Oral cancers are amongst the most common cancers in the Indian subcontinent; in India alone, an estimated 1.2 lakh new patients were diagnosed with it. Reconstruction with free flaps slowly gained popularity over time to become the standard for care for treating large head and neck defects. Flap selection is a complex process; more specifically, the preoperative conditions of patients, the extent of the disease, and the resources available are critical considerations to consider when selecting the best reconstructive technique. It is very well established that certain parts of India, especially the tribal area of Central and southern India, have high prevalence of sickle cell trait (SCT) and sickle cell disease compared to the rest of the country. The sickle cell trait poses a potential increase in morbidity in the perioperative care due to surgical stress. Unfortunately, there are no published articles on the management of a free flap in a case of SCT. Here, in this article, we investigate the issues encountered during the perioperative care in a patient who undergone oral cavity composite resection with free fibula reconstruction. SCT screening must be undertaken mainly to identify, mitigate, and manage the adverse events in the perioperative period. The screening test is very inexpensive and has good sensitivity to detect the heterozygous and homozygous disease. We would recommend screening of all the patients hailing from high-risk endemic areas. The free flap in a case of sickle cell trait is not a contraindication, but a surgeon must understand the nuances in the management of complications in such case. Screening for sickle cell trait followed by perioperative blood transfusions, anticoagulation seems beneficial in a patient undergoing free flaps with sickle cell trait.