This report looks at the digitization and mass connectivity of the transportation sector, notably aviation, roadways, rail and mass transit, and maritime, in a bid to analyze the vulnerabilities of such a transformation. The report will look at how cybersecurity can minimize new digital risks from a technical, policy and regulatory, and market perspective. The first section will look at the digital evolution occurring in the transportation sector, and the new insecure landscape that stakeholders will need to contend with. The second section will analyze the current efforts at cyber preparedness, from policy, technology, and market perspectives. The last section will provide an overview of selected stakeholders pioneering cybersecurity in the space.