By attending directly to Henry Miller’s fiction and associated biographical material, this paper explores Miller’s writing impasse and subsequent developmental and artistic implications. The paper pursues such interests by dedicating attention to Miller’s idealized identification with other writers and particularly Fyodor Dostoevsky. Interpretations of this identification are made possible by the deployment of several psychoanalytic concepts, which assists in understanding the associated dynamics as well as the subsequent relenting of Miller’s writing impasse. With these interpretations in place, the article then advances on applied psychoanalytic intentions and explores the psychogenesis of Miller’s Tropics and Rosy Crucifixion trilogies.