In this paper, a design experiment using Instagram as a cultural probe is submitted as a method for analyzing the challenges that arise when considering the implementation of social media within a distributed communication space. It outlines how small, iterative investigations can reveal deeper research questions relevant to the education of emerging design students choosing to enter the field of mobile communication design. Challenges of participatory design, media affordances in relationship to established taxonomies and sustainability are all a result of this research-driven design experiment.