Self-harm is a pervasive symptom of emotional distress written on the body. It has become a common clinical presentation for Counsellor’s who work with Adolescents with many challenges attached to this type of work. The aim of this study is to explore counsellor’s experience of working with adolescents who engage in self-harm whilst investigating the role of the therapeutic relationship, the therapeutic response to self-harm and the exploration of the use of transference as a therapeutic instrument. The sample chosen was five experienced counsellors from a multi-disciplinary team who all work directly with Adolescents who engage in self-harm. The process of thematic analysis was applied to the data, representing a qualitative method of research. Three subordinate themes emerged from the analysis 1) The counsellor’s capacity 2) Containment 3) Transference. These themes were discussed extensively and the author gained insight into the challenges that counsellors experience in the therapeutic space, and their capacity to understand and tolerate the uncertainty that self-harm evokes, due to the provocative nature of such a presentation. Containment was found to be main function of the therapeutic relationship by providing a space to discard the nastiness of self-harm with the knowledge that it is safe and secure. It was evident that the counsellor’s emotional reaction to self-harm was of significant importance in relation to managing the transference between the counsellor and the adolescent.