Critics have long grappled with the “eccentric, often troubling” nature of Kipling’s fiction (Said, 160): his complicity in and seeming subversion of Imperialist ideologies; his characterization of Indian people, sometimes sympathetic, sometimes superficial and racially insulting; his portrayal of women, misogynist yet admiring. One of the more interesting of these troubling contradictions is his representation of women, especially Indian women. This article investigates the development of Kipling’s representation of Indian women through the cycle of his writing on India: from Plain Tales from the Hills in 1888, to Kim in 1901. The focus is on those Indian women who are central to his stories or novels, who are depicted in other than merely stereotypic ways. Through the fifteen years that lie between “Lispeth,” the opening story in Plain Tales from the Hills, and Kim, Kipling’s last Indian work, Kipling’s narrative representations of Indian women, of India itself, are transformed, becoming both more complex and more illuminating, and revealing a growth in maturity and perception that justifies critics’ claims for Kim as Kipling’s greatest Indian work.