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In the Extended Edition of The Return of the King movie, in the scene at the Black Gate, the Mouth of Sauron comes out to parley with the company. Eventually, he presents Frodo's mithril shirt to Gandalf, and delivers the taunt that eventually leads Aragorn to decapitate him:

The Halfling was dear to thee, I see. Know that he suffered greatly at the hands of his host. Who would have thought that one so small could endure so much pain? And he did, Gandalf. He did.

This dialogue - and, more importantly, Sauron's finding of the mithril shirt - seems to indicate that he already knew a Hobbit had been present in Mordor. If this was the case, even at this late point, why was he not actively searching for said Hobbit? How was he unable to see the Fellowship's true plan even after he had made the very unusual discovery of a Hobbit in Mordor and had known for a long time that a Hobbit was carrying the Ring?

I'm not expecting any further exposition on this from the movies, but does Tolkien explain this any better in his writings? Or does he simply render those scenes entirely differently to the movie?

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    In the film, the shirt wasn't found in Mordor, it was stripped from Frodo while he was prisoner in Minas Morgul (iirc), which is still in Gondor. Jackson may have said something about it in the commentary to the RotK:EE - iirc, it was that Mouth/Sauron was knowingly screwing w/ the party. That Frodo escaped from Minas Morgul may not have been known to Sauron at that time. I'll have to go check out the commentary when I get a chance – NKCampbell Jun 29 at 22:30
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    @Prometheus: To Sauron and any rational person, letting a Hobbit keep the ring and sneaking into Mordor alone to destroy the Ring are both crazy, insane plans. So Sauron assumed Frodo was on some kind of mission, but he'd have no reason to believe it was that important. Gandalf and Elrond's plan boiled down to "we don't have a chance, so let's try something absolutely crazy and have faith God lets it work out." – Shamshiel Jun 29 at 23:02
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    Minas Morgul/Ithil is on the edge of Mordor, and like several other border fortresses, originally built by Gondor to keep an eye on Mordor but abandoned/conquered as Sauron grew in strength and Gondor declined. Geographically its Mordor, politically it was sometimes Gondor, sometimes Mordor. – suchiuomizu Jun 29 at 23:59
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    @NKCampbell: actually, Frodo was held prisoner in the tower of Cirith Ungol. – J W Jun 30 at 11:42
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    @DarrelHoffman Because taking the Ring to Mt Doom to destroy it is the one thing Sauron could not imagine anyone doing. He did not realize that was the plan until Frodo was at the Cracks of Doom and claiming the Ring as his. At this point he assumed Aragorn had the Ring and that was his reason for using the Palantir to reveal himself as Isildur’s heir. – suchiuomizu Jun 30 at 15:26
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It's very likely that Sauron was actively searching for the Hobbits within Mordor, but the only perspective that we get is that of Frodo and Sam, so any search efforts would be happening off-screen or off-page. But, assuming that a search was happening, Sauron had one big problem. He had just recently committed most of his forces, including the Nazgul, to the war, so his available man-power was reduced. This probably helped Frodo and Same escape detection until Aragorn arrived at the gates and drew Sauron's full attention.

As far as being able to see the Fellowship's true plan, Gandalf explains that in The Two Towers.

Indeed he is in great fear, not knowing what mighty one may suddenly appear, wielding the Ring, and assailing him with war, seeking to cast him down and take his place. That we should wish to cast him down and have no one in his place is not a thought that occurs to his mind. That we should try to destroy the Ring itself has not yet entered into his darkest dream.

Even if he "knew" that Frodo was in Mordor with the ring then, according to Gandalf, Sauron would assume that Frodo would be coming to confront him and take his place, not to destroy the ring. Sauron may have just decided (rightly) that he could handle any upstarts who tried to claim the ring.

