Battle of Kashyyyk ( New Sith Wars ) The Battle of Kashyyyk was a major engagement during the New Sith Wars between the Brotherhood of Darkness and the Galactic Republic . In 1003 BBY , the Brotherhood of Darkness set its sights on the Republic stronghold on the Wookiee homeworld of Kashyyyk , hoping to gain a foothold in the Mid Rim . At first , the Republic used Kashyyyk ' s great wroshyr forests as a staging point for ambushes and guerrilla raids on the Sith with great success , causing thousands of Sith casualties . During the battle , a Sith unit called the Gloom Walkers was separated from the main Sith force , but one of their number , Dessel , was able to lead them back to the Sith army . The story of the Gloom Walkers helped to greatly raise Sith morale and inspired the Sith to win the battle and capture Kashyyyk . Prelude . For a thousand years , the Sith and the Galactic Republic did battle in the conflict known as the New Sith Wars . In 1010 BBY , a former Jedi Master , Lord Kaan , reorganized the Sith into the Brotherhood of Darkness , an army of Sith over twenty thousand strong . The Brotherhood of Darkness began a new campaign against the Republic , scoring many victories . In 1003 BBY , the Brotherhood of Darkness set their sights on the heavily - forested Wookiee homeworld of Kashyyyk , hoping to secure a foothold in the Mid Rim . The battle . That year , the Sith invaded the system , sending in wave after wave of troops to capture Kashyyyk . However , the planet was a Republic stronghold , one that the Republic wasn ' t willing to give up even with a disadvantage in numbers . When the Sith fleet first landed , the Republic forces vanished into the great wroshyr forests , turning the invasion into a war of attrition — a long , drawn - out campaign fought in the branches of the wroshyr trees . The Sith troopers were not used to fighting in the treetops , and the thick foliage and kshyy vine s provided perfect cover for the Republic soldiers and their Wookiee guides to launch ambushes and guerrilla raids on the scattered Sith forces . The losses to the Sith were catastrophic , with thousands of soldiers being killed , and many died without even seeing the enemy who had fired the fatal shot . Undeterred , the Sith Masters continued to send more troops into the maelstrom . One of the units in the second wave of reinforcements was the Gloom Walkers , commanded by Lieutenant Ulabore . During the battle , the Gloom Walkers were separated from the main lines of battle , finding themselves deep behind enemy lines . Alone and surrounded by enemies , Lieutenant Ulabore panicked , having no idea what to do to keep his men alive without direct orders . Fortunately , one of their number , a former cortosis miner named Dessel , stepped in and took command . Dessel was Force - sensitive and was able to sense the enemy ' s whereabouts even when he couldn ' t see them , allowing the Gloom Walkers to avoid Republic traps and ambushes on their way back to the front lines . It took three days and nights , but the Gloom Walkers were able to rejoin the main Sith force . The story of the Gloom Walkers became a rallying point for the rest of the Sith army , raising morale that had become dangerously low . It took almost two thousand Sith units , but the Sith were finally able to capture Kashyyyk . Aftermath . After Kashyyyk fell , the surviving Republic soldiers fled to the neighboring world of Trandosha . Twenty units of Sith troopers , including the Gloom Walkers , were sent in pursuit . What ensued was the Battle of Hsskhor , a bloody engagement fought in the desert plains outside the city of Hsskhor . The Sith ultimately won the battle , and Hsskhor was razed to the ground . After the Battle of Kashyyyk , Lieutenant Ulabore was given a special commendation as the leader of the Gloom Walkers ; he never bothered to mention that Dessel had been the one responsible for leading the Gloom Walkers back to the main Sith force . However , he later promoted Dessel to sergeant . Behind the scenes . The Battle of Kashyyyk was first mentioned in Drew Karpyshyn ' s 2006 novel , " " . It was later mentioned in " " .