Reported herein is an unprecedented synthesis of C3‐fluorinated oxindoles through cross‐dehydrogenative coupling of C(sp3)‐H and C(sp2)‐H bonds from malonate amides. Under the unique and mild electrochemical conditions, the requisite oxidant and base are generated in a continuous fashion, allowing the formation of the base‐ and heat‐sensitive 3‐fluorooxindoles in high efficiency with broad substrate scope. The synthetic usefulness of the electrochemical method is further highlighted by its easy scalability and the diverse transformations of the electrolysis product. C−H functionalization: A ferrocene‐catalyzed electrochemical cross‐coupling reaction of C(sp3)‐H and C(sp2)‐H centers has been developed to give access to C3‐fluorinated oxindoles using fluorinated malonate amides. The electrosynthetic method is characterized by mild reaction conditions, broad substrate scope, high functional group tolerance, and easy scalability.