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    "Sauron would assume that Frodo would be coming to confront him and take his place, not to destroy the ring." And in the end it turned out Sauron would have been right even if Frodo didn't know that yet, if not for Gollum and the happy accident. – JiK Jun 30 at 12:26
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    I think this is the better answer so far - it is the core/prime reason why Sauron overlooks the full import of Frodo and Sam's mission. -- Though @Edlothiad has a couple of good points and to that could be added that Galadriel, via the ring Nenya and her 'mirror', were also in contention with the mind of Sauron to keep him distracted from uncovering the truth. -- I personally believe Galadriel's efforts were no less important than any of the others. – user23715 Jun 30 at 16:48
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    @user23715 I'm not sure if there's any documentation from Tolkien supporting your belief, but I share it fully. Look at the sunlight and clean water that appeared, 'magically', right after Sam asked for them. I'm convinced Galadriel was wielding her powers from afar to protect and support them -- but subtly, without revealing her hand. – RonLugge Jul 1 at 23:19
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    Her or somebody else. Miracles exist in Middle Earth. – A. B. Jul 2 at 2:19
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    @user23715, out of interest what makes this the better answer? It begins with a wrong claim, Sauron committed all his forces to the Black gate, that is stated several times in LR. It's main point, that Sauron expected someone to claim the power of the ring and challenge him (which at that point in time Aragorn has done), is made in my answer as well (in my opinion with more relevant quotes). So how would I go about improving my answer to make it more complete? – Edlothiad Jul 2 at 8:53
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Sauron could not fathom that a stronger person being in the company of the ring wouldn't wrest it from the halfling. So while he knew up until Amon-Hen it was on the finger of the halfling, Aragorn showed himself to Sauron and in doing so dragged his attention away from the Morgul Vale and onto himself, Minas Tirith and the Host of the West.

Now Sauron knows all this, and he knows that this precious thing which he lost has been found again; but he does not yet know where it is, or so we hope. And therefore he is now in great doubt. For if we have found this thing, there are some among us with strength enough to wield it. That too he knows. For do I not guess rightly, Aragorn, that you have shown yourself to him in the Stone of Orthanc?

‘I did so ere I rode from the Hornburg,’ answered Aragorn. ‘I deemed that the time was ripe, and that the Stone had come to me for just such a purpose. It was then ten days since the Ring-bearer went east from Rauros, and the Eye of Sauron, I thought, should be drawn out from his own land. Too seldom has he been challenged since he returned to his Tower.

Gandalf's plan is through distraction. He knows he has Sauron looking the wrong way, and so long as he does, he will not fear anything coming into Mordor

'His doubt will be growing, even as we speak here. His Eye is now straining towards us, blind almost to all else that is moving. So we must keep it. Therein lies all our hope. This, then, is my counsel. We have not the Ring. In wisdom or great folly it has been sent away to be destroyed, lest it destroy us. Without it we cannot by force defeat his force. But we must at all costs keep his Eye from his true peril. We cannot achieve victory by arms, but by arms we can give the Ring-bearer his only chance, frail though it be.

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    One also notes that obviously Frodo didn't have the Ring when captured. This is more evidence that it's somewhere else. Furthermore, he didn't have evidence of two hobbits; the Fellowship knows the things are Frodo's and Sam's, but he doesn't. (That is, if he didn't listen to the story of the warrior who hurt Shelob, and from the evidence of the orcs, they seldom got listened to.) – Mary Jun 30 at 1:14
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    @Mary They would have no reason to believe the warrior was a Hobbit, in fact Sam wandering through Cirith Ungol was thought to be an elf warrior – Edlothiad Jun 30 at 7:07
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    @Edlothiad Indeed, "Hobbit warrior" might be considered an oxymoron by most, if they even knew what a Hobbit was. – Nuclear Wang Jun 30 at 12:28
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Yes, Sauron knows a halfling found and bore the ring. But he also knows there are several halflings in play, and he has learned something of their ability to keep hidden. Given the skills to hide and avoid detection, Sauron has come to believe halflings are also being used as spies.

Weighing the lack of the Ring, plus Aragorn's challenge via the Palantir, Suaron believes he has found a spy. The Mithril shirt raises the likely status to chief spy, and therefore useful to Sauron for the taunt from the scene in question.

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