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In the First and Second Ages of Middle Earth, Sauron had the ability to change into an appealing form to Men and Elves. He could then deceive them, and used the name of Annatar. However, once he was on Numenor and the Island was destroyed, so was his fair form so he was subsequently trapped in his "hideous" form.

Since it is said that he was gaining much of his old strength back, would it have been possible for Sauron to regain the ability to appear fair to the peoples of Middle Earth again had he regained the ring from Frodo and Sam?

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We don't know for sure; as far as we know, he never tries.

However, Sauron loses the ability to assume a fair-seeming form during the destruction of Númenor:

But Sauron was not of mortal flesh, and though he was robbed now of that shape in which he had wrought so great an evil, so that he could never again appear fair to the eyes of Men, yet his spirit arose out of the deep and passed as a shadow and a black wind over the sea, and came back to Middle-earth and to Mordor that was his home.

The Silmarillion IV Akallabêth

According to Appendix B, this occurs in S.A. 3319. The Ring was created c. S.A. 1600, so he had already made the Ring when he lost his fair-seeming form. It seems stunningly unlikely that recovering the Ring would put him at a higher level of power than when he was at in the Second Age, so I'm inclined to say no, he could not.

However, note that it only says he could not appear fair to men. He could, perhaps, still assume a form that seemed fair to Dwarves (for example), but we don't know.

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Plus an extra one, if I could, for that last paragraph alone - only lost the ability to seem fair to men? Oh, the implications! – Megha Jan 10 at 0:56
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Actually we do know because it says he never could again – ulmo Jan 10 at 1:03
    
@ulmo "he could never again appear fair to the eyes of Men" does not preclude appearing fair to other races; what a Man finds fair may not be the same thing a Dwarf (or an Ent, or any other kind of creature) would find fair – Jason Baker Jan 10 at 1:05
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Hmm, that is an interesting point...seems a bit strange that it could depend on race. I saw this as an analogous thing that happened to morgoth. He invested all of his power into evil such that he was never again able to appear fair to anyone and maintained the shape of the tyrant of utumno. I feel like saurons experience mirrors this...but your point is taken – ulmo Jan 10 at 1:08
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@ulmo Tolkien talks about that briefly in "Notes on Motives", in Morgoth's Ring. Sauron put much, much less of himself into the Ring (compared to what Morgoth put into Arda), which is why Morgoth was limited in ways Sauron wasn't – Jason Baker Jan 10 at 1:09

No. From Akallabeth: "he could never again appear fair to the eyes of men, yet his spirit arose out of the deep and passed as a shadow and a black wind over the sea back to middle earth". Note that after he returns to middle earth he is in possession of the ring, thus he cannot appear in fair form even with the ring.

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In a deleted scene from the final Peter Jackson film, Sauron demonstrates the ability to regain his "fair" form for a few brief seconds, just before his iconic fight with Aragorn.

There's no specific indication that possessing the One Ring would allow him to do so for longer, but by the same token I think we can assume that being uber-powerful couldn't possibly hurt his chances.

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Don't blame me. The question doesn't say "books only, please". – Valorum Jan 10 at 0:50
    
That's edited or fanmade, that part never actually happened lol – thegreatjedi Jan 10 at 7:52
    
see original youtube.com/watch?v=BtEC3pNEMhY – thegreatjedi Jan 10 at 7:55
    
@thegreatjedi - Well, this was the (released) alternative ending but the image of annatar was leaked as a set photo and then spliced into the footage. Since it's all based on Jackson material, I'm willing to leave it up. – Valorum Jan 10 at 9:01
    
According to the books, Illuvatar's wrath came swiftly upon Numenor at its downfall. To escape it, Sauron abandoned his fair form and quickly spirited himself away - apparate, if you will - to Middle Earth. His fair form was thus trapped with Numenor beneath the seas until the end of time, and that is why he cannot appear before the lesser races in his fair form forever. Note that fair form here refers to a tangible body made of matter - Sauron can no longer take a form similar to the Free Peoples, restricted instead to his present dark form. Planting thoughts in people's mind is different tho – thegreatjedi Jan 10 at 15:15

No he wouldn't,he had the ring when he left Numenor and was unable to wrought himself a fair semblance because he'd been immersed in evil for too long and as far as i know he was at his full strength then.

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Surely he wouldn't bother to appear 'fair' if he had the Power of the One Ring - not the sort of entity to bother with niceties.

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That's not the point - the question was whether or not he would have the ability. – Mithrandir Jan 10 at 8:25

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