Developing several backup strategies for high-risk reconstruction cases is crucial to patient outcomes in head and neck cancer patients. Free tissue transfer always carries the risk of flap failure, and often, surgeons can be caught out with difficult-to-close wounds over crucial areas. In this article, we discuss several difficult cases after failed free flap reconstruction with crucial structures exposed. The backup reconstruction options need to be robust and reliable. The article focuses on defects in the head and neck area, including the cranium, oropharyngeal defects, and other defects on the external area of the head and neck. Often, a repeat free flap may be required, but if possible or if local or regional options are available, they would be preferable, given the morbidity already presented within this group of patients.