Free tissue transfer (FTT) is a cornerstone of head and neck reconstruction. Although rare, complications of FTT surgery can be devastating, including failed flap harvest, wound breakdown, or flap loss ultimately. Thus, modern microvascular surgeons bolster surgical and clinical expertise with a growing number of technological advances to optimize patient care and outcomes. These technologies can be applied in the preoperative, intraoperative, and postoperative period. Various preoperative imaging modalities can assist in selecting the optimal donor site and advanced perforator planning. Intraoperatively, novel technologies can assist with microvascular anastomoses, operative magnification and visualization, and assess free tissue perfusion. Postoperatively, routine clinical assessment can be augmented by a variety of adjunctive monitoring techniques designed to assess tissue health, arterial inflow and venous drainage. The overall ease and success of performing FTT can be improved by employing novel technologies at every phase of the surgical process. This article will expand upon established and upcoming technological advances and the existing literatures to support their use.