This study analyzes the challenges to the transformation of skill-based education within Iran's higher education system, explaining why, despite repeated emphasis in high-level policy documents, real transformation has not occurred. The research used a qualitative approach and a grounded theory strategy, with data from semi-structured interviews with thirteen experts—including senior managers from the Ministry of Science, officials from skill-oriented universities, and specialists—and an analysis of policy documents. Data analysis identified a "systemic gap" as the core category. This gap manifests in several areas, including a structural-institutional disconnect from fragmented policymaking centers and institutional parallelism; a cultural-attitudinal disconnect where credentialism overrides a focus on skills; and an implementation disconnect evidenced by the absence of a comprehensive development model and frequent policy shifts. Furthermore, the disconnect is apparent in the university-industry relationship, which suffers from a lack of coherent dialogue and mutual trust. It is also seen in curriculum planning shortcomings, such as inflexibility and the neglect of soft skills, and in applying fragmented strategies that lack necessary integration. This systemic gap has led to a "vicious cycle of non-transformation." In this cycle, structural disconnects lead to hasty policymaking, reinforced by cultural resistance, resulting in incomplete implementation and, ultimately, the formulation of new policies without learning from past experiences. The study concludes that Iran's primary problem is not a lack of policies, but this multidimensional systemic gap. Breaking this vicious cycle requires a comprehensive, integrated, and long-term approach to skill-based education.