This chapter raises some questions about assessment practices when learning outcomes are fuzzy and learning settings are messy: when learning is ‘in the wild’, as David Perkins suggests. Classrooms and early childhood settings are examples of ‘wild’ and complex contexts that ‘present a wilderness of vaguely marked and illdefined occasions for thoughtful engagement’ (Perkins et al., 2000: 270). Solving problems, taking action and interacting with others in these contexts calls for more than knowledge and abilities. The inclination to ‘follow through’ on intentions, and the capacity to notice, recognize, use and create opportunities to do so, are also key requirements. An abilities-centric view of intelligent performance can prevail in a testing situation or a worksheet where the task is prescribed and the criteria for success are clearly marked, but interesting situations are not usually like this and, as Perkins and his colleagues point out, the task of exercising one’s intelligence ‘in the wild’ is ‘strikingly different’. Assessment in the wild calls for complex analysis that includes interpretation and recognition of significant events and opportunities. This is true for both teachers and learners. Perhaps some classrooms are less wild than others, but an appropriate, and indeed, an urgent, educational task is to assist young people to be prepared for the diversity of twenty-first century wildernesses that they will encounter, as well as to learn in the complex situations of their current lives.