Herein we report an atom- and step economic aromatic cyanoalkylation reaction that employs nitriles as building blocks and proceeds through C-sp(2)-H and C-sp(3)-H bond activation steps mediated by Ni-III. In addition to cyanomethylation with MeCN, regioselective alpha-cyanoalkylation was observed with various nitrile substrates to generate secondary and tertiary nitriles. Importantly, to the best of our knowledge these are the first examples of C-H bond activation reactions occurring at a Ni-III center, which may exhibit different reactivity and selectivity profiles than those corresponding to analogous Ni-II centers. These studies provide guiding principles to design catalytic C-H activation and functionalization reactions involving high-valent Ni species.