An automated vial label assembly for three-sided pharmaceutical vials includes a conveyor assembly, an elevator assembly, and a printer assembly. The labeling process may be controlled and programmed by a computing device with sensors present at deliberate points throughout the assembly to communicate and transmit information back to the computing device. Such information may include the location and position of the vial, the status of the printed label, and the rotational speed of the container and label assembly. This system may be used to label any size or shape of bottle, including more traditional cylindrical or square shaped containers. The labeling module may be used as a stand-alone labeling system or may be a module used in combination with a larger system such as a pharmaceutical dispensing assembly whereby vials may be sorted, labeled, and filled with the appropriate medications.