And as the Woodmen expanded toward the mountains, they must also have made contact with Gondor. There were many tribes of Northmen (of whom the Woodmen were one group) spreading south, east, and west in those centuries. They moved out from Greenwood in both directions. After Gondor's attention was directed eastward, the Dunedain made contact with the Northmen. Friendship arose between Gondor and the Northmen, and though Tolkien does not say much concerning their relationship, he implies that Men flourished throughout the western lands where Arnor and Gondor held sway.
Nonetheless, just as some Orcs survived into the Third Age in southern Greenwood, by the middle of the 6th century there were Easterlings -- whose ancestors had served or been friendly to Sauron -- also living in or near the southern forest. And far to the south dwelt Shelob, who had settled in the Ephel Duath before Sauron had built the Barad-dur. From her lair her offspring spread northward through the mountains. Undoubtedly the Last Alliance of Elves and Men had fought with the giant spiders, who would have been natural guardians for Sauron's marches. But though Gondor watched the marches for a thousand years, some spiders managed to reach Greenwood by the time Sauron settled in Dol Guldur. Perhaps he even arranged for them to be brought north.
Orcs, Easterlings, and spiders must have served as the foundation of Sauron's new realm. He would have gone into the forest and revealed himself to the descendants of his former slaves. Incapable of resisting his will, the Orcs and Easterlings (some faster than others) would have returned to his service. And they would have built the fortress of Dol Guldur in secret, far from the prying eyes of Elves, Dwarves, Men, Hobbits, or Wizards.
The Wizards, the Istari sent from Valinor, would have been very new to Middle-earth. They knew why they were there. They were keeping a wary eye out for signs of the return of the shadow. But they did not know where Sauron would arise and manifest himself, or if some other ancient evil power would rise in his place. They knew evil was coming, but not where or when. The great wars in the south, perhaps, may have led everyone to think that Gondor's ascendancy meant Sauron could not yet return. There might still be time to prepare.
The rise of Dol Guldur could not have occurred overnight. A small castle or fortress, consisting of little more than a tower and outer wall, can be built in the space of a few months, given enough materials and workers. But Dol Guldur was most likely a huge fortress, a small city, from the outset. Sauron would have needed a secure base from which to launch his various campaigns. But he also pursued a different strategy than he had in the Second Age. Instead of conquering a huge empire, and building up his military strength for direct confrontation with the Eldar and Dunedain, Sauron attacked his enemies through proxies.
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