Comprehensive Summary A visible‐light‐induced tandem radical intramolecular cyclization/arylation of quinoxalin‐2(1 H )‐ones with bromodifluoroacetamides is described. This protocol allows efficient access to a variety of valuable α,α ‐difluoro‐ γ ‐lactam‐fused quinoxalin‐2(1 H )‐ones in moderate to good yields under metal‐free, mild and redox neutral reaction conditions. This strategy is tolerant of various functional groups and a broad range of substrates. The mechanism experiments suggested an involvement of 5‐ exo ‐trig cyclization and a radical process in this transformation.