Thermosetting polymers are widely valued for their durability and performance, but their inherent permanent crosslinked structure poses significant challenges for recycling and reprocessing. Addressing this limitation, this study presents a novel sustainable approach by engineering a triol containing three thermo-reversible Diels-Alder adducts (DA-triol) in its structure and incorporating it into the synthesis of thermoset polyurethanes (PU). The thermo-reversible nature of the Diels-Alder reaction was thoroughly evaluated using differential scanning calorimetry (DSC) and Fourier Transform Infrared Spectroscopy (FTIR). Subsequently, the thermoset polyurethanes were heated to 140 °C to activate the retro-DA reaction, allowing softening and reshaping. Upon cooling, the DA-reaction restored the crosslinked network. This recyclability was harnessed to develop on-demand debonding adhesives. Wood specimens bonded with the synthesized PUs were successfully bonded and debonded, demonstrating the material's potential for environmetally friendly adhesive applications. This study underscores a transformative step toward recyclable thermosetting polymers, contributing to a circular materials economy.