As the rules of social engagement and hierarchy become less clearly defined in online spaces (Dubrovsky et al., 1991, Joinson 2002), so authority becomes an increasingly tricky notion in online teaching. In addition, unstructured digital spaces (wikis, live chat, virtual worlds) have great potential as sites of learning, connection and construction of meaning and self (Turkle, 1995), but the teacher's capacity to control or regulate these spaces is limited (Land and Bayne, 2006). Indeed, we argue the tutor's role in such a space is not to regulate, but rather to participate and provoke in creative and playful ways that open up passages or possibilities in chaotic online spaces.