Background <p>Thoracic Endometriosis (TES) is a condition which is characterised by the presence of endometrial tissue in airways, pleura and lung parenchyma. It is a rare pathology which typically presents as catamenial pneumothorax, haemothorax, haemoptysis and pulmonary nodules. Our case report addresses the challenges in diagnosing and treating TES, particularly in cases with recurrent pleural lesions. In our case report, we present a case of recurrent TES post-oophorectomy which did not respond to medical management.</p> Case Description <p>A 39-year-old woman, known case of recurrent thoracic endometriosis, presented with right-sided shoulder pain for a duration of 1&#xa0;year. She gave a history of recurrent catamenial pneumothorax for which the patient underwent right-sided pleurectomy in 2018. In view of severe dysmenorrhea, patient was evaluated and diagnosed with bilateral pelvic ovarian cysts with deep infiltrating endometriosis and underwent total laparoscopic hysterectomy with bilateral salpingo-oophorectomy in 2020. Postoperatively, she was started on cyclic combined hormonal pills which she continued for a duration of 2&#xa0;years. One year after initiation of the hormonal contraceptive, the patient developed complaints of right-sided shoulder pain, following which she was taken up for redo thoracotomy with excision of deep infiltrating endometriotic nodule.</p> Conclusion <p>The role of preoperative hormone therapy is questionable, whereas definitive surgical management using a multidisciplinary approach offer better symptom relief and lower recurrence rates. Following surgical excision of lesions, hormone therapy in the form of oral contraceptive pills and GnRH analogues when used continuously are found to have a definitive reduction in recurrence of symptoms.</p>