Is it folly that causes Frodo to put the Ring on in Weathertop?
Well, the deed is foolish, yes, but not it's not done out of folly. I don't think putting the Ring on in Weathertop was Frodo's folly, after all, it was the terribly strong presence of the nazgűls added to the Ring's natural lure that drove him to it. I would be ready to hold Frodo irresponsible the same way as people with serious mental illnesses or under heavy drugs.
Is it overconfidence that causes Frodo to get attacked by Shelob?
Overconfidence? Maybe over-delight or over-carelessness could be a better word for it. Anyway, I can't see how Frodo and Sam, or anyone, would have managed to completely fool and flee Shelob. The Hobbits were very lucky and accomplished to get that far and survive that well. If you ask a hobbit to jump three metres to the air, can you really punish him if he jumps 2,5m?
Is it weakness that causes Frodo to fail on Mount Doom?
Yes it is. But it's not Frodo's personal flaw, it's a general human (hobbit/elf/dwarf/orc/whatever) weakness. So again, why should he be punished?
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On the other hand, his behaviour in the Prancing Pony was folly and all the punishments he received for that were some harsh words by Strider.
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And the loss of Merry's ponies (and thus a steed) and Butterbur's money and bedclothes (so maybe guilty conscience for him?), to be nit-picky.
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Originally Posted by Boro
If you make an oath you better be prepared to live up to it or face the consequences. Just ask the Men of Dunharrow or Feanor.
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Or his sons...