A driving management system includes an authentication server, and a vehicle capable of switching between a manual driving mode and an automatic driving mode. The vehicle includes multiple electronic control processors connected to a network inside the vehicle, a first processor that detects switching between the manual driving mode and the automatic driving mode, based on messages issued by one or more electronic control processors of the multiple electronic control processors, and the first processor generates first transaction data including information indicating the detected switching, and a first identifier indicating the vehicle, and transmitting the first transaction data to the authentication server. The authentication server includes a second processor that judges the validity of transaction data including the first transaction data obtained from the vehicle, and the second processor records the transaction data, of which the validity has been verified by the second processor, in a storage device.