The extant literature has identified that the ongoing digitalisation of port operations, specifically in developing countries around the globe, is inhibited by stakeholder resistance stemming from digital literacy limitations. This study aims to assess and develop strategies to improve the digital literacy of stakeholders involved in port operations through a case study with an Indonesian Port Corporation. We found a gap between the digital literacy level expected by the port management and the digital literacy levels of employees. We discuss several antecedents to this problem and subsequently propose a set of recommendations to address the gap identified. These recommendations include establishing in-house training, scholarship programs, employee exchange program, and using the digital literacy assessment framework proposed in this study to monitor any uplift in digital literacy levels. This study offers important implications for research and practice related to digital literacy in the context of supply chain management in developing countries.