We present a patient who underwent orbital fracture repair complicated by retrobulbar hemorrhages twice within the first postoperative week. The suspected cause is continuous positive airway pressure (CPAP) use with inappropriate patient-modified settings. The most likely mechanism of action was venous congestion from the extrinsic positive pressure, similar to Valsalva maneuvers increasing orbital vasculature pressure. In our patient, because his orbital blood vessels had recently been cauterized, they were too fragile to handle the engorgement and bled, leading to a retrobulbar hemorrhage. It is possible that at a lower CPAP setting, the vascular congestion would not have been as severe and caused bleeding. We recommend routinely asking patients about CPAP use before orbital surgeries and instructing patients to stop CPAP usage for 1 week after any orbital surgeries if medically cleared.O bstructive sleep apnea is a common condition, affecting about 15% of males and 5% of females in the United States. 1 The first-line treatment is nightly use of continuous positive airway pressure (CPAP). Complications of CPAP use are