Recently,　the　introduction　of　fluorosulfonyl　(-SO2F)　groups　have　attracted　considerable　research　interests,　as　this　moiety　could　often　afford　enhanced　activities　and　new　functions　in　the　context　of　chemical　biology　and　drug　discovery.　Herein,　we　report　the　design　and　synthesis　of　1-fluorosulfamoyl-pyridinium　(FSAP)　salts,　which　could　serve　as　an　effective　photoredox-active　precursor　to　fluorosulfamoyl　radicals　and　enable　the　direct　radical　C-H　fluorosulfonamidation　of　a　variety　of　(hetero)arenes.　This　method　features　mild　conditions,　visible　light,　broad　substrate　scope,　good　group　tolerance,　etc.,　and　a　metal-free　protocol　is　also　viable　by　using　organic　photocatalysts.　Further,　FSAP　can　also　be　applied　to　the　radical　functionalization　of　alkenes　via　1,2-difunctionalization,　radical　distal　migration,　tandem　radical-polar　crossover　reactions,　etc.　In　addition,　a　formal　C-H　methylamination　of　(hetero)arenes　by　combining　this　radical　C-H　fluorosulfonamidation　with　subsequent　hydrolysis　as　well　as　product　derivatization　are　also　demonstrated.　1-Fluorosulfamoyl-pyridinium　(FSAP)　was　designed　and　synthesized　as　a　redox-active　fluorosulfamoyl　radical　precursor,　which　can　be　applied　in　radical　C-H　fluorosulfonamidation　of　a　variety　of　(hetero)arenes.　Further　utilization　in　the　radical　1,2-functionalization,　radical　distal　migration,　tandem　radical-polar　crossover　reactions　of　olefins　is　also　demonstrated.　image