Teachers are challenged to adopt practices that facilitate the development of “necessary” skills and strategies for learners. For many, however, what is required in policy and curricula is increasingly obscured and even confusing as teachers are bombarded with jargon prescribing seemingly similar (yet apparently different) approaches such as “rich tasks”, “big questions” and “fertile questions” that are to be “relevant”, “authentic” and “engaging” for the learner. Barton and Hamilton (2000) argue that literacy learning should take the learner beyond the transmission of technical skills in the classroom to an understanding of its role within a community’s cultural practices. These literacy practices (Street, 1995) are mediated by literacy events (Heath, 1983) and it is engagement with these events and their diverse demands that allows learners to make strong connections to their own literacy practices. Reported in this paper are the interpretations of four experienced primary school teachers as they plan, program and facilitate authentic literacy experiences in their classrooms. These are examined within the framework of the principles of authentic learning (Herrington & Oliver, 2000), which is useful in gaining insight into the ways that experienced teachers make sense of the complex jargon associated with their profession for the development of deep and flexible knowledge that can be applied in a range of community settings. Evident in these teachers’ stories are the understandings, beliefs, contexts and competing tensions that underpin the conceptualisation, design and implementation of these experiences. The teachers’ stories reveal the complexity of teaching as they consider: - the individual contexts of their schools - their students’ own communities - the expectations of stakeholders in a child’s education - the availability of resources.