Disclosed is a method for identifying, in real time, a transportation arrangement between a requestor and a provider that could benefit from a re-matching of the requestor with another provider. A system may match a provider with a requestor to complete a request for transportation from the requestor. The system may monitor a progress of the provider to a pickup location as specified in the request. Based on the monitored progress, the system may determine if the provider is making sufficient progress towards the pickup location. In some examples, the system may determine that the matching of the provider with the requestor is eligible for cancellation because the provider is not making sufficient progress towards the pickup location. The system may cancel the matching and then match another provider with the requestor to continue to make progress towards completing the transportation request.