The construction of Se-CF3 bonds represents a powerful yet challenging strategy for accessing either alkyl- or aryl-substituted trifluoromethyl selenides, primarily due to the limitation of suitable Se-containing precursors. Herein, we report a catalytic base-induced trifluoromethylation/fluoroalkylation of selenosulfonates using the commercially available Ruppert-Prakash reagent. Furthermore, this transition-metal-free protocol enables the synthesis of a diverse range of trifluoromethyl sulfides.