Question: How did Gollum survive his fall outside of Shelob's Cave?
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Answer: He fell onto a grassy knoll a little way underneath the mouth of the cave. How he managed to get into Mount Doom is another matter, but bearing in mind the Hobbits took AGES to get through Mordor, he must have beaten them to it. If you look closely at him inside Mount Doom you can see he has bruises, cuts etc., probably inflicted by his fall.
The Doctor