The chapter will dive into the topic of confrontations as a tool to work with alliance ruptures. It includes practical suggestions for clinicians for bringing up alliance-related problems and issues that may threaten alliance with their patients. As an illustration, the chapter will present a case that revolves around a critical alliance rupture with an older patient showing challenging interpersonal behavior in the inpatient setting. The patient–therapist dialogue will be used as a springboard throughout the chapter to extrapolate clinical guidelines of confronting alliance ruptures and making them easy to understand and apply. At the end of the chapter, the follow-up on the case demonstrates the possibilities of positive long-lasting impacts of confronting alliance ruptures. Practical examples and session dialogue will illustrate how confrontation techniques can be used even without extensive case formulations over the entire course of the treatment. The chapter provides illustrations for relevant and recent research findings with corresponding techniques.