Free tissue transfer to the head and neck is a complex and multi-step surgical procedure. With experience, one can become very proficient with the reconstructive technique, yet achieving consistently satisfactory functional and cosmetic results without complications continues to be a challenge for all reconstructive surgeons. While advances in the field have results in >95% success rate in free tissue transfer, failure remains a catastrophic complication and resulting in significant patient morbidity. Avoiding complications starts with pre-operative planning and medical optimization prior to surgery. It continues during the procedure requiring meticulous surgical technique in all aspects including flap harvest, flap inset and vessel geometry, recipient vessel selection, microvascular anastomoses, and closure. Post-operative care is critical to a successful outcome. Various flap monitoring methods allow for real-time viability assessment and allow for early intervention and salvage of compromised flaps. Finely tuned medical management and wound care will reduce systemic patient risks. When wound issues do occur, either at the donor or recipient sites, expedient and appropriate wound care methods can minimize the complication and lead to the most successful outcome. This course will discuss the determinants of success for free tissue transfer in the head and neck in all phases of the patient care continuum, utilizing a team and consistent approach. We will describe methods to minimize risk. We will address areas that are particularly problematic with a case-based approach to provide “management pearls”, “lessons learned”, and foster participant discussion for the best solutions.