This article explores contemporary potentials for Illich's 1971 proposal to replace institutional schooling with non-institutional large-scale educational infrastructure, and shows that his visions of deschooling through technology could be embodied on the internet in the form of deschooling virtuality. This conclusion is methodologically restricted in three ways. First, the concept of deschooling heavily depends on one's views to human nature. Second, deschooling society is dialectically intertwined with the concept of conviviality, while deschooling virtuality is based on non-convivial technologies which lead directly to radical monopoly. Third, even the most developed deschooling virtuality might never transform into deschooling society. Despite those restrictions, the article concludes that Illich's deschooling has graduated from mere vision to the real opportunity. Realization of this opportunity will depend on future scientific and social developments and, ultimately, on collective human decision.