Evidently, Sauron did not understand his own Ring as well as he might have. You cite one particular way in which Sauron's understanding was lacking. His failure to comprehend what he supposed was the destruction of the Ring at the end of the Second Age is another.
His persistence in attempting to unleash Gollum on the world does seem a bit strange at times.
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...finding a path that cannot be found, walking a road that cannot be seen, climbing a ladder that was never placed, or reading a paragraph that has no...
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