This article details a piece of small-scale action-based research in a school for students with learning difficulties. It focusses on the use of Drama as a means whereby confidence of those students who are at a point of transition to employment can be enhanced. Using qualitative-based mixed methods of data generation, a range of issues are highlighted relating to the challenges for students with SEND moving into employment. The value of Drama activities both intrinsically within a whole school curriculum, as well as a cross-curricular intervention, is also noted. Finally, the article reflects on some of the key opportunities in undertaking research of this kind within a school-based context.