We describe the synthesis and characterization of novel redox-active tridentate pincer ligands with pendant H-bonding sites. The corresponding Ni complexes exhibit complex redox behavior and are active precursors in hydrogen production electrocatalysis, a property potentially relevant to solar-to-fuel conversion. The electrochemistry of the corresponding Zn complexes was investigated to explore ligand participation in the observed redox chemistry.Ni complexes with pendant N atoms show ligand redox activity as well as electrocatalytic activity for proton reduction.