Chronic maxillary sinusitis may present as atelectasis of the sinus with changes to surrounding structures. Several mechanisms have been proposed for this problem. Chronic obstruction of the sinus ostium, with resultant retention of secretions and osteitic bone resorption, may account for these changes. Enophthalmos is one manifestation that may require corrective treatment. Titanium micromesh reconstruction of the orbital floor, with or without onlay concha cartilage, has reliably resolved the enophthalmos. Reconstruction of the orbital floor and ventilation of the obstructed sinus ostium may be carried out relatively safely in a single operation. The standard endoscopic technique of uncinate removal and middle meatal antrostomy should be modified to prevent orbital penetration. This report reviews our series of 6 patients with this problem, as well as a comprehensive review of the literature. Recommendations for management of both the obstruction and the secondary orbital manifestations are presented.