This chapter explores the methodological challenges of studying future imaginaries in education and introduces a revised model of future workshops to address these difficulties. Based on workshops with representatives from the EdTech sector, research institutions, and educational policy organizations in Sweden and Estonia on the theme ‘The Classroom of 2040’, the study examines the interplay between sociotechnical imaginaries, collectively held visions about how (new) technology can solve current problems and contribute to societal progression, and the participants own imaginations about what the future of education could or should be. The workshops facilitated a process that moved from a mapping of dominant educational imaginaries to critical reflection and the co-creation of alternative, postdigital futures. This approach can be used to understand how sociotechnical imaginaries are materialized in educational technologies and policies while also revealing the tensions and negotiations involved in this process. By engaging influential stakeholders from the EdTech and education sector, the workshops model also highlights the potential of experimental and participatory methods to facilitate dialogue and collaboration between different actors that can inform future development in education.