If I may interject with an alternate theory? I'm a semi-noob so don't mind me if I'm horribly half-baked here.
So far everyone is looking at this from the perspective of the reader examining Frodo. But Frodo, Gollum, and Sam are not the only major chracters at Sammath Naur.
The Ring itself is a character and deserves some discussion here.
From the moment the ring is introduced we are told that it is, to some degree, self-aware. While it is not a sentient being per se, it is imbued with part of Sauron's consciousness.
Just as Sauron seeks the ring with all of his servants and abilities, the Ring seeks Sauron. The only way it can do this is to manipulate the mind of whomever bears it. It manipulates everyone who comes in contact with it except for Tom.
It manipulates Deagol into retrieving it. It manipulates Smeagol into killing Deagol to have it - and to keep it safe until it needs to be put into play. It manipulates Bilbo by drawing him into contact with Gollum, and then manipulates his actions later in life.
But perhaps most telling is it's manipulation of Isildur at Sammath Naur. Isildur knows from whence the Ring came, and he knows what it can do. He also knows that it is irrevocably tied to Sauron. But he can't destroy it when he should - and indeed when told to by a higher authority (Elrond).
I personally do not believe that either Frodo or Isildur necessarily failed when they were within reach of destroying the ring. If anything, Isildur is more of a failure than Frodo - because Frodo merely submits to the Ring is a moment of weakness, while Isildur is corrupted by the Ring in a moment of relative victory. But I believe "corrupted" is the operative term.
My theory, however half-baked, is that the Ring is self-aware to the extent that it knows where it needs to go to get back to Sauron, and it also knows when it is in danger.
There can be only two reasons for the Ring to return to Sammath Naur - either to be reclaimed by Sauron, or to be destroyed. The Ring uses whomever wears it to get it's will. So presumably the Ring knows what the wearer wishes to do with it.
As the Ring's power would be at it's very apex at Sammath Naur, presumably it's awareness also increases - as does it's ability to manipulate whomever possesses it. The Ring is able not only to find it's way back to Sauron, but also to find it's way out of danger at Sammath Naur - the only place it can be damaged or destroyed. At the point where it is most powerful, the Ring itself can manipulate it's bearer into removing it from danger - thus allowing Sauron another crack at finding it, and allowing itself another crack at finding Sauron.
The "failure" we speak of could really be the "success" of the Ring, the triumph over the will of it's bearer.
This would jive very well with the theory that nobody can conciously cast the Ring into the fire of their own free will. The Ring will not let them. To cast it into the fire is to let go of it - and letting go implies possession.
I don't believe that Frodo fails morally, I think - as many people seem to - that the Ring is firmly in control at Sammath Naur, no matter who wears it.
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