Background Over 175,000 Americans underwent bariatric surgery in 2013 alone, resulting in rapid growth of the massive weight loss population. As obesity is a known risk factor for breast cancer, plastic surgeons are increasingly challenged to reconstruct the breasts of massive weight loss patients after oncologic resection. The goal of this study is to assess the outcomes of autologous breast reconstruction in postbariatric surgery patients at a single institution. Methods Patients who underwent autologous breast reconstruction between 2008 and 2014 were identified. Those with a history of bariatric surgery were compared to those without a history of bariatric surgery. Analysis included age, ethnicity, BMI, comorbidities, flap type, operative complications, and reoperation rates. Propensity matched analysis was also conducted to control for preoperative differences between the two cohorts. Results Fourteen women underwent breast reconstruction following bariatric surgery, compared to 1,012 controls. Outcomes analysis revealed significant differences in breast revisions (1.35 vs. 0.61, P = .0055), implant placements (0.42 vs. 0.08, P = .0003), and total OR visits (2.78 vs. 1.67, P = .0007). There was no significant difference noted in delayed healing of the breast (57.4% vs. 33.7%, P = .087) or donor site (14.3% vs. 15.8%, P = 1.00). Conclusions As the rise in bariatric surgery mirrors that of obesity, an increasing amount of massive weight loss patients undergo treatment for breast cancer. We demonstrate profound differences in this patient population, particularly in regards to revision rates, which affects operative planning, patient counseling, and satisfaction.