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Abstract: This study presents the development of a real-time logistics fleet tracking system integrating Internet of Things (IoT) technology with a web-based platform to address the lack of accurate fleet visibility in small and medium logistics operations. Using an ESP32 microcontroller and the GY-NEO6MV2 GPS module, the system continuously transmits location data to a server, which is visualized through a responsive web application and used to compute shipping costs based on actual route distances. The system was developed using the Agile–Scrum methodology and modelled with Unified Modelling Language (UML), while MySQL served as the relational database backend. Functional evaluation demonstrated that all core features—registration, login, cargo management, and real-time tracking—operated reliably. System Usability Scale (SUS) testing yielded a score of 78.3 (“Good”), and User Acceptance Testing (UAT) with XYZ Cargo confirmed alignment with operational requirements. The results indicate that the proposed IoT-enabled architecture enhances tracking accuracy, operational efficiency, and service transparency within logistics workflows.