A system for monitoring operator and motor vehicle behavior, including at least one mobile device application software resident on the mobile device, wherein the application software is operative to gather and record information relevant to both the behavior of a motor vehicle and the behavior of an operator of the motor vehicle, and wherein the application software is activated or deactivated based on certain predetermined trigger events and at least one information processor in communication with and/or resident on the mobile device, wherein the information processor is operative to process and characterize the information gathered by the application software and communicate the processed and characterized information to a user of the system.