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In The Fellowship of the Ring, Book Two, III The Ring Goes South, there is an eerie passage when Aragorn guides the fellowship from Hollin (Eregion) to the mountain Caradhras:

It was the cold chill hour before the first stir of dawn, and the moon was low. Frodo looked up at the sky. Suddenly he saw or felt a shadow pass over the high stars, as if for a moment they faded and then flashed out again. He shivered. ‘Did you see anything pass over?’ he whispered to Gandalf, who was just ahead. ‘No, but I felt it, whatever it was,’ he answered. ‘It may be nothing, only a wisp of thin cloud.’ ‘It was moving fast then,’ muttered Aragorn, ‘and not with the wind.’

What was this shadow?

Apparently, this shadow was not caused by the crebain (regiments of black crows from Dunland and Fangorn Forest), which appeared on the previous day and which were clearly recognized by Aragorn.

It could have been a fell beast or even a Nazgûl riding on a fell beast. However, later in The Two Towers, Book Three, III The Uruk-hai, we learn from Grishnákh that the fell beasts were not supposed to cross the Anduin yet:

Nazgûl, Nazgûl,’ said Grishnákh, shivering and licking his lips, as if the word had a foul taste that he savoured painfully. ‘You speak of what is deep beyond the reach of your muddy dreams, Uglúk,’ he said. ‘Nazgûl! Ah! All that they make out! One day you'll wish that you had not said that. Ape!’ he snarled fiercely. ‘You ought to know that they’re the apple of the Great Eye. But the winged Nazgûl: not yet, not yet. He won’t let them show themselves across the Great River yet, not too soon. They’re for the War – and other purposes.’

This goes well with a description in Unfinished Tales, Part Three: The Third Age, IV The Hunt For The Ring, (i) Of the Journey of the Black Riders according to the account that Gandalf gave to Frodo:

(…) But Sauron did not underesteem the powers and vigilance of the Wise, and the Nazgûl were commanded to act as secretly as they could. (…)
The Lord of Morgul therefore led his companions over Anduin, unclad and unmounted, and invisible to eyes, and yet a terror to all living things that they passed. (…)

And indeed, the first encounter of the fellowship with a winged Nazgûl that is described in detail in The Fellowship of the Ring, Book Two, IX The Great River, occurs on the east-bank of the Anduin.

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3  
Huh, good point. I'd always assumed it was a Nazgûl, but I'd never given Grishnákh’s comment any thought in that regard. +1 for a good question. – Janus Bahs Jacquet Jan 27 at 18:18
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@Janus Bahs Jacquet: That kind of assumes that Grishnákh is in Sauron's complete confidence, and is privy to all his plans and acts. More likely that it's general orders for the Nazgul to stay east of the river, but one got sent on a special secret mission, especially as Sauron likely doesn't want the troops to know about the Ring &c. – jamesqf Jan 27 at 18:38
up vote 20 down vote accepted

It's never explained.

In The Treason of Isengard, Christopher Tolkien suggests it was probably a Nazgûl, though he admits the contradiction:

The dark shape 'like a cloud yet not a cloud' that momentarily cut off the moon's light is surely reminiscent of the shadow that passed over the stars as the Company journeyed on from Hollin in 'The Ring Goes South' (VI.421 - 2), and which Gandalf unconvincingly suggested might be no more than a wisp of cloud. Then too Frodo shivered, as here he 'felt a sudden chill'. As I noted (VI.434), the former incident was retained in [the final draft of Fellowship] but never explained: the Winged Nazgûl had not yet crossed the Anduin. But it seems likely to me that the shadow that passed across the stars near Hollin was in fact the first precocious appearance of a Winged Nazgûl.

History of Middle-earth VII The Treason of Isengard Chapter XVII: "The Great River"

Of course, this is obviously incompatible with Grishnákh's statement. Unfortunately there's no other immediately obvious explanation; none of Tolkien's drafts or letters go into any more detail on it.

The first draft of the chapter is remarkably similar to the final:

Frodo kept looking up at the sky, partly because of its beauty, partly because of Elrond's words. Suddenly he saw or felt a shadow pass over the stars - as if they faded and flashed out again. He shivered.

'Did you see anything?' he said to Gandalf, who was just in front.

'No, but I felt it, whatever it was,' said the wizard. 'It may be nothing, just a wisp of thin cloud.' It did not sound as if he thought much of his own explanation.

History of Middle-earth VI The Return of the Shadow Part 4: "The Story Continued" Chapter XXIV: "The Ring Goes South"

And it is not drastically changed in later revisions. We don't know what Tolkien intended for this to be; whether it was an error he missed or forgot to correct, or if it was an intentional mystery. We just don't know.

The most plausible in-universe explanation is jamesqf's, from a comment on the question:

More likely that it's general orders for the Nazgul to stay east of the river, but one got sent on a special secret mission, especially as Sauron likely doesn't want the troops to know about the Ring &c.

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As Loong's quote of Grishnákh says, "He won’t let them show themselves across the Great River yet, not too soon. They’re for the War – and other purposes." -- Two things to note (much like jamesqf's comment you quote in your answer) -- 1) "a shadow pass[ed] over the high stars, as if for a moment they faded and then flashed out again" isn't exactly "showing itself" now is it? 2) The real question IMNSHO is: What mission was that Nazgûl on as he flew high over Hollin? – user23715 Jan 27 at 23:50
    
@user23715 Spying on the Fellowship, I would assume – Jason Baker Jan 28 at 0:03
    
Well, yes. -- It is rather obvious when you look at that passage in context. Hence the reason Tolkien never thought to be more explicit. :) – user23715 Jan 28 at 0:24

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