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The question is whether a line of sight is required for Sauron to see or sense the Ring. I suspect it has more to do with the particular relationship between the bearer of the Ring and the Ring itself. So, for example, Sauron knew instantly when Frodo put the Ring on in Mount Doom, but then Frodo basically challenged Sauron directly at this point. The same question comes up with Gollum, who carried the Ring for 500 years in the caverns of the Misty Mountains and was never sensed by Sauron.
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`These are indeed strange days,' he muttered. `Dreams and legends spring to life out of the grass.'
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