This study conducts a comparative analysis of Hong Kong Port and Port Klang in Malaysia to examine how artificial intelligence (AI)–driven technologies are shaping divergent pathways toward port decarbonization. While both ports operate as major maritime hubs faced with growing environmental and competitive pressures, their approaches in green shipping vary substantially. To account for these differences, the study applies Entangled Political Economy (EPE) theory, which views technological and environmental transitions as emerging from dense and evolving interdependencies among state institutions, regulatory frameworks, and market actors. This research draws on official statistics, government documents, port authority reports, industry publications, field observations, and semi structured interviews with policymakers, port operators, and logistics stakeholders, and investigates how each port incorporates AI into operational efficiency, and emissions reduction initiatives, and how their distinct institutional entanglements shape these paths. The study contributes original insights to transport policy, green and smart port development, and environmental governance by demonstrating the value of an EPE-informed perspective for understanding how political–economic contexts condition digital and green transitions in the maritime sector.