaps of potentially millions of dollars; commercial AI exclusions are proliferating while education-specific exclusions have not yet materialized, creating a finite window for governance development; and governance documentation serves not merely as compliance artifact but as negotiating leverage in vendor contracts, insurance renewals, and board accountability.The memorandum concludes that the structural conditions for the liability squeeze are in force, the forcing functions are activating, and institutions that build governance infrastructure proactively will be positioned to negotiate from strength rather than scramble under pressure.