Problem: Obesity, an ever-increasing concern, has an associated growth in weight loss methods to deal with the rising demand. Massive weight loss (MWL) at an accelerated rate, as seen in bariatric surgery, leaves patients with deflated, hanging tissue, which interferes with movement and hygiene. Reconstructive procedures address the hanging skin through multiple procedures. Documented complications are infections, dehiscence, seroma, and hematoma formation. This review seeks to uncover associations between the method of surgical weight loss and contouring surgery complications in order to better inform patients of their safest weight loss option and extend wound healing improvements to other poor healers. Methods: PubMed and Ovid databases were accessed through Weill Cornell Medical College (WCMC) Library and searched for relevant review articles and studies within ten-years using key terms weight loss, contouring, wound healing, gastric, bariatric, reconstruction and obesity. Abstracts, commentary, or articles exceeding the ten-year limit were excluded. Results: Twenty-eight articles were narrowed to fourteen, which provided information on procedures, wound healing, and complication rates associated with reconstructive surgery in the MWL population. Conclusions: MWL patients have healing difficulties similar to other surgical patients with multiple comorbidities. To determine the root of the poor wound healing cascade in this population, patients need to be procedurally matched, separating the restrictive and malabsorptive procedures. Relating wound healing to the dietary patterns of this patient population will provide an opportunity for intervention in other surgical groups.