The present paper examines a type of sceptical hypothesis put forward by Adam Carter that specifically targets understanding—the Confusion Hypothesis. After clarifying the nature and scope of that hypothesis, it discusses Carter’s favoured virtue perspectivist answer to the challenge it raises. It is argued that this answer is ultimately unsatisfying as it is unable to explain how a subject can obtain assurance that her grasp of a given body of information actually results from the competences she comes to appreciate as (...) being reliable. A different answer that relies on the practical dimension of the specific grasp involved in understanding is then offered and is shown to avoid the problems faced by Virtue Perspectivism. (shrink)