How do we learn/teach knowledge of a space/place? “[AI]stanbul: Schooling the Machine” tackles the process of learning and teaching of a new place by employing Artificial Intelligence. [AI]stanbul is a machine that wants to ambitiously learn about Istanbul. It acquires and appropriates place-based experiences through interactions with visitors/participants. The conversations take the form of both natural language and image-based interactions all of which are tied to an Istanbul map. [AI]stanbul collects and interprets data that relate to broader categories of personal memories, components of daily life, transportation, places to visit, along with a “wish box” that collects what people long for through responding to a number of questions from the ever-expanding list. The installation aims to discover the rather elusive knowledge of a city by “borrowing experiences.” The role of student and teacher is in flux: the machine and visitors/participants learn from each other about life in Istanbul.