Recent scholarship into the uses of social media has opened up productive ways of thinking about the dynamic relationship between user-generated content and new forms of sociality and social practice. However, compared with Twitter and Facebook, the photo- and video-sharing platform Instagram has received relatively little scholarly attention. Instagram is only the latest in a complex media history that has shaped a range of social practices, including graffiti and street art. This article considers the relationship between street art, graffiti, and mobile digital technologies, in particular the ways in which the production and consumption of forms of street art and graffiti are increasingly shaped by the architectures, protocols, and uses of Instagram. Beyond thinking conceptually about how Instagram is reshaping these practices, it also considers some analytic strategies for Instagram research that can illuminate this emerging and dynamic relationship. We also suggest that thinking of Instagram simply as another tool obscures both the complex issues of using Instagram metadata for research (privacy, the definition of publication, intellectual property, archiving, and conservation) and they ways in which the platform itself is in no way distinct from the cultural formations to which it promises access.