Map of the area around Overlook

...the place seemed immeasurably huge. Mostly the towering walls had been constructed of a grey-white stone but in places blocks of different colors had been worked in, along with silver, copper and gold, to scrawl the whole with cabalistic patterns..

Murgen, She Is The Darkness

Overlook was Longshadow's fortress and was the southernmost building of significance in the Shadowlands. Its purpose was to protect him from the shadows which infested the Plain of Glittering Stone. Even when incomplete after 20 years of work, the height of the fortress's towers put the Tower at Charm to shame. The exterior walls were 100 feet tall. They were covered in gold and silver runes and protective spells. At night its towers were shining like lighthouses, in order to keep rogue shadows away. On its north wall, there were 200 yards between two crystal-topped towers. Longshadow never completed his fortress.

In Bleak Seasons, Murgen observed Overlook for the first time through spectral eyes, that is, ghost-walking with the disembodied spirit of the comatose wizard Smoke. He observed:

Longshadow's fortress was gargantuan. Overlook dwarfed every human construction I have ever seen, including the Lady's monstrous tower at Charm. Already two decades in the building, Overlook's construction had become the main industry of Shadowcatch-the city that was called Kiaulune before the coming of the Shadowmasters.

At the start of the events of She Is The Darkness, Overlook and Shadowcatch (the city whose purpose deemed by Longshadow was to ensure his fortress' completion), was still recovering from a devastating earthquake which left Shadowcatch in ruins. Following the advice of the turncoat Mogaba, Longshadow would allow refugees from Shadowcatch to reside within Overlook's walls, but only to guarantee eventual continuation of the construction.

Following Longshadow's defeat at the Battle of Charandaprash, Overlook itself was besieged and seized by the Taglian legions serving the Black Company leaders Croaker and Lady. Much of it was wrecked by continual fireball projector fire and sorcery, resulting in the collapse of at least one tower and the staining of its ivory exterior.

After much of the leadership of the Company was imprisoned in magic stasis by Soulcatcher beneath the Plain of Glittering Stone, Overlook was next occupied by Sleepy the Annalist, her key ally Ky Sahra, the wizards One-Eye and Goblin, and what remained of the Black Company. From the tower, the Company waged the losing Kiaulune wars against Soulcatcher's Protectorate. The fortress was eventually reduced to dust by Catcher, who spent two years analyzing the sorcery imbued in the structure's walls to create spells that obliterated the stone within.