A geo-aware transportation verification system and is disclosed. A processor receives a billing request for payment, including an actual geolocation and an actual time and date. The processor compares a service request to a billing request to determine whether a driver is within a field of acceptability. There are at least three types of fields of acceptability for assisting billing verification, where one may be active at a time. The processor automatically adjusts the billing request to match the service request if the driver is within a field of acceptability for geolocation and time. The processor conditionally rejects a billing request if the driver is not within the field of acceptability and provides a user engagement panel on which the user is allowed to submit billing relevant data for further verification. The field of acceptability is updated dynamically based on collected data.