The present application discloses an improved wait time optimization system, and corresponding methods and computer-readable media. According to disclosed embodiments, the wait time optimization system generates a customized wait time period for a provider computing device that has arrived at a pickup location associated with a matched transportation request. Upon the expiration of the customized wait time period, the wait time optimization system selectively enables a cancellation option for the provider computing device that enables a user of the provider computing device to cancel the transportation request, thereby releasing the provider computing device for a new transportation request match.