It is generally accepted that selecting the key segment position for trapezoidal tapered rings and controlling the shield machine advancement are challenging tasks for shield tunneling projects. In this work, we propose a method for calculating the key segment position based on the shield tail gap, jack stroke difference, and lining trend. To calculate all possible key segment positions other than that corresponding to the straight joint configuration, the shield tail gap that remains after segment assembly and the jack stroke difference corresponding to the advancement of the segmental lining and lining trend were computed; then, values and importance coefficients were assigned to these factors according to current operating conditions. To ensure that the segmental lining can be assembled successfully with the calculated key position, we established a model to calculate the change in the shield tail gap before and after shield machine advancement based on the spatial relationships of the shield machine, the currently installed segmental rings, and the segment to be installed. Further, we propose a method for calculating the range of jack stroke differences when the predetermined “permitted shield tail gap” and key position are provided. The method is based on the change in the shield tail gap calculated with the above model and the positional relationship between the shield machine’s actual axis and the designed tunnel axis after the current segmental ring has been assembled. The calculated range of jack stroke differences may then be used to control the advancement of the shield machine. We validated the viability of our methods by using the data of Phase 1 works on Line 2 of the Ningbo Rail Transit system.