The complexities in Rudyard Kipling's Letters of Marque have previously been read as manifesting the contradictory nature of his relationship with native India. This article demonstrates that Kipling's writing could be far more precisely located, and its ambiguities more deliberate and functional, than such observations would suggest. By reading the Letters alongside two examples of the Indian fiction, this article explores how they mark the stage at which Kipling began using his narratives to communicate with a particular Anglo-Indian ideological milieu, promoting their perspective and no longer cultivating the ambiguities which had energized some of his darker, earlier work.