User blog comment:Maltalidenta Kwuitidherali/If Sauron Won the War of the Ring/@comment-27723099-20160201095538

A small correction: Gondor war in war with Mordor for a long time before Mordor finally broke the defenses. But after the victory of Pellenor, Gondor and Rohan reconquered all the defense lines, even Cair Andros. Even though Gondor is vastly outnumbered, it will take some time until Mordor has taken them back. Gondor will most likely destroy the rebuilt bridges of Osgiliath once again, slowing the enemy advance.

Also if Sauron already had the ring at Pellenor, Sauron's Mouth would probably have mentioned it during the negotiations. That strike on the morale would be hard enough to break even Gandalf, and would probably in a rout of the whole forces of the Free Nations, even before the battle has begun. Mordor would send out orcs to pursue the routing forces, capturing many, but I guess at least half would survive and reach Cair Andros, reuniting with the other division of the Free Forces.