In two separate legal developments with direct implications for higher education technology and student privacy, Meta and Anthropic faced renewed scrutiny over how AI systems handle sensitive data and cybersecurity risk. A lawsuit alleges Meta’s Ray-Ban smart glasses routed user footage to human workers overseas for AI training, including footage depicting intimate content and potentially sensitive financial documents. Separately, Anthropic disclosed a security lapse after details of an unreleased model and internal materials were inadvertently exposed via an unsecured content management system. Anthropic acknowledged human error in configuration and moved quickly to restrict public access after reporting. Universities are increasingly buying or deploying AI tools and digital platforms in classroom and advising contexts; these cases highlight the compliance risks around data stewardship, AI transparency, and information security—areas that accreditation and federal IT expectations increasingly touch.