Introduction: Free flap success rates have remained stable in recent years ranging 93% to 98%. Historically, the causes of free flap failures were attributed to the surgeon’s inexperience and technique. However, there are factors beyond the surgical anastomosis that contribute to flap failure. The purpose of this study is to review each case of total flap loss in detail to develop a better understanding of complications. Methods: A retrospective study was performed over eleven years in a single surgeon’s practice, a predominantly head and neck reconstructive practice. All charts were independently reviewed. In patients who sustained total flap loss, a review was conducted of patient comorbidites, anesthesia records, perioperative and follow-up notes. Results: A total of 514 free flaps were performed. 76% (392) of these flaps were for head and neck reconstruction. There were 22 total flap losses (4%) and 26 partial flap losses (5%). Of the 22 total flap losses, four flaps were avulsed, five flaps were in patients later found to have coagulation disorders (homozygous mutations of the MTHFR gene and factor V Leiden), four patients were exposed to neosynephrine, two patients remained hypotensive perioperatively, and four delayed flap losses were attributed to pseudomonal infection. Five losses were technical or related to flap inexperience. Several representative case scenarios are illustrated. Conclusion: Careful review of free flap failures indicates that a thorough workup (particularly coagulation disorders), flap selection, surgeon to anesthesia communication, proper securing of the flap, and postoperative patient blood pressure and infection control have a greater part to play in this new era of anastomotic success.