Our proposal, “Islands in the Sky: Scenario Planning for Uncertain Future Contexts”, is an interactive digital poster which invites attendees to explore, and try their hands at, scenario planning in the tradition of the Oxford Scenario Planning Approach. This approach invites users to explore the imagined future contexts which their plans, strategies, acts, and architectures may have to inhabit. We look not at solely what is possible, probable, desired, or expected, but at plausible futures which lie in current blindspots and which challenge assumptions about what is emerging in the situations we inhabit.