The space of the charity or thrift shop is not only a conduit for fundraising, volunteering, and alternative consumption; it is also a complex social environment that includes a variety of paid and unpaid workers. The UK charity retail sector underwent a period of professionalisation in the 1990s, including the widespread introduction of salaried shop managers and assistant managers, typically appointed on the basis of their previous retail experience. Others working in fundraising shops are generally unpaid, including volunteers who are commonly motivated to offer their time because they (a) support the mission of the charity, (b) have spare time, (c) are altruistic, (d) are seeking work experience and/ or (e) seeking social interaction. Social networks can play a significant role in drawing individuals into volunteering, e.g., through family, friends, a place of worship or care centre that has existing connections with the shop, or through social relations established through visiting the shop as a customer or donor of goods. Unpaid volunteers may also include probationers fulfilling Community Service Orders (CSOs) and prisoners on day-release licence, ‘doing time’ in the form of Community Service (CS)1 where these placements have been established in particular localities between Probation and/or Prison services and the charity retail sector (Horne and Maddrell, 2002; Maddrell, 2000). This chapter focuses on Licenced Prisoners’ (LPs) mobilities as experienced in and between the prison and charity shop by centring on a longitudinal study of a managed day-release placement scheme operating through a men’s open prison in the South of England. The data underpinning the study is largely qualitative, including in-depth interviews with LPs, prison officers, and charity shop managers.