In the era of digitalization, the process industry is one of the sectors most affected by the need for change. The adoption of IoT-based intelligent monitoring systems for the collection of real-time measurements of energy and other essential operational variables, on one hand, makes it possible to accumulate big data useful for the company management to monitor the stability of the production process over time, and on the other hand, helps to develop predictive models that enable more efficient work and production. The OTTORTO project stems from the need of the FARRIS company to adapt its production line to agriculture 4.0 policies, responding to the higher goals of digitization and technological transition imposed at the national and EU level. The objectives of the current study are (i) to present an “ad hoc” customized intelligent and multi-parameter monitoring system to derive real-time temperature and humidity measurements inside the company’s industrial drying kilns; and (ii) to show how it is possible to extract information from operational data and convert it into a decision support too and an effective knowledge medium to better understand the production process. Studying the correlations between temperature and humidity measurements showed that for most of the observation period, the system was thermodynamically quite stable in terms of major operational risks, such as humidity saturation inside the kilns causing condensation on the products to be dried. However, to remedy the occasional occurrence of such inefficiencies, implementing kilns with the introduction of forced air extraction systems could bring significant benefits in terms of improved energy-environmental performance.