Ruppert's reagent, (trifluoromethyl)trimethylsilane (Me₃SiCF₃) is now firmly established as a powerful tool for direct construction of C-CF₃ bond formation and it has been extensively studied for the synthesis of trifluoromethyl-containing compounds, particularly in the fields of medicinal chemistry and material. A large number of nucleophilic trifluoromethylation of carbonyls and imines using Me₃SiCF₃ have been investigated, however, the addition of Me₃SiCF₃ to electron-deficient alkenes as represented by the Michael addition reaction remains a challenge. Herein, we report the organocatalyzed allylic trifluoromethylation of Morita-Baylis-Hillman adducts using Ruppert's reagent and it was achieved in high to excellent yields via a successive S_N2'/S_N2' mode for the first time. The reaction was extended to the asymmetric allylic trifluoromethylation by the use of chiral catalysts.