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And about the relationships, do you think maybe Sam, in just getting the Ring with no intention to claim it, was better able to avoid Sauron's gaze rather than Frodo at Amon Hen and (obviously) in Mt. Doom?
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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.