The transition from conventional supply chains to digitally enabled supply chains has been sped up by the emergence of digital technology, but many businesses still struggle with adoption because of a number of interconnected barriers. A thorough literature analysis led to the original identification of 25 barriers, which were then narrowed down to 17 major barriers in four categories: technological, organizational, operational, and economic. The Fuzzy Best–Worst Method (FBWM), which successfully controls uncertainty and lessens inconsistency in expert opinion, is used in this study to rank these barriers. According to expert assessments, the biggest challenges are lack of support from top management and a lack of digital skills and talent, which are followed by large investment in digital infrastructure. The stability of the rankings was validated through comparative analysis with other fuzzy multi-criteria decision-making techniques. The results highlight that, although important, personnel and budgetary concerns become secondary if leadership commitment and technology preparedness are met as requirements for a successful digital supply chain implementation. By providing a structured framework that directs managers especially in situations with limited resources to prioritize efforts for digital transformation.