In this paper, based on the theory of gas flow, the action logic of the control valve, and the principle of multi-rigid-body dynamics, a simulation model of the 20,000 t heavy haul combined train is established to investigate the influence of brake pipe pressure gradient on the braking performance, longitudinal dynamics, braking and release characteristics of trains. Utilizing real railway line conditions, locomotive and vehicle parameters, and train operation monitoring equipment (LKJ) record data of Shuozhou-Huanghua Railway, the cyclic braking condition of the train on the long and steep downhill is simulated, and the control strategy of reducing the coupler force during the cyclic braking is proposed. The results indicate that a larger brake pipe pressure gradient before braking leads to weaker braking capability, and higher coupler forces during braking, but smaller coupler forces during release. As the brake pipe pressure gradient before braking increases, braking synchronicity decreases, while release synchronicity slightly improves. By adjusting the locomotive’s electric braking force during the cyclic braking, it is possible to appropriately increase the brake pipe pressure gradient before braking, effectively reducing coupler forces during release and reducing the number of braking cycles, thus lowering the operational difficulty of the train.