The ‘rideshare challenge’ is as much about human preferences as it is about the need for improved technology. As such, future initiatives should place as much emphasis on participant engagement efforts, such personal travel planning and the provision of rideshare incentives, as it does on advanced technologies. Preliminary research efforts suggest that the provision of personalized travel information can influence travel behavior and reduce SOV trips by 10% or more. Incentives have long been a successful mechanism to encourage ridesharing and are likely to remain important for the foreseeable future. Personal travel planning and incentives tend to be the most expensive components of a rideshare initiative, however designers should resist the urge to eliminate these features, as they are as likely (if not more likely) to increase the overall level of rideshare participation as technology enhancements alone.