Shirley Jackson’s fiction presents an expansive catalogue of female characters who find themselves in eerie predicaments that they negotiate in interesting ways. This thesis explores the presentation of female characters in these predicaments. What roles do the female characters play in the stories they inhabit? What modes of escape do they employ from their predicaments? What makes their situations fundamentally anxious? To explore these questions, I examine the roles ascribed to female characters and their various responses to them. I inspect Jackson’s use of the ghost story and the fairy tale and the ways in which she engages with characteristic tropes to explore female agency. I interrogate anxieties about the self, and examine how these anxieties haunt many of the stories through their presentations of the female protagonists. These anxieties play out in the spaces that form and deform possibilities for women – the home, the suburb, the city – and through their allotted roles as wives, mothers, daughters, women alone. This study hopes to illuminate the entropic and anti-entropic nature of Jackson’s female characters: women variously unhinged by their roles or grounded by them. These women produce diverse reactions to oppressive situations as they negotiate their restrictive circumstances that simultaneously anchor and imprison them.