Designing with the community brings about a number of benefits, including tacit and contextual knowledge about the problem domain; this is especially apparent in rural settings. However, designing for problems that have yet to embed themselves in the fabric of society (i.e. future problems) poses a number of challenges, as they typically present intangible scenarios and concepts that have yet to be experienced by the wider-community. Using the OnSupply project as a case study, we share our experience in working with the Tiree community to address a future problem through a technology-mediated enquiry. Furthermore, we present a novel process that uses creative workshops augmented with physical artefacts to inform and learn from the community about a problem space, and to seed the design of a system that addresses it.