Herein, we describe a novel protocol for visible-light-induced α,γ-C(sp3)-H difunctionalization of piperidines. This redox-neutral, atom-economical protocol, which exhibits a broad substrate scope and good functional group compatibility, constitutes a concise, practical method for constructing piperidine-containing bridged-ring molecules. Preliminary mechanistic studies indicated that highly regioselective activation of the inert γ-C(sp3)-H bond of piperidines was achieved through a 1,5-hydrogen atom transfer reaction of a nitrogen radical generated in situ.