While people claim that they want to control access to their personal information, the ease and convenience of online applications put their personal data at risk with a keystroke. The sale of personal information and subsequent behavioral tracking happens in invisible ways not fully understood by most end users. Younger online participants, such as students, who are accustomed to sharing information online, may not be aware of digital footprints or digital permanence. Similarly, student users may be unaware of risks to participating online at school or how to manage these risks. Selected countries and international organizations have offered policy solutions that, when analyzed expose policy gaps and vulnerabilities. The authors unpack the issue of digital privacy for schools with a three level approach to the research. First, they report on what is known about the identified risks to students of vulnerable ages who access online programs in schools and reported levels of awareness of these risks. Next, the authors disaggregate privacy issues related to the paradox or tradeoff of trust versus convenience in click-through agreements with providers. Third, the authors analyze national and international policy approaches designed to protect the digital privacy of students and offer recommendations for moving forward.