Silent sinus syndrome is a known clinical entity caused by negative sinus pressure from acquired obstruction of the maxillary sinus ostium with resulting enophthalmos and hypoglobus. We present a case in which, after septorhinoplasty, a patient developed progressive enophthalmos and hypoglobus. His evaluation was consistent with silent sinus syndrome. This case illustrates the complex reconstructive challenges of repairing an orbit in the setting of fistulization of the orbit with the maxillary sinus cavity. In particular, we highlight the inferior fornyx transconjunctival approach with simultaneous intranasal endoscopic maxillary sinus aeration.