A major challenge in developing recyclable polymeric materials is the inherent conflict between the properties required during and after its life span. In particular, materials must be strong and durable when in use, but undergo complete and rapid degradation upon end-of-life. We report a new mechanism for degrading polyurethanes called CyclizAtion-Triggered CHain (CATCH) cleavage that achieves this duality. CATCH cleavage features a simple glycerol-based acyclic acetal unit as a kinetic and thermodynamic trap for gated chain-shattering. Thus, an organic acid induces transient chain breaks with oxocarbenium ion formation and subsequent intramolecular cyclization to depolymerize fully the polyurethane backbone at room temperature. With minimal chemical modification, the resulting degradation products can be repurposed into strong adhesives and photochromic coatings demonstrating the potential for upcycling. The CATCH cleavage strategy for low-energy input breakdown and subsequent upcycling may be generalizable to a broader range of synthetic polymers and their end-of-life waste streams.