The disclosed computer-implemented method may include matching transportation requests. By collecting and batching match requests over an extended period, a dynamic transportation matching system may identify more efficient matches (e.g., may match transportation requests with greater overlaps). In addition, by dynamically setting and/or extending the upper bound of time that a transportation request may remain batched with other transportation requests, the dynamic transportation matching system may account for contextual information thereby situationally improving matching efficiencies made possible with higher upper bounds while avoiding requestor dissatisfaction, lost conversions, or other inefficiencies that may result from upper bounds that are too high. Furthermore, by providing a notification interface for a transportation requestor device that notifies the requestor when to be ready, a transportation matching application may provide a positive requestor experience while allowing for longer match windows. Various other methods, systems, and computer-readable media are also disclosed.