This chapter explores the complex area of working with patients who experience relational difficulties and who may function predominantly at a borderline level of psychological organization. These patients are influenced by early traumatic experiences, which can shape the therapeutic encounter. They often don’t have the kind of early experience that enables them to develop the capacity to recognise feelings and to know that they are not dangerous, that they are bearable, and will pass. Acts of self-harm are frequently a response to manage unbearable feelings. These and the experience of suicidal thoughts can be understood as a wish to get rid of these feelings. The nature of self-harm and what it evokes in the clinician are discussed. Individuals with these difficulties have often experienced a lack of a consistent and containing other and can enter crisis in response to experiences of rejection or threats of abandonment. This is important both during therapy but particularly when ending the therapy. If we understand what underpins the relational difficulties that these patients have, we can take them into account in the therapeutic work. Some adaptations of technique when working with patients with borderline level difficulties are considered.