In this dissertation, I use critical discourse analysis to identify the material and conceptual barriers that prevent women who are reintegrating into the community after periods of incarceration from becoming 'employable'. Employability, as conceived within this dissertation, is a subject position toward which reintegrating women are directed. Yet while they are directed toward this, 'employability' is conceptually incompatible with the ways the needs and abilities of 'criminalized' women are characterized through correctional discourse. Drawing from in-depth interviews with twenty-one reintegrating women and thirteen service providers, I identify the contradictions within the discourses that describe reintegrating women, and which proscribe and constrain their possibilities for reintegration. I offer a contribution to the scholarship of the past three decades that has queried, monitored and challenged practices and policies relating to women's corrections in Canada. Feminist efforts to identify women's pathways to crime, efforts which emphasize women's social, political, and cultural contexts, have been incorporated into correctional discourses that shift the emphasis from women's experiences, to the emotional and psychological impacts of those experiences. This serves to individualize structural problems. I probe the expressed rationales and practices of employment support for reintegrating women, and more importantly, examine how women navigate and respond to these supports and the discourses which sustain them. I find that the discourses which surround and support certain subject positions for women, discourses which are mobilized by adjectives such as 'criminalized', render elusive women's emancipation and redemption. I believe it is imperative to recognize the intersectional contexts of reintegrating women's lives and experiences. There is also a need to recognize the conceptual limitations of subject positions which are generated and mobilized through current discourses about women's criminalization, incarceration, and reintegration.