Primary-secondary transition can be a period of extreme anxiety for some children, with lowering of self-esteem and confidence. Creative drama has been reported to enhance self-esteem and confidence. This paper explores the possibility of using drama to facilitate successful transition. It focuses on secondary datasets from six primary schools in a local authority in Scotland (357 pupils and 12 teachers) to explore the effectiveness of creative drama. It then reports data collected from four drama professionals to explore whether drama can be effective in facilitating successful transition and the reasons behind that. The data suggest that creative drama can be used effectively in transitions due to its potential to empower pupils, to facilitate an understanding of emotional issues, to provide realistic scenarios with a degree of distance and a safe space to rehearse real life transitions.