The Battle of Kashyyyk represented a significant clash during the New Sith Wars, pitting the Brotherhood of Darkness against the forces of the Galactic Republic. Back in 1003 BBY, the Brotherhood of Darkness strategically targeted the Republic's fortified position located on Kashyyyk, the homeworld of the Wookiee species, with the goal of establishing a strong presence within the Mid Rim region. Initially, the Republic effectively utilized Kashyyyk's expansive wroshyr forests as operational bases, launching successful ambushes and guerrilla attacks against the Sith, inflicting substantial casualties numbering in the thousands. During the thick of the conflict, a Sith detachment known as the Gloom Walkers became separated from the primary Sith force; however, one of their members, Dessel, skillfully guided them back to the main Sith army. The narrative of the Gloom Walkers served as a crucial morale booster for the Sith, ultimately inspiring them to secure victory in the battle and seize control of Kashyyyk.
For a span of one thousand years, the Sith and the Galactic Republic engaged in a prolonged struggle known as the New Sith Wars. Around 1010 BBY, a former Jedi Master, Lord Kaan, restructured the Sith into the Brotherhood of Darkness, a formidable Sith army exceeding twenty thousand warriors. The Brotherhood of Darkness initiated a renewed offensive against the Republic, achieving numerous triumphs. In 1003 BBY, the Brotherhood of Darkness strategically focused on the densely forested Wookiee homeworld of Kashyyyk, aiming to secure a strategic foothold within the Mid Rim.
In that year, the Sith launched their invasion of the system, deploying successive waves of troops with the objective of capturing Kashyyyk. However, the planet stood as a Republic stronghold, one that the Republic was determined to defend, even when faced with numerical disadvantages. As the Sith fleet initiated its landing, Republic forces strategically retreated into the vast wroshyr forests, thereby transforming the invasion into a protracted war of attrition—a lengthy and exhausting campaign conducted within the intricate canopy of the wroshyr trees. The Sith troopers lacked experience in treetop combat, and the dense foliage, coupled with the abundance of kshyy vines, provided ideal concealment for Republic soldiers and their Wookiee guides to execute ambushes and guerrilla raids against dispersed Sith units. The Sith endured significant losses, with thousands of soldiers meeting their death, many without even identifying the enemy responsible for delivering the fatal blow. Despite these setbacks, the Sith Masters persisted in deploying additional troops into the chaotic fray.
Among the units comprising the second wave of reinforcements was the Gloom Walkers, under the command of Lieutenant Ulabore. During the engagement, the Gloom Walkers became isolated from the main battle lines, finding themselves deep within enemy territory. Stranded and surrounded by adversaries, Lieutenant Ulabore succumbed to panic, unsure of how to ensure the survival of his men without explicit directives. Fortunately, one member of their ranks, a former cortosis miner named Dessel, intervened and assumed command. Dessel, possessing Force-sensitive abilities, could discern the enemy's location even when visually obscured, enabling the Gloom Walkers to evade Republic traps and ambushes as they navigated their way back to the front lines. After three days and nights, the Gloom Walkers successfully rejoined the main Sith force. The saga of the Gloom Walkers became a unifying narrative for the entire Sith army, revitalizing morale that had reached dangerously low levels. Despite needing nearly two thousand Sith units, the Sith ultimately succeeded in capturing Kashyyyk.
Following the fall of Kashyyyk, the surviving Republic soldiers retreated to the neighboring world of Trandosha. Twenty units of Sith troopers, including the Gloom Walkers, were dispatched in pursuit. This led to the Battle of Hsskhor, a brutal confrontation fought on the arid plains surrounding the city of Hsskhor. The Sith ultimately emerged victorious, and Hsskhor was reduced to rubble. In the aftermath of the Battle of Kashyyyk, Lieutenant Ulabore received special recognition as the leader of the Gloom Walkers; however, he neglected to acknowledge Dessel's pivotal role in guiding the Gloom Walkers back to the main Sith force. Nevertheless, he later promoted Dessel to the rank of sergeant.
The Battle of Kashyyyk was initially referenced in Drew Karpyshyn's 2006 novel, Darth Bane: Path of Destruction.