The paper develops a novel account of the nature and genesis of some philosophical problems, which motivates an unfamiliar form of philosophical criticism that was pioneered by the later Wittgenstein. To develop the account, the paper analyses two thematically linked sets of problems, namely problems about linguistic understanding: a set of problems Wittgenstein discusses in a core part of his Philosophical Investigations, and the 'problem of linguistic creativity' that is central to current philosophy of language. The paper argues that these problems are generated by tacit and unwarranted presuppositions at odds with warranted beliefs the philosophers raising the problems reflectively hold at the same time. For a rigorous conceptualisation of this phenomenon, the paper develops the notion of a 'philosophical picture' first proposed by Wittgenstein, and specifies the particular class of philosophical problems that may be raised due to adherence to such pictures. The results motivate a new form of philosophical criticism: the systematic exposure of relevant philosophical pictures, and efforts to overcome their tacit influence on philosophical reflection.