The Battle of Charandaprash Pass was an important milestone in the Black Company's campaign against the Shadowmasters. Croaker led an army of around 60,000 troops. The other legion commanders were Lady and the Prahbrindrah Drah of Taglios. Longshadow, who was the last of the Shadowmasters, had his forces commanded by the traitors Mogaba and Blade.

The battle lasted for days. One of the most decisive moments was Blade's betrayal. He led a quarter of Longshadow’s army into a trap in which Croaker's army surrounded them and forced them to surrender and disarm. The trap had been laid months before by Croaker and Blade when Croaker ordered Blade's defection in order to put somebody high ranking but reliable into Longshadow's military hierarchy. Longshadow, who was very unstable at that time (due to Kina's manipulation), panicked and ordered a retreat. Both his enemies and allies noted this to be a huge tactical mistake. He and his most important allies mounted Howler's flying carpet and tried to escape. The carpet caught fire and almost crashed as it was fired upon by fireball projectors, but Kina materialized in order to save the Daughter of Night. Lady, whose sorcery was being restored to her, repelled Kina. The vision of Kina turned out to be Soulcatcher's work.

Mogaba was badly hurt, but stayed and fought bravely. Finally, Lady used her sorcery, and Mogaba's army was forced to flee. The victors were too tired to pursue them, but many were picked off by Goblin's team, which had been placed on the far side of the Dhanda Presh long before. The decisive victory led to the Siege of Overlook.