This article draws on the theories of Mezirow, Foucault, and Holland and colleagues to investigate how students were positioned in relation to their own experiences, what opportunities they had to overcome their negative positioning in relation to the power structures that inform the worlds in which they move, and how their changed practices impacted on their positional and figured worlds. Data from community- and prison-based participants in Scottish adult literacy projects are used to interrogate the factors that contributed to overcoming the negative discourses that students had been embedded in. This article concludes that by the end of their programs, the students had experienced transformative changes in their learning identities, and these changes encompassed cognitive, emotional, and social dimensions.