The Battle of Kashyyyk, an event that unfolded in 40 ABY during the Second Galactic Civil War, was initiated by Darth Caedus, the Sith Lord and Chief of State. His aim was to subdue and punish a member-world of the Galactic Alliance. The repercussions of this battle extended beyond the immediate conflict, leading to the Hapes Consortium withdrawing from the Galactic Alliance. Additionally, it marked the commencement of the New Jedi Order's military efforts to oust Caedus from his position, despite his Sith identity remaining concealed. Although controversial, Caedus successfully met his military goals by drawing the Confederation fleet away from their advance on Coruscant as they were compelled to aid the Wookiees.
During the engagement, the Jedi were horrified as Caedus set ablaze significant portions of Kashyyyk's forests. The Galactic Alliance Fifth Fleet found itself encircled by Confederation forces, who were supported by Wookiee warriors and a Jedi strike team. As the battle progressed, the Hapan fleet, commanded by Queen Mother Tenel Ka Djo, intervened to ensure Caedus's defeat. However, Alema Rar, a renegade Dark Jedi from the Sith world of Korriban, arrived to assist Caedus. Employing her ancient Sith Meditation Sphere, she manipulated the Bothan fleet, creating an opportunity for Caedus to escape.
Upon learning from his cousin Ben Skywalker about a Jedi conspiracy to remove him from his role as Chief of State, coupled with the Jedi Order's mass departure during the Battle of Kuat, Darth Caedus resolved to wage war against the Jedi, eliminating them as a threat, and to divert the Confederation fleet from its attack on Coruscant. The Wookiee fleet, previously undecided about joining the Galactic Alliance war effort, remained stationed in Kashyyyk's orbit while its leaders deliberated.
Caedus's plan involved compelling the Wookiees to surrender the Jedi, knowing they would refuse, thus providing him with a pretext to make an example of their world. While his Galactic Alliance Guard contingent, under Salle Serpa, attempted to suppress the Jedi academy on Ossus, Caedus emerged from hyperspace above the Wookiee homeworld with the entire Fifth Fleet. He spearheaded the Galactic Alliance forces aboard his personal Star Destroyer, the Anakin Solo.
With the Fifth Fleet positioned behind the Anakin Solo, Caedus observed the Wookiee fleet struggling to disengage from its orbital tenders, as a lone squadron of Owool Interceptors approached. The Wookiee pilots threatened to attack unless the Galactic Alliance explained their presence. Caedus responded by demanding that Kashyyyk's leaders hand over Han and Leia Solo, whom he considered enemies of his government and who were currently on Kashyyyk. In reality, Caedus's pursuit of his parents was secondary to his goal of capturing or killing the Jedi Masters and Knights who had fled to Kashyyyk from Kuat. His demand for the Solos was merely a ruse to justify attacking the planet. When the Wookiees falsely denied the Solos' presence, Caedus ordered the Anakin Solo's crew to punish Kashyyyk's inhabitants by firing the Star Destroyer's long-range turbolasers at the planet's massive wroshyrs, intending to ignite a planet-wide inferno. The Fifth Fleet, under Admiral [Atoko], was instructed to hold back and protect the Anakin Solo. As the Star Destroyer's turbolasers set the forests ablaze, Caedus ordered his gunners to target cities, while the Owools began their assault on the capital ship.
Led by the Wookiee Jedi Lowbacca, the Owool interceptors exploited the 'stripe' of the turbolaser blasts to evade the Anakin Solo's sensors. Caedus was caught off guard; by the time Commander [Twizzl] issued a ship-wide alert, the Jedi Knight was rapidly approaching the bridge. Although the Star Destroyer's defenses eliminated most of the squadron, Lowbacca managed to launch a single shadow bomb. Ben Skywalker, believing his cousin was responsible for his mother's death, attempted to assassinate Caedus to prevent further bloodshed. However, Lowbacca's bomb detonated as Skywalker attacked, incapacitating both men and eliminating the command crew. The young Jedi Knight failed to kill Caedus amidst the chaos.
Despite the failures of Lowbacca and Ben, Caedus was forced from the bridge and sought to break his cousin's spirit, attempting to turn him into his Sith apprentice. He took Skywalker to a secret chamber near the turbolaser batteries and tortured him using a Yuuzhan Vong device. Meanwhile, on Kashyyyk, Han and Leia Organa Solo fled the burning city of Rwookrrorro for Hapes to appeal for military support from Caedus's lover, Queen Mother Tenel Ka Djo. Simultaneously, Grand Master Luke Skywalker prepared the New Jedi Order for an assault on the Galactic Alliance forces using StealthXs. Skywalker led the Night Blades squadron in a raid on the Anakin Solo, aiming to eliminate Caedus and destroy the turbolaser batteries. With the Wookiee fleet still organizing itself, the Jedi were the planet's primary defense.
