The effect of the fastener’s failure in a railway track on the dynamic forces produced in the wheel-rail contact is studied using the simulation software VAMPIRE to assess the derailment risk of two different vehicles in two curves with distinct characteristics. First, a 3D-FEM model of a real track is constructed, paying special attention to fasteners, and calibrated with displacement data obtained experimentally during a train passage. This numerical model is subsequently used to determine the track vertical and lateral stiffness. This study evidences that although the track can practically lose its lateral stiffness as a consequence of the failure of 7 consecutive fasteners, the vehicle stability would not be necessarily compromised in the flawed zone. Moreover, the results reveal that the uncompensated acceleration and the distance along which the fasteners are failed play an important role in the dynamic behavior of the vehicle-track system,influencing strongly the risk of derailment. The effect of the fastener’s failure in a railway track on the dynamic forces produced in the wheel-rail contact is studied using the simulation software VAMPIRE to assess the derailment risk of two different vehicles in two curves with distinct characteristics. First, a 3D-FEM model of a real track is constructed, paying special attention to fasteners, and calibrated with displacement data obtained experimentally during a train passage. This study evidences that although there track can practically lose its lateral stiffness as a consequence of the failure of 7 consecutive fasteners, the vehicle stability would not be just compromised in the flawed zone. Moreover, the results reveal that uncompensated acceleration and the distance along which the fasteners are failed play an important role in the dynamic behavior of the vehicle-track system, influencing strongly the risk of derailm ent.