A computerized method comprising, on a mobile computing device, processing a vehicle integration request made by one or more of (i) the mobile computing device and (ii) a transportation vehicle. The mobile computing device computes a risk assessment value that quantifies a security risk to the transportation vehicle as a result of connecting the mobile computing device to the transportation vehicle, where the computing is based on one or more of a hardware and a software of the mobile computing device. The mobile computing device transmits the risk assessment value to a vehicle computer integrated in the transportation vehicle. The mobile computing device completes a digital data connection with the vehicle computer when the risk assessment value complies with a vehicle access security policy of the vehicle computer.