In 1971, Ivan Illich called for shifting away from the traditional concept of schooling. To replace traditional schooling, he proposed creating a large-scale, non-institutional educational infrastructure. This infrastructure would be empowered by the information and communication technologies (the first microprocessor was invented the same year in Silicon Valley). The educational infrastructure he proposed, the ‘learning’ (Illich 1971: 72) or ‘educational web’ (77), would consist of four interlocking educational networks to enable learners to achieve their own goals. The first educational network would develop around a directory of educational resources, freely available to learners (Illich 1971). For example, the directory would allow learners and educators to reserve libraries, laboratories, museums or theatres as well as to visit factories, airports or farms as apprentices or in off-hours. The second network would develop around an open directory of people who would list ‘their skills, the conditions under which they are willing to serve as facilitators for others who want to learn these skills, and the address at which they can be reached’ (Illich 1971: 79). The third network would develop around a platform in which people would describe the learning activities they are interested in, with the aim to find other learners who may wish to collaborate. The fourth network would build on a directory of professional educators, who would detail their qualifications, services and the terms on which these are made available (Illich 1971). After five decades, one may say that Illich’s vision is embodied in initiatives such as the Khan Academy or the P2P University and even share Hart’s view that ‘Illich predicted the World Wide Web’ (Hart 2001: 72; Jandrić 2014). However, the idea of deschooling proved to be wishful thinking (Cuban and Jandrić 2014). Schools are still around and education remains considerably institutionalized. But this ‘large scale educational infrastructure’, the Internet and the Web, has catalyzed the emergence of postdigital phenomena, which may ‘influence power and offer individuals and communal settings the potential for alternative vernacular practices to emerge in culture’ (Atasay 2013: 58). With this article we wish to tell a story of an emerging phenomenon that may offer insights towards realizing some of the goals and values underpinning Illich’s vision of deschooling society. Our aim is to cast a radical educator’s eye over ‘cosmolocal production’ or ‘cosmolocalism’ (Schismenos et al. 2020). Cosmolocalism emerges from technology initiatives that are small-scale and oriented towards addressing local problems, but simultaneously engage with globally asynchronous collaborative production through the commons. Next section introduces the concept and praxis of cosmolocalism. Then, we describe two educational scenarios we have designed and implemented. The goal is to demonstrate how educators, practitioners and scholars could use elements and lessons from cosmolocalsim to facilitate a shift from ‘deschooling virtuality’ (Jandrić 2014) to deschooling society. We conclude with challenges and opportunities for future research and action.