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.
In the Order of the Phoenix, Voldemort possesses Harry, and it hurts. Greatly. I think that Dumbledore explained that it was because Voldemort's rotten soul was incapable of assimilating Harry's pure soul, that Voldemort didn't understand the love and friendship etc that Harry has in his heart. But, I think it was a lie. Remember that in Deathly Hallows, while looking for information regarding Horcruxes, it is discovered that it is in fact possible to merge a soul fragment back, but that the process was extremely painful. Now then, if Voldemort tried to possess Harry, and Harry had a fragment of Voldemort's soul, I think that it could have been the true cause of Voldemort's pain: the fact of having his soul so close of another fragment. I think that Dumbledore knew that fact, but had to lie to Harry because it was inappropriate to let him know that he had one of Voldemort's soul fragments at the moment. Is that right? Or was it truly the pure soul of Harry's...
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