A pilot program in Austin, Texas, tested the practicality of integration of a real-time ridesharing application with a toll operator to process toll discounts for carpools. The toll discounts appeared on monthly toll transaction statements. The program lasted for almost a year on the 183A Toll Road and the US-290 Manor Expressway. Travelers used a smartphone application to track, record, and submit their trips for discounts. Two-person carpools that used the application received a 50% discount, and carpools of three or more people could travel toll free. The program was a partnership between the Central Texas Regional Mobility Authority, the local toll system operator, and a private ridesharing vendor. Back-office processes matched trip data from the smartphone application to transactions recorded by the toll systems. A total of 95 unique drivers were provided toll rebates for 2,213 trips during the 10.5-month period of the pilot program. During the pilot program, rebates were provided for most trips by two-person carpools. Individual driver behavior varied considerably. A select few drivers had a high number of carpool trips, whereas others took a sporadic trip or infrequent trips. Drivers took a median of seven trips during the pilot program. Future ridesharing programs should consider showing higher-dollar-value rebates that represent annual savings to incentivize ridesharing behavior. Timely feedback to users was found to be an important goal for success. In addition, program sponsors should provide positive customer service and engage users when problems that are not under their direct purview exist.