Subperiosteal hemorrhages are typically the result of blunt orbital or facial trauma. Nontraumatic subperiosteal hemorrhages are uncommon and are usually attributed to increase in central venous pressure and bleeding disorders. Here, we report the case of a 38-year-old female who underwent an upper gastrointestinal (GI) endoscopy and developed bilateral nontraumatic subperiosteal hemorrhages that resolved with conservative treatment. Here, we discuss the source of bleeding and the mechanisms for the occurrence of orbital subperiosteal bleeds. GI surgeons and ophthalmologists should be sensitive to the possibility that orbital hemorrhage that can occur following endoscopy, especially when retching or gagging occurs during the procedure.