Septic pulmonary embolism (SPE) is a rare complication that happens when infected thrombi from the original site of infection break off and travel to the pulmonary blood vessels, causing an infarction or an abscess. Cases were reported on SPE, with tricuspid or pulmonary valve endocarditis being the most common primary site, especially in intravenous drug abusers. There are, however, very few reports of SPE brought on by septic cavernous sinus thrombosis (CST). Here, we describe the case of an 18-year-old male who had a pustule on his left eyelid, after which he developed fever, spontaneous swelling of his left eye, followed by his right eye, along with bilateral proptosis and diplopia, and new-onset dyspnea. Auscultation revealed decreased breath sounds in the left lung fields. Magnetic resonance imaging (MRI) revealed cavernous sinus thrombosis. Blood cultures isolated Staphylococcus aureus species. High-resolution computed tomography (HRCT) revealed a left-sided pneumothorax with minimal pleural effusion and multiple nodules scattered among both lungs, suggesting septic pulmonary emboli. We report this case to convey how a minor lesion, that is, an eyelid pustule (stye), can get complicated and set off a spiral of events that takes an unexpected tangent, challenging physicians and necessitating a rigorous approach.