In recent years, considerable advances in connecting industrial equipment to the Internet allowed a higher level of operational efficiency, productivity, and automation. Nevertheless, the construction industry still presents challenging requirements, like long-distance wireless communication, interconnection of out-ofcoverage areas, constant mobility of machinery, and support for legacy and proprietary systems. All these requirements pose different challenges when compared with traditional smart factory Industry 4.0 solutions. This paper discusses some of the current key questions regarding fleet management in the construction industry, identifies requirements for heavy-duty machinery, and proposes an Industrial Internet of Things (IIoT)-based solution for the integrated monitoring of such machinery. Also, it proposes and presents an open, innovative solution for the integrated management of non-standardized civil construction vehicle technologies. The developed prototype uses the J1939 protocol to collect machinery status and Long-Range Wide Area Network (LoRaWAN) to communicate the monitored data. The solution was assessed at the construction site of the new port of Sines in Portugal. A detailed description of the proposed system is provided, along with information on trials and evaluation results regarding its performance. Additionally, the paper provides insights into open issues and challenges in this field and how our solution can contribute to overcoming them.