This Account describes the recent advances in our research program toward the development of cobalt-catalyzed C-H amidation reactions. In particular, synthetic versatilities of obtainable amino products shown to be achieved on the basis of two distinctive mechanistic scaffolds; inner-and outer-sphere pathways. It highlights our approaches to transit the modes of C-N bond formation by introduction of bidentate LX-type ligands into Cp*Co(III) precursors, thereby broadly expanding the scope of amination reactions. 1 Introduction2 Cp*Co-Catalyzed Inner-Sphere C-H Amidation3 Cp*Co-Catalyzed Outer-Sphere C-H Amidation3.1 C(sp2)-N Bond Formation3.2 C(sp3)-N Bond Formation4 Conclusion