This three-part article reinforces crosscurrents between cybernetician Gordon Pask’s work towards creating responsive machines applied to theater and education, and Vygotsky’s theory, to advance sociohistorical approaches into the internet age. We first outline Pask’s discovery of possibilities of a neoclassical cybernetic framework for human–human, human–machine, and machine–machine conversations. Second, we outline conversation theory as an elaboration of the reconstruction of mental models/concepts by observers through reliance on sociocultural psychological approaches, and apply concepts like the zone of proximal development and perezhivanie to Paskian aesthetic technologies. Third, we interpret Pask’s teaching/learning devices as zones of proximal development, and outline how Paskian algorithms in digital devices like THOUGHTSTICKER have been generalized on today’s internet, supplemented by corporate interests. We conclude that Paskian theory may offer understandings of the roles of internet technologies in transforming human thinking, and suggest (re)designing tools incorporating algorithms that contextually advance conceptual understanding that deviates from current indexing approaches.