After their discomfiture at the Ford of Bruinen by Elrond and Gandalf, the Nazgûl returned to Sauron their master in the land of Mordor. There, he furnished them with horrible winged mounts and sent them abroad once again. While mounted on these flying beasts, they were known as the Winged Nazgûl.
23 February III 3019 is the date of the first definite sighting of a Winged Nazgûl (in an encounter with the Company of the Ring on Anduin, in which Legolas shot the Nazgûl's flying mount). This seems rather unlikely to be the first flight of any Winged Nazgûl, and they presumably predated this encounter by some time. Notably, when Legolas and his companions met Gandalf, just eight days later, the Wizard seemed fully informed about Winged Nazgûl and their activities, implying that they had been active for quite some time. The implication is that they had been flying back and forth east of the Great River for a while at this point, though we have nothing to say exactly how long that 'while' might have been.
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