Transportation is a complex infrastructural sector that is facing significant cyberattacks in the last few years. With the development of organised cybercrime groups and the advent and implementation of new technologies such as the Internet of Things and Artificial Intelligence, the threat landscape is bound to become more sophisticated and diverse in the coming years. This talk will review past incidents and the current cyber-risks for the sector and will identify lessons learned or that should have been learned from past experiences and the challenges that might arise in the future considering the developing threat-landscape.