According to the Situational Context Theory, the recent accelerated evolution of digital technology (IoT, Microchips) reinforces the trend of progressive reduction of the physical distances between an ‘Augmented individual’ (technology-empowered subjects playing their daily life decision-making processes based on multidimensional choice-sets) and technology. Technology becomes further more competent than the subject in dialoguing with the situational environment, both in the area of information building (search engines) and of location-based dialogue with the daily environment (IoT, NFC, VR). Because of reduced physical distances and the growth in competence of technology, the free-choice based subject’s responsibility, which initially appeared ‘augmented’, in reality decreases and becomes an illusion, quite as the cubism illusionism of Braque and Picasso painting. Indeed, in this frame of work, responsibility appears to shift from the augmented individual to organisations and institutions managing technology with competence, within a frame of a digital technology Corporate Social Responsibility.