Unlike　the　well-established　fluoroalkylation,　the　direct　incorporation　of　multiple　fluorine　atoms　into　small　molecules　via　iterative　fluorinations　has　been　much　less　investigated.　Herein,　we　report　a　hypervalent　iodine　catalytically　selective　multi-fluorination　in　which　the　fluorination　degree　is　controlled　by　the　delicate　balance　between　the　HF/amine　ratios.　The　pros　and　cons　of　hypervalent　iodine　catalysis　and　the　previously　established　electrochemical　approach　in　the　iterative　multi-fluorinations　are　also　provided.　©　2024　The　Royal　Society　of　Chemistry.