The need for studies connecting machine explainability with human behavior is essential, especially for a detailed understanding of a human’s perspective, thoughts, and sensations according to a context. A novel system called RYEL was developed based on Subject-Matter Experts (SME) to investigate new techniques for acquiring higher-order thinking, the perception, the use of new computational explanatory techniques, support decision-making, and the judge’s cognition and behavior. Thus, a new spectrum is covered and promises to be a new area of study called Interpretation-Assessment/Assessment-Interpretation (IA-AI), consisting of explaining machine inferences and the interpretation and assessment from a human. It allows expressing a semantic, ontological, and hermeneutical meaning related to the psyche of a human (judge). The system has an interpretative and explanatory nature, and in the future, could be used in other domains of discourse. More than 33 experts in Law and Artificial Intelligence validated the functional design. More than 26 judges, most of them specializing in psychology and criminology from Colombia, Ecuador, Panama, Spain, Argentina, and Costa Rica, participated in the experiments. The results of the experimentation have been very positive. As a challenge, this research represents a paradigm shift in legal data processing.