Tires in actual service conditions operate on rough roads with a random distribution of obstacles. Rolling resistance, however, is typically measured on smooth surfaces. This paper considers the nature of tire energy loss when impacting obstacles. It is demonstrated by a simple example that translational energy can be “lost,” even in purely elastic impacts, by trapping energy in structural vibrations that cannot return the energy to translation during the restitution phase of the impact. Tire simulations and experiments demonstrate that this dynamic energy loss can be very large in tires if the impact times are short. Impact times indicating the potential for large energy loss are found to be in the range of normal highway speeds.