This programmatic paper is an attempt to connect some worries in the philosophy of language with some traditional views in artificial intelligence. After a short introduction to the notion of context in philosophy (§1), starting from the inventor of mathematical logic, Gottlob Frege, I list three debates in the philosophy of language where the solution is strongly undecided: §2 treats the debate between holism and molecularism; §3 describes the debate on the boundaries between semantics and pragmatics; §4 hints at a solution of the debate between explicit and implicit view of incomplete descriptions. These debates may be considered case studies on what is happening to the notion of context in philosophy in the first two decades of XXI century; they push us to look for a unifying framework in which to frame those worries: I propose to shift the attention towards a representation of the basic abilities required to navigate across contexts (§5). In the conclusion, I use some suggestions from computer sciences as a contribution towards a better definition of what is meant by “pragmatic competence”, strictly connected to the philosophical enterprise (§6).