A 37-year-old female with past medical history of depression and anxiety presented to our clinic with complaints of pulsatile tinnitus and daily headaches. While she had headaches intermittently in the past, the frequency of headaches has increased over the past 4 months to almost daily. She also reported tinnitus in the left ear starting four months ago, which had since spread to the right side. The tinnitus was described as a whooshing sound that correlated with her heartbeat and was more noticeable in quiet environments. The headaches were located in the left temporal region, and were described as pulsating, throbbing in nature. They were associated with nausea, imbalance, photophobia, and phonophobia. The patient denied any auras, vision changes, focal numbness, or weakness. CT angiogram of head and neck showed bilateral, medially oriented jugular diverticula, more pronounced on the left. Brain MRI was unremarkable. The patient was started on Topiramate 25mg twice daily and magnesium oxide 400 mg once daily, which decreased the intensity but not the frequency of the headaches. The patient underwent left jugular diverticulum endovascular coiling, following which she had 50%-85% reduction in her left pulsatile tinnitus and 20-25% reduction in the right side. Her headaches have improved a lot; she only has occasional headaches. The patient elected to defer the procedure on her right side.