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Originally Posted by Raynor
I don't think it is about Sauron's relationships with the wielder of the ring, but his relation to the ring, and if anything helps/hinders his perception. At Amon Hen, the particularity of that place of sight helped him almost pinpoint Frodo. At the entrance of Mordor, Sauron's shadow hindered his percetion; all these are sustained with quotes. As far as Sauron not sensing Gollum, I think it is purely a matter of distance; he was too far for him to sense it, and there was nothing to favor that.
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Overall I have to agree here. The Nazgul were able to sense the Ring in and near the Shire, but clearly Sauron had no feeling whatsoever that the Ring was there for 70 years. And same for Gollum, when he had it in the Misty Mountains for 500 years.
There seems to be a role for both of line of sight (Amon Hen) and for proximity, at least in the case of Nazgul (who are presumably weaker proxies of Sauron himself in this regard), since they were able to sense the presence of the Ring when Frodo put it on in The Prancing Pony at Bree.