A critical practical challenge in the operation of medical insurance is the difficulty in recovering advanced payments from tortfeasors in third-party tort cases. From a jurisprudential perspective, this paper analyzes the causes of this dilemma across three dimensions: social perceptions, systemic coordination, and institutional operation. The failue of recovery is not a problem of a single link, but the result of a triple overlap: the weakening of the insured's duty to disclose, the dormancy of the advance payment system, and the ineffectiveness of administrative recovery. At the root of the problem lies the public's insufficient awareness of the “social risk-sharing” nature of the medical insurance fund, the lack of effective information exchange mechanisms between judicial authorities and healthcare security administrations, and the disconnect between rule design and the realities of medical treatment and litigation. To solve this dilemma, it is necessary to promote a shift in public perception from individual welfare to social risk-sharing, establish a collaborative working mechanism among courts, procuratorates, and healthcare security administrations, remove blockages in information sharing and procedural coordination, and improve internal closed-loop management of recovery along with supporting measures such as credit sanctions. The effective realization of the medical insurance fund's right of recovery depends on bridging the gap between “law in books” and “law in action”.