Systems, methodologies, media, and other embodiments associated with transportation planning in light of drop trailer arrangements are described. One exemplary computer-implemented method embodiment includes receiving orders that describe items to be delivered to facilities as controlled by order requirements. The method may also include accessing a transportation planning model that includes information concerning shipping modes and carriers by which an order can be delivered to a facility. The transportation planning model may also include data concerning drop trailer arrangements between facilities and the carriers. The method may also include selectively consolidating orders into shipments based on the transportation planning model and the availability of a drop trailer arrangement. The method may also include selectively assigning shipments to loads based on the transportation planning model and the availability of a drop trailer action. The method may output an actionable plan of loads stored, for example, on a computer-readable medium.