An unmanned aerial vehicle (UAV) rendezvous with and transfers a product to a receiving vehicle that is en route to a destination-location. The UAV is dispatched with the product along a flight path that intercepts with a predetermined route that the receiving vehicle is expected to travel along toward the destination-location. Once the UAV is within the vicinity of the receiving vehicle, the UAV approaches the receiving vehicle and utilizes cargo release equipment to transfer the product to the receiving vehicle. In one example, the UAV flies above the receiving vehicle at a synchronized velocity and drops the product through an opening in the roof of the receiving vehicle. In another example, the UAV flies above the receiving vehicle and suspends the product adjacent to a side-window opening of the receiving vehicle to enable an occupant of the receiving vehicle to reach out and retrieve the product.