Abstract: According to one general aspect, a method of transportation management may include receiving a request to transport a current freight unit from a current source location to a current destination location. The method may include selecting a prior shipment path based upon a similarity, as defined by a set of predefined criteria, between the current freight unit and a prior freight unit. The method may further include initializing a shipment path improver with the prior shipment path. The method may also include generating, via the shipment path improver, a current shipment path for the current freight unit from the current source location to the current destination location based upon the prior shipment path.