Whilst popular visions of Artificial Intelligence (AI) are often presented through the lens of sentient machines, our lived experience of AI is more mundane and exemplified by so-called ‘smart’ products and services. Whilst this mundane reality is often presented using design approaches that make their operation appear simple and innocuous, these smart systems, and the data they use and collect, can challenge and even disrupt ordinary expectations. Our ability to manage smart technologies effectively is key to the field of Human Data Interaction (HDI), which seeks to shape systems design and empower users by implementing core principles of legibility, agency and negotiability. However, how these principles manifest in practice is yet to be fully understood. We seek to understand key challenges confronting HDI by situating smart products and services in everyday life and creating a mundane experiential future that houses AI in a caravan for evaluation with the general public.