Continuing developments in the fields of transportation technology and privacy law present an abundance of opportunities for conflict. Without knowledge of the legal framework that applies to emerging technology, Intelligent Transportation System (ITS) developers set themselves up for frustration as ideas that appear flawless in an engineering office may become controversial when they reach the implementation stage. From the legal perspective, advocates of comprehensive privacy law struggle to update existing law at a pace that keeps up with innovative advancements in technology. This paper reviews several cases where implementation of transportation technologies has raised civil liberties arguments, examining them from legal and political perspectives. The understanding of privacy both as a political concept and a legal protection provides the foundation for future ITS progress, allowing new technologies to be developed in ways that can withstand these types of challenges or avoid them altogether.