Activation of chloramine‐T (TsNNaCl) with a Brønsted acid generates an active reagent for the double allylic C–H functionalization of tetrasubstituted alkenes in an intermolecular manner. The reaction generates a carbon–nitrogen and a carbon–chlorine bond, and proceeds with complete regio‐ and chemoselectivity. A total of 14 examples demonstrate the applicability of the dual C–H functionalization process. The mechanism involves the intermediacy of a 1,3‐butadiene derivative; 1,3‐butadienes can also be used directly as substrates.