A mobile device may include at least one sensor that detects a characteristic of the mobile device selected from distance traveled, location, time, and g-force dynamics; a processor; and a tangible non-transitory computer readable storage medium containing instructions that, when executed on by the processor, are programmed to automatically detect that a wireless connection has been established between the mobile device and a vehicle, and in response to detecting the wireless connection between the mobile device and the vehicle, automatically start collecting vehicle operation data via the at least one sensor. The mobile device may automatically stop collecting the vehicle operation data in response to the vehicle being turned off.