3-Benzylmenadiones were obtained in good yield by using a blue-light-induced photoredox process in the presence of Fe(III), oxygen, and γ-terpinene acting as a hydrogen-atom transfer agent. This methodology is compatible with a wide variety of diversely substituted 1,4-naphthoquinones as well as various cheap, readily available benzyl bromides with excellent functional group tolerance. The benzylation mechanism was investigated and supports a three-step radical cascade with the key involvement of the photogenerated superoxide anion radical.