A robotic labeling system includes a package locating system and a package identification system identifying a package orientation. The robotic labeling system includes a label application system having first and second label printers and first and second label applicators. The label printers are both capable of printing a shipping label and a customer specific label. The first label applicator applies a first label (either the shipping label or the customer specific label) to a first side of the package while the second label applicator applies a second label (other of the shipping label or the customer specific label) to a second side of the package different than the first side. The printing and application of the labels is based on the orientation of the package.