This report seeks to investigate a key intersection of academic and practical learning in social work training: the assessment of students on placement and the challenges for practice-based assessors in assessing a failing student. Department of Health (2002) requirements for social work education require that students spend at least 200 days in practice learning (in at least two settings); gain experience of undertaking 'statutory' social work tasks (involving legal interventions); and provide services to at least two different service user groups. These practice placements are assessed by practice educators, either placed within organisations, or by independent assessors. Whilst academy-based social work educators generally have recourse to such support mechanisms as collegial discussion, opportunities for moderation and codified assessment procedures when making assessment judgments, the experience of the practice assessor is potentially more isolated – and certainly less well documented. What are practice educators’ experiences and views of the ‘challenging’ or ‘failing’ student on social work placements? What strategies have proved productive in supporting a failing student and what outcomes have educators observed? The present study seeks to answer these questions and to capture and codify some key principles and practices accordingly. In line with recent discussions and concerns within the profession regarding assessment of social work students on placement (Basnett & Sheffield, 2010), the study proffers a sustained and specific focus on the experiences and perceptions of practice educators (PE) to determine their views of the ‘difficult student’, and their sense of the support they require from academic colleagues in order to reach judgments and to implement interventions.