A computer, for planning moves of freight automatically receives a plan containing a number of trips to be performed to move freight using vehicles, and partially releases only a portion of the plan for execution instead of releasing the entire plan. The plan portion that is released includes a subset of trips that are selected by the computer from among all trips in the entire plan. Thereafter, the computer simply repeats the just-described acts. Iteratively releasing portions of a plan allows the computer to be instructed to release early certain trips that are satisfactory. Trips that are sub-optimal are re-generated in a next version of the plan, based on changes in orders in the interim. The computer may also be instructed to release a trip even if sub-optimal, if its time-to-departure becomes less than an advance notice needed by a truckload service that is to execute the trip.