Abstract A sustainable parallel paired electrolysis methodology has been developed to synthesize α-hydroxy amides via hydride-free reduction of α-keto amides at the cathode and the esterification of aldehydes at the anode. Interestingly, any substitution at the α-keto amide not only affects the yield of the reduction process but also influences the oxidation process due to potential alignment. Radical-quenching experiments suggest a radical reaction pathway. The formation of an acyl radical is crucial to suppress the formation of the hemiketal intermediate.