We know Sauron intentionally let Gollum go so that Gollum would lead Sauron's minions towards the Ring, and Sauron knew Gollum would look and follow the Ring at all costs. So when Shagrat sees Shelob with her "sneak," why did Sauron order the orcs to let him roam freely whenever he liked, and surely Sauron must have realised that Gollum was actually following the Ring bearer into Mordor.
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