This research explores whether the co-design of provocative prototypes with older adults can scaffold critical thought concerning ethics, trustworthiness, security and privacy of age-oriented Internet of Things (IoT) products and services, and associated data-driven technologies (DDT). By inviting 15 adults defining themselves as ‘experiencing or anticipating old age’ to co-design IoT and DDT which addressed their hopes and fears for the future, we encouraged them to imagine a revolution in ‘technology for aging’. Three workshops utilized theatre and design research approaches including speculative design (Dunne, 2013) and co-design of provocative prototypes and social design fiction (Pilling, 2019), to stimulate discussion around imagined futures for aging and technology. Participants modelled the internet as they understood and imagined it. They were then introduced to sensors, actuators and machine learning through interactive demonstrations. Four randomly formed groups ideated ways these technologies could be applied to earlier identified hopes and fears for the future of aging. Creative technologists then created prototypes of these ideas over two weeks of feedback and iteration with participants. Participants wrote and performed performances incorporating these prototypes, which explored cybersecurity and cyberharm (Agrafiotis, 2019). Six participants also partook in post-workshop semi-structured interviews. Methods developed in this research scaffolded critical thought concerning the ethics, trustworthiness, security and privacy of age oriented IoT, and associated DDT, regardless of experience or existing knowledge. Participants found it easy to interrogate the ethics, privacy and security of their speculations because, while they may not have been technically scalable or feasible, they understood them.