We present, for the first time, a highly regio- and stereoselective ligand-divergent hydrosilylation reaction. The methodology produces diverse amido-vinyl silanes from readily available propynamides. Employing platinum catalysis utilizing commercially available ligands, silyl-α,β-unsaturated amides are produced in synthetically useful yields (up to 91%). This methodology allows, for the first time, an unprecedented ligand differentiated hydrosilylation methodology to form β-(E)-silyl-α,β-unsaturated amides in high regioselectivity and α-silyl-α,β-unsaturated amides with complete regioselective control (>99 : 1).