Previous　N-glycosylation　approaches　have　predominately　involved　acidic　conditions,　facing　challenges　of　low　stereoselectivity　and　limited　scope.　Herein,　we　introduce　a　radical　activation　strategy　that　enables　versatile　and　stereoselective　N-glycosylation　using　readily　accessible　glycosyl　sulfinate　donors　under　basic　conditions　and　exhibits　exceptional　tolerance　towards　various　N-aglycones　containing　alkyl,　aryl,　heteroaryl　and　nucleobase　functionalities.　Preliminary　mechanistic　studies　indicate　a　pivotal　role　of　iodide,　which　orchestrates　the　formation　of　a　glycosyl　radical　from　the　glycosyl　sulfinate　and　subsequent　generation　of　the　key　intermediate,　a　configurationally　well-defined　glycosyl　iodide,　which　is　subsequently　attacked　by　an　N-aglycone　in　a　stereospecific　SN2　manner　to　give　the　desired　N-glycosides.　An　alternative　route　involving　the　coupling　of　a　glycosyl　radical　and　a　nitrogen-centered　radical　is　also　proposed,　affording　the　exclusive　1,2-trans　product.　This　novel　approach　promises　to　broaden　the　synthetic　landscape　of　N-glycosides,　offering　a　powerful　tool　for　the　construction　of　complex　glycosidic　structures　under　mild　conditions.　©　2024　Wiley-VCH　GmbH.