DDWC (Directional Drilling with Casing) is an effective wellbore construction technique, particularly suitable for soft marine formations. In DDWC, the casing replaces the drill pipe for sliding drilling operations, and the passability of the drill string through the casing has become one of the primary challenges in applying DDWC. This study uses ANSYS Workbench to simulate the strain and bending behavior of the casing under various geological conditions. Simulations were conducted for different wellbore trajectories, casing specifications, and materials to evaluate the feasibility of the drill string passing through the casing under different conditions. The results show that, when the dogleg severity reaches 18°/30 m and the casing’s inner diameter is 315 mm, the maximum radial strain of the casing is 4.2 mm, which cannot guarantee the successful passage of a drill string assembly with a 311 mm outer diameter. For other casing specifications, with a minimum inner diameter of 317 mm, the drill string can pass through under the maximum dogleg severity. Additionally, since the elastic modulus and Poisson’s ratio of the casing materials are identical, the strain behavior is consistent across different materials, meaning that the material does not affect the passability of the casing. Moreover, the study optimized the selection of casing specifications and materials. From the perspective of ensuring drill string passability and resource conservation, a casing with an inner diameter of 319.4 mm was chosen. To ensure the longevity of the casing and the stability of the wellbore, N80 steel was selected as the material. A sensitivity analysis was conducted on the factors affecting casing strain, and the results aligned with the simulation findings, showing that wellbore trajectory and casing specifications have a significant impact on casing strain. Verifying the passability of the drill string through the casing is critical for the development and application of DDWC technology.