Older drivers are most at risk of serious and fatal injury in crashes per vehicle mile driven compared with other age groups owing to a combination of cognitive decline and increased fragility. A smartphone coaching application targeting risky driving behaviors (e.g., speeding, hard braking), was iteratively designed to ensure older driver acceptance and usability. A 12-week field operational test examined driving performance of 28 drivers aged 65 to 78 from Kansas and Minnesota using the RoadCoach app and an ABA reversal design. Participants’ baseline driving behaviors were recorded for 3 weeks, followed by a 6-week experimental phase of real-time app coaching, and concluded with a 3-week baseline phase with no feedback provided. Compared with the pretreatment phase, there was a significant reduction in the rates of hard braking and stop sign violations associated with system use. A protection effect was observed through the posttreatment phase. Excessive speeding violations were not significantly different across the phases; however, there were modest declines in the proportion of miles traveled 15 mph above the speed limit in the posttreatment phase compared with the prior two phases. No significant effect was found for excessive acceleration and aggressive turning measures posttreatment, despite an observed increase in both rates during the treatment phase compared with pretreatment. Overall, the results indicate that the RoachCoach app may be an effective intervention to reduce several risky driving behaviors while in use and may result in prolonged behavior changes (i.e., reduced hard braking and stop sign violations) after treatment cessation.