Social media’s ubiquity is transforming contemporary education. Students inhabit classrooms with connected devices, streaming data, chatting on personal messaging and sharing information with invisible audiences. The academic curriculum is challenged not only by social media resources, but also by novel, complex practices of producing, organising, evaluating and distributing knowledge. Some have taken the emergence of these connected learning environments as questioning the very need for a physical classroom. We seek to unpack the dynamics that social media generate in academic teaching, thinking and learning without severely compromising the pedagogic impulse. Consequently, this chapter begins with a look at the rapid rise and even faster decline of massively open online courses (MOOC) with the aim of identifying some of the pitfalls for attempts to rethink higher education in the light of social media. The second part of this chapter proposes that the classroom was historically constructed with and in relationship to technologies of knowledge production, thus questioning the dissociation between the pedagogical practices and technological conditions of learning. This leads to an exploration of some of the modes of engagement in user-generated content platforms, which have potentially fruitful resonances in higher education knowledge infrastructures and pedagogy. We explore this by examining Wikipedia, then look at conditions of speech and assessment through the lens of Bulletin Board Systems, examine registers of sharing and labour through Facebook, and reflect on content curation through Twitter. The third and final part of the chapter argues that analysing and conceptualising social media can become a test bed for experimental knowledge in management education.