The question of the genre of The Kolyma Stories continues to perplex readers: the tales resemble fiction and are at the same time intended to serve as document, evidentiary proof of the evils of Stalinism. In this article I reconsider Walter Benjamin’s “Storyteller” essay, arguing that Shalamov is, in significant ways, a Benjaminian storyteller, updated to catastrophically unfree conditions minus any nostalgic lens. Taking Shalamov’s prose not just as document and fiction, but more specifically, as document and story allows for a deeper understanding of his creative process, aesthetics, and how his prose is intended to act on the reader. Shalamov becomes a storyteller in part to break free from what he saw as the didactic tradition of the Russian novel. I compare Benjamin’s notions of storytelling to Shalamov’s concepts of “new prose,” and then scrutinize Shalamov’s contradictory stance on whether his stories contain “lessons” (advice is central to Benjamin’s framework). I touch on the fusion of document and folktale in several stories, referring to Vladimir Propp’s Morphology of the Folktale. Finally, I examine “Galina Pavlovna Zybalova” (1970–71), which, I argue, demonstrates how skazka and story function in relation to memory and advice.