Well-preserved shells of Ashgill (Katian–Hirnantian) and Llandovery nautiloids from Anticosti Island include the type species of 10 genera. From a diversity high of some 40 described nektic and nektobenthic species during the deeper water, distal shelf facies of the Vaureal Formation (late Katian, Richmondian), the succeeding Hirnantian shows a decline to ca. 19 species in the shallower water Ellis Bay Formation. A number of Katian species possessed very large orthoconchs (>1 m in length), but Hirnantian species were less than half that size. The initial earliest Silurian (Rhuddanian, Becscie Formation) recovery nautiloid fauna is impoverished, with low diversity (one sp.?), and generally dwarfed, to shells with diameters of <1 cm. Nautiloid diversity expanded and progressed to some 22 species in the late Aeronian through Telychian Jupiter and Chicotte formations, with an apparent peak in the Goéland Member of the Jupiter Formation. Three new species, Actinoceras lesperancei, Eridites barnesi, and Diestoceras macgilvrayoceras, are described. The distribution of shells within the succession defines the fauna’s stratigraphic and paleobiogeographic significance, with a changing mix of Baltic and Laurentian taxa.