This chapter focuses on how participatory speculative design was set up within the context of healthy ageing in Malaysia. Four workshops were developed and implemented with a range of stakeholders, from senior citizens to technical experts involved in the development of technologies and policies on ageing and health. The participatory workshops led to the development of a few emergent prototypes by the researchers as proof of concept. At the same time, the workshop unearthed a number of challenges involved in introducing speculative design as participatory approach for tackling present problems with policy implications, ranging from the localised context of policymaking to participants’ readiness.