The integration of new freight transport technologies into port areas requires a detailed understanding of success factors, drivers, and barriers — with the Port of Trieste serving as a representative territorial case. In this context, the local rail operator plans to implement predictive maintenance solutions for freight transport. Although several research gaps remain, this study aims to explore how technology is embedded within the territorial context, assessing the opportunities and vulnerabilities of port–territory synergies from an innovation-driven perspective.The article proposes a holistic model that incorporates territorial, technological, geographic, and port-related dimensions to analyse the integration of predictive maintenance through a geographic-economic lens. The model supports the case study and provides insights for replication in other port environments.