The present application discloses an improved transportation matching system, and corresponding methods and computer-readable media. According to the disclosed embodiments, the transportation matching system identifies low engagement transportation providers by analyzing information associated with the transportation providers to generate engagement levels. Furthermore, the system identifies an optimal match between a low engagement transportation provider (regardless of whether the transportation provider is online or offline) and a scheduled transportation request by utilizing attributes associated with a scheduled transportation request and attributes associated with transportation providers to generate rankings for the transportation providers. Additionally, the system provides the scheduled transportation request exclusively to a selected transportation provider based on the generated rankings.