Abstract: The rapid development of the digital economy has driven the rapid expansion of the flexible employment population, which now accounts for more than one-fourth of the total employed population. The lack of occupational injury protection for flexible workers has become increasingly prominent. This study analyzes the development and growth of the flexible employment population in China, examines the evolution of occupational injury insurance policies, and analyzes the existing issues such as low overall coverage, high enrollment but low coverage, high enrollment in low-risk occupations but low enrollment in high-risk occupations, and high insurance fund surplus. Taking the platform employment as an example, it identifies the reasons for the lack of occupational injury protection for flexible workers, including the absence of labor relations, high social insurance costs, and significant moral hazard. Based on the perspective of guiding the regularization of social security for flexible workers, this study proposes policy recommendations from the aspects of improvement of top-level law, mechanism design, coverage level, and strengthening support.