A simple and convenient visible‐light‐promoted cascade difluoromethylation/cyclization reaction to access various difluoromethylated pyrrolo[1,2‐<i>a</i>]indolediones was developed using difluoromethyltriphenylphosphonium bromide salt as the difluoromethylated reagent under mild conditions. The methodology features a wide substrate scope, good functional group tolerance, good to excellent yields, and mild reaction conditions. A possible radical mechanism has been investigated and proven as a single electron transfer (SET) procedure.