After weakening to winds of , Gert again re-strengthened to Category 4 status on September 19, as the eye became well-organized within its surrounding convection following an eyewall replacement cycle. By September 20, while the hurricane was approaching Bermuda, the appearance became more ragged due to the intrusion of unfavorable dry air. Early on September 21 Gert weakened to Category 2 intensity, around the same time it turned northward. Later that day it passed about east of Bermuda, producing hurricane-force winds on the island. Steady weakening continued as Gert accelerated northeastward under the influence of an approaching trough. The convection decreased around the center due to cooler water temperatures, and on September 23 Gert weakened to tropical storm status as it approached Newfoundland. After nearly all of the convection had dissipated, the system no longer met the characteristics of a tropical cyclone. As a result, it was declared extratropical at 1200 UTC on September 23 about 55 mi (90 km) southeast of Cape Race, Newfoundland. About six hours later, the remnants of Gert were absorbed by a larger extratropical storm. Gert was the fourth of five Category 4 hurricanes to form during the 1999 season, the highest number of such storms on record. Later, the 2005 season tied the record.