Some follow up on an issue discussed in this thread.
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I've wondered if he in fact sent Gollum to Cirith Ungol and Shelob with an unexpected result that Shelob sets Gollum free
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My comment was pure speculation in the nature of connect the dots.
Gollum was drawn to Mordor. "And sooner or later as he lurked and pried on the borders he would be caught and taken - for examination... When he was found he had already been there long, and was on his way back. On some errand of mischief." The implication appears to be that he was released, but this is not expressly stated. All we know is that while he was at or in Mordor, he met Shelob.
"Already, years before, Gollum had beheld her, Sméagol who pried into all dark holes, and in past days he had bowed and worshipped her..." Gollum was in Mordor years before only when he was caught and brought to Sauron. So he encountered Shelob either on his way in or on his way out.
"And as for Sauron; he knew where she lurked... And sometimes as a man may cast a dainty to his cat (his cat he calls her, but she owns him not) Sauron would send her prisoners that he had no better uses for..." So Sauron was known to do this and might have done so with Gollum.
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I am re-reading LoTR and came across Gollum's own words regarding his capture by Sauron. As he and Frodo and Sam descend towards the Dead Marshes, he speaks of a way around the marshes that leads to the roads to the Black Gate. He then states as follows:
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His Eye watches that way all the time. It caught Sméagol there, long ago.
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So Gollum did not enter Mordor through Cirith Ungol and did not encounter Shelob when he entered Sauron's realm. This bolsters the argument that Sauron released him to Cirith Ungol, expecting that Shelob would trap him. Of course, Gollum, after being released from Mordor might have lurked on its borders, found the path to Cirith Ungol and entered it from outside Mordor. This seems unlikely to me for two reasons. First, why would Gollum wish to re-enter Mordor? Second, having been released, wouldn't he immediately resume his search for Bilbo and the Ring?