Failure of a post-retained restoration can provide a challenge to the general dental practitioner (GDP) in terms of diagnosis, treatment planning and communication with the patient. The cause of failure must be identified, and a thorough assessment of the restoration, remaining tooth and its functional and aesthetic demands carried out in order to plan treatment to provide the most reliable result. Clinical Relevance: This article discusses the assessment of failing post-retained crowns, with discussion of reasons for failure, thereby assisting the GDP in decision-making and treatment planning for such teeth.