A key topic in criminological research relates to desistance, understanding why and how offenders transition away from criminal thinking and behaviour. Several theories of desistance and models of rehabilitation highlight the importance of education and work in this process. This research acknowledges the interconnected nature of these two domains by exploring the foundational attributes of education, literacy and numeracy, and the role of these skills in the context of prison work experiences. The data used come from two sources: the Programme for the International Assessment of Adult Competencies (PIAAC) Survey of Adults Skills which was given to nationally-representative samples of incarcerated and household adults and a sample of North Carolina Correction Enterprises (NCCE) inmate employees. The aim is to evaluate prison work experiences, both generally and in the specific context of prison industry work, with regard to the opportunities they offer for cognitive skill use and development. Two facets of literacy and numeracy are addressed in this research: the skills one uses, in this case specifically as part of their job, and the skills one possesses as measured by an assessment. First, instruments of reading, writing and numeracy skill use among incarcerated and household adults are constructed and validated using the Rasch model. Differential item functioning tests across groups of inmates and household adults are employed to critically evaluate the utility of instruments developed for the free labour market context for accurately describing the realities of prison work. Then, individual estimates of skill use are compared across sample groups and occupational industries using one-way and two-way analysis of variance tests (ANOVA). Examining these differences provides evidence for how the prison environment constrains skill use for workers employed in some of the most common types of jobs. However, inmates in some occupations, such as the NCCE workers and inmates employed in education, social service or health and personal care jobs, report similar levels of skill use to household adults in the free labour market. Finally, the research examines how assessed literacy and numeracy proficiency relate to estimates of skill use in the work environment and to a range of other socio-demographic and dispositional variables. Correlation analysis reveals a skill use and proficiency mismatch for incarcerated adults compared to household adults; there is no relationship between these practices in their prison jobs and their assessed proficiency. Additionally, factors associated with educational attainment, attitudes toward learning, race and age are all significant in models of incarcerated adults' assessed literacy and numeracy. The interpretation of findings includes a theoretical discussion of key topics from the thesis as they relate to Pierre Bourdieu's concepts of practice, capital, field and habitus. In addition, there is consideration of how results contribute to the applied study of literacy and numeracy in samples of both incarcerated and household adults and the evaluation of prison work experiences. I present a critical appraisal of the frameworks that guide skill-related surveys and assessments for incarcerated adults and present suggestions for future versions of such surveys. This research provides a look inside the "black box" of prison work experiences by describing the extent to which inmates used cognitive skills in these positions and illuminates the connections between such behaviours and assessed literacy and numeracy of incarcerated adults.