BACKGROUND: Free fibula reconstruction of the mandible has been the gold standard for reconstruction of mandible owing to its rich periosteal and peroneal blood vessel supply. This demands a multidisciplinary approach of maxillofacial and plastic surgeons. Meticulous presurgical planning of harvesting fibula, resection of diseased bone, contouring the fibula to the created defect to restore the anatomy and function, microvascular anastomosis, and postoperative medical care are vital for the survival of the flap. CASE SERIES: We report a series of cases in four Indian patients. Case 1 involves a 23-year-old male individual, Case 2 involves a 47-year-old male individual, Case 3 involves a 23-year-old male individual, and Case 4 involves a 56-year-old female individual. All patients underwent fibula reconstruction of the mandible post-odontogenic and malignant tumor resections with incidental intraoperative mishaps and management with successful outcomes with a follow-up of 12 months. RESULTS: All the above cases were done with a multidisciplinary approach, including plastic and maxillofacial surgeons. Despite the incidental mishaps, it was a learning experience for the betterment of the planning of future cases. CONCLUSION: Although the free fibula flap is a conventional method for reconstruction, there is a risk of error hidden in each of its subtle steps that can contribute to flap failure. Therefore, meticulous surgical planning is mandatory for execution of the treatment plan. Although complications are inevitable, they should not overshadow the learning opportunities from each respective case.