The twenty-first century, with its transforming ideology and rising acceptance, is witnessing an increased number of transgender people applying for gender reassignment surgery (GRS). The procedure of GRS is a lengthy and complex one involving the active collaboration of multiple disciplines including psychology, psychiatry, family medicine, plastic surgery, endocrinology, otolaryngology, urology, gynaecology, maxillofacial surgery, and anaesthesiology. The considerable paucity of literature regarding the management of patients presenting for GRS places health care providers at a disadvantage. It is imperative to cautiously regard the specific medical, emotional, social, and economic concerns regarding these patients. Health care providers need to be trained well to deal empathetically with such patients. The present literature about GRS deals mainly with the surgeon’s perspective, while the anaesthetist’s approach remains hazy. This is because GRS imposes the need for anaesthesiologists to search for better and more efficient modes of anaesthesia so as to improve prognosis and minimize the associated morbidity. Anaesthetists should understand the associated psychological aspects and effects of hormone therapy while performing an extensive and informative pre-operative evaluation to formulate an effective strategy. Providing the optimal modes for anaesthesia and keeping a cautious watch for complications along with timely intervention in the advent of the same comprise the approach for high-quality anaesthetic care. This review aims to provide a detailed overview of significant considerations and competent peri-operative outcomes in patients presenting for GRS.