Nowadays, in the context of Industry 4.0, advanced working environments aim at achieving a high degree of human–machine collaboration. This phenomenon occurs, on the one hand, through the correct interpretation of operators’ data by machines that can adapt their functioning to support workers, and on the other hand, by ensuring the transparency of the actions of the system itself. This study used an ad hoc system that allowed the co-registration of a set of participants’ implicit and explicit (I/E) data in two experimental conditions that varied in the level of mental workload (MWL). Findings showed that the majority of the considered I/E measures were able to discriminate the different task-related mental demands and some implicit measures were capable of predicting task performance in both tasks. Moreover, self-reported measures showed that participants were aware of such differences in MWL. Finally, the paradigm’s ecology highlights that task and environmental features may affect the reliability of the various I/E measures. Thus, these factors have to be considered in the design and development of advanced adaptive systems within the industrial context.