The rise of online learning over the past few decades has raised fundamental questions about the kinds of "spaces" and "places" this mode of education creates. Do they support meaningful exchanges? Can they advance educational equity, access, and community-building? Are they comparable to in-person classroom experiences? The recent COVID pandemic and the global turn toward virtual learning in response have brought such questions into sharp relief. These were the questions and contextual factors that brought distinguished historian Carroll Pursell and international educational technology authority Toru Iiyoshi together for this policy dialogue. Their conversation takes readers on a wide-ranging discussion about the interplay between education, technology, and society writ large. And they offer insights into the past, present, and likely future of education in an era of accelerating technological change. Carroll Pursell is the Adeline Barry Davee Distinguished Professor of History (Emeritus) at Case Western Reserve University and Distinguished Honorary Professor of History at the Australian National University. He held faculty positions at the University of California at Santa Barbara and served as the Andrew W. Mellon Distinguished Professor of the Humanities at Lehigh University. Pursell is a fellow of the American Association for the Advancement of Science (AAAS), and former president of both the International Committee for the History of Technology (ICOHTEC) and the Society for the History of Technology (SHOT), which also awarded him its Leonardo da Vinci Medal for outstanding contributions to the history of technology. Toru Iiyoshi is professor and director at the Center for the Promotion of Excellence in Higher Education at Kyoto University. Previously, he was a senior scholar and director of the Knowledge Media Laboratory at the Carnegie Foundation for the Advancement of Teaching. He also served as senior strategist in the Office of Educational Innovation and Technology at Massachusetts Institute of Technology. Iiyoshi is a member of the World Economic Forum's Global Agenda Council on Technology and Education and past recipient of the Outstanding Practice Award in Instructional Development and the Robert M. Gagne Award for Research in Instructional Design from the Association for Educational Communications and Technology. "HEQ" Policy Dialogues are, by design, intended to promote an informal, free exchange of ideas between scholars. At the end of the exchange, we offer a list of references to readers who wish to follow up on sources relevant to the discussion.