An umpolung addition of dicyanobenzene to α,β-unsaturated alkenes has been developed using an electroreductive strategy. This electrochemical protocol is well compatible with a broad range of conventionally challenging substrates, including α,β-unsaturated esters, nitriles and trisubstituted enones. Moreover, good to excellent regioselectivities are observed in the reaction of cinnamates with dicyanobenzene. Synthetic utility of this electrochemical approach is further demonstrated by direct late-stage functionalization of (S)-verbenone and 16-dehydropregnenolone acetate.