To integrate digital technologies into the curriculum, teachers must support learners to use digital tools in authentic contexts. Physical computing, which involves the use of small portable electronic devices, provides an opportunity to achieve these goals. This article reports on the initial stages of a design-based research (DBR) project that will enable students to monitor and investigate their own learning spaces, with a focus on the impacts on their own well-being, and to propose solutions to any issues that they identify. The study focuses on a series of workshops, run with staff from an educational organisation, designed to explore environmental monitoring in the classroom and identify opportunities to apply the theory of situated cognition to authentic learning in context. The article reports on the first two phases of the DBR approach, defining the project focus and understanding the problem, to propose and refine a set of five design principles. The insights gained will be used in the subsequent phases of the DBR process.