Work routines are integral to prison life. One recent development, at the behest of the government, especially in privatised prisons, has been the contracting out of work by private companies to prison. This type of work is usually organised under the guise of rehabilitation, employability and skills development to help offenders enter the labour market upon release. This thesis aims to provide an insight into the experiences and everyday existence of what I term ‘orange-collar workers’ - prison inmates who carry out privately contracted work in a prison setting. The research uses an ethnographic approach to explore this phenomenon; forty semi structured interviews were conducted as well as participant and non-participant observation in a private prison, Bridgeville. The themes that developed through the fieldwork included boredom, unskilled work, humour, masculinity and hierarchical structures within the workshops. The discussion of these themes illustrates the mundanity, the lack of skill and the particular culture in the orange-collar workshops which is not conducive to rehabilitating prisoners as it does not acclimatise them to a real work environment. It is found that orange-collar work does very little in terms of rehabilitating prisoners. Instead, it merely provides them with the immediate benefit of keeping busy which is considered better than the alternative of being ‘locked up’. With regard to rehabilitation, the primary triumph of orange-collar work is preparing prisoners for low-skilled, low-paid work, dominated by hierarchical conflict, little autonomy and few prospects - the characteristics of the work most likely to greet them on release. This serves to reinforce their antipathy to the mainstream world of work and (coupled with their exposure to alternative avenues of earning money in criminality) only discourages many prisoners from entering legitimate employment. But prisoners admire the private firms who are utilising their labour. They respect the ability to make money by whatever means necessary and they see exploitation as part and parcel of economic success.