This study explored in depth the factors that trigger Specialist Trainees’ reflection and why documented evidence may not always encapsulate their practice. Specialist Trainees in the UK are required to record reflections on their clinical experiences and evidence of their professional development in an e-portfolio. Fifteen qualitative semi-structured interviews were undertaken. Semi-structured interviews were conducted with first year general medical Specialist Trainees in one Deanery in the North of England. Thematic framework analysis of the qualitative interviews generated categories. Four categories emerged from the qualitative data analysis: help/hindering forces; strategic and superficial entries; triggers for reflection; and the role of others, including Educational Supervisors. This study identified clear triggers for reflection but the art of writing it down often seems superficial, sometimes hurried, sometimes selective and often strategic. There is some evidence from this series of semi-structured interviews to suggest that reflective entries are limited by time constraints and also privacy concerns regarding the reliability of security systems within the e-portfolio. Findings suggest that the e-portfolio, in its current form, may not be the most appropriate way of encouraging written accounts of reflective practice.