In the late 1990s, the Department for Education and Employment in England set out to motivate and engage teenage students who were said to be 'disaffected' with the traditional school curriculum. Jerry Wellington, Professor of Education at the University of Sheffield, and Pam Cole, research fellow in the University of Sheffield School of Education, were asked to evaluate one of the 21 projects that were set up across the country. The pupils involved were partially disapplied from the National Curriculum in order to follow a work-related scheme set up by two schools, a Chamber of Commerce and a local Learning and Skills Council. In this article, Jerry Wellington and Pam Cole explore some of the difficulties that accompany evaluation, and particularly a review of the impact of interventions involving so-called 'disaffected' pupils. They describe some of the practical and methodological difficulties faced in such an evaluation, as well as highlighting the positive aspects of the task. They reflect on a range of unforeseen and unpredictable dilemmas that faced them in this work, and note some of the interesting significant strengths that developed from the project. At the end of their article, Jerry Wellington and Pam Cole summarise what they have learned from the evolving methodology of this evaluation and present a case for increased levels of collaboration, between practitioners and researchers and between professionals and pupils, in future projects of this kind.