The ability to imagine alternatives is crucial in fostering transformed digital futures and challenging the status quo. However, imagining alternatives is challenging, especially in the postdigital era with digital technologies being a taken-for-granted and often unquestioned part of daily life. What kind of interventionist methods could be used to open up possibilities for radically alternative imaginings of digital futures? The chapter introduces two experiments at fostering imaginative capacities to envision alternative digital futures. Grounded in theoretical discussion on imagination, imaginaries, critical agency, and alternative futures, it explores the possibilities and challenges of developing methods that encourage reflection and foster imagination beyond domineering imaginaries of media technologies and their role in shaping human agency. It is argued that supporting the imaginative capacities of everyone could help societies to engage with alternative digital futures and to identify actual means necessary to create conditions for material interventions in and political sensibilities of the world.