This dissertation is a participant observer’s account of implementing a multisite, randomised controlled trial within Her Majesty’s Prison Service. It adds to a scarce literature detailing the steps involved in implementing experiments in custodial settings by providing a candid account of the route from planning to successful implementation. The randomised controlled trial was designed to evaluate the effectiveness of the Sycamore Tree Programme. This programme’s goal is to teach prisoners the wider harm of crime and includes a face-to-face meeting between a victim of crime and the participating offenders. It derives its rehabilitative potential from restorative justice and seeks to foster hope that change is possible for offenders, thus aiding them to desist from crime. Its development and theoretical basis are described for the first time. In an in-depth narrative the dissertation details how at every stage strategies were developed to manage participant procurement, random assignment, maintaining treatment integrity, and preparing for final outcome measurements. The randomised controlled trial was designed to produce an individual experiment in eight prisons. These will be combined in a meta-analysis as well as analysed as a pooled sample. Overall the implementation process took close to two years and involved a charitable body, Her Majesty’s Prison Service, the National Offender Management Service, and two police forces. This work has demonstrated how the unstable nature of English prison populations and the risk-averse climate must be addressed when conducting experiments in that environment. It has also illustrated the gap between the rhetoric of evidence-based policy and the facilitation of research designed to seek that evidence. Nevertheless, developing trusting relationships and combining rapidly learnt skills with inherent abilities ensured that the evaluation methodology was supported and protected through the various challenges it met. Finally, the dissertation suggests conditions for closer collaboration between government executive bodies and researchers that might increase the number of experiments undertaken in prisons. It also aims to encourage researchers that prison experiments, although not easy, are feasible, defendable, and, above all, worthwhile.