As Skywalker led his StealthXs against the Fifth Fleet, the Bothan fleet emerged from hyperspace and engaged the Galactic Alliance forces. Having traveled from the battle at Kuat, the Bothans, led by Admirals [Babo], For'o, and Traest Kre'fey, were battle-damaged but numerous. However, the Jedi's belief that the Bothan arrival would mask their approach was disproven when the Fifth Fleet opened fire. Caedus had anticipated their attack and even ventured out in his own StealthX to intercept Skywalker and his sister, Jaina Solo. The Jedi suffered heavy losses, but Skywalker faked his death and boarded the Anakin Solo, disabling the turbolasers as he sought out Caedus, who was torturing his son.
Upon reaching the torture chamber, Skywalker engaged his nephew in a fierce duel. Command of the Fifth Fleet passed to Admiral Atoko during the confrontation, which left both Skywalker and Caedus severely injured. The Sith Lord was eventually overpowered, and the two Skywalkers escaped, leaving Caedus to seek medical attention in the Anakin Solo's infirmary. In Caedus's absence, Admiral Atoko considered scuttling the Fifth Fleet due to the extensive damage.
While the Jedi attacked the Galactic Alliance fleet, the Corellian contingent of the Confederation fleet arrived to aid the Wookiees, along with remnants of the Commenorian and Hutt fleets, which had been decimated at the Second Battle of Balmorra. The Fifth Fleet was quickly surrounded and overwhelmed by the enemy forces. Caedus, expecting Admirals Bwua'tu and Darklighter to reinforce him, was shocked to learn that Cha Niathal had ordered them to remain near the Core in case of a Confederation advance. Adding to Caedus's woes, he was unable to countermand Atoko's order to scuttle the fleet.
Caedus then ordered his Admiral to break through the encirclement and head towards the Bothan fleet. Atoko warned of potential desertions, but Caedus dissuaded him by pointing out the Wookiees' likely revenge for their burning planet. Caedus ordered the fleet to regroup around the Anakin Solo and exploit a widening gap among the Corellian forces as the Confederation fleet seemed to prepare for new arrivals.
Queen Tenel Ka, horrified by her lover's actions, arrived with the Hapan fleet and demanded Caedus's surrender. When he refused, the Hapans, under Isolder, opened fire on the Anakin Solo. Despite the recklessness, Caedus attempted to force the Fifth Fleet through the gap, driven by an inexplicable urge in the Force. Admiral Atoko reiterated his request to scuttle the fleet, as it was on the brink of destruction.
At that critical moment, Alema Rar arrived in her Sith Meditation Sphere and, through its power, manipulated the Bothan commanders to ensure Jacen's survival. As Caedus led his forces towards the Bothans, Babo and the other commanders, influenced by Rar, became convinced it was a trap and moved to intercept the Fifth, inadvertently creating a massive hole in the blockade. Caedus led his forces to safety and jumped to hyperspace.
Aboard the Dragon Queen, the Bothans apologized for their misjudgment and sought the permanent support of the Hapes Consortium, Kashyyyk, and the Jedi in the Confederation's cause. Tenel Ka declared that she fought Jacen, not the Galactic Alliance, and disapproved of the Confederation's actions. [Tojjelnoot], the Wookiee representative, thanked the Bothan admirals but clarified that Kashyyyk also did not support the Confederation, deferring to Master Skywalker. Skywalker stated that the Jedi's fight was solely against Jacen, and Han Solo proposed neutrality between the Confederation and the combined Wookiee, Hapan, and Jedi forces. Thus, while the factions did not unite against the Galactic Alliance, they agreed not to interfere in each other's affairs.
The Jedi Order, under Skywalker, secretly relocated to the old Imperial outpost on the forest moon of Endor, where Kyp Durron planned a mission to plant a tracking device on Jacen. Despite his efforts to locate the new Jedi base, Darth Caedus failed and was instead preoccupied with regaining the Hapan Consortium's fleets, which had previously constituted a significant portion of the Galactic Alliance's military. He issued an ultimatum to Tenel Ka after kidnapping their daughter, Allana, but only secured Hapan neutrality.
Han Solo and Leia Organa Solo remained on Kashyyyk to combat the wildfires ignited by their son. Using the Millennium Falcon, they placed beacons to allow a Confederation cruiser to create dead zones, preventing the wildfires from spreading. Lando Calrissian joined them, assisting the Wookiees in extinguishing the fires.