In this study, we devised a palladium-catalyzed efficient and versatile method for C(sp2)-H ortho-cyanomethylation of arylamides with a broad substrate scope and moderate to excellent yields. An inexpensive and commercially available chloroacetonitrile was employed as a cyanomethylating source. This method is also compatible with the air atmosphere. Further, the synthetic feasibility of this technique is established by gram-scale synthesis and functional group transformation of the products.