On September 18, Hurricane Gordon began accelerating to the northeast around a strengthening ridge, and later toward the east as guided by a trough. Wind shear decreased, which allowed for convection to redevelop near the eye. Unexpectedly, the hurricane began restrengthening, despite moving over slightly cooler waters; instability from cooler upper-level temperatures allowed for the reintensification. Despite continued forecasts of a weakening trend, Gordon's resiliency presented a rare threatthe first since Hurricane Charley in 1992to the Azores, a Portuguese archipelago in the northeast Atlantic Ocean. At about 06:00 UTC on September 19, the hurricane attained its secondary peak intensity of about west-southwest of the Azores. By that time, the cyclone consisted of a solid ring of convection around a contracting eye. Shortly thereafter, Gordon began steadily weakening due to the combination of increasing wind shear and even cooler water temperatures. Its motion became just south of due east, causing the strongest winds to remain south of the islands. Around 09:00 UTC on September 20, Gordon passed through the Azores between the islands of Santa Maria and São Miguel, producing hurricane-force wind gusts on the former island. At the time, its sustained winds were estimated around , which remained south of any landmasses. The cloud pattern had become less organized and more ragged.