The Siege of Overlook was the final battle of the Shadowmaster wars. It was fought between Croaker of the Black Company (the appointed Liberator of the armies of Taglios) against Longshadow, the last of the Shadowmasters, during She Is the Darkness.
After suffering a heavy defeat at the Battle of Charandaprash, Longshadow was besieged in his fortress Overlook by Croaker and his armies. The siege lasted several days. The Company and the Taglians had to fight the cornered enemy Shadowlanders; trained shadows sent by the last surviving shadowweavers; mobs of feral shadows emerging from the shadowgate; and the harsh winter.
The first breach of Longshadow's defense was achieved by Lady's soldiers. A group of them entered the fortress through its network of scaffolding and managed to hold their position inside. A few days later a tunnel was made under the wall using Lady's shadow-killing fireball projectors. At the time Lady and her soldiers were executing this decisive assault, Longshadow was betrayed by his allies Howler and Narayan Singh. The Prahbrindrah Drah also turned against the Black Company. The Company suspected correctly that the wildcard Soulcatcher was the driving force behind these events.
Eventually the Black Company conquered Overlook. In addition, the Company captured many high-value prisoners: Longshadow, Narayan Singh, the Howler, and the Prahbrindrah Drah. But Soulcatcher abducted the child of Croaker and Lady, the Daughter of Night, and escaped with her before she could finally be reunited with her parents. The siege would be followed by Croaker's ill-fated crossing into the shadowgate, and the beginning of the 15-year-long period known in the Company's history as the Captivity.