Sinonasal organizing hematomas are benign lesions often mistaken for malignancy due to their aggressive appearance on diagnostic imaging and endoscopic findings that favor advanced disease. The destructive nature of this pathology paired with the rarity of the presentation often results in diagnostic deception that may escalate intervention planning and affect discussion of prognosis with patients. Herein, we present a case of a 56-year-old male with left-sided nasal obstruction and daily epistaxis, where computed tomography imaging revealed heterogeneous opacification of the left maxillary sinus, erosion of the left inferior orbital wall and extension into the nasal cavity. Although clinical and radiographic presentations of sinonasal organizing hematomas can be managed definitively with endoscopic intervention, there is a need to increase awareness of this entity among clinicians to improve our prognostic counseling with patients.