Europe’s aging transportation infrastructure requires optimized maintenance programs. However, data and monitoring systems may not be readily available to support strategic decisions or they may require costly installations in terms of time and labor requirements. In recent years, the possibility of monitoring bridges by indirectly sensing relevant parameters from traveling vehicles has emerged—an approach that would allow for the elimination of the costly installation of sensors and monitoring campaigns. The advantages of cooperative, connected, and automated mobility (CCAM), which is expected to become a reality in Europe towards the end of this decade, should therefore be considered for the future development of iSHM strategies. A critical review of methods and strategies for CCAM, including Intelligent Transportation Systems, is a prerequisite for moving towards the goal of identifying the synergies between CCAM and civil infrastructures, in line with future developments in vehicle automation. This study presents the policy framework of CCAM in Europe and discusses the policy enablers and bottlenecks of using CCAM in the drive-by monitoring of transport infrastructure. It also highlights the current direction of research within the iSHM paradigm towards the identification of technologies and methods that could benefit from the use of connected and automated vehicles (CAVs).