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Background: A rare, but consequential, risk of gender affirming surgery (GAS) is post-operative regret resulting in a request for surgical reversal. Studies on regret and surgical reversal are scarce, and there is no standard terminology regarding either etiology and/or classification of the various forms of regret. This study includes a survey of surgeons' experience with patient regret and requests for reversal surgery, a literature review on the topic of regret, and expert, consensus opinion designed to establish a classification system for the etiology and types of regret experienced by some patients., Methods: This anonymous survey was sent to the 154 surgeons who registered for the 2016 World Professional Association for Transgender Health (WPATH) conference and the 2017 USPATH conference. Responses were analyzed using descriptive statistics. A MeSH search of the gender-affirming outcomes literature was performed on PubMed for relevant studies pertaining to regret. Original research and review studies that were thought to discuss regret were included for full text review., Results: The literature is inconsistent regarding etiology and classification of regret following GAS. Of the 154 surgeons queried, 30% responded to our survey. Cumulatively, these respondents treated between 18,125 and 27,325 individuals. Fifty-seven percent of surgeons encountered at least one patient who expressed regret, with a total of 62 patients expressing regret (0.2-0.3%). Etiologies of regret were varied and classified as either: (I) true gender-related regret (42%), (II) social regret (37%), and (III) medical regret (8%). The surgeons' experience with patient regret and request for reversal was consistent with the existing literature., Conclusions: In this study, regret following GAS was rare and was consistent with the existing literature. Regret can be classified as true gender-related regret, social regret and medical regret resulting from complications, function, pre-intervention decision making. Guidelines in transgender health should offer preventive strategies as well as treatment recommendations, should a patient experience regret. Future studies and scientific discourse are encouraged on this important topic., Competing Interests: Conflicts of Interest: All authors have completed the ICMJE uniform disclosure form (available at http://dx.doi.org/10.21037/atm-20-6204). The series “Transgender Surgery” was commissioned by the editorial office without any funding or sponsorship. Dr. RBL reports that he serves on the standards of care committee of WPATH. No financial reward. Dr. AR reports that he serves as board member for World Professional Association for Transgender Health. This is an uncompensated position. Dr. LS reports other from Elsevier Publishing, other from Springer Publishing, outside the submitted work; and he serves on the board of WPATH (world professional association for transgender health), this is an unpaid position. Dr. JUB reports that he serves on the standards of care committee of the World professional association of transgender health. No financial reward associated with this. The authors have no other conflicts of interest to declare., (2021 Annals of Translational Medicine. All rights reserved.)