Overlook was Longshadow's fortress and was the southernmost building in the Shadowlands. Even when incomplete after 20 years of work, the immensity of the fortress put the Tower of Charm to shame. The outside 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 the Shadows away. Longshadow never completed his fortress.
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), were struck by a devastating earthquake, leaving Shadowcatch in ruins. Following the advice of the turncoat Mogaba, Longshadow would allow refugees from Shadowcatch to reside within his walls.
With Longshadow captured by the Black Company who's Old Crew (minus the two wizards, One-Eye and Goblin) having "gone to Khatovar", Overlook would then be occupied by a band of renegades lead by the Black Company Annalist's wife and understudy, Ky Sahra and Sleepy. The fortress is eventually obliterated by Soulcatcher during the Kialune Wars, which occurred after Soulcatcher trapped the Captured.