The interfacial fracture toughness between semi-crystalline polymers (polyamide/polypropylene) were studied to understand the failure mechanisms at the interface, especially when the interface was reinforced by an in situ compatibilizer. Based on the observation of the interface using scanning electron microscopy and wide angle X-ray spectroscopy, it was revealed that crystalline structure of polypropylene was not affected by the in situ compatibilizer at the interface. The reinforcing mechanism could be qualitatively identified by investigating the evolution of fracture toughness as a function of annealing time and temperature. The adhesion strength increased with the annealing time. Depending on the annealing temperature, the fracture toughness passed a peak value and then reached a plateau after some bonding time. As long as the chain length of the compatibilizer is long enough to form entanglements with the molecules at both bulk sides, the fracture at the interface is decided by the balance between adhesion strength at the interface and cohesive strength in the weak modulus side; the failure locus follows the lower one. Thus, adhesive failure occurred first when the reaction at the interface did not occur long enough to provide high adhesive strength at the interface, but the cohesive failure occurred in the crack propagation side after the adhesive strength value became higher than the cohesive strength value.