In this work, cascade cyclizations of vinyl sulfonium salts with either indolyl chalcones or <i>ortho</i>‐amino trifluoroacetophenones are described. This protocol enables the assembly of fused 2,3‐dihyro‐1H‐pyrrolo[1,2‐a]indoles and fused tetrahydroquinolines containing a CF<sub>3</sub>‐substituted tetrasubstituted carbon stereocenters.