Here's a thought:
The fortunes of the "good guys" in Middle-earth
can (and do) wax and wane. After all, the Last Alliance
defeated Sauron with the Ring. It seems conceivable
that if the Ring was kept hidden until a time when
Sauron was on the defensive, perhaps even
driven away from Mordor, then a troop of good guys,
a sort of superfellowship, could waltz into Mordor and semi-coerce/
encourage/etc. the ringbearer to dispose of the ring.
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Aure Entuluva!
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