Having demonstrated the generality of the photochemical cross-electrophile coupling between sulfonyl hydrazones and RAEs, we turned our inquiry toward the potential extension of this protocol to facilitate the late-stage functionalization (LSF) of more complex molecules, such as peptides. Given the increasing prominence of peptides as therapeutic modalities, the development of methods capable of functionalizing extensive amino acid sequences directly on resin becomes especially valuable, enabling the generation of diversity without necessitating the development of de-novo synthetic methods. Moreover, on-resin modification brings forth substantial practical advantages, addressing key challenges related to purification and solubility that are often encountered in peptide chemistry in solution. Specifically, considering the well-documented compatibility of redox-active ester synthesis with solid-phase approaches, and the mild basic condition of our two-step protocol, we hypothesized that adapting this photochemical transformation to heterogeneous conditions on resin would be an attainable objective.