Thermoset polyurethanes invite industrial interest for their versatility and chemical and mechanical resistance due to their permanently crosslinked networks; yet this structural feature severely limits their recyclability. Recent advances in Covalent Adaptable Networks (CANs), enabled by Dynamic Covalent Chemistry (DCC), have demonstrated promising pathways toward reprocessability through bond-exchange mechanisms. However, no clear link has yet been identified between material properties and the retention of performance after reprocessing. This work investigates the role of crosslink density as a key factor in determining the reprocessability of polyurethane networks. Two model systems with comparable compositions but distinct crosslink densities were synthesised, reprocessed, and compared. Relaxation analysis based on the Maxwellian approach proved insufficient to predict reprocessing outcomes. Only the highly crosslinked network yielded homogeneous reprocessable films with significant retention of mechanical performance, whereas the less crosslinked network resulted in incoherent materials with markedly reduced properties. The application of Kohlrausch–Williams–Watts (KWW) fitting revealed that dynamic covalent exchange dominates relaxation in the highly crosslinked system, while in the looser network, relaxation is governed by soft segment mobility, hindering effective network reformation. These findings underscore the pivotal role of crosslink density in determining the recyclability of thermoset polyurethanes and provide new insights for the rational design of reprocessable materials.