This chapter describes a collaboration between its authors – a professor and an undergraduate (post-secondary) student – to develop an education programme for Play the Knave, a mixed-reality digital Shakespeare game. As part of an effort to bring the game to local elementary and secondary school English classrooms, the authors co-ran an internship programme at our university, where the game was created. Interns, most of whom were English majors interested in education, learned to create and then teach lesson plans for Play the Knave, subsequently researching the game’s impact on learning. Our chapter discusses the challenges of collaborating in a university environment, comparing these to the challenges players experience when interacting with avatars in Play the Knave. Like Knave’s players, participants in our programme faced difficulties connecting with other participants, including ourselves and local teachers. We maintain that flawed connection – which players of digital games describe as ‘glitchiness’ – need not undermine effective collaboration but can actually enhance it, as participants are pushed to adapt constantly to shifting circumstances. In contrast to theories of artistic collaboration that prioritize participants achieving a state of ‘flow’, we argue that, in fact, collaborations can be most successful when marked by fits and starts, lags and the imperfect connections endemic to living in a digital world.