Olive oil production is among the most significant pillars of crop production, especially in the Mediterranean region. The management risks undertaken throughout the olive oil production chain can be minimized using smart tools and applications. This review addressed the influence of the fruit fly of Bactrocera oleae (B. oleae) or Dacus oleae on the quality and antioxidant activity of the olives and their products based on the most recent literature data. Furthermore, in this review, we focused on the latest research achievements in remote sensor systems, features, and monitoring algorithms applied to remotely monitor plant diseases and pests, which are summarized here. Thus, this paper illustrates how precision agriculture technologies can be used to help agricultural decision-makers and to monitor problems associated with integrated pest management for crops and livestock, achieving agricultural sustainability. Moreover, challenges and potential future perspectives for the widespread adoption of these innovative technologies are discussed.