In this paper, I will investigate Wittgenstein’s idea about the context-sensitivity of utterance. It is the idea that there is a big gap between understanding a sentence in the sense of knowing the idioms and discerning the grammar in it, and what is said by using it in a particular context. Although context-sensitivity in this moderate sense is a familiar idea in Wittgensteinian scholarship, it has mainly been studied as an idea in “Wittgenstein’s philosophy of language.” However, Wittgenstein’s interest in (...) language is always connected with his interest in the treatment of philosophical problems. Therefore, what is lacking in those preceding studies is the study of the relation between Wittgenstein’s engagement with the idea of context-sensitivity and his philosophical therapy. Therefore, I shall investigate that relation and show that Wittgenstein’s philosophical method cannot be intelligible without taking context-sensitivity into consideration and Wittgenstein’s focus on context is deeply connected with his method for treating philosophers’ “pictures.” Below, I will examine recent debates on grammar, and argue that the standard interpretation is untenable once proper consideration is given to context-sensitivity. Next, I will argue that context-sensitivity is important because it gives us a good grasp of the process of a philosopher’s being caught in a picture by citing the discussion about mental process and about the Augustinian picture and rule-following in Philosophical Investigations. Finally, I will talk about the significance of my interpretation for contemporary arguments about philosophical methods. (shrink)