To investigate the characteristics of reservoir damage caused by CO2 flooding in shale oil reservoirs, natural core samples and shale oil from a formation in western China were subjected to laboratory experiments focusing on damage mechanisms including gas channeling, asphaltene deposition, and the Jamin effect. The results showed that gas channeling leads to gas breakthrough in high-permeability layers, reducing overall recovery efficiency during co-production; asphaltene deposition has a more pronounced impact on low-permeability cores, particularly near the injection side; and the Jamin effect reduces permeability when downstream backpressure falls below the minimum miscibility pressure, with low-permeability cores being more severely affected and harder to restore than high-permeability ones. Based on the experimental findings and mechanism analysis, several micro-regulation strategies were explored—such as permeability variation analysis, NMR response, and contact angle testing—to evaluate their effectiveness in mitigating typical damage mechanisms. Mitigation measures, including gas–water alternation, anti-deposition treatments for injection wells, and adjustments to production pressure differentials, are proposed to reduce reservoir damage and provide theoretical and technical support for efficient shale oil recovery via CO2 flooding.