Technology integration and learning analytics offer insights to improve educational experiences and outcomes. In advancing these efforts, laws and policies govern these environments placing protections, standards, and developmental opportunities for higher education, students, faculty, and even the nation-state. Nonetheless, evidence of educational restrictions, encumbered actions, and archaic approaches pervades the legal literature and case law demonstrating that these laws and policies do not always function well in evolving and emerging technology spaces. To examine these laws and policies of student privacy, the author employs the combination of a critical policy analysis, which derives from critical social research as a means to explore discourse and policy through drawing out the policy contexts, texts, and consequences, and Flood's liberating systems theory, which directs the analysis to a problem-solving approach by examining the policy discourse from a systems-thinking lens. Based on a review of 184 court cases, 74 policies from a diversified representation of US states/territories, and seven developed nations or multi-nation consortia, this examination illuminates how context and text such as the type and setting of the privacy matter (eg, various freedom of information acts, educational records under the Family Educational Rights and Privacy Act, and "General Data Protection Regulation in the European Union") presents opportunities for protections and standardization efforts; however, they also illustrate significant protection gaps, guesswork and insufficiency around the type and degree of data subject consent, and ghosting effects of data subjects' protections. While the extant literature already supports aspects of these findings, it does not account for this holistic view of these three privacy vulnerabilities--especially in light of the principles to which these laws purport to achieve. Moreover, the three identified privacy vulnerabilities suggest overlooked inclusion of two overarching privacy concepts--transparency and equity. This study recommends that key actors in the policy construction realm (ie, university leaders, policymakers, and judges) should engage in analyses, dialogue, and consideration about transparency and equity by considering contemporary privacy problems in the contexts of artificial intelligence, quantum computing, and cybersecurity as a way to improve transparent and equitable policies in these areas rather than exacerbating the privacy dilemmas already in place.