Shale oil represents a relatively new form of unconventional oil and gas resource, and the extensive exploration and development of shale oil resources carry significant implications for China’s oil and gas supply and demand dynamics. At present, within the realm of low-maturity shale oil extraction technologies, the reservoir must be subjected to elevated temperatures ranging between 400 to 60 °C. Prolonged exposure of wellbores to such high temperatures can result in a substantial decrease in cement strength, the formation of microcracks due to cement cracking, and damage stemming from thermal stresses on the casing. Casing damage stands out as a prominent factor contributing to wellbore integrity failures and well shutdowns within the context of shale oil development. Given the limited natural energy reservoirs of shale oil formations, it becomes necessary to supplement the reservoir’s energy during the development process. Furthermore, shale oil exhibits high viscosity and poor flowability, and conventional water injection methods yield limited efficacy. This situation can induce significant shifts in the stress field and rock mechanical parameters, potentially activating specific formations and complicating the load dynamics on the casing. Consequently, the risk of failure increases. In light of these considerations, this study uses numerical simulations to study the integrity of high-temperature injection and production wellbores in shale oil and aims to encompass a comprehensive evaluation and analysis of the principal factors that influence casing damage, the fluctuations in thermal stress, and the yield strength of various steel grades of casings exposed to alternating stress conditions. Subsequently, this paper developed a model for simulating the temperature and pressure within shale oil and steam injection wellbores to support engineering design analysis. The research results indicate that the application of pre-stress results in a significant increase in stress at the casing pipe head while causing a noticeable decrease in stress within the pipe wall. When N80 casing is used, the entire casing experiences thermal stresses surpassing the casing’s yield limit. Stress concentration may arise at both ends of the external seal, potentially leading to casing contraction, shear failure, and, under non-uniform stress conditions, casing bending deformation. The temperature of steam injection significantly influences the temperature field of the casing wall, with stress values experiencing a marked reduction when the steam injection temperature decreases from 350 °C to 200 °C, underscoring the substantial impact of temperature on casing thermal stress. As the steam injection process advances along with injection-production cycles, shear stresses at the interface can exceed the bond strength, resulting in relative slippage between the cement and the casing. The bonding force between the wellbore and the cement primarily depends on the interface’s friction, particularly in the context of friction during wellhead lifting. This study endeavors to determine rational injection and production parameters under varying conditions, optimize completion methods, reduce casing damage, and extend the casing’s operational life; it aims to offer critical technical support for the safe and efficient development of shale oil resources.