Supramolecular rubbers based on 2-aminoethylimidazolidone and fatty acids with epoxy crosslinks have been shown to self-heal via multiple hydrogen bonding sites. In this work, several tools are used to investigate the molecular mechanisms taking place at the interface to understand cohesive healing in these polymers. The quantification of self-healing was performed via a tapered double cantilever beam (TDCB) geometry. The TDCB geometry is especially amenable to studying multiple healing cycles due to the fracture toughness, and subsequently healing efficiencies being independent of crack length. Healing was carried out for multiple fracturehealing cycles and varying fracture testing experimental parameters to track the change in efficiency of interfacial healing. Strain rate and rate of crack closure are both shown to affect the self-healing efficiency.