The finite-element method (FEM) has been used to numerically investigate the effect of work roll configuration on the leveling effectiveness of tail-up bent plates. Leveling is a process used to minimize shape defects, including flatness imperfections and uniformity of internal stresses in shape-critical applications. Leveling plays an important role in delivering the desired plate shape and meeting the required product standards. To simulate the roller leveling effectiveness of tail-up bent plates, an initially flat plate was plastically bent prior to leveling and was passed through the leveling rolls. Leveling effectiveness was estimated by the vertical displacements of tail-up bent plates with two different roll configurations. One configuration adopts a gradually increasing roll gap, while the other configuration maintains the same roll gap in the first two sets of rolls and gradually increases the roll gap for the later rolls. For comparison purposes, the entry and exit roll gaps of the two roll configurations are set to the same roll gap. To verify the accuracy of the numerical simulations, actual leveling experiments were performed using tail-up bent plates. The results show that the roll configuration significantly influences the leveling effectiveness of the tail-up bent plates. Higher leveling effectiveness is obtained for a leveling configuration that imparts more severe deformation at the earlier leveling stages. Through the analysis, the work roll configuration is determined to be essential to increase leveling effectiveness of tail-up bent plates.