N-glycosides　exhibit　diverse　biological　and　pharmacological　activities,　making　their　efficient　synthesis　crucial　for　both　biological　research　and　drug　development.　Traditional　acid-promoted　N-glycosylation　methods,　which　rely　on　the　formation　of　oxocarbenium　intermediates,　often　face　significant　challenges.　These　methods　are　water-sensitive　and　typically　require　neighboring　group　participation　to　achieve　high　selectivity.　Furthermore,　they　depend　on　acid　activation,　rendering　them　incompatible　with　alkyl　amine.　Additionally,　low-nucleophilicity　amides　often　need　to　be　converted　into　their　TMS-derivatives　to　enhance　reactivity,　limiting　the　direct　use　of　such　substrates.　In　contrast,　radical-based　strategies　have　emerged　as　a　promising　alternative,　addressing　many　of　these　limitations　and　leading　to　notable　advances　in　N-glycosylation.　This　review　explores　the　unique　properties　of　N-glycosides,　the　inherent　challenges　of　traditional　N-glycosylation　techniques,　and　the　transformative　advantages　offered　by　radical-based　approaches.　Specifically,　it　highlights　recent　advancements　in　radical-mediated　N-glycosylation,　including　photoredox　radical　strategies,　radical/ionic　hybrid　approaches,　and　metallaphotoredox　catalysis,　accompanied　by　a　detailed　discussion　of　the　underlying　mechanisms.　Finally,　the　ongoing　challenges　and　potential　future　directions　of　N-glycoside　synthesis　using　radical　strategies　are　presented.