This paper proposes a cloud application architecture called OLEA, for monitoring the olive oil production chain. OLEA system deployment follows adivide–and-conquer management logic, which maintains olive tree clusters. On each cluster, NFC technology is used for monitoring plant protection practices and fertilization. Apart from on-site monitoring services, the system is also equipped with virgin oil management services. It uses an OLEA system controller that interconnects with sensors on oil mills, for the procurement of quantitative and qualitative olive oil characteristics, during the industrial extraction process. OLEAsystem services and management algorithms are controlled by a cloud application server, where collected data uploads and notifications are sent to the end users using a mobile phone application. This paper presents the OLEA system technical characteristics as well as the structure of OLEA communication protocols. Furthermore, a case study of the OLEA system data mining capabilities is presented examining the application of such efforts to the improvement of systematic cultivation, branding and product exports.