The technologies that support online learning are continuously evolving, providing instructors and students with a continuous stream of new tools, features, and functionalities for existing tools. During an online course, instructors and students generate and share a tremendous amount of data using these tools. These data are often created in contexts where privacy concerns and safeguards are similarly evolving and uncertain. This article discusses online privacy concerns and emergent solutions in online learning contexts where technology transience is present. It focuses on issues such as legal rights, issues raised by emerging educational technologies, and manners by which institutions, instructors, and learners might mitigate both security risks and the level of personal discomfort that accompany these risks.