This chapter of 'Contributions to the Ordovician paleontology of Kentucky and nearby states' deals with the stratigraphic distribution, paleoecology, biogeography, and systematic paleontology of 50 species of nautiloid cephalopods from the Midcontinent. The species are placed in 30 genera. Most of the specimens are silicified and from Middle Ordovician rocks of Kentucky. The study is augmented by unsilicified material from the Upper Ordovician Cincinnatian Provincial Series from the tri-state area of Kentucky, Indiana, and Ohio.