Silent sinus syndrome (SSS) is a rare disorder involving bony remodeling of the maxillary sinuses, including collapse of the orbital floor. It is typically unilateral and seen in the setting of chronic maxillary sinusitis. Patients present with enophthalmos and hypoglobus occasionally accompanied by diplopia. The condition is generally diagnosed with CT imaging and treated surgically. While SSS is most often reported as very slowly progressive, we report a patient with evidence of significant remodeling of the maxillary sinus over a period of 5.5 months.