After suffering a heavy defeat at Charandaprash, Longshadow was besieged in his fortress by Croaker and his army. The siege lasted several days. The Black Company had to fight the enemy soldiers, the 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 Prabrindah Drah also turned against the Black Company at this time. The Company suspected that Soulcatcher had a serious hand in these events.

Eventually the Black Company conquered Overlook. Longshadow, Narayan Sing, the Howler, and the Prabindah Drah were all captured. Soulcatcher captured the Daughter of Night and escaped with her.

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