Information technology has become not just an essential element of the telecommunication infrastructure but is also used more and more in relation to transportation systems and transportation infrastructure. While on the one hand the integration of information technology enables the development of highly sophisticated traffic control systems and new forms of interaction, it also enables new methods of attacks. This chapter gives an overview about attacks that took place and analyses the system of vulnerabilities in transportation infrastructure with regard to network-based attacks. In addition it highlights some of the challenges that go along with the prevention and investigation of such attacks.