The Interactions of the Ring-Bearers

[Inziladun]

Originally Posted by Mithadan

I generally do not think of looking at the Tale of Years for source material, so good catch.

I like TOY for that very reason. For the chronically ADHD riddled (like me), it's a nice, quick resource.

Originally Posted by Mithadan

Gollum reveals that he used this route to exit the Black Land and escape from Mordor. He denies that he was "released" with instructions. Later in the chapter Shelob's Lair, Gollum's first meeting with Shelob is described as having happened "years before" but does not discuss the specific circumstances other than his promise to bring her food.

Odds are, Gollum told Shelob whatever he thought would save his own bony self. He may have been drawn to her as a greater source of malice, though, and maybe had thought he could use her at some undefined future point.

Originally Posted by Mithadan

So It appears that Gollum was allowed to exit the Dark Tower and enter Cirith Ungol. It is possible that he was led to believe that he had escaped. It is unclear whether Sauron expected that Shelob would kill Gollum. Based upon the Tale of Years entry, it seems that his exit from Mordor was not the first time that he met Shelob, though Shagrat's statement may contradict this.

I think Sauron believed Gollum could probably make his way out of Mordor, though I doubt he'd have lost any sleep had that not been the case.