The paper describes a study of the contexts of six teams, expert in research and development of digital media for learning mathematics, who cross-experimented in classrooms with the use of each other's artefacts. Contextual issues regarding the designed tasks and technologies, the socio-systemic milieu and the ways in which the researchers worked with the teachers were in focus. We analysed the ways in which a set of mutually constructed and negotiated questions aiming to illuminate otherwise tacit contextual issues operated as boundary objects amongst the teams. We discuss the need to develop special tools such as these boundary objects in order to elicit issues of context and the ways they may affect the production of theory.