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Originally Posted by Kuruharan
Is there a definitive statement about how many times Gollum went to Mordor?
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The Tale of Years states the following:
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2980....About this time Gollum reaches the confines of Mordor and becomes acquainted with Shelob.
3009 Gandalf and Aragorn renew their hunt for Gollum at intervals during the next eight years.....At some time during those years Gollum himself ventured into Mordor, and was captured by Sauron.
3017 Gollum is released from Mordor. He is taken by Aragorn in the Dead Marshes...
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Since Aragorn took Gollum to Mirkwood, Gollum then made his way to Moria and followed the Fellowship, and then Frodo and Sam, to the Emyn Muil, it appears Gollum only entered Mordor once. The 'acquaintance' with Shelob need not have required him to go further than her lair at Cirith Ungol.