In this article, Larry Cuban discusses his ideas about the topic of this Special Issue of E-learning and Digital Media "Networked Realms and Hoped-For Futures: A Trans-Generational Dialogue" with one of its co-editors, Petar Jandric. The conversation explores the historical relationships between education and information and communication technologies and draws lessons for present and future. The first part of the conversation explores methodological issues pertaining to historical thinking about schools and computers in the network society. It identifies a continued need to recognize historical patterns, including those in thought experiments, and shows that Rogers' theory of diffusion of innovations should be supplemented by more nuanced approaches to the historical relationships between schools and computers. The second part of the conversation presents an attempt to explain historical patterns using the ancient notion of magical thinking. It explores why teachers use computers in their private lives much more than in their professional lives, and "school anarchy" caused by student usage of personally owned devices in classrooms. It creates a baseline for comparison between desktop / laptop computers and various hand-held devices, and dismantles the quest for deschooling as another example of magical thinking. The third part of the conversation examines the ideological role of information and communication technologies in contemporary school reform and explores their potential for democracy. It analyses the contemporary transformations of traditional publishing formats such as books, journals and newspapers, and their reflections in the world of academia. It examines the changing role of teachers as public intellectuals, and the role of information and communication technologies in their public exposure. The last part of the conversation analyses the process of "educationalizing" various social and economic problems, and links it to contemporary technologies. It revisits Larry Cuban's predictions from "Teachers and Machines: Classroom Use of Technology Since 1920" (1986), and reminds us that accurate predictions are rare, while inaccurate ones are not only common but often memorable. Finally, it examines why it is so hard to balance education with information and communication technologies.