Background: Multinodular goiter is a relatively common thyroid disorder with a marked female preponderance. Most of these goiters weigh less than 100 grams with those weighing more than 500 grams being exceptional. The massively expanding goiter due to the strategic anatomic location of thyroid gland, in addition to being cosmetically disfiguring can seriously compromise the patency of the trachea and oesophagus. Thyroidectomy for such goiters is a surgical challenge due to the possible association of tracheomalacia, retrosternal extension, skin involvement and the difficulty in intubation and dissection of the thyroid gland due to distorted and displaced anatomy. Material and methods: While presenting 2 patients who underwent thyroidectomy for glands weighing more than 500 grams, the literature is reviewed to analyze the technical difficulties and approach in such patients and the frequently encountered complications in them and their management. Results: A review of the literature revealed an additional 7 cases of patients who had undergone thyroidectomy for glands weighing more than 500 grams. Massively enlarged goiter was often associated with tracheomalacia, tracheal stenosis and retrosternal extension. Difficulty during surgery was most often encountered in establishing the airway and in exposure of the gland particularly when the skin was involved. The predominant postoperative complications were related to respiratory distress as a consequence of tracheomalacia and tracheal stenosis. Conclusion: In spite of the technical challenge related to the airway, and thyroidectomy, surgery continues to be the best option in experienced hands due to its distinct advantage of its immediate effect and complete resolution of compressive symptoms.