The salvage of “Yangtze River Estuary II” ancient wreck adopted the world’s first curved pipe based method. The mechanical design of the pipe jacking machine and the structure design of curved pipe relied on the understanding of the pipe-ground interaction mechanism and establishment of a reasonable model for calculating the driving force. Based on the understanding of the major factors contributing to the pipe-ground interaction, a theoretical model for calculating the driving force of curved pipe jacking machine with a small radius of vertical curvature was derived through equilibrium analysis. The dynamic jacking process of a single pipe was simulated using the coupled Eulerian Lagrangian (CEL) method, from which the evolution processes of ground stress and ground surface settlement during the curved pipe jacking process with a small radius of vertical curvature were obtained. The simulation results were compared with model test data, on-site monitoring data, and theoretical calculation results, whereby the characteristics of driven force evolution and its controlling factors were obtained. The research outcome can provide theoretical basis and technical support for future wreck salvage project similar to “Yangtze River Estuary II”.