The adoption of digital technology in maritime transport is currently essential and inevitable. Major global ports embracing these advancements to improve efficiency and resilience. However, the next frontier involves fostering digital collaboration among stakeholders in the maritime transport ecosystem. As Artificial Intelligence (AI) becomes critical in enhancing productivity, its integration into digital technologies is key to creating resilient ports capable of mitigating disruptions. While technological aspects have received ample attention, there is a lack of research addressing the human factors involved in AI driven digital collaboration platforms—particularly in Indonesian ports, which face unique geographical and disaster-related challenges due to the nation’s archipelagic nature. This study explores the human factors influencing the successful implementation of digital collaboration in Indonesian ports. It identifies human factor barriers that hinder the effective use of AI-driven technologies. Using qualitative interviews and simple quantitative survey, this research investigates the strategies necessary to address these human-centric challenges and optimize the role of individuals in digital transformation. Qualitative data is analyzed using thematic analysis, while quantitative data is presented using the Importance-Performance Matrix and Adoption Matrix. The findings present actionable strategies to overcome human factor barriers. A regulatory framework is proposed aimed at enhancing the resilience of Indonesia's port system. This paper offers a practical, human-centered approach to digital collaboration, ensuring that Indonesia’s port ecosystem becomes more adaptable to future disruptions and sustainable in a rapidly evolving digital landscape.