“The Purloined Letter” is the third of the three Dupin stories that Edgar A. Poe wrote and published in 1844. Contrary to being a typical example of detective fiction which usually involves an investigation to find out what is being kept hidden, “The Purloined Letter” is rather concerned with finding out what is being kept in plain sight. Dupin’s familiarity with logic, math and physics enables him to look at the matter at hand from an exceptionally distinct perspective. Unlike the chief police officer of the Paris Police Department, Dupin firmly believes that the purloined letter has never been concealed at all. To prove his point, he emphasizes the ability to identify with the opponent and draws an analogy from a game of guessing in which one player is expected to make a correct guess about what the other player is thinking of. Dupin also makes a philosophical point regarding the failure of human mind to notice the obvious, which is a result of its tendency to believe that it can find the obvious in minute details. Dupin also believes that the only way to obtain the letter is to purloin it back from the robber who purloined it. And hence he purloins the letter in almost the same way as it was first purloined. The purloining of the letter is mirrored in the re-purloining of it. In the light of all this, this paper aims to discuss and resolve the moral ambiguity which surrounds Dupin’s identification of himself with the robber and his consequent purloining of the letter in exactly the same way as the robber has previously done in order to recover the purloined letter from the hands of the robber.