This paper examines the idea of Wittgenstein as a philosopher of context in the light of his preoccupation with seeing connections. The importance of this is considered in relation to more deductive and inductive forms of reasoning, unduly constrained notions of what it is to follow a rule, and ideas of defining characteristics and identity. The implications of contextualist views are examined, as well as the consequences of the application of the familiar lumper-splitter distinction, which emerges originally in disputes in the taxonomical sciences. The relation between seeing connections and imagination is brought to the fore. The paper provides further reason to challenge dominant conceptions of assessment in education and their pervasive effects on curricula.