Chiral sulfilimines, aza analogues of sulfoxides, are essential in natural products and pharmaceuticals, highlighting the importance of their synthesis in asymmetric catalysis. However, efficient approaches for synthesizing chiral diaryl sulfilimines are still rare and challenging, particularly for those with two sterically similar aryl groups. Herein, we present a mild and efficient protocol for generating diverse enantioenriched diaryl and aryl alkyl sulfilimines via copper-catalyzed enantioselective S-arylation of N-acyl sulfenamides with diaryliodonium salts. A bulky PyBox ligand is crucial for stereocontrol, delivering various sulfilimines with up to 95% ee (51 examples).