The transition toward a smart ecosystem has become an undeniable necessity for maintaining port competitiveness and ensuring supply chain resilience. However, in the context of developing economies, this transition requires moving beyond a purely technology-driven perspective and placing greater emphasis on addressing deep-rooted structural and operational bottlenecks—an objective attainable only through the active engagement of all port stakeholders. Departing from conventional and static maturity assessment models, this study develops a forward-looking Multi-Criteria Decision-Making (MCDM) framework specifically designed to evaluate port readiness and prioritize ports for smart ecosystem implementation. To this end, the Best–Worst Method (BWM) is employed to derive robust weights for key indicators emerging from the intersection of operational challenges, infrastructural readiness, technology implementation risks, and geoeconomic characteristics. Subsequently, by integrating the TOPSIS and PROMETHEE techniques, a comprehensive network of Iranian commercial ports is ranked and prioritized according to their smart transformation potential.To ensure the robustness of the results under different scenarios, the proposed evaluation framework is further strengthened through Monte Carlo simulation and comprehensive sensitivity analysis. The findings suggest that large-scale resource allocation in this domain must be aligned with each port’s absorptive capacity, risk tolerance, and inherent contextual conditions. Accordingly, a one-size-fits-all approach lacks both efficiency and strategic justification. Instead, ports require differentiated policy strategies tailored to local conditions. In this regard, a “big-bang” transformation approach should be avoided in favor of a modular, bottleneck-driven development strategy. Ultimately, the proposed hybrid model provides port authorities and policymakers with a flexible roadmap for designing and implementing smart transformation in developing countries’ ports, grounded in resolving operational challenges and guided by a “start small, think big” strategy.