The paper is devoted to the development and scientific substantiation of a concept for organizing intelligent monitoring of grain production in the context of digitalization of the agro-industrial complex. The purpose of the study is to form an integrated approach to monitoring organization that ensures information support for managerial decision-making at various levels of governance and enhances the resilience of the grain sector under conditions of increasing uncertainty. The methodological framework of the research is based on systemic and institutional approaches, as well as the provisions of the theory of technological paradigms and the digital economy. The study employs monographic, abstract-logical, economic-statistical methods, expert assessment, and a computational-constructive approach. As a result, the fundamental principles of organizing intelligent monitoring of grain production are formulated, a conceptual model of its functioning is developed, and the role of key institutions—data preparation, information and advisory support, and a digital platform—is substantiated. It is demonstrated that integrating monitoring functions into a unified management framework makes it possible to overcome the fragmentation of digital initiatives, reduce transaction costs, and ensure the scaling of intelligent technologies in grain production. The practical significance of the results lies in their applicability to the development of digitalization programs for the agro-industrial complex and the design of monitoring and decision-support systems.