This article discusses R. G. Collingwood's account of re-enactment and Donald Davidson's account of radical translation. Both Collingwood and Davidson are concerned with the question “how is understanding possible?” and both seek to answer the question transcendentally by asking after the heuristic principles that guide the historian and the radical translator. Further, they both agree that the possibility of understanding rests on the presumption of rationality. But whereas Davidson's principle of charity entails that truth is a presupposition or heuristic principle of understanding, for Collingwood understanding rests on a commitment to internal consistency alone. Collingwood and Davidson diverge over the scope of the principle of charity because they have radically different conceptions of meaning. Davidson endorses an extensional semantics that links meaning with truth in the attempt to extrude intensional notions from a theory of meaning. Since radical translation rests on a truth-conditional semantics, it rules out the possibility that there may be statements that are intelligible even though based on false beliefs. Collingwood's account of re-enactment, on the other hand, disconnects meaning from truth, thereby allowing for the possibility of understanding agents who have false beliefs. The paper argues, first, that Davidson's account of radical translation rests on inappropriately naturalistic assumptions about the nature of understanding, and that Davidson commits this error because he develops his account of radical interpretation in response to an epistemological question that is motivated by a skeptical concern: “how can we know whether we have provided the correct interpretation?” Second, that in the twentieth century far too much philosophizing has been driven by epistemological concerns that have obscured attempts to provide adequate answers to the sort of conceptual question with which Collingwood is concerned, namely: “what does it mean to understand?”