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Purpose of Review: To review the various factors associated with the most common cause of maxillary sinus dysfunction; recalcitrant chronic maxillary sinusitis (RCMS). In addition, available medical and surgical management options are discussed along with various tips and tricks for optimal management., Recent Findings: Defects in mucociliary clearance, immunodeficiency, anatomic factors, and infectious etiologies have been implicated in dysfunction of the maxillary sinus leading to RCMS. Medical management including oral antibiotics or topical drugs have shown varying degrees of success. Endoscopic modified medial maxillectomy (EMMM) has been shown to significantly improve symptoms in patients with RCMS., Summary: A dysfunctional maxillary sinus presents a clinical challenge. A thorough evaluation of any potential contributing factors must be done in addition to an assessment of the adequacy of prior surgical treatment of the maxillary sinus. Beyond the middle meatal antrostomy, EMMM can be used to effectively address RCMS. In cases that fail EMMM, removal of the condemned mucosa to encourage auto-obliteration of the sinus can be considered., (Copyright © 2022 Wolters Kluwer Health, Inc. All rights reserved.)