An organophotoredox-catalyzed divergent cyanoalkylation/cyanoalkylsulfonylation of enamides in a highly regio- and stereoselective manner has been reported. In this mild and efficient protocol, cyclobutanone oxime esters serve as a cyanoalkylating source and inexpensive K2S2O5 serves as an SO2 surrogate. Broad substrate scope, compatibility of various sensitive functional groups and further functional group transformation are the highlights of this